Journal
PHYTOCHEMISTRY
Volume 65, Issue 16, Pages 2391-2399Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2004.06.026
Keywords
Arachis hypogaea; Leguminosae; peanut skin; proanthocyanidins
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Separation of the water-soluble fraction of peanut skins led to the isolation of five proanthocyanidins. Based on the spectroscopic investigation and partial acid catalyzed degradation, their structures were determined to be epicatechin-(2beta --> O --> 4beta --> 6)-[epicatechin-(4beta --> 8)]-catechin (1), epicatechin-(2beta --> O --> 7, 4beta --> 8) epicatechin-(4beta --> 8)-catechin-(4alpha --> 8)-epicatechin (2), and procyanidins B2 (3), B3 (4) and B4 (5). The absolute configuration of the new compounds was determined from their circular dichroism curves and the H-1 NMR spectra of analysis of flavan-3-ols formed by thiolytic degradation of 1 and 2 in the presence of a chiral dirhodium complex (dirhodium tetra-(R)-(trifluoromethyl) phenyl acetate). (C) 2004 Elsevier Ltd. All rights reserved.
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