Literature DB >> 12398539

Novel 12-deoxy-16-hydroxyphorbol diesters isolated from the seed oil of Jatropha curcas.

Wilhelm Haas1, Heinz Sterk, Martin Mittelbach.   

Abstract

Six unstable intramolecular diterpene esters were isolated from the seed oil of Jatropha curcas. Five of these, Jatropha factors C(2)-C(6) (3-7), are new natural products, and the structure of the known Jatropha factor C(1) (2) has been revised. All compounds possess the same diterpene moiety, namely, 12-deoxy-16-hydroxyphorbol (1). The dicarboxylic acid moieties of 2-5 contain a bicyclo[3.1.0]hexane unit, and those of 6 and 7 a cyclobutane unit, which is described for the first time within this compound class. Compounds 4 and 5 are C-8' epimers. The structures of 2-7 were elucidated by spectroscopic methods and give an insight into the biogenesis of the characterized substances.

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Year:  2002        PMID: 12398539     DOI: 10.1021/np020060d

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  18 in total

1.  Development of a sensitive in vitro assay to quantify the biological activity of pro-inflammatory phorbol esters in Jatropha oil.

Authors:  Guillaume Pelletier; Bhaja K Padhi; Jalal Hawari; Geoffrey I Sunahara; Raymond Poon
Journal:  In Vitro Cell Dev Biol Anim       Date:  2015-01-15       Impact factor: 2.416

2.  Molecularly Imprinted Polymer-Coated Probe Electrospray Ionization Mass Spectrometry Determines Phorbol Esters and Deoxyphorbol Metabolites in Jatropha curcas Leaves.

Authors:  Lidya C da Silva; Thays C de Carvalho; Igor Pereira; Julio Cesar Marana; Bruno G Laviola; Patricia V Abdelnur; Boniek G Vaz
Journal:  J Am Soc Mass Spectrom       Date:  2019-07-24       Impact factor: 3.109

3.  Practical synthesis of prostratin, DPP, and their analogs, adjuvant leads against latent HIV.

Authors:  Paul A Wender; Jung-Min Kee; Jeffrey M Warrington
Journal:  Science       Date:  2008-05-02       Impact factor: 47.728

4.  Production of bioactive diterpenoids in the euphorbiaceae depends on evolutionarily conserved gene clusters.

Authors:  Andrew J King; Geoffrey D Brown; Alison D Gilday; Tony R Larson; Ian A Graham
Journal:  Plant Cell       Date:  2014-08-29       Impact factor: 11.277

5.  Screening for toxic phorbol esters in jerky pet treat products using LC-MS.

Authors:  Upul Nishshanka; Hiranthi Jayasuriya; Chaitali Chattopadhaya; Philip J Kijak; Pak-Sin Chu; Renate Reimschuessel; Andriy Tkachenko; Olgica Ceric; Hemakanthi G De Alwis
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2016-03-21       Impact factor: 3.205

6.  Engineering low phorbol ester Jatropha curcas seed by intercepting casbene biosynthesis.

Authors:  Chunhong Li; Ailing Ng; Lifen Xie; Huizhu Mao; Chengxiang Qiu; Ramachandran Srinivasan; Zhongchao Yin; Yan Hong
Journal:  Plant Cell Rep       Date:  2015-10-06       Impact factor: 4.570

7.  Sequence analysis of the genome of an oil-bearing tree, Jatropha curcas L.

Authors:  Shusei Sato; Hideki Hirakawa; Sachiko Isobe; Eigo Fukai; Akiko Watanabe; Midori Kato; Kumiko Kawashima; Chiharu Minami; Akiko Muraki; Naomi Nakazaki; Chika Takahashi; Shinobu Nakayama; Yoshie Kishida; Mitsuyo Kohara; Manabu Yamada; Hisano Tsuruoka; Shigemi Sasamoto; Satoshi Tabata; Tomoyuki Aizu; Atsushi Toyoda; Tadasu Shin-i; Yohei Minakuchi; Yuji Kohara; Asao Fujiyama; Suguru Tsuchimoto; Shin'ichiro Kajiyama; Eri Makigano; Nobuko Ohmido; Nakako Shibagaki; Joyce A Cartagena; Naoki Wada; Tsutomu Kohinata; Alipour Atefeh; Shota Yuasa; Sachihiro Matsunaga; Kiichi Fukui
Journal:  DNA Res       Date:  2010-12-13       Impact factor: 4.458

8.  Detoxification of toxic phorbol esters from Malaysian Jatropha curcas Linn. kernel by Trichoderma spp. and endophytic fungi.

Authors:  Azhar Najjar; Norhani Abdullah; Wan Zuhainis Saad; Syahida Ahmad; Ehsan Oskoueian; Faridah Abas; Youssuf Gherbawy
Journal:  Int J Mol Sci       Date:  2014-02-05       Impact factor: 5.923

9.  Phorbol esters isolated from Jatropha meal induced apoptosis-mediated inhibition in proliferation of chang and Vero cell lines.

Authors:  Ehsan Oskoueian; Norhani Abdullah; Syahida Ahmad
Journal:  Int J Mol Sci       Date:  2012-10-24       Impact factor: 5.923

Review 10.  Jatropha curcas, a biofuel crop: functional genomics for understanding metabolic pathways and genetic improvement.

Authors:  Fatemeh Maghuly; Margit Laimer
Journal:  Biotechnol J       Date:  2013-10       Impact factor: 4.677

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