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Hydroxylation of the Triterpenoid Nigranoic Acid by the Fungus Gliocladium roseum YMF1.00133
Author(s) -
Dong JinYan,
Chen YeGao,
Song HongChuan,
Zhu YanHui,
Zhou YongPing,
Li Lei,
He YanPing,
Cao Jie,
Zhang KeQin
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790015
Subject(s) - chemistry , hydroxylation , silica gel , metabolite , biotransformation , fungus , terpene , sephadex , mass spectrometry , triterpenoid , organic chemistry , column chromatography , nuclear magnetic resonance spectroscopy , stereochemistry , chromatography , biochemistry , enzyme , botany , biology
The ability of the fungus Gliocladium roseum YMF1.00133 to transform the bioactive nigranoic acid (=(24 Z )‐9,19‐cyclo‐3,4‐secolanosta‐4(28),24‐diene‐3,26‐dioic acid) was investigated. Three new products from the co‐cultures of nigranoic acid and G. roseum YMF1.00133 were obtained by employing a combination of Sephadex LH‐20 and silica‐gel column chromatography. The major metabolite was identified as 15 β ‐hydroxynigranoic acid, and the minor metabolites as 6 α ,15 β ‐dihydroxynigranoic acid and 7 β ,15 β ‐dihydroxynigranoic acid by mass spectrometry and NMR spectroscopy. This is the first report of the biotransformation of the A‐ring‐secocycloartene triterpenoid, nigranoic acid.