jatropha_curcas_-_the_biofuel_plant_4324561945

SECONDARY METABOLITE COMPOUNDS FROM JATROPHA SPECIES

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Several secondary metabolite compounds from some Jatropha species were successfully isolated and identified. Biological activities of some compounds were examined and validated that made Jatropha species become interest for researchers and society, recently.

Jatropha curcas Linn.

J. curcas is a small tree or large shrub, which can reach a height of three to five meters, but under favorable conditions it can attain a height of 8 or 10m. The plant shows articulated growth, with amorphological discontinuity at each increment. The branches contain latex. Normally, five roots are formed from seedlings, one central and four peripheral. A tap root is not usually formed by vegetatively propagated plants. Leaves five to seven lobed, hypostomic and stomata are of paracytic (Rubiaceous) type [1]. The trees are deciduous, shedding the leaves in dry season. Flowering occurs during the wet season an two flowering peaks are often seen, i.e. during summer and autumn. In permanently humid regions, flowering occurs throughout the year. The inflorescence in axillary paniculate polychasial cymes. The plant is monoecious and flowers are unisexual; occasionally hermaphrodite flowers occur [2]. A flower is formed terminally, individually, with female flowers (tricarpellary, syncarpous with trilocular ovary) usually slightly larger and occurs in the hot seasons. In conditions where continous growth occurs, an unbalance of pistillate or staminate flower production results in a higher number of female flowers. Ten staments are arranged in two distinct whorls of five each in asingle column in the androecium, and in close proximity to each other. In the gynoecium, the three slender styles are connate to about two-thirds of their length, dilating to massive bifurcate stigma [2]. The rare hermaphrodite flowers can be selfpollinating. The flowers are pollinated by insects especially honey bees. Each inflorescence yields a bunch of approximately 10 or more ovoid fruits. With good rainfall conditions nursery plants may bear fruits after the first rainy season, and directly sown plants after the second rainy season. Three, bivalve cocci is formed after the seeds mature and fleshly exoacarp dries. The seeds mature about 3-4 months afer flowering. The seeds are black and the seed weight per 1000 is about 727g, there are 1375 seeds/kg/in the average [1]. J. curcas is cultivated as a medicinal plant in many tropical and subtropical countries. It is suitable for preventing soil erosion and shifting of sand dunes. Various parts of the plant hold potential for use as a source of oil, animal feed or medicinal preparations. Recently, their seeds were investigated mainly as a potential source of oil that was recognized as an adequate substitute motor fuel [3].

Ethyl acetate extracts of leave of J. curcas contain a complex of 5-hydroxypyrrolidin-2-one and pyrimidine-2,4-dione (uracil) [4].

The seed kernels of J. curcas were rich in crude protein, CP (31-34.5%) and lipid (55-58%). The major fatty acids found in the oil were oleic (41.5-48.8%), linoleic (34.6-44.4%), palmitic (10.5-13.0%), stearic (2.3-2.8%), cis-11-eicosenoic and cis-11,14-eicosadienoic acids [5]. Seed oil contain 12-deoxy-16-hydroxyphorbol (1) belonging to phorbol ester which has tumor-promoting activity [6]. The common diterpene 12-deoxy-16-hydroxyphorbol in six different diterpene esters from the J. curcas oil have determined using HPLC methode which named as Jatropha factors C1 to C6 (2-7) [7].

From the latex of J. curcas, a novel cyclic octapeptide was isolated and named curcacycline A (8) which displays a moderate inhibition of classical pathway activity of human complement and proliferation of human T-cells [8], curcacycline B (9) [9], jatrophidin I (10) [10] has antifungal activity, and pohlianin A (78) [11] has antifungal and antimalarial activity [10].

Diterpene compounds such as tigliane (11), jatrophone (12) and dinorditerpene (13), 3-O-acetylaleuritolate acid (14), a triterpenoid have been identified from this plant [12]. The roots of J. curcas is a rich source of diterpenes of the daphnane and lathyrane skeletons [13]. From hexane extract of this plant well known jatropholones A (15), B (16) [14], curculathyrane A (17) and B (18), and curcusone A-D (19-22) [13].

Polar fraction of crude extract of the roots of J. curcas contains propacin (23), (+)-jatrophol (24), (+)-marmesin (25) and jatrophine (26). Two type of lathyrane, 15-O-asetil-15-epi-(4E)-jatrogrossidentadione (27) and isojatrogrossidentadione (28) and two podacarpane, 3β-acetoxy-12-methoxy-13-methyl-podocarpa-8,11,13-triene-7-one (20) and 3β,12-hydroxy-13-methyl-podocarpa-8,10,13-triene (30) have been isolated and identified from aerial part of J. curcas [15].

Compound 5α-stigmastane-3,6-dione (31), β-sitosterol (32), estigmasterol (33), taraxasterol (34), daucasterol (35), nobiletin (36), 5-hydroxy-6,7-dimethoxycoumarin (37), 6-methoxy-7-hydroxycoumarin (38), 3-hydroxy-4-methoxybenzaldehide (39), 3-methoxy-4-hydroxybenzoate acid (40), glyceride-1, 2S-tetracosanoate acid (41) and caniojane (42) have been isolated from the roots of J. curcas [14].

Aqueous extracts of leaves of J. curcas were evaluated for antihelmintic activity on adult Indian earthworms Pheretima poshtuma that indicated significant activity [16]. Methanolic extract of this plant has shown antiulcer activity on aspirin-induced gastric lesions in Wistar rats [17]. The in vitro antimicrobial activity of crude ethanolic, methanolic and water extracts of the stem bark of J. curcas against Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Streptococcus faecalis, Staphylococcus epidermidis, Shigella dysentriae, Micrococcus kristinae, Klebsiella pneumonia, Bacillus cereus, Bacillus subtilis, Proteus vulgaris dan Serratia marcescens were investigated [18]. Toxicity of seed oil of J. curcas was evaluated against Callosobruchus maculates insects dan its parasite, Dinarmus basalis [19].

The research of nickel toxicity induced in J. curcas has shown a correlation between responses of antioxidant enzymes as well as PAL activities and nickel concentrations in J. curcas cotyledons. The lower nickel concentrations and higher superoxide dismutase (SOD), peroxidase (POD), catalase (CAT) dan phenylalanine ammonia lyase (PAL) activities suggest the tolerance capacity to protect the plant from oxidative damage [20].

Jatropha chevalieri

Isolation compound of latex of J. chevalieri has resulted cyclic peptide, chevalierin A (43), B (44) and C (45) . Compound 43 was evaluated that has antimalarial activity with IC50 8.9 µM [21].

Jatropha elliptica

J. elliptica Muell. Arg., a shrub annual herb distributed throughout the North and the West of Brazil and has been reported to possess several medicinal properties [22,23,24]. J. elliptica is used in the folk medicine for treatment of neoplasia, inflammation, ulcers and diuretic diseases among others [24]. The ethanolic extract of root has shown molluscicidal activity [12].

A penta-substituted pyridine namely diethyl 4-phenyl-2,6-dimethyl-3,5-pyridinecarboxylate (46) was assayed for in vitro antibacterial and resistance-modifying activity against strains of S. aureus possessing the MsrA and NorA resistance efflux mechanisms. Antibiotic efflux studies indicated that the title compound acts as an inhibitor of the NorA efflux pump and restores the level of intracellular drug concentration [12].  This compound was isolated from rhizomes of J. elliptica which has crystal structure was monoclinic ( P121/n1 (no.14), a = 11.204 (5) Å, b = 8.368 (5) Å, c = 18.817 (5) Å, β = 99.366 (5)°, V = 1740.7 Å3, Z = 4, Rgt (F) = 0.054, wRref (F2) = 0.154, T = 293 K) [25]. Isolation compound of the roots of J. elliptica has resulted diterpenoid compound 12, 14, 15, 16, 23, pentatriacontanyl ferulate (47), fraxetin (48) and mixtures of compound 32 and 33 [26].

Compound 12, extracted from J. elliptica inhibited [3H]glutamate binding. These results may indicate a neurochemical parameter possibly related to the antinoceptive activity of these natural compounds [27]. Several biological activities have been reported for 12, including the molluscicidal effect [24], reaction of biological thiols (inhibition tumor activity) [28], interaction with sRNA from Escherichia coli [29], inhibition of insulin release [30], relaxation effect of induced uterine contraction [31], relaxant action in rat portal vein [32], inhibition of lymphocytes activation, probably through inhibition of the protein kinase C pathway [33], antiprotozoal activity [34], antileishmanial activity [35], antileukemic activity against P-388 lymphocytic leukemia at 27 and 12 mg/kg cytotoxicity (ED50) against KB cell culture at 0.17 µg/ml [36].

Jatropha gaumeri

Isolation of secondary metabolite compound from roots extract of J. gaumeri was obtained as 2-epi-jatrogrossidione (49), a rhamnofolane diterpene and 15-epi-4E-jatrogrossidentadione (50), a lathyrane diterpene. Compound 49 has antimicrobial activity and 50 without biological activity. Crude leaf extract of J. gaumeri contains compound 32, 34, triterpenes α-amyrin (51) and β-amyrin (52), which responsible for the antioxidant activity.

Jatropha gossypifolia

J. gossypifolia (synonym: Adenoropium gossypifolia Pohl, J. elegans) belonging to the family Euphorbiaceae [38] is a shrub herb, height 1.8 meter, gregarious with palmately 3-5 lobed leaves and dark red, crimson or purplish flowers. Leaf margins, petioles and stipules are covered with glandular hairs [39].

J. gossypifolia is grows naturally almost entire tropical area in the world [40]. This plant is a native of Brazil, naturalized in many parts of India. It grows on nearly all type of soils within its range. It is common in waste lands, roadsides, poorly tended agricultural fields and river overflow area [41]. Another opinion said that J. gossypifolia is native to the Carribean and tropical America but is now widespread throughout the tropical world. It has been listed as a weed in India, Brazil, Jamaica and Trinidad [42]. Flowering in India occurs from February through July. Sometimes both flowers and fruits will be present at the same time on plant. Upon drying, the capsule valves spring open propelling the seeds a few centimeters [41].

J. gossypifolia is reported to be beneficial to dyscrasia, anemia, vertigo and dysphonia [38]. It is an antibiotic, insecticidal and used in toothache and act as blood purifier [43]. The leaves are employed to carbuncles, eczema and itches, act as purgative and swollen. A decoction of the leaves is useful for stomachache, venereal disease and as blood purifier [44]. The leaves, either in decoction or boiled like spinach, as a purgative remedy for ‘dry belly-ache’. It is used to prepare tea for constipation, the part used not being specified but it is probably the leaves [45]. Extracts of the plant are used as a purgative and emetic, and to treat headache, diarrhea, venereal disease, skin sores, mouth sores and cancer [40]. The seed are used to purgative, its oil similar to Castrol oil (Jatropha) [45]. The use of the seeds in herbal medicine is advised against because of their high toxicity [46]. The seed oil is used as an emetic, purgative and stimulant. It is also applied for ulcers and leprosy and is beneficial in adenites and worm infestation [44]. The roots are recommended for leprosy and as an antidote for snake bite [38].

J. gossypifolia in many country is used as medicinal plant, variously. In India, it is used to treat diarrhea [47] and the roots are employed to dysentery [48]. Decoction of J. gossypifolia in Trinidad are beneficial to treat wound and reduce pain. This beneficial similar to etnoveterinary remedies by certain hunter to treat snakebites, scorpion stings, for injuries and mange of their dogs [49]. Ethnomedicine use in Tobago and Trinidad are to treat snatch wound, sores and swollen [50]. In Ghana, decoction of leaves of J. gossypifolia, Combretum ghaselensis and the whole part of Ocimun canum are used to malarial [51]. In Ekiti, Nigeria, J. gossypifolia were cultivated to serve as boundary plants, erosion control and healing of mouth cancer [52]. In Southern Nigeria, the extract from fresh leaf applied with crushed leaf is routinely used by herbalists and local people to stop bleeding from the skin and nose [53,54] and in Suriname, the fruits are used as a purgative [55].

Ogundare et al. [39] has been reported the antimicrobial activity of leaves extracts of J. gossypifolia against 10 microorganisms (Table 1).

Tabel 1. Antimicrobial activity of leaves extracts of J. gossypifolia.

Inhibition Zone (mm)
Tested Microorganism Chloroform extract of J. gossypifolia Leaves Methanolic extract ofJ. gossypifolia Leaves
Escherichia coli NI NI
Bacillus subtilis NI NI
Salmonella typhi 12.0 12.5
Staphylococcus aureus 6.0 18.0
Proteus mirabilis NI NI
Carynebacterium diptheriae NI NI
Pseudomonas aeroginosa 10.0 12.0
Shigella dysentriae NI NI
Streptococcus pneumonia NI NI
Candida albicans 30.0 35.0
NI: No Inhibition

Secondary metabolites have been isolated and identified from J. gossypifolia:

The Whole Plant

Compounds belonging to diterpenoid have been isolated from the whole plant were citlalitrione (53) [56] and jatrophenone (54) [57]. Compound 54 was found to posses antibacterial activity against Staphylococcus aureus. Its activity was comparable to that of the standard compound, penicillin G [57]. A coumarino-lignoid, propacin (23) also was obtained [58].

Seed

The seed oil of J. gossypifolia contains a phorbol ester, 1 was found to posses activity as a tumor-promoter [6].

Aerial parts and Stems

Two lignans have been isolated from J. gossypifolia was gossypidien (55) [60] that isolated from its stems  and gossypifan (56) [61] that isolated from aerial parts of this plant. A coumarino-lignoid, cleomiscosin (57) was obtained by soxhletation with hexane and ethyl acetate [62]. Furthermore, two lignins namely isogadain [(+)-savinin or hibalactone] (58) [63] and diester jatrodien (59) [64]. Catechin [60] also isolated from its stems bark. The latex contains cyclogossine B (61) [65], a cyclic octapeptide. Cyclogossine A and B was posses to  antimalarial activity [50].

Leaves

Chemicals composition of lipid extracts of leaves of J. gossypifolia (Table 2) have been identified by GC-MS [59].

Table 2. Chemicals composition of lipid extracts of leaves of J. gossypifolia

Compound Composition Relative Abundance (%)
Propanoic acid C3H6O2 0.9
Glycerol C3H8O3 12.0
2-pentenoic acid C3H8O 13.7
Arabitol C5H12O5 12.3
3,7,11,15-tetramethyl-2-hexadecene-1-ol C20H40 2.0
D-Xylofuranose C5H10O5 n.d
D-mannitol C6H14O 0.7
Hexadecanoic acid C16H32O2 7.8
Inositol C6H12O6 n.d
Oleic acid C18H34O2 6.3
Octadecenoic acid C18H36O2 2.7
Octacosan C28H58 n.d
Octacosanol C28H58O 2.3
Stigmasterol C29H48O 2.5
α-Sitosterol C29H50O 8.8
α-Amyrin C30H50O n.d
Lup-20(29)-en-3-on C30H48O n.d
Betulin C30H50O2 n.d

Roots

The roots of J. gossypifolia contains 12 [66], 15 and 16 [26]. Biotransformation of 12 by Aspergillus niger ATCC (American Type Culture Collection) 16404 afforded the new diterpene 9β-hydroxyisabellione (62) [67]. The cytotoxicity of the compounds as IC50 values on AGS and lung fibroblasts was 2.4 and 2.8 µM for 12 and 53.1 and 260 µM for 62, respectively [62].

Jatropha grossidentata

J. grossidentata Pax et Hoffm. is a shrub known as ‘Caniroja’ by the Ayoreo Indians living in the central-northern par of the Paraguayan Chaco. The powdered roots are smoked in shamanic practices [68].

The petroleum ether and ethyl acetate extract of J. grossidentata roots showed in vitro activity against Trypanosoma cruzi and Leishmania strains at 10 µg/mL. Several diterpenes have been isolated from the roots, the main compound being the rhamnofolane jatrogrossidione (49) [69,70]. Compound 49 showed a strong in vitro leishmanicidal and trypanocidal activity with IC100 of 0.75 and 1.5-5.0 µg/mL, respectively.

Jatropha integerrima

J. integerrima Jacq. (syn. J. pandurifolia Andr.) is a shrubby tree of which the medicinal properties have not been reported. Its latex is however known to be toxic. The leaves, if accidentally chewed can cause squeamish, stomachalgia and can be very purgative [71].

CH2Cl2 extracts of latex of J. integerrima contains two new cyclic heptapeptides, integerrimides A (63) and B (64). Both peptides 63 and 64 at 50 µM inhibited to a certain degree cell proliferation of human ICP-298 melanoma cells, as well as cell, migration of human Capan II pancreatic carcinoma cells, buth both compounds were inactive in HSV-1, antifungal and antimalarial assays [71].

The roots of J. integerrima contains rhamnofolane endoperoxide  2-epicaniojane together with caniojane and 1,11-bisepicaniojane (65) and integerrimene (66), a 8,9-seco-rhamnofolane skeletons and a possible biogenetic precursor [72].

Jatropha multifida

Latex of J. multifida contain a novel non-cyanogenic cyanoglucoside, 1-cyano-3-β-D-glucocyranosyloxy-(Z)-1-methyl-1-propene was named multifidin A (67) [73]. Previously, isolation of multifidol (68) and its glucoside (69) [74), two cyclic peptides, labaditin (70) [75], a cyclic decapeptide and biobollein (71) [76], a cyclic nonapeptide have been reported.

Jatropha podagrica

Tetramethylpirazine (TMPZ) [77] is an alkaloid found in J. podagrica that causes vasolidation [78] and reduces thrombosit [79].

The roots of J. podagrica contains a new aliphatic acid named japodic acid (72) with a gem-dimethyl cyclopropane ring [80]. Compound 72 showed mild insect growth inhibition activity against Helicoverpa zea and were inactive in the antibacterial assays. Methanolic and khloroform extract of the roots of J. podagrica contains fraxidin (73) and erythrinasinate (74). Both compounds exhibited antibacterial activity against Bacillus subtilis [80]. Futhermore, two peptides, podacycline A (75), a cyclic nonapeptide and podacycline B (76), a cyclic heptapeptide were isolated from the latex of J. podagrica [81].

Podacycline B was found to possess high cytotoxicity against Dalton’s lymphoma ascites (DLA) and Ehrlich’s ascites carcinoma (EAC) cell lines with IC50 values of 13.2 and 15.5 µM, in addition to moderate anthelmintic activity against earthworms Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus sp. at a dose of 2 mg/mL [82].

Jatropha pohliana

J. pohliana Müll. Arg. (Syn: Adenophorum molissimum Pohl, Adenophorum luxurians Pohl, Jatropha molissimma (Pohl) Baill., Jatropha pohliana var. mollissima (Pohl) Müll. Arg., Jatropha luxurians (Pohl) Baill.) known as Pinhão-bravo and  pinhão-de-purga [83].

Three cyclic peptides, pohlianin A (77), B (78) and C (79) was isolated from the latex of J. pohliana, which found to posses antimalarial activity with IC50 values of 57 μM, 25 μM and 16 μM, respectively. Compound 79 being the more potent [11].

Jatropha tanjorensis

J. tanjorensis has medium thick stout stem with sparse branching, sparse pigmentation. Leaves alternate, palmately five lobed, light green to dark green with no pigmentation except on very young leaves, margins distantly serrate, long petiole with dense pigmentation. Cymose inflorescence with coinflorescence, monoecious unisexual and bisexual, medium sized green with pale pink tinged flowers, 8 yellow stamens arranged in a single layer, highly sterile pollen. Fruit not seen [84]

J. tanjorensis is popular as a natural remedy against malaria infection and hypertension in some parts of Nigeria, however there is dearth in scientific validation of these claims [85]. Edo people in Nigeria consumed the leaves as a vegetable and known as catholic vegetable [86]. Phytochemical screening of J. tanjorensis leaf revealed that it contains bioactive principles such as alkaloids, flavonoids, tannins, cardiac glycosides, anthraquinones and saponins [87].

Jatropha unicostata

Relative composition of the leaves of J. unicostata were unidentified sterol (0.9%), campesterol (4.9%), stigmasterol (36.5%), sitosterol (56.4%), stigmastanol (1.3%); 76 mg 3-oxo-steroids: campest-4-en-3-one (6.6%), stigmast-4,22-diene-3-one (19.8%), stigmast-4-en-3-one (78.3%); 26 mg dioxosteroids: campest-4-en-3,6-dione (5.6%), stigmast-4,22-diene-3,6-dione (42.2%), stigmast-4-en-3,6-dione (52.2%). The observed ketosteroids might be constituents of the latex from J. unicostata. Fraxetin (7,8-dihydroxy-6-methoxy-coumarin) and luteolin (3’,4’, 5,7-tetrahydroxyflavone) were isolated as main constituents from the ethyl acetate fraction [88].

Jatropha weddelliana

J. weddelliana is a shrub found in calcimorphic and dry soils of the highlands bearing the ‘pantanal’ of Mato Grosso do Sul, Brazil [89].

Hexane extracts of the roots of J. weddelliana contains 14 and 32. A diterpene with type of lathyrane skeletons named jatrowedione (80) was isolated from the stems extracts of this plant [90].

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2 thoughts on “SECONDARY METABOLITE COMPOUNDS FROM JATROPHA SPECIES

  1. Very useful account of the medicinalproperties of Jatropha species.There is need to exploit most of species s th genus Jatropha is represented by about 175 species mostly in Central America,Mexico,Africa,Arabia and India.Prof Bir Bahadur,India

  2. Thanks very useful information on Jatrophas.Please keep sending.For your kind info our book on Jatropha,Challenges for New Energy Crop by Me(Bir Bahadur,Suijatha M and N.Carels by Springer publisher,NY.,Vol.1& is due in few months from now

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