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Phorbol Esters and Other Toxic Constituents of Jatropha curcas L.

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Jatropha, Challenges for a New Energy Crop

Abstract

Jatropha curcas is a tropical perennial shrub having multiple benefits. Besides being a source of biofuel, it can be cultivated to control soil erosion, waste land reclamation. Various parts of the plant are rich in secondary metabolites with medicinal value. The Jatropha seed cake, a by-product, is an excellent source of proteins as an animal feed. However, the presence of toxins and anti nutritional compounds prevented its use as a source of protein. On the other hand, researchers are looking into use of Jatropha toxins as a source of tumour inhibitor and as a bio-pesticide. In this review, we discuss major toxic components present in J. curcas and some of the Jatropha species.

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References

  • Abreu IC, Alex Marinho SS, Paes AMA, Freire SMF, Olea RSG, Borges MOR et al (2003) Hypotensive and vasorelaxant effects of ethanolic extract from Jatropha gossypiifolia L. in rats. Fitoterapia 74:650–657

    Article  PubMed  Google Scholar 

  • Achten WMJ, Verchot L, Franken YJ, Mathijs E, Singh VP, Aerts R et al (2008) Jatropha biodiesel production and use. Biomass Bioenergy 32:1063–1084

    Article  CAS  Google Scholar 

  • Agamuthu P, Abioye OP, Abdulaziz A (2010) Phytoremediation of soil contaminated with used lubricating oil using Jatropha curcas. J Hazard Mater 179:891–894

    Article  PubMed  CAS  Google Scholar 

  • Ahmed O, Adam SE (1979) Toxicity of J. curcas in sheep and goats. Res Vet Sci 27:89–96

    PubMed  CAS  Google Scholar 

  • Ahmed WA, Salimon J (2009) Phorbol ester as toxic constituents of tropical Jatropha curcas seed oil. Eur J Sci Ind Res 31:429–436

    Google Scholar 

  • Aiyelaagbe OO (2001) Antibacterial activity of Jatropha multifida roots. Fitoterapia 72:544–546

    Article  PubMed  CAS  Google Scholar 

  • Aiyelaagbe OO, Gloer JB (2008) Japodic acid, a novel aliphatic acid from Jatropha podagrica Hook. Rec Nat Prod 2:100–106

    CAS  Google Scholar 

  • Aiyelaagbe OO, Adesogan K, Ekundayo O, Gloer JB (2007) Antibacterial diterpenoids from Jatropha podagrica Hook. Phytochemistry 68:2420–2425

    Article  PubMed  CAS  Google Scholar 

  • Altei WF, Picchi DG, Barbosa SC, Cilli EM, Giannini MJ, Cardoso-Lopes EM et al (2008) NMR studies, solid phase synthesis and MD/SA simulation as a tool for structural elucidation of new bioactive peptides from the latex of Jatropha curcas L. Planta Med 74:65

    Article  Google Scholar 

  • Aregheore EM, Makkar HPS, Becker K (1997) Lectin activity in toxic and nontoxic varieties of J. curcas using a latex agglutination test. In: Proceeding of the international conference biofuels and industrial products from Jatropha curcas, Nicaragua

    Google Scholar 

  • Auvin C, Baraguey C, Blond A, Lezenven F, Pousset JL, Bodo B, Curcacycline B (1997) a cyclic nona-peptide from Jatropha curcas enhancing rotamase activity of cyclophilin. Tetrahedron Lett 38:2845–2848

    Article  CAS  Google Scholar 

  • Bahadur B, Reddy SM, Goverdhan S, Giridhar P (1997) Antimicrobial activity in eight species of Jatropha L. (Euphorbiaceae). J Indian Bot Soc 77:190–191

    Google Scholar 

  • Banerji J, Das B, Chatterjee A, Shoolery JN (1984) Gadain, a lignan from Jatropha gossypiifolia. Phytochemistry 23:2323–2327

    Article  CAS  Google Scholar 

  • Baraguey C, Blond A, Correia I, Pousset JL, Bodo B, Auvin-Guette C, Mahafacyclin A (2000) A cyclic heptapeptide from Jatropha mahafalensis exhibiting β-bulge conformation. Tetrahedron Lett 41:325–329

    Article  CAS  Google Scholar 

  • Baraguey C, Blond A, Cavelier F, Pousset JL, Bodo B, Auvin-Guette C (2001) Isolation, structure and synthesis of mahafacyclin B, a cyclic heptapeptide from the latex of Jatropha mahafalensis. J Chem Soc Perkin Trans 1:2098–3003

    Article  Google Scholar 

  • Berg VDAJJ, Horsten SFAJ, Kettenes VBJJ, Kroes BH, Labadie RP (1995) Multifidin - a cyanoglucoside in the latex of Jatropha multifida. Phytochemistry 40(2):597–598

    Article  Google Scholar 

  • Brum RL, Hond NK, Mazarin MS, Hess SC, Cavalheiro AJ, Monache FD (1998) Jatrowedione. A lathyrane diterpene from Jatropha weddelliana. Phytochemistry 48:1225–1227

    Article  CAS  Google Scholar 

  • Calixto JB, Santana AEG (1987) Pharmacological analysis of the inhibitory effect of Jatrophone, a diterpene isolated from Jatropha elliptica on smooth and cardiac muscle. Phytother Res 1:122–126

    Article  CAS  Google Scholar 

  • Carels N (2009) Jatropha curcas: a review. Adv Bot Res 50:49–56

    Google Scholar 

  • Chomnong WN (1990) Investigation of the chemical constituents and cytotoxic activity on Jatropha curcas. Newslett Reg Netw Chem Nat Prod. Southeast Asia 14:19–24

    Google Scholar 

  • Dalziel JM (1955) The useful plants of west-tropical Africa. Crown Agents for Overseas Governments and Administration, London, p 147

    Google Scholar 

  • Das B, Das R (1995) Gossypifan, a lignan from Jatropha gossypiifolia. Phytochemistry 40:931–932

    Article  CAS  Google Scholar 

  • Das B, Rao SP, Srinivas KVNS, Das R (1996) Jatrodien, a lignan from stems of Jatropha gossypiifolia. Phytochemistry 41:985–987

    Article  CAS  Google Scholar 

  • Das B, Kashinatham A, Venkataiah B, Srinivas KVNS, Mahender G, Reddy MR, Cleomiscosin A (2003) A coumarino-lignoid from Jatropha gossypiifolia. Biochem Sys Ecol 31:1189–1191

    Article  CAS  Google Scholar 

  • Das B, Reddy KR, Ravikanth B, Raju TV, Sridhar B, Khan PU et al (2009) Multifidone: a novel cytotoxic lathyrane-type diterpene having an unusual six-membered a ring from Jatropha multifida. Bioorg Med Chem Lett 19:77–79

    Article  PubMed  CAS  Google Scholar 

  • Debnath M, Verma HN (2008) Effect of phytoprotein treatment on Jatropha curcas for wasteland reclamation. Afr J Biotechnol 7:613–616

    CAS  Google Scholar 

  • Delgado MJ, Parado TE (1989) Potential multipurpose agroforestry crops identified for the Mexican Tropics. In: Wickens GE, Haq N, Day P (eds) New crops for food and industry. Chapman and Hall, London

    Google Scholar 

  • Devappa RK, Darukeshwara J, RathinaRaj K, Narasimhamurthy K, Saibaba P, Bhagya S (2008) Toxicity studies of detoxified Jatropha meal (Jatropha curcas) in rats. Food Chem Toxicol 46:3621–3625

    Article  Google Scholar 

  • Devappa RK, Makkar HPS, Becker K (2010a) Jatropha toxicity—a review. J Toxicol Environ Health Part B 13:476–477

    Article  CAS  Google Scholar 

  • Devappa RK, Makkar HPS, Becker K (2010b) Nutritional, biochemical, and pharmaceutical potential of proteins and peptides from Jatropha: review. J Agric Food Chem 58:6543–6545

    Article  PubMed  CAS  Google Scholar 

  • Devappa RK, Makkar HPS, Becker K (2010c) Optimization of conditions for the extraction of phorbol esters from Jatropha oil. Biomass Bioenergy 34:1125–1133

    Article  CAS  Google Scholar 

  • Donlaporn S, Suntornsuk W (2010) Antifungal activities of ethanolic extract from Jatropha curcas seed cake. J Microbiol Biotechnol 20:319–324

    Google Scholar 

  • El-Badwi SM, Adam SE, Hapke HJ (1995) Comparative toxicity of Ricinus communis and Jatropha curcas in brown Hisex chicks. Dtsch Tierarztl Wochenschr 102:75–77

    PubMed  CAS  Google Scholar 

  • Eswaran N, Parameswaran S, Sathram B, Anantharaman B, Kumar GRK, Johnson TS (2010) Yeast functional screen to identify genetic determinants capable of conferring abiotic stress tolerance in Jatropha curcas. BMC Biotechnol 10:23

    Article  PubMed  Google Scholar 

  • Evans FJ (1986) Environmental hazards of diterpene esters from plants. In: Evans FJ (ed) Naturally occurring phorbol esters. CRC press, Boca Raton, FL, pp 171–215

    Google Scholar 

  • Fang R, Shenghua W, Xia GZ, Liang G, Qin W, Ling T et al (2005) Identification of curcin by western blot in calli generated from explants of Jatropha curcas L. J Sich Uni (Nat Sci Edn) 42:206–209

    Google Scholar 

  • FAO report (2010) Jatropha: a smallholder bioenergy crop. In: Brittaine R, Lutaladio N (eds) The potential for pro-poor development, vol 8. Food and Agriculture Organization of the UN, Rome, pp 1–96

    Google Scholar 

  • Francis G, Edinger R, Becker K (2005) A concept for simultaneous wasteland reclamation, fuel production, and socio-economic development in degraded areas in India: need, potential and perspectives of Jatropha plantations. Nat Resour Forum 29:12–14

    Article  Google Scholar 

  • Garcia RP, Lawas P (1990) Potential plant extracts for the control of Azolla fungal pathogens. Phillipp Agri 73:343–348

    Google Scholar 

  • Ghosh A, Patolia JS, Chaudhary DR, Chikara J, Rao SN, Kumar D et al (2007) Response of Jatropha curcas under different spacing to Jatropha de-oiled cake. FACT Foundation, The Netherlands. Available from http://www.fact-fuels.org. Accessed March 2012

  • Goel G, Makkar HPS, Francis G, Becker K (2007) Phorbol esters: structure, biological activity and toxicity in animals. Int J Toxicol 26:279–288

    Article  PubMed  CAS  Google Scholar 

  • Goonasekera MM, Gunawardana VK, Jayasena K, Mohammed SG, Balasubramaniam S (1995) Pregnancy terminating effect of Jatropha curcas in rats. J Ethnopharmacol 47:117–123

    Article  PubMed  CAS  Google Scholar 

  • Guette AC, Baraguey C, Blond A, Pousset J, Bodo B, Cyclogossine B (1997) A cyclic octapeptide from Jatropha gossypiifolia. J Nat Prod 60:1155–1157

    Article  Google Scholar 

  • Guette AC, Baraguey C, Blond A, Xavier HS, Pousset JL, Bodo B (1999) Pohlianins A, B and C, cyclic peptides from the latex of Jatropha pohliana ssp. Molissima. Tetrahedron 55:11495–11510

    Article  Google Scholar 

  • Gupta A, Gupta R (1997) A survey of plants for presence of cholinesterase activity. Phytochemistry 46:827–831

    Article  CAS  Google Scholar 

  • Haas W, Mittelbach M (2000) Detoxification experiments with the seed oil from Jatropha curcas L. Ind Crops Prod 12:111–118

    Article  CAS  Google Scholar 

  • Hirschmann SG, Tsichritzis F, Jakupovic J (1992) Diterpenes and a lignan from Jatropha grossidentata. Phytochemistry 31:1731–1735

    PubMed  CAS  Google Scholar 

  • Horiuchi T, Fujiki H, Hirota M, Suttajit M, Suganuma M, Yoshioka A et al (1987) Presence of tumor promoters in the seed oil of Jatropha curcas L. from Thailand. Jpn J Cancer Res 78:223–226

    PubMed  CAS  Google Scholar 

  • Huang MX, Hou P, Wei Q, Xu Y, Chen F (2008) A ribosome-inactivating protein (Curcin 2) induced from Jatropha curcas can reduce viral and fungal infection in transgenic tobacco. Plant Growth Regul 54:115–123

    Article  CAS  Google Scholar 

  • Jamil S, Abhilash PC, Singh N, Sharma P (2009) Jatropha curcas: A potential crop for phytoremediation of coal fly ash. J Hazard Mater 172:269–275

    Article  PubMed  CAS  Google Scholar 

  • Jing L (2005) Study of insecticidal active components in Jatropha curcas L. seed on its extraction, isolation and toxicity action mechanism. Ph.D. dissertation, Sichuan University. http://www.fabiao.net/thread-1513285-1-1.html

  • Jing L, Fang Y, Ying X, Wenxing H, Meng X, Syed MN, Fang C (2005) Toxic impact of ingested Jatropherol-I on selected enzymatic activities and the ultra structure of midgut cells in silkworm, Bombyx mori L. J Appl Entomol 129:98–104

    Article  CAS  Google Scholar 

  • Kosasi S, Van Der Sluis WG, Labadie RP (1989) Multifidol and multifidol glucoside from the latex of Jatropha multifida. Phytochemistry 28:2439–2441

    Article  CAS  Google Scholar 

  • Kumar A, Sharma S (2008) An evaluation of multipurpose oil seed crop for industrial uses (Jatropha curcas): a review. Ind Crops Prod 28:1–10

    Article  CAS  Google Scholar 

  • Kumar PV, Chauhan NS, Padh H, Rajani M (2006) Search for antibacterial and antifungal agents from selected Indian medicinal plants. J Ethnobiol Pharmacol 107:182–188

    Google Scholar 

  • Kumar GRK, Eswaran N, Johnson TS (2011) Isolation of high-quality RNA from various tissues of Jatropha curcas for downstream applications. Anal Biochem 413:63–65

    Article  PubMed  CAS  Google Scholar 

  • Kupchan SM, Sigel CW, Matz MJ (1970) Jatrophone, a novel macrocyclic diterpeniod tumor inhibitor from Jatropha gossypiifolia. J Am Chem Soc 92:4476–4477

    Article  CAS  Google Scholar 

  • Lin J, Yan F, Tang L, Chen F (2003) Antitumor effects of curcin from seeds of Jatropha curcas. Acta Pharmacol Sin 24:241–246

    PubMed  CAS  Google Scholar 

  • Lin J, Zhou X, Wang J, Jiang P, Tang K (2010) Purification and characterization of curcin, a toxic lectin from the seed of Jatropha curcas. Prep Biochem Biotechnol 40:107–108

    Article  PubMed  CAS  Google Scholar 

  • Liu SY, Sporer F, Wink M, Jourdane J, Henning R, Li YL et al (1997) Anthraquinones in Rheum palmatum and Rumex dentatus (Polygonaceae and phorbol esters) from Jatropha curcas (Euphorbiaceae) with molluscicidal activity against the schistosomias vector snails Oncomelania, Biomphalaria and Bulinus. Trop Med Int Health 2:179–188

    Article  PubMed  CAS  Google Scholar 

  • MacNeil A, Sumba OP, Lutzke ML, Moormann A, Rochford R (2003) Activation of the Epstein–Barr virus lytic cycle by the latex of the plant Euphorbia tirucalli. Br J Cancer 88:1566–1569

    Article  PubMed  CAS  Google Scholar 

  • Mahanta N, Gupta A, Khare SK (2008) Production of protease and lipase by solvent tolerant Pseudomonas aeruginosa PseA in solid-state fermentation using Jatropha curcas seed cake as substrate. Bioresour Technol 99:1729–1735

    Article  PubMed  CAS  Google Scholar 

  • Makkar HPS, Becker K (1997) Potential of Jatropha curcas seed meal asa protein supplement to livestock feed, constraints to its utilization and possible strategies to overcome constraints to its utilization. In Proceedings Jatropha 1997: International symposium on Biofuels and Industrial Products from Jatropha curcas and other tropical oil seed plants, February 23–27, Managua, Mexico.

    Article  CAS  Google Scholar 

  • Makkar HPS, Becker K (2010) Are phorbol esters degraded by rumen microbes? J Sci Food Agric 90:1562–1565

    Article  PubMed  CAS  Google Scholar 

  • Makkar HPS, Becker K, Sporer F, Wink M (1997) Studies on nutritive potential and toxic constituents of different provenances of Jatropha curcas. J Agric Food Chem 45:3152–3157

    Article  CAS  Google Scholar 

  • Makkar HPS, Aderibigbe AO, Becker K (1998a) Comparative evaluation of non-toxic and toxic varieties of Jatropha curcas for chemical composition, digestibility, protein degradability and toxic factors. Food Chem 62:207–215

    Article  CAS  Google Scholar 

  • Makkar HPS, Becker K, Schmook B (1998b) Edible provenances of Jatropha curcas from Quintana Roo state of Mexico and effect of roasting on antinutrient and toxic factors in seeds. Plant Foods Hum Nutr 52:31–36

    Article  PubMed  CAS  Google Scholar 

  • Makkar HPS, Francis G, Becker K (2007) Bioactivity of phytochemicals in some lesser known plants and their effects and potential applications in livestock and aquaculture production ­systems. Animal 1:1371–1391

    Article  PubMed  CAS  Google Scholar 

  • Makkar HPS, Jeroen M, Becker K (2009) Removal and degradation of phorbol esters during pre-treatment and transesterification of Jatropha curcas oil. J Am Oil Chem Soc 86:173–181

    Article  CAS  Google Scholar 

  • Makkar HPS, Kumar V, Oyeleye OO, Akinleye AO, Angulo-Escalante MA, Becker K (2011) Jatropha platyphylla, a new non-toxic Jatropha species: physical properties and chemical constituents including toxic and antinutritional factors of seeds. Food Chem 125:63–71

    Article  CAS  Google Scholar 

  • Mangkoedihardjo S, Surahmaida (2008) Jatropha curcas L. for phytoremediation of lead and cadmium polluted soil. World Appl Sci J 4:519–522

    Google Scholar 

  • Marquez B, Neuville L, Moreau NJ, Genet JP, Santos AFD, Andrade MCCD et al (2005) Multidrug resistance reversal agent from Jatropha elliptica. Phytochemistry 66:1804–1811

    Article  PubMed  CAS  Google Scholar 

  • Martinez-Herrera J, Siddhuraju P, Francis G, Da’vila-Ortız G, Becker K (2006) Chemical composition, toxic/antimetabolic constituents, and effects of different treatments on their levels, in four provenances of Jatropha curcas L. from Mexico. Food Chem 96:80–89

    Article  CAS  Google Scholar 

  • Mujumdar AM, Misar AV (2004) Local anti inflammatory activity of Jatropha curcas roots in mice. J Ethnopharmacol 90:11–15

    Article  PubMed  CAS  Google Scholar 

  • Mujumdar AM, Upadye AS, Misar AV (2000) Studies on antidiarrhoeal activity of Jatropha curcas root extract in albino mice. J Ethnopharmacol 70:183–187

    Article  PubMed  CAS  Google Scholar 

  • Nath LK, Dutta SK (1992) Wound healing response of the proteolytic enzyme curcain. Ind J Pharmacol 24:114–115

    Google Scholar 

  • Ochse JJ (1931) Vegetables of the Dutch East Indies. A. Ashernand Co/Hacquebard, Amsterdam, reprinted 1980

    Google Scholar 

  • Oduola T, Popoola GB, Avwioro OG, Oduola TA, Ademosun AA, Lawal MO (2007) Use of Jatropha gossypiifolia stem latex as a hemostatic agent: how safe is it? J Med Plant Res 1:14–17

    Google Scholar 

  • Odusote OM, Abioye AO, Rotibi MO (2002) Jatropha curcas seed oil Linn (Euphorbiaceae) contraceptive activity and on oral formulation. Nig Qt J Hosp Med 12:44–47

    Google Scholar 

  • Osoniyi O, Onajobi F (2003) Coagulant and anticoagulant activities in Jatropha curcas latex. J Ethnopharmacol 89:101–105

    Article  PubMed  Google Scholar 

  • Parthiban KT, Kumar RS, Thiyagarajan P, Subbulakshmi V, Vennila S, Rao MG (2009) Hybrid progenies in Jatropha—a new development. Curr Sci 96:815–823

    CAS  Google Scholar 

  • Pertino M, Schmeda-Hirschmann G, Rodrıguez JA, Theoduloz C (2007) Gastroprotective effect and cytotoxicity of terpenes from the Paraguayan crude drug “yagua rova” (Jatropha isabelli.). J Ethnopharmacol 111:553–559

    Article  PubMed  CAS  Google Scholar 

  • Radhakrishnan P (2007) Contribution of de-oiled cakes in carbon sequestration and as a source of energy, in Indian agriculture—need for a policy initiative. In: Proceedings of the 4th international biofuels conference, New Delhi, 1–2 Feb 2007. Winrock International India, New Delhi

    Google Scholar 

  • Rug M, Ruppel A (2000) Toxic activities of the plant Jatropha curcas against intermediate snail hosts and larvae of schistosomes. Trop Med Int Health 5:423–430

    Article  PubMed  CAS  Google Scholar 

  • Santosh KV, Juwarkar AA, Kumar GP, Thawale PR, Singh SK, Chakrabarti T (2009) Bioaccumulation and phyto-translocation of arsenic, chromium and zinc by Jatropha curcas L.: impact of dairy sludge and biofertilizer. Bioresour Technol 100:4616–4622

    Article  Google Scholar 

  • Siddhuraju P, Makkar HPS, Becker K (2002) The effect of ionising radiation on antinutritional factors and the nutritional value of plant materials with reference to human and animal food. Food Chem 78:187–195

    Article  CAS  Google Scholar 

  • Thangavelu R, Sundararaju P, Sathiamoorthy S (2004) Management of anthracnose disease of banana caused by Colletotrichum musae using plant extracts. J Hort Sci Biotechnol 79:664–668

    CAS  Google Scholar 

  • Varshney A, Johnson TS (2010) Efficient plant regeneration from immature embryo cultures of Jatropha curcas, a biodiesel plant. Plant Biotechnol Rep 4:139–148

    Article  Google Scholar 

  • Wani S, Sreedevi TK, Marimuthu S (2008) Pro-poor biodiesel initiative for rehabilitating degraded drylands. In: International consultation on pro-poor Jatropha development, IFAD, Rome, 10–11 April 2008. Available from http://www.ifad.org/events/jatropha/. Accessed March 2012

  • Wei Q, Liao Y, Chen Y, Wang SH, Xu Y, Tang L et al (2005) Isolation, characterization and antifungal activity of β- 1,3-glucanase from seeds of Jatropha curcas. S Afr J Bot 71:95–99

    CAS  Google Scholar 

  • Wink M, Koschmieder C, Sauerwein M, Sporer F (1997) Phorbol esters of J. curcas: biological activities and potential applications. In: Gübitz GM, Mittelbach M, Trabi M (eds) Biofuel and industrial products from Jatropha curcas. Dbv-Verlag Univ. Graz, Graz, pp 160–166

    Google Scholar 

  • Zippel J, Wells T, Hensel A (2010) Arabinogalactan protein from Jatropha curcas L. seeds as TGFβ1-mediated inductor of keratinocyte in vitro differentiation and stimulation of GM CSF, HGF, KGF and in organotypic skin equivalents. Fitoterapia 81:772–778

    Article  PubMed  CAS  Google Scholar 

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Kumar, G.R.K., Bapat, V.A., Johnson, T.S. (2012). Phorbol Esters and Other Toxic Constituents of Jatropha curcas L.. In: Carels, N., Sujatha, M., Bahadur, B. (eds) Jatropha, Challenges for a New Energy Crop. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-4806-8_24

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