research article chemical diversity in lippia alba (mill.) n. e....

Research ArticleChemical Diversity in Lippia alba (Mill)N E Brown Germplasm

Arie Fitzgerald Blank1 Liacutedia Cristina Alves Camecirclo1

Maria de Faacutetima Arrigoni-Blank1 Joseacute Baldin Pinheiro2 Thiago Matos Andrade1

Edenilson dos Santos Niculau3 and Peacutericles Barreto Alves3

1Department of Agronomic Engineering Federal University of Sergipe Avenida Marechal Rondon sn49100-000 Sao Cristovao SE Brazil2Escola Superior de Agricultura ldquoLuiz de Queirozrdquo Universidade de Sao Paulo Avenida Padua Dias 11 Vila Independencia13418-900 Piracicaba SP Brazil3Department of Chemistry Federal University of Sergipe Avenida Marechal Rondon sn 49100-000 Sao Cristovao SE Brazil

Correspondence should be addressed to Arie Fitzgerald Blank arieblankgmailcom

Received 30 October 2014 Accepted 27 April 2015

Academic Editor Dun Xian Tan

Copyright copy 2015 Arie Fitzgerald Blank et al This 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 is properlycited

The aim of this study was to perform chemical characterization of Lippia alba accessions from the Active Germplasm Bank ofthe Federal University of Sergipe A randomized block experimental design with two replications was applied The analysis of thechemical composition of the essential oils was conducted using a gas chromatograph coupled to a mass spectrometerThe chemicalcomposition of the essential oils allowed the accessions to be allocated to the following six groups group 1 linalool 18-cineoleand caryophyllene oxide group 2 linalool geranial neral 18-cineol and caryophyllene oxide group 3 limonene carvone andsabinene group 4 carvone limonene g-muurolene and myrcene group 5 neral geranial and caryophyllene oxide and group 6geranial neral o-cymene limonene and caryophyllene oxide

1 Introduction

TheVerbenaceae family consists of approximately 175 generaand 2800 species distributed in tropical and subtropicalregions worldwide and in temperate regions of the southernhemisphere In addition a few species are found in temperateregions of the northern hemisphere [1] The genus Lippiaincludes several plant species of medicinal interest and com-prises approximately 200 shrub species with a pantropicaldistribution and approximately 150 species distributed acrossrupestrian grasslands and tropical savannas (cerrados) inBrazil [2] The species Lippia alba (Mill) NE Brown alsoknown as Lippia geminata HBK and Lantana alba (Mill)is a shrub with a height of approximately 3 meters [3]In traditional Brazilian medicine this species is popularlyknown as lemon balm [4]

This species is considered by some authors [5] to bepromising for use in the pharmaceutical aromatic and

perfumery industries and may also be suitable for theagricultural chemical industry because of its proven antifun-gal insecticidal and repellent properties The essential oilobtained from L alba has been recognized as a potentialsource of several commercially important terpenoid com-pounds [6]

The chemical composition of essential oils consists ofa mixture of many organic compounds in various concen-trations ranging from very low quantities (traces) to majorcompounds Therefore the variability of chemical types is acause for concern from the standpoint of the use of essentialoils as herbal medicines because some compounds maybe unsuitable for achieving a desired result This problemregarding medicinal plants is common in Brazil [7]

Essential oils are primarily produced by the plant leavesand are formed through the secondary metabolism of plantsThe typical compounds of this type include mono- andsesquiterpenes Both the oil composition and plant yield

Hindawi Publishing Corporatione Scientific World JournalVolume 2015 Article ID 321924 11 pageshttpdxdoiorg1011552015321924

2 The Scientific World Journal

including biomass are directly influenced by environmentalfactors which represent a challenge for producers in estab-lishing productive and stable genotypes and maintaining thechemical uniformity demanded by the industry [5]

The rich pharmacological potential of L alba is relatedto the wide chemical variability of its essential oils Thisvariability allows the classification of this species into chemo-types which can be defined according to the major chemicalcomponents of the essential oils [8]The essential oils of somechemotypes identified from L alba differ in their chemicalcomposition with citral carvone and linalool representingthe major components identified [9] The limonene-carvonechemotype is characterized by the presence of limoneneand carvone and the absence of neral and geranial (citral)Limonene is used as a solvent in cleaning products food-stuffs and the cosmetics industry Carvone is used as acarminative and in cosmetic products and has bactericidaland fungicidal properties [10]

The degree of variability in the active ingredient foundin a medicinal species should be very low so that thedrugs produced from that species are safe and effective[8] Therefore the identification and correct classificationof chemotypes which exhibit distinct active ingredients inmedicinal plants are of great importance for maintainingquality planning cultivation and obtaining phytochemicalsthat do not impair usersrsquo health [11]

Thus the aim of this study was to perform chemicalcharacterization of accessions of L alba (Mill) NE Br fromthe Active Germplasm Bank (AGB) of the Federal Universityof Sergipe

2 Materials and Methods

21 Plant Materials The experiment was conducted at theldquoCampus Rural da UFSrdquo experimental farm located in themunicipality of Sao Cristovao state of Sergipe at a latitudeof 11∘001015840 S and longitude of 37∘121015840 W Plants of 48 accessionsof L alba from the AGB at UFS were evaluated (Table 1)

A randomized block experimental design with two repli-cations was employed Each plot consisted of three plantsSpacing of 15 meters was maintained both between indi-vidual plants and between rows The fertilization applied inthe field was 5 kg of cattle manure per pit Culture practicessuch as weeding and hydration were performed whenevernecessary

22 Distillation andAnalysis of Essential Oils Theplantswerecut at a height of 30 cm from the soil and the leaves weredried in an incubator with forced airflow at a temperature of40∘C for five days [12] After drying the leaves were weighedon an electronic scale and essential oils were extracted usingthe hydrodistillation method in a Clevenger apparatus Forhydrodistillation 75 g of dry leaves and 20 L of distilledwater were used per flask and the distillation period was 120minutes after the initiation ofwater vapor condensation in theClevenger apparatus After extraction the essential oils werecollected and stored in a freezer in amber glass vials

Chemical analysis of the essential oil was performed atthe Laboratory of Chromatography of the Department ofChemistry at the Federal University of Sergipe

Qualitative analysis of the chemical composition of theessential oil was performed in a gas chromatograph cou-pled to a mass spectrometer (GC-MS model QP 5050AShimadzu) equipped with an AOC-20i autosampler (Shi-madzu) and a fused-silica capillary column (5 phenyl 95dimethylpolysiloxane 30m times 025mm id and film thick-ness of 025 120583m JampW Scientific) using helium as the carriergas at a flow rate of 12mLminminus1 The temperature rampwas 50∘C for 2min followed by an increase of 4∘Cminminus1until reaching 200∘C then an increase of 15∘C until reaching300∘C afterwhich a constant temperaturewasmaintained for15min The injector temperature was maintained at 250∘Cand that of the detector (or interface) was maintained at280∘C A volume of 05120583L was injected using ethyl acetateThe partition rate of the injected volume was 1 100 and thecolumn pressure was 6420 kPa The MS conditions includedan ion capture detector operated through electron impact andan impact energy of 70 eV a scan rate of 1000 a scan intervalof 050 fragments and a fragmentmass range between 40Daand 500Da

Quantitative analysis of the chemical constituents wasperformed by flame ionization gas chromatography (FID)using a Shimadzu GC-17A (Shimadzu Corporation KyotoJapan) instrument under the following operational condi-tions capillary ZB-5MS column (5 phenyl-arylene-95-dimethylpolysiloxane) fused-silica capillary column (30m times025mm id times 025120583m film thickness) from Phenomenex(Torrance CA USA) under the same conditions as reportedfor the GC-MS Quantification of each constituent was esti-mated by area normalization () Compound concentrationswere calculated from the GC peak areas and they werearranged in order of GC elution

The essential oil components were identified by com-paring their mass spectra with the available spectra in theequipment database (NIST05 and WILEY8) Additionallythe measured retention indices were compared with those inthe literature [13] The relative retention indices (RRI) weredetermined using the van den Dool and Kratz [14] equationand a homologous series of 119899-alkanes (C

8ndashC18) injected

under the chromatography conditions described above

23 Statistical Analysis The data were subjected to varianceanalysis and themeans were compared using the Scott-Knotttest (119901 le 005)The chemical composition data were analyzedthrough twomultivariate analysismethods principal compo-nent analysis (PCA) and arrangement analysis (cluster) basedon the similarity and distribution of the compounds usingStatistica software version 70

3 Results and Discussion

Among the compounds present in the essential oils from 48accessions 33 were identified and are listed according to theirorder of elution (Table 2)

The Scientific World Journal 3

Table 1 Identification and origin of L alba accessions from the Active Germplasm Bank at the Federal University of Sergipe

Accession Municipalitystate Origin UFS herbarium codeLA-01 ABC-Distrito Federal University of Brasılia 14784LA-02 Araguaına-Tocantins University of Brasılia 14785LA-03 Atibaia-Sao Paulo University of Brasılia 13466LA-04 Botucatu-Sao Paulo University of Brasılia 13501LA-08 Brasılia-Distrito Federal University of Brasılia 13475LA-09 Brasılia-Distrito Federal University of Brasılia 14786LA-10 Brasılia-Distrito Federal University of Brasılia 13495LA-13 Fortaleza-Ceara Federal University of Ceara 13488LA-15 Florianopolis-Santa Catarina University of Brasılia 13486LA-17 Brasılia-Distrito Federal University of Brasılia 13494LA-19 Brasılia-Distrito Federal University of Brasılia 13491LA-20 Ilheus-Bahia University of Brasılia 14787LA-21 Brasılia-Distrito Federal University of Brasılia 13493LA-22 Lavras-Minas Gerais University of Brasılia 13476LA-24 Luziania-Goias University of Brasılia 13477LA-27 Piracicaba-Sao Paulo University of Brasılia 13443LA-28 Brasılia-Distrito Federal University of Brasılia 13487LA-29 Planaltina de Goias-Goias University of Brasılia 13485LA-30 Posse-Goias University of Brasılia 13454LA-32 Rio de Janeiro-Rio de Janeiro University of Brasılia 13480LA-36 Brasılia-Distrito Federal University of Brasılia 13472LA-37 Brasılia-Distrito Federal University of Brasılia 13455LA-39 Brasılia-Distrito Federal University of Brasılia 13497LA-40 Brasılia-Distrito Federal University of Brasılia 13456LA-41 Curitiba-Parana University of Brasılia 13484LA-42 Brasılia-Distrito Federal University of Brasılia 13444LA-43 Brasılia-Distrito Federal University of Brasılia 13490LA-44 Brasılia-Distrito Federal University of Brasılia 14788LA-45 Vicosa-Minas Gerais University of Brasılia 13498LA-49 Aracaju-Sergipe Federal University of Sergipe 13471LA-52 Rio Real-Bahia Federal University of Sergipe 13481LA-53 Telha-Sergipe Federal University of Sergipe 13446LA-54 Rio Real-Bahia Federal University of Sergipe 13478LA-55 Rio Real-Bahia Federal University of Sergipe 13468LA-56 Rio Real-Bahia Federal University of Sergipe 13465LA-57 Rio Real-Bahia Federal University of Sergipe 13469LA-58 Rio Real-Bahia Federal University of Sergipe 13482LA-59 Rio Real-Bahia Federal University of Sergipe 13500LA-60 Rio Real-Bahia Federal University of Sergipe 13499LA-61 Rio Real-Bahia Federal University of Sergipe 13479LA-62 Rio Real-Bahia Federal University of Sergipe 13451LA-63 Santana do Sao Francisco-Sergipe Federal University of Sergipe 13445LA-67 Santana do Sao Francisco-Sergipe Federal University of Sergipe 13464LA-68 Santana do Sao Francisco-Sergipe Federal University of Sergipe 14789LA-69 Gararu-Sergipe Federal University of Sergipe 13467LA-70 Cristinapolis-Sergipe Federal University of Sergipe 13473LA-71 Paripiranga-Sergipe Federal University of Sergipe 13447LA-72 Traipu-Alagoas Federal University of Sergipe 13496


Table 2 Chemical composition of the essential oil of L alba accessions from the Active Germplasm Bank at the Federal University of Sergipe

Compound RRI AccessionLA-01 LA-02 LA-03 LA-04 LA-08 LA-09 LA-10 LA-13

120572-thujene 924 000b 000b 043b 027b 000b 000b 000b 000bSabinene 969 000c 000c 000c 015c 000c 064b 000c 439a1-Octen-3-ol 974 000b 000b 000b 028b 072a 000b 000b 000b5-Methyl-6-hepten-2-one 981 000a 000a 046a 041a 034a 000a 000a 000aMyrcene 988 000c 076c 278b 285b 031c 000c 000c 000co-Cymene 1022 000d 000d 011d 032d 000d 000d 000d 000dLimonene 1024 000e 000e 1024c 017e 000e 000e 000e 4535a18-Cineol 1026 722b 000d 000d 000d 000d 922a 000d 000d120574-terpinene 1054 000c 000c 000c 000c 000c 000c 000c 000ccis-sabinene hydrate 1065 000c 000c 000c 000c 000c 000c 000c 000ccis-linalool oxide 1067 086b 000c 000c 000c 000c 120a 000c 000ctrans-linalool oxide 1084 065b 000d 000d 000d 000d 098a 000d 000dLinalool 1095 8473a 084f 089f 109f 095f 8063b 132f 000fPerylene 1102 000b 000b 010a 019a 000b 000b 000b 000b(E)-isocitral 1177 000b 000b 050a 022b 000b 000b 000b 000bMyrtenal 1195 067b 000c 029c 054b 056b 071b 000c 000cNeral 1235 000f 3214a 2978c 3028c 3109c 000f 2932c 000fCarvone 1239 000e 000e 391d 033e 043e 000e 000e 3958cGeraniol 1249 000c 000c 071c 000c 000c 000c 000c 000cGeranial 1264 000f 5405a 4766a 4976a 4945a 000f 4806a 000fMyrtanyl acetate 1324 000d 000d 013c 000d 024c 000d 000d 000dGeranyl acetate 1379 000c 000c 035b 029b 000c 000c 082a 000c120573-elemene 1389 000d 000d 000d 000d 000d 000d 049d 000d120573-caryophyllene 1417 104c 042c 000c 078c 094c 111c 062c 000c120572-guaiene 1437 000d 000d 000d 000d 000d 000d 000d 000d120574-muurolene 1478 062c 000c 029c 000c 000c 052c 000c 000ctrans-calamenene 1521 000b 000b 000b 000b 000b 000b 000b 000bElemol 1548 000d 000d 000d 000d 000d 000d 000d 000dGermacrene B 1559 057b 000c 000c 000c 000c 028c 000c 000c(E)-nerolidol 1561 000e 000e 000e 000e 000e 000e 000e 000eSpathulenol 1577 000e 000e 000e 000e 000e 000e 000e 000eCaryophyllene oxide 1582 293d 1133c 000e 1069c 1424c 366d 1777b 000eHumulene epoxide II 1608 000d 000d 015d 000d 000d 000d 059b 000dEssential oil content () 253a 130d 206c 102d 079e 254a 086e 080e

LA-15 LA-17 LA-19 LA-20 LA-21 LA-22 LA-24 LA-27120572-thujene 924 000b 000b 000b 000b 000b 000b 000b 000bSabinene 969 000c 000c 000c 071b 000c 029c 000c 064b1-Octen-3-ol 974 042a 078a 077a 000b 000b 000b 000b 000b5-Methyl-6-hepten-2-one 981 103a 091a 058a 000a 038a 000a 000a 000aMyrcene 988 307b 067c 045c 076c 084c 000c 000c 021co-Cymene 1022 000d 000d 000d 107d 000d 000d 062d 000dLimonene 1024 000e 000e 000e 000e 000e 000e 000e 000e18-Cineol 1026 000d 000d 000d 662b 093d 917a 238c 783b120574-terpinene 1054 000c 000c 000c 000c 000c 000c 000c 000ccis-sabinene hydrate 1065 000c 000c 000c 000c 000c 000c 000c 000c


Table 2 Continued

cis-linalool oxide 1067 000c 000c 000c 064b 000c 100a 000c 080btrans-linalool oxide 1084 000d 000d 000d 000d 000d 023c 000d 061bLinalool 1095 083f 143f 083f 5769d 727f 8445a 4938e 7579cPerylene 1102 000b 000b 000b 000b 000b 000b 000b 000b(E)-isocitral 1177 000b 000b 000b 000b 000b 000b 000b 000bMyrtenal 1195 000c 000c 095a 000c 034c 000c 000c 066bNeral 1235 3198a 2891c 3122c 1151e 2898c 000f 1659e 058fCarvone 1239 000e 000e 000e 000e 043e 000e 000e 000eGeraniol 1249 000c 000c 000c 000c 000c 000c 000c 000cGeranial 1264 5054a 4868a 4909a 1699e 4491a 000f 2618e 083fMyrtanyl acetate 1324 000d 000d 053b 000d 000d 000d 000d 000dGeranyl acetate 1379 000c 000c 000c 000c 000c 000c 000c 000c120573-elemene 1389 000d 025d 000d 000d 000d 000d 000d 046d120573-caryophyllene 1417 175b 103c 089c 083c 071c 029c 074c 159b120572-guaiene 1437 000d 000d 000d 000d 000d 000d 000d 000d120574-muurolene 1478 000c 000c 000c 000c 000c 000c 000c 160btrans-calamenene 1521 000b 000b 000b 000b 000b 000b 000b 000bElemol 1548 000d 000d 000d 000d 000d 000d 000d 000dGermacrene B 1559 000c 000c 000c 000c 000c 000c 000c 126a(E)-nerolidol 1561 000e 000e 000e 000e 000e 000e 000e 000eSpathulenol 1577 000e 000e 000e 000e 000e 000e 000e 000eCaryophyllene oxide 1582 1035c 1686b 1404c 318d 1463c 435d 411d 000eHumulene epoxide II 1608 000d 000d 000d 000d 029c 020c 000d 000dEssential oil content () 109d 104d 089e 133d 076e 253a 250a 226b

LA-28 LA-29 LA-30 LA-32 LA-36 LA-37 LA-39 LA-40120572-thujene 924 000b 000b 000b 091a 000b 000b 000b 022bSabinene 969 000c 000c 027c 000c 024c 000c 053b 027c1-Octen-3-ol 974 063a 000b 000b 031b 000b 119a 000b 063a5-Methyl-6-hepten-2-one 981 000a 000a 072a 023a 046a 000a 035a 052aMyrcene 988 000c 709a 040c 367b 017c 000c 020c 116co-Cymene 1022 000d 000d 371d 1236a 396c 000d 530c 000dLimonene 1024 000e 000e 708c 000e 680c 000e 855c 000e18-Cineol 1026 000d 000d 000d 000d 000d 000d 000d 000d120574-terpinene 1054 000c 000c 105a 000c 103a 000c 101a 000ccis-sabinene hydrate 1065 000c 000c 000c 000c 000c 000c 000c 029bcis-linalool oxide 1067 000c 000c 000c 000c 000c 000c 000c 030ctrans-linalool oxide 1084 000d 000d 000d 000d 000d 000d 000d 000dLinalool 1095 091f 000f 092f 025f 085f 000f 092f 290fPerylene 1102 000b 000b 000b 000b 000b 000b 000b 000b(E)-isocitral 1177 000b 000b 000b 000b 034a 000b 057a 000bMyrtenal 1195 072b 067b 000c 049b 000c 119a 000c 000cNeral 1235 3199a 2809c 3293a 2194c 3087c 2376c 3166a 2995cCarvone 1239 000e 056e 093e 039e 099e 116e 105e 000eGeraniol 1249 000c 000c 000c 203b 000c 000c 000c 000cGeranial 1264 4973a 4024c 4907a 3290c 5132a 3989c 4800a 4680aMyrtanyl acetate 1324 000d 000d 000d 000d 000d 072a 000d 000dGeranyl acetate 1379 000c 000c 000c 000c 000c 000c 000c 000c120573-elemene 1389 000d 119b 000d 000d 000d 000d 000d 188a120573-caryophyllene 1417 055c 000c 000c 369a 000c 154b 000c 131b


Table 2 Continued

120572-guaiene 1437 000d 000d 000d 000d 000d 000d 000d 000d120574-muurolene 1478 000c 000c 041c 000c 040c 000c 000c 000ctrans-calamenene 1521 000b 000b 000b 000b 000b 000b 000b 000bElemol 1548 000d 000d 114c 000d 216a 000d 183a 000dGermacrene B 1559 000c 000c 000c 000c 000c 000c 000c 000c(E)-nerolidol 1561 000e 000e 114d 000e 216a 000e 183b 000eSpathulenol 1577 000e 000e 000e 000e 000e 000e 000e 000eCaryophyllene oxide 1582 1486c 1089c 132e 2046b 000e 2809a 000e 1143cHumulene epoxide II 1608 000d 000d 000d 035c 000d 000d 000d 000dEssential oil content () 058e 066e 106d 126d 221b 080e 184c 053e

LA-41 LA-42 LA-43 LA-44 LA-45 LA-49 LA-52 LA-53120572-thujene 924 000b 000b 000b 000b 000b 000b 000b 000bSabinene 969 014c 028c 031c 000c 098b 057b 054b 017c1-Octen-3-ol 974 063a 044a 000b 058a 000b 021b 000b 059a5-Methyl-6-hepten-2-one 981 074a 000a 043a 051a 030a 026a 030a 034aMyrcene 988 147c 204c 071c 042c 847a 000c 021c 000co-Cymene 1022 031d 000d 000d 000d 032d 1150a 944b 449cLimonene 1024 000e 000e 746c 000e 000e 000e 386d 000e18-Cineol 1026 000d 000d 000d 000d 000d 000d 000d 000d120574-terpinene 1054 000c 000c 000c 000c 000c 000c 098a 000ccis-sabinene hydrate 1065 000c 000c 000c 000c 046b 000c 000c 033bcis-linalool oxide 1067 015c 000c 000c 000c 000c 027c 000c 000ctrans-linalool oxide 1084 000d 000d 000d 000d 000d 000d 000d 000dLinalool 1095 085f 222f 074f 073f 133f 033f 000f 057fPerylene 1102 000b 000b 000b 000b 000b 000b 000b 000b(E)-isocitral 1177 000b 000b 075a 000b 038a 000b 046a 000bMyrtenal 1195 000c 000c 000c 068b 000c 000c 000c 000cNeral 1235 3088c 3133c 3486a 3227a 2857c 2369c 2997c 3157aCarvone 1239 000e 000e 356d 000e 000e 000e 000e 000eGeraniol 1249 000c 000c 000c 000c 338a 000c 000c 000cGeranial 1264 4869a 4859a 5118a 4988a 4636a 3939c 4622a 4837aMyrtanyl acetate 1324 000d 000d 000d 050b 000d 000d 000d 000dGeranyl acetate 1379 027b 000c 000c 000c 040b 103a 000c 000c120573-elemene 1389 079c 175a 000d 000d 000d 000d 000d 000d120573-caryophyllene 1417 088c 123c 000c 000c 284a 115c 160b 000c120572-guaiene 1437 000d 000d 000d 000d 000d 000d 000d 166b120574-muurolene 1478 000c 000c 000c 000c 033c 038c 000c 000ctrans-calamenene 1521 000b 000b 000b 000b 000b 000b 000b 000bElemol 1548 000d 000d 000d 000d 000d 000d 000d 000dGermacrene B 1559 000c 000c 000c 000c 000c 000c 000c 000c(E)-nerolidol 1561 000e 000e 000e 000e 000e 000e 000e 000eSpathulenol 1577 000e 000e 000e 000e 000e 000e 000e 321aCaryophyllene oxide 1582 1246c 1166c 000e 1343c 537d 1989b 605d 505dHumulene epoxide II 1608 000d 000d 000d 000d 000d 066b 034c 145aEssential oil content () 085e 090e 180c 069e 106d 118d 200c 076e

LA-54 LA-55 LA-56 LA-57 LA-58 LA-59 LA-60 LA-61120572-thujene 924 000b 000b 000b 000b 000b 000b 000b 000b


Table 2 Continued

Sabinene 969 059b 053b 000c 000c 000c 025c 000c 000c1-Octen-3-ol 974 000b 000b 000b 000b 067a 052a 000b 000b5-Methyl-6-hepten-2-one 981 000a 000a 000a 000a 065a 092a 000a 053aMyrcene 988 000c 000c 017c 015c 127c 280b 000c 131co-Cymene 1022 955b 829b 000d 000d 293c 377c 647b 353cLimonene 1024 397d 369d 1848b 1935b 000e 000e 260e 000e18-Cineol 1026 000d 000d 000d 000d 000d 000d 000d 000d120574-terpinene 1054 090a 093a 000c 000c 000c 000c 085a 000ccis-sabinene hydrate 1065 000c 000c 000c 000c 000c 022c 000c 000ccis-linalool oxide 1067 000c 000c 000c 000c 000c 000c 000c 000ctrans-linalool oxide 1084 000d 000d 000d 000d 000d 000d 000d 000dLinalool 1095 000f 000f 032f 019f 283f 231f 000f 230fPerylene 1102 000b 000b 000b 000b 014a 013a 000b 000b(E)-isocitral 1177 085a 044a 000b 000b 000b 000b 000b 000bMyrtenal 1195 000c 000c 000c 000c 000c 000c 000c 000cNeral 1235 2999c 3098c 000f 000f 3320a 3393a 3346a 3531aCarvone 1239 000e 000e 7774a 7720a 000e 000e 000e 000eGeraniol 1249 000c 000c 000c 000c 000c 000c 000c 000cGeranial 1264 4402a 4727a 000f 000f 5142a 5135a 4861a 5286aMyrtanyl acetate 1324 000d 000d 000d 000d 000d 000d 000d 000dGeranyl acetate 1379 000c 000c 000c 000c 101a 083a 000c 083a120573-elemene 1389 000d 000d 000d 000d 000d 000d 000d 000d120573-caryophyllene 1417 218b 188b 000c 000c 000c 000c 316a 000c120572-guaiene 1437 000d 000d 000d 000d 000d 000d 000d 000d120574-muurolene 1478 000c 000c 199b 195b 000c 000c 000c 000ctrans-calamenene 1521 000b 000b 000b 000b 000b 000b 000b 000bElemol 1548 000d 000d 000d 000d 000d 000d 000d 000dGermacrene B 1559 000c 000c 000c 000c 000c 000c 000c 000c(E)-nerolidol 1561 000e 000e 000e 000e 000e 000e 000e 000eSpathulenol 1577 000e 000e 000e 000e 000e 000e 000e 000eCaryophyllene oxide 1582 754d 596d 000e 000e 500d 259d 485d 300dHumulene epoxide II 1608 038c 000d 000d 000d 087b 036c 000d 031cEssential oil content () 193c 233b 160c 266a 066e 100d 173c 066e

LA-62 LA-63 LA-67 LA-68 LA-69 LA-70 LA-71 LA-72120572-thujene 924 000b 025b 000b 000b 000b 000b 024b 000bSabinene 969 000c 075b 000c 081b 037b 000c 055b 051b1-Octen-3-ol 974 000b 059a 000b 000b 034b 000b 000b 017b5-Methyl-6-hepten-2-one 981 046a 085a 000a 044a 081a 000a 028a 101aMyrcene 988 507b 000c 000c 000c 000c 340b 020c 000co-Cymene 1022 000d 897b 461c 1033a 1186a 000d 1139a 081dLimonene 1024 914c 000e 798c 028e 000e 1981b 421d 000e18-Cineol 1026 000d 000d 000d 000d 000d 000d 000d 000d120574-terpinene 1054 000c 000c 086a 000c 000c 000c 047a 000ccis-sabinene hydrate 1065 000c 061a 000c 073a 035b 000c 000c 074acis-linalool oxide 1067 000c 000c 000c 000c 000c 000c 000c 000ctrans-linalool oxide 1084 000d 000d 000d 000d 000d 000d 000d 000dLinalool 1095 058f 099f 043f 106f 063f 069f 027f 048fPerylene 1102 000b 000b 000b 000b 000b 000b 000b 000b


Table 2 Continued

(E)-isocitral 1177 063a 098a 044a 000b 024b 000b 077a 058aMyrtenal 1195 000c 000c 000c 000c 000c 000c 000c 000cNeral 1235 3136c 2946c 3328a 2734c 2905c 000f 2794c 3614aCarvone 1239 527d 000e 106e 000e 029e 7273b 000e 000eGeraniol 1249 000c 000c 000c 000c 000c 000c 000c 000cGeranial 1264 4611a 4512a 4953a 4536a 4521a 000f 4206c 5463aMyrtanyl acetate 1324 000d 000d 000d 000d 000d 000d 000d 000dGeranyl acetate 1379 000c 000c 000c 000c 000c 000c 000c 064a120573-elemene 1389 000d 000d 000d 000d 000d 000d 000d 000d120573-caryophyllene 1417 039c 000c 000c 000c 000c 000c 120c 000c120572-guaiene 1437 000d 136c 000d 289a 158b 000d 000d 000d120574-muurolene 1478 000c 000c 026c 000c 000c 257a 000c 000ctrans-calamenene 1521 000b 000b 000b 000b 000b 000b 000b 124aElemol 1548 000d 000d 154b 000d 000d 000d 000d 000dGermacrene B 1559 000c 000c 000c 000c 000c 000c 000c 000c(E)-nerolidol 1561 000e 000e 154c 000e 000e 000e 000e 000eSpathulenol 1577 000e 285b 000e 259c 182d 000e 000e 000eCaryophyllene oxide 1582 099e 410d 000e 358d 459d 000e 928c 157eHumulene epoxide II 1608 000d 117a 000d 133a 036c 000d 071b 000dEssential oil content () 159c 066e 280a 123d 117d 195c 146d 120dRRI relative retention index Means followed by different letters in each row were significantly different by the Scott-Knott test (119901 lt 005)

0 900800700600500400300200100Euclidean distance

LA-69LA-68LA-63LA-71LA-54LA-55LA-52LA-72LA-61LA-59LA-58LA-60LA-53LA-43LA-36LA-39LA-67LA-30LA-62LA-03LA-37LA-49LA-32LA-45LA-29LA-21LA-17LA-10LA-44LA-28LA-19LA-08LA-42LA-41LA-40LA-15LA-04LA-02LA-70LA-57LA-56LA-13LA-24LA-20LA-27LA-09LA-22LA-01

Lipp

ia a

lba

acce

ssio

ns

Cluster 1

Cluster 2Cluster 3

Cluster 4

Cluster 5

Cluster 6

Figure 1 Two-dimensional dendrogram showing the similarity of the chemical compositions of 48 L alba accessions obtained from theActive Germplasm Bank at the Federal University of Sergipe


120572-th

ujen

eSa

bine

ne1-

Oct

en-3

-ol

5-M

ethy

l-6-h

epte

n-2-

one

Myr

cene

o-Cy

men

eLi

mon

ene

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Tran

s-ca

lam

enen

eEl

emol

Ger

mac

rene

B(E

)-ne

rolid

olSp

athu

leno

lCa

ryop

hylle

ne o

xide

Hum

ulen

e epo

xide

II

0

20

40

60

80

100Cluster 1

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

()

(a)

Cluster 2

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(b)

Cluster 3

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(c)

Cluster 4

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(d)

Cluster 5

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(e)

Cluster 6

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(f)

Figure 2 Means and SEM for the chemical compounds in the essential oils from clusters 1 through 6 of L alba accessions

The variation in the concentrations of compounds amongthe accessions may have been a consequence of their originconsidering that in this experiment all of the accessionswere grown in the same environment Similar results wereobserved previously in studies with three chemotypes of Lalba from different Brazilian states (Rio de Janeiro Cearaand Sao Paulo) [15] and with accessions of Pogostemon spfrom the Active Germplasm Bank of the Federal Universityof Sergipe [16]

The chemical analysis (Table 2) indicated that the mostabundant compounds among the accessions were 18-cineolelinalool myrcene limonene carvone geranial and neralleading to the formation of six clusters according to theobtained chemical compositions which were differentiated

through cluster analysis (Figure 1) The compound linaloolpresent in accessions LA-01 and LA-22 (8473 and 8445resp) showed the highest abundance A similar result wasreported by [17] Linalool is widely used in the perfumecosmetic and fragrance industries [12]

Considering the similarities of the chemical constituentsof the essential oils of these 48 accessions the clusters wereclassified as follows Cluster 1 included LA-01 LA-09 LA-22and LA-27 which contained the followingmajor compoundslinalool 18-cineole and caryophyllene oxide Cluster 2 wasformed by accessions LA-20 and LA-24 and comprised thefollowing major compounds linalool geranial neral 18-cineole and caryophyllene oxide Cluster 3 was formedby accession LA-13 with the following major compounds


Geranyl acetate

Perylene

120572-thujene

Myrcene

Myrtanyl acetate

120573-elemene

120573-caryophyllene

Germacrene B

Trans-linalool oxide cis-li

naloo

l oxid

e

Linalool

18-Cineol

Myrtenal

(E)-nerolidol

1-Octen-3-ol

Caryophyllene oxide

Geraniol

120574-muurolene

Carvone

Limonene

SabineneElemol

Spathulenol

(E)-isocitral

o-Cymene

Humulene epoxide II cis-sabinene hydrate

120572-guaiene

120574-terpinene

Trans-calamenene

minus10

minus08

minus06

minus04

minus02

00

02

04

06

08

10

First principal component (2055)minus10 minus08 minus06 minus04 minus02 00 02 04 06 08 10

Seco

nd p

rinci

pal c

ompo

nent

(1239

)

Geranial

Neral5-methyl-6-hepten-2-one

Figure 3 Distribution of chemical compounds in the essential oils of L alba in relation to the first and second principal components basedon the principal component analysis (PCA)

limonene carvone and sabinene Cluster 4 comprised acces-sions LA-56 LA-57 and LA-70 with the following majorcompounds carvone limonene g-muurolene and myrceneCluster 5 was formed by accessions LA-02 LA-04 LA-08 LA-10 LA-15 LA-17 LA-19 LA-21 LA-28 LA-29 LA-32 LA-37 LA-40 LA-41 LA-42 LA-44 LA-45 and LA-49 and exhibited the following major compounds neralgeranial and caryophyllene oxide Cluster 6 consisted ofaccessions LA-03 LA-30 LA-36 LA-39 LA-43 LA-52 LA-53 LA-54 LA-55 LA-58 LA-59 LA-60 LA-61 LA-62 LA-63 LA-67 LA-68 LA-69 LA-71 and LA-72 which containedgeranial neral o-cymene limonene and caryophyllene oxide(Figure 2)

According to the PCA (Figure 3) the first principalcomponent accounted for 2055 of the total variability inthe data and was positively associated with 18-cineol (119903 =082) cis-linalool oxide (119903 = 079) linalool (119903 = 082) andtrans-linalool oxide (119903 = 077) and negatively associated withgeranial (119903 = 090) and neral (119903 = minus089)

The second principal component represented 1239of the total variation in the data and showed a positivecorrelation with 1-octen-3-ol (119903 = 060) myrtenal (119903 = 069)myrtanyl acetate (119903 = 054) and caryophyllene oxide (119903 =075) and a negative correlation with carvone (119903 = minus049) andlimonene (119903 = minus063)

4 Conclusions

Variability was observed in the chemical composition of theessential oils of L alba accessions obtained from the AGB atUFS resulting in the formation of six different groups

The compounds characterizing the six groups were as fol-lows group 1 linalool 18-cineole and caryophyllene oxidegroup 2 linalool geranial neral 18-cineol and caryophyl-lene oxide group 3 limonene carvone and sabinene group4 carvone limonene g-muurolene and myrcene group 5neral geranial and caryophyllene oxide and group 6 gera-nial neral o-cymene limonene and caryophyllene oxide

The most abundant compounds were 18-cineol linaloolmyrcene limonene carvone geranial and neral

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

The authors are grateful to FAPITECSE CNPq CAPES andETENEBNB for their financial support of this work andto Professors Jean Kleber de Abreu Mattos (University of


Brasılia) and Renato Innecco (Federal University of Ceara)for the donation of L alba accessions

References

[1] S L Goulart and C R Marcati ldquoComparative wood anatomyof root and stem of Lippia salviifolia Cham (Verbenaceae)rdquoRevista Brasileira de Botanica vol 31 no 2 pp 263ndash275 2008

[2] F R G Salimena ldquoNovos sinonimos e tipificacao em Lippiasect Rhodolippia (Verbenaceae)rdquo Darwiniana vol 40 pp 121ndash125 2002

[3] E E Stashenko B E Jaramillo and J RMartınez ldquoComparisonof different extraction methods for the analysis of volatilesecondary metabolites of Lippia alba (Mill) NE Brown grownin Colombia and evaluation of its in vitro antioxidant activityrdquoJournal of Chromatography A vol 1025 no 1 pp 93ndash103 2004

[4] J G S Filho J G Melo A M Saraiva A M GoncalvesM N Psiottano and H S Xavier ldquoAntimicrobial activity andphytochemical profile from the roots of Lippia alba (Mill) NEBrownrdquo Revista Brasileira de Farmacognosia vol 16 no 4 pp506ndash509 2006

[5] P Y Yamamoto C A Colombo J A Azevedo Filho et alldquoPerformance of ginger grass (Lippia alba) for traits related tothe production of essential oilrdquo Scientia Agricola vol 65 no 5pp 481ndash489 2008

[6] S K Gupta S P S Khanuja and S Kumar ldquoIn vitro micro-propagation of Lippia albardquo Current Science vol 81 no 2 pp206ndash210 2001

[7] H Jannuzzi J K A Mattos R F Vieira D B Silva H R Bizzoand L A M Gracindo ldquoAvaliacao agronomica e identificacaode quimiotipos de erva cidreira no Distrito Federalrdquo Horticul-tura Brasileira vol 28 no 4 pp 412ndash417 2010

[8] SM Souza Bandeamento cromossomico em Lippia alba UFLALavras Brazil 2006

[9] L Juliao E Tavares C Lage and S Leitao ldquoCromatografiaem camada fina de extratos de tres quimiotipos de Lippia alba(Mill) NEBr (erva-cidreira)rdquo Revista Brasileira de Farmacog-nosia vol 13 pp 36ndash38 2003

[10] M R A Santos R Innecco and C F Fernandes Efeitosda altura de corte de erva-cidreira (Lippia alba) na producaode biomassa e oleo essencial vol 35 Boletim de pesquisa edesenvolvimentoEMBAPA Rondonia 2006

[11] M E Pascual K Slowing E Carretero D SanchezMata andAVillar ldquoLippia traditional uses chemistry and pharmacology areviewrdquo Journal of Ethnopharmacology vol 76 no 3 pp 201ndash214 2001

[12] J L S Carvalho Filho A F Blank P B Alves et al ldquoInfluenceof the harvesting time temperature and drying period onbasil (Ocimum basilicum L) essential oilrdquo Revista Brasileira deFarmacognosia vol 16 pp 24ndash30 2006

[13] R P Adams Identification of Essential Oil Components by GasChromatographyMass Spectrometry Allured Publishing CarolStream Ill USA 2007

[14] H van den Dool and P D Kratz ldquoA generalization of the reten-tion index system including liner temperature programmedgas-liquid partition chromatographyrdquo Journal of Chromatogra-phy vol 11 pp 463ndash471 1963

[15] E S Tavares L S Juliao D Lopes H R Bizzo C L SLage and S G Leitao ldquoAnalise do oleo essencial de folhas detres quimiotipos de Lippia alba (Mill) N E Br (Verbenaceae)cultivados em condicoes semelhantesrdquo Revista Brasileira deFarmacognosia vol 15 no 1 pp 1ndash5 2005

[16] A F Blank T C P Santrsquoana P S Santos et al ldquoChemicalcharacterization of the essential oil from patchouli accessionsharvested over four seasonsrdquo Industrial Crops and Products vol34 no 1 pp 831ndash837 2011

[17] D Lorenzo D Paz P Davies R Vila S Caigueral and EDellacassa ldquoComposition of a new essential oil type of Lippiaalba (Mill) NE Brown from Uruguayrdquo Flavour and FragranceJournal vol 16 no 5 pp 356ndash359 2001

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Evolutionary BiologyInternational Journal of



including biomass are directly influenced by environmentalfactors which represent a challenge for producers in estab-lishing productive and stable genotypes and maintaining thechemical uniformity demanded by the industry [5]

The rich pharmacological potential of L alba is relatedto the wide chemical variability of its essential oils Thisvariability allows the classification of this species into chemo-types which can be defined according to the major chemicalcomponents of the essential oils [8]The essential oils of somechemotypes identified from L alba differ in their chemicalcomposition with citral carvone and linalool representingthe major components identified [9] The limonene-carvonechemotype is characterized by the presence of limoneneand carvone and the absence of neral and geranial (citral)Limonene is used as a solvent in cleaning products food-stuffs and the cosmetics industry Carvone is used as acarminative and in cosmetic products and has bactericidaland fungicidal properties [10]

The degree of variability in the active ingredient foundin a medicinal species should be very low so that thedrugs produced from that species are safe and effective[8] Therefore the identification and correct classificationof chemotypes which exhibit distinct active ingredients inmedicinal plants are of great importance for maintainingquality planning cultivation and obtaining phytochemicalsthat do not impair usersrsquo health [11]

Thus the aim of this study was to perform chemicalcharacterization of accessions of L alba (Mill) NE Br fromthe Active Germplasm Bank (AGB) of the Federal Universityof Sergipe

2 Materials and Methods

21 Plant Materials The experiment was conducted at theldquoCampus Rural da UFSrdquo experimental farm located in themunicipality of Sao Cristovao state of Sergipe at a latitudeof 11∘001015840 S and longitude of 37∘121015840 W Plants of 48 accessionsof L alba from the AGB at UFS were evaluated (Table 1)

A randomized block experimental design with two repli-cations was employed Each plot consisted of three plantsSpacing of 15 meters was maintained both between indi-vidual plants and between rows The fertilization applied inthe field was 5 kg of cattle manure per pit Culture practicessuch as weeding and hydration were performed whenevernecessary

22 Distillation andAnalysis of Essential Oils Theplantswerecut at a height of 30 cm from the soil and the leaves weredried in an incubator with forced airflow at a temperature of40∘C for five days [12] After drying the leaves were weighedon an electronic scale and essential oils were extracted usingthe hydrodistillation method in a Clevenger apparatus Forhydrodistillation 75 g of dry leaves and 20 L of distilledwater were used per flask and the distillation period was 120minutes after the initiation ofwater vapor condensation in theClevenger apparatus After extraction the essential oils werecollected and stored in a freezer in amber glass vials

Chemical analysis of the essential oil was performed atthe Laboratory of Chromatography of the Department ofChemistry at the Federal University of Sergipe

Qualitative analysis of the chemical composition of theessential oil was performed in a gas chromatograph cou-pled to a mass spectrometer (GC-MS model QP 5050AShimadzu) equipped with an AOC-20i autosampler (Shi-madzu) and a fused-silica capillary column (5 phenyl 95dimethylpolysiloxane 30m times 025mm id and film thick-ness of 025 120583m JampW Scientific) using helium as the carriergas at a flow rate of 12mLminminus1 The temperature rampwas 50∘C for 2min followed by an increase of 4∘Cminminus1until reaching 200∘C then an increase of 15∘C until reaching300∘C afterwhich a constant temperaturewasmaintained for15min The injector temperature was maintained at 250∘Cand that of the detector (or interface) was maintained at280∘C A volume of 05120583L was injected using ethyl acetateThe partition rate of the injected volume was 1 100 and thecolumn pressure was 6420 kPa The MS conditions includedan ion capture detector operated through electron impact andan impact energy of 70 eV a scan rate of 1000 a scan intervalof 050 fragments and a fragmentmass range between 40Daand 500Da

Quantitative analysis of the chemical constituents wasperformed by flame ionization gas chromatography (FID)using a Shimadzu GC-17A (Shimadzu Corporation KyotoJapan) instrument under the following operational condi-tions capillary ZB-5MS column (5 phenyl-arylene-95-dimethylpolysiloxane) fused-silica capillary column (30m times025mm id times 025120583m film thickness) from Phenomenex(Torrance CA USA) under the same conditions as reportedfor the GC-MS Quantification of each constituent was esti-mated by area normalization () Compound concentrationswere calculated from the GC peak areas and they werearranged in order of GC elution

The essential oil components were identified by com-paring their mass spectra with the available spectra in theequipment database (NIST05 and WILEY8) Additionallythe measured retention indices were compared with those inthe literature [13] The relative retention indices (RRI) weredetermined using the van den Dool and Kratz [14] equationand a homologous series of 119899-alkanes (C

8ndashC18) injected

under the chromatography conditions described above

23 Statistical Analysis The data were subjected to varianceanalysis and themeans were compared using the Scott-Knotttest (119901 le 005)The chemical composition data were analyzedthrough twomultivariate analysismethods principal compo-nent analysis (PCA) and arrangement analysis (cluster) basedon the similarity and distribution of the compounds usingStatistica software version 70

3 Results and Discussion

Among the compounds present in the essential oils from 48accessions 33 were identified and are listed according to theirorder of elution (Table 2)










Table 2 Continued




Table 2 Continued





Table 2 Continued




Table 2 Continued




Lipp

ia a

lba

acce

ssio

ns

Cluster 1

Cluster 2Cluster 3

Cluster 4

Cluster 5

Cluster 6



120572-th

ujen

eSa

bine

ne1-

Oct

en-3

-ol

5-M

ethy

l-6-h

epte

n-2-

one

Myr

cene

o-Cy

men

eLi

mon

ene

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Tran

s-ca

lam

enen

eEl

emol

Ger

mac

rene

B(E

)-ne

rolid

olSp

athu

leno

lCa

ryop

hylle

ne o

xide

Hum

ulen

e epo

xide

II

0

20

40

60

80

100Cluster 1

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

()

(a)

Cluster 2

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(b)

Cluster 3

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(c)

Cluster 4

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(d)

Cluster 5

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(e)

Cluster 6

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(f)







Geranyl acetate

Perylene

120572-thujene

Myrcene

Myrtanyl acetate

120573-elemene


Germacrene B


naloo

l oxid

e

Linalool

18-Cineol

Myrtenal

(E)-nerolidol

1-Octen-3-ol

Caryophyllene oxide

Geraniol

120574-muurolene

Carvone

Limonene

SabineneElemol

Spathulenol

(E)-isocitral

o-Cymene


120572-guaiene

120574-terpinene

Trans-calamenene

minus10

minus08

minus06

minus04

minus02

00

02

04

06

08

10


Seco

nd p

rinci

pal c

ompo

nent

(1239

)

Geranial






4 Conclusions






Acknowledgments




References




















Journal of




Agronomy





Microbiology




Volume 2014

































Table 2 Continued




Table 2 Continued





Table 2 Continued




Table 2 Continued




Lipp

ia a

lba

acce

ssio

ns

Cluster 1

Cluster 2Cluster 3

Cluster 4

Cluster 5

Cluster 6



120572-th

ujen

eSa

bine

ne1-

Oct

en-3

-ol

5-M

ethy

l-6-h

epte

n-2-

one

Myr

cene

o-Cy

men

eLi

mon

ene

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Tran

s-ca

lam

enen

eEl

emol

Ger

mac

rene

B(E

)-ne

rolid

olSp

athu

leno

lCa

ryop

hylle

ne o

xide

Hum

ulen

e epo

xide

II

0

20

40

60

80

100Cluster 1

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

()

(a)

Cluster 2

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(b)

Cluster 3

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(c)

Cluster 4

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(d)

Cluster 5

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(e)

Cluster 6

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(f)







Geranyl acetate

Perylene

120572-thujene

Myrcene

Myrtanyl acetate

120573-elemene


Germacrene B


naloo

l oxid

e

Linalool

18-Cineol

Myrtenal

(E)-nerolidol

1-Octen-3-ol

Caryophyllene oxide

Geraniol

120574-muurolene

Carvone

Limonene

SabineneElemol

Spathulenol

(E)-isocitral

o-Cymene


120572-guaiene

120574-terpinene

Trans-calamenene

minus10

minus08

minus06

minus04

minus02

00

02

04

06

08

10


Seco

nd p

rinci

pal c

ompo

nent

(1239

)

Geranial






4 Conclusions






Acknowledgments




References




















Journal of




Agronomy





Microbiology




Volume 2014

























Table 2 Continued





Table 2 Continued




Table 2 Continued




Lipp

ia a

lba

acce

ssio

ns

Cluster 1

Cluster 2Cluster 3

Cluster 4

Cluster 5

Cluster 6



120572-th

ujen

eSa

bine

ne1-

Oct

en-3

-ol

5-M

ethy

l-6-h

epte

n-2-

one

Myr

cene

o-Cy

men

eLi

mon

ene

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Tran

s-ca

lam

enen

eEl

emol

Ger

mac

rene

B(E

)-ne

rolid

olSp

athu

leno

lCa

ryop

hylle

ne o

xide

Hum

ulen

e epo

xide

II

0

20

40

60

80

100Cluster 1

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

()

(a)

Cluster 2

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(b)

Cluster 3

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(c)

Cluster 4

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(d)

Cluster 5

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(e)

Cluster 6

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(f)







Geranyl acetate

Perylene

120572-thujene

Myrcene

Myrtanyl acetate

120573-elemene


Germacrene B


naloo

l oxid

e

Linalool

18-Cineol

Myrtenal

(E)-nerolidol

1-Octen-3-ol

Caryophyllene oxide

Geraniol

120574-muurolene

Carvone

Limonene

SabineneElemol

Spathulenol

(E)-isocitral

o-Cymene


120572-guaiene

120574-terpinene

Trans-calamenene

minus10

minus08

minus06

minus04

minus02

00

02

04

06

08

10


Seco

nd p

rinci

pal c

ompo

nent

(1239

)

Geranial






4 Conclusions






Acknowledgments




References




















Journal of




Agronomy





Microbiology




Volume 2014

























Table 2 Continued




Table 2 Continued




Lipp

ia a

lba

acce

ssio

ns

Cluster 1

Cluster 2Cluster 3

Cluster 4

Cluster 5

Cluster 6



120572-th

ujen

eSa

bine

ne1-

Oct

en-3

-ol

5-M

ethy

l-6-h

epte

n-2-

one

Myr

cene

o-Cy

men

eLi

mon

ene

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Tran

s-ca

lam

enen

eEl

emol

Ger

mac

rene

B(E

)-ne

rolid

olSp

athu

leno

lCa

ryop

hylle

ne o

xide

Hum

ulen

e epo

xide

II

0

20

40

60

80

100Cluster 1

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

()

(a)

Cluster 2

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(b)

Cluster 3

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(c)

Cluster 4

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(d)

Cluster 5

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(e)

Cluster 6

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(f)







Geranyl acetate

Perylene

120572-thujene

Myrcene

Myrtanyl acetate

120573-elemene


Germacrene B


naloo

l oxid

e

Linalool

18-Cineol

Myrtenal

(E)-nerolidol

1-Octen-3-ol

Caryophyllene oxide

Geraniol

120574-muurolene

Carvone

Limonene

SabineneElemol

Spathulenol

(E)-isocitral

o-Cymene


120572-guaiene

120574-terpinene

Trans-calamenene

minus10

minus08

minus06

minus04

minus02

00

02

04

06

08

10


Seco

nd p

rinci

pal c

ompo

nent

(1239

)

Geranial






4 Conclusions






Acknowledgments




References




















Journal of




Agronomy





Microbiology




Volume 2014

























Table 2 Continued




Lipp

ia a

lba

acce

ssio

ns

Cluster 1

Cluster 2Cluster 3

Cluster 4

Cluster 5

Cluster 6



120572-th

ujen

eSa

bine

ne1-

Oct

en-3

-ol

5-M

ethy

l-6-h

epte

n-2-

one

Myr

cene

o-Cy

men

eLi

mon

ene

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Tran

s-ca

lam

enen

eEl

emol

Ger

mac

rene

B(E

)-ne

rolid

olSp

athu

leno

lCa

ryop

hylle

ne o

xide

Hum

ulen

e epo

xide

II

0

20

40

60

80

100Cluster 1

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

()

(a)

Cluster 2

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(b)

Cluster 3

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(c)

Cluster 4

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(d)

Cluster 5

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(e)

Cluster 6

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(f)







Geranyl acetate

Perylene

120572-thujene

Myrcene

Myrtanyl acetate

120573-elemene


Germacrene B


naloo

l oxid

e

Linalool

18-Cineol

Myrtenal

(E)-nerolidol

1-Octen-3-ol

Caryophyllene oxide

Geraniol

120574-muurolene

Carvone

Limonene

SabineneElemol

Spathulenol

(E)-isocitral

o-Cymene


120572-guaiene

120574-terpinene

Trans-calamenene

minus10

minus08

minus06

minus04

minus02

00

02

04

06

08

10


Seco

nd p

rinci

pal c

ompo

nent

(1239

)

Geranial






4 Conclusions






Acknowledgments




References




















Journal of




Agronomy





Microbiology




Volume 2014

























120572-th

ujen

eSa

bine

ne1-

Oct

en-3

-ol

5-M

ethy

l-6-h

epte

n-2-

one

Myr

cene

o-Cy

men

eLi

mon

ene

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Tran

s-ca

lam

enen

eEl

emol

Ger

mac

rene

B(E

)-ne

rolid

olSp

athu

leno

lCa

ryop

hylle

ne o

xide

Hum

ulen

e epo

xide

II

0

20

40

60

80

100Cluster 1

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

()

(a)

Cluster 2

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(b)

Cluster 3

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(c)

Cluster 4

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(d)

Cluster 5

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(e)

Cluster 6

0

20

40

60

80

100

()

Sabi

nene

Myr

cene

Lim

onen

e

Lina

lool

Pery

lene

(E)-

isoci

tral

Myr

tena

lN

eral

Carv

one

Ger

anio

lG

eran

ial

Myr

tany

l ace

tate

Ger

anyl

acet

ate

Elem

olG

erm

acre

ne B

(E)-

nero

lidol

Spat

hule

nol

Cary

ophy

llene

oxi

deH

umul

ene e

poxi

de II

120574-te

rpin

ene

120573-e

lem

ene

120574-m

uuro

lene

120572-g

uaie

ne120573

-car

yoph

ylle

ne

120572-th

ujen

e

1-O

cten

-3-o

l5-

Met

hyl-6

-hep

ten-

2-on

e

o-Cy

men

e

18-

Cine

ol

cis-s

abin

ene h

ydra

tecis

-lina

lool

oxi

deTr

ans-

linal

ool o

xide

Tran

s-ca

lam

enen

e

(f)







Geranyl acetate

Perylene

120572-thujene

Myrcene

Myrtanyl acetate

120573-elemene


Germacrene B


naloo

l oxid

e

Linalool

18-Cineol

Myrtenal

(E)-nerolidol

1-Octen-3-ol

Caryophyllene oxide

Geraniol

120574-muurolene

Carvone

Limonene

SabineneElemol

Spathulenol

(E)-isocitral

o-Cymene


120572-guaiene

120574-terpinene

Trans-calamenene

minus10

minus08

minus06

minus04

minus02

00

02

04

06

08

10


Seco

nd p

rinci

pal c

ompo

nent

(1239

)

Geranial






4 Conclusions






Acknowledgments




References




















Journal of




Agronomy





Microbiology




Volume 2014

























Geranyl acetate

Perylene

120572-thujene

Myrcene

Myrtanyl acetate

120573-elemene


Germacrene B


naloo

l oxid

e

Linalool

18-Cineol

Myrtenal

(E)-nerolidol

1-Octen-3-ol

Caryophyllene oxide

Geraniol

120574-muurolene

Carvone

Limonene

SabineneElemol

Spathulenol

(E)-isocitral

o-Cymene


120572-guaiene

120574-terpinene

Trans-calamenene

minus10

minus08

minus06

minus04

minus02

00

02

04

06

08

10


Seco

nd p

rinci

pal c

ompo

nent

(1239

)

Geranial






4 Conclusions






Acknowledgments




References




















Journal of




Agronomy





Microbiology




Volume 2014


























References




















Journal of




Agronomy





Microbiology




Volume 2014


























Journal of




Agronomy





Microbiology




Volume 2014
























research article chemical diversity in lippia alba (mill.) n. e....

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