S. Tahara, J. Ingham, J. Ingham
1989
Citations
0
Influential Citations
15
Citations
Journal
Phytochemistry
Abstract
Abstract The prenylated isoflavone 2,3-dehydrokievitone was methylated with ethereal diazomethane to yield the corresponding 7-O-methyl derivative. This was metabolized by Botrytis cinerea to give 7-O-methyl-2,3-dehydrokievitone epoxide and 7-O-methyl-2,3-dehydrokievitone glycol. The structures of these metabolises were established by standard spectroscopic methods (UV, MS and 1HNMR and by chemical conversion. Both compounds were found to possess the S-absolute stereochemistry. The epoxide is an analogue of the key metabolic intermediate thought to be involved in the formation, by fungi, of various dihydrofurano-, dihydropyrano- and 2,3-dihydroxy-3-methylbutyl-substituted isoflavones from precursor compounds containing a prenyl side-chain with ortho-hydroxylation.