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Microbial Transformations of Gelomulide G: A Member of the Rare Class of Diterpene Lactones
Author(s) -
Choudhary M. Iqbal,
Gondal Humaira Y.,
Abbaskhan Ahmed
Publication year - 2005
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.200590112
Subject(s) - diterpene , chemistry , epimer , stereochemistry , aspergillus niger , biotransformation , transformation (genetics) , chemical transformation , organic chemistry , biochemistry , enzyme , gene
Abstract Microbial transformation of gelomulide G (3 β ,6 β‐ diacetoxy‐8 β ,14 β‐ epoxyabiet‐13(15)‐en‐16,12‐olide, 1 ) was carried out. Incubation of 1 with Aspergillus niger afforded two new metabolites, 3 β ,6 β‐ diacetoxy‐8 β ,14 β‐ dihydroxyabiet‐13(15)‐en‐16,12‐olide ( 2 ) and 3 β ,6 β‐ diacetoxy‐14 β‐ hydroxyabieta‐8(9),13(15)‐dien‐16,12‐olide ( 3 ). While Cunninghamella elegans afforded the 14‐epimer of 2 , i.e. , 3 β ,6 β‐ diacetoxy‐8 β ,14 α‐ dihydroxyabiet‐13(15)‐en‐16,12‐olide ( 4 ), along with 3 β ‐acetoxy‐6 β‐ hydroxy‐8 β ,14 β‐ epoxyabiet‐13(15)‐en‐16,12‐olide ( 5 ). The structures of the transformed products 2 – 5 were deduced to be new on the basis of MS and NMR data.