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Suresh Gyan Vihar University International Journal of Environment, Science and Technology Volume 4, Issue 1, January 2018, pp. 9-32 ISSN: 2394-9570

Phytochemicals From Prosopis Species

Lokesh Kumar Sonia, Sonal Dobhalb, Pradeep Parasherc and M.P. Dobhal*a

a Natural Products Laboratory, Centre of Advanced Studies, Department of Chemistry,

University of Rajasthan, Jaipur, India. Email: mpdobhal@gmail.com, lsoni492@gmail.com b Department of Zoology, University of Rajasthan, Jaipur, Rajasthan, India. c Department of Chemistry, Govt. P.G. College, Jhalawar, Rajasthan, India.

ABSTRACT

Prosopis cineraria is a species of angiospermous trees belonging to the Leguminosae family. It is found in arid areas in Western and South Asia. It is an established registered species in Indonesia. It is locally known as Jandi or Khejri (India), Jand (Pakistan), and Ghaf (Arabia). It is a vital medicative plant, each part being employed in medication. The bark of the tree cures leprosy, dysentery, bronchitis, asthma, leucoderma, piles and tremors of the muscles. Various phytoconstituents reported in different parts of Prosopis cineraria are patulitrin, sitosterol, spicigerine, patulibin, campesterol, sterol, stigmasterol, actacosanol, hentriacontane, prosogerin A,B,C,D and E, patuletin, luteolin, rutin, 3-benzyl-2-hydroxy-urs-12-en-28-oic acid, maslinic acid 3-glucoside, linolic acid, vitamin K, n-octacosyl acetate etc. The intent of this review is to grant an in-depth survey of the literature on its phytochemistry.

Keywords: Prosopis cineraria, Leguminosae, prosogerin A,B,C,D,E.

INTRODUCTION

Prosopis cineraria (L.) Druce belongs to the

cosmopolitan genus Prosopis, subfamily

Mimosaceae, tribe Leguminosae/ Fabaceae

(Rasanen & Lindstrom 2003). The genus

Prosopis includes 44 species of trees and

shrubs (Ramírez et al. 1999). Prosopis

cineraria is five to ten meters in hight and

grows in dry and arid regions of Arabia and in

some regions of Indian states, principally

Rajasthan, Haryana, Punjab, Gujarat, Western

Uttar Pradesh and in drier areas of Deccan. It

is known under numerous names, such as

Janti and Chonksa (Delhi), Jhind, Jhand and

Jand (Punjab and Haryana), Banni

(Karnataka), Sumri (Gujarat), Kandi (Sindh)

and Khejri (Sanskrit). Khejri is the only herb

tree that grows well despite all the

environmental condition odds of a desert.

Since all components of the tree are useful, it

is referred to as kalp taru. It is conjointly

referred to as the ‘wonder tree’ and therefore

as the ‘king of desert’( Bari et al. 2007;

Gupta & Prakash 1975; Kaul 1967;

Burdak 1982). It holds a crucial place in the

rural economy in the northwest region of the

10

Indian subcontinent (Puri &Kumar 1995).

Prosopis cineraria (L.) Druce is a deep-

rooted, nitrogen fixing, useful tree, endemic to

the hot deserts of India.

Khejri is a tiny moderate sized

evergreen thorny tree, with slender branches

armed with round-shaped thorns and with light

bluish-green foliage. The leaflets are dark

green with thin casting of light shade. New

leaves appear before or simultaneously with

the fall of the old leaves in summer. The small,

yellow flowers appear from March to May

after the new flush of leaves. Fruits are pod

and sweet in taste. Fleshy pods are sickle-

shaped and are 10 to 20 cms long and contain

a sweetish mucilaginous pulp. The pods are

formed soon thereafter and grow rapidly in

size. The pods ripen from June to August.

Growth of new foliage, flowering and fruiting

occurs during the driest months March- June

when other plants become leafless and

dormant (Firewood crops 1980; Tewari et

al. 1993).

The importance of the healthful

worth of this tree has been highlighted in

ancient Ayurvedic (medical) literature. Its

flower is pounded, mixed with sugar and used

throughout maternity as safeguard against

miscarriage. The bark of Prosopis cineraria is

dry, acrid, bitter with a pointy taste; cooling

anthelmintic, tonic, cures infectious disease,

dysentery, bronchitis, asthma, leucoderma,

piles, tremors of the muscles (Kirtikar &

Basu 1984). The bark is employed in

rheumatism, cough and colds, diarrhea, worm

infestations, and skin problems (Sharma

1993). The bark of the plant offers immediate

relief to an individual bitten by a snake or a

scorpion (Chopra et al. 1956). It has reported

that in the servere famine of rajputana in 1868-

69, several lives were saved by the

employment of bark as a supply to food. It was

ground into flour and transformed into cakes.

Smoke of the leaves seem to be good for eye

troubles. Leaf paste of P. cineraria is applied

on boils and blisters, together with mouth

ulcers in livestock and leaf infusion is

employed on open sores on the skin

(Nandkarni 2000). Leaves and fruits are used

to prepare medicines for curing nervous

disorders. The gum of the tree is nutritive and

good in taste and is employed by pregnant

woman at the time of delivery and is according

to be astringent, demulcent, and pectoral. A

paste of flowers beside twig conjointly act as

anti-diabetic agents, once administered orally.

PHYTOCHEMICAL

CONSTITUENTS

A considerable amount of work has been

carried out on the genus Prosopis, mainly on

chemical investigations and biological-

activity evaluation. A number of

phytochemicals (Sharma et al. 1964;

Bhardwaj et al. 1979; Malik & Kalidhar 2007;

Jewers et al. 1976; Aneela et al. 2014;

Bhardwaj et al. 1978; Bhardwaj DK et al.

1980; Bhardwaj et al. 1981; Uani et al. 2000;

Robertson & Narayanan 2014; Liu et al. 2012;

Gangal et al. 2009; Singh et al. 2013; Khan et

al. 2006; Soni et al. 2015), (Simpson &

Solbrig 1977; Ahmad et al. 1978; Ahmad et al.

11

1989; Nakano et al. 2001; Nakano et al. 2002;

D"atwyler et al. 1981; Peter et al. 2009;

Hiroshi et al. 2004; Singh 2012; Valli et al.

2014; Rastogi & Mehrotra 1993; Raghavendra

2000), (Harzallah-Skhiri & Jannet 2005),

(Elmezughi et al. 2013; Kolapo et al. 2009;

Abah et al. 2014), (Samoylenko et al. 2009),

(Malhotra & Misra 1983), (Ferguson et al.

2005; Ale et al. 2000) have been isolated and

characterized from Prosopis cineraria,

Prosopis juliflora, Prosopis farcta, Prosopis

africana, Prosopis glandulosa, Prosopis

chinensis, and Prosopis chilensis respectively.

Their structures are shown in figure 1, and

their names and the corresponding plant

sources are compiled in the Table 1.

Table 1. Chemical Constituents of Plants from the Genus Prosopis

No. Compound name Source Ref.

Flavonoids

1 Patulitrin P. cineraria (Sharma et al. 1964)

2 Prosogerin A (6 Methoxy- 7-hydroxyl–3’4’-

methylencedioxylflavone)

P. cineraria (Bhardwaj et al.

1979)

3 Prosogerin B (2’ 4’ Dihydroxy -5’methoxy-3,4-

methylenedioxy chalcone (II))

P. cineraria (Bhardwaj et al.

1979)

4 Prosogerin C (6,7,3’,4’,5’- pentametoxyflavone) P. cineraria (Bhardwaj et al.

1978)

5 Prosogerin D (6’,3’,4’5’,- tetramethoxy-7-hydroxyl

flavone)

P. cineraria (Bhardwaj et al.

1980)

6 Prosogerin E (6,7-dihydroxy-3’,4’,5’,-trimethoxy

flavone)

P. cineraria (Bhardwaj et al.

1981)

7 Patuletin P. cineraria (Bhardwaj et al.

1981; Ukani et al.

12

2000)

8 Luteolin P. cineraria (Bhardwaj et al.

1981; Ukani et al.

2000)

9 Apigenin P. juliflora (Simpson & Solbrig

1977)

10 Apigenin 6,8-di-C-glycoside P. juliflora (Simpson & Solbrig

1977)

11 Chrysoeriol 7-O-β-D-glucoside P. juliflora (Simpson & Solbrig

1977)

12 Luteolin 7-O- glucoside P. juliflora (Simpson & Solbrig

1977)

13 Kaempferol 3-O-methyl ether P. juliflora (Simpson & Solbrig

1977)

14 Isorhamnetin 3-O-glucoside P. juliflora (Simpson & Solbrig

1977)

15 Isorhamnetin 3-O-rutinoside P. juliflora (Simpson & Solbrig

1977)

16 Quercetin 3-O-rutinoside P. juliflora (Simpson & Solbrig

1977)

17 (-)-Mesquitol P. juliflora (Peter et al. 2009)

18 Myricetin 3 - O-glucoside P. farcta (Harzallah-Skhiri &

Jannet 2005)

19 Isovitexin P. farcta (Harzallah-Skhiri &

Jannet 2005)

13

20 Quercetin 3- O-galactoside P. farcta (Harzallah-Skhiri &

Jannet 2005)

21 7,3’,4’-Trihydroxy-3-methoxy flavanone P. Africana (Elmezughi et al.

2013)

22 Ellagic acid P. juliflora (Raghavendra 2000)

23 Ellagic acid 4-0-rutinoside P. chinensis (Malhotra & Misra

1983)

24 Apigenin-8-glucoside P. chilensis (Ferguson et al.

2005)

25 Apigenin-6-glucoside P. chilensis (Ferguson et al.

2005)

26 Quercetin-3-glucoside P. chilensis (Ferguson et al.

2005)

27 Quercetin- 3-rhamnoside P. chilensis (Ferguson et al.

2005)

Alkaloids

28 Spicigerine P. cineraria (Bhardwaj et al.

1979)

29 Dasycarpidan-1-methanol,acetate (ester) P. cineraria (Aneela et al. 2014)

30 3-Butylindolizidine P. cineraria (Aneela et al. 2014)

31 Prosophylline P. cineraria (Aneela et al. 2014)

32 N- Methyljulifloridine P. juliflora (Simpson & Solbrig

1977)

33 Julifloridine P. juliflora (Ahmad et al. 1978)

34 Prosoflorine P. juliflora (Ahmad et al. 1989)

14

35 Juliprosinene P. juliflora (Ahmad et al. 1989)

36 Juliprosine P. juliflora (D"atwyler et al.

1981)

37 Secojuliprosopinal P. juliflora (Hiroshi et al. 2004)

38 2,4-Diphenyl-6,7,8,9 – tetrahydro-5H-cyclohepta (D)

pyrimidine

P. juliflora (Valli et al. 2014)

39 Cassine P. juliflora (Valli et al. 2014)

40 Tertiary juliprosopine P. glandulosa (Samoylenko et al.

2009)

41 Prosopilosidine P. glandulosa (Samoylenko et al.

2009)

42 Prosopilosine P. glandulosa (Samoylenko et al.

2009)

43 Isoprosopilosine P. glandulosa (Samoylenko et al.

2009)

44 Isoprosopilosidine P. glandulosa (Samoylenko et al.

2009)

45 2, 3-Dihydro - 1H-indolizinium chloride P. glandulosa (Samoylenko et al.

2009)

46 Tryptamine P. chilensis (Ferguson et al.

2005)

47 β – Phenethylamine P. chilensis (Ale et al. 2000)

Steroids

48 Cholesterol P. cineraria (Malik & Kalidhar

15

2007; Jewers et al.

1976)

49 7,24-Tirucalladien-3-one P. cineraria (Malik & Kalidhar

2007; Jewers et al.

1976)

50 Campsterol P. cineraria (Bhardwaj et al.

1981)

51 Stigmasterol P. cineraria (Bhardwaj et al.

1981)

52 β-Sitosterol P. cineraria (Bhardwaj et al.

1981)

53 Stigmasta-4,6-dien-3-one P. cineraria (Bhardwaj et al.

1981)

Fatty acids and Derivatives

54 (Z)-13-Docosenamide P. cineraria (Aneela et al. 2014)

55 9-Hexadecenoic acid P. cineraria (Aneela et al. 2014)

56 Palmitic acid P. cineraria (Ukani et al. 2000)

57 Stearic acid P. cineraria (Ukani et al. 2000)

58 Oleic acid P. cineraria (Ukani et al. 2000)

59 Linoleic acid P. cineraria (Ukani et al. 2000)

60 Heneicosanoic acid P. cineraria (Khan et al. 2006)

61 Methyl heptacosanoate P. cineraria (Khan et al. 2006)

16

Phenolic compounds

62 4,4'-(1-Methylethylidene) bis – phenol P. cineraria (Aneela et al. 2014)

63 Gallic acid P. cineraria (Bhardwaj et al.

1981; Ukani et al.

2000)

64 Rutin P. cineraria (Bhardwaj et al.

1981; Ukani et al.

2000)

65 Paeonol P. cineraria (Singh et al. 2013)

66 4- Hydroxy benzoic acid P. cineraria (Khan et al. 2006)

67 2,4-Bis (1-phenylethyl) phenol P. juliflora (Valli et al. 2014).

68 2,4,6-Tris-(1-phenylethyl) phenol P. juliflora (Valli et al. 2014).

Terpenoids

69 Phytol P. cineraria (Aneela et al. 2014)

70 Squalene P. cineraria (Aneela et al. 2014)

71 3 -Benzyl-2-hydroxy-urs-12-en-28-oic acid P. cineraria (Gangal et al. 2009)

72 β – Carotene P. juliflora (Elmezughi et al.

2013)

73 Friedelin P. Africana (Elmezughi et al.

2013; Kolapo et al.

2009; Abah et al.

2014)

74 Rhodopin P. cineraria (Aneela et al. 2014)

75 Rhodoxanthin P. cineraria (Aneela et al. 2014)

17

Phenyl propanoids

76 (–)-Lariciresinol P. juliflora (Nakano et al. 2001;

Nakano et al. 2002)

77 Ferulic acid P. cineraria (Singh et al. 2013)

78 Methyl 4-hydroxycinnamate P. cineraria (Khan et al. 2006)

79 Methyl 2-methoxy-5-hydroxycinnamate P. cineraria (Khan et al. 2006)

80 O-Coumaroylglycerol P. cineraria (Khan et al. 2006)

81 Syringin P. juliflora (Nakano et al. 2001;

Nakano et al. 2002)

Tetra pyrroles

82 Pheophytin A P. juliflora (Singh 2012)

83 Pheophytin B P. juliflora (Singh 2012)

Others (alcohols, esters, diketones, alkanes,

heterocyclic compounds, etc.)

84 Hentriacontane P. cineraria (Malik et al. 2007;

Jewers et al. 1976)

85 Actacosanol P. cineraria (Malik et al. 2007;

Jewers et al. 1976)

86 Methyl docosanoate P. cineraria (Malik et al. 2007;

Jewers et al. 1976)

87 Diisopropyl-10,11-dihydroxyicosane-1,20-dioate P. cineraria (Malik et al. 2007;

Jewers et al. 1976)

88 Tricosan-1-ol P. cineraria (Malik et al. 2007;

Jewers et al. 1976)

18

89 Dichloronitromethane P. cineraria (Aneela et al. 2014)

90 Octamethylcyclotetrasiloxane α) P. cineraria (Aneela et al. 2014)

91 2-Methyl benzaldehyde P. cineraria (Aneela et al. 2014)

92 2,7-Anhydro-1- heptulofuranose P. cineraria (Aneela et al. 2014)

93 2-[(9Z)-9-Octadecene-1-yloxy]ethanol P. cineraria (Aneela et al. 2014)

94 2-C-Methyl myoinositol P. cineraria (Aneela et al. 2014)

95 2-Methyl-2-(3-oxobutyl)-1,3-cyclohexanedione P. cineraria (Aneela et al. 2014)

96 Diphenyldimethylsilane α) P. cineraria (Aneela et al. 2014)

97 Dibutyl phthalate α) P. cineraria (Aneela et al. 2014)

98 2,2,4-Trimethyl-4-(4' trimethylsilyloxyphenyl)

chromane α)

P. cineraria (Aneela et al. 2014)

99 5-Nitro-2-furaldehyde P. cineraria (Aneela et al. 2014)

100 N-[4-(Tributylstannyl)butyl]-3

tributylstannylpropionamide α)

P. cineraria (Aneela et al. 2014)

101 17-Pentatriacontene P. cineraria (Aneela et al. 2014)

102 Octacosyl pentafluoropropionate P. cineraria (Aneela et al. 2014)

103 5,5’-Oxybis-1,3-benzendiol P. cineraria (Liu et al. 2012)

104 Vitamin K P. cineraria (Gangal et al. 2009)

105 n-Octacosyl acetate P. cineraria (Gangal et al. 2009)

106 L-Tryptophan P. juliflora (Nakano et al. 2001;

Nakano et al. 2002)

107 Prosopidione P. juliflora (Nakano et al. 2001;

Nakano et al. 2002)

108 Benzothiazole P. juliflora (Valli et al. 2014)

109 Diethyl phthalate α) P. juliflora (Valli et al. 2014)

19

110 4-Isopropyl-1,6-dimethyl naphthalene P. juliflora (Valli et al. 2014)

111 Diisobutylphthalate α) P. juliflora (Valli et al. 2014)

112 7,9,-Di-tert-butyl-1-oxaspiro (4,5) deca-6,8-diene-

2,8-dione

P. juliflora (Valli et al. 2014)

113 Dibutyl phthalate α) P. juliflora (Valli et al. 2014)

114 Mono(2- ethylhexyl) phthalate α) P. juliflora (Valli et al. 2014)

115 Procyanidin B2 P. juliflora (Rastogi & Mehrotra

1993)

116 Methyl 5-tridecyloctadec-4-enoate P. cineraria (Soni et al. 2015)

117 Nonacosan-8- one P. cineraria (Soni et al. 2015)

118 Lupeol P. cineraria (Soni et al. 2015)

α) = Artefect of isolation (no natural product)

20

 

21

22

 

 

23

24

 

25

 

26

 

27

28

 

Figure 1. Structures of isolated compounds from Prosopis species

29

CONCLUSION

Genus Prosopis is a vital healthful genus.

Prosopis species have varied

phytoconstituents and possess different

kinds of biological activities and is used

medicinally since ancient times.

Considering the pharmaceutical prospects

there's ample scope for future

investigations on the genus Prosopis.

ACKNOWLEDGEMENT

The author is grateful to UGC, New Delhi

for granting the senior research fellowship.

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