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

J Nat Prod. 2002 Oct;65(10):1434-40. doi: 10.1021/np020060d.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydroxylation
  • Jatropha / chemistry*
  • Jatropha / embryology
  • Phorbol Esters / chemistry
  • Phorbol Esters / isolation & purification*
  • Plant Oils / chemistry*
  • Spectrum Analysis

Substances

  • Phorbol Esters
  • Plant Oils