€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****CANCER RESEARCH***** Hirota M Suttajit M Suguri H Endo Y Shudo K Wongchai V Hecker E Fujiki H A new tumor promoter from the seed oil of Jatropha curcas L., an intramolecular diester of 12-deoxy-16-hydroxyphorbol. In: Cancer Res (1988 Oct 15) 48(20):5800-4 ISSN: 0008-5472 A new type of phorbol ester, which has a macrocyclic dicarboxylic acid diester structure, was isolated from the seed oil of Jatropha curcas L. (Euphorbiaceae). Based on the results of spectroscopic analyses of the compound and its chemical degradation products, its structure is proposed to be an intramolecular 13,16-diester of 12- deoxy-16-hydroxyphorbol, 12-deoxy-16-hydroxyphorbol-4'-[12',14'- butadienyl]-6'-[16',18',20' - nonatrienyl]-bicyclo[3.1.0]hexane-(13- O)-2'-[carboxylate]-(16-O)-3 '- [8'-butenoic-10']ate (DHPB). DHPB showed slightly weaker biological and biochemical activities than 12- O-tetradecanoylphorbol-13-acetate (TPA). DHPB induced ornithine decarboxylase in mouse skin (2.8 nmol CO2/30 min/mg protein/34 nmol application), inhibited the specific binding of [3H]-12-O- tetradecanoylphorbol-13-acetate to phorbol ester receptors (50% effective dose, 17.0 nM), and activated protein kinase C in vitro (50% effective dose, 36.0 nM). Also, a weak tumor-promoting activity of DHPB was found in a two-stage carcinogenesis experiment on mouse skin. One week after initiation of mice with 100 micrograms of 7,12- dimethyl-benz(a)anthracene, topical application, twice a week, of 2 micrograms of DHPB until week 17, followed by application of 5 microgram of DHPB until week 30 at the same rate, resulted in 46.7% incidence of tumors by week 30. The groups treated with 7,12- dimethylbenz(a)anthracene alone or DHPB alone did not produce significant numbers of tumors. These results indicate that the new phorbol ester, DHPB, is a tumor promoter with weaker activity than 12- O-tetradecanoylphorbol-13-acetate. Registry Numbers: 117855-87-5 (12-deoxy-16-hydroxyphorbol-4'-(12',14'-butadienyl)-6'-(16',18',20'-nonatrienyl)-bicyclo(3.1.0)hexane-(13-O)-2'-(carboxylate)-(16-O)-3'-(8'-butenoic-10')ate) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****CHEMICAL AND PHARMACEUTICAL BULLETIN***** Okuyama E Okamoto Y Yamazaki M Satake M Pharmacologically active components of a Peruvian medicinal plant, huanarpo (Jatropha cilliata). In: Chem Pharm Bull (Tokyo) (1996 Feb) 44(2):333-6 ISSN: 0009-2363 From Jatropha cilliata M. Arg., a Peruvian medicinal plant, isoorientin and orientin were isolated as anxiolytic components by using the isolation guide of anti-conflict effect in mice. Several related flavonoids were also tested for this effect. Another bioassay- guided isolation using the acetic acid-induced writhing method gave a coumarin compound, fraxetin, as an analgesic principle. Registry Numbers: 439-14-5 (Diazepam) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****FEBS LETTERS***** van den Berg AJ Horsten SF Kettenes-van den Bosch JJ Kroes BH Beukelman CJ Leeflang BR Labadie RP Curcacycline A--a novel cyclic octapeptide isolated from the latex of Jatropha curcas L. In: FEBS Lett (1995 Jan 30) 358(3):215-8 ISSN: 0014-5793 From the latex of Jatropha curcas L. (Euphorbiaceae) a novel cyclic octapeptide was isolated, which we named curcacycline A. The compound was found to contain one threonine, one valine, two glycine, and four leucine residues. By two-dimensional 1H-NMR spectroscopy (HOHAHA and ROESY), its sequence was determined to be Gly1-Leu2-Leu3-Gly4-Thr5- Val6-Leu7-Leu8-Gly1+ ++. Curcacycline A displays a moderate inhibition of (i) classical pathway activity of human complement and (ii) proliferation of human T-cells. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****HUMAN TOXICOLOGY***** Abdu-Aguye I Sannusi A Alafiya-Tayo RA Bhusnurmath SR Acute toxicity studies with Jatropha curcas L. In: Hum Toxicol (1986 Jul) 5(4):269-74 ISSN: 0144-5952 The seeds of Jatropha curcas L. ingested accidentally by two children aged 3 and 5 years led to a clinical syndrome of restlessness, severe vomiting and dehydration. A systematic study of the seeds indicated that they produced toxic effects in mice. Macroscopic anal haemorrhage and death occurred when the seeds were administered with the feed. Post-mortem examination revealed infarction of various parts of the gastrointestinal tract with congested vessels. Sodium chloride solution (150 mmol/l: saline) extract of the dried seed administered intraperitoneally into mice caused death in doses as low as 1 mg/kg. Post-mortem studies in this case showed widespread haemorrhages involving the colon, lungs as well as infarction of the liver. Larger intraperitoneal doses (greater than 30 mg/kg) were lethal rapidly but not associated with gross gastrointestinal haemorrhage. Registry Numbers: 9009-86-3 (Ricin) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF ETHNOPHARMACOLOGY***** Kosasi S 't Hart LA van Dijk H Labadie RP Inhibitory activity of Jatropha multifida latex on classical complement pathway activity in human serum mediated by a calcium- binding proanthocyanidin. In: J Ethnopharmacol (1989 Nov) 27(1-2):81-9 ISSN: 0378-8741 This study isolates and characterizes the anti-complement constituent(s) present in the latex of Jatropha multifida, in an attempt to explain the traditional application of the latex in the treatment of infected wounds. Guided by the inhibition of classical pathway (CP) complement activity in human serum, a polymer was isolated which could be characterized as a proanthocyanidin. The polymer inhibits CP activation of the complement cascade, while alternative pathway (AP) activation is relatively insensitive to the polymer. This is due to the selective depletion of Ca2+, but not Mg2+, from the incubation medium. Registry Numbers: 18206-61-6 (proanthocyanidin) 7440-70-2 (Calcium) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF NATURAL PRODUCTS***** Villarreal AM Dominguez XA Williams HJ Scott AI Reibenspies J Citlalitrione, a new diterpene from Jatropha dioica var. sessiliflora. In: J Nat Prod (1988 Jul-Aug) 51(4):749-53 ISSN: 0163-3864 Solvent partitioning and column chromatography of MeOH root extracts of Jatropha dioica yielded four pure compounds, beta-sitosterol, jatropholone B, a previously unknown diterpene epoxytrione given the trivial name citlalitrione, and riolozatrione. Structures were determined using physical and spectral techniques and X-ray crystallography. Registry Numbers: 116368-91-3 (citlalitrione) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF ORGANIC CHEMISTRY***** Torrance SJ Wiedhopf RM Cole JR Arora SK Bates RB Beavers WA Cutler RS Antitumor agents from Jatropha macrorhiza (Euphorbiaceae). II. Isolation and characterization of jatrophatrione. In: J Org Chem (1976 May 14) 41(10):1855-7 ISSN: 0022-3263 [No Abstract Available] €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Torrance SJ Wiedhopf RM Cole JR Arora SK Bates RB Beavers WA Cutler RS ANTITUMOR AGENTS FROM JATROPHA MACRORHIZA (EUPHORBIACEAE). II. ISOLATION AND CHARACTERIZATION OF JATROPHATRIONE. In: J Org Chem (1976) 41(10):1855-1857 ISSN: 0022-3263 Jatrophatrione, a diterpene isolated from the chloroform extract of Jatropha macrorhiza Benth roots, was demonstrated to have antitumor activity (on increase in the survival of treated animals over that of controls) of 130% test/control and 141% test/control, respectively, at 1 and 0.5 mg/kg in the P-388 lymphocytic leukemia system. X-ray, crystallographic, and spectral data are presented and compared with those of jatrophone. (11 refs) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF PHARMACY AND PHARMACOLOGY***** Nath LK Dutta SK Extraction and purification of curcain, a protease from the latex of Jatropha curcas Linn. In: J Pharm Pharmacol (1991 Feb) 43(2):111-4 ISSN: 0022-3573 A proteolytic enzyme, curcain, has been extracted from the latex of Jatropha curcas Linn. The enzyme was purified by chromatography on carboxymethyl cellulose and gel filtration on Sephadex G-200. The homogeneity of protein associated with curcain was established by non- denatured polyacrylamide gel electrophoresis using a discontinuous buffer system. The molecular weight of curcain was estimated by Sephadex G-100 gel filtration using a calibration curve of standard proteins to be around 22,000 daltons. Registry Numbers: EC 3.4 (Peptide Hydrolases) EC 3.4.- (Peptide Peptidohydrolases) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JOURNAL OF PHARMACEUTICAL SCIENCES***** Torrance SJ Wiedhopf RM Cole JR Antitumor agents from Jatropha macrorhiza (Euphorbiaceae) III: acetylaleuritolic acid. In: J Pharm Sci (1977 Sep) 66(9):1348-9 ISSN: 0022-3549 The triterpene acetylaleuritolic acid was isolated from Jatropha macrorhiza (Euphorbiaceae) and showed tumor-inhibitory properties toward the P-388 lymphocytic leukemia test system. The compound was identified by means of IR, PMR, and mass spectrometry and by its transformation into the known methyl acetyloleanolate. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Torrance SJ Wiedhopf RM Cole JR ANTITUMOR AGENTS FROM JATROPHA MACRORHIZA (EUPHORBIACEAE) III: ACETYLALEURITOLIC ACID In: J Pharm Sci (1977) 66(9):1348-1349 ISSN: 0022-3549 The triterpene acteylaleuritolic acid isolated from ethanol extracts of the roots of Jatropha macrorhiza (Euphorbiaceae) demonstrated test/control (T/C) activities of 158 and 128% at dose levels of 1.0 and 1.4 mg/kg, respectively, in the P-388 lymphocytic leukemia test system. Identification of the compound was obtained through infra red, proton magnetic resonance, mass spectroscopy, and by its tranformation to the known methyl actyloleanolate. (5 Refs) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Wiedhopf RM Trumbull ER Cole JR Antitumor agents from Jatropha macrorhiza (Euphorbiaceae) I: isolation and characterization of jatropham. In: J Pharm Sci (1973 Jul) 62(7):1206-7 ISSN: 0022-3549 [No Abstract Available] €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Wiedhopf RM Trumbull ER Cole JR ANTITUMOR AGENTS FROM JATROPHA MACRORHIZA (EUPHORBIACEAE) I: ISOLATION AND CHARACTERIZATION OF JATROPHAM In: J Pharm Sci (1973) 62(7):1206-1207 ISSN: 0022-3549 A new lactam isolated from Jatropha macrorhiza (Euphorbiaceae), jatropham, has shown tumor-inhibitory properties against P388 lymphocytic leukemia. Solvent extractions (with hexane followed by acetonitrile) of the chloroform extract of leaves, stems, flowers, and fruits of the plant yielded a crystalline compound from the acetonitrile; this compound demonstrated activity (T/C 125%) at 45 mg/kg in the P388 system. It was identified by NMR, UV, IR, rotary dispersion, mass spectrometry, and classical chemical procedures as 5- hydroxy-4-methyl-3-pyrrolin-2-one. (6 refs) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****JAPANESE JOURNAL OF CANCER RESEARCH***** Horiuchi T Fujiki H Hirota M Suttajit M Suganuma M Yoshioka A Wongchai V Hecker E Sugimura T Presence of tumor promoters in the seed oil of Jatropha curcas L. from Thailand. In: Jpn J Cancer Res (1987 Mar) 78(3):223-6 ISSN: 0910-5050 The seed oil of Jatropha curcas L. was shown to contain skin tumor promoters in a two-stage mouse carcinogenesis experiment. By using the irritant test on mouse ear to monitor activity, the "irritant fraction" was partially purified from the methanol extract of the seed oil by column chromatographies on Florisil and Sephadex LH-20. The irritant fraction obtained induced ornithine decarboxylase in mouse skin and inhibited the specific binding of 3H-12-O- tetradecanoylphorbol-13-acetate to a particulate fraction of mouse skin. After initiation with 7,12-dimethylbenz[a]anthracene (DMBA), this "irritant fraction" induced tumors in the skin of 36% of the mice tested in 30 weeks. Tumor incidences in the groups treated with DMBA alone and "irritant fraction" alone were 7% and 13% in week 30, respectively. Since the skin of Thai people comes into direct contact with this seed oil, an epidemiological study on human skin cancer in Thailand is indicated. Registry Numbers: EC 4.1.1.17 (Ornithine Decarboxylase) 16561-29-8 (Tetradecanoylphorbol Acetate) 57-97-6 (9,10-Dimethyl-1,2-benzanthracene) €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****PHYTOCHEMISTRY***** Van den Berg AJ Horsten SF Kettenes-van den Bosch JJ Beukelman CJ Kroes BH Leeflang BR Labadie RP Podacycline A and B, two cyclic peptides in the latex of Jatropha podagrica. In: Phytochemistry (1996 May) 42(1):129-33 ISSN: 0031-9422 Two novel cyclic peptides were isolated from the latex of Jatropha podagrica, which we named podacycline A and B. Podacycline A is a cyclic nonapeptide with the sequence Gly1-Leu2-Leu3-Gly4-Ala5-Val6- Trp7-Ala8-Gly9+ ++-Gly1. The sequence of podacycline B, a cyclic heptapeptide, was determined to be Phe1-Ala2-Gly3-Thr4-Ile5-Phe6-Gly7- Phe1. The amino acid residues of both compounds were found to have the L-configuration. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****PLANT FOODS FOR HUMAN NUTRITION***** Ogbobe O Akano V The physico-chemical properties of the seed and seed oil of Jatropha gossipifolia. In: Plant Foods Hum Nutr (1993 May) 43(3):197-200 ISSN: 0921-9668 The physico-chemical properties of the seed and seed oil of Jatropha gossipifolia were assessed by standard methods. The seed contains 35.8% crude oil of iodine value 107.25, 13.40% protein, 9.25% fibre, 30.32% carbohydrate and 6.0 g/kg saponins. The fatty acid composition of the seed oil was determined by GC-MS. Caprylic, myristic, palmitoleic, palmitic, oleic, stearic, linoleic, vernolic, arachidic, behenic and lignoceric acids were found. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****PLANTA MEDICA***** Labadie RP van der Nat JM Simons JM Kroes BH Kosasi S van den Berg AJ t' Hart LA van der Sluis WG Abeysekera A Bamunuarachchi A et al An ethnopharmacognostic approach to the search for immunomodulators of plant origin. In: Planta Med (1989 Aug) 55(4):339-48 ISSN: 0032-0943 The search for immunomodulating plant constituents through basic and field inquiries into the literature and practices of traditional Indian medicine is treated. The strategy of data collecting proceeds through aspects of an ethnobotanical, an ethnopharmaceutical, an ethnopharmacological, and an ethnomedical nature. In the experimental immunopharmacognostic phase, immunomodulatory compounds are isolated and purified through action-guided fractionation procedures. The results described here refer to activities found on human complement activation and on PMN leucocytes activation. The immunomodulating plant compounds included in this report were isolated from Azadirachta indica bark, Woodfordia fructicosa flowers, Picrorhiza kurroa roots, and Jatropha multifida latex. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ Horsten SF van den Berg AJ Kettenes-van den Bosch JJ Leeflang BR Labadie RP Cyclogossine A: a novel cyclic heptapeptide isolated from the latex of Jatropha gossypifolia. In: Planta Med (1996 Feb) 62(1):46-50 ISSN: 0032-0943 From the latex of Jatropha gossypifolia L. (Euphorbiaceae) a novel cyclic heptapeptide was isolated, which we named cyclogossine A. A combination of amino acid analysis, FAB mass spectrometry, and two dimensional 1H-NMR spectroscopy (TOCSY and ROESY) was used to determine the primary structure. The compound was found to contain one glycine, one alanine, one valine, two leucine, one threonine, and one tryptophan residue; its amino acid sequence is: Leu 1 - Ala 2 - Thr 3 - Trp 4 - Leu 5 - Gly 6 - Val 7. The absolute configurations of the amino acids were determined by chiral gas chromatography; all have the L-configuration. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€ *****RESEARCH COMMUNICATIONS IN CHEMICAL PATHOLOGY AND PHARMACOLOGY** Rojanapo W Pimbua J Glinsukon T Naengchomnong W Thebtaranonth Y Failure of diterpenes from Jatropha curcas to induce mutation in Salmonella typhimurium TA98 and TA100. In: Res Commun Chem Pathol Pharmacol (1987 Dec) 58(3):397-400 ISSN: 0034-5164 No mutagenicity of five diterpenes isolated from the roots of Jatropha curcas was detected by Ame's test using both TA98 and TA100 tester strains with or without S-9 fraction from livers of rats treated with polychlorinated biphenyl. €€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€€