OLIGOMERIC FLAVANOIDS .16. NOVEL PROROBINETINIDINS AND THE 1ST A-TYPE PROANTHOCYANIDIN WITH A 5-DEOXY A-RING AND A 3,4-CIS C-RING FROM THE MAIDEN INVESTIGATION OF COMMERCIAL WATTLE BARK EXTRACT

被引：20

作者：

CRONJE, A ^{[1
]}

STEYNBERG, JP ^{[1
]}

BRANDT, EV ^{[1
]}

YOUNG, DA ^{[1
]}

FERREIRA, D ^{[1
]}

机构：

[1] UNIV ORANGE FREE STATE, DEPT CHEM, POB 339, BLOEMFONTEIN 9300, SOUTH AFRICA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 20期

关键词：

D O I：

10.1039/p19930002467

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Structural examination of the phenolic metabolites of commercially used wattle bark extract reveals the presence of a range of novel flavanoids comprising (-)-epirobinetinidol 1, the first C-methyl proanthocyanidin, (-)-fisetinidol-(4alpha,8)-6-methyl-(+)-catechin 3, the first prorobinetinidins with 3,4-cis C-ring configurations 7 and 9, and the unique A-type prorobinetinidin 11 representing the first entry amongst this class of oligoflavanoids exhibiting a 5-deoxy A- and a 3,4-cis C-ring. They are accompanied by a range of functionalized prorobinetinidin-type tetrahydropyrano[2,3-f]chromenes 20, 23, 25 and 28 and the trimeric 'isomerization-intermediate' 32, all exhibiting the characteristic structural features that are essential for the use of 'Mimosa' extract in cold-setting adhesives and leather-tanning applications. In addition, evidence demonstrating that the dynamic A-E conformational equilibrium of flavan-3-ol moieties in condensed tannins may be influenced by external factors is presented.

引用

页码：2467 / 2477

页数：11

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