94757-87-6Relevant academic research and scientific papers
Configuration and Conformation of Dihydroflavonols from Acacia Melanoxylon
Foo, Lai Yeap
, p. 813 - 818 (1987)
The isolation of two novel dihydroflavonols, namely (-)2,3-cis-3',4',7,8-tetrahydroxydihydroflavonol and (+/-)2,3-trans-3',4',7-trihydroxy-5-methoxydihydroflavonol together with the known (+/-)2,3-trans-3',4',7,8-tetrahydroxydihydroflavonol from Acacia melanoxylon is described. 1H NMR study shows the aryl substituent at C-2 in the 2,3-trans compounds is in the normal equatorial conformation but the 2,3-cis isomer, in contrast, has the aryl substituent in the unusual axial conformation.The elucidation of the 2,3-cis configuration of the dihydroflavonol and its co-occurrence with the metabolically related 2,3-cis-leucoanthocyanidins or flavan-3,4-diols provide the first evidence that the biosynthesis of flavan-3-ols and proanthocyanidins with the 2,3-cis configuration occur in a parallel pathway to that of the 2,3-trans compounds.Key Word Index - Acacia melanoxylon; Leguminosae; heartwood; 2,3-cis-3',4',7,8-tetrahydroxydihydroflavonol; 2,3-trans-3',4',7,8-tetrahydroxydihydroflavonol; 2,3-trans-3',4',7-trihydroxy-5-methoxy-dihydroflavonol; configuration; conformation; biogenesis.
