Novel 12-deoxy-16-hydroxyphorbol diesters isolated from the seed oil of Jatropha curcas.
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.
Haas
Wilhelm
W
Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, Austria.
Sterk
Heinz
H
Mittelbach
Martin
M
D006900:Hydroxylation; D031286:Jatropha / Q000737:chemistry* / Q000196:embryology; D010703:Phorbol Esters / Q000737:chemistry / Q000302:isolation & purification*; D010938:Plant Oils / Q000737:chemistry*; D013057:Spectrum Analysis
D010703:Phorbol Esters; D010938:Plant Oils