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Title: Heterogeneity of interflavanoid bond Location in loblolly pine bark procyanidins

Author: Hemingway, Richard W.; Karchesy, Joseph J.; McGraw, Gerald W.; Wielesek, Richard A.;

Date: 1983

Source: Phytochemistry 22(1):275-281

Publication Series: Miscellaneous Publication

Description: Procyanidins B-1, B-3 and B-7 were obtained from Pinus taeda phloem in yields of 0.076, 0.021 and 0.034% of unextracted dry wt. Procyanidins B-1 and B-7 were produced in relative yields of 2.4:1 by biosynthetically patterned synthesis from catechin and loblolly pine tannins. Partial acid-catalysed thiolytic cleavage of loblolly pine phloem tannins produced (2R,3S,4S)-2,3,-cis-3,4-trans-3,3',4',5,7-pencahydroxy-4-phenylthioftavan and both (2R,3R,4R)-2,3-cis-3,4-trans-3,3'4',5,7-pentahydroxy-4-(2R,3S,4S)-2,3-cis-3,4- trans-3,3',4',5,7-pentahydroxy-4-phenylthioftavan-8-yl]ftavan and (2R,3R,4R)-2,3-cis-3,4-trans-3,3',4',5,7-4-[(2R,3S,4S)-2,3-cis-3,4-trans-3,3',4',5,7-pentahydroxy-4-phenylthioftavan-6-yl]ftavan in ratios of 3:1 demonstrating regio-isomerism of the interflavanoid linkage in the polymeric procyanidins of loblolly pine bark..

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Hemingway, Richard W.; Karchesy, Joseph J.; McGraw, Gerald W.; Wielesek, Richard A. 1983. Heterogeneity of interflavanoid bond Location in loblolly pine bark procyanidins. Phytochemistry 22(1):275-281

 


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