Research ArticleChemical Composition Total Phenolic Content and AntioxidantActivities of the Essential Oils of the Leaves and Fruit Pulp ofAnnona muricata L (Soursop) from Ghana

Joseph Nana Gyesi1 Rita Opoku2 and Lawrence Sheringham Borquaye 12

1Department of Chemistry Kwame Nkrumah University of Science and Technology Kumasi Ghana2Central Laboratory Kwame Nkrumah University of Science and Technology Kumasi Ghana

Correspondence should be addressed to Lawrence Sheringham Borquaye slborquayegmailcom

Received 4 June 2019 Revised 16 July 2019 Accepted 17 July 2019 Published 2 September 2019

Academic Editor Gary Lorigan

Copyright copy 2019 Joseph Nana Gyesi et al is is an open access article distributed under the Creative Commons AttributionLicense which permits unrestricted use distribution and reproduction in any medium provided the original work isproperly cited

Annona muricata also called soursop is widespread in many tropical countries and various parts of the plant have been shown topossess very good pharmacological properties is work evaluated the chemical composition and antioxidant activities ofessential oils obtained from the fruit pulp and leaves of soursop Essential oils were obtained via hydrodistillation and char-acterized by gas chromatography-mass spectrometry Antioxidant potential was evaluated via the phosphomolybdenum hy-drogen peroxide scavenging and 11-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assays In the leaf essential oil atotal of 31 compounds were identified with δ-cadinene (2258) and α-muurolene (1064) being the most abundant irty-twocompounds were identified in the fruit pulp essential oil with Ccedil-sitosterol (1982) and 2-hydroxy-1-(hydroxymethyl) ethyl ester(1348) being present in high amounts Both essential oils showed very good total antioxidant capacities (4903 gAAE100 g and5088 gAAE100 g for fruit pulp and leaf essential oils respectively) e IC50 values from the DPPH assay were 2448plusmn 32 μgmLfor leaf essential oil and 512plusmn 51 μgmL for the fruit pulp essential oil At 1mgmL hydrogen peroxide scavenged was below 50for both leaf and fruit pulp essential oils indicatingmoderate activityese results suggest possible application of the essential oilsof Annona muricata in food preservation and processing

1 Introduction

Antioxidants have garnered a lot of attention in recent timesdue to their potential in the prevention and treatment ofradical-mediated diseases Reactive oxygen species (ROS)and reactive nitrogen species (RNS) provide oxidativeradicals which interact with and damage macromoleculessuch as proteins lipids and DNA [1ndash3] Oxidative damageto these macromolecules has been implicated in a number ofhuman pathological processes such as diabetes pulmonarydysfunction atherosclerosis and neurological diseases[4ndash6] Lipid oxidation also plays a critical role in the foodindustry Reduction in food quality and loss of nutritionalvalue are associated with the oxidative degradation of lipids[7] To ameliorate the effects of radicals various compoundshave been explored Compounds such as butylated

hydroxyanisole (BHA) or butylhydroxytoluene (BHT) arecommonly used in the food industry as antioxidants [8]ese synthetic compounds are however suspected to haveharmful effects on human health and their use is thereforediscouraged [9 10] Some of the synthetic antioxidants (suchas α-tocopherol and BHT) exhibit poor activities in complexfood systems [11] and foods enriched with long chainomega-3 fatty acids [12] Natural antioxidants with lowtoxicities have therefore been the focus of many researchworks One class of natural products that have shownpromise in this regard is essential oils [13]

Essential oils are aromatic oily liquids made up ofmixtures of volatile compounds obtained usually viahydrodistillation steam distillation dry distillation or amechanical process without the application of heat from aplant or a plant part ey usually possess a strong odor are

HindawiBiochemistry Research InternationalVolume 2019 Article ID 4164576 9 pageshttpsdoiorg10115520194164576

seldom colored and are generally lower in density relative towater Essential oils have been isolated from all plant organssuch as flowers buds seeds leaves twigs bark herbs woodfruits and root [14 15] e use of essential oils for theirbeneficial human properties has been in existence sinceantiquity and is documented in primordial literature[16 17] Some of these properties of essential oils such asanti-inflammatory antimicrobial and antioxidant havebeen verified in the recent scientific literature [14 18ndash20]e oxidative stability of essential oils stems largely from theenormous diversity of compounds that constitute these oils[18] Several essential oils are known to possess very goodantioxidant capabilities and this can be utilized in theprotection of other substances like food and animal feedpreservation Animal products (egg meat and fat) withimproved dietary value better oxidative stability and longershelf life may be obtained by using essential oils as additivesin feedstuffs for farm animals [21]

Annona muricata L (Annonaceae) also called soursop isa tropical plant found in parts of the Americas Asia Aus-tralia and Africa It possesses thick leaves that are shiny onthe upper side e leaves are obovate oblate and acuminateto varying degrees e soursop fruit is dark green pricklyand ovoid with juicy acidic whitish and aromatic pulp[22 23] e use of Annona muricata in traditional medicineis well documented Ethnobotanical studies have describedthe plant as being used to treat various disease conditions likebacterial infections fever respiratory and skin illnessdiabetes internal and external parasites hypertension in-flammation pain and cancer [22] Extracts of the plant havebeen shown to possess antimicrobial anti-inflammatoryantiprotozoan antioxidant and antitumor characteristics Invivo studies of the plant extracts has revealed wound healingantiulceric hepatoprotective anxiolytic contraceptive an-tistress hypoglycemic anti-inflammatory antitumoral andanti-icteric activities Over 200 compounds have been iso-lated from the plant with most being alkaloids phenols andacetogenins [22] Some acetogenins and alkaloids isolatedfrom the plant have shown neurotoxicity [22ndash24]

Essential oils from various parts of Annona muricatahave been the subject of a number of investigations Es-sential oils have been isolated from different organs of theplant such as fruit pulp leaves and fruit peel as well asplants from different locations in Africa Asia and theAmericas [25ndash37] Interestingly for the same plant partdifferences in the chemical composition of the essentialoils have been observed is motivated this work onAnnona muricata from Ghana e present work describesthe composition of essential oils from the leaves and fruitpulp of Ghanaian cultivars of Annona muricata In ad-dition the antioxidant activities of the essential oils wereevaluated

2 Methods

21 PlantMaterial Fresh fruits of Annona muricata L werepurchased from the local market in Kumasi Ghana Freshleaves were collected from a farm at Ayeduase in KumasiPlant identification and authentication were carried out at

the Herbarium Section of the Department ofeoretical andApplied Biology Kwame Nkrumah University of Scienceand Technology (KNUST) Kumasi

22 Isolation of Volatile Compounds e pulp of the freshfruit was separated from the peel and seed and 680 g of thepulp placed in a hydrodistillation apparatus e setup forhydrodistillation consisted of a modified Clavenger glass-ware a condenser a round bottom flask a heating mantleand a receiving flask as described elsewhere After 4 hours ofdistillation 780mg (011) of essential oil was obtainedSimilarly 120 g of fresh leaves was placed in the hydro-distillation apparatus and after 4 hours of distillation800mg (sim067) of essential oil was obtained

23 Gas Chromatography Analysis Gas chromatography-mass spectrometer (GC-MS) analysis of the essential oilsfrom fruit pulp and leaves were performed using a gaschromatograph (PerkinElmer GCClarus 580) interfaced to aPerkinElmer mass spectrometer (Clarus SQ 8 S) equippedwith Elite-5MS (5 diphenyl95 dimethyl poly siloxane)fused capillary column (30times 025mm IDtimes 025 μm DF) Atfirst the oven temperature was maintained at 35degC for2minutes and then it was ramped up to 250degC at a rate of10degCminute and finally to 320degC at a rate of 20degCminutewhere it was held for 23minutes For mass spectrometerdetection an electron ionization system was operated in theelectron impact mode Helium was used as a carrier gas at aconstant flow rate of 1mLminute and an injection volumeof 1 μL was employed e injector temperature wasmaintained at 250degC and the ion-source temperature waskept at 150degC Mass spectra were taken at 70 eV and a scaninterval of 05 seconds over a mass range of 50 to 450Daesolvent delay was 0 to 4minutes and the total GCMS runtime was 50minutes Constituents were identified bycomparison of their retention indices relative to n-alkanesand fragmentation pattern from mass spectra which werecompared to the mass spectra in the database of NationalInstitute Standard and Technology (NIST) and publishedliterature of spectral data whenever possible e assignedcompound names were made solely by using the similarityindices obtained from the Wiley and NIST libraries for theGC-MS system used and some published literature ofspectral data e relative percentages of the various con-stituents were expressed as percentages calculated by nor-malization of the peak area [38 39]

24 Evaluation of Antioxidant Activities Antioxidant po-tential of essential oils and hydrosols was evaluated bydifferent in vitro assays the phosphomolybdenum assayhydrogen peroxide scavenging assay and the 22-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay Allchemicals used for the antioxidant activity evaluations wereobtained from Sigma-Aldrich (St Louis MO USA)

241 Phosphomolybdenum (PM) Assay e assay relies onthe reduction of Mo (VI) to Mo (V) by the analyte of interest

2 Biochemistry Research International

followed by the subsequent formation of a green phosphateMo (V) complex at acidic pH [40] Five milliliters of the PMreagent (06M sulphuric acid 28mM sodium phosphateand 4mM ammonium molybdate) was added to 05mL ofeach test sample in a test tube e test tubes were cappedand shaken and then incubated at 95degC for 90minutes Aftersamples had cooled to room temperature absorbance wastaken at 695 nm against a blank solution Blank solution wasmade by replacing the test sample with solvent in themixture and incubated under similar conditions Ascorbicacid was used as the standard Antioxidant capacity wasexpressed as equivalents of ascorbic acid with the followingequation

TAC C times V

Mtimes 100 (1)

where TAC is the total antioxidant capacity in gAAE100 gof the test sample C is the concentration of ascorbic acid(μgmL) V is the volume of the reaction mixture and M isthe mass of the essential oil in the reaction mixture

242 Hydrogen Peroxide Scavenging Assay is method isbased on the ability of 110-phenanthroline to form anorange complex with ferrous ion and the reduction offerrous ion to ferric ion by hydrogen peroxide [41] To05mL ferrous ammonium sulphate (1mM) solution wasadded 3mL of varying concentrations of essential oil(prepared in 5 DMSO) and 013mL of 5mMH2O2 esamples were incubated at room temperature away fromlight for 5minutes ereafter 3mL 110-phenanthroline(1mM) was added to each tube mixed well and incubatedagain at room temperature for 10minutes e absorbanceof each reaction mixture was taken at 510 nm using UV-Visspectrophotometer Water was used in place of essential oilfor the blank solution Percent hydrogen peroxide scavengedwas calculated from the following equation

hydrogen peroxide scavenged Atest

Acontroltimes 100 (2)

where Atest is the absorbance of the test sample and Acontrol isthe absorbance of the blank

243 DPPH Assay eDPPH radical scavenging activity ofthe essential oils was evaluated using slightly modifiedstandard methods Essential oils of different concentrationswere prepared in 5 DMSO A solution of DPPH (01mM)was prepared in methanol To 40 μL of essential oil wasadded 160 μL of DPPH solution e reaction mixture wasthoroughly mixed together and incubated in the dark atroom temperature for 30minutes ereafter the absor-bance of the mixture was read at 517 nm For the reactionblank methanol was used in the place of essential oilsAscorbic acid was used as the positive control e percentDPPH radical scavenged was calculated from the followingequation

DPPH radical scavenged Acontrol minus Asample

Acontrol1113888 1113889 times 100

(3)

where Acontrol is the absorbance of blank and Asample is theabsorbance of sample mixture [42 43]

244 Total Phenolic Content (FolinndashCiocalteu Method)is method is based on the oxidation of phenolic groups byusing FolinndashCiocalteursquos reagent To 5mL of 10 FolinndashCiocalteu reagent was added 1mL of sample solution ofvarying concentrations e mixture was thoroughly mixedand allowed to stand for 5minutes at room temperatureAfter this 4mL of 7 NaHCO3 was added slowly and thereaction mixture was allowed to stand in the dark for30minutes at room temperature Absorbance readings weretaken at 765 nm e same procedure was repeated for allstandard gallic acid solutions e phenolic content wasobtained from the gallic acid calibration curve and expressedas grams of gallic acid equivalent per 100 gram of dry weightof sample (gGAE100 g) [39]

245 Data Analysis All experiments were conducted intriplicates and data presented as meanplusmn standard deviationStatistical analysis was performed using GraphPad Prism 60for Windows (GraphPad Software San Diego CA USA)Where necessary significance was evaluated using analysisof variance (ANOVA) followed by Sidakrsquos multiple com-parison test at Plt 005

3 Results

e essential oils from the leaf and fruit pulp of Annonamuricata were obtained by hydrodistillation in a Clavenger-type set up For the fruit pulp an amber-colored oil rep-resenting a yield of 011 was obtained after concentrationin vacuo A light yellow oil was obtained from the hydro-distillation of fresh leaves of Annona muricata with a yieldof 067

e total ion chromatogram (TIC) obtained from theGC-MS analysis of the essential oils are presented in Figure 1(fruit pulp) and Figure 2 (leaf ) For the leaf essential oil 31compounds representing 9998 of the constituents wereidentified (Table 1) whereas 32 compounds representing9999 were identified in the fruit pulp essential oil (Ta-ble 2) ere was marked difference in the chemical com-position of the two oils Whereas the leaf essential oilsconsisted largely of terpenes and terpenoids the fruit pulpessential oils were made up of aliphatic compounds (acidsesters and alcohols) e sesquiterpenes δ-cadinene(2258) and α-muurolene (1064) were the most abun-dant compounds identified in the leaf essential oils editerpenoid andrographolide was also present in largeamounts with a composition of 651 τ-cadinol ledeneoxide (II) α-cardinol and β-caryophyllene completed thetop six most abundant compounds in the leaf essential oils3-(Octadecyloxy) propyl ester (557) and octadecane(533) were the most abundant aliphatic compounds

Biochemistry Research International 3

present in the leaf essential oil Gitoxigenin a phytosterolwas also present D-limonene and α-pinene both mono-terpenes were also identified in the leaf essential oilα-pinene was present in the lowest concentration makingup only 004 of the total composition

e essential oil from the fruit pulp was made up ofmainly aliphatic compounds and phytosterols e mostabundant compound was the phytosterol ς-sitosterol whichmade up 1982 of the essential oil Aliphatic compoundslike 2-hydroxy-1-(hydroxymethyl) ethyl ester (1348) 2-hexenoic acid methyl ester (1027) 2-propenoic acid 3-phenyl- methyl ester (867) and 9-octadecanoic acid

(459) were also present in high amounts Terpene com-pounds identified in the essential oil were squalene (a tri-terpene) and the sesquiterpenes 45-di-epi-aristolocheneand β-guaiene Other phytosterols present were α-sitosterol(304) c-sitosterol (496) and campesterol (219) Anumber of straight-chain alkanes such as nonane dodecaneand tridecane were also present in varying amounts Phe-nylacetaldehyde was the only aldehyde identified in theessential oil from the fruit pulp of Annona muricata

e antioxidant activities of the essential oils were de-termined using the phosphomolybdenum assay and DPPHand H2O2 scavenging assays e total phenolic content of

2-Hexenoic acid methyl ester

O

O

Ccedil-Sitosterol

oleyl oleate

O

O

425 625 825 1025 1225 1425 1625 1825 2025 2225 2425 2625 2825 3025 3225 3425 3625Time

3825 4025 4225 4425 4625 4825

100

0

() 774

696

811 1002 1112 11581305

1431

1483

1605 2054

2226 2293 2345

2682 2845 29813063

31633266

32442373

2508

2598

HO

CH3

CH3

CH3

CH3H3C

H3C

H

H H

H

2-Propenic acid 3-phenylmethyl ester

Figure 1 GC-MS spectra of the fruit pulp essential oil of Annona muricata and the chemical structure of some of the constituents

α-Copaene

α-Muurolene

δ-Cadinene

6-epi-Shyobunol

τ-Cadinol

HO

OH

H

HH

H

Figure 2 GC-MS spectra of the leaf essential oil of Annona muricata and the chemical structure of some of the constituents

4 Biochemistry Research International

the oils was also determined e total antioxidant capacityas determined from the phosphomolybdenum assay was4903 gAAE100 g and 5088 gAAE100 g for fruit pulp andleaf essential oils respectively (Table 3) ere was no sig-nificant difference (Plt 005) between the antioxidant ca-pacities of both the leaf and fruit pulp essential oils e leafessential oil proved to be a better scavenger of the DPPHradical than the fruit pulp essential oil e IC50 for the leafessential oil was 2448plusmn 32 μgmL whereas that for the fruitpulp was 512plusmn 51 μgmL (Table 4) At 10mgmL the fruitpulp essential oil scavenged about 24 of H2O2 while the leafessential oil scavenged about 32 of H2O2 at 1mgmL

(Table 4) e leaf essential oil thus proved to be a betterH2O2 scavenger than the fruit pulp essential oil In terms ofphenolic content there were more phenolic compounds inthe leaf essential oil than there was in the fruit pulp essentialoil (Table 3)

4 Discussions

e yield of the essential oils obtained in this work was in asimilar range to that obtained from Annona muricata byother researchers In general essential oil yields are less than1 e fruit pulp produced a slighter higher yield than theleaves in this study Different plant organs produce differentamountslevels of essential oils and this usually reflects thefunction of the oils in that plant organ

e leaf essential oils were mainly terpenes whereas thepulp essential oils were made up of aliphatic compounds andsterols similar to other results in the literature [28ndash30 33]e most abundant component of the leaf essential oil wasδ-cadinene is compound has been identified in the leafessential oils of Annona muricata from other locations asshown in Table 5 [27 29 32 33] Other works on the leafessential oils of Annona muricata (Table 5) showed thatβ-caryophyllene was the major constituent [27 29 33] Eventhough present in the leaf essential oil from Ghanaβ-caryophyllene was not the most abundant constituentOther sesquiterpenes and terpenoids such α-muuroleneτ-cadinol α-cadinol and α-humulene present were com-mon to this study and results from other works (Table 5)

For the fruit pulp essential oils Ccedil-sitosterol a plant ste-roidal hormone necessary for some physiological processessuch as cell elongation and cellulose biosynthesis [44] wasidentified as the most abundant component Campesterolanother phytosterol with similar functions as sitosterol wasalso identified in the fruit essential oils In general howevermajority of the components identified in the fruit essential oilswere aliphatic compoundsmade up of esters alkanes alcoholsaldehydes and fatty acids 2-Hexenoic acid methyl ester (ormethyl-2-hexenoate) which was present in this study as the 2nd

most abundant constituent was present in the pulp essentialoils from other locations [28 30 33 34] e levels werehowever different Variations in essential oil composition fromthe same plant organ may be due to a variety of factorsSeasonal variations in chemical composition of essential oilshave been reported in the literature is difference inchemical composition due to seasonal variations has beenobserved to affect the bioactivity of the essential oils as well[45 46] Other reasons for differences in the chemical com-position of essential oils from the same plant organ includeenvironmental and genetic factors geographical variationschemotypic diversity plant maturation stage and nutritionalstatus of the plant [46ndash49] us two plants of the samespecies but different chemotypes will produce essential oilswith variations in chemical composition e differences inessential oil compositions of Annona muricata leaf and fruitpulp in this and other works may be attributed to one or anycombination of these elements

e antioxidant potential of the leaf and fruit pulp es-sential oils as evaluated from the phosphomolybdenum

Table 1 Composition of leaf essential oil of Annona muricata asdetermined by GC-MS with tentative identified compounds

No RT SI Compound composition1 716 87 α-Pinene (D)- 0042 887 96 Limonene (D)- 025

3 1159 98 Methyl (9E)-9-octadecen-12-ynoate 036

4 1306 89 6-Methyloctadecane 0215 1362 90 δ-EIemene 1046 1421 98 α-Copaene 4217 1439 99 β-Elemene 0188 1465 95 α-Muurolene 10649 1465 91 Andrographolide 65110 1484 98 Ledene oxide (II) 62911 1484 98 β-Caryophyllene 55712 1508 92 α-Acorenol 00613 1514 83 β-cis-farnesene 27214 1530 97 α-Humulene 14415 1537 97 c-Muurolene 02116 1552 98 α-Selinene 11317 1574 91 4-epi-cubedol 08818 1601 96 Caryophyllene oxide 11519 1609 97 δ-Cadinene 225820 1680 97 Cubenol 194

21 1691 94 2-Hexadecen-1-ol 371115-tetramethyl 039

22 1775 97 α-Cadinol 565

23 1930 96 Methyl 1012-pentacosadiynoate 199

24 1963 88 β-Viternene 02525 1973 91 Cedren-13-ol 01226 2007 95 Gitoxigenin 137

27 2014 96 16-Octadecenoic acid methylester 026

28 2026 95 3-(Octadecyloxy) propyl ester 55729 2235 94 6-epi-shyobunol 51730 2557 99 τ-Cadinol 64731 2727 90 Octadecane 533

Terpenes 5026Oxygenated terpenes

(terpenoids) 3424

Esters 818Alkanes 554Sterol 137Alcohol 039Total 9998

No compound number in order of elution SI Similarity Index (librarysearch of purity value of a compound) RT retention time in minutes

Biochemistry Research International 5

DPPH scavenging and hydrogen peroxide assays revealedpromising antioxidant properties (Tables 3 and 4) emechanism of antioxidant activity includes prevention of theformation of the initiator radical and termination of radicalsin the chain propagation stage or via indirect routes such asenhancement of the activities of enzymes that mop up

reactive species or induction in the expression of theseenzymes [18 50] Because essential oils consist of a numberof different compounds the antioxidant activity observed isusually the synergistic effect of the various constituents [18]

Table 2 Composition of fruit pulp essential oil of Annona muricata as determined by GC-MS with tentative identified compounds

No RT SI Compound composition1 651 80 Nonane 1742 696 98 Hexanoic acid methyl ester 1863 774 96 2-Hexenoic acid methyl ester 10274 811 94 Pentanoic acid 2-hydroxy-4-methyl- methyl ester 0035 818 98 Pentanoic acid 2-hydroxy-3-methyl- methyl ester 0426 935 94 268-Trimethylbicyclo[420]oct-2-ene-18-diol 0237 1002 99 16-Octadien-3-ol 37-dimethyl- 0138 1112 94 2-Octenoic acid methyl ester (E)- 0489 1158 92 Dodecane 05910 1200 94 Phenylacetaldehyde 17111 1305 91 Tridecane 04312 1431 97 2-Propenoic acid 3-phenyl- methyl ester 86713 1483 98 β-Caryophyllene 17714 1530 96 45-di-epi-Aristolochene 03515 1572 93 Falcarinol 01816 1605 99 β-Guaiene 01717 2054 94 Hexadecanoic acid methyl ester 03318 2226 94 Glyceryl 2-laurate 15219 2231 99 9-Octadecenoic acid methyl ester (E)- 21820 2507 97 8-Octadecanoic acid 22021 2508 99 2-Hydroxy-1-(hydroxymethyl) ethyl ester 134822 2558 96 Ccedil-Sitosterol 198223 2644 94 9-Octadecanoic acid 45924 2644 96 Pentadecanoic acid 13-methyl- methyl ester 04225 2693 80 23-Dihydroxypropyl elaidate 38126 2702 96 Squalene 17427 2728 97 α-Sitosterol 30428 2728 99 Oleic acid 20029 2763 87 Octadecane 20330 2981 91 Campesterol 21931 3062 96 Υ-Sitosterol 49632 3244 99 Oleyl oleate 25333 3265 86 Nonadecatriene-514-diol 412

Esters 4600Sterols 3001Terpenes 403Alcohols 466Alkanes 479Aldehyde 171

Carboxylic acid 879Total 9999

No compound number in order of elution SI Similarity Index (library search of purity value of a compound) RT retention time in minutes

Table 3 Total antioxidant capacity (TAC) and total phenoliccontent (TPC) of fruit pulp and leaf essential oils

Sample TAClowast gAAE100 g TPClowastlowast gGAE100 gPulp essential oil 4903plusmn 048a 398plusmn 060bLeaf essential oil 5088plusmn 050a 438plusmn 042b

Columns with different letters indicate significant difference (Plt 005Sidakrsquos multiple comparison test) lowastTAC expressed in gram ascorbic acidequivalent per 100 g of sample (gAAE100 g) lowastlowastTPC expressed in gramgallic acid equivalent per 100 g of sample (gGAE100 g)

Table 4 DPPH free radical and hydrogen peroxide scavengingactivities of essential oils and hydrosols from leaf and fruit pulp ofAnnona muricata

Sample IC50 (μgmL)lowast H2O2 scavengedlowastlowast

Pulp essential oil 5120plusmn 51 2438plusmn 021Leaf essential oil 2448plusmn 32 3180plusmn 051Ascorbic acid 213plusmn 32 NDGallic acid ND 9500plusmn 112lowastlowastlowastlowastIC50 concentration of extract required to scavenge 50 of DPPH radicalslowastlowast H2O2 scavenged was determined at 1mgmL for essential oils lowastlowastlowastForgallic acid H2O2 scavenged was determined at 50 μgmL

6 Biochemistry Research International

In the DPPH radical scavenging assay a dose-dependentinhibition of the DPPH radical was observed in essential oiland standard ascorbic acid treatments e IC50 valuesobtained for the leaf and fruit pulp essential oils indicate agood inhibition of the DPPH radical In the hydrogenperoxide scavenging assay the leaf essential oil showedsuperior activity to the pulp essential oil e activity of bothessential oils could however be described as average as thepercent inhibition of hydrogen peroxide was less than 50for both oils

Both essential oils however displayed very good totalantioxidant activity as seen in Table 3 Both oils had highlevels of phenolic content and this may have contributed tothe antioxidant activities observed It has been postulatedthat phenolic compounds possess high reactivity towardsperoxyl radicals via a formal hydrogen atom transfer andthis is the basis of their antioxidant activity [18 51] Phenoliccompounds are therefore categorized as chain breaking

antioxidants [52] Many reports on the antioxidant potentialof essential oils exist [13] and this report further confirmsthe importance of essential oils as antioxidative agents Sincereactive oxygen species cause serious damage to nucleicacids proteins and lipids the impressive antioxidant ac-tivity of the essential oils from Annona muricata suggestspossible use as natural antioxidant source in food additivesand animal feed formulation

5 Conclusion

Sesquiterpenes were the major constituents of the leaf es-sential oils of Annona muricata from Ghana whereas thefruit pulp essential oil consisted of aliphatic compounds andsterols e most abundant compound in leaf essential oilwas δ-cadinene In the fruit pulp essential oil Ccedil-sitosterolwas most abundant Both essential oils displayed promisingantioxidant activities and suggests potential application in

Table 5 Comparison of leaf and fruit pulp essential oil composition from different studies

Source Location Constituents ( composition)Leaves

Present findings Ghana

δ-Cadinene (2258) α-muurolene (1064)andrographolide (651) τ-cadinol (647) ledene

oxide (II) (629) α-cadinol (565) β-caryophyllene(557)

[33] Cote drsquoIvoireβ-Caryophyllene (314) δ-cadinene (67)

α-muurolene (55) (E)-2-hexenol (48) τ-cadinol(43)

[29] Beninβ-Caryophyllene (136) δ-cadinene (91) epi-

α-cadinol (84) α-cadinol (83) isocaryophyllene(75)

[32] Nigeria (E)-Caryophyllene (389) eugenol (302) δ-cadinene(60) caryophyllene oxide (50) α-humulene (43)

[35] Vietnam β-Pinene (206) germacrene D (181) p-mentha-24(8)-diene (98) α-pinene (94) β-elemene (91)

[27] Cameroon β-Caryophyllene (40) β-elemene (144) α-santalene(95) (Z)-hex-3-enol (52) δ-cardinene (48)

[26] Egypt Bicycloelemene (236) limonene (166) β-pinene(143) α-fenchene (66) α-pinene (54)

Fruit pulp

Present findings Ghana

Ccedil-Sitosterol (1982) 2-hydroxy-1-(hydroxymethyl)ethyl ester (1348) 2-hexenoic acid methyl ester(1027) 2-propenoic acid 3-phenyl- methyl ester

(867) Υ-sitosterol (496)

[36] MalaysiaMethyl (E)-2-butenoate (1970) Methyl (E)-2-hexenoate (1840) (Z)-3-hexenol (97) linalool

(930) methyl 2-hydroxyhexanoate (52)

[33] Cote drsquoIvoire

Methyl (E)-2-hexenoate (398) 3-pyridinocarbonylhydrazide (78) methyl hexanoate

(54) methyl (E)-2-butenoate (48) 23-dihydrobenzofuran (45)

[34] CubaMethyl 3-phenyl-2-propenoate (106) hexadecanoicacid (97) methyl (E)-2-hexenoate (88) methyl 2-

hydroxy-4-methylvalerate (72) linalool (29)

[30] Sri LankaMethyl hexanoate (3095) methyl (E)-hex-2-enoate(2670) trans-β-farnesene (645) dichloromethane

(572) methyl but-2-enoate (475)

[28] Cameroon2-Hexenoic acid methyl ester (239) β-caryophyllene(127) 18-cineole (99) 2-hexenoic acid ethyl ester

(86) linalool (78)

Biochemistry Research International 7

food processing and preservation as well as cosmetic andpharmaceutical industries

Data Availability

All data generated or analyzed during this study are includedin this published article

Conflicts of Interest

All authors declare no competing financial professional orpersonal interests that might have influenced the perfor-mance or presentation of this work

Authorsrsquo Contributions

LSB conceived the study LSB JNG and RO designed allexperiments LSB JNG and RO collected the samples JNGand RO carried out all the experiments LSB JNG and ROperformed the data analysis JNG drafted and LSB edited theinitial manuscript All authors read and approved the finalmanuscript JNG and RO contributed equally to this work

Acknowledgments

e authors are grateful to the Department of Chemistry andthe KNUST Central Laboratory for the use of their facilitiesfor this study e authors acknowledge Miss Judith Ananeof KNUST for technical support

References

[1] Y-Z Fang S Yang and G Wu ldquoFree radicals antioxidantsand nutritionrdquo Nutrition vol 18 no 10 pp 872ndash879 2002

[2] L Lyras N J Cairns A Jenner J Peter and B Halliwell ldquoAnassessment of oxidative damage to proteins lipids and DNAin brain from patients with Alzheimerrsquos diseaserdquo Journal ofNeurochemistry vol 68 no 5 pp 2061ndash2069 1997

[3] L J Machlin and A Bendich ldquoFree radical tissue damageprotective role of antioxidant nutrientsrdquo FASEB Journalvol 1 no 6 pp 441ndash445 1987

[4] B Halliwell ldquoLipid peroxidation antioxidants and cardio-vascular disease how should we move forwardrdquo Cardio-vascular Research vol 47 no 3 pp 410ndash418 2000

[5] P Poprac K Jomova M Simunkova V Kollar C J Rhodesand M Valko ldquoTargeting free radicals in oxidative stress-related human diseasesrdquo Trends in Pharmacological Sciencesvol 38 no 7 pp 592ndash607 2017

[6] K Yagi ldquoLipid peroxides and human diseasesrdquo Chemistry andPhysics of Lipids vol 45 no 2ndash4 pp 337ndash351 1987

[7] K H S Farvin and C Jacobsen ldquoPhenolic compounds andantioxidant activities of selected species of seaweeds fromDanish coastrdquo Food Chemistry vol 138 no 2-3 pp 1670ndash1681 2013

[8] E R Sherwin ldquoAntioxidantsrdquo Food Additives vol 139ndash1931990

[9] R S Lanigan and T A Yamarik ldquoFinal report on the safetyassessment of BHT (1)rdquo International Journal of Toxicologyvol 21 pp 19ndash94 2002

[10] R C Lindenschmidt A F Tryka M E Goad andH P Witschi ldquoe effects of dietary butylated hydrox-ytoluene on liver and colon tumor development in micerdquoToxicology vol 38 no 2 pp 151ndash160 1986

[11] Y He and F Shahidi ldquoAntioxidant activity of green tea and itscatechins in a fish meat model systemrdquo Journal of Agriculturaland Food Chemistry vol 45 no 11 pp 4262ndash4266 1997

[12] C Jacobsen M B Let N S Nielsen and A S MeyerldquoAntioxidant strategies for preventing oxidative flavour de-terioration of foods enriched with N-3 polyunsaturated lipidsa comparative evaluationrdquo Trends in Food Science amp Tech-nology vol 19 no 2 pp 76ndash93 2008

[13] A K Dhakad V V Pandey S Beg J M Rawat and A SinghldquoBiological medicinal and toxicological significance of Eu-calyptus leaf essential oil a reviewrdquo Journal of the Science ofFood and Agriculture vol 98 no 3 pp 833ndash848 2018

[14] M G Miguel ldquoAntioxidant and anti-inflammatory activitiesof essential oils a short reviewrdquo Molecules vol 15 no 12pp 9252ndash9287 2010

[15] P Rubiolo B Sgorbini E Liberto C Cordero and C BicchildquoEssential oils and volatiles sample preparation and analysisA reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 282ndash290 2010

[16] K Husnu Can Baser and G BuchbauerHandbook of EssentialOils Science Technology and Applications CRC Press BocaRaton FL USA 2015

[17] H S Elshafie and I Camele ldquoAn overview of the biologicaleffects of somemediterranean essential oils on human healthrdquoBioMed Research International vol 2017 Article ID 926846814 pages 2017

[18] R Amorati M C Foti and L Valgimigli ldquoAntioxidant ac-tivity of essential oilsrdquo Journal of Agricultural and FoodChemistry vol 61 no 46 pp 10835ndash10847 2013

[19] J R Calo P G Crandall C A OrsquoBryan and S C RickeldquoEssential oils as antimicrobials in food systems-a reviewrdquoFood Control vol 54 pp 111ndash119 2015

[20] M K Swamy M S Akhtar and U Rani Sinniah ldquoAntimi-crobial properties of plant essential oils against humanpathogens and their mode of action an updated reviewrdquoEvidence-Based Complementary and Alternative Medicinevol 2016 Article ID 3012462 21 pages 2016

[21] R Perez-Roses E Risco R Vila P Pentildealver andS Cantildeigueral ldquoBiological and nonbiological antioxidant ac-tivity of some essential oilsrdquo Journal of Agricultural and FoodChemistry vol 64 no 23 pp 4716ndash4724 2016

[22] A V Coria-Tellez E Montalvo-Gonzalez E M Yahia andE N Obledo-Vazquez ldquoAnnona muricata a comprehensivereview on its traditional medicinal uses phytochemicalspharmacological activities mechanisms of action and toxic-ityrdquo Arabian Journal of Chemistry vol 11 no 5 pp 662ndash6912018

[23] S Moghadamtousi M Fadaeinasab S Nikzad G MohanH Ali and H Kadir ldquoAnnona muricata (Annonaceae) areview of its traditional uses isolated acetogenins and bi-ological activitiesrdquo International Journal of Molecular Sci-ences vol 16 no 7 pp 15625ndash15658 2015

[24] P Champy A Melot V Guerineau Eng et al ldquoQuantificationof acetogenins in Annona muricata linked to atypical par-kinsonism in guadelouperdquo Movement Disorders vol 20no 12 pp 1629ndash1633 2005

[25] K W Cheong C P Tan H Mirhosseini N S A HamidA Osman and M Basri ldquoEquilibrium headspace analysis ofvolatile flavor compounds extracted from soursop (Annonamuricata) using solid-phase microextractionrdquo Food ResearchInternational vol 43 no 5 pp 1267ndash1276 2010

[26] S S Elhawary M E E Tantawy M A Rabeh and E F NohaldquoDNA fingerprinting chemical composition antitumor andantimicrobial activities of the essential oils and extractives of

8 Biochemistry Research International

four Annona species from Egyptrdquo Journal of Natural SciencesResearch vol 3 no 59ndash68 p 11 2013

[27] F Fekam Boyom P H Amvam Zollo C Menut G Lamatyand J M Bessiere ldquoAromatic plants of tropical central AfricaPart XXVII Comparative study of the volatile constituents offive annonaceae species growing in Cameroonrdquo Flavour andFragrance Journal vol 11 no 6 pp 333ndash338 1996

[28] L Jirovetz G Buchbauer and M B Ngassoum ldquoEssential oilcompounds of the Annona muricata fresh fruit pulp fromCameroonrdquo Journal of Agricultural and Food Chemistryvol 46 no 9 pp 3719-3720 1998

[29] C Kossouoh M Moudachirou V Adjakidje J-C Chalchatand G Figueredo ldquoEssential oil chemical composition ofAnnona muricata L Leaves from Beninrdquo Journal of EssentialOil Research vol 19 no 4 pp 307ndash309 2007

[30] A J MacLeod and N M Pieris ldquoVolatile flavor componentsof soursop (Annona muricata)rdquo Journal of Agricultural andFood Chemistry vol 29 no 3 pp 488ndash490 1981

[31] C Marquez J Carlos A M Jimenez C Osorio R Jose andV Cartagena ldquoVolatile compounds during the ripening ofColombian soursop (Annona muricata L Cv Elita)rdquo Vitaevol 18 no 3 pp 245ndash250 2011

[32] M S Owolabi A Lanre Ogundajo N S Dosoky andW N Setzer ldquoe cytotoxic activity of Annona muricata leafoil from badagary NigeriardquoAmerican Journal of Essential Oilsand Natural Products vol 1 pp 1ndash3 2013

[33] Y Pelissier C Marion D Kone G Lamaty C Menut andJ-M Bessiere ldquoVolatile components of Annona muricata LrdquoJournal of Essential Oil Research vol 6 no 4 pp 411ndash4141994

[34] J A Pino J Aguero and R Marbot ldquoVolatile components ofsoursop (Annona muricata L)rdquo Journal of Essential Oil Re-search vol 13 no 2 pp 140-141 2001

[35] T D ang D N Dai T M Hoi and I A OgunwandeldquoStudy on the volatile oil contents of Annona glabra LAnnona squamosa L Annona muricata L and Annonareticulata L from Vietnamrdquo Natural Product Researchvol 27 no 13 pp 1232ndash1236 2013

[36] K C Wong and K H Khoo ldquoVolatile components ofMalaysian annona fruitsrdquo Flavour and Fragrance Journalvol 8 no 1 pp 5ndash10 1993

[37] A Wele I Ndoye and M Badiane ldquoFatty acid and essentialoil compositions of the seed oil of five Annona speciesrdquoNigerian Journal of Natural Products and Medicine vol 8no 1 pp 62ndash65 2004

[38] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Vol 456 Allured Pub-lishing Corporation Carol Stream IL USA 2007

[39] J K Patra Se-W Lee Y-S Kwon J Gyu Park andK-H Baek ldquoChemical characterization and antioxidant po-tential of volatile oil from an edible seaweed porphyra tenera(Kjellman 1897)rdquo Chemistry Central Journal vol 11 no 1p 34 2017

[40] P Prieto M Pineda and M Aguilar ldquoSpectrophotometricquantitation of antioxidant capacity through the formation ofa phosphomolybdenum complex specific application to thedetermination of vitamin Erdquo Analytical Biochemistryvol 269 no 2 pp 337ndash341 1999

[41] D Mukhopadhyay P Dasgupta D S Roy et al ldquoA sensitivein vitro spectrophotometric hydrogen peroxide scavengingassay using 110-phenanthrolinerdquo Free Radicals amp Antioxi-dants vol 6 no 1 2016

[42] L S Borquaye G Darko E Ocansey and E AnkomahldquoAntimicrobial and antioxidant properties of the crude

peptide extracts of Galatea paradoxa and Patella rusticardquoSpringerPlus vol 4 no 1 p 500 2015

[43] L S Borquaye G Darko N Oklu C Anson-Yevu andA Ababio ldquoAntimicrobial and antioxidant activities of ethylacetate and methanol extracts of Littorina littorea andGalateaparadoxardquo Cogent Chemistry vol 2 no 1 article 11618652016

[44] L Peng Y Kawagoe P Hogan and D Delmer ldquoSitosterol-beta- glucoside as primer for cellulose synthesis in plantsrdquoScience vol 295 no 5552 pp 147ndash150 2002

[45] A I Hussain F Anwar S T Hussain Sherazi andR Przybylski ldquoChemical composition antioxidant and an-timicrobial activities of basil (Ocimum basilicum) essential oilsdepends on seasonal variationsrdquo Food Chemistry vol 108no 3 pp 986ndash995 2008

[46] P C Santos-Gomes and M Fernandes-Ferreira ldquoOrgan- andseason-dependent variation in the essential oil composition ofSalvia officinalis L Cultivated at two different sitesrdquo Journal ofAgricultural and Food Chemistry vol 49 no 6 pp 2908ndash2916 2001

[47] W Aidi Wannes B Mhamdi B Marzouk and B MarzoukldquoVariations in essential oil and fatty acid composition duringMyrtus communis var italica fruit maturationrdquo FoodChemistry vol 112 no 3 pp 621ndash626 2009

[48] M Hudaib E Speroni A M Di Pietra and V Cavrini ldquoGCMS evaluation of thyme (Dymus vulgaris L) oil compositionand variations during the vegetative cyclerdquo Journal ofPharmaceutical and Biomedical Analysis vol 29 no 4pp 691ndash700 2002

[49] A M Viljoen S Subramoney S F v Vuuren K H C Baserand B Demirci ldquoe composition geographical variation andantimicrobial activity of Lippia javanica (verbenaceae) leafessential oilsrdquo Journal of Ethnopharmacology vol 96 no 1-2pp 271ndash277 2005

[50] C Demirci and A Studer Encyclopedia of Radicals inChemistry Biology and Materials Vol 2 John Wiley amp SonsChichester UK 2012

[51] M C Foti ldquoAntioxidant properties of phenolsrdquo Journal ofPharmacy and Pharmacology vol 59 no 12 pp 1673ndash16852007

[52] G W Burton T Doba E Gabe et al ldquoAutoxidation of bi-ological molecules 4 Maximizing the antioxidant activity ofphenolsrdquo Journal of the American Chemical Society vol 107no 24 pp 7053ndash7065 1985

Biochemistry Research International 9

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Submit your manuscripts atwwwhindawicom

followed by the subsequent formation of a green phosphateMo (V) complex at acidic pH [40] Five milliliters of the PMreagent (06M sulphuric acid 28mM sodium phosphateand 4mM ammonium molybdate) was added to 05mL ofeach test sample in a test tube e test tubes were cappedand shaken and then incubated at 95degC for 90minutes Aftersamples had cooled to room temperature absorbance wastaken at 695 nm against a blank solution Blank solution wasmade by replacing the test sample with solvent in themixture and incubated under similar conditions Ascorbicacid was used as the standard Antioxidant capacity wasexpressed as equivalents of ascorbic acid with the followingequation

TAC C times V

Mtimes 100 (1)

where TAC is the total antioxidant capacity in gAAE100 gof the test sample C is the concentration of ascorbic acid(μgmL) V is the volume of the reaction mixture and M isthe mass of the essential oil in the reaction mixture

242 Hydrogen Peroxide Scavenging Assay is method isbased on the ability of 110-phenanthroline to form anorange complex with ferrous ion and the reduction offerrous ion to ferric ion by hydrogen peroxide [41] To05mL ferrous ammonium sulphate (1mM) solution wasadded 3mL of varying concentrations of essential oil(prepared in 5 DMSO) and 013mL of 5mMH2O2 esamples were incubated at room temperature away fromlight for 5minutes ereafter 3mL 110-phenanthroline(1mM) was added to each tube mixed well and incubatedagain at room temperature for 10minutes e absorbanceof each reaction mixture was taken at 510 nm using UV-Visspectrophotometer Water was used in place of essential oilfor the blank solution Percent hydrogen peroxide scavengedwas calculated from the following equation

hydrogen peroxide scavenged Atest

Acontroltimes 100 (2)

where Atest is the absorbance of the test sample and Acontrol isthe absorbance of the blank

243 DPPH Assay eDPPH radical scavenging activity ofthe essential oils was evaluated using slightly modifiedstandard methods Essential oils of different concentrationswere prepared in 5 DMSO A solution of DPPH (01mM)was prepared in methanol To 40 μL of essential oil wasadded 160 μL of DPPH solution e reaction mixture wasthoroughly mixed together and incubated in the dark atroom temperature for 30minutes ereafter the absor-bance of the mixture was read at 517 nm For the reactionblank methanol was used in the place of essential oilsAscorbic acid was used as the positive control e percentDPPH radical scavenged was calculated from the followingequation

DPPH radical scavenged Acontrol minus Asample

Acontrol1113888 1113889 times 100

(3)

where Acontrol is the absorbance of blank and Asample is theabsorbance of sample mixture [42 43]

244 Total Phenolic Content (FolinndashCiocalteu Method)is method is based on the oxidation of phenolic groups byusing FolinndashCiocalteursquos reagent To 5mL of 10 FolinndashCiocalteu reagent was added 1mL of sample solution ofvarying concentrations e mixture was thoroughly mixedand allowed to stand for 5minutes at room temperatureAfter this 4mL of 7 NaHCO3 was added slowly and thereaction mixture was allowed to stand in the dark for30minutes at room temperature Absorbance readings weretaken at 765 nm e same procedure was repeated for allstandard gallic acid solutions e phenolic content wasobtained from the gallic acid calibration curve and expressedas grams of gallic acid equivalent per 100 gram of dry weightof sample (gGAE100 g) [39]

245 Data Analysis All experiments were conducted intriplicates and data presented as meanplusmn standard deviationStatistical analysis was performed using GraphPad Prism 60for Windows (GraphPad Software San Diego CA USA)Where necessary significance was evaluated using analysisof variance (ANOVA) followed by Sidakrsquos multiple com-parison test at Plt 005

3 Results

e essential oils from the leaf and fruit pulp of Annonamuricata were obtained by hydrodistillation in a Clavenger-type set up For the fruit pulp an amber-colored oil rep-resenting a yield of 011 was obtained after concentrationin vacuo A light yellow oil was obtained from the hydro-distillation of fresh leaves of Annona muricata with a yieldof 067

e total ion chromatogram (TIC) obtained from theGC-MS analysis of the essential oils are presented in Figure 1(fruit pulp) and Figure 2 (leaf ) For the leaf essential oil 31compounds representing 9998 of the constituents wereidentified (Table 1) whereas 32 compounds representing9999 were identified in the fruit pulp essential oil (Ta-ble 2) ere was marked difference in the chemical com-position of the two oils Whereas the leaf essential oilsconsisted largely of terpenes and terpenoids the fruit pulpessential oils were made up of aliphatic compounds (acidsesters and alcohols) e sesquiterpenes δ-cadinene(2258) and α-muurolene (1064) were the most abun-dant compounds identified in the leaf essential oils editerpenoid andrographolide was also present in largeamounts with a composition of 651 τ-cadinol ledeneoxide (II) α-cardinol and β-caryophyllene completed thetop six most abundant compounds in the leaf essential oils3-(Octadecyloxy) propyl ester (557) and octadecane(533) were the most abundant aliphatic compounds

Biochemistry Research International 3

present in the leaf essential oil Gitoxigenin a phytosterolwas also present D-limonene and α-pinene both mono-terpenes were also identified in the leaf essential oilα-pinene was present in the lowest concentration makingup only 004 of the total composition

e essential oil from the fruit pulp was made up ofmainly aliphatic compounds and phytosterols e mostabundant compound was the phytosterol ς-sitosterol whichmade up 1982 of the essential oil Aliphatic compoundslike 2-hydroxy-1-(hydroxymethyl) ethyl ester (1348) 2-hexenoic acid methyl ester (1027) 2-propenoic acid 3-phenyl- methyl ester (867) and 9-octadecanoic acid

(459) were also present in high amounts Terpene com-pounds identified in the essential oil were squalene (a tri-terpene) and the sesquiterpenes 45-di-epi-aristolocheneand β-guaiene Other phytosterols present were α-sitosterol(304) c-sitosterol (496) and campesterol (219) Anumber of straight-chain alkanes such as nonane dodecaneand tridecane were also present in varying amounts Phe-nylacetaldehyde was the only aldehyde identified in theessential oil from the fruit pulp of Annona muricata

e antioxidant activities of the essential oils were de-termined using the phosphomolybdenum assay and DPPHand H2O2 scavenging assays e total phenolic content of

2-Hexenoic acid methyl ester

O

O

Ccedil-Sitosterol

oleyl oleate

O

O

425 625 825 1025 1225 1425 1625 1825 2025 2225 2425 2625 2825 3025 3225 3425 3625Time

3825 4025 4225 4425 4625 4825

100

0

() 774

696

811 1002 1112 11581305

1431

1483

1605 2054

2226 2293 2345

2682 2845 29813063

31633266

32442373

2508

2598

HO

CH3

CH3

CH3

CH3H3C

H3C

H

H H

H

2-Propenic acid 3-phenylmethyl ester

Figure 1 GC-MS spectra of the fruit pulp essential oil of Annona muricata and the chemical structure of some of the constituents

α-Copaene

α-Muurolene

δ-Cadinene

6-epi-Shyobunol

τ-Cadinol

HO

OH

H

HH

H

Figure 2 GC-MS spectra of the leaf essential oil of Annona muricata and the chemical structure of some of the constituents

4 Biochemistry Research International

the oils was also determined e total antioxidant capacityas determined from the phosphomolybdenum assay was4903 gAAE100 g and 5088 gAAE100 g for fruit pulp andleaf essential oils respectively (Table 3) ere was no sig-nificant difference (Plt 005) between the antioxidant ca-pacities of both the leaf and fruit pulp essential oils e leafessential oil proved to be a better scavenger of the DPPHradical than the fruit pulp essential oil e IC50 for the leafessential oil was 2448plusmn 32 μgmL whereas that for the fruitpulp was 512plusmn 51 μgmL (Table 4) At 10mgmL the fruitpulp essential oil scavenged about 24 of H2O2 while the leafessential oil scavenged about 32 of H2O2 at 1mgmL

(Table 4) e leaf essential oil thus proved to be a betterH2O2 scavenger than the fruit pulp essential oil In terms ofphenolic content there were more phenolic compounds inthe leaf essential oil than there was in the fruit pulp essentialoil (Table 3)

4 Discussions

e yield of the essential oils obtained in this work was in asimilar range to that obtained from Annona muricata byother researchers In general essential oil yields are less than1 e fruit pulp produced a slighter higher yield than theleaves in this study Different plant organs produce differentamountslevels of essential oils and this usually reflects thefunction of the oils in that plant organ

e leaf essential oils were mainly terpenes whereas thepulp essential oils were made up of aliphatic compounds andsterols similar to other results in the literature [28ndash30 33]e most abundant component of the leaf essential oil wasδ-cadinene is compound has been identified in the leafessential oils of Annona muricata from other locations asshown in Table 5 [27 29 32 33] Other works on the leafessential oils of Annona muricata (Table 5) showed thatβ-caryophyllene was the major constituent [27 29 33] Eventhough present in the leaf essential oil from Ghanaβ-caryophyllene was not the most abundant constituentOther sesquiterpenes and terpenoids such α-muuroleneτ-cadinol α-cadinol and α-humulene present were com-mon to this study and results from other works (Table 5)

For the fruit pulp essential oils Ccedil-sitosterol a plant ste-roidal hormone necessary for some physiological processessuch as cell elongation and cellulose biosynthesis [44] wasidentified as the most abundant component Campesterolanother phytosterol with similar functions as sitosterol wasalso identified in the fruit essential oils In general howevermajority of the components identified in the fruit essential oilswere aliphatic compoundsmade up of esters alkanes alcoholsaldehydes and fatty acids 2-Hexenoic acid methyl ester (ormethyl-2-hexenoate) which was present in this study as the 2nd

most abundant constituent was present in the pulp essentialoils from other locations [28 30 33 34] e levels werehowever different Variations in essential oil composition fromthe same plant organ may be due to a variety of factorsSeasonal variations in chemical composition of essential oilshave been reported in the literature is difference inchemical composition due to seasonal variations has beenobserved to affect the bioactivity of the essential oils as well[45 46] Other reasons for differences in the chemical com-position of essential oils from the same plant organ includeenvironmental and genetic factors geographical variationschemotypic diversity plant maturation stage and nutritionalstatus of the plant [46ndash49] us two plants of the samespecies but different chemotypes will produce essential oilswith variations in chemical composition e differences inessential oil compositions of Annona muricata leaf and fruitpulp in this and other works may be attributed to one or anycombination of these elements

e antioxidant potential of the leaf and fruit pulp es-sential oils as evaluated from the phosphomolybdenum

Table 1 Composition of leaf essential oil of Annona muricata asdetermined by GC-MS with tentative identified compounds

No RT SI Compound composition1 716 87 α-Pinene (D)- 0042 887 96 Limonene (D)- 025

3 1159 98 Methyl (9E)-9-octadecen-12-ynoate 036

4 1306 89 6-Methyloctadecane 0215 1362 90 δ-EIemene 1046 1421 98 α-Copaene 4217 1439 99 β-Elemene 0188 1465 95 α-Muurolene 10649 1465 91 Andrographolide 65110 1484 98 Ledene oxide (II) 62911 1484 98 β-Caryophyllene 55712 1508 92 α-Acorenol 00613 1514 83 β-cis-farnesene 27214 1530 97 α-Humulene 14415 1537 97 c-Muurolene 02116 1552 98 α-Selinene 11317 1574 91 4-epi-cubedol 08818 1601 96 Caryophyllene oxide 11519 1609 97 δ-Cadinene 225820 1680 97 Cubenol 194

21 1691 94 2-Hexadecen-1-ol 371115-tetramethyl 039

22 1775 97 α-Cadinol 565

23 1930 96 Methyl 1012-pentacosadiynoate 199

24 1963 88 β-Viternene 02525 1973 91 Cedren-13-ol 01226 2007 95 Gitoxigenin 137

27 2014 96 16-Octadecenoic acid methylester 026

28 2026 95 3-(Octadecyloxy) propyl ester 55729 2235 94 6-epi-shyobunol 51730 2557 99 τ-Cadinol 64731 2727 90 Octadecane 533

Terpenes 5026Oxygenated terpenes

(terpenoids) 3424

Esters 818Alkanes 554Sterol 137Alcohol 039Total 9998

No compound number in order of elution SI Similarity Index (librarysearch of purity value of a compound) RT retention time in minutes

Biochemistry Research International 5

DPPH scavenging and hydrogen peroxide assays revealedpromising antioxidant properties (Tables 3 and 4) emechanism of antioxidant activity includes prevention of theformation of the initiator radical and termination of radicalsin the chain propagation stage or via indirect routes such asenhancement of the activities of enzymes that mop up

reactive species or induction in the expression of theseenzymes [18 50] Because essential oils consist of a numberof different compounds the antioxidant activity observed isusually the synergistic effect of the various constituents [18]

Table 2 Composition of fruit pulp essential oil of Annona muricata as determined by GC-MS with tentative identified compounds

No RT SI Compound composition1 651 80 Nonane 1742 696 98 Hexanoic acid methyl ester 1863 774 96 2-Hexenoic acid methyl ester 10274 811 94 Pentanoic acid 2-hydroxy-4-methyl- methyl ester 0035 818 98 Pentanoic acid 2-hydroxy-3-methyl- methyl ester 0426 935 94 268-Trimethylbicyclo[420]oct-2-ene-18-diol 0237 1002 99 16-Octadien-3-ol 37-dimethyl- 0138 1112 94 2-Octenoic acid methyl ester (E)- 0489 1158 92 Dodecane 05910 1200 94 Phenylacetaldehyde 17111 1305 91 Tridecane 04312 1431 97 2-Propenoic acid 3-phenyl- methyl ester 86713 1483 98 β-Caryophyllene 17714 1530 96 45-di-epi-Aristolochene 03515 1572 93 Falcarinol 01816 1605 99 β-Guaiene 01717 2054 94 Hexadecanoic acid methyl ester 03318 2226 94 Glyceryl 2-laurate 15219 2231 99 9-Octadecenoic acid methyl ester (E)- 21820 2507 97 8-Octadecanoic acid 22021 2508 99 2-Hydroxy-1-(hydroxymethyl) ethyl ester 134822 2558 96 Ccedil-Sitosterol 198223 2644 94 9-Octadecanoic acid 45924 2644 96 Pentadecanoic acid 13-methyl- methyl ester 04225 2693 80 23-Dihydroxypropyl elaidate 38126 2702 96 Squalene 17427 2728 97 α-Sitosterol 30428 2728 99 Oleic acid 20029 2763 87 Octadecane 20330 2981 91 Campesterol 21931 3062 96 Υ-Sitosterol 49632 3244 99 Oleyl oleate 25333 3265 86 Nonadecatriene-514-diol 412

Esters 4600Sterols 3001Terpenes 403Alcohols 466Alkanes 479Aldehyde 171

Carboxylic acid 879Total 9999

No compound number in order of elution SI Similarity Index (library search of purity value of a compound) RT retention time in minutes

Table 3 Total antioxidant capacity (TAC) and total phenoliccontent (TPC) of fruit pulp and leaf essential oils

Sample TAClowast gAAE100 g TPClowastlowast gGAE100 gPulp essential oil 4903plusmn 048a 398plusmn 060bLeaf essential oil 5088plusmn 050a 438plusmn 042b

Columns with different letters indicate significant difference (Plt 005Sidakrsquos multiple comparison test) lowastTAC expressed in gram ascorbic acidequivalent per 100 g of sample (gAAE100 g) lowastlowastTPC expressed in gramgallic acid equivalent per 100 g of sample (gGAE100 g)

Table 4 DPPH free radical and hydrogen peroxide scavengingactivities of essential oils and hydrosols from leaf and fruit pulp ofAnnona muricata

Sample IC50 (μgmL)lowast H2O2 scavengedlowastlowast

Pulp essential oil 5120plusmn 51 2438plusmn 021Leaf essential oil 2448plusmn 32 3180plusmn 051Ascorbic acid 213plusmn 32 NDGallic acid ND 9500plusmn 112lowastlowastlowastlowastIC50 concentration of extract required to scavenge 50 of DPPH radicalslowastlowast H2O2 scavenged was determined at 1mgmL for essential oils lowastlowastlowastForgallic acid H2O2 scavenged was determined at 50 μgmL

6 Biochemistry Research International

In the DPPH radical scavenging assay a dose-dependentinhibition of the DPPH radical was observed in essential oiland standard ascorbic acid treatments e IC50 valuesobtained for the leaf and fruit pulp essential oils indicate agood inhibition of the DPPH radical In the hydrogenperoxide scavenging assay the leaf essential oil showedsuperior activity to the pulp essential oil e activity of bothessential oils could however be described as average as thepercent inhibition of hydrogen peroxide was less than 50for both oils

Both essential oils however displayed very good totalantioxidant activity as seen in Table 3 Both oils had highlevels of phenolic content and this may have contributed tothe antioxidant activities observed It has been postulatedthat phenolic compounds possess high reactivity towardsperoxyl radicals via a formal hydrogen atom transfer andthis is the basis of their antioxidant activity [18 51] Phenoliccompounds are therefore categorized as chain breaking

antioxidants [52] Many reports on the antioxidant potentialof essential oils exist [13] and this report further confirmsthe importance of essential oils as antioxidative agents Sincereactive oxygen species cause serious damage to nucleicacids proteins and lipids the impressive antioxidant ac-tivity of the essential oils from Annona muricata suggestspossible use as natural antioxidant source in food additivesand animal feed formulation

5 Conclusion

Sesquiterpenes were the major constituents of the leaf es-sential oils of Annona muricata from Ghana whereas thefruit pulp essential oil consisted of aliphatic compounds andsterols e most abundant compound in leaf essential oilwas δ-cadinene In the fruit pulp essential oil Ccedil-sitosterolwas most abundant Both essential oils displayed promisingantioxidant activities and suggests potential application in

Table 5 Comparison of leaf and fruit pulp essential oil composition from different studies

Source Location Constituents ( composition)Leaves

Present findings Ghana

δ-Cadinene (2258) α-muurolene (1064)andrographolide (651) τ-cadinol (647) ledene

oxide (II) (629) α-cadinol (565) β-caryophyllene(557)

[33] Cote drsquoIvoireβ-Caryophyllene (314) δ-cadinene (67)

α-muurolene (55) (E)-2-hexenol (48) τ-cadinol(43)

[29] Beninβ-Caryophyllene (136) δ-cadinene (91) epi-

α-cadinol (84) α-cadinol (83) isocaryophyllene(75)

[32] Nigeria (E)-Caryophyllene (389) eugenol (302) δ-cadinene(60) caryophyllene oxide (50) α-humulene (43)

[35] Vietnam β-Pinene (206) germacrene D (181) p-mentha-24(8)-diene (98) α-pinene (94) β-elemene (91)

[27] Cameroon β-Caryophyllene (40) β-elemene (144) α-santalene(95) (Z)-hex-3-enol (52) δ-cardinene (48)

[26] Egypt Bicycloelemene (236) limonene (166) β-pinene(143) α-fenchene (66) α-pinene (54)

Fruit pulp

Present findings Ghana

Ccedil-Sitosterol (1982) 2-hydroxy-1-(hydroxymethyl)ethyl ester (1348) 2-hexenoic acid methyl ester(1027) 2-propenoic acid 3-phenyl- methyl ester

(867) Υ-sitosterol (496)

[36] MalaysiaMethyl (E)-2-butenoate (1970) Methyl (E)-2-hexenoate (1840) (Z)-3-hexenol (97) linalool

(930) methyl 2-hydroxyhexanoate (52)

[33] Cote drsquoIvoire

Methyl (E)-2-hexenoate (398) 3-pyridinocarbonylhydrazide (78) methyl hexanoate

(54) methyl (E)-2-butenoate (48) 23-dihydrobenzofuran (45)

[34] CubaMethyl 3-phenyl-2-propenoate (106) hexadecanoicacid (97) methyl (E)-2-hexenoate (88) methyl 2-

hydroxy-4-methylvalerate (72) linalool (29)

[30] Sri LankaMethyl hexanoate (3095) methyl (E)-hex-2-enoate(2670) trans-β-farnesene (645) dichloromethane

(572) methyl but-2-enoate (475)

[28] Cameroon2-Hexenoic acid methyl ester (239) β-caryophyllene(127) 18-cineole (99) 2-hexenoic acid ethyl ester

(86) linalool (78)

Biochemistry Research International 7

food processing and preservation as well as cosmetic andpharmaceutical industries

Data Availability

All data generated or analyzed during this study are includedin this published article

Conflicts of Interest

All authors declare no competing financial professional orpersonal interests that might have influenced the perfor-mance or presentation of this work

Authorsrsquo Contributions

LSB conceived the study LSB JNG and RO designed allexperiments LSB JNG and RO collected the samples JNGand RO carried out all the experiments LSB JNG and ROperformed the data analysis JNG drafted and LSB edited theinitial manuscript All authors read and approved the finalmanuscript JNG and RO contributed equally to this work

Acknowledgments

e authors are grateful to the Department of Chemistry andthe KNUST Central Laboratory for the use of their facilitiesfor this study e authors acknowledge Miss Judith Ananeof KNUST for technical support

References

[1] Y-Z Fang S Yang and G Wu ldquoFree radicals antioxidantsand nutritionrdquo Nutrition vol 18 no 10 pp 872ndash879 2002

[2] L Lyras N J Cairns A Jenner J Peter and B Halliwell ldquoAnassessment of oxidative damage to proteins lipids and DNAin brain from patients with Alzheimerrsquos diseaserdquo Journal ofNeurochemistry vol 68 no 5 pp 2061ndash2069 1997

[3] L J Machlin and A Bendich ldquoFree radical tissue damageprotective role of antioxidant nutrientsrdquo FASEB Journalvol 1 no 6 pp 441ndash445 1987

[4] B Halliwell ldquoLipid peroxidation antioxidants and cardio-vascular disease how should we move forwardrdquo Cardio-vascular Research vol 47 no 3 pp 410ndash418 2000

[5] P Poprac K Jomova M Simunkova V Kollar C J Rhodesand M Valko ldquoTargeting free radicals in oxidative stress-related human diseasesrdquo Trends in Pharmacological Sciencesvol 38 no 7 pp 592ndash607 2017

[6] K Yagi ldquoLipid peroxides and human diseasesrdquo Chemistry andPhysics of Lipids vol 45 no 2ndash4 pp 337ndash351 1987

[7] K H S Farvin and C Jacobsen ldquoPhenolic compounds andantioxidant activities of selected species of seaweeds fromDanish coastrdquo Food Chemistry vol 138 no 2-3 pp 1670ndash1681 2013

[8] E R Sherwin ldquoAntioxidantsrdquo Food Additives vol 139ndash1931990

[9] R S Lanigan and T A Yamarik ldquoFinal report on the safetyassessment of BHT (1)rdquo International Journal of Toxicologyvol 21 pp 19ndash94 2002

[10] R C Lindenschmidt A F Tryka M E Goad andH P Witschi ldquoe effects of dietary butylated hydrox-ytoluene on liver and colon tumor development in micerdquoToxicology vol 38 no 2 pp 151ndash160 1986

[11] Y He and F Shahidi ldquoAntioxidant activity of green tea and itscatechins in a fish meat model systemrdquo Journal of Agriculturaland Food Chemistry vol 45 no 11 pp 4262ndash4266 1997

[12] C Jacobsen M B Let N S Nielsen and A S MeyerldquoAntioxidant strategies for preventing oxidative flavour de-terioration of foods enriched with N-3 polyunsaturated lipidsa comparative evaluationrdquo Trends in Food Science amp Tech-nology vol 19 no 2 pp 76ndash93 2008

[13] A K Dhakad V V Pandey S Beg J M Rawat and A SinghldquoBiological medicinal and toxicological significance of Eu-calyptus leaf essential oil a reviewrdquo Journal of the Science ofFood and Agriculture vol 98 no 3 pp 833ndash848 2018

[14] M G Miguel ldquoAntioxidant and anti-inflammatory activitiesof essential oils a short reviewrdquo Molecules vol 15 no 12pp 9252ndash9287 2010

[15] P Rubiolo B Sgorbini E Liberto C Cordero and C BicchildquoEssential oils and volatiles sample preparation and analysisA reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 282ndash290 2010

[16] K Husnu Can Baser and G BuchbauerHandbook of EssentialOils Science Technology and Applications CRC Press BocaRaton FL USA 2015

[17] H S Elshafie and I Camele ldquoAn overview of the biologicaleffects of somemediterranean essential oils on human healthrdquoBioMed Research International vol 2017 Article ID 926846814 pages 2017

[18] R Amorati M C Foti and L Valgimigli ldquoAntioxidant ac-tivity of essential oilsrdquo Journal of Agricultural and FoodChemistry vol 61 no 46 pp 10835ndash10847 2013

[19] J R Calo P G Crandall C A OrsquoBryan and S C RickeldquoEssential oils as antimicrobials in food systems-a reviewrdquoFood Control vol 54 pp 111ndash119 2015

[20] M K Swamy M S Akhtar and U Rani Sinniah ldquoAntimi-crobial properties of plant essential oils against humanpathogens and their mode of action an updated reviewrdquoEvidence-Based Complementary and Alternative Medicinevol 2016 Article ID 3012462 21 pages 2016

[21] R Perez-Roses E Risco R Vila P Pentildealver andS Cantildeigueral ldquoBiological and nonbiological antioxidant ac-tivity of some essential oilsrdquo Journal of Agricultural and FoodChemistry vol 64 no 23 pp 4716ndash4724 2016

[22] A V Coria-Tellez E Montalvo-Gonzalez E M Yahia andE N Obledo-Vazquez ldquoAnnona muricata a comprehensivereview on its traditional medicinal uses phytochemicalspharmacological activities mechanisms of action and toxic-ityrdquo Arabian Journal of Chemistry vol 11 no 5 pp 662ndash6912018

[23] S Moghadamtousi M Fadaeinasab S Nikzad G MohanH Ali and H Kadir ldquoAnnona muricata (Annonaceae) areview of its traditional uses isolated acetogenins and bi-ological activitiesrdquo International Journal of Molecular Sci-ences vol 16 no 7 pp 15625ndash15658 2015

[24] P Champy A Melot V Guerineau Eng et al ldquoQuantificationof acetogenins in Annona muricata linked to atypical par-kinsonism in guadelouperdquo Movement Disorders vol 20no 12 pp 1629ndash1633 2005

[25] K W Cheong C P Tan H Mirhosseini N S A HamidA Osman and M Basri ldquoEquilibrium headspace analysis ofvolatile flavor compounds extracted from soursop (Annonamuricata) using solid-phase microextractionrdquo Food ResearchInternational vol 43 no 5 pp 1267ndash1276 2010

[26] S S Elhawary M E E Tantawy M A Rabeh and E F NohaldquoDNA fingerprinting chemical composition antitumor andantimicrobial activities of the essential oils and extractives of

8 Biochemistry Research International

four Annona species from Egyptrdquo Journal of Natural SciencesResearch vol 3 no 59ndash68 p 11 2013

[27] F Fekam Boyom P H Amvam Zollo C Menut G Lamatyand J M Bessiere ldquoAromatic plants of tropical central AfricaPart XXVII Comparative study of the volatile constituents offive annonaceae species growing in Cameroonrdquo Flavour andFragrance Journal vol 11 no 6 pp 333ndash338 1996

[28] L Jirovetz G Buchbauer and M B Ngassoum ldquoEssential oilcompounds of the Annona muricata fresh fruit pulp fromCameroonrdquo Journal of Agricultural and Food Chemistryvol 46 no 9 pp 3719-3720 1998

[29] C Kossouoh M Moudachirou V Adjakidje J-C Chalchatand G Figueredo ldquoEssential oil chemical composition ofAnnona muricata L Leaves from Beninrdquo Journal of EssentialOil Research vol 19 no 4 pp 307ndash309 2007

[30] A J MacLeod and N M Pieris ldquoVolatile flavor componentsof soursop (Annona muricata)rdquo Journal of Agricultural andFood Chemistry vol 29 no 3 pp 488ndash490 1981

[31] C Marquez J Carlos A M Jimenez C Osorio R Jose andV Cartagena ldquoVolatile compounds during the ripening ofColombian soursop (Annona muricata L Cv Elita)rdquo Vitaevol 18 no 3 pp 245ndash250 2011

[32] M S Owolabi A Lanre Ogundajo N S Dosoky andW N Setzer ldquoe cytotoxic activity of Annona muricata leafoil from badagary NigeriardquoAmerican Journal of Essential Oilsand Natural Products vol 1 pp 1ndash3 2013

[33] Y Pelissier C Marion D Kone G Lamaty C Menut andJ-M Bessiere ldquoVolatile components of Annona muricata LrdquoJournal of Essential Oil Research vol 6 no 4 pp 411ndash4141994

[34] J A Pino J Aguero and R Marbot ldquoVolatile components ofsoursop (Annona muricata L)rdquo Journal of Essential Oil Re-search vol 13 no 2 pp 140-141 2001

[35] T D ang D N Dai T M Hoi and I A OgunwandeldquoStudy on the volatile oil contents of Annona glabra LAnnona squamosa L Annona muricata L and Annonareticulata L from Vietnamrdquo Natural Product Researchvol 27 no 13 pp 1232ndash1236 2013

[36] K C Wong and K H Khoo ldquoVolatile components ofMalaysian annona fruitsrdquo Flavour and Fragrance Journalvol 8 no 1 pp 5ndash10 1993

[37] A Wele I Ndoye and M Badiane ldquoFatty acid and essentialoil compositions of the seed oil of five Annona speciesrdquoNigerian Journal of Natural Products and Medicine vol 8no 1 pp 62ndash65 2004

[38] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Vol 456 Allured Pub-lishing Corporation Carol Stream IL USA 2007

[39] J K Patra Se-W Lee Y-S Kwon J Gyu Park andK-H Baek ldquoChemical characterization and antioxidant po-tential of volatile oil from an edible seaweed porphyra tenera(Kjellman 1897)rdquo Chemistry Central Journal vol 11 no 1p 34 2017

[40] P Prieto M Pineda and M Aguilar ldquoSpectrophotometricquantitation of antioxidant capacity through the formation ofa phosphomolybdenum complex specific application to thedetermination of vitamin Erdquo Analytical Biochemistryvol 269 no 2 pp 337ndash341 1999

[41] D Mukhopadhyay P Dasgupta D S Roy et al ldquoA sensitivein vitro spectrophotometric hydrogen peroxide scavengingassay using 110-phenanthrolinerdquo Free Radicals amp Antioxi-dants vol 6 no 1 2016

[42] L S Borquaye G Darko E Ocansey and E AnkomahldquoAntimicrobial and antioxidant properties of the crude

peptide extracts of Galatea paradoxa and Patella rusticardquoSpringerPlus vol 4 no 1 p 500 2015

[43] L S Borquaye G Darko N Oklu C Anson-Yevu andA Ababio ldquoAntimicrobial and antioxidant activities of ethylacetate and methanol extracts of Littorina littorea andGalateaparadoxardquo Cogent Chemistry vol 2 no 1 article 11618652016

[44] L Peng Y Kawagoe P Hogan and D Delmer ldquoSitosterol-beta- glucoside as primer for cellulose synthesis in plantsrdquoScience vol 295 no 5552 pp 147ndash150 2002

[45] A I Hussain F Anwar S T Hussain Sherazi andR Przybylski ldquoChemical composition antioxidant and an-timicrobial activities of basil (Ocimum basilicum) essential oilsdepends on seasonal variationsrdquo Food Chemistry vol 108no 3 pp 986ndash995 2008

[46] P C Santos-Gomes and M Fernandes-Ferreira ldquoOrgan- andseason-dependent variation in the essential oil composition ofSalvia officinalis L Cultivated at two different sitesrdquo Journal ofAgricultural and Food Chemistry vol 49 no 6 pp 2908ndash2916 2001

[47] W Aidi Wannes B Mhamdi B Marzouk and B MarzoukldquoVariations in essential oil and fatty acid composition duringMyrtus communis var italica fruit maturationrdquo FoodChemistry vol 112 no 3 pp 621ndash626 2009

[48] M Hudaib E Speroni A M Di Pietra and V Cavrini ldquoGCMS evaluation of thyme (Dymus vulgaris L) oil compositionand variations during the vegetative cyclerdquo Journal ofPharmaceutical and Biomedical Analysis vol 29 no 4pp 691ndash700 2002

[49] A M Viljoen S Subramoney S F v Vuuren K H C Baserand B Demirci ldquoe composition geographical variation andantimicrobial activity of Lippia javanica (verbenaceae) leafessential oilsrdquo Journal of Ethnopharmacology vol 96 no 1-2pp 271ndash277 2005

[50] C Demirci and A Studer Encyclopedia of Radicals inChemistry Biology and Materials Vol 2 John Wiley amp SonsChichester UK 2012

[51] M C Foti ldquoAntioxidant properties of phenolsrdquo Journal ofPharmacy and Pharmacology vol 59 no 12 pp 1673ndash16852007

[52] G W Burton T Doba E Gabe et al ldquoAutoxidation of bi-ological molecules 4 Maximizing the antioxidant activity ofphenolsrdquo Journal of the American Chemical Society vol 107no 24 pp 7053ndash7065 1985

Biochemistry Research International 9

Hindawiwwwhindawicom

International Journal of

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Zoology

Hindawiwwwhindawicom Volume 2018

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PeptidesInternational Journal of

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GenomicsInternational Journal of

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Hindawi Publishing Corporation httpwwwhindawicom Volume 2013Hindawiwwwhindawicom

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Submit your manuscripts atwwwhindawicom

present in the leaf essential oil Gitoxigenin a phytosterolwas also present D-limonene and α-pinene both mono-terpenes were also identified in the leaf essential oilα-pinene was present in the lowest concentration makingup only 004 of the total composition

e essential oil from the fruit pulp was made up ofmainly aliphatic compounds and phytosterols e mostabundant compound was the phytosterol ς-sitosterol whichmade up 1982 of the essential oil Aliphatic compoundslike 2-hydroxy-1-(hydroxymethyl) ethyl ester (1348) 2-hexenoic acid methyl ester (1027) 2-propenoic acid 3-phenyl- methyl ester (867) and 9-octadecanoic acid

(459) were also present in high amounts Terpene com-pounds identified in the essential oil were squalene (a tri-terpene) and the sesquiterpenes 45-di-epi-aristolocheneand β-guaiene Other phytosterols present were α-sitosterol(304) c-sitosterol (496) and campesterol (219) Anumber of straight-chain alkanes such as nonane dodecaneand tridecane were also present in varying amounts Phe-nylacetaldehyde was the only aldehyde identified in theessential oil from the fruit pulp of Annona muricata

e antioxidant activities of the essential oils were de-termined using the phosphomolybdenum assay and DPPHand H2O2 scavenging assays e total phenolic content of

2-Hexenoic acid methyl ester

O

O

Ccedil-Sitosterol

oleyl oleate

O

O

425 625 825 1025 1225 1425 1625 1825 2025 2225 2425 2625 2825 3025 3225 3425 3625Time

3825 4025 4225 4425 4625 4825

100

0

() 774

696

811 1002 1112 11581305

1431

1483

1605 2054

2226 2293 2345

2682 2845 29813063

31633266

32442373

2508

2598

HO

CH3

CH3

CH3

CH3H3C

H3C

H

H H

H

2-Propenic acid 3-phenylmethyl ester

Figure 1 GC-MS spectra of the fruit pulp essential oil of Annona muricata and the chemical structure of some of the constituents

α-Copaene

α-Muurolene

δ-Cadinene

6-epi-Shyobunol

τ-Cadinol

HO

OH

H

HH

H

Figure 2 GC-MS spectra of the leaf essential oil of Annona muricata and the chemical structure of some of the constituents

4 Biochemistry Research International

the oils was also determined e total antioxidant capacityas determined from the phosphomolybdenum assay was4903 gAAE100 g and 5088 gAAE100 g for fruit pulp andleaf essential oils respectively (Table 3) ere was no sig-nificant difference (Plt 005) between the antioxidant ca-pacities of both the leaf and fruit pulp essential oils e leafessential oil proved to be a better scavenger of the DPPHradical than the fruit pulp essential oil e IC50 for the leafessential oil was 2448plusmn 32 μgmL whereas that for the fruitpulp was 512plusmn 51 μgmL (Table 4) At 10mgmL the fruitpulp essential oil scavenged about 24 of H2O2 while the leafessential oil scavenged about 32 of H2O2 at 1mgmL

(Table 4) e leaf essential oil thus proved to be a betterH2O2 scavenger than the fruit pulp essential oil In terms ofphenolic content there were more phenolic compounds inthe leaf essential oil than there was in the fruit pulp essentialoil (Table 3)

4 Discussions

e yield of the essential oils obtained in this work was in asimilar range to that obtained from Annona muricata byother researchers In general essential oil yields are less than1 e fruit pulp produced a slighter higher yield than theleaves in this study Different plant organs produce differentamountslevels of essential oils and this usually reflects thefunction of the oils in that plant organ

e leaf essential oils were mainly terpenes whereas thepulp essential oils were made up of aliphatic compounds andsterols similar to other results in the literature [28ndash30 33]e most abundant component of the leaf essential oil wasδ-cadinene is compound has been identified in the leafessential oils of Annona muricata from other locations asshown in Table 5 [27 29 32 33] Other works on the leafessential oils of Annona muricata (Table 5) showed thatβ-caryophyllene was the major constituent [27 29 33] Eventhough present in the leaf essential oil from Ghanaβ-caryophyllene was not the most abundant constituentOther sesquiterpenes and terpenoids such α-muuroleneτ-cadinol α-cadinol and α-humulene present were com-mon to this study and results from other works (Table 5)

For the fruit pulp essential oils Ccedil-sitosterol a plant ste-roidal hormone necessary for some physiological processessuch as cell elongation and cellulose biosynthesis [44] wasidentified as the most abundant component Campesterolanother phytosterol with similar functions as sitosterol wasalso identified in the fruit essential oils In general howevermajority of the components identified in the fruit essential oilswere aliphatic compoundsmade up of esters alkanes alcoholsaldehydes and fatty acids 2-Hexenoic acid methyl ester (ormethyl-2-hexenoate) which was present in this study as the 2nd

most abundant constituent was present in the pulp essentialoils from other locations [28 30 33 34] e levels werehowever different Variations in essential oil composition fromthe same plant organ may be due to a variety of factorsSeasonal variations in chemical composition of essential oilshave been reported in the literature is difference inchemical composition due to seasonal variations has beenobserved to affect the bioactivity of the essential oils as well[45 46] Other reasons for differences in the chemical com-position of essential oils from the same plant organ includeenvironmental and genetic factors geographical variationschemotypic diversity plant maturation stage and nutritionalstatus of the plant [46ndash49] us two plants of the samespecies but different chemotypes will produce essential oilswith variations in chemical composition e differences inessential oil compositions of Annona muricata leaf and fruitpulp in this and other works may be attributed to one or anycombination of these elements

e antioxidant potential of the leaf and fruit pulp es-sential oils as evaluated from the phosphomolybdenum

Table 1 Composition of leaf essential oil of Annona muricata asdetermined by GC-MS with tentative identified compounds

No RT SI Compound composition1 716 87 α-Pinene (D)- 0042 887 96 Limonene (D)- 025

3 1159 98 Methyl (9E)-9-octadecen-12-ynoate 036

4 1306 89 6-Methyloctadecane 0215 1362 90 δ-EIemene 1046 1421 98 α-Copaene 4217 1439 99 β-Elemene 0188 1465 95 α-Muurolene 10649 1465 91 Andrographolide 65110 1484 98 Ledene oxide (II) 62911 1484 98 β-Caryophyllene 55712 1508 92 α-Acorenol 00613 1514 83 β-cis-farnesene 27214 1530 97 α-Humulene 14415 1537 97 c-Muurolene 02116 1552 98 α-Selinene 11317 1574 91 4-epi-cubedol 08818 1601 96 Caryophyllene oxide 11519 1609 97 δ-Cadinene 225820 1680 97 Cubenol 194

21 1691 94 2-Hexadecen-1-ol 371115-tetramethyl 039

22 1775 97 α-Cadinol 565

23 1930 96 Methyl 1012-pentacosadiynoate 199

24 1963 88 β-Viternene 02525 1973 91 Cedren-13-ol 01226 2007 95 Gitoxigenin 137

27 2014 96 16-Octadecenoic acid methylester 026

28 2026 95 3-(Octadecyloxy) propyl ester 55729 2235 94 6-epi-shyobunol 51730 2557 99 τ-Cadinol 64731 2727 90 Octadecane 533

Terpenes 5026Oxygenated terpenes

(terpenoids) 3424

Esters 818Alkanes 554Sterol 137Alcohol 039Total 9998

No compound number in order of elution SI Similarity Index (librarysearch of purity value of a compound) RT retention time in minutes

Biochemistry Research International 5

DPPH scavenging and hydrogen peroxide assays revealedpromising antioxidant properties (Tables 3 and 4) emechanism of antioxidant activity includes prevention of theformation of the initiator radical and termination of radicalsin the chain propagation stage or via indirect routes such asenhancement of the activities of enzymes that mop up

reactive species or induction in the expression of theseenzymes [18 50] Because essential oils consist of a numberof different compounds the antioxidant activity observed isusually the synergistic effect of the various constituents [18]

Table 2 Composition of fruit pulp essential oil of Annona muricata as determined by GC-MS with tentative identified compounds

No RT SI Compound composition1 651 80 Nonane 1742 696 98 Hexanoic acid methyl ester 1863 774 96 2-Hexenoic acid methyl ester 10274 811 94 Pentanoic acid 2-hydroxy-4-methyl- methyl ester 0035 818 98 Pentanoic acid 2-hydroxy-3-methyl- methyl ester 0426 935 94 268-Trimethylbicyclo[420]oct-2-ene-18-diol 0237 1002 99 16-Octadien-3-ol 37-dimethyl- 0138 1112 94 2-Octenoic acid methyl ester (E)- 0489 1158 92 Dodecane 05910 1200 94 Phenylacetaldehyde 17111 1305 91 Tridecane 04312 1431 97 2-Propenoic acid 3-phenyl- methyl ester 86713 1483 98 β-Caryophyllene 17714 1530 96 45-di-epi-Aristolochene 03515 1572 93 Falcarinol 01816 1605 99 β-Guaiene 01717 2054 94 Hexadecanoic acid methyl ester 03318 2226 94 Glyceryl 2-laurate 15219 2231 99 9-Octadecenoic acid methyl ester (E)- 21820 2507 97 8-Octadecanoic acid 22021 2508 99 2-Hydroxy-1-(hydroxymethyl) ethyl ester 134822 2558 96 Ccedil-Sitosterol 198223 2644 94 9-Octadecanoic acid 45924 2644 96 Pentadecanoic acid 13-methyl- methyl ester 04225 2693 80 23-Dihydroxypropyl elaidate 38126 2702 96 Squalene 17427 2728 97 α-Sitosterol 30428 2728 99 Oleic acid 20029 2763 87 Octadecane 20330 2981 91 Campesterol 21931 3062 96 Υ-Sitosterol 49632 3244 99 Oleyl oleate 25333 3265 86 Nonadecatriene-514-diol 412

Esters 4600Sterols 3001Terpenes 403Alcohols 466Alkanes 479Aldehyde 171

Carboxylic acid 879Total 9999

No compound number in order of elution SI Similarity Index (library search of purity value of a compound) RT retention time in minutes

Table 3 Total antioxidant capacity (TAC) and total phenoliccontent (TPC) of fruit pulp and leaf essential oils

Sample TAClowast gAAE100 g TPClowastlowast gGAE100 gPulp essential oil 4903plusmn 048a 398plusmn 060bLeaf essential oil 5088plusmn 050a 438plusmn 042b

Columns with different letters indicate significant difference (Plt 005Sidakrsquos multiple comparison test) lowastTAC expressed in gram ascorbic acidequivalent per 100 g of sample (gAAE100 g) lowastlowastTPC expressed in gramgallic acid equivalent per 100 g of sample (gGAE100 g)

Table 4 DPPH free radical and hydrogen peroxide scavengingactivities of essential oils and hydrosols from leaf and fruit pulp ofAnnona muricata

Sample IC50 (μgmL)lowast H2O2 scavengedlowastlowast

Pulp essential oil 5120plusmn 51 2438plusmn 021Leaf essential oil 2448plusmn 32 3180plusmn 051Ascorbic acid 213plusmn 32 NDGallic acid ND 9500plusmn 112lowastlowastlowastlowastIC50 concentration of extract required to scavenge 50 of DPPH radicalslowastlowast H2O2 scavenged was determined at 1mgmL for essential oils lowastlowastlowastForgallic acid H2O2 scavenged was determined at 50 μgmL

6 Biochemistry Research International

In the DPPH radical scavenging assay a dose-dependentinhibition of the DPPH radical was observed in essential oiland standard ascorbic acid treatments e IC50 valuesobtained for the leaf and fruit pulp essential oils indicate agood inhibition of the DPPH radical In the hydrogenperoxide scavenging assay the leaf essential oil showedsuperior activity to the pulp essential oil e activity of bothessential oils could however be described as average as thepercent inhibition of hydrogen peroxide was less than 50for both oils

Both essential oils however displayed very good totalantioxidant activity as seen in Table 3 Both oils had highlevels of phenolic content and this may have contributed tothe antioxidant activities observed It has been postulatedthat phenolic compounds possess high reactivity towardsperoxyl radicals via a formal hydrogen atom transfer andthis is the basis of their antioxidant activity [18 51] Phenoliccompounds are therefore categorized as chain breaking

antioxidants [52] Many reports on the antioxidant potentialof essential oils exist [13] and this report further confirmsthe importance of essential oils as antioxidative agents Sincereactive oxygen species cause serious damage to nucleicacids proteins and lipids the impressive antioxidant ac-tivity of the essential oils from Annona muricata suggestspossible use as natural antioxidant source in food additivesand animal feed formulation

5 Conclusion

Sesquiterpenes were the major constituents of the leaf es-sential oils of Annona muricata from Ghana whereas thefruit pulp essential oil consisted of aliphatic compounds andsterols e most abundant compound in leaf essential oilwas δ-cadinene In the fruit pulp essential oil Ccedil-sitosterolwas most abundant Both essential oils displayed promisingantioxidant activities and suggests potential application in

Table 5 Comparison of leaf and fruit pulp essential oil composition from different studies

Source Location Constituents ( composition)Leaves

Present findings Ghana

δ-Cadinene (2258) α-muurolene (1064)andrographolide (651) τ-cadinol (647) ledene

oxide (II) (629) α-cadinol (565) β-caryophyllene(557)

[33] Cote drsquoIvoireβ-Caryophyllene (314) δ-cadinene (67)

α-muurolene (55) (E)-2-hexenol (48) τ-cadinol(43)

[29] Beninβ-Caryophyllene (136) δ-cadinene (91) epi-

α-cadinol (84) α-cadinol (83) isocaryophyllene(75)

[32] Nigeria (E)-Caryophyllene (389) eugenol (302) δ-cadinene(60) caryophyllene oxide (50) α-humulene (43)

[35] Vietnam β-Pinene (206) germacrene D (181) p-mentha-24(8)-diene (98) α-pinene (94) β-elemene (91)

[27] Cameroon β-Caryophyllene (40) β-elemene (144) α-santalene(95) (Z)-hex-3-enol (52) δ-cardinene (48)

[26] Egypt Bicycloelemene (236) limonene (166) β-pinene(143) α-fenchene (66) α-pinene (54)

Fruit pulp

Present findings Ghana

Ccedil-Sitosterol (1982) 2-hydroxy-1-(hydroxymethyl)ethyl ester (1348) 2-hexenoic acid methyl ester(1027) 2-propenoic acid 3-phenyl- methyl ester

(867) Υ-sitosterol (496)

[36] MalaysiaMethyl (E)-2-butenoate (1970) Methyl (E)-2-hexenoate (1840) (Z)-3-hexenol (97) linalool

(930) methyl 2-hydroxyhexanoate (52)

[33] Cote drsquoIvoire

Methyl (E)-2-hexenoate (398) 3-pyridinocarbonylhydrazide (78) methyl hexanoate

(54) methyl (E)-2-butenoate (48) 23-dihydrobenzofuran (45)

[34] CubaMethyl 3-phenyl-2-propenoate (106) hexadecanoicacid (97) methyl (E)-2-hexenoate (88) methyl 2-

hydroxy-4-methylvalerate (72) linalool (29)

[30] Sri LankaMethyl hexanoate (3095) methyl (E)-hex-2-enoate(2670) trans-β-farnesene (645) dichloromethane

(572) methyl but-2-enoate (475)

[28] Cameroon2-Hexenoic acid methyl ester (239) β-caryophyllene(127) 18-cineole (99) 2-hexenoic acid ethyl ester

(86) linalool (78)

Biochemistry Research International 7

food processing and preservation as well as cosmetic andpharmaceutical industries

Data Availability

All data generated or analyzed during this study are includedin this published article

Conflicts of Interest

All authors declare no competing financial professional orpersonal interests that might have influenced the perfor-mance or presentation of this work

Authorsrsquo Contributions

LSB conceived the study LSB JNG and RO designed allexperiments LSB JNG and RO collected the samples JNGand RO carried out all the experiments LSB JNG and ROperformed the data analysis JNG drafted and LSB edited theinitial manuscript All authors read and approved the finalmanuscript JNG and RO contributed equally to this work

Acknowledgments

e authors are grateful to the Department of Chemistry andthe KNUST Central Laboratory for the use of their facilitiesfor this study e authors acknowledge Miss Judith Ananeof KNUST for technical support

References

[1] Y-Z Fang S Yang and G Wu ldquoFree radicals antioxidantsand nutritionrdquo Nutrition vol 18 no 10 pp 872ndash879 2002

[2] L Lyras N J Cairns A Jenner J Peter and B Halliwell ldquoAnassessment of oxidative damage to proteins lipids and DNAin brain from patients with Alzheimerrsquos diseaserdquo Journal ofNeurochemistry vol 68 no 5 pp 2061ndash2069 1997

[3] L J Machlin and A Bendich ldquoFree radical tissue damageprotective role of antioxidant nutrientsrdquo FASEB Journalvol 1 no 6 pp 441ndash445 1987

[4] B Halliwell ldquoLipid peroxidation antioxidants and cardio-vascular disease how should we move forwardrdquo Cardio-vascular Research vol 47 no 3 pp 410ndash418 2000

[5] P Poprac K Jomova M Simunkova V Kollar C J Rhodesand M Valko ldquoTargeting free radicals in oxidative stress-related human diseasesrdquo Trends in Pharmacological Sciencesvol 38 no 7 pp 592ndash607 2017

[6] K Yagi ldquoLipid peroxides and human diseasesrdquo Chemistry andPhysics of Lipids vol 45 no 2ndash4 pp 337ndash351 1987

[7] K H S Farvin and C Jacobsen ldquoPhenolic compounds andantioxidant activities of selected species of seaweeds fromDanish coastrdquo Food Chemistry vol 138 no 2-3 pp 1670ndash1681 2013

[8] E R Sherwin ldquoAntioxidantsrdquo Food Additives vol 139ndash1931990

[9] R S Lanigan and T A Yamarik ldquoFinal report on the safetyassessment of BHT (1)rdquo International Journal of Toxicologyvol 21 pp 19ndash94 2002

[10] R C Lindenschmidt A F Tryka M E Goad andH P Witschi ldquoe effects of dietary butylated hydrox-ytoluene on liver and colon tumor development in micerdquoToxicology vol 38 no 2 pp 151ndash160 1986

[11] Y He and F Shahidi ldquoAntioxidant activity of green tea and itscatechins in a fish meat model systemrdquo Journal of Agriculturaland Food Chemistry vol 45 no 11 pp 4262ndash4266 1997

[12] C Jacobsen M B Let N S Nielsen and A S MeyerldquoAntioxidant strategies for preventing oxidative flavour de-terioration of foods enriched with N-3 polyunsaturated lipidsa comparative evaluationrdquo Trends in Food Science amp Tech-nology vol 19 no 2 pp 76ndash93 2008

[13] A K Dhakad V V Pandey S Beg J M Rawat and A SinghldquoBiological medicinal and toxicological significance of Eu-calyptus leaf essential oil a reviewrdquo Journal of the Science ofFood and Agriculture vol 98 no 3 pp 833ndash848 2018

[14] M G Miguel ldquoAntioxidant and anti-inflammatory activitiesof essential oils a short reviewrdquo Molecules vol 15 no 12pp 9252ndash9287 2010

[15] P Rubiolo B Sgorbini E Liberto C Cordero and C BicchildquoEssential oils and volatiles sample preparation and analysisA reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 282ndash290 2010

[16] K Husnu Can Baser and G BuchbauerHandbook of EssentialOils Science Technology and Applications CRC Press BocaRaton FL USA 2015

[17] H S Elshafie and I Camele ldquoAn overview of the biologicaleffects of somemediterranean essential oils on human healthrdquoBioMed Research International vol 2017 Article ID 926846814 pages 2017

[18] R Amorati M C Foti and L Valgimigli ldquoAntioxidant ac-tivity of essential oilsrdquo Journal of Agricultural and FoodChemistry vol 61 no 46 pp 10835ndash10847 2013

[19] J R Calo P G Crandall C A OrsquoBryan and S C RickeldquoEssential oils as antimicrobials in food systems-a reviewrdquoFood Control vol 54 pp 111ndash119 2015

[20] M K Swamy M S Akhtar and U Rani Sinniah ldquoAntimi-crobial properties of plant essential oils against humanpathogens and their mode of action an updated reviewrdquoEvidence-Based Complementary and Alternative Medicinevol 2016 Article ID 3012462 21 pages 2016

[21] R Perez-Roses E Risco R Vila P Pentildealver andS Cantildeigueral ldquoBiological and nonbiological antioxidant ac-tivity of some essential oilsrdquo Journal of Agricultural and FoodChemistry vol 64 no 23 pp 4716ndash4724 2016

[22] A V Coria-Tellez E Montalvo-Gonzalez E M Yahia andE N Obledo-Vazquez ldquoAnnona muricata a comprehensivereview on its traditional medicinal uses phytochemicalspharmacological activities mechanisms of action and toxic-ityrdquo Arabian Journal of Chemistry vol 11 no 5 pp 662ndash6912018

[23] S Moghadamtousi M Fadaeinasab S Nikzad G MohanH Ali and H Kadir ldquoAnnona muricata (Annonaceae) areview of its traditional uses isolated acetogenins and bi-ological activitiesrdquo International Journal of Molecular Sci-ences vol 16 no 7 pp 15625ndash15658 2015

[24] P Champy A Melot V Guerineau Eng et al ldquoQuantificationof acetogenins in Annona muricata linked to atypical par-kinsonism in guadelouperdquo Movement Disorders vol 20no 12 pp 1629ndash1633 2005

[25] K W Cheong C P Tan H Mirhosseini N S A HamidA Osman and M Basri ldquoEquilibrium headspace analysis ofvolatile flavor compounds extracted from soursop (Annonamuricata) using solid-phase microextractionrdquo Food ResearchInternational vol 43 no 5 pp 1267ndash1276 2010

[26] S S Elhawary M E E Tantawy M A Rabeh and E F NohaldquoDNA fingerprinting chemical composition antitumor andantimicrobial activities of the essential oils and extractives of

8 Biochemistry Research International

four Annona species from Egyptrdquo Journal of Natural SciencesResearch vol 3 no 59ndash68 p 11 2013

[27] F Fekam Boyom P H Amvam Zollo C Menut G Lamatyand J M Bessiere ldquoAromatic plants of tropical central AfricaPart XXVII Comparative study of the volatile constituents offive annonaceae species growing in Cameroonrdquo Flavour andFragrance Journal vol 11 no 6 pp 333ndash338 1996

[28] L Jirovetz G Buchbauer and M B Ngassoum ldquoEssential oilcompounds of the Annona muricata fresh fruit pulp fromCameroonrdquo Journal of Agricultural and Food Chemistryvol 46 no 9 pp 3719-3720 1998

[29] C Kossouoh M Moudachirou V Adjakidje J-C Chalchatand G Figueredo ldquoEssential oil chemical composition ofAnnona muricata L Leaves from Beninrdquo Journal of EssentialOil Research vol 19 no 4 pp 307ndash309 2007

[30] A J MacLeod and N M Pieris ldquoVolatile flavor componentsof soursop (Annona muricata)rdquo Journal of Agricultural andFood Chemistry vol 29 no 3 pp 488ndash490 1981

[31] C Marquez J Carlos A M Jimenez C Osorio R Jose andV Cartagena ldquoVolatile compounds during the ripening ofColombian soursop (Annona muricata L Cv Elita)rdquo Vitaevol 18 no 3 pp 245ndash250 2011

[32] M S Owolabi A Lanre Ogundajo N S Dosoky andW N Setzer ldquoe cytotoxic activity of Annona muricata leafoil from badagary NigeriardquoAmerican Journal of Essential Oilsand Natural Products vol 1 pp 1ndash3 2013

[33] Y Pelissier C Marion D Kone G Lamaty C Menut andJ-M Bessiere ldquoVolatile components of Annona muricata LrdquoJournal of Essential Oil Research vol 6 no 4 pp 411ndash4141994

[34] J A Pino J Aguero and R Marbot ldquoVolatile components ofsoursop (Annona muricata L)rdquo Journal of Essential Oil Re-search vol 13 no 2 pp 140-141 2001

[35] T D ang D N Dai T M Hoi and I A OgunwandeldquoStudy on the volatile oil contents of Annona glabra LAnnona squamosa L Annona muricata L and Annonareticulata L from Vietnamrdquo Natural Product Researchvol 27 no 13 pp 1232ndash1236 2013

[36] K C Wong and K H Khoo ldquoVolatile components ofMalaysian annona fruitsrdquo Flavour and Fragrance Journalvol 8 no 1 pp 5ndash10 1993

[37] A Wele I Ndoye and M Badiane ldquoFatty acid and essentialoil compositions of the seed oil of five Annona speciesrdquoNigerian Journal of Natural Products and Medicine vol 8no 1 pp 62ndash65 2004

[38] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Vol 456 Allured Pub-lishing Corporation Carol Stream IL USA 2007

[39] J K Patra Se-W Lee Y-S Kwon J Gyu Park andK-H Baek ldquoChemical characterization and antioxidant po-tential of volatile oil from an edible seaweed porphyra tenera(Kjellman 1897)rdquo Chemistry Central Journal vol 11 no 1p 34 2017

[40] P Prieto M Pineda and M Aguilar ldquoSpectrophotometricquantitation of antioxidant capacity through the formation ofa phosphomolybdenum complex specific application to thedetermination of vitamin Erdquo Analytical Biochemistryvol 269 no 2 pp 337ndash341 1999

[41] D Mukhopadhyay P Dasgupta D S Roy et al ldquoA sensitivein vitro spectrophotometric hydrogen peroxide scavengingassay using 110-phenanthrolinerdquo Free Radicals amp Antioxi-dants vol 6 no 1 2016

[42] L S Borquaye G Darko E Ocansey and E AnkomahldquoAntimicrobial and antioxidant properties of the crude

peptide extracts of Galatea paradoxa and Patella rusticardquoSpringerPlus vol 4 no 1 p 500 2015

[43] L S Borquaye G Darko N Oklu C Anson-Yevu andA Ababio ldquoAntimicrobial and antioxidant activities of ethylacetate and methanol extracts of Littorina littorea andGalateaparadoxardquo Cogent Chemistry vol 2 no 1 article 11618652016

[44] L Peng Y Kawagoe P Hogan and D Delmer ldquoSitosterol-beta- glucoside as primer for cellulose synthesis in plantsrdquoScience vol 295 no 5552 pp 147ndash150 2002

[45] A I Hussain F Anwar S T Hussain Sherazi andR Przybylski ldquoChemical composition antioxidant and an-timicrobial activities of basil (Ocimum basilicum) essential oilsdepends on seasonal variationsrdquo Food Chemistry vol 108no 3 pp 986ndash995 2008

[46] P C Santos-Gomes and M Fernandes-Ferreira ldquoOrgan- andseason-dependent variation in the essential oil composition ofSalvia officinalis L Cultivated at two different sitesrdquo Journal ofAgricultural and Food Chemistry vol 49 no 6 pp 2908ndash2916 2001

[47] W Aidi Wannes B Mhamdi B Marzouk and B MarzoukldquoVariations in essential oil and fatty acid composition duringMyrtus communis var italica fruit maturationrdquo FoodChemistry vol 112 no 3 pp 621ndash626 2009

[48] M Hudaib E Speroni A M Di Pietra and V Cavrini ldquoGCMS evaluation of thyme (Dymus vulgaris L) oil compositionand variations during the vegetative cyclerdquo Journal ofPharmaceutical and Biomedical Analysis vol 29 no 4pp 691ndash700 2002

[49] A M Viljoen S Subramoney S F v Vuuren K H C Baserand B Demirci ldquoe composition geographical variation andantimicrobial activity of Lippia javanica (verbenaceae) leafessential oilsrdquo Journal of Ethnopharmacology vol 96 no 1-2pp 271ndash277 2005

[50] C Demirci and A Studer Encyclopedia of Radicals inChemistry Biology and Materials Vol 2 John Wiley amp SonsChichester UK 2012

[51] M C Foti ldquoAntioxidant properties of phenolsrdquo Journal ofPharmacy and Pharmacology vol 59 no 12 pp 1673ndash16852007

[52] G W Burton T Doba E Gabe et al ldquoAutoxidation of bi-ological molecules 4 Maximizing the antioxidant activity ofphenolsrdquo Journal of the American Chemical Society vol 107no 24 pp 7053ndash7065 1985

Biochemistry Research International 9

Hindawiwwwhindawicom

International Journal of

Volume 2018

Zoology

Hindawiwwwhindawicom Volume 2018

Anatomy Research International

PeptidesInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Journal of Parasitology Research

GenomicsInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawi Publishing Corporation httpwwwhindawicom Volume 2013Hindawiwwwhindawicom

The Scientific World Journal

Volume 2018

Hindawiwwwhindawicom Volume 2018

BioinformaticsAdvances in

Marine BiologyJournal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Neuroscience Journal

Hindawiwwwhindawicom Volume 2018

BioMed Research International

Cell BiologyInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Biochemistry Research International

ArchaeaHindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Genetics Research International

Hindawiwwwhindawicom Volume 2018

Advances in

Virolog y Stem Cells International

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MicrobiologyHindawiwwwhindawicom

Nucleic AcidsJournal of

Volume 2018

Submit your manuscripts atwwwhindawicom

the oils was also determined e total antioxidant capacityas determined from the phosphomolybdenum assay was4903 gAAE100 g and 5088 gAAE100 g for fruit pulp andleaf essential oils respectively (Table 3) ere was no sig-nificant difference (Plt 005) between the antioxidant ca-pacities of both the leaf and fruit pulp essential oils e leafessential oil proved to be a better scavenger of the DPPHradical than the fruit pulp essential oil e IC50 for the leafessential oil was 2448plusmn 32 μgmL whereas that for the fruitpulp was 512plusmn 51 μgmL (Table 4) At 10mgmL the fruitpulp essential oil scavenged about 24 of H2O2 while the leafessential oil scavenged about 32 of H2O2 at 1mgmL

(Table 4) e leaf essential oil thus proved to be a betterH2O2 scavenger than the fruit pulp essential oil In terms ofphenolic content there were more phenolic compounds inthe leaf essential oil than there was in the fruit pulp essentialoil (Table 3)

4 Discussions

e yield of the essential oils obtained in this work was in asimilar range to that obtained from Annona muricata byother researchers In general essential oil yields are less than1 e fruit pulp produced a slighter higher yield than theleaves in this study Different plant organs produce differentamountslevels of essential oils and this usually reflects thefunction of the oils in that plant organ

e leaf essential oils were mainly terpenes whereas thepulp essential oils were made up of aliphatic compounds andsterols similar to other results in the literature [28ndash30 33]e most abundant component of the leaf essential oil wasδ-cadinene is compound has been identified in the leafessential oils of Annona muricata from other locations asshown in Table 5 [27 29 32 33] Other works on the leafessential oils of Annona muricata (Table 5) showed thatβ-caryophyllene was the major constituent [27 29 33] Eventhough present in the leaf essential oil from Ghanaβ-caryophyllene was not the most abundant constituentOther sesquiterpenes and terpenoids such α-muuroleneτ-cadinol α-cadinol and α-humulene present were com-mon to this study and results from other works (Table 5)

For the fruit pulp essential oils Ccedil-sitosterol a plant ste-roidal hormone necessary for some physiological processessuch as cell elongation and cellulose biosynthesis [44] wasidentified as the most abundant component Campesterolanother phytosterol with similar functions as sitosterol wasalso identified in the fruit essential oils In general howevermajority of the components identified in the fruit essential oilswere aliphatic compoundsmade up of esters alkanes alcoholsaldehydes and fatty acids 2-Hexenoic acid methyl ester (ormethyl-2-hexenoate) which was present in this study as the 2nd

most abundant constituent was present in the pulp essentialoils from other locations [28 30 33 34] e levels werehowever different Variations in essential oil composition fromthe same plant organ may be due to a variety of factorsSeasonal variations in chemical composition of essential oilshave been reported in the literature is difference inchemical composition due to seasonal variations has beenobserved to affect the bioactivity of the essential oils as well[45 46] Other reasons for differences in the chemical com-position of essential oils from the same plant organ includeenvironmental and genetic factors geographical variationschemotypic diversity plant maturation stage and nutritionalstatus of the plant [46ndash49] us two plants of the samespecies but different chemotypes will produce essential oilswith variations in chemical composition e differences inessential oil compositions of Annona muricata leaf and fruitpulp in this and other works may be attributed to one or anycombination of these elements

e antioxidant potential of the leaf and fruit pulp es-sential oils as evaluated from the phosphomolybdenum

Table 1 Composition of leaf essential oil of Annona muricata asdetermined by GC-MS with tentative identified compounds

No RT SI Compound composition1 716 87 α-Pinene (D)- 0042 887 96 Limonene (D)- 025

3 1159 98 Methyl (9E)-9-octadecen-12-ynoate 036

4 1306 89 6-Methyloctadecane 0215 1362 90 δ-EIemene 1046 1421 98 α-Copaene 4217 1439 99 β-Elemene 0188 1465 95 α-Muurolene 10649 1465 91 Andrographolide 65110 1484 98 Ledene oxide (II) 62911 1484 98 β-Caryophyllene 55712 1508 92 α-Acorenol 00613 1514 83 β-cis-farnesene 27214 1530 97 α-Humulene 14415 1537 97 c-Muurolene 02116 1552 98 α-Selinene 11317 1574 91 4-epi-cubedol 08818 1601 96 Caryophyllene oxide 11519 1609 97 δ-Cadinene 225820 1680 97 Cubenol 194

21 1691 94 2-Hexadecen-1-ol 371115-tetramethyl 039

22 1775 97 α-Cadinol 565

23 1930 96 Methyl 1012-pentacosadiynoate 199

24 1963 88 β-Viternene 02525 1973 91 Cedren-13-ol 01226 2007 95 Gitoxigenin 137

27 2014 96 16-Octadecenoic acid methylester 026

28 2026 95 3-(Octadecyloxy) propyl ester 55729 2235 94 6-epi-shyobunol 51730 2557 99 τ-Cadinol 64731 2727 90 Octadecane 533

Terpenes 5026Oxygenated terpenes

(terpenoids) 3424

Esters 818Alkanes 554Sterol 137Alcohol 039Total 9998

No compound number in order of elution SI Similarity Index (librarysearch of purity value of a compound) RT retention time in minutes

Biochemistry Research International 5

DPPH scavenging and hydrogen peroxide assays revealedpromising antioxidant properties (Tables 3 and 4) emechanism of antioxidant activity includes prevention of theformation of the initiator radical and termination of radicalsin the chain propagation stage or via indirect routes such asenhancement of the activities of enzymes that mop up

reactive species or induction in the expression of theseenzymes [18 50] Because essential oils consist of a numberof different compounds the antioxidant activity observed isusually the synergistic effect of the various constituents [18]

Table 2 Composition of fruit pulp essential oil of Annona muricata as determined by GC-MS with tentative identified compounds

No RT SI Compound composition1 651 80 Nonane 1742 696 98 Hexanoic acid methyl ester 1863 774 96 2-Hexenoic acid methyl ester 10274 811 94 Pentanoic acid 2-hydroxy-4-methyl- methyl ester 0035 818 98 Pentanoic acid 2-hydroxy-3-methyl- methyl ester 0426 935 94 268-Trimethylbicyclo[420]oct-2-ene-18-diol 0237 1002 99 16-Octadien-3-ol 37-dimethyl- 0138 1112 94 2-Octenoic acid methyl ester (E)- 0489 1158 92 Dodecane 05910 1200 94 Phenylacetaldehyde 17111 1305 91 Tridecane 04312 1431 97 2-Propenoic acid 3-phenyl- methyl ester 86713 1483 98 β-Caryophyllene 17714 1530 96 45-di-epi-Aristolochene 03515 1572 93 Falcarinol 01816 1605 99 β-Guaiene 01717 2054 94 Hexadecanoic acid methyl ester 03318 2226 94 Glyceryl 2-laurate 15219 2231 99 9-Octadecenoic acid methyl ester (E)- 21820 2507 97 8-Octadecanoic acid 22021 2508 99 2-Hydroxy-1-(hydroxymethyl) ethyl ester 134822 2558 96 Ccedil-Sitosterol 198223 2644 94 9-Octadecanoic acid 45924 2644 96 Pentadecanoic acid 13-methyl- methyl ester 04225 2693 80 23-Dihydroxypropyl elaidate 38126 2702 96 Squalene 17427 2728 97 α-Sitosterol 30428 2728 99 Oleic acid 20029 2763 87 Octadecane 20330 2981 91 Campesterol 21931 3062 96 Υ-Sitosterol 49632 3244 99 Oleyl oleate 25333 3265 86 Nonadecatriene-514-diol 412

Esters 4600Sterols 3001Terpenes 403Alcohols 466Alkanes 479Aldehyde 171

Carboxylic acid 879Total 9999

No compound number in order of elution SI Similarity Index (library search of purity value of a compound) RT retention time in minutes

Table 3 Total antioxidant capacity (TAC) and total phenoliccontent (TPC) of fruit pulp and leaf essential oils

Sample TAClowast gAAE100 g TPClowastlowast gGAE100 gPulp essential oil 4903plusmn 048a 398plusmn 060bLeaf essential oil 5088plusmn 050a 438plusmn 042b

Columns with different letters indicate significant difference (Plt 005Sidakrsquos multiple comparison test) lowastTAC expressed in gram ascorbic acidequivalent per 100 g of sample (gAAE100 g) lowastlowastTPC expressed in gramgallic acid equivalent per 100 g of sample (gGAE100 g)

Table 4 DPPH free radical and hydrogen peroxide scavengingactivities of essential oils and hydrosols from leaf and fruit pulp ofAnnona muricata

Sample IC50 (μgmL)lowast H2O2 scavengedlowastlowast

Pulp essential oil 5120plusmn 51 2438plusmn 021Leaf essential oil 2448plusmn 32 3180plusmn 051Ascorbic acid 213plusmn 32 NDGallic acid ND 9500plusmn 112lowastlowastlowastlowastIC50 concentration of extract required to scavenge 50 of DPPH radicalslowastlowast H2O2 scavenged was determined at 1mgmL for essential oils lowastlowastlowastForgallic acid H2O2 scavenged was determined at 50 μgmL

6 Biochemistry Research International

In the DPPH radical scavenging assay a dose-dependentinhibition of the DPPH radical was observed in essential oiland standard ascorbic acid treatments e IC50 valuesobtained for the leaf and fruit pulp essential oils indicate agood inhibition of the DPPH radical In the hydrogenperoxide scavenging assay the leaf essential oil showedsuperior activity to the pulp essential oil e activity of bothessential oils could however be described as average as thepercent inhibition of hydrogen peroxide was less than 50for both oils

Both essential oils however displayed very good totalantioxidant activity as seen in Table 3 Both oils had highlevels of phenolic content and this may have contributed tothe antioxidant activities observed It has been postulatedthat phenolic compounds possess high reactivity towardsperoxyl radicals via a formal hydrogen atom transfer andthis is the basis of their antioxidant activity [18 51] Phenoliccompounds are therefore categorized as chain breaking

antioxidants [52] Many reports on the antioxidant potentialof essential oils exist [13] and this report further confirmsthe importance of essential oils as antioxidative agents Sincereactive oxygen species cause serious damage to nucleicacids proteins and lipids the impressive antioxidant ac-tivity of the essential oils from Annona muricata suggestspossible use as natural antioxidant source in food additivesand animal feed formulation

5 Conclusion

Sesquiterpenes were the major constituents of the leaf es-sential oils of Annona muricata from Ghana whereas thefruit pulp essential oil consisted of aliphatic compounds andsterols e most abundant compound in leaf essential oilwas δ-cadinene In the fruit pulp essential oil Ccedil-sitosterolwas most abundant Both essential oils displayed promisingantioxidant activities and suggests potential application in

Table 5 Comparison of leaf and fruit pulp essential oil composition from different studies

Source Location Constituents ( composition)Leaves

Present findings Ghana

δ-Cadinene (2258) α-muurolene (1064)andrographolide (651) τ-cadinol (647) ledene

oxide (II) (629) α-cadinol (565) β-caryophyllene(557)

[33] Cote drsquoIvoireβ-Caryophyllene (314) δ-cadinene (67)

α-muurolene (55) (E)-2-hexenol (48) τ-cadinol(43)

[29] Beninβ-Caryophyllene (136) δ-cadinene (91) epi-

α-cadinol (84) α-cadinol (83) isocaryophyllene(75)

[32] Nigeria (E)-Caryophyllene (389) eugenol (302) δ-cadinene(60) caryophyllene oxide (50) α-humulene (43)

[35] Vietnam β-Pinene (206) germacrene D (181) p-mentha-24(8)-diene (98) α-pinene (94) β-elemene (91)

[27] Cameroon β-Caryophyllene (40) β-elemene (144) α-santalene(95) (Z)-hex-3-enol (52) δ-cardinene (48)

[26] Egypt Bicycloelemene (236) limonene (166) β-pinene(143) α-fenchene (66) α-pinene (54)

Fruit pulp

Present findings Ghana

Ccedil-Sitosterol (1982) 2-hydroxy-1-(hydroxymethyl)ethyl ester (1348) 2-hexenoic acid methyl ester(1027) 2-propenoic acid 3-phenyl- methyl ester

(867) Υ-sitosterol (496)

[36] MalaysiaMethyl (E)-2-butenoate (1970) Methyl (E)-2-hexenoate (1840) (Z)-3-hexenol (97) linalool

(930) methyl 2-hydroxyhexanoate (52)

[33] Cote drsquoIvoire

Methyl (E)-2-hexenoate (398) 3-pyridinocarbonylhydrazide (78) methyl hexanoate

(54) methyl (E)-2-butenoate (48) 23-dihydrobenzofuran (45)

[34] CubaMethyl 3-phenyl-2-propenoate (106) hexadecanoicacid (97) methyl (E)-2-hexenoate (88) methyl 2-

hydroxy-4-methylvalerate (72) linalool (29)

[30] Sri LankaMethyl hexanoate (3095) methyl (E)-hex-2-enoate(2670) trans-β-farnesene (645) dichloromethane

(572) methyl but-2-enoate (475)

[28] Cameroon2-Hexenoic acid methyl ester (239) β-caryophyllene(127) 18-cineole (99) 2-hexenoic acid ethyl ester

(86) linalool (78)

Biochemistry Research International 7

food processing and preservation as well as cosmetic andpharmaceutical industries

Data Availability

All data generated or analyzed during this study are includedin this published article

Conflicts of Interest

All authors declare no competing financial professional orpersonal interests that might have influenced the perfor-mance or presentation of this work

Authorsrsquo Contributions

LSB conceived the study LSB JNG and RO designed allexperiments LSB JNG and RO collected the samples JNGand RO carried out all the experiments LSB JNG and ROperformed the data analysis JNG drafted and LSB edited theinitial manuscript All authors read and approved the finalmanuscript JNG and RO contributed equally to this work

Acknowledgments

e authors are grateful to the Department of Chemistry andthe KNUST Central Laboratory for the use of their facilitiesfor this study e authors acknowledge Miss Judith Ananeof KNUST for technical support

References

[1] Y-Z Fang S Yang and G Wu ldquoFree radicals antioxidantsand nutritionrdquo Nutrition vol 18 no 10 pp 872ndash879 2002

[2] L Lyras N J Cairns A Jenner J Peter and B Halliwell ldquoAnassessment of oxidative damage to proteins lipids and DNAin brain from patients with Alzheimerrsquos diseaserdquo Journal ofNeurochemistry vol 68 no 5 pp 2061ndash2069 1997

[3] L J Machlin and A Bendich ldquoFree radical tissue damageprotective role of antioxidant nutrientsrdquo FASEB Journalvol 1 no 6 pp 441ndash445 1987

[4] B Halliwell ldquoLipid peroxidation antioxidants and cardio-vascular disease how should we move forwardrdquo Cardio-vascular Research vol 47 no 3 pp 410ndash418 2000

[5] P Poprac K Jomova M Simunkova V Kollar C J Rhodesand M Valko ldquoTargeting free radicals in oxidative stress-related human diseasesrdquo Trends in Pharmacological Sciencesvol 38 no 7 pp 592ndash607 2017

[6] K Yagi ldquoLipid peroxides and human diseasesrdquo Chemistry andPhysics of Lipids vol 45 no 2ndash4 pp 337ndash351 1987

[7] K H S Farvin and C Jacobsen ldquoPhenolic compounds andantioxidant activities of selected species of seaweeds fromDanish coastrdquo Food Chemistry vol 138 no 2-3 pp 1670ndash1681 2013

[8] E R Sherwin ldquoAntioxidantsrdquo Food Additives vol 139ndash1931990

[9] R S Lanigan and T A Yamarik ldquoFinal report on the safetyassessment of BHT (1)rdquo International Journal of Toxicologyvol 21 pp 19ndash94 2002

[10] R C Lindenschmidt A F Tryka M E Goad andH P Witschi ldquoe effects of dietary butylated hydrox-ytoluene on liver and colon tumor development in micerdquoToxicology vol 38 no 2 pp 151ndash160 1986

[11] Y He and F Shahidi ldquoAntioxidant activity of green tea and itscatechins in a fish meat model systemrdquo Journal of Agriculturaland Food Chemistry vol 45 no 11 pp 4262ndash4266 1997

[12] C Jacobsen M B Let N S Nielsen and A S MeyerldquoAntioxidant strategies for preventing oxidative flavour de-terioration of foods enriched with N-3 polyunsaturated lipidsa comparative evaluationrdquo Trends in Food Science amp Tech-nology vol 19 no 2 pp 76ndash93 2008

[13] A K Dhakad V V Pandey S Beg J M Rawat and A SinghldquoBiological medicinal and toxicological significance of Eu-calyptus leaf essential oil a reviewrdquo Journal of the Science ofFood and Agriculture vol 98 no 3 pp 833ndash848 2018

[14] M G Miguel ldquoAntioxidant and anti-inflammatory activitiesof essential oils a short reviewrdquo Molecules vol 15 no 12pp 9252ndash9287 2010

[15] P Rubiolo B Sgorbini E Liberto C Cordero and C BicchildquoEssential oils and volatiles sample preparation and analysisA reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 282ndash290 2010

[16] K Husnu Can Baser and G BuchbauerHandbook of EssentialOils Science Technology and Applications CRC Press BocaRaton FL USA 2015

[17] H S Elshafie and I Camele ldquoAn overview of the biologicaleffects of somemediterranean essential oils on human healthrdquoBioMed Research International vol 2017 Article ID 926846814 pages 2017

[18] R Amorati M C Foti and L Valgimigli ldquoAntioxidant ac-tivity of essential oilsrdquo Journal of Agricultural and FoodChemistry vol 61 no 46 pp 10835ndash10847 2013

[19] J R Calo P G Crandall C A OrsquoBryan and S C RickeldquoEssential oils as antimicrobials in food systems-a reviewrdquoFood Control vol 54 pp 111ndash119 2015

[20] M K Swamy M S Akhtar and U Rani Sinniah ldquoAntimi-crobial properties of plant essential oils against humanpathogens and their mode of action an updated reviewrdquoEvidence-Based Complementary and Alternative Medicinevol 2016 Article ID 3012462 21 pages 2016

[21] R Perez-Roses E Risco R Vila P Pentildealver andS Cantildeigueral ldquoBiological and nonbiological antioxidant ac-tivity of some essential oilsrdquo Journal of Agricultural and FoodChemistry vol 64 no 23 pp 4716ndash4724 2016

[22] A V Coria-Tellez E Montalvo-Gonzalez E M Yahia andE N Obledo-Vazquez ldquoAnnona muricata a comprehensivereview on its traditional medicinal uses phytochemicalspharmacological activities mechanisms of action and toxic-ityrdquo Arabian Journal of Chemistry vol 11 no 5 pp 662ndash6912018

[23] S Moghadamtousi M Fadaeinasab S Nikzad G MohanH Ali and H Kadir ldquoAnnona muricata (Annonaceae) areview of its traditional uses isolated acetogenins and bi-ological activitiesrdquo International Journal of Molecular Sci-ences vol 16 no 7 pp 15625ndash15658 2015

[24] P Champy A Melot V Guerineau Eng et al ldquoQuantificationof acetogenins in Annona muricata linked to atypical par-kinsonism in guadelouperdquo Movement Disorders vol 20no 12 pp 1629ndash1633 2005

[25] K W Cheong C P Tan H Mirhosseini N S A HamidA Osman and M Basri ldquoEquilibrium headspace analysis ofvolatile flavor compounds extracted from soursop (Annonamuricata) using solid-phase microextractionrdquo Food ResearchInternational vol 43 no 5 pp 1267ndash1276 2010

[26] S S Elhawary M E E Tantawy M A Rabeh and E F NohaldquoDNA fingerprinting chemical composition antitumor andantimicrobial activities of the essential oils and extractives of

8 Biochemistry Research International

four Annona species from Egyptrdquo Journal of Natural SciencesResearch vol 3 no 59ndash68 p 11 2013

[27] F Fekam Boyom P H Amvam Zollo C Menut G Lamatyand J M Bessiere ldquoAromatic plants of tropical central AfricaPart XXVII Comparative study of the volatile constituents offive annonaceae species growing in Cameroonrdquo Flavour andFragrance Journal vol 11 no 6 pp 333ndash338 1996

[28] L Jirovetz G Buchbauer and M B Ngassoum ldquoEssential oilcompounds of the Annona muricata fresh fruit pulp fromCameroonrdquo Journal of Agricultural and Food Chemistryvol 46 no 9 pp 3719-3720 1998

[29] C Kossouoh M Moudachirou V Adjakidje J-C Chalchatand G Figueredo ldquoEssential oil chemical composition ofAnnona muricata L Leaves from Beninrdquo Journal of EssentialOil Research vol 19 no 4 pp 307ndash309 2007

[30] A J MacLeod and N M Pieris ldquoVolatile flavor componentsof soursop (Annona muricata)rdquo Journal of Agricultural andFood Chemistry vol 29 no 3 pp 488ndash490 1981

[31] C Marquez J Carlos A M Jimenez C Osorio R Jose andV Cartagena ldquoVolatile compounds during the ripening ofColombian soursop (Annona muricata L Cv Elita)rdquo Vitaevol 18 no 3 pp 245ndash250 2011

[32] M S Owolabi A Lanre Ogundajo N S Dosoky andW N Setzer ldquoe cytotoxic activity of Annona muricata leafoil from badagary NigeriardquoAmerican Journal of Essential Oilsand Natural Products vol 1 pp 1ndash3 2013

[33] Y Pelissier C Marion D Kone G Lamaty C Menut andJ-M Bessiere ldquoVolatile components of Annona muricata LrdquoJournal of Essential Oil Research vol 6 no 4 pp 411ndash4141994

[34] J A Pino J Aguero and R Marbot ldquoVolatile components ofsoursop (Annona muricata L)rdquo Journal of Essential Oil Re-search vol 13 no 2 pp 140-141 2001

[35] T D ang D N Dai T M Hoi and I A OgunwandeldquoStudy on the volatile oil contents of Annona glabra LAnnona squamosa L Annona muricata L and Annonareticulata L from Vietnamrdquo Natural Product Researchvol 27 no 13 pp 1232ndash1236 2013

[36] K C Wong and K H Khoo ldquoVolatile components ofMalaysian annona fruitsrdquo Flavour and Fragrance Journalvol 8 no 1 pp 5ndash10 1993

[37] A Wele I Ndoye and M Badiane ldquoFatty acid and essentialoil compositions of the seed oil of five Annona speciesrdquoNigerian Journal of Natural Products and Medicine vol 8no 1 pp 62ndash65 2004

[38] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Vol 456 Allured Pub-lishing Corporation Carol Stream IL USA 2007

[39] J K Patra Se-W Lee Y-S Kwon J Gyu Park andK-H Baek ldquoChemical characterization and antioxidant po-tential of volatile oil from an edible seaweed porphyra tenera(Kjellman 1897)rdquo Chemistry Central Journal vol 11 no 1p 34 2017

[40] P Prieto M Pineda and M Aguilar ldquoSpectrophotometricquantitation of antioxidant capacity through the formation ofa phosphomolybdenum complex specific application to thedetermination of vitamin Erdquo Analytical Biochemistryvol 269 no 2 pp 337ndash341 1999

[41] D Mukhopadhyay P Dasgupta D S Roy et al ldquoA sensitivein vitro spectrophotometric hydrogen peroxide scavengingassay using 110-phenanthrolinerdquo Free Radicals amp Antioxi-dants vol 6 no 1 2016

[42] L S Borquaye G Darko E Ocansey and E AnkomahldquoAntimicrobial and antioxidant properties of the crude

peptide extracts of Galatea paradoxa and Patella rusticardquoSpringerPlus vol 4 no 1 p 500 2015

[43] L S Borquaye G Darko N Oklu C Anson-Yevu andA Ababio ldquoAntimicrobial and antioxidant activities of ethylacetate and methanol extracts of Littorina littorea andGalateaparadoxardquo Cogent Chemistry vol 2 no 1 article 11618652016

[44] L Peng Y Kawagoe P Hogan and D Delmer ldquoSitosterol-beta- glucoside as primer for cellulose synthesis in plantsrdquoScience vol 295 no 5552 pp 147ndash150 2002

[45] A I Hussain F Anwar S T Hussain Sherazi andR Przybylski ldquoChemical composition antioxidant and an-timicrobial activities of basil (Ocimum basilicum) essential oilsdepends on seasonal variationsrdquo Food Chemistry vol 108no 3 pp 986ndash995 2008

[46] P C Santos-Gomes and M Fernandes-Ferreira ldquoOrgan- andseason-dependent variation in the essential oil composition ofSalvia officinalis L Cultivated at two different sitesrdquo Journal ofAgricultural and Food Chemistry vol 49 no 6 pp 2908ndash2916 2001

[47] W Aidi Wannes B Mhamdi B Marzouk and B MarzoukldquoVariations in essential oil and fatty acid composition duringMyrtus communis var italica fruit maturationrdquo FoodChemistry vol 112 no 3 pp 621ndash626 2009

[48] M Hudaib E Speroni A M Di Pietra and V Cavrini ldquoGCMS evaluation of thyme (Dymus vulgaris L) oil compositionand variations during the vegetative cyclerdquo Journal ofPharmaceutical and Biomedical Analysis vol 29 no 4pp 691ndash700 2002

[49] A M Viljoen S Subramoney S F v Vuuren K H C Baserand B Demirci ldquoe composition geographical variation andantimicrobial activity of Lippia javanica (verbenaceae) leafessential oilsrdquo Journal of Ethnopharmacology vol 96 no 1-2pp 271ndash277 2005

[50] C Demirci and A Studer Encyclopedia of Radicals inChemistry Biology and Materials Vol 2 John Wiley amp SonsChichester UK 2012

[51] M C Foti ldquoAntioxidant properties of phenolsrdquo Journal ofPharmacy and Pharmacology vol 59 no 12 pp 1673ndash16852007

[52] G W Burton T Doba E Gabe et al ldquoAutoxidation of bi-ological molecules 4 Maximizing the antioxidant activity ofphenolsrdquo Journal of the American Chemical Society vol 107no 24 pp 7053ndash7065 1985

Biochemistry Research International 9

Hindawiwwwhindawicom

International Journal of

Volume 2018

Zoology

Hindawiwwwhindawicom Volume 2018

Anatomy Research International

PeptidesInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Journal of Parasitology Research

GenomicsInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawi Publishing Corporation httpwwwhindawicom Volume 2013Hindawiwwwhindawicom

The Scientific World Journal

Volume 2018

Hindawiwwwhindawicom Volume 2018

BioinformaticsAdvances in

Marine BiologyJournal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Neuroscience Journal

Hindawiwwwhindawicom Volume 2018

BioMed Research International

Cell BiologyInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Biochemistry Research International

ArchaeaHindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Genetics Research International

Hindawiwwwhindawicom Volume 2018

Advances in

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Hindawiwwwhindawicom Volume 2018

International Journal of

MicrobiologyHindawiwwwhindawicom

Nucleic AcidsJournal of

Volume 2018

Submit your manuscripts atwwwhindawicom

DPPH scavenging and hydrogen peroxide assays revealedpromising antioxidant properties (Tables 3 and 4) emechanism of antioxidant activity includes prevention of theformation of the initiator radical and termination of radicalsin the chain propagation stage or via indirect routes such asenhancement of the activities of enzymes that mop up

reactive species or induction in the expression of theseenzymes [18 50] Because essential oils consist of a numberof different compounds the antioxidant activity observed isusually the synergistic effect of the various constituents [18]

Table 2 Composition of fruit pulp essential oil of Annona muricata as determined by GC-MS with tentative identified compounds

No RT SI Compound composition1 651 80 Nonane 1742 696 98 Hexanoic acid methyl ester 1863 774 96 2-Hexenoic acid methyl ester 10274 811 94 Pentanoic acid 2-hydroxy-4-methyl- methyl ester 0035 818 98 Pentanoic acid 2-hydroxy-3-methyl- methyl ester 0426 935 94 268-Trimethylbicyclo[420]oct-2-ene-18-diol 0237 1002 99 16-Octadien-3-ol 37-dimethyl- 0138 1112 94 2-Octenoic acid methyl ester (E)- 0489 1158 92 Dodecane 05910 1200 94 Phenylacetaldehyde 17111 1305 91 Tridecane 04312 1431 97 2-Propenoic acid 3-phenyl- methyl ester 86713 1483 98 β-Caryophyllene 17714 1530 96 45-di-epi-Aristolochene 03515 1572 93 Falcarinol 01816 1605 99 β-Guaiene 01717 2054 94 Hexadecanoic acid methyl ester 03318 2226 94 Glyceryl 2-laurate 15219 2231 99 9-Octadecenoic acid methyl ester (E)- 21820 2507 97 8-Octadecanoic acid 22021 2508 99 2-Hydroxy-1-(hydroxymethyl) ethyl ester 134822 2558 96 Ccedil-Sitosterol 198223 2644 94 9-Octadecanoic acid 45924 2644 96 Pentadecanoic acid 13-methyl- methyl ester 04225 2693 80 23-Dihydroxypropyl elaidate 38126 2702 96 Squalene 17427 2728 97 α-Sitosterol 30428 2728 99 Oleic acid 20029 2763 87 Octadecane 20330 2981 91 Campesterol 21931 3062 96 Υ-Sitosterol 49632 3244 99 Oleyl oleate 25333 3265 86 Nonadecatriene-514-diol 412

Esters 4600Sterols 3001Terpenes 403Alcohols 466Alkanes 479Aldehyde 171

Carboxylic acid 879Total 9999

No compound number in order of elution SI Similarity Index (library search of purity value of a compound) RT retention time in minutes

Table 3 Total antioxidant capacity (TAC) and total phenoliccontent (TPC) of fruit pulp and leaf essential oils

Sample TAClowast gAAE100 g TPClowastlowast gGAE100 gPulp essential oil 4903plusmn 048a 398plusmn 060bLeaf essential oil 5088plusmn 050a 438plusmn 042b

Columns with different letters indicate significant difference (Plt 005Sidakrsquos multiple comparison test) lowastTAC expressed in gram ascorbic acidequivalent per 100 g of sample (gAAE100 g) lowastlowastTPC expressed in gramgallic acid equivalent per 100 g of sample (gGAE100 g)

Table 4 DPPH free radical and hydrogen peroxide scavengingactivities of essential oils and hydrosols from leaf and fruit pulp ofAnnona muricata

Sample IC50 (μgmL)lowast H2O2 scavengedlowastlowast

Pulp essential oil 5120plusmn 51 2438plusmn 021Leaf essential oil 2448plusmn 32 3180plusmn 051Ascorbic acid 213plusmn 32 NDGallic acid ND 9500plusmn 112lowastlowastlowastlowastIC50 concentration of extract required to scavenge 50 of DPPH radicalslowastlowast H2O2 scavenged was determined at 1mgmL for essential oils lowastlowastlowastForgallic acid H2O2 scavenged was determined at 50 μgmL

6 Biochemistry Research International

In the DPPH radical scavenging assay a dose-dependentinhibition of the DPPH radical was observed in essential oiland standard ascorbic acid treatments e IC50 valuesobtained for the leaf and fruit pulp essential oils indicate agood inhibition of the DPPH radical In the hydrogenperoxide scavenging assay the leaf essential oil showedsuperior activity to the pulp essential oil e activity of bothessential oils could however be described as average as thepercent inhibition of hydrogen peroxide was less than 50for both oils

Both essential oils however displayed very good totalantioxidant activity as seen in Table 3 Both oils had highlevels of phenolic content and this may have contributed tothe antioxidant activities observed It has been postulatedthat phenolic compounds possess high reactivity towardsperoxyl radicals via a formal hydrogen atom transfer andthis is the basis of their antioxidant activity [18 51] Phenoliccompounds are therefore categorized as chain breaking

antioxidants [52] Many reports on the antioxidant potentialof essential oils exist [13] and this report further confirmsthe importance of essential oils as antioxidative agents Sincereactive oxygen species cause serious damage to nucleicacids proteins and lipids the impressive antioxidant ac-tivity of the essential oils from Annona muricata suggestspossible use as natural antioxidant source in food additivesand animal feed formulation

5 Conclusion

Sesquiterpenes were the major constituents of the leaf es-sential oils of Annona muricata from Ghana whereas thefruit pulp essential oil consisted of aliphatic compounds andsterols e most abundant compound in leaf essential oilwas δ-cadinene In the fruit pulp essential oil Ccedil-sitosterolwas most abundant Both essential oils displayed promisingantioxidant activities and suggests potential application in

Table 5 Comparison of leaf and fruit pulp essential oil composition from different studies

Source Location Constituents ( composition)Leaves

Present findings Ghana

δ-Cadinene (2258) α-muurolene (1064)andrographolide (651) τ-cadinol (647) ledene

oxide (II) (629) α-cadinol (565) β-caryophyllene(557)

[33] Cote drsquoIvoireβ-Caryophyllene (314) δ-cadinene (67)

α-muurolene (55) (E)-2-hexenol (48) τ-cadinol(43)

[29] Beninβ-Caryophyllene (136) δ-cadinene (91) epi-

α-cadinol (84) α-cadinol (83) isocaryophyllene(75)

[32] Nigeria (E)-Caryophyllene (389) eugenol (302) δ-cadinene(60) caryophyllene oxide (50) α-humulene (43)

[35] Vietnam β-Pinene (206) germacrene D (181) p-mentha-24(8)-diene (98) α-pinene (94) β-elemene (91)

[27] Cameroon β-Caryophyllene (40) β-elemene (144) α-santalene(95) (Z)-hex-3-enol (52) δ-cardinene (48)

[26] Egypt Bicycloelemene (236) limonene (166) β-pinene(143) α-fenchene (66) α-pinene (54)

Fruit pulp

Present findings Ghana

Ccedil-Sitosterol (1982) 2-hydroxy-1-(hydroxymethyl)ethyl ester (1348) 2-hexenoic acid methyl ester(1027) 2-propenoic acid 3-phenyl- methyl ester

(867) Υ-sitosterol (496)

[36] MalaysiaMethyl (E)-2-butenoate (1970) Methyl (E)-2-hexenoate (1840) (Z)-3-hexenol (97) linalool

(930) methyl 2-hydroxyhexanoate (52)

[33] Cote drsquoIvoire

Methyl (E)-2-hexenoate (398) 3-pyridinocarbonylhydrazide (78) methyl hexanoate

(54) methyl (E)-2-butenoate (48) 23-dihydrobenzofuran (45)

[34] CubaMethyl 3-phenyl-2-propenoate (106) hexadecanoicacid (97) methyl (E)-2-hexenoate (88) methyl 2-

hydroxy-4-methylvalerate (72) linalool (29)

[30] Sri LankaMethyl hexanoate (3095) methyl (E)-hex-2-enoate(2670) trans-β-farnesene (645) dichloromethane

(572) methyl but-2-enoate (475)

[28] Cameroon2-Hexenoic acid methyl ester (239) β-caryophyllene(127) 18-cineole (99) 2-hexenoic acid ethyl ester

(86) linalool (78)

Biochemistry Research International 7

food processing and preservation as well as cosmetic andpharmaceutical industries

Data Availability

All data generated or analyzed during this study are includedin this published article

Conflicts of Interest

All authors declare no competing financial professional orpersonal interests that might have influenced the perfor-mance or presentation of this work

Authorsrsquo Contributions

LSB conceived the study LSB JNG and RO designed allexperiments LSB JNG and RO collected the samples JNGand RO carried out all the experiments LSB JNG and ROperformed the data analysis JNG drafted and LSB edited theinitial manuscript All authors read and approved the finalmanuscript JNG and RO contributed equally to this work

Acknowledgments

e authors are grateful to the Department of Chemistry andthe KNUST Central Laboratory for the use of their facilitiesfor this study e authors acknowledge Miss Judith Ananeof KNUST for technical support

References

[1] Y-Z Fang S Yang and G Wu ldquoFree radicals antioxidantsand nutritionrdquo Nutrition vol 18 no 10 pp 872ndash879 2002

[2] L Lyras N J Cairns A Jenner J Peter and B Halliwell ldquoAnassessment of oxidative damage to proteins lipids and DNAin brain from patients with Alzheimerrsquos diseaserdquo Journal ofNeurochemistry vol 68 no 5 pp 2061ndash2069 1997

[3] L J Machlin and A Bendich ldquoFree radical tissue damageprotective role of antioxidant nutrientsrdquo FASEB Journalvol 1 no 6 pp 441ndash445 1987

[4] B Halliwell ldquoLipid peroxidation antioxidants and cardio-vascular disease how should we move forwardrdquo Cardio-vascular Research vol 47 no 3 pp 410ndash418 2000

[5] P Poprac K Jomova M Simunkova V Kollar C J Rhodesand M Valko ldquoTargeting free radicals in oxidative stress-related human diseasesrdquo Trends in Pharmacological Sciencesvol 38 no 7 pp 592ndash607 2017

[6] K Yagi ldquoLipid peroxides and human diseasesrdquo Chemistry andPhysics of Lipids vol 45 no 2ndash4 pp 337ndash351 1987

[7] K H S Farvin and C Jacobsen ldquoPhenolic compounds andantioxidant activities of selected species of seaweeds fromDanish coastrdquo Food Chemistry vol 138 no 2-3 pp 1670ndash1681 2013

[8] E R Sherwin ldquoAntioxidantsrdquo Food Additives vol 139ndash1931990

[9] R S Lanigan and T A Yamarik ldquoFinal report on the safetyassessment of BHT (1)rdquo International Journal of Toxicologyvol 21 pp 19ndash94 2002

[10] R C Lindenschmidt A F Tryka M E Goad andH P Witschi ldquoe effects of dietary butylated hydrox-ytoluene on liver and colon tumor development in micerdquoToxicology vol 38 no 2 pp 151ndash160 1986

[11] Y He and F Shahidi ldquoAntioxidant activity of green tea and itscatechins in a fish meat model systemrdquo Journal of Agriculturaland Food Chemistry vol 45 no 11 pp 4262ndash4266 1997

[12] C Jacobsen M B Let N S Nielsen and A S MeyerldquoAntioxidant strategies for preventing oxidative flavour de-terioration of foods enriched with N-3 polyunsaturated lipidsa comparative evaluationrdquo Trends in Food Science amp Tech-nology vol 19 no 2 pp 76ndash93 2008

[13] A K Dhakad V V Pandey S Beg J M Rawat and A SinghldquoBiological medicinal and toxicological significance of Eu-calyptus leaf essential oil a reviewrdquo Journal of the Science ofFood and Agriculture vol 98 no 3 pp 833ndash848 2018

[14] M G Miguel ldquoAntioxidant and anti-inflammatory activitiesof essential oils a short reviewrdquo Molecules vol 15 no 12pp 9252ndash9287 2010

[15] P Rubiolo B Sgorbini E Liberto C Cordero and C BicchildquoEssential oils and volatiles sample preparation and analysisA reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 282ndash290 2010

[16] K Husnu Can Baser and G BuchbauerHandbook of EssentialOils Science Technology and Applications CRC Press BocaRaton FL USA 2015

[17] H S Elshafie and I Camele ldquoAn overview of the biologicaleffects of somemediterranean essential oils on human healthrdquoBioMed Research International vol 2017 Article ID 926846814 pages 2017

[18] R Amorati M C Foti and L Valgimigli ldquoAntioxidant ac-tivity of essential oilsrdquo Journal of Agricultural and FoodChemistry vol 61 no 46 pp 10835ndash10847 2013

[19] J R Calo P G Crandall C A OrsquoBryan and S C RickeldquoEssential oils as antimicrobials in food systems-a reviewrdquoFood Control vol 54 pp 111ndash119 2015

[20] M K Swamy M S Akhtar and U Rani Sinniah ldquoAntimi-crobial properties of plant essential oils against humanpathogens and their mode of action an updated reviewrdquoEvidence-Based Complementary and Alternative Medicinevol 2016 Article ID 3012462 21 pages 2016

[21] R Perez-Roses E Risco R Vila P Pentildealver andS Cantildeigueral ldquoBiological and nonbiological antioxidant ac-tivity of some essential oilsrdquo Journal of Agricultural and FoodChemistry vol 64 no 23 pp 4716ndash4724 2016

[22] A V Coria-Tellez E Montalvo-Gonzalez E M Yahia andE N Obledo-Vazquez ldquoAnnona muricata a comprehensivereview on its traditional medicinal uses phytochemicalspharmacological activities mechanisms of action and toxic-ityrdquo Arabian Journal of Chemistry vol 11 no 5 pp 662ndash6912018

[23] S Moghadamtousi M Fadaeinasab S Nikzad G MohanH Ali and H Kadir ldquoAnnona muricata (Annonaceae) areview of its traditional uses isolated acetogenins and bi-ological activitiesrdquo International Journal of Molecular Sci-ences vol 16 no 7 pp 15625ndash15658 2015

[24] P Champy A Melot V Guerineau Eng et al ldquoQuantificationof acetogenins in Annona muricata linked to atypical par-kinsonism in guadelouperdquo Movement Disorders vol 20no 12 pp 1629ndash1633 2005

[25] K W Cheong C P Tan H Mirhosseini N S A HamidA Osman and M Basri ldquoEquilibrium headspace analysis ofvolatile flavor compounds extracted from soursop (Annonamuricata) using solid-phase microextractionrdquo Food ResearchInternational vol 43 no 5 pp 1267ndash1276 2010

[26] S S Elhawary M E E Tantawy M A Rabeh and E F NohaldquoDNA fingerprinting chemical composition antitumor andantimicrobial activities of the essential oils and extractives of

8 Biochemistry Research International

four Annona species from Egyptrdquo Journal of Natural SciencesResearch vol 3 no 59ndash68 p 11 2013

[27] F Fekam Boyom P H Amvam Zollo C Menut G Lamatyand J M Bessiere ldquoAromatic plants of tropical central AfricaPart XXVII Comparative study of the volatile constituents offive annonaceae species growing in Cameroonrdquo Flavour andFragrance Journal vol 11 no 6 pp 333ndash338 1996

[28] L Jirovetz G Buchbauer and M B Ngassoum ldquoEssential oilcompounds of the Annona muricata fresh fruit pulp fromCameroonrdquo Journal of Agricultural and Food Chemistryvol 46 no 9 pp 3719-3720 1998

[29] C Kossouoh M Moudachirou V Adjakidje J-C Chalchatand G Figueredo ldquoEssential oil chemical composition ofAnnona muricata L Leaves from Beninrdquo Journal of EssentialOil Research vol 19 no 4 pp 307ndash309 2007

[30] A J MacLeod and N M Pieris ldquoVolatile flavor componentsof soursop (Annona muricata)rdquo Journal of Agricultural andFood Chemistry vol 29 no 3 pp 488ndash490 1981

[31] C Marquez J Carlos A M Jimenez C Osorio R Jose andV Cartagena ldquoVolatile compounds during the ripening ofColombian soursop (Annona muricata L Cv Elita)rdquo Vitaevol 18 no 3 pp 245ndash250 2011

[32] M S Owolabi A Lanre Ogundajo N S Dosoky andW N Setzer ldquoe cytotoxic activity of Annona muricata leafoil from badagary NigeriardquoAmerican Journal of Essential Oilsand Natural Products vol 1 pp 1ndash3 2013

[33] Y Pelissier C Marion D Kone G Lamaty C Menut andJ-M Bessiere ldquoVolatile components of Annona muricata LrdquoJournal of Essential Oil Research vol 6 no 4 pp 411ndash4141994

[34] J A Pino J Aguero and R Marbot ldquoVolatile components ofsoursop (Annona muricata L)rdquo Journal of Essential Oil Re-search vol 13 no 2 pp 140-141 2001

[35] T D ang D N Dai T M Hoi and I A OgunwandeldquoStudy on the volatile oil contents of Annona glabra LAnnona squamosa L Annona muricata L and Annonareticulata L from Vietnamrdquo Natural Product Researchvol 27 no 13 pp 1232ndash1236 2013

[36] K C Wong and K H Khoo ldquoVolatile components ofMalaysian annona fruitsrdquo Flavour and Fragrance Journalvol 8 no 1 pp 5ndash10 1993

[37] A Wele I Ndoye and M Badiane ldquoFatty acid and essentialoil compositions of the seed oil of five Annona speciesrdquoNigerian Journal of Natural Products and Medicine vol 8no 1 pp 62ndash65 2004

[38] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Vol 456 Allured Pub-lishing Corporation Carol Stream IL USA 2007

[39] J K Patra Se-W Lee Y-S Kwon J Gyu Park andK-H Baek ldquoChemical characterization and antioxidant po-tential of volatile oil from an edible seaweed porphyra tenera(Kjellman 1897)rdquo Chemistry Central Journal vol 11 no 1p 34 2017

[40] P Prieto M Pineda and M Aguilar ldquoSpectrophotometricquantitation of antioxidant capacity through the formation ofa phosphomolybdenum complex specific application to thedetermination of vitamin Erdquo Analytical Biochemistryvol 269 no 2 pp 337ndash341 1999

[41] D Mukhopadhyay P Dasgupta D S Roy et al ldquoA sensitivein vitro spectrophotometric hydrogen peroxide scavengingassay using 110-phenanthrolinerdquo Free Radicals amp Antioxi-dants vol 6 no 1 2016

[42] L S Borquaye G Darko E Ocansey and E AnkomahldquoAntimicrobial and antioxidant properties of the crude

peptide extracts of Galatea paradoxa and Patella rusticardquoSpringerPlus vol 4 no 1 p 500 2015

[43] L S Borquaye G Darko N Oklu C Anson-Yevu andA Ababio ldquoAntimicrobial and antioxidant activities of ethylacetate and methanol extracts of Littorina littorea andGalateaparadoxardquo Cogent Chemistry vol 2 no 1 article 11618652016

[44] L Peng Y Kawagoe P Hogan and D Delmer ldquoSitosterol-beta- glucoside as primer for cellulose synthesis in plantsrdquoScience vol 295 no 5552 pp 147ndash150 2002

[45] A I Hussain F Anwar S T Hussain Sherazi andR Przybylski ldquoChemical composition antioxidant and an-timicrobial activities of basil (Ocimum basilicum) essential oilsdepends on seasonal variationsrdquo Food Chemistry vol 108no 3 pp 986ndash995 2008

[46] P C Santos-Gomes and M Fernandes-Ferreira ldquoOrgan- andseason-dependent variation in the essential oil composition ofSalvia officinalis L Cultivated at two different sitesrdquo Journal ofAgricultural and Food Chemistry vol 49 no 6 pp 2908ndash2916 2001

[47] W Aidi Wannes B Mhamdi B Marzouk and B MarzoukldquoVariations in essential oil and fatty acid composition duringMyrtus communis var italica fruit maturationrdquo FoodChemistry vol 112 no 3 pp 621ndash626 2009

[48] M Hudaib E Speroni A M Di Pietra and V Cavrini ldquoGCMS evaluation of thyme (Dymus vulgaris L) oil compositionand variations during the vegetative cyclerdquo Journal ofPharmaceutical and Biomedical Analysis vol 29 no 4pp 691ndash700 2002

[49] A M Viljoen S Subramoney S F v Vuuren K H C Baserand B Demirci ldquoe composition geographical variation andantimicrobial activity of Lippia javanica (verbenaceae) leafessential oilsrdquo Journal of Ethnopharmacology vol 96 no 1-2pp 271ndash277 2005

[50] C Demirci and A Studer Encyclopedia of Radicals inChemistry Biology and Materials Vol 2 John Wiley amp SonsChichester UK 2012

[51] M C Foti ldquoAntioxidant properties of phenolsrdquo Journal ofPharmacy and Pharmacology vol 59 no 12 pp 1673ndash16852007

[52] G W Burton T Doba E Gabe et al ldquoAutoxidation of bi-ological molecules 4 Maximizing the antioxidant activity ofphenolsrdquo Journal of the American Chemical Society vol 107no 24 pp 7053ndash7065 1985

Biochemistry Research International 9

Hindawiwwwhindawicom

International Journal of

Volume 2018

Zoology

Hindawiwwwhindawicom Volume 2018

Anatomy Research International

PeptidesInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Journal of Parasitology Research

GenomicsInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawi Publishing Corporation httpwwwhindawicom Volume 2013Hindawiwwwhindawicom

The Scientific World Journal

Volume 2018

Hindawiwwwhindawicom Volume 2018

BioinformaticsAdvances in

Marine BiologyJournal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Neuroscience Journal

Hindawiwwwhindawicom Volume 2018

BioMed Research International

Cell BiologyInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Biochemistry Research International

ArchaeaHindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Genetics Research International

Hindawiwwwhindawicom Volume 2018

Advances in

Virolog y Stem Cells International

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Enzyme Research

Hindawiwwwhindawicom Volume 2018

International Journal of

MicrobiologyHindawiwwwhindawicom

Nucleic AcidsJournal of

Volume 2018

Submit your manuscripts atwwwhindawicom

In the DPPH radical scavenging assay a dose-dependentinhibition of the DPPH radical was observed in essential oiland standard ascorbic acid treatments e IC50 valuesobtained for the leaf and fruit pulp essential oils indicate agood inhibition of the DPPH radical In the hydrogenperoxide scavenging assay the leaf essential oil showedsuperior activity to the pulp essential oil e activity of bothessential oils could however be described as average as thepercent inhibition of hydrogen peroxide was less than 50for both oils

Both essential oils however displayed very good totalantioxidant activity as seen in Table 3 Both oils had highlevels of phenolic content and this may have contributed tothe antioxidant activities observed It has been postulatedthat phenolic compounds possess high reactivity towardsperoxyl radicals via a formal hydrogen atom transfer andthis is the basis of their antioxidant activity [18 51] Phenoliccompounds are therefore categorized as chain breaking

antioxidants [52] Many reports on the antioxidant potentialof essential oils exist [13] and this report further confirmsthe importance of essential oils as antioxidative agents Sincereactive oxygen species cause serious damage to nucleicacids proteins and lipids the impressive antioxidant ac-tivity of the essential oils from Annona muricata suggestspossible use as natural antioxidant source in food additivesand animal feed formulation

5 Conclusion

Sesquiterpenes were the major constituents of the leaf es-sential oils of Annona muricata from Ghana whereas thefruit pulp essential oil consisted of aliphatic compounds andsterols e most abundant compound in leaf essential oilwas δ-cadinene In the fruit pulp essential oil Ccedil-sitosterolwas most abundant Both essential oils displayed promisingantioxidant activities and suggests potential application in

Table 5 Comparison of leaf and fruit pulp essential oil composition from different studies

Source Location Constituents ( composition)Leaves

Present findings Ghana

δ-Cadinene (2258) α-muurolene (1064)andrographolide (651) τ-cadinol (647) ledene

oxide (II) (629) α-cadinol (565) β-caryophyllene(557)

[33] Cote drsquoIvoireβ-Caryophyllene (314) δ-cadinene (67)

α-muurolene (55) (E)-2-hexenol (48) τ-cadinol(43)

[29] Beninβ-Caryophyllene (136) δ-cadinene (91) epi-

α-cadinol (84) α-cadinol (83) isocaryophyllene(75)

[32] Nigeria (E)-Caryophyllene (389) eugenol (302) δ-cadinene(60) caryophyllene oxide (50) α-humulene (43)

[35] Vietnam β-Pinene (206) germacrene D (181) p-mentha-24(8)-diene (98) α-pinene (94) β-elemene (91)

[27] Cameroon β-Caryophyllene (40) β-elemene (144) α-santalene(95) (Z)-hex-3-enol (52) δ-cardinene (48)

[26] Egypt Bicycloelemene (236) limonene (166) β-pinene(143) α-fenchene (66) α-pinene (54)

Fruit pulp

Present findings Ghana

Ccedil-Sitosterol (1982) 2-hydroxy-1-(hydroxymethyl)ethyl ester (1348) 2-hexenoic acid methyl ester(1027) 2-propenoic acid 3-phenyl- methyl ester

(867) Υ-sitosterol (496)

[36] MalaysiaMethyl (E)-2-butenoate (1970) Methyl (E)-2-hexenoate (1840) (Z)-3-hexenol (97) linalool

(930) methyl 2-hydroxyhexanoate (52)

[33] Cote drsquoIvoire

Methyl (E)-2-hexenoate (398) 3-pyridinocarbonylhydrazide (78) methyl hexanoate

(54) methyl (E)-2-butenoate (48) 23-dihydrobenzofuran (45)

[34] CubaMethyl 3-phenyl-2-propenoate (106) hexadecanoicacid (97) methyl (E)-2-hexenoate (88) methyl 2-

hydroxy-4-methylvalerate (72) linalool (29)

[30] Sri LankaMethyl hexanoate (3095) methyl (E)-hex-2-enoate(2670) trans-β-farnesene (645) dichloromethane

(572) methyl but-2-enoate (475)

[28] Cameroon2-Hexenoic acid methyl ester (239) β-caryophyllene(127) 18-cineole (99) 2-hexenoic acid ethyl ester

(86) linalool (78)

Biochemistry Research International 7

food processing and preservation as well as cosmetic andpharmaceutical industries

Data Availability

All data generated or analyzed during this study are includedin this published article

Conflicts of Interest

All authors declare no competing financial professional orpersonal interests that might have influenced the perfor-mance or presentation of this work

Authorsrsquo Contributions

LSB conceived the study LSB JNG and RO designed allexperiments LSB JNG and RO collected the samples JNGand RO carried out all the experiments LSB JNG and ROperformed the data analysis JNG drafted and LSB edited theinitial manuscript All authors read and approved the finalmanuscript JNG and RO contributed equally to this work

Acknowledgments

e authors are grateful to the Department of Chemistry andthe KNUST Central Laboratory for the use of their facilitiesfor this study e authors acknowledge Miss Judith Ananeof KNUST for technical support

References

[1] Y-Z Fang S Yang and G Wu ldquoFree radicals antioxidantsand nutritionrdquo Nutrition vol 18 no 10 pp 872ndash879 2002

[2] L Lyras N J Cairns A Jenner J Peter and B Halliwell ldquoAnassessment of oxidative damage to proteins lipids and DNAin brain from patients with Alzheimerrsquos diseaserdquo Journal ofNeurochemistry vol 68 no 5 pp 2061ndash2069 1997

[3] L J Machlin and A Bendich ldquoFree radical tissue damageprotective role of antioxidant nutrientsrdquo FASEB Journalvol 1 no 6 pp 441ndash445 1987

[4] B Halliwell ldquoLipid peroxidation antioxidants and cardio-vascular disease how should we move forwardrdquo Cardio-vascular Research vol 47 no 3 pp 410ndash418 2000

[5] P Poprac K Jomova M Simunkova V Kollar C J Rhodesand M Valko ldquoTargeting free radicals in oxidative stress-related human diseasesrdquo Trends in Pharmacological Sciencesvol 38 no 7 pp 592ndash607 2017

[6] K Yagi ldquoLipid peroxides and human diseasesrdquo Chemistry andPhysics of Lipids vol 45 no 2ndash4 pp 337ndash351 1987

[7] K H S Farvin and C Jacobsen ldquoPhenolic compounds andantioxidant activities of selected species of seaweeds fromDanish coastrdquo Food Chemistry vol 138 no 2-3 pp 1670ndash1681 2013

[8] E R Sherwin ldquoAntioxidantsrdquo Food Additives vol 139ndash1931990

[9] R S Lanigan and T A Yamarik ldquoFinal report on the safetyassessment of BHT (1)rdquo International Journal of Toxicologyvol 21 pp 19ndash94 2002

[10] R C Lindenschmidt A F Tryka M E Goad andH P Witschi ldquoe effects of dietary butylated hydrox-ytoluene on liver and colon tumor development in micerdquoToxicology vol 38 no 2 pp 151ndash160 1986

[11] Y He and F Shahidi ldquoAntioxidant activity of green tea and itscatechins in a fish meat model systemrdquo Journal of Agriculturaland Food Chemistry vol 45 no 11 pp 4262ndash4266 1997

[12] C Jacobsen M B Let N S Nielsen and A S MeyerldquoAntioxidant strategies for preventing oxidative flavour de-terioration of foods enriched with N-3 polyunsaturated lipidsa comparative evaluationrdquo Trends in Food Science amp Tech-nology vol 19 no 2 pp 76ndash93 2008

[13] A K Dhakad V V Pandey S Beg J M Rawat and A SinghldquoBiological medicinal and toxicological significance of Eu-calyptus leaf essential oil a reviewrdquo Journal of the Science ofFood and Agriculture vol 98 no 3 pp 833ndash848 2018

[14] M G Miguel ldquoAntioxidant and anti-inflammatory activitiesof essential oils a short reviewrdquo Molecules vol 15 no 12pp 9252ndash9287 2010

[15] P Rubiolo B Sgorbini E Liberto C Cordero and C BicchildquoEssential oils and volatiles sample preparation and analysisA reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 282ndash290 2010

[16] K Husnu Can Baser and G BuchbauerHandbook of EssentialOils Science Technology and Applications CRC Press BocaRaton FL USA 2015

[17] H S Elshafie and I Camele ldquoAn overview of the biologicaleffects of somemediterranean essential oils on human healthrdquoBioMed Research International vol 2017 Article ID 926846814 pages 2017

[18] R Amorati M C Foti and L Valgimigli ldquoAntioxidant ac-tivity of essential oilsrdquo Journal of Agricultural and FoodChemistry vol 61 no 46 pp 10835ndash10847 2013

[19] J R Calo P G Crandall C A OrsquoBryan and S C RickeldquoEssential oils as antimicrobials in food systems-a reviewrdquoFood Control vol 54 pp 111ndash119 2015

[20] M K Swamy M S Akhtar and U Rani Sinniah ldquoAntimi-crobial properties of plant essential oils against humanpathogens and their mode of action an updated reviewrdquoEvidence-Based Complementary and Alternative Medicinevol 2016 Article ID 3012462 21 pages 2016

[21] R Perez-Roses E Risco R Vila P Pentildealver andS Cantildeigueral ldquoBiological and nonbiological antioxidant ac-tivity of some essential oilsrdquo Journal of Agricultural and FoodChemistry vol 64 no 23 pp 4716ndash4724 2016

[22] A V Coria-Tellez E Montalvo-Gonzalez E M Yahia andE N Obledo-Vazquez ldquoAnnona muricata a comprehensivereview on its traditional medicinal uses phytochemicalspharmacological activities mechanisms of action and toxic-ityrdquo Arabian Journal of Chemistry vol 11 no 5 pp 662ndash6912018

[23] S Moghadamtousi M Fadaeinasab S Nikzad G MohanH Ali and H Kadir ldquoAnnona muricata (Annonaceae) areview of its traditional uses isolated acetogenins and bi-ological activitiesrdquo International Journal of Molecular Sci-ences vol 16 no 7 pp 15625ndash15658 2015

[24] P Champy A Melot V Guerineau Eng et al ldquoQuantificationof acetogenins in Annona muricata linked to atypical par-kinsonism in guadelouperdquo Movement Disorders vol 20no 12 pp 1629ndash1633 2005

[25] K W Cheong C P Tan H Mirhosseini N S A HamidA Osman and M Basri ldquoEquilibrium headspace analysis ofvolatile flavor compounds extracted from soursop (Annonamuricata) using solid-phase microextractionrdquo Food ResearchInternational vol 43 no 5 pp 1267ndash1276 2010

[26] S S Elhawary M E E Tantawy M A Rabeh and E F NohaldquoDNA fingerprinting chemical composition antitumor andantimicrobial activities of the essential oils and extractives of

8 Biochemistry Research International

four Annona species from Egyptrdquo Journal of Natural SciencesResearch vol 3 no 59ndash68 p 11 2013

[27] F Fekam Boyom P H Amvam Zollo C Menut G Lamatyand J M Bessiere ldquoAromatic plants of tropical central AfricaPart XXVII Comparative study of the volatile constituents offive annonaceae species growing in Cameroonrdquo Flavour andFragrance Journal vol 11 no 6 pp 333ndash338 1996

[28] L Jirovetz G Buchbauer and M B Ngassoum ldquoEssential oilcompounds of the Annona muricata fresh fruit pulp fromCameroonrdquo Journal of Agricultural and Food Chemistryvol 46 no 9 pp 3719-3720 1998

[29] C Kossouoh M Moudachirou V Adjakidje J-C Chalchatand G Figueredo ldquoEssential oil chemical composition ofAnnona muricata L Leaves from Beninrdquo Journal of EssentialOil Research vol 19 no 4 pp 307ndash309 2007

[30] A J MacLeod and N M Pieris ldquoVolatile flavor componentsof soursop (Annona muricata)rdquo Journal of Agricultural andFood Chemistry vol 29 no 3 pp 488ndash490 1981

[31] C Marquez J Carlos A M Jimenez C Osorio R Jose andV Cartagena ldquoVolatile compounds during the ripening ofColombian soursop (Annona muricata L Cv Elita)rdquo Vitaevol 18 no 3 pp 245ndash250 2011

[32] M S Owolabi A Lanre Ogundajo N S Dosoky andW N Setzer ldquoe cytotoxic activity of Annona muricata leafoil from badagary NigeriardquoAmerican Journal of Essential Oilsand Natural Products vol 1 pp 1ndash3 2013

[33] Y Pelissier C Marion D Kone G Lamaty C Menut andJ-M Bessiere ldquoVolatile components of Annona muricata LrdquoJournal of Essential Oil Research vol 6 no 4 pp 411ndash4141994

[34] J A Pino J Aguero and R Marbot ldquoVolatile components ofsoursop (Annona muricata L)rdquo Journal of Essential Oil Re-search vol 13 no 2 pp 140-141 2001

[35] T D ang D N Dai T M Hoi and I A OgunwandeldquoStudy on the volatile oil contents of Annona glabra LAnnona squamosa L Annona muricata L and Annonareticulata L from Vietnamrdquo Natural Product Researchvol 27 no 13 pp 1232ndash1236 2013

[36] K C Wong and K H Khoo ldquoVolatile components ofMalaysian annona fruitsrdquo Flavour and Fragrance Journalvol 8 no 1 pp 5ndash10 1993

[37] A Wele I Ndoye and M Badiane ldquoFatty acid and essentialoil compositions of the seed oil of five Annona speciesrdquoNigerian Journal of Natural Products and Medicine vol 8no 1 pp 62ndash65 2004

[38] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Vol 456 Allured Pub-lishing Corporation Carol Stream IL USA 2007

[39] J K Patra Se-W Lee Y-S Kwon J Gyu Park andK-H Baek ldquoChemical characterization and antioxidant po-tential of volatile oil from an edible seaweed porphyra tenera(Kjellman 1897)rdquo Chemistry Central Journal vol 11 no 1p 34 2017

[40] P Prieto M Pineda and M Aguilar ldquoSpectrophotometricquantitation of antioxidant capacity through the formation ofa phosphomolybdenum complex specific application to thedetermination of vitamin Erdquo Analytical Biochemistryvol 269 no 2 pp 337ndash341 1999

[41] D Mukhopadhyay P Dasgupta D S Roy et al ldquoA sensitivein vitro spectrophotometric hydrogen peroxide scavengingassay using 110-phenanthrolinerdquo Free Radicals amp Antioxi-dants vol 6 no 1 2016

[42] L S Borquaye G Darko E Ocansey and E AnkomahldquoAntimicrobial and antioxidant properties of the crude

peptide extracts of Galatea paradoxa and Patella rusticardquoSpringerPlus vol 4 no 1 p 500 2015

[43] L S Borquaye G Darko N Oklu C Anson-Yevu andA Ababio ldquoAntimicrobial and antioxidant activities of ethylacetate and methanol extracts of Littorina littorea andGalateaparadoxardquo Cogent Chemistry vol 2 no 1 article 11618652016

[44] L Peng Y Kawagoe P Hogan and D Delmer ldquoSitosterol-beta- glucoside as primer for cellulose synthesis in plantsrdquoScience vol 295 no 5552 pp 147ndash150 2002

[45] A I Hussain F Anwar S T Hussain Sherazi andR Przybylski ldquoChemical composition antioxidant and an-timicrobial activities of basil (Ocimum basilicum) essential oilsdepends on seasonal variationsrdquo Food Chemistry vol 108no 3 pp 986ndash995 2008

[46] P C Santos-Gomes and M Fernandes-Ferreira ldquoOrgan- andseason-dependent variation in the essential oil composition ofSalvia officinalis L Cultivated at two different sitesrdquo Journal ofAgricultural and Food Chemistry vol 49 no 6 pp 2908ndash2916 2001

[47] W Aidi Wannes B Mhamdi B Marzouk and B MarzoukldquoVariations in essential oil and fatty acid composition duringMyrtus communis var italica fruit maturationrdquo FoodChemistry vol 112 no 3 pp 621ndash626 2009

[48] M Hudaib E Speroni A M Di Pietra and V Cavrini ldquoGCMS evaluation of thyme (Dymus vulgaris L) oil compositionand variations during the vegetative cyclerdquo Journal ofPharmaceutical and Biomedical Analysis vol 29 no 4pp 691ndash700 2002

[49] A M Viljoen S Subramoney S F v Vuuren K H C Baserand B Demirci ldquoe composition geographical variation andantimicrobial activity of Lippia javanica (verbenaceae) leafessential oilsrdquo Journal of Ethnopharmacology vol 96 no 1-2pp 271ndash277 2005

[50] C Demirci and A Studer Encyclopedia of Radicals inChemistry Biology and Materials Vol 2 John Wiley amp SonsChichester UK 2012

[51] M C Foti ldquoAntioxidant properties of phenolsrdquo Journal ofPharmacy and Pharmacology vol 59 no 12 pp 1673ndash16852007

[52] G W Burton T Doba E Gabe et al ldquoAutoxidation of bi-ological molecules 4 Maximizing the antioxidant activity ofphenolsrdquo Journal of the American Chemical Society vol 107no 24 pp 7053ndash7065 1985

Biochemistry Research International 9

Hindawiwwwhindawicom

International Journal of

Volume 2018

Zoology

Hindawiwwwhindawicom Volume 2018

Anatomy Research International

PeptidesInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Journal of Parasitology Research

GenomicsInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawi Publishing Corporation httpwwwhindawicom Volume 2013Hindawiwwwhindawicom

The Scientific World Journal

Volume 2018

Hindawiwwwhindawicom Volume 2018

BioinformaticsAdvances in

Marine BiologyJournal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Neuroscience Journal

Hindawiwwwhindawicom Volume 2018

BioMed Research International

Cell BiologyInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Biochemistry Research International

ArchaeaHindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Genetics Research International

Hindawiwwwhindawicom Volume 2018

Advances in

Virolog y Stem Cells International

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Enzyme Research

Hindawiwwwhindawicom Volume 2018

International Journal of

MicrobiologyHindawiwwwhindawicom

Nucleic AcidsJournal of

Volume 2018

Submit your manuscripts atwwwhindawicom

food processing and preservation as well as cosmetic andpharmaceutical industries

Data Availability

All data generated or analyzed during this study are includedin this published article

Conflicts of Interest

All authors declare no competing financial professional orpersonal interests that might have influenced the perfor-mance or presentation of this work

Authorsrsquo Contributions

LSB conceived the study LSB JNG and RO designed allexperiments LSB JNG and RO collected the samples JNGand RO carried out all the experiments LSB JNG and ROperformed the data analysis JNG drafted and LSB edited theinitial manuscript All authors read and approved the finalmanuscript JNG and RO contributed equally to this work

Acknowledgments

e authors are grateful to the Department of Chemistry andthe KNUST Central Laboratory for the use of their facilitiesfor this study e authors acknowledge Miss Judith Ananeof KNUST for technical support

References

[1] Y-Z Fang S Yang and G Wu ldquoFree radicals antioxidantsand nutritionrdquo Nutrition vol 18 no 10 pp 872ndash879 2002

[2] L Lyras N J Cairns A Jenner J Peter and B Halliwell ldquoAnassessment of oxidative damage to proteins lipids and DNAin brain from patients with Alzheimerrsquos diseaserdquo Journal ofNeurochemistry vol 68 no 5 pp 2061ndash2069 1997

[3] L J Machlin and A Bendich ldquoFree radical tissue damageprotective role of antioxidant nutrientsrdquo FASEB Journalvol 1 no 6 pp 441ndash445 1987

[4] B Halliwell ldquoLipid peroxidation antioxidants and cardio-vascular disease how should we move forwardrdquo Cardio-vascular Research vol 47 no 3 pp 410ndash418 2000

[5] P Poprac K Jomova M Simunkova V Kollar C J Rhodesand M Valko ldquoTargeting free radicals in oxidative stress-related human diseasesrdquo Trends in Pharmacological Sciencesvol 38 no 7 pp 592ndash607 2017

[6] K Yagi ldquoLipid peroxides and human diseasesrdquo Chemistry andPhysics of Lipids vol 45 no 2ndash4 pp 337ndash351 1987

[7] K H S Farvin and C Jacobsen ldquoPhenolic compounds andantioxidant activities of selected species of seaweeds fromDanish coastrdquo Food Chemistry vol 138 no 2-3 pp 1670ndash1681 2013

[8] E R Sherwin ldquoAntioxidantsrdquo Food Additives vol 139ndash1931990

[9] R S Lanigan and T A Yamarik ldquoFinal report on the safetyassessment of BHT (1)rdquo International Journal of Toxicologyvol 21 pp 19ndash94 2002

[10] R C Lindenschmidt A F Tryka M E Goad andH P Witschi ldquoe effects of dietary butylated hydrox-ytoluene on liver and colon tumor development in micerdquoToxicology vol 38 no 2 pp 151ndash160 1986

[11] Y He and F Shahidi ldquoAntioxidant activity of green tea and itscatechins in a fish meat model systemrdquo Journal of Agriculturaland Food Chemistry vol 45 no 11 pp 4262ndash4266 1997

[12] C Jacobsen M B Let N S Nielsen and A S MeyerldquoAntioxidant strategies for preventing oxidative flavour de-terioration of foods enriched with N-3 polyunsaturated lipidsa comparative evaluationrdquo Trends in Food Science amp Tech-nology vol 19 no 2 pp 76ndash93 2008

[13] A K Dhakad V V Pandey S Beg J M Rawat and A SinghldquoBiological medicinal and toxicological significance of Eu-calyptus leaf essential oil a reviewrdquo Journal of the Science ofFood and Agriculture vol 98 no 3 pp 833ndash848 2018

[14] M G Miguel ldquoAntioxidant and anti-inflammatory activitiesof essential oils a short reviewrdquo Molecules vol 15 no 12pp 9252ndash9287 2010

[15] P Rubiolo B Sgorbini E Liberto C Cordero and C BicchildquoEssential oils and volatiles sample preparation and analysisA reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 282ndash290 2010

[16] K Husnu Can Baser and G BuchbauerHandbook of EssentialOils Science Technology and Applications CRC Press BocaRaton FL USA 2015

[17] H S Elshafie and I Camele ldquoAn overview of the biologicaleffects of somemediterranean essential oils on human healthrdquoBioMed Research International vol 2017 Article ID 926846814 pages 2017

[18] R Amorati M C Foti and L Valgimigli ldquoAntioxidant ac-tivity of essential oilsrdquo Journal of Agricultural and FoodChemistry vol 61 no 46 pp 10835ndash10847 2013

[19] J R Calo P G Crandall C A OrsquoBryan and S C RickeldquoEssential oils as antimicrobials in food systems-a reviewrdquoFood Control vol 54 pp 111ndash119 2015

[20] M K Swamy M S Akhtar and U Rani Sinniah ldquoAntimi-crobial properties of plant essential oils against humanpathogens and their mode of action an updated reviewrdquoEvidence-Based Complementary and Alternative Medicinevol 2016 Article ID 3012462 21 pages 2016

[21] R Perez-Roses E Risco R Vila P Pentildealver andS Cantildeigueral ldquoBiological and nonbiological antioxidant ac-tivity of some essential oilsrdquo Journal of Agricultural and FoodChemistry vol 64 no 23 pp 4716ndash4724 2016

[22] A V Coria-Tellez E Montalvo-Gonzalez E M Yahia andE N Obledo-Vazquez ldquoAnnona muricata a comprehensivereview on its traditional medicinal uses phytochemicalspharmacological activities mechanisms of action and toxic-ityrdquo Arabian Journal of Chemistry vol 11 no 5 pp 662ndash6912018

[23] S Moghadamtousi M Fadaeinasab S Nikzad G MohanH Ali and H Kadir ldquoAnnona muricata (Annonaceae) areview of its traditional uses isolated acetogenins and bi-ological activitiesrdquo International Journal of Molecular Sci-ences vol 16 no 7 pp 15625ndash15658 2015

[24] P Champy A Melot V Guerineau Eng et al ldquoQuantificationof acetogenins in Annona muricata linked to atypical par-kinsonism in guadelouperdquo Movement Disorders vol 20no 12 pp 1629ndash1633 2005

[25] K W Cheong C P Tan H Mirhosseini N S A HamidA Osman and M Basri ldquoEquilibrium headspace analysis ofvolatile flavor compounds extracted from soursop (Annonamuricata) using solid-phase microextractionrdquo Food ResearchInternational vol 43 no 5 pp 1267ndash1276 2010

[26] S S Elhawary M E E Tantawy M A Rabeh and E F NohaldquoDNA fingerprinting chemical composition antitumor andantimicrobial activities of the essential oils and extractives of

8 Biochemistry Research International

four Annona species from Egyptrdquo Journal of Natural SciencesResearch vol 3 no 59ndash68 p 11 2013

[27] F Fekam Boyom P H Amvam Zollo C Menut G Lamatyand J M Bessiere ldquoAromatic plants of tropical central AfricaPart XXVII Comparative study of the volatile constituents offive annonaceae species growing in Cameroonrdquo Flavour andFragrance Journal vol 11 no 6 pp 333ndash338 1996

[28] L Jirovetz G Buchbauer and M B Ngassoum ldquoEssential oilcompounds of the Annona muricata fresh fruit pulp fromCameroonrdquo Journal of Agricultural and Food Chemistryvol 46 no 9 pp 3719-3720 1998

[29] C Kossouoh M Moudachirou V Adjakidje J-C Chalchatand G Figueredo ldquoEssential oil chemical composition ofAnnona muricata L Leaves from Beninrdquo Journal of EssentialOil Research vol 19 no 4 pp 307ndash309 2007

[30] A J MacLeod and N M Pieris ldquoVolatile flavor componentsof soursop (Annona muricata)rdquo Journal of Agricultural andFood Chemistry vol 29 no 3 pp 488ndash490 1981

[31] C Marquez J Carlos A M Jimenez C Osorio R Jose andV Cartagena ldquoVolatile compounds during the ripening ofColombian soursop (Annona muricata L Cv Elita)rdquo Vitaevol 18 no 3 pp 245ndash250 2011

[32] M S Owolabi A Lanre Ogundajo N S Dosoky andW N Setzer ldquoe cytotoxic activity of Annona muricata leafoil from badagary NigeriardquoAmerican Journal of Essential Oilsand Natural Products vol 1 pp 1ndash3 2013

[33] Y Pelissier C Marion D Kone G Lamaty C Menut andJ-M Bessiere ldquoVolatile components of Annona muricata LrdquoJournal of Essential Oil Research vol 6 no 4 pp 411ndash4141994

[34] J A Pino J Aguero and R Marbot ldquoVolatile components ofsoursop (Annona muricata L)rdquo Journal of Essential Oil Re-search vol 13 no 2 pp 140-141 2001

[35] T D ang D N Dai T M Hoi and I A OgunwandeldquoStudy on the volatile oil contents of Annona glabra LAnnona squamosa L Annona muricata L and Annonareticulata L from Vietnamrdquo Natural Product Researchvol 27 no 13 pp 1232ndash1236 2013

[36] K C Wong and K H Khoo ldquoVolatile components ofMalaysian annona fruitsrdquo Flavour and Fragrance Journalvol 8 no 1 pp 5ndash10 1993

[37] A Wele I Ndoye and M Badiane ldquoFatty acid and essentialoil compositions of the seed oil of five Annona speciesrdquoNigerian Journal of Natural Products and Medicine vol 8no 1 pp 62ndash65 2004

[38] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Vol 456 Allured Pub-lishing Corporation Carol Stream IL USA 2007

[39] J K Patra Se-W Lee Y-S Kwon J Gyu Park andK-H Baek ldquoChemical characterization and antioxidant po-tential of volatile oil from an edible seaweed porphyra tenera(Kjellman 1897)rdquo Chemistry Central Journal vol 11 no 1p 34 2017

[40] P Prieto M Pineda and M Aguilar ldquoSpectrophotometricquantitation of antioxidant capacity through the formation ofa phosphomolybdenum complex specific application to thedetermination of vitamin Erdquo Analytical Biochemistryvol 269 no 2 pp 337ndash341 1999

[41] D Mukhopadhyay P Dasgupta D S Roy et al ldquoA sensitivein vitro spectrophotometric hydrogen peroxide scavengingassay using 110-phenanthrolinerdquo Free Radicals amp Antioxi-dants vol 6 no 1 2016

[42] L S Borquaye G Darko E Ocansey and E AnkomahldquoAntimicrobial and antioxidant properties of the crude

peptide extracts of Galatea paradoxa and Patella rusticardquoSpringerPlus vol 4 no 1 p 500 2015

[43] L S Borquaye G Darko N Oklu C Anson-Yevu andA Ababio ldquoAntimicrobial and antioxidant activities of ethylacetate and methanol extracts of Littorina littorea andGalateaparadoxardquo Cogent Chemistry vol 2 no 1 article 11618652016

[44] L Peng Y Kawagoe P Hogan and D Delmer ldquoSitosterol-beta- glucoside as primer for cellulose synthesis in plantsrdquoScience vol 295 no 5552 pp 147ndash150 2002

[45] A I Hussain F Anwar S T Hussain Sherazi andR Przybylski ldquoChemical composition antioxidant and an-timicrobial activities of basil (Ocimum basilicum) essential oilsdepends on seasonal variationsrdquo Food Chemistry vol 108no 3 pp 986ndash995 2008

[46] P C Santos-Gomes and M Fernandes-Ferreira ldquoOrgan- andseason-dependent variation in the essential oil composition ofSalvia officinalis L Cultivated at two different sitesrdquo Journal ofAgricultural and Food Chemistry vol 49 no 6 pp 2908ndash2916 2001

[47] W Aidi Wannes B Mhamdi B Marzouk and B MarzoukldquoVariations in essential oil and fatty acid composition duringMyrtus communis var italica fruit maturationrdquo FoodChemistry vol 112 no 3 pp 621ndash626 2009

[48] M Hudaib E Speroni A M Di Pietra and V Cavrini ldquoGCMS evaluation of thyme (Dymus vulgaris L) oil compositionand variations during the vegetative cyclerdquo Journal ofPharmaceutical and Biomedical Analysis vol 29 no 4pp 691ndash700 2002

[49] A M Viljoen S Subramoney S F v Vuuren K H C Baserand B Demirci ldquoe composition geographical variation andantimicrobial activity of Lippia javanica (verbenaceae) leafessential oilsrdquo Journal of Ethnopharmacology vol 96 no 1-2pp 271ndash277 2005

[50] C Demirci and A Studer Encyclopedia of Radicals inChemistry Biology and Materials Vol 2 John Wiley amp SonsChichester UK 2012

[51] M C Foti ldquoAntioxidant properties of phenolsrdquo Journal ofPharmacy and Pharmacology vol 59 no 12 pp 1673ndash16852007

[52] G W Burton T Doba E Gabe et al ldquoAutoxidation of bi-ological molecules 4 Maximizing the antioxidant activity ofphenolsrdquo Journal of the American Chemical Society vol 107no 24 pp 7053ndash7065 1985

Biochemistry Research International 9

Hindawiwwwhindawicom

International Journal of

Volume 2018

Zoology

Hindawiwwwhindawicom Volume 2018

Anatomy Research International

PeptidesInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Journal of Parasitology Research

GenomicsInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawi Publishing Corporation httpwwwhindawicom Volume 2013Hindawiwwwhindawicom

The Scientific World Journal

Volume 2018

Hindawiwwwhindawicom Volume 2018

BioinformaticsAdvances in

Marine BiologyJournal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Neuroscience Journal

Hindawiwwwhindawicom Volume 2018

BioMed Research International

Cell BiologyInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Biochemistry Research International

ArchaeaHindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Genetics Research International

Hindawiwwwhindawicom Volume 2018

Advances in

Virolog y Stem Cells International

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Enzyme Research

Hindawiwwwhindawicom Volume 2018

International Journal of

MicrobiologyHindawiwwwhindawicom

Nucleic AcidsJournal of

Volume 2018

Submit your manuscripts atwwwhindawicom

four Annona species from Egyptrdquo Journal of Natural SciencesResearch vol 3 no 59ndash68 p 11 2013

[27] F Fekam Boyom P H Amvam Zollo C Menut G Lamatyand J M Bessiere ldquoAromatic plants of tropical central AfricaPart XXVII Comparative study of the volatile constituents offive annonaceae species growing in Cameroonrdquo Flavour andFragrance Journal vol 11 no 6 pp 333ndash338 1996

[28] L Jirovetz G Buchbauer and M B Ngassoum ldquoEssential oilcompounds of the Annona muricata fresh fruit pulp fromCameroonrdquo Journal of Agricultural and Food Chemistryvol 46 no 9 pp 3719-3720 1998

[29] C Kossouoh M Moudachirou V Adjakidje J-C Chalchatand G Figueredo ldquoEssential oil chemical composition ofAnnona muricata L Leaves from Beninrdquo Journal of EssentialOil Research vol 19 no 4 pp 307ndash309 2007

[30] A J MacLeod and N M Pieris ldquoVolatile flavor componentsof soursop (Annona muricata)rdquo Journal of Agricultural andFood Chemistry vol 29 no 3 pp 488ndash490 1981

[31] C Marquez J Carlos A M Jimenez C Osorio R Jose andV Cartagena ldquoVolatile compounds during the ripening ofColombian soursop (Annona muricata L Cv Elita)rdquo Vitaevol 18 no 3 pp 245ndash250 2011

[32] M S Owolabi A Lanre Ogundajo N S Dosoky andW N Setzer ldquoe cytotoxic activity of Annona muricata leafoil from badagary NigeriardquoAmerican Journal of Essential Oilsand Natural Products vol 1 pp 1ndash3 2013

[33] Y Pelissier C Marion D Kone G Lamaty C Menut andJ-M Bessiere ldquoVolatile components of Annona muricata LrdquoJournal of Essential Oil Research vol 6 no 4 pp 411ndash4141994

[34] J A Pino J Aguero and R Marbot ldquoVolatile components ofsoursop (Annona muricata L)rdquo Journal of Essential Oil Re-search vol 13 no 2 pp 140-141 2001

[35] T D ang D N Dai T M Hoi and I A OgunwandeldquoStudy on the volatile oil contents of Annona glabra LAnnona squamosa L Annona muricata L and Annonareticulata L from Vietnamrdquo Natural Product Researchvol 27 no 13 pp 1232ndash1236 2013

[36] K C Wong and K H Khoo ldquoVolatile components ofMalaysian annona fruitsrdquo Flavour and Fragrance Journalvol 8 no 1 pp 5ndash10 1993

[37] A Wele I Ndoye and M Badiane ldquoFatty acid and essentialoil compositions of the seed oil of five Annona speciesrdquoNigerian Journal of Natural Products and Medicine vol 8no 1 pp 62ndash65 2004

[38] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Vol 456 Allured Pub-lishing Corporation Carol Stream IL USA 2007

[39] J K Patra Se-W Lee Y-S Kwon J Gyu Park andK-H Baek ldquoChemical characterization and antioxidant po-tential of volatile oil from an edible seaweed porphyra tenera(Kjellman 1897)rdquo Chemistry Central Journal vol 11 no 1p 34 2017

[40] P Prieto M Pineda and M Aguilar ldquoSpectrophotometricquantitation of antioxidant capacity through the formation ofa phosphomolybdenum complex specific application to thedetermination of vitamin Erdquo Analytical Biochemistryvol 269 no 2 pp 337ndash341 1999

[41] D Mukhopadhyay P Dasgupta D S Roy et al ldquoA sensitivein vitro spectrophotometric hydrogen peroxide scavengingassay using 110-phenanthrolinerdquo Free Radicals amp Antioxi-dants vol 6 no 1 2016

[42] L S Borquaye G Darko E Ocansey and E AnkomahldquoAntimicrobial and antioxidant properties of the crude

peptide extracts of Galatea paradoxa and Patella rusticardquoSpringerPlus vol 4 no 1 p 500 2015

[43] L S Borquaye G Darko N Oklu C Anson-Yevu andA Ababio ldquoAntimicrobial and antioxidant activities of ethylacetate and methanol extracts of Littorina littorea andGalateaparadoxardquo Cogent Chemistry vol 2 no 1 article 11618652016

[44] L Peng Y Kawagoe P Hogan and D Delmer ldquoSitosterol-beta- glucoside as primer for cellulose synthesis in plantsrdquoScience vol 295 no 5552 pp 147ndash150 2002

[45] A I Hussain F Anwar S T Hussain Sherazi andR Przybylski ldquoChemical composition antioxidant and an-timicrobial activities of basil (Ocimum basilicum) essential oilsdepends on seasonal variationsrdquo Food Chemistry vol 108no 3 pp 986ndash995 2008

[46] P C Santos-Gomes and M Fernandes-Ferreira ldquoOrgan- andseason-dependent variation in the essential oil composition ofSalvia officinalis L Cultivated at two different sitesrdquo Journal ofAgricultural and Food Chemistry vol 49 no 6 pp 2908ndash2916 2001

[47] W Aidi Wannes B Mhamdi B Marzouk and B MarzoukldquoVariations in essential oil and fatty acid composition duringMyrtus communis var italica fruit maturationrdquo FoodChemistry vol 112 no 3 pp 621ndash626 2009

[48] M Hudaib E Speroni A M Di Pietra and V Cavrini ldquoGCMS evaluation of thyme (Dymus vulgaris L) oil compositionand variations during the vegetative cyclerdquo Journal ofPharmaceutical and Biomedical Analysis vol 29 no 4pp 691ndash700 2002

[49] A M Viljoen S Subramoney S F v Vuuren K H C Baserand B Demirci ldquoe composition geographical variation andantimicrobial activity of Lippia javanica (verbenaceae) leafessential oilsrdquo Journal of Ethnopharmacology vol 96 no 1-2pp 271ndash277 2005

[50] C Demirci and A Studer Encyclopedia of Radicals inChemistry Biology and Materials Vol 2 John Wiley amp SonsChichester UK 2012

[51] M C Foti ldquoAntioxidant properties of phenolsrdquo Journal ofPharmacy and Pharmacology vol 59 no 12 pp 1673ndash16852007

[52] G W Burton T Doba E Gabe et al ldquoAutoxidation of bi-ological molecules 4 Maximizing the antioxidant activity ofphenolsrdquo Journal of the American Chemical Society vol 107no 24 pp 7053ndash7065 1985

Biochemistry Research International 9

Hindawiwwwhindawicom

International Journal of

Volume 2018

Zoology

Hindawiwwwhindawicom Volume 2018

Anatomy Research International

PeptidesInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Journal of Parasitology Research

GenomicsInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawi Publishing Corporation httpwwwhindawicom Volume 2013Hindawiwwwhindawicom

The Scientific World Journal

Volume 2018

Hindawiwwwhindawicom Volume 2018

BioinformaticsAdvances in

Marine BiologyJournal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Neuroscience Journal

Hindawiwwwhindawicom Volume 2018

BioMed Research International

Cell BiologyInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Biochemistry Research International

ArchaeaHindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Genetics Research International

Hindawiwwwhindawicom Volume 2018

Advances in

Virolog y Stem Cells International

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Enzyme Research

Hindawiwwwhindawicom Volume 2018

International Journal of

MicrobiologyHindawiwwwhindawicom

Nucleic AcidsJournal of

Volume 2018

Submit your manuscripts atwwwhindawicom

Hindawiwwwhindawicom

International Journal of

Volume 2018

Zoology

Hindawiwwwhindawicom Volume 2018

Anatomy Research International

PeptidesInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Journal of Parasitology Research

GenomicsInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawi Publishing Corporation httpwwwhindawicom Volume 2013Hindawiwwwhindawicom

The Scientific World Journal

Volume 2018

Hindawiwwwhindawicom Volume 2018

BioinformaticsAdvances in

Marine BiologyJournal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Neuroscience Journal

Hindawiwwwhindawicom Volume 2018

BioMed Research International

Cell BiologyInternational Journal of

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Biochemistry Research International

ArchaeaHindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Genetics Research International

Hindawiwwwhindawicom Volume 2018

Advances in

Virolog y Stem Cells International

Hindawiwwwhindawicom Volume 2018

Hindawiwwwhindawicom Volume 2018

Enzyme Research

Hindawiwwwhindawicom Volume 2018

International Journal of

MicrobiologyHindawiwwwhindawicom

Nucleic AcidsJournal of

Volume 2018

Submit your manuscripts atwwwhindawicom