Condensed tannins. 6. Biochemical and stereochemical interrelationships of (+)-fustin from black-wattle heartwood (Acacia mollissima)

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Abstract
(+)-Fustin and fisetin have been isolated from the heartwood of Acacia mollissima. (+)-Fustin has been shown to be enantiomorphous with (-)-fustin from Rhus cotinus, whereas R. glabra, R. succedanea and R. vernicifera contain racemic mixtures of these enantiomorphs. The stereochemistry of these fustins is inferred from previous work. (+)-Fustin was converted into (+)-7:3[image]:4[image]-trihydroxyflavan-3:4-diol [(+)-mollisacacidin] by hydrogenation. The radial distributions of (+)-mollisacacidin, (+)-fustin and fisetin in wattle heartwood were estimated. The findings suggest that (+)-mollisacacidin is the primary precursor from which (+)-fustin and fisetin are formed by dehydrogenation.