Heterogeneity of interflavanoid bond Location in loblolly pine bark procyanidins

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

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Heterogeneity of interflavanoid bond Location in loblolly pine bark procyanidins

Informally Refereed

Authors:

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

Year:

1983

Type:

Scientific Journal

Station:

Southern Research Station

Source:

Phytochemistry 22(1):275-281

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Abstract

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..

Citation

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