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Review Medicinal property, phytochemistry and pharmacology of several Jatropha species (Euphorbiaceae): A review Carla W. Sabandar a , Norizan Ahmat a,, Faridahanim Mohd Jaafar a , I. Sahidin b a Faculty of Applied Sciences, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor, Malaysia b Department of Chemistry, Faculty of Mathematics and Natural Sciences, Haluoleo University, Kampus Hijau Bumi Tridharma Anduonohu, Kendari, Sulawesi Tenggara, Indonesia article info Article history: Received 23 February 2012 Received in revised form 21 September 2012 Available online 12 November 2012 Keywords: Euphorbiaceae Jatropha Medicinal properties Phytochemical Pharmacology abstract The genus Jatropha (Euphorbiaceae) comprises of about 170 species of woody trees, shrubs, subshrubs or herbs in the seasonally dry tropics of the Old and the New World. They are used in medicinal folklore to cure various diseases of 80% of the human population in Africa, Asia and Latin America. Species from this genus have been popular to cure stomachache, toothache, swelling, inflammation, leprosy, dysentery, dyscrasia, vertigo, anemia, diabetis, as well as to treat HIV and tumor, opthalmia, ringworm, ulcers, malaria, skin diseases, bronchitis, asthma and as an aphrodisiac. They are also employed as ornamental plants and energy crops. Cyclic peptides alkaloids, diterpenes and miscellaneous compounds have been reported from this genus. Extracts and pure compounds of plants from this genus are reported for cyto- toxicity, tumor-promoting, antimicrobial, antiprotozoal, anticoagulant, immunomodulating, anti-inflam- matory, antioxidant, protoscolicidal, insecticidal, molluscicidal, inhibition AChE and toxicity activities. Ó 2012 Elsevier Ltd. All rights reserved. 1. Introduction The genus Jatropha that belongs to tribe Joannesieae in the Euphorbiaceae family contains approximately 170 known species. The name Jatropha is derived from the Greek word ‘‘jatros’’ (doctor) and ‘‘trophe’’ (food), which implies its medicinal uses (Kumar and Sharma, 2008). Jatropha is a large genus of diverse growth forms and are attractive monoecious or dioecious plants. These species are woody trees, shrubs and subshrubs of disjunct distribution in the seasonally dry tropics of the Old and the New World. Two dis- tinct groups were recently recognized, subgenus Jatropha that in- cludes the African, Indian, South American, Antillian and two of the relict North American taxa, and species of subgenus Curcas which are predominant in Mexican with a few extending into Texas and Arizona (Dehgan, 1982). Jatropha species are used in tra- ditional folklore medicine to cure various ailments in Africa, Asia and Latin America (Burkill, 1994), as ornamental plants and energy crops (Heller, 1996). Their usage as traditional health remedies is the most popular for 80% of the world population in Asia, Latin America and Africa and is reported to have minimal side effects (Cowan, 1999). Several known species from genus Jatropha have been reported for their medicinal uses, chemical constituents and biological activities such as Jatropha curcas Linn., J. chevalieri Beille, J. elliptica Muell. Arg., J. gaumeri Greenm., J. glandulifera Roxb., J. gossypiifolia Linn., J. grossidentata Pax et. Hoffm., J. integerrima Jacq., J. macran- tha, J. mahafalensis Jum and H. Perrier, J. multifida Linn., J. nana Dalz, J. podagrica Hook, J. pohliana Muell. Arg., J. tanjorensis Ellis and Sar- oja, J. unicostata and J. weddelliana Baillon. This review describes the medicinal properties, chemical constituents and biological activities of Jatropha. 2. Medicinal properties Jatropha species have been used as medicinal plants by native people in the tropical and subtropical countries (Openshaw, 2000). Table 1 lists the medicinal usage of Jatropha while Table 2 describes the medicinal practices by natives of tropical and sub- tropical countries. Jatropha species are famous for the purgative effect of the seed oil. This purgative effect has been directed to cure digestive system symptoms i.e. diarrhoea, dysentery, vomiting, retching and stom- achache. Contrast to its purgative effect, Lioglier (1990) reported that seeds of Jatropha species are highly toxic and advised that they not be used in herbal medicine. Besides seed oil, leaf of some Jatro- pha species also have similar purgative effect. The leaf of J. integerr- ima is reported to possess a high purgative effect which provoked vomiting and caused dehydration that its consumption as herbal medicine was not advised (Mongkolvisut et al., 2006). In addition, some parts of Jatropha plants are employed to heal skin-related ailments. The seed oil, latex, leaf, stem bark or root of Jatropha plants are pounded and applied on infected skin i.e. 0031-9422/$ - see front matter Ó 2012 Elsevier Ltd. All rights reserved. http://dx.doi.org/10.1016/j.phytochem.2012.10.009 Corresponding author. Tel.: +60 355444619; fax: +60 355444562. E-mail address: [email protected] (N. Ahmat). Phytochemistry 85 (2013) 7–29 Contents lists available at SciVerse ScienceDirect Phytochemistry journal homepage: www.elsevier.com/locate/phytochem

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Page 1: Medicinal property, phytochemistry and pharmacology of ... macrantha - Various conditions.p… · Review Medicinal property, phytochemistry and pharmacology of several Jatropha species

Phytochemistry 85 (2013) 7–29

Contents lists available at SciVerse ScienceDirect

Phytochemistry

journal homepage: www.elsevier .com/locate /phytochem

Review

Medicinal property, phytochemistry and pharmacology of several Jatrophaspecies (Euphorbiaceae): A review

Carla W. Sabandar a, Norizan Ahmat a,⇑, Faridahanim Mohd Jaafar a, I. Sahidin b

a Faculty of Applied Sciences, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor, Malaysiab Department of Chemistry, Faculty of Mathematics and Natural Sciences, Haluoleo University, Kampus Hijau Bumi Tridharma Anduonohu, Kendari, Sulawesi Tenggara, Indonesia

a r t i c l e i n f o a b s t r a c t

Article history:Received 23 February 2012Received in revised form 21 September 2012Available online 12 November 2012

Keywords:EuphorbiaceaeJatrophaMedicinal propertiesPhytochemicalPharmacology

0031-9422/$ - see front matter � 2012 Elsevier Ltd. Ahttp://dx.doi.org/10.1016/j.phytochem.2012.10.009

⇑ Corresponding author. Tel.: +60 355444619; fax:E-mail address: [email protected] (N.

The genus Jatropha (Euphorbiaceae) comprises of about 170 species of woody trees, shrubs, subshrubs orherbs in the seasonally dry tropics of the Old and the New World. They are used in medicinal folklore tocure various diseases of 80% of the human population in Africa, Asia and Latin America. Species from thisgenus have been popular to cure stomachache, toothache, swelling, inflammation, leprosy, dysentery,dyscrasia, vertigo, anemia, diabetis, as well as to treat HIV and tumor, opthalmia, ringworm, ulcers,malaria, skin diseases, bronchitis, asthma and as an aphrodisiac. They are also employed as ornamentalplants and energy crops. Cyclic peptides alkaloids, diterpenes and miscellaneous compounds have beenreported from this genus. Extracts and pure compounds of plants from this genus are reported for cyto-toxicity, tumor-promoting, antimicrobial, antiprotozoal, anticoagulant, immunomodulating, anti-inflam-matory, antioxidant, protoscolicidal, insecticidal, molluscicidal, inhibition AChE and toxicity activities.

� 2012 Elsevier Ltd. All rights reserved.

1. Introduction

The genus Jatropha that belongs to tribe Joannesieae in theEuphorbiaceae family contains approximately 170 known species.The name Jatropha is derived from the Greek word ‘‘jatros’’ (doctor)and ‘‘trophe’’ (food), which implies its medicinal uses (Kumar andSharma, 2008). Jatropha is a large genus of diverse growth formsand are attractive monoecious or dioecious plants. These speciesare woody trees, shrubs and subshrubs of disjunct distribution inthe seasonally dry tropics of the Old and the New World. Two dis-tinct groups were recently recognized, subgenus Jatropha that in-cludes the African, Indian, South American, Antillian and two ofthe relict North American taxa, and species of subgenus Curcaswhich are predominant in Mexican with a few extending intoTexas and Arizona (Dehgan, 1982). Jatropha species are used in tra-ditional folklore medicine to cure various ailments in Africa, Asiaand Latin America (Burkill, 1994), as ornamental plants and energycrops (Heller, 1996). Their usage as traditional health remedies isthe most popular for 80% of the world population in Asia, LatinAmerica and Africa and is reported to have minimal side effects(Cowan, 1999).

Several known species from genus Jatropha have been reportedfor their medicinal uses, chemical constituents and biologicalactivities such as Jatropha curcas Linn., J. chevalieri Beille, J. ellipticaMuell. Arg., J. gaumeri Greenm., J. glandulifera Roxb., J. gossypiifolia

ll rights reserved.

+60 355444562.Ahmat).

Linn., J. grossidentata Pax et. Hoffm., J. integerrima Jacq., J. macran-tha, J. mahafalensis Jum and H. Perrier, J. multifida Linn., J. nana Dalz,J. podagrica Hook, J. pohliana Muell. Arg., J. tanjorensis Ellis and Sar-oja, J. unicostata and J. weddelliana Baillon. This review describesthe medicinal properties, chemical constituents and biologicalactivities of Jatropha.

2. Medicinal properties

Jatropha species have been used as medicinal plants by nativepeople in the tropical and subtropical countries (Openshaw,2000). Table 1 lists the medicinal usage of Jatropha while Table 2describes the medicinal practices by natives of tropical and sub-tropical countries.

Jatropha species are famous for the purgative effect of the seedoil. This purgative effect has been directed to cure digestive systemsymptoms i.e. diarrhoea, dysentery, vomiting, retching and stom-achache. Contrast to its purgative effect, Lioglier (1990) reportedthat seeds of Jatropha species are highly toxic and advised that theynot be used in herbal medicine. Besides seed oil, leaf of some Jatro-pha species also have similar purgative effect. The leaf of J. integerr-ima is reported to possess a high purgative effect which provokedvomiting and caused dehydration that its consumption as herbalmedicine was not advised (Mongkolvisut et al., 2006).

In addition, some parts of Jatropha plants are employed to healskin-related ailments. The seed oil, latex, leaf, stem bark or root ofJatropha plants are pounded and applied on infected skin i.e.

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Table 1Medicinal uses of Jatropha species.

Species Parts Medicinal use References

J. curcas Whole Wounds; allergies; burns; cuts Heller (1996), Kaushik and Kumar (2004)

Diarrhea Patil (2005)Seed oil Purgative Kirtikar and Basu (1980)

Rheumatic pain; skin diseases; eczema Heller (1996)Fruit and seed Abdominal complains; dysentery; urinary

discharge; fistula; heart disease;antihelminthic

Kirtikar and Basu (1980)

Stem/bark HIV; tumor Heller (1996), Kaushik and Kumar (2004)Sap/latex Toothache; stypic Heller (1996), Kaushik and Kumar (2004)

J. elliptica – Anti-ulcer; urinary discharge; neoplasia Dos Santos and Sant’Ana (1999)Abdominal complaints Flores and Ricalde (1996)

J. gaumeri Exudates Fever; bone fracture Comerford (1996)Mouth blister Flores and Ricalde (1996)Anti-inflammatory Nayak and Patel (2009)

J. glandulifera Seed oil; root Sinuses; ringworm; antiparalytic Nayak and Patel (2009)Rheumatic pain; purgative Joy et al. (1998)

Leaf Asthma; bronchitis; as analgesic;emmenagogue; scorpion-sting

Nayak and Patel (2009)

J. gossypifolia Whole Dysphonia; dyscrasia Kirtikar and Basu (1980)Antibiotic; insecticidal; toothache Balee (1994)

Seed oil Anti-ulcer; leprosy; ringworm Banerji et al. (1993)Purgative Asprey and Thornton (2005)

Leaf Constipation; vertigo; diarrhea; purgative;skin diseases; mouth blister; cancer

Burkill (1994)

Stomachache; eczema; carbuncles; itches;swelling; venereal disease; blood purifier

Banerji et al. (1993)

Root Leprosy; antidote Kirtikar and Basu (1980)Shamanic practice Schmeda-Hirschmann (1993)

J. integerrima Leaf Purgative Mongkolvisut et al. (2006)

J. nana – Opthalmia Bhagat and Kurkani (2010)

J. mahafalensis Seed oil Hair delouse Schmelzer and Gurib-Fakim (2008)Root Invigorating drink Schmelzer and Gurib-Fakim (2008)

J. multifida Seed oil Purgative Dehgan (1982), Burkill (1994)Abortifacient Kirtikar and Basu (1980)

Bark/leaf Neurodermatitis; eczema; itches Shu et al. (2008)Latex Wounds Kirtikar and Basu (1980), Burkill (1994)Root Microbial infections Aiyelaagbe (2000)

Anti-ulcer Kirtikar and Basu (1980)Gonorrhea; urinary discharge Burkill (1994)

J. podagrica – Antibiotic; tumor; insect antifeedant Aiyelaagbe and Gloer (2008)

J. unicostata Sap (colorless) Chest pain; retching; vomiting;stomachache; eye infections

Miller and Morris (2004)

Sap (red) Purgative; haemostatic Miller and Morris (2004)

(–): not mentioned.

8 C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29

eczema, itches, carbuncles, mouth blisters, wounds and swelling(Kirtikar and Basu, 1980; Banerji et al., 1993; Burkill, 1994; Heller,1996). They are also believed to cure venereal diseases and urinarydischarge (Kirtikar and Basu, 1980; Banerji et al., 1993). The rootsof J. gossypiifolia and J. multifida have long been applied on peoplesuffering from leprosy and gonorrhea, respectively (Kirtikar andBasu, 1980; Burkill, 1994). Such usage suggested that Jatrophaplants may contain compounds with antimicrobial properties.

3. Phytochemistry

Investigations of the chemical constituents of Jatropha plantsresulted in the isolation of alkaloids, cyclic peptides, terpenes (amonoterpene, sesquiterpenes, diterpenes and triterpenes), flavo-noids, lignans, coumarins, coumarino-lignoids, a non-cyanogenicglucoside, phloroglucinols, ester ferulates, phenolics, deoxypreus-somerins and fatty acids.

3.1. Cyclic peptide alkaloids

All cyclic peptides reported for Jatropha species were isolatedfrom the latex. Cyclic heptapeptides (7, 9, 10, 13, 14, 16–18), cyclicoctapeptides (1, 3, 4–5, 8, 19), cyclic nonapeptides (2, 6, 12, 15) anda cyclic decapeptide (11) reported from eight Jatropha species arelisted in Table 3 and shown in Fig. 1.

3.2. Diterpenoids

Jatropha plants contain a rich source of cyclic diterpenes havingtigliane, casbene, daphnane, lathyrane, jatrophane, podocarpaneand rhamnofolane skeletons. These skeletons are displayed inFig. 2. Tigliane-type diterpenes are found in the seed oil of J. curcasand J. gossypiifolia as phorbol esters which are polyunsaturatedditerpene diesters (20–26) (Hirota et al., 1988; Haas et al., 2002;Jing et al., 2005). Martinez-Herrera et al. (2006) investigated thephorbol ester concentration in the seed kernels of four

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Table 2Medicinal practice of Jatropha species in some countries.

Species Medicinal Country or region References

J. curcas Decoction of the leaves is boiled with Azadirachta indica and Caricapapaya to cure malaria. Latex from the twigs is used to treatmouth sores

Ghana Asase et al. (2005)

Decoction of the leaves is applied as a lactogogue. The leaf juice ofthis plant treated with lime or lemon and boiled juice of the youngleaves are used as a bath and drunk for curing fever

Cape Verde Islands Kirtikar and Basu (1980)

The latex collected from the plant cortex is applied to externalwounds. It is also known as wound-healing agents on superficialand internal wounds such gastric ulcers

Peru Villegas et al. (1997)

Juices and/or poultices of bark or fruit or root are used to cureleismania

Oyapock, French Guiana Odonne et al. (2011)

J. chevalieri The leaves and latex are considered as haemostatic and applieddirectly on wounds to stop bleeding

Senegal Schmelzer and Gurib-Fakim(2008)

The latex of J. chevalieri is also locally applied to mumps and theroot extract is taken for treating complications of syphilis andleprosy

Senegal Schmelzer and Gurib-Fakim(2008)

The oil from the grilled seeds is applied to boils and abscesses.Powdered seed mixed with lizard fat, is massaged onto the skin totreat spleen pain

Nigeria Schmelzer and Gurib-Fakim(2008)

The leaves are used to apply henna to the skin but it is toxic toherbivores

Nigeria Schmelzer and Gurib-Fakim(2008)

J. elliptica Used to treat severe itches, snake bites and syphilis Brazil Campos et al. (2007)

J. gaumeri Skin cancer treatment Mexico Alonso-Castro et al. (2011)Gastrointestinal disorders and dermatological conditions Peninsula of Yucatan, Mexico Ankli et al. (2002)Bowel diseases Mayan, Mexico Vera-Ku et al. (2010)

J. gossypiifolia Diarrhoea treatment IndiaBrazil Dash and Padhy (2006)Aspreyand Thornton (2005)

The root is used to dysentery India Dabur et al. (2007)Decoction of the plant is used to treat wound and reduce pain.Hunters use this plant to cure snakebites, scorpion stings, injuriesand mange of their dogs wound, sores and swelling treatment

Trinidad Lans et al. (2001)Tobago and Trinidad Lans (2007)

Decoction of leaves of J. gossypiifolia, Combretum ghaselensis andthe whole part of Ocimum canum are used to treat malaria

Ghana Asase et al. (2005)

Mouth cancer treatment Ekiti, Nigeria Kayode and Omotoyinbo (2008)Extract from the fresh leaf or crushed leaf is routinely used byherbalists and local people to stop bleeding from the skin andnose

Southern Nigeria Oduola et al. (2005a,b)

Seed oil and tea of leaves used as a laxative Trinidad Asprey and Thornton (2005)The fruits is known as a purgative Suriname Andel et al. (2007)The seed and fruit are used by traditional practitioners andreligious healers to treat leprosy

Bangladesh Mollik et al. (2009)

Decoction and oral administration of leafy stem were used to cureanemia

Togo Koudouvo et al. (2011)

J. grossidentata The stem bark is used as an antiparasitic means Paraguay Tolstikov et al. (1996)

J. macrantha Twig is used as an aphrodisiac for impotency Peru Pardo (2002)Decoction and poultice of the twig is used to treat diabetes andskin ulcers, respectively. It is also considered antitussive and anti-asthmatic to treat asthma, bronchitis and coughs

Peru Pardo (2002)

The roots are ground and boiled. The infusion is taken orally asblood depurative

Peru and Argentina Desmarchelier et al. (1996a,b,1997)

J. multifida The fruit are useful in piles, wounds, enlarged spleen and skindiseases

Cambodia Kirtikar and Basu (1980)

The seeds are regarded as a powerful purgative, aphrodisiac, tonic,vomitting and burning sensation

Cambodia Kirtikar and Basu (1980)

The stem is employed as chewing sticks and used for dental carein. It was reported to heal mouth wounds and mouth microbialinfections

Ekiti, Nigeria Kayode and Omotoyinbo (2008)

The latex is applied externally to wounds and ulcers Indonesia Kosasi et al. (1989a)Plant parts are used by traditional healers for treatment of fungalinfections

Tanzania Hamza et al. (2006)

J. podagrica Malaria treatment Europe Dehgan (1982)

J. tanjorensis Malaria infection and hypertension Nigeria Orhue et al. (2008)The leaves are consumed as a vegetable and known as catholicvegetable and applied in diabetes treatment

Nigeria Mensah et al. (2008)Olayiwolaet al. (2004)

C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29 9

provenances (Castillo de Teayo, Pueblillo, Croatzacoalcos andYautepec) of J. curcas from different agro-climatic regions of Mex-ico. A high concentration of phorbol esters was found in the kernelsof Croatzacoalcos (3.85 mg/g) whereas it was not detected in the

other three provenances. A similar study was carried out by Ahmedand Salimon (2009) which reported the phorbol esters content oftropical J. curcas seeds from Malaysia, Indonesia and India. Thehighest concentration of phorbol esters was found in the seed oil

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Table 3Cyclic peptides isolated from Jatropha species.

Structure number Name of cyclic peptide Jatropha species References

1 Curcacycline A J. curcas Van den Berg et al. (1995a)2 Curcacycline B J. curcas Auvin-Guette et al. (1997a,b)3 Jatrophidin J. curcas; J. pohliana Altei et al. (2007)4 Chevalierin A J. chevalieri Baraguey et al. (1998)5 Chevalierin B J. chevalieri Baraguey et al. (1998)6 Chevalierin C J. chevalieri Baraguey et al. (1998)7 Cyclogossine A J. gossypiifolia Horsten et al. (1996)8 Cyclogossine B J. gossypiifolia Auvin-Guette et al. (1997b)9 Integerrimide A J. integerrima Mongkolvisut et al. (2006)

10 Integerrimide B J. integerrima Mongkolvisut et al. (2006)11 Labaditin J. multifida Kosasi et al. (1989a)12 Biobollein J. multifida Labadie (1993)13 Mahafacyclin A J. mahafalensis Baraguey et al. (2000)14 Mahafacyclin B J. mahafalensis Baraguey et al. (2001)15 Podacycline A J. podagrica Van den Berg et al. (1996)16 Podacycline B J. podagrica Van den Berg et al. (1996)17 Pohlianin A J. pohliana Auvin-Guette et al. (1999)18 Pohlianin B J. pohliana Auvin-Guette et al. (1999)19 Pohlianin C J. pohliana Auvin-Guette et al. (1999)

10 C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29

of Indonesia J. curcas (1.58%) followed by India (0.58%) and Malay-sia (0.23%). Goel et al. (2007) also reported the phorbol ester con-centration from the oil of nontoxic and toxic Mexican varieties ofJatropha species. The nontoxic varieties contained negligible orlow concentration of phorbol esters (2.7 � 103 lg/ml) while thetoxic varieties contained 2.49 � 103 lg/ml of phorbol esters.

Casbene-type diterpenes (29–33) are found in the roots of J. gos-sypiifolia, J. curcas, J. elliptica, J. glandulifera and J. integerrima. Thefirst casbene-type diterpene was isolated by Purushothaman andChandrasekharan (1979) while its derivatives (36–37) were foundthirty years later in another Jatropha species, J. integerrima by Sut-thivaiyakit et al. (2009). Both daphnane (34–37) and podocarpane(67–68) diterpenes found only in J. curcas were isolated by Naeng-chomnong et al. (1986a) and Ravindranath et al. (2004a), respec-tively. Lathyrane (38–57) diterpenes are distributed in J. curcas, J.gaumeri, J. gossypifolia, J. grossidentata, J. multifida, J. podagrica,and J. weddelliana. Falodun et al. (2012) reported the first lathyranediterpene (48) from J. gossypifolia. The first rhamnofolane diterpene(69) from Jatropha species was found in the roots of J. grossidentataby Jakupovic et al. (1988). Liu et al. (2012) found a new rhamnofo-lane diterpene (83) known as a 6/6/6 tricyclic diterpene of arhamnofolane type from the root of J. curcas together with lagos-pholone B derivatives (81–82). Kupchan et al. (1970) pioneeredthe work on J. gossypiifolia and isolated the first jatrophane diter-pene (58) from Jatropha species while Taylor et al. (1983) isolatedthe derivatives of 58 and also 59–60. The structures of these deriv-atives were established by X-ray diffraction method on a singlecrystal by Santopietro et al. (1985). Due to the toxicity of 58,Pertino et al. (2007a) performed biotransformation of 58 by Asper-gillus niger which then afforded 62. The diterpenes mentionedabove are listed in Table 4 and their structures are displayed inFig. 3.

3.3. Miscellaneous compounds

The chemical constituents of J. macrantha, J. nana, J. tanjorensisand J. unicostata are less reported despite their interesting tradi-tional uses. Franke et al. (2004) investigated the relative composi-tion of J. unicostata leaves using GC–MS and detected phytosterols:an unidentified sterol (0.9%), campesterol (4.9%), stigmasterol(36.5%), sitosterol (56.4%), stigmastanol (1.3%); 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%) and dioxosteroids: campest-4-en-3,6-dione (5.6%), stigmast-4,22-diene-3,6-dione (42.2%) and

stigmast-4-en-3,6-dione (52.2%). The latex from J. unicostata maycontain ketosteroids. Bhagat and Kurkani (2010) performed phyto-chemical screening of the aqueous and organic extracts of the driedpowdered leaves and roots of J. nana and found them to containcarbohydrates, proteins, fats, starch, tannins, polyphenols, alka-loids, flavonoids, saponins and steroids. The roots of J. nana are alsoreported to contain lignins, glycosides and anthraquinones. Inaddition, Ehimwenma and Osagie (2007) investigated the compo-sition of the leaves of J. tanjorensis and found bioactive principlessuch as alkaloids, flavonoids, tannins, cardiac glycosides, anthra-quinones and saponins. Other groups of compounds from Jatropha(Table 5) are shown in Fig. 4.

In addition to the fatty acids listed in Table 5, the major fattyacids found in the oil of J. curcas were oleic (41.5–48.8%), linoleic(34.6–44.4%), palmitic (10.5–13.0%), stearic (2.3–2.8%), cis-11-eico-sanoic and cis-11, 14-eicosadienoic acids (Martinez-Herrera et al.,2006). Rao et al. (2009) reported a 32% total oil content from theseeds of J. curcas that was made up of 97.6% neutral lipids, 0.95%glycolipids and 1.45% phospholipids. The phospholipid fraction ofthe oil contained phosphatidyl choline (60.5%), phosphatidyl inosi-tol (24%) and phosphatidyl ethanolamine (15.5%). Other species ofJatropha such as J. gossypiifolia reported 18.5% of 12-hydroxyocta-dec-cis-ricinoleic acid polymers in its seed oil (Hosamami andKatagi, 2008).

Besides fatty acids, proteins were also reported from the seedoil and latex of Jatropha plants. Martinez-Herrera et al. (2006) re-ported the presence of 31–34.5% crude proteins in the seed kernelsof J. curcas. Curcin, a lectin, b-glucanase, esterases (JEA and JEB) andlipase were isolated from the seed oil of J. curcas (Stirpe et al.,1976; Wei et al., 2005; Staubmann et al., 1999a,b). Aquaporinsand betaine aldehyde dehydrogenase are proteins found in theseed oil of J. curcas which function as drought resistant agents(Zhang et al., 2007, 2008) while Nath and Dutta (1991) reportedthe isolation of curcain, a protease from the latex of J. curcas. Allproteins mentioned are known to act as functional proteins(Devappa et al., 2010a,b).

4. Pharmacology

4.1. Cytotoxicity

The extracts of J. curcas, J. gaumeri, J. gossypiifolia and J. macran-tha are reported to be cytotoxic towards melanoma cells, naso-pharynx human carcinoma and Artemia sp (Table 6).

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Fig. 1. Cyclic peptides isolated from Jatropha species.

C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29 11

Some compounds isolated from Jatropha plants have beeninvestigated for their cytotoxicity and three cyclic peptides (9, 10

and 16) showed high activity when treated on several cell lines.Thirteen diterpenes (34–37, 39, 41, 55, 55–59 and 73) have been

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Fig. 2. Diterpene skeletons of Jatropha.

Table 4Diterpenoids from Jatropha species.

Structurenumber

Compound name Diterpene type Species Part References

20 12-Deoxy-16-hydroxyphorbol (DHPB) Tigliane J. curcas Seed oil Hirota et al. (1988)J. gossypiifolia Seed oil Hirota et al. (1988)

21 Jatropha factor C1 Tigliane J. curcas Seed oil Haas et al. (2002)22 Jatropha factor C2 Tigliane J. curcas Seed oil Haas et al. (2002)23 Jatropha factor C3 Tigliane J. curcas Seed oil Haas et al. (2002)24 Jatropha factor C4 Tigliane J. curcas Seed oil Haas et al. (2002)25 Jatropha factor C5 Tigliane J. curcas Seed oil Haas et al. (2002)26 Jatropha factor C6 Tigliane J. curcas Seed oil Haas et al. (2002)27 Jatropherol I Tigliane J. curcas Seed oil Jing et al. (2005)28 Jatropholone A Casbene J. gossypiifolia Root Purushothaman and

Chandrasekharan (1979)J. curcas Root Naengchomnong et al. (1994)J. elliptica Root Goulart et al. (1993)J. glandulifera Root Parthasarathy and Saradhia (1984)

29 Jatropholone B Casbene J. gossypiifolia Root Purushothaman andChandrasekharan (1979)

J. curcas Root Naengchomnong et al. (1994)J. elliptica Root Goulart et al. (1993)

30 2a-Hydroxyjatropholone Casbene J. integerrima Root Sutthivaiyakit et al. (2009)31 2b-Hydroxyjatropholone Casbene J. integerrima Root Sutthivaiyakit et al. (2009)32 Jatrophol Casbene J. curcas Root Naengchomnong et al. (1994)33 Jatrophalactam Casbene J. curcas Root Wang et al. (2009)34 Curcusones A Daphnane J. curcas Root Naengchomnong et al. (1986a)35 Curcusones B Daphnane J. curcas Root Naengchomnong et al. (1986a)36 Curcusones C Daphnane J. curcas Root Naengchomnong et al. (1986a)37 Curcusones D Daphnane J. curcas Root Naengchomnong et al. (1986a)38 Curculathyrane A Lathyrane J. curcas Root Naengchomnong et al. (1986b)39 Curculathyrane B Lathyrane J. curcas Root Naengchomnong et al. (1986b)40 (4E)-Jatrogrossidentadione Lathyrane J. weddelliana Stem Brum et al. (2001)41 15-epi-(4E)-Jatrogrossidentadione Lathyrane J. weddelliana Stem Brum et al. (2001)

J. gaumeri Root Can-Aké et al. (2004)J. multifida Stem Das et al. (2009b)

42 (4E) Jatrogrossidentadione acetate Lathyrane J. multifida Stem Das et al. (2008)43 15-O-acetyl-15-epi-(4E)-jatrogrossidentadione Lathyrane J. curcas Aerial Ravindranath et al. (2004a)44 (14E)-14-O-5,6-epoxyjatrogrossidentadione Lathyrane J. curcas Aerial Ravindranath et al. (2004a)45 15-epi-(4E)-Jatrogrossidentadione acetate Lathyrane J. multifida Stem Das et al. (2010)46 (4Z)-Jatrogrossidentadione Lathyrane J. grossidentata Root Schmeda-Hirschmann et al. (1992)

J. weddelliana Stem Brum et al. (2001)J. podagrica – Aiyelaagbe et al. (2007)

47 15-epi-(4Z)-Jatrogrossidentadione Lathyrane J. grossidentata Root Schmeda-Hirschmann et al. (1992)J. weddelliana Stem Brum et al. (2001)J. podagrica – Aiyelaagbe et al. (2007)

48 Falodone Lathyrane J. gossypifolia Root Falodun et al. (2012)49 Multidione Lathyrane J. multifida Stem Das et al. (2009a)50 Multifidone Lathyrane J. multifida Stem Das et al. (2009b)51 Multifolone Lathyrane J. multifida Stem Das et al. (2008)52 Multifidanol Lathyrane J. multifida Stem Kanth et al. (2011)

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Table 4 (continued)

Structurenumber

Compound name Diterpene type Species Part References

53 Multifidenol Lathyrane J. multifida Stem Kanth et al. (2011)54 Jatrowedione Lathyrane J. weddeliana Root Brum et al. (1998)55 Jatrowediol Lathyrane J. weddeliana Stem Brum et al. (2001)56 Japodagrin Lathyrane J. podagrica Root Aiyelaagbe et al. (2007)57 Japodagrol Lathyrane J. podagrica – Sanni et al. (1988)58 Jatrophone Jatrophane J. gossypiifolia Root Kupchan et al. (1970, 1976)

J. elliptica Rhizome Goulart et al. (1993)J. multifida Stem Das et al. (2009b)

59 Hydroxyjatrophone A Jatrophane J. gossypiifolia Root Taylor et al. (1983)60 Hydroxyjatrophone B Jatrophane J. gossypiifolia Root Taylor et al. (1983)61 Hydroxyjatrophone C Jatrophane J. gossypiifolia Root Taylor et al. (1983)62 9b-Hydroxyisabellione Jatrophane – – Pertino et al. (2007a)63 9b-13a-Hydroxyisabellione Jatrophane J. gossypiifolia Rhizome Pertino et al. (2007c)64 Citlalitrione Jatrophane J. gossypiifolia Whole Das and Venkataiah (1999)

J. multifida Stem Das et al. (2009b)65 Jatrophenone Jatrophane J. gossypiifolia Whole Ravindranath et al. (2003)66 Japodagrone Jatrophane J. podagrica Root Aiyelaagbe et al. (2007)67 3b-Acetoxy-12-methoxy-13-methyl-podocarpa-8,11,13-

triene-7-onePodocarpane J. curcas Aerial Ravindranath et al. (2004a)

68 3b,12-Hydroxy-13-methyl-podocarpa-8,10,13-triene Podocarpane J. curcas Aerial Ravindranath et al. (2004a)69 Jatrogrossidione Rhamnafolane J. grossidentata Root Jakupovic et al. (1988)70 2-epi-Jatrogrossidione Rhamnafolane J. grossidentata Root Schmeda-Hirschmann et al. (1992)

J. gaumeri – Can-Aké et al. (2004)71 Jatrogrossidion Rhamnafolane J. weddelliana Stem Brum et al. (2001)72 Isojatrogrossidione Rhamnafolane J. grossidentata Root Schmeda-Hirschmann et al. (1992)73 epi-Isojatrogrossidione Rhamnafolane J. curcas Aerial Ravindranath et al. (2004a)74 2-Hydroxyisojatrogrossidione Rhamnafolane J. grossidentata Root Schmeda-Hirschmann et al. (1992)

J. weddelliana Stem Brum et al. (2001)J. curcas Aerial Ravindranath et al. (2004a)J. podagrica Root Aiyelaagbe et al. (2007)

75 2-epi-Hydroxyisojatrogrossidione Rhamnafolane J. grossidentata Root Schmeda-Hirschmann et al. (1992)J. weddelliana Stem Brum et al. (2001)J. podagrica Root Aiyelaagbe et al. (2007)

76 Caniojane Rhamnafolane J. curcas Root Ling-yi et al. (1996)J. grossidentata Root Sutthivaiyakit et al. (2003)

77 1,11-Bisepicaniojane Rhamnafolane J. integerrima Root Sutthivaiyakit et al. (2003)78 2-Epicaniojane Rhamnafolane J. integerrima Root Sutthivaiyakit et al. (2003)79 Integerrimene Rhamnafolane J. integerrima Root Sutthivaiyakit et al. (2003)80 Spirocurcasone Rhamnofolane J. curcas Root Chianese et al. (2011)81 Jatrophalactone Rhamnofolane J. curcas Root Liu et al. (2012)82 Jatrophalone Rhamnofolane J. curcas Root Liu et al. (2012)83 Jatrophadiketone Rhamnofolane J. curcas Root Liu et al. (2012)84 Heudelatinone Dinorditerpene J. curcas Aerial Ravindranath et al. (2003)

C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29 13

examined for potential cytotoxicity and out of these 55 possessedthe highest activity. Besides cyclic peptides and diterpenes, a pro-tein isolated from Jatropha plants was also reported to possessantitumor activity. Curcin, a toxic protein from the seeds of J. cur-cas was investigated for its antitumor effect against different celllines like gastric cancer (SGC-7901), mouse myeloma (Sp2/0), car-cinoma (Hela) and human embryo lung diploid (MRC) where themechanistic action of this protein is related to the N-glycosidaseactivity. Curcin was also found to possess powerful inhibitory ac-tion upon protein synthesis in reticulocyte lysate with an IC50 va-lue of 0.19 (0.11–0.27) nmol/L. The IC50 of curcin on SGC-7901,Sp2/0 and human hepatoma were 0.23 (0.15–0.32) mg/L, 0.66(0.35–0.97) mg/L, 3.16 (2.74–3.58) mg/L, respectively. On the otherhand, it is determined that curcin has no toxic effect on Hela andnormal cells (MRC) (Lin-Juan and Tang-Lin, 2003).

4.2. Tumor-promoting activity

Phorbol esters from Jatropha species have been reported to pos-sess tumor-promoting activity where their actions stimulate pro-tein kinase C involved in signal transduction and development ofmost cells and tissues. These actions were found to be responsiblefor skin irritants and tumor promotion (Goel et al., 2007). The

toxicity of J. curcas oil in mouse carcinogenesis has been reportedand the irritant fraction of the oil induced ornithine decarboxylaseand inhibited specific binding of 12-O-tetradecanoylphorbol-13-acetate (TPA) to particulate fraction of mouse skin (Horiuchiet al., 1987). Phorbol ester, 12-deoxy-16-hydroxyphorbol (20) hastumor-promoting activity whereby DHPB (20) showed slightlyweaker biological and biochemical activities than TPA. DHPB (20)induced ornithine decarboxylase in mouse skin (2.8 nmol CO2/30 min/mg protein/34 nmol application), inhibited the specificbinding of [3H]-12-O-tetradecanoylphorbol-13-acetate to phorbolester receptors (50% effective dose, 17.0 nM) and activated proteinkinase C in vitro (50% effective dose, 36.0 nM). However, its role inproducing tumors was found to be non significant in mice (Hirotaet al., 1988).

4.3. Antimicrobial activity

Some Jatropha species were investigated for antibacterial, anti-fungal and antiviral activities. The extracts of J. curcas, J. gaumeri,J. gossypiifolia, J. multifida, J. nana and J. unicostata were reportedto possess growth inhibition of Gram positive and negative bacte-ria. Mothana et al. (2006) demonstrated the antiviral actions of J.unicostata toward influenza type A and herpes simplex type 1

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Fig. 3. Diterpenoids isolated from Jatropha species.

14 C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29

virus. Phorbol esters extracted from the seed of J. curcas wereinhibited S. pyrogenes, Proteus mirabilis, Pseudomonas putida,Fusarium sp., A. niger and Curvularia lunata with a minimuminhibitory concentration (MIC) of 2.15 � 101, 2.15 � 101,2.51 � 101, 5.8 � 102, 7.0 � 102 and 7.0 � 102 lg/l, respectively(Devappa et al., 2012). Some compounds listed in Tables 3–5explained and proved the antimicrobial actions of these Jatrophaextracts. Two cyclic peptides (3, 11), eleven diterpenes (36–37,46–47, 53, 62–63, 67, 71–73) and miscellaneous compounds(80, 81, 116, 124, 128, 133–135) were proven to have antimicro-bial actions against some bacteria and fungi and their structuresare displayed in Figs. 1 and 3.

In addition to the compounds listed in Tables 3–5, proteins fromJatropha plants also displayed microbial inhibition effects in whichcurcin from the seed oil of J. curcas has the potential of being a bio-logical bacteriocide and pesticide. It was found to inhibit hyphalgrowth and spore formation in bacteria Pyriclarim oryzae, P. funereaand Sclerotinia sclerotiorum at 5 lg/ml (Stirpe et al., 1976).b-glucanase extracted from the same plant exhibited in vitroantifungal activity against Rhizoctonia solani (IC50 = 12.6 nM) andGibberelle zeae by hydrolyzing the cell walls of these fungi (Weiet al., 2005). In addition to the proteins, pure tannic acid and quer-cetin isolated from J. nana also showed promising antimicrobialactivity. In conclusion, Jatropha plants showed a broad spectrumof antibacterial activity and could be a potential source of new

classes of antibiotics useful for infectious disease control (Bhagatand Kurkani, 2010).

4.4. Antiprotozoal activity

Antiprotozoal activities due to malaria, leishmanicidal andtrypanocidal have been attributed to Jatropha species. Extractsof J. gossypiifolia and J. grossidentata demonstrated antiprotozoalactions against parasites P. falciparum, L. amazonensis and T. cruziand these activities are related to the cyclic peptides (2, 4, 13,14, 17–19) and diterpenes (28, 30, 58, 69, 76–77) isolated fromthese plants. 58 and 69 showed the strongest protozoalinhibitions. All of the mentioned compounds are described inTable 7.

4.5. Anticoagulant activity

The suitability of the leaf extract of J. gossypiifolia as an antico-agulant for biochemical and haematological analyses was deter-mined and found to be the highest at a concentration of 1.0 mlper ml of the blood. Not only can J. gossypiifolia extract be usedfor haematological investigations, but its active chemicals mustbe isolated and purified for further biochemical analysis (Oduolaet al., 2005a). The mechanism of action as a haemostatic agentwas found to be by precipitation of coagulant factors (Oduola

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Fig. 3. (continued)

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Fig. 3. (continued)

16 C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29

et al., 2005b). The safety of its use was investigated in differentgroups of albino rats using different doses of its latex. The use ofthe stem latex of J. gossypiifolia as a haemostatic agent is safe sinceit showed no adverse effects on the functions of the liver, kidneyand bone marrow (Oduola et al., 2007).

4.6. Immunomodulating activity

Immunomodulating activity from Jatropha plants was displayedby the cyclic peptides isolated from the latex. Cyclic peptides 1, 11and 12 showed inhibition of the classical pathway of human com-plement activation in vitro (Van den Berg et al., 1995a; Kosasi et al.,1989a; Labadie, 1993). Both 11 and 12 bound to aggregated andantigen-bound IgG, mostly blocked the antibody Clq acceptor site,which is restricted to IgG subclass IgGl (Kosasi et al., 1989a; Laba-die, 1993).

4.7. Anti-inflammatory activity

Carrageenan-induced paw edema in rats is reduced by the anti-inflammatory action of the extracts of J. curcas and J. gossypifolia.The anti-inflammatory activity of J. curcas was derived from themethanol extract of its roots (Mujumdar and Misar, 2004) whilethe methanol and petroleum ether extracts of dried aerial partsof J. gossypifolia showed this activity (Panda et al., 2009a). Mothana

(2011) reported that the extract from J. unicostata reduced abdom-inal constriction induced by acetic acid.

Curcain, a protein from the seed oil of J. curcas was reported toexhibit wound-healing property when tested on mice at two differ-ent enzyme concentrations. Curcain powder at 0.5% and 1.0%(w/w) were mixed with washable ointment base and wound-heal-ing activity by the curcain ointments was compared to the controlsnitrofurazone (0.2% w/w) and propamidine isoethionate (0.15%)(Nath and Dutta, 1991).

4.8. Antioxidant activity

Antioxidant activity of Jatropha plants was shown by J. gaumeri,J. macrantha and J. unicostata assayed using DPPH radical and b-carotene. Mothana (2011) investigated the methanol extract of J.unicostata and it showed a total antioxidant activity of 43.8%.Desmarchelier et al. (1997) reported the antioxidant activity ofthe methanol and dichloromethane extracts of J. macrantha rootsby the quenching of luminal-enhanced chemiluminance. Similarly,the methanol extract of the leaves of J. gaumeri showed promisingactivity (Sãnchez-Medina et al., 2001).

4.9. Molluscicidal activity

Molluscicidal activity of Jatropha plants was reported from J.curcas and J. glandulifera. Liu et al. (1997) investigated the

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Table 5Miscellaneous compounds from Jatropha species.

Type Structurenumber

Compound name Jatrophaspecies

Part References

Pyrrolidine 85 5-Hydroxypyrrolidine-2-one J. curcas Leaf Staubmann et al. (1999a,b)Imidazole 86 4-Butyl-2-chloro-5-formyl-1H-imidazole J. curcas Root Das et al., 2005Pyridine 87 4-Phenyl-2,6-dimethyl-3,5-

pyridinecarboxylateJ. elliptica Rhizome Da Silva et al. (2005)

Pyrimidine 88 Uracil J. curcas Leaf Staubmann et al. (1999a,b)Diamide 89 Curcamide J. curcas Seed cake Yao et al. (2012)Monoterpene 90 1,4-Epoxy-p-methan-2-ol J. gossypiifolia Rhizome Pertino et al. (2007a–c)Sesquiterpene 91 4-Patchoulen-15-oic acid J. gossypiifolia Rhizome Pertino et al. (2007a–c)Sesquiterpene-coumarin

conjugate92 Jatrophadioxan J. integerrima Root Sutthivaiyakit et al. (2009)

Triterpene 93 3-O-acetylaleuritolate acid J. elliptica Root Goulart et al. (1993)J. gossypiifolia Rhizome Pertino et al. (2007c)J. podagrica Root Ee et al. (2005)J. weddeliana Root Brum et al. (1998)

94 a-Amyrin J. gaumeri Leaf Can-Aké et al. (2004)95 b-Amyrin J. gaumeri Leaf Can-Aké et al. (2004)

J. curcas Stem Mitra et al. (1970)96 b-Sitosterol J. curcas Stem, root Mitra et al. (1970), Ling-yi et al.

(1996)J. weddeliana Root Brum et al. (1998)J. gaumeri Leaf Can-Aké et al. (2004)

97 Stigmasterol J. curcas Root Ling-yi et al. (1996)J. elliptica Root Goulart et al. (1993)

98 c-Sitosterol J. podagrica Stem; root Ee et al. (2005)99 Daucasterol J. curcas Root Ling-yi et al. (1996)100 5a-Stigmastane-3,6-dione J. curcas Root Ling-yi et al. (1996)101 Taraxasterol J. curcas Stem Mitra et al. (1970)

J. gaumeri Leaf Can-Aké et al. (2004)Flavonoid 102 Nobiletin J. curcas Root Ling-yi et al. (1996)

103 Tomentin J. curcas Aerial Ravindranath et al. (2004a)104 Vitexin J. gossypiifolia Leaf Subramanian et al. (1971)105 Isovitexin J. gossypiifolia Leaf Subramanian et al. (1971)106 Apigenin J. gossypiifolia Leaf Subramanian et al. (1971)107 Luteolin J. unicostata Leaf Franke et al. (2004)108 Catechin J. macrantha Stem Benavides et al. (2006)

J. gossypifollia Stem109 Catechin-7-O-b-glucopyranoside J. macrantha Stem Benavides et al. (2006)110 Epigallocatechin J. macrantha Stem Benavides et al. (2006)111 Proanthocyanidin J. macrantha Stem Benavides et al. (2006)

Lignan 112 Jatrophan J. gossypifollia Stem Chatterjee et al. (1981)113 Gadain J. gossypifollia Stem Banerji et al. (1984)114 Prasanthaline J. gossypifollia Stem Chatterjee (1988)115 Arylnapthalene J. gossypifolia Stem Das and Banerji (1988)116 Gossypifan J. gossypifollia Aerial Das and Das (1995)117 Jatrodien J. gossypifollia Stem Das et al. (1996)118 Gossypiline J. gossypifollia Das and Kashinatham (1998)119 Gossypidien J. gossypifollia Stem Das and Anjani (1999)120 Isogadain J. gossypifollia Stem Das et al. (1996)

Neolignan 121 Isoamericanin J. curcas Seed cake Yao et al. (2012)122 Isoprincepin J. curcas Seed cake Yao et al. (2012)

Coumarin 123 5-Hydroxy-6,7-dimethoxycoumarin J. curcas Root Ling-yi et al. (1996)124 Scopaletin J. curcas Aerial Ravindranath et al. (2004a)125 Fraxetin J. elliptica Root Goulart et al. (1993)

J. glandulifera Root Parthasarathy and Saradhia (1984)J. unicostata Leaf Franke et al. (2004)J. weddelliana Root Brum et al. (2001)

126 Fraxidin J. podagrica Root Aiyelaagbe and Gloer (2008)127 Marmesin J. curcas Root Naengchomnong et al. (1994)

Coumarino-lignoids 128 Propacin J. curcas Root Naengchomnong et al. (1994)J. gossypiifolia Whole

plantDas and Venkataiah (2001)

J. glandulifera Root Parthasarathy and Saradhia (1984)129 Jatrophin J. curcas Root Naengchomnong et al. (1994)130 Cleomiscosin A J. gossypiifolia Stem Das et al. (2003)

J. multifida Stem Das et al. (2009b)Non-cyanogenic glucoside 131 Multifidin A J. multifida Latex Van den Berg et al. (1995b)Glucoside 132 b-Ethyl-D-glucopyranose J. curcas Seed cake Yao et al. (2012)Phloroglucinol 133 Multifidol J. multifida Latex Kosasi et al. (1989b)

134 Multifidol glucoside J. multifida Latex Kosasi et al. (1989b)Fatty acid 135 Glyceride-1,2S-tetracosanoate acid J. curcas Root Ling-yi et al. (1996)

136 12-Hydroxyoctadec-cis-9-enoic acid J. gossypifolia Seed oil Hosamami and Katagi (2008)137 Japodic acid J. podagrica Root Aiyelaagbe and Gloer (2008)138 Glycerol monooleate J. curcas Seed cake Yao et al. (2012)

(continued on next page)

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Table 5 (continued)

Type Structurenumber

Compound name Jatrophaspecies

Part References

Ester ferulate 139 n-Heptyl ferulate J. podagrica Stem, root Ee et al. (2005)140 Pentatriacontanyl ferulate J. elliptica Root Goulart et al. (1993)141 Tetradecyl-(E)-ferulate J. curcas Aerial Ravindranath et al. (2004a)142 Erythrinasinate J. podagrica Root Aiyelaagbe and Gloer (2008)

Phenolic 143 3-Hydroxy-4-methoxybenzaldehyde J. curcas Root Ling-yi et al. (1996)144 3-Methoxy-4-hydroxybenzoate acid J. curcas Root Ling-yi et al. (1996)145 Caffeoylaldehyde J. curcas Seed cake Yao et al. (2012)146 Syringaldehyde J. curcas Seed cake Yao et al. (2012)

Anthraquinone 147 2-Methylanthraquinone J. curcas Aerial Ravindranath et al. (2004a)Deoxypreussomerin 148 Palmarumycin JC1 J. curcas Stem Ravindranath et al. (2004a)

149 Palmarumycin JC2 J. curcas Stem Ravindranath et al. (2004a)150 Palmarumycin CP1 J. curcas Stem Ravindranath et al. (2004a)

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molluscicidal activity against Biomphalaria glabrata, Bulinus globo-sus and Oncomelania hupensis of J. curcas extracts which are knownto contain phorbol esters. Al-Zanbagi et al. (2000) investigatedfresh and dry leaf extracts of J. glandulifera towards B. pfeifferiand discovered the methanol extract of the fresh leaves demon-strated an LD50 of 21.7 ppm and LD90 of 29.8 ppm while the ace-tone extract of the fresh leaves demonstrated an LD50 of6.76 ppm and LD90 of 12.5 ppm. On the other hand, the cold water,methanol, chloroform, acetone and hexane extracts of dry leaves ofthe plant showed an LD50 of 73.3, 84.9, 16.5, 102.6, 96.0 ppm andLD90 of 118.8, 160.7, 46.8, 129.0, 118.0 ppm, respectively. The ace-tone extract of the fresh leaves and the chloroform extract of dryleaves of J. glandulifera exhibited the best molluscicidal activity(Al-Zanbagi et al., 2000). The compounds isolated from Jatrophaplants that showed this activity are 33–35 and 64 and displayedin Table 7 and Fig. 3.

4.10. Protoscolicidal activity

Protoscolicidal action of Jatropha plants was reported from J.curcas and J. unicostata. The antihelminthic action of J. curcaswas reported from its leaf against Pheretima poshtuma (Ahirraoet al., 2009). Barzinji et al. (2009) investigated the aqueous andmethanolic extracts of J. unicostata on the viability of Echinococcusgranulosus protoscoleces in vitro where a concentration of1.0 � 103 lg/ml exhibited the highest protoscolicidal activity. Fur-thermore, oral and intraperitoneal administration of its extractsto white mice invoked noticeable inhibitory effects on thein vivo development of secondary hydatid cysts compared toalbendazole sulfoxide, which is commonly used in the treatmentfor hydatidosis.

4.11. Insecticidal activity

Insecticidal activity of Jatropha plants was demonstrated by J.curcas and J. gossypiifolia. The extract of J. gossypiifolia leaf sug-gested to have compounds that are toxic to insects was testedagainst the larvae of three lepidopteran species, Busseola fusca,Ostrinia nubilalis and Sesamia nonagrioides. These lepidopteransare important pests of maize in Africa, Europe and Mediterraneancountries (Valencia et al., 2006). Insecticidal activities of J. curcasoil containing phorbol esters have been reported against Aphisgossypii, B. fusca, Blattella germanica, Callosobruchus chinensis, Cu-lex sp., Empoasca biguttula, Helicoverpa armigera, Manduca sexta,Oncopeltus fasciatus, Pectinophora gossypiella, Oncopeltus fasciatus,Phthorimaea operculella, Sesamia calamistis and Sitophilus zeamais(Wink et al., 1997). Boateng and Kusi (2008) found that the seedoil of J. curcas was also toxic against Callosobruchus maculatus and

its parasite, Dinarmus basalis. Table 7 showed two compounds,112 and 137 from Jatropha plants which displayed insecticidalactivity.

4.12. Inhibition of AChE

Inhibition of acetylcholinesterase (AChE) was reported from J.gossypiifolia. The aqueous solutions of the leaf and stem bark of J.gossypiifolia were found to be active in killing fish. The toxic ef-fect of the stem bark of the plant was time as well as dosedependent. Significant negative correlation between LC50 andexposure periods was also derived. The LC50 values of the stembark extract of J. gossypiifolia were found to decrease from4.61 � 106lg/l (24 h) to 4.34 � 106lg/l (96 h). It was suggestedthat the plant cannot be used directly in freshwater bodies, with-out detailed studies on the long-term effects on non-targetorganisms and their structure–activity relationship (Singh andSingh, 2002a). Significant alteration in total proteins, total freeamino acids, nucleic acids, glycogen, pyruvate, lactate levelsand protease activity in different tissues (muscle, liver and gona-dal) of Channa punctatus were shown by aqueous latex extracts ofJ. gossypiifolia after 96 h of exposure to 40% and 80% of LC50

(24 h). The changes in all levels of glycogen, pyruvate, lactateand nucleic acids, but almost complete recovery in total proteins,total free amino acids level and protease activity in all the threetissues of the fish after the 7th day of the withdrawal of treat-ment, supported the view that the plant products are safer tobe used as pesticides for control of common weed in culture fishponds (Singh and Singh, 2002b). The latex of J. gossypiifolia whichwas obtained by cutting the stem into pieces and draining theminto a glass tube was lyophilised and the powder was used forbiochemical experiment. The latex caused a significant reductionin acid/alkaline phosphatase and anti-acetylcholinesterase activi-ties in the nervous tissue of freshwater air breathing fish Channamarulius and the reduction was depended on time and dose(Singh and Singh, 2005).

4.13. Toxicity

Lioglier (1990) reported that the seeds of Jatropha species arehighly toxic and advised against their usage in herbal medicine.The toxic element in the seed is a toxalbumin named jatrophinwhich causes agglutination and haemolysis of red cells and alsoinjurious to other cells (Lucas and De Silva, 2006). The toxicologicaleffects of J. curcas oil in rats reported an acute oral LD50 of the oil tobe 6 ml/kg body weight. The oil was reported to cause toxicologicalmanifestations like diarrhoea and gastrointestinal inflammationand produced irritation followed by skin necrosis. The toxic

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Fig. 4. Miscellaneous compounds isolated from Jatropha species.

C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29 19

fraction of the oil was found to have a haemolytic action at 25l and100 lg/ml of saline brine shrimp (Gandi et al., 1995). Carp (Cypri-nus carpio) was discovered to be highly susceptible to phorbol es-ters and gave antagonism effects at 15 ppm (15 lg/g) in its diet. Alevel higher than 31 lg/g of extract in the diet lowered its averagemetabolic rate, increased fecal mucus production and rejection offeed (Becker and Makkar, 1998). Furthermore, Mongkolvisut

et al. (2006) reported that the latex of J. integerrima was knownto be toxic and its leaf can cause squeamish, stomachalgia andhas a strong purgative effect. Levin et al. (2000) reported an inci-dent of two unrelated healthy boys (9.5 and 8.5 years of age)who experienced intractable vomiting, colicky abdominal painand watery diarrhoea after one hour of ingesting probably morethan ten seeds of J. multifida each. Another case was reported from

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Fig. 4. (continued)

20 C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29

Sri Lanka whereby a child spontaneously vomited several timesand became drowsy after ingesting the seeds of the ‘‘Kapum Kir-iya’’ (J. multifida) plant which was growing near a fence (Gurugeet al., 2007). b-Glucanase, a protein from the seed oil of J. curcaswas reported to be toxic to mice with an LD50 of 2.22 g/kg (Wei

et al., 2005). Devappa et al., 2010a,b in their review concluded thata number of Jatropha species have a mixture of toxic and antinutri-tional compounds. They were also suggested that phorbol estersand curcin are significant toxic compounds contain in organic sol-vent extracts and aqueous extracts, respectively.

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Fig. 4. (continued)

C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29 21

5. Conclusion

Jatropha species have been used as traditional medicine in manycountries. J. curcas, J. gossypiifolia and J. multifida are three speciesout of 14 species reported in this review that are mostly employedas traditional medicines analogous to their phytochemicals andpharmacological reports. Investigations of the latex of J. curcas, J.chevalieri, J. gossypiifolia, J. integerrima, J. multifida, J. podagricaand J. pohliana have resulted in the isolation of new alkaloidal

cyclic peptides possessing cytotoxic, antimalarial and antimicro-bial activities. Investigations of the roots and stems of J. curcas, J.elliptica, J. gaumeri, J. gossypiifolia, J. grossidentata, J. integerrima, J.multifida, J. podagrica and J. weddelliana found many diterpenoidswith promising anticancer, cytotoxic, antitumor, antimalarial,antileishmanial, antimicrobial, insecticidal and molluscicidal activ-ities. Rhamnafolane and lathyrane were the two major diterpe-noids occurred in most Jatropha species. Our review reveals thatspecies from genus Jatropha possess strong potential as sources

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Table 6Biological activity of extracts of Jatropha species.

Species Biological activity Description References

J. curcas Anti-metastatic Simultaneous administration of the methanolic fraction at doses 100 and200 mg/kg, p.o significantly inhibited the metastatic colony formation ofthe melanoma in lungs by 47.54 and 69.52%, respectively, with increase inthe survival rate of the metastatic tumor bearing animals, as compared tothe untreated animal

Balaji et al. (2009)Antiproliferative

Antibacterial The crude ethanolic, methanolic and water extracts of the stem barkinhibited the growth of Staphylococcus aureus, S. epidermidis, Pseudomonasaeruginosa, Escherichia coli, Streptococcus faecalis, Shigella dysentriae,Micrococcus kristinae, Klebsiella pneumonia, Bacillus cereus, B. subtilis, Proteusvulgaris and Serratia marcescens

Igbinosa et al. (2009)

Anticoagulant The latex significantly reduce the clotting time of human blood. The blooddiluted with latex did not clot at all even at high dilutions and prolongedclotting time

Osoniyi and Onajobi (2003)

Anti-inflammatory The methanolic extract of the roots exhibited systemic and significant anti-inflammatory activity in acute carrageenan-induced rat paw edema

Mujumdar and Misar (2004)

Antiulcer The methanolic extract of the leaves assayed on pyrolus ligation andaspirin-induced gastric ulcers in Wistar rats displayed counter-action togastric lesions indicating antiulcer activity

Kannappan et al. (2008)

Insecticidal Seed oil was found to be toxic to Callosobruchus maculates and its parasiteDinarmus basalis

Boateng and Kusi (2008)

Molluscicidal The methanol extract of the seed oil containing phorbol esters inhibited thegrowth of Biomphalaria glabrata, Bulinus globosus and Oncomelania hupensis

Liu et al. (1997)

Plant extract was found to be toxic against snails transmitting Schistosomamansoni, S. japonicum and S. haematobium

Rug and Ruppel (2000)

J. gaumeri Cytotoxic The non-polar extract (dichloromethane) of J. gaumeri roots inhibited NF-kBactivation with IC50 7.8 lg/ml

Ankli et al. (2002)

Antibacterial The crude extract of the plant showed antimicrobial activity against B.subtilis, C. albicans and S. cerevisiae with inhibition zone of 14, 7 and 6 mm,respectively

Sãnchez-Medina et al. (2001)

Gastrointestinal disorder The non-polar extract of roots showed activity against Heliobacteriumpylori at MIC of 5 lg/ml. It was also found to be the most active plant testedagainst B. cereus

Ankli et al. (2002)

Antioxidant The methanolic extract of the leaves showed significant antioxidant activityin the reduction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and inhibition ofthe bleaching of beta-carotene assay

Sãnchez-Medina et al. (2001)

J. glandulifera Molluscicidal The fresh and dry leaves showed inhibition against snail B. pfeifferi Al-Zanbagi et al. (2000)

J. gossypiifolia Cytotoxic The alcoholic extract of the roots of J. gossypiifolia showed significantinhibitory activity in vitro against cancer cells derived from humancarcinoma of the nasopharynx and in vivo against four standards of animaltumor systems

Kupchan et al. (1970)

Antibacterial The dichloromethane-methanol (1:1) extract of J. gossypiifolia showedactivity against B. subtilis, B. cereus, B. pumilis, Bordetella bronchiseptica,Micrococcus luteus, S. aureus, S. epidermidis, E. coli, K. pneumonia, P.aeruginosa, S. faecalis, Candida albicans, Aspergillus niger and Saccharomycescerevisiae

Rajani et al. (2006)

The methanolic and chloroform extracts of the leaves showed activityagainst S. typhi, S. aureus, P. aeroginosa and C. albicans

Ogundare (2007)

Antiprotozoal Antiprotozoall activity of CH2Cl2 extract of the leaves against Plasmodiumfalciparum showed an IC50 of 35.66 ± 2.86 lg/ml

Jansen et al. (2010)

Crude hot water extract of the leaves showed 100% inhibition against P.falciparum

Gbeassor et al. (1989)

Anticoagulant Effect of the leaf extract was found to be highest at a concentration of 1.0 mlper ml of the blood

Oduola et al. (2005a)

Anti-inflammatory Oral administration of the methanolic and petroleum ether extracts of driedaerial parts at doses of 100 and 200 mg/kg/day of body weight to healthyanimal reduced the carrageenan-induced paw edema in rats. Themethanolic extract exhibited significant activity than petroleum etherextract in the treatment of pain and inflammatory

Panda et al. (2009a)

Hepatoprotective Potential hepatoprotective action against carbon tetrachloride inducedhepatic damage in rats. The petroleum ether extract was shown to possessmaximum protectivity and methanolic extract showed the minimumactivity

Panda et al. (2009b)

Insecticidal Leaf extract is toxic to three lepidopteran species, Busseola fusca(Noctuidae), Ostrinia nubilalis (Pyralidae) and Sesamia nonagrioides(Noctuidae)

Valencia et al. (2006)

Inhibition AChE Aqueous solutions of the leaf and stem bark were active in killing fishes.The toxic effect of stem bark extract was time as well as dose-dependent

Singh and Singh (2002a)

J. grossidentata Antiplasmodial The petroleum ether and ethyl acetate extracts of the roots showed in vitroactivity against Trypanosoma cruzi and Leishmania strains at 10 lg/ml

Schmeda-Hirschmann et al. (1996)

J. macrantha Antitumor The methanolic and chloroform extracts of the roots were active againstArtemia salina with ED50 667.0 lg/ml and 149.0 lg/ml, respectively. In vitrotest for DNA binding effect of methanolic extract of the roots at dosage

Desmarchelier et al. (1996a,b)

22 C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29

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Table 6 (continued)

Species Biological activity Description References

1.0 � 103 lg/ml was inactiveToxicity The aqueous extract of the leaves on brine shrimp (Artemia sp.) had LC50 of

430 lg/ml, while the alcoholic extract (ethanol) showed toxicity with LC50

of 93 lg/ml

Bussmann et al. (2011)

Hormone enhancement Extracts of the branch and sap significantly increased testosterone levelsover controls at dosage 5 g/100 ml in mice

Oshima et al. (2003)

Antioxidant MeOH and dichloromethane extracts of the roots measured by quenching ofluminal-enchanced chemiluminescence showed antioxidant activity atdosage of IC50 1.542 � 105 lg/ml and 7.37 � 104 lg/ml, respectively

Desmarchelier et al. (1997)

J. multifida Antibacterial The hexane, ethyl acetate, chloroform and methanol extracts of the roots ofJ. multifida yellow rootbark, red rootbark and rootwood effectively inhibitedthe growth of B. subtilis and S. aures at concentration of 200 lg/disk. Onlyextracts from rootwood showed activity against E. coli. All extracts were notactive against C. albicans

Aiyelaagbe (2000)

Wound healing The leaf exudates afforded acceleration of wound healing process oninjuries made in rats which displayed maturing in that area

Buch et al. (2008)

J. nana Antibacterial Seven extracts of the seeds, leaves and roots of J. nana inhibited the growthof B. cereus, S. aureus, E. coli, Enterococcus fecalis, P. aeruginosa, K. neumoniaand S. dysentrae. The ethanolic and methanolic extracts showed mostpotent activity against seven microorganisms mentioned

Bhagat and Kurkani (2010)

J. unicostata Antibacterial The chloroform extract of the leaves and fruits showed antimicrobialactivity against S. aureus, B. cereus and M. flavus with inhibition zone of 10, 8and 8 mm, respectively. Meanwhile the methanol extract showedinhibition zone of 18, 10, 15, 18 and 18 mm against S. aureus, B. cereus, M.flavus, S. epidermis and S. haemolyticus, respectivelyThe chloroform extract of the barks showed inhibition against S. aureus, B.cereus, M. flavus, S. epidermis and S. haemolyticus with inhibition zones of 11,10, 11, 10, 8 and 10 mm, respectively. The methanol extract of the barkswas found to be potent toward the tested microorganisms, but noinhibition against S. haemolyticus

Mothana and Lindequist (2005)

Antiviral The methanolic extract of the plant demonstrated a marked antiviral effectagainst Influenza virus type A and Herpes simplex type 1

Mothana et al. (2006)

Anti-inflammatory Extract of J. unicostata at 400 mg/kg depleted the paw edema considerably(53.57%) and the weight of cotton pellet granuloma (32.62%). Futhermore, italso diminished the abdominal constriction induced by acetic acid with a41.50% inhibition

Mothana (2011)

Antioxidant The methanolic extract of the plant assayed in vitro by DPPH radical and b-carotene-linoleic acid displayed total antioxidant activity of 43.8%

Mothana (2011)

Protoscolicidal The aqueous and methanolic extracts of the plant at concentrations of1.0 � 103 lg/ml displayed protoscolicidal on viability of Echinococcusgranulosus

Barzinji et al. (2009)

Table 7Biological activity of compounds isolated from Jatropha species.

Structurenumber

Compound Biological activity Description References

1 Curcacycline A Immunomodulator Displayed inhibition of classical pathway activity of humancomplement and proliferation of human T-cells

Van den Berg et al. (1995a)

2 Curcacycline B Antimalarial Inhibition against P. falciparum with IC50 value of 10 lM Auvin-Guette et al. (1997a)Enhance rotamase Enhanced peptidyl-prolyl cis–trans isomerase (Pplase) activity by

60% at lM based on a-chymortrypsin rotamase coupled enzymaticexperiment using human cyclophillin B, whereas no modification ofcyclophilin B activity was observed in the presence of 1

Auvin-Guette et al. (1997a)

3 Jatrophidin Antifungal Weak antifungal effect against C. albicans, C. krusei, C. parapsilosis andCryptococcus neoformans

Altei et al. (2007)

AchE inhibitor Acetylcholinesterase inhibitor Altei et al. (2007)4 Chevalierin A Antimalarial Inhibition against P. falciparum with IC50 8.9 lM Baraguey et al. (1998)9 Integerrimides A Cytotoxicity Inhibited to a certain degree cell proliferation of human ICP-298

melanoma cells, as well as cell, migration of human Capan IIpancreatic carcinoma cells at 50 lM

Mongkolvisut et al. (2006)

Antifungal Inactive Mongkolvisut et al. (2006)Antiviral Inactive against HSV-1 Mongkolvisut et al. (2006)Antimalarial Inactive Mongkolvisut et al. (2006)

10 Integerrimides B Cytotoxicity Inhibited to a certain degree cell proliferation of human ICP-298melanoma cells, as well as cell, migration of human Capan IIpancreatic carcinoma cells at 50 lM

Mongkolvisut et al. (2006)

11 Labaditin Antibacterial Inhibitory effect against Gram-positive bacteria, Streptococcusmutans, but no effect against Gram-negative bacteria

Barbosa et al. (2010)

Antifungal Inactive Mongkolvisut et al. (2006)Antiviral Inactive against HSV-1 Mongkolvisut et al. (2006)

(continued on next page)

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Table 7 (continued)

Structurenumber

Compound Biological activity Description References

Antimalarial Inactive Mongkolvisut et al. (2006)Immunomodulator Selectively inhibited the classical pathway of human complement

activation in vitro. It binds to aggregated and antigen-bound IgG,mostly block the antibody Clq acceptor site, which is restricted toIgG subclass IgGl

Kosasi et al. (1989a), Labadie(1993)

12 Biobollein Immunomodulator Inhibited the classical pathway of human complement activation.Binds to aggregated and antigen-bound IgG, mostly block theantibody Clq acceptor site, which is restricted to IgG subclass IgGl

Kosasi et al. (1989a), Labadie(1993)

13 Mahafacyclin A Antimalarial Inhibited P. falciparum wih IC50 values of 16 lM Baraguey et al. (2000, 2001)14 Mahafacyclin B Antimalarial Inhibited P. falciparum wih IC50 values of 2.2 lM Baraguey et al. (2000, 2001)16 Podacycline B Cytotoxicity Cytotoxic against Dalton’s lymphoma ascites (DLA) and Ehrlich’s

ascites carcinoma (EAC) cell lines with IC50 values of 13.2 and15.5 lM, respectively

Dahiya (2008)

Antihelminthic At a dose of 2 � 103 lg/ml inhibited earthworms Megascoplexkonkanensis, Pontoscotex corethruses and Eudrilus sp.

Dahiya (2008)

17 Pohlianin A Antimalarial Inhibited P. falciparum with IC50 values of 57 lM Auvin-Guette et al. (1999)18 Pohlianin B Antimalarial Inhibited P. falciparum with IC50 values of 25 lM Auvin-Guette et al. (1999)19 Pohlianin C Antimalarial Inhibited P. falciparum with IC50 values of 16 lM Auvin-Guette et al. (1999)20 DHPB Tumor promoter Induced ornithine decarboxylase in mouse skin (2.8 nmol CO2/

30 min/mg protein/34 nmol application), inhibited the specificbinding of [3H]-12-O-tetradecanoylphorbol-13-acetate to phorbolester receptors (50% effective dose, 17.0 nM) and activated proteinkinase C in vitro (50% effecive dose, 36.0 nM)

Hirota et al. (1988)

27 Jatropherol I Molluscicidal Toxic to third instars silkworm, Bombyx mori larvae after ingestionwith LC50 values 5.793, 2.197 and 1.578 (� 103) lg/ml at 48, 72 and120 h, respectively

Jing et al. (2005)

28 Jatropholone A Cytotoxicity Antiproliferative activity against five fibroblasts CCL-171, AGS CRL-1739, lung HTB-58, bladder HTB-1 and leukemia CCL-240 at>100 lM

Theoduloz et al. (2009)

A selective effect against AGS cells with IC50 of 49 lM and non-toxicto fibroblasts (>1000 lM)

Pertino et al. (2007b,c)

Non-cytotoxic to African green monkey kidney fibroblasts Sutthivaiyakit et al. (2009)Antimalarial Inhibited P. falciparum with IC50 of 5.4 lg/ml Sutthivaiyakit et al. (2009)Gastroprotective Displayed gastroprotective activity in the HCl/EtOH-induced gastric

lesions model in mice. Exhibited a dose-related response withmaximum effect of 54% lesion reduction at the maximum dose(1 � 105 lg/kg

Pertino et al. (2007b,c)

Molluscicidal A mixture of 34 and 35 has molluscicidal effect against the snail B.glabrata with LC50 of 58.04 ppm

Dos Santos and Sant’Ana(1999)

29 Jatropholone B Cytotoxicity Antiproliferative activity against five fibroblasts CCL-171, AGS CRL-1739, lung HTB-58, bladder HTB-1 and leukemia CCL-240 at 0.29,0.51, 1.8, 1.7 and 5.1 lM, respectively

Theoduloz et al. (2009)

Non-cytotoxic to both AGS cells and fibroblasts (>1000 lM) Pertino et al. (2007b,c)Non-cytotoxic to African green monkey kidney fibroblasts Sutthivaiyakit et al. (2009)

Gastroprotective Gastroprotective activity in the HCl/EtOH-induced gastric lesionsmodel in mice was displayed a strong action at all doses, reducinglesions by 83–91%

Pertino et al. (2007b,c)

Molluscicidal A mixture of 34 and 35 has molluscicidal effect against the snail B.glabrata with LC50 of 58.04 ppm

Dos Santos and Sant’Ana(1999)

30 2a-Hydroxyjatropholone Cytotoxicity Non-cytotoxic to African green monkey kidney fibroblasts Sutthivaiyakit et al. (2009)Antimalarial Inhibition activity against P. falciparum with IC50 of 4.1 lg/ml Sutthivaiyakit et al. (2009)

31 2b-Hydroxyjatropholone Cytotoxicity Cytotoxic against African green monkey kidney fibroblasts with IC50

of 49.4 lg/mlSutthivaiyakit et al. (2009)

33 Jatrophalactam Cytotoxicity No significant inhibitory activity in vitro against three human cancercell lines, human lung cancer (A549), human colon cancer (HT-29)and human epidermal squamous cell carcinoma (A431)

Wang et al. (2009)

35 Curcusone B Cytotoxicity Displayed metastatic processes at doses that non-toxic to cells,effectively, which may be of therapeutic benefit for the treatment ofmetastatic cancers

Muangman et al. (2005)

36 Curcusone C Antibacterial andantifungal

Inhibition effect against B. subtilis, Botrytis cinerea and Rhizoctoniasolani even at low doses of 50 lg

Achenbach and Benirschke(1997), Thippornworng andTohtong (2006)

37 Curcusone D Antibacterial andantifungal

Inhibition effect against B. subtilis, Botrytis cinerea and R. solani evenat low doses of 50 lg

Achenbach and Benirschke(1997), Thippornworng andTohtong (2006)

46 (4Z)-Jatrogrossidentadione Antibacterial Inhibition effect against B. subtilis and S. aureus with zone of 20 and10 mm, respectively

Aiyelaagbe et al. (2007),Schmeda-Hirschmann et al.(1992)

47 15-epi-(4Z)-Jatrogrossidentadione

Antibacterial Inhibition effect against B. subtilis and S. aureus with zone of 17 and9 mm, respectively

Aiyelaagbe et al. (2007),Schmeda-Hirschmann et al.(1992)

48 Falodone Anticancer Inhibition growth of A-549 cell at IC50 of 120 lg/ml Falodun et al. (2012)50 Multifidone Cytotoxicity In vitro against human acute monocytic leukemia (THP-1), human

promyelocytic leukemia (HL-60), human lung carcinoma (A-549)Das et al. (2009b)

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Table 7 (continued)

Structurenumber

Compound Biological activity Description References

and human malignant melanoma (A-375) with IC50 of 45.6, 120.7,127.12 and 159.0 lM, respectively

52 Multifidanol Cytotoxicity In vitro cytotoxicity against A-549, Neuro-2a, HeLa, MDA-231 andMCF-7 cell lines with IC50 6.27, 6.35, 15.4, 7.04 and 6.39%,respectively

Kanth et al. (2011)

Antibacterial Inhibition effect against B. subtilis and E. coli with MIC of 4.68 lg/ml. Kanth et al. (2011)53 Multifidenol Cytotoxicity In vitro cytotoxicity against A-549, Neuro-2a, HeLa, MDA-231 and

MCF-7 cell lines with IC50 12.5, 5.6, 7.56, 5.39 and 8.57%, respectivelyKanth et al. (2011)

Antibacterial Inhibition effect against S. aureus with MIC of 4.68 lg/ml. Kanth et al. (2011)56 Japodagrin Antibacterial Inhibition effect against B. subtilis and S. aureus at 20 lg/disk with

inhibition zones of 16 and 12 mmAiyelaagbe et al. (2007)

57 Japodagrol Cytotoxicity Inhibitory activity in vitro against P-388 lymphocytic leukemia andKB carcinoma cell cultures with ED50 of 2.5 and 5.6 lg/ml,respectively

Sanni et al. (1988)

58 Jatrophone Cytotoxicity Antileukemic activity against P-388 lymphocytic leukemia at 2.7 and1.2 (� 104)lg/kg cytotoxicity (ED50) against KB cell culture at0.17 lg/ml

Goel et al. (2007)

In vitro against the P-388 lymphocytic leukemia and Eagle’scarcinoma of the nasopharynx test system with ED50 of 0.01 lg/mland 8.7 � 10�6 lg/ml

Taylor et al. (1983)

Cytotoxic to AGS and lung fibroblast with IC50 2.4 lM and 2.8 lM Pertino et al. (2007a)Anti-proliferative effects against fibroblasts CCL-171, AGS CRL-1739,lung HTB-58, bladder HTB-1, leukemia CCL-240 with IC50 of 0.29,0.51, 1.8, 1.7 and 5.1 lM, respectively

Theoduloz et al. (2009)

Antitumor Reacts with small molecular weight thiols as well as thio groups onproteins such as bovine serum albumin and RNA polymerase fromE. coli, suggested to be responsible for the antitumor activity in vitro

Lillehaug et al. (1973)

Antileishmanial Subcutaneous administration at 2.5 � 103lg/kg/day significantly(p < 0.05) inhibited the virulent strain pH 8 of L. amazonensis butproven to be too toxic under assay conditions

Schmeda-Hirschmann et al.(1996)

Gastroprotective Displayed a strong gastroprotective effect with no significantdifferences between 2.5, 5 or 10 (� 103) lg/kg and reduced lesionsfrom 88 to 93%

Pertino et al. (2007b,c)

Antinoceptive Inhibition effect of [3H]glutamate binding indicated a neurochemicalparameter possibly related to the antinoceptive activity

Martini et al. (2000)

Molluscicidal Inhibition effect against the snail with LC50 of 1.16 ppm Dos Santos and Sant’Ana(1999)

59 Hydroxyjatrophone A Cytotoxicity In vitro inhibition against the P-388 lymphocytic leukemia andEagle’s carcinoma of the nasopharynx test system with ED50 of 0.03and 0.16 lg/ml

Taylor et al. (1983)

60 Hydroxyjatrophone B Cytotoxicity In vitro inhibition against the P-388 lymphocytic leukemia andEagle’s carcinoma of the nasopharynx test system with ED50 of 0.06and 0.07 lg/ml

Taylor et al. (1983)

61 Hydroxyjatrophone C Cytotoxicity In vitro inhibition against the P-388 lymphocytic leukemia andEagle’s carcinoma of the nasopharynx test system with ED50 of 2.2and 0.03 lg/ml

Taylor et al. (1983)

62 9b-Hydroxyisabellione Cytotoxicity Cytotoxic to AGS and lung fibroblast with IC50 53.1 lM and 260 lM Pertino et al. (2007a)Anti-proliferative effects against fibroblasts CCL-171, AGS CRL-1739,lung HTB-58, bladder HTB-1, leukemia CCL-240 with IC50 of 35.9,13.7, 33.3, 20.1 and >100 lM, respectively

Theoduloz et al. (2009)

65 Jatrophenone Antibacterial Inhibitory activity against S. aureus. The activity was comparable tothat of the standard compound, penicillin G

Ravindranath et al. (2003)

66 Japodagrone Antibacterial Inhibition activity against B. subtilis with zone of 12 mm at 20 lg/disc

Aiyelaagbe et al. (2007)

69 Jatrogrossidione Leishmanicidal In vitro inhibition against Leishmania amazonensis with IC100 of0.75 lg/ml

Schmeda-Hirschmann et al.(1996)

Trypanocidal In vitro inhibition against Trypanosoma cruzi with IC100 of 1.5–5.0 lg/ml

Schmeda-Hirschmann et al.(1996)

70 2-epi-Jatrogrossidione Antibacterial Antibacterial activity against Bacillus subtilis Can-Aké et al. (2004)74 2-Hydroxyisojatrogrossidion Antibacterial Inhibition effect against B. subtilis and S. aureus with inhibition zones

of 31 and 21 mm, respectivelyAiyelaagbe et al. (2007),Schmeda-Hirschmann et al.(1992)

75 2-Epihydroxyisojatrogrossidion

Antibacterial Inhibition effect against B. subtilis and S. aureus with inhibition zoneof 35 and 26 mm, respectively

Aiyelaagbe et al. (2007),Schmeda-Hirschmann et al.(1992)

76 Caniojane Cytotoxicity The cytotoxic activity against African green monkey kidneyfibroblasts with IC50 of 12.9 lg/ml

Sutthivaiyakit et al. (2009)

Antituberculosis Inhibitory against Mycobacterium tuberculosis H37Ra with aminimum inhibitory concentration of 25 lg/ml. The reference(kanamycin) was active at 2.5 lg/ml

Sutthivaiyakit et al. (2009)

Antimalarial Inhibition effect against P. falciparum with IC50 3.3 lg/ml Sutthivaiyakit et al. (2009)77 1,11-Bisepicaniojane Antimalarial Inhibition effect against P. falciparum with IC50 7.9 lg/ml Sutthivaiyakit et al. (2009)81 Jatrophalactone Cytoxicity Inhibited the HL-60, SMMC-7721, A-549, MCF-7 and SW480 cell Liu et al. (2012)

(continued on next page)

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Table 7 (continued)

Structurenumber

Compound Biological activity Description References

lines with IC50 of 8.5, 20.6, 19.7, 20.1 and 19.2 lM, respectively86 4-Butyl-2-chloro-5-formyl-

1H-imidazoleAntibacterial Inhibited the Gram-positive organisms, B. subtilis and B. sphaericus,

and weak activity against the Gram-negative organisms,Chromobacterium violaceum and Klebsiella aerogens

Das et al. (2005)

87 Diethyl 4-phenyl-2,6-dimethyl-3,5-pyridinecarboxylate

Antibacterial In vitro antibacterial and resistance-modifying activity againststrains of S. aureus possessing the MsrA and NorA resistance effluxmechanisms. The antibiotic efflux was indicated as an inhibitor ofthe NorA efflux pump and restores the level of intracellular drugconcentration

Marquez et al. (2005)

93 3-O-acetylaleuritolate acid Gastroprotective Gastroprotective effect at the lowest dose, reducing lesions by about50%, with less effect at 5 and 10 (� 103) lg/kg

Pertino et al. (2007b,c)

112 Jatrophan Insecticidal Strong inhibition against the storage grain pest, Tribolium castaneum Chatterjee et al. (1981)126 Fraxidin Antibacterial Antibacterial activity against B. subtilis Aiyelaagbe and Gloer (2008)137 Japodic acid Antibacerial Inactive in the antibacterial assays Aiyelaagbe and Gloer (2008)

Insecticidal Mild insect growth inhibition activity against Helicoverpa zea Aiyelaagbe and Gloer (2008)142 Erythrinasinate Antibacterial Antibacterial activity against B. subtilis Aiyelaagbe and Gloer (2008)143 Palmarumycins JC1 Antibacterial Inhibition effect against S. aureus at 30 lg/ml with zone of 11 mm Ravindranath et al. (2004b)149 Palmarumycins JC2 Antibacterial Inhibition effect against S. aureus at 30 lg/ml with zone of 10 mm Ravindranath et al. (2004b)150 Palmarumycins CP1 Antibacterial Inhibition effect against S. aureus at 30 lg/ml with zone of 13 mm Ravindranath et al. (2004b)

26 C.W. Sabandar et al. / Phytochemistry 85 (2013) 7–29

of new drugs. Due to their various promising activities, furtherstudy should be carried out on the drug development of Jatrophaextracts and constituents.

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Carla W. Sabandar was born in 1985, graduated fromHaluoleo University of Chemistry Department in Indo-nesia, in 2009. After she received her Bachelor of Sciencedegree from Haluoleo University by Dr. Sahidin’sresearch guidance, she moved to Malaysia in 2011 tofurther her study in M.Sc. by research at PharmacyFaculty of Universiti Kebangsaan Malaysia. She is alsoinvolved in natural product research with Assoc. Prof.Dr. Norizan Ahmat from Faculty of Applied Sciences,Universiti Teknologi MARA, Malaysia. Her researchfocuses in the area of isolation of natural products andbiological activities (anti-platelet and anti-inflamma-

tion agent of crude extracts and pure natural products).

Norizan Ahmat is Associate Professor at the Faculty ofApplied Sciences, Universiti Teknologi MARA Malaysia.She obtained her degree in Chemistry from the ArkansasState University, U.S.A in 1989. She received her M.Sc. inChemistry in 1995 and Ph.D in Natural ProductsChemistry from the Universiti Kebangsaan Malaysia in2008. In her current research, she is interested in thechemistry and pharmacology of alkaloids, flavonoidsand resveratrol oligomers from plants in Malaysiaespecially from the family of Annonaceae, Euphorbia-ceae, Dipterocarpaceae and Gnetaceae. Her multidisci-plinary research includes collaborations with

researchers from Indonesia and Japan. She is a member of the GA Society forMedicinal Plants and Natural Product Research.

Faridahanim Mohd Jaafar is a lecturer at the Faculty ofApplied Sciences, Universiti Teknologi MARA Malaysia.She obtained her B.Sc. and M.Sc. in Chemistry fromWestern Illinois University, U.S.A in 1984 and 1986respectively. Her research interests includes the chem-istry, structure elucidation and pharmacologicalbehavior of chemical compounds from Apocynaceae,Annonaceae, and Rubiaceae plants in Malaysia espe-cially the antimalarial activity of phytochemical com-pounds to malaria parasites. She is a member of theMalaysian Natural Products Society and Analytical Sci-ences Society of Malaysia.

I. Sahidin was born in 1969 and work at the Depart-ment of Pharmacy, Haluoleo University, Kendari, SouthEast Sulawesi, Indonesia as a lecturer. He got his Ph.Dfrom Institut Teknologi Bandung, Indonesia in 2006 innatural products chemistry. He visited as a PostdoctoralResearcher the Universiti Kebangsaan Malaysia in 2010(Faculty of Sciences and Technology and Institute ofBiology Systems). In his research, Dr Sahidin is inter-ested in the chemical constituents of stilbenes fromDipterocarpaceae, terpenoids from Jatropha and phe-nolic compounds from Polygonaceae and their biologi-cal activities.