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
收藏
页码:2467 / 2477
页数:11
相关论文
共 34 条
[1]  
AQUIL M, 1991, J CHEM SOC P1, P1389
[2]   SYNTHESIS OF CONDENSED TANNINS .4. A DIRECT BIOMIMETIC APPROACH TO [4,6]-BIFLAVANOIDS AND [4,8]-BIFLAVANOIDS [J].
BOTHA, JJ ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1235-1245
[3]   CONDENSED TANNINS - DIRECT SYNTHESIS, STRUCTURE, AND ABSOLUTE-CONFIGURATION OF 4 BIFLAVANOIDS FROM BLACK WATTLE BARK (MIMOSA) EXTRACT [J].
BOTHA, JJ ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :700-702
[4]   OLIGOMERIC FLAVANOIDS .15. BASE-CATALYZED PYRAN REARRANGEMENTS OF PROCYANIDIN B-2, AND EVIDENCE FOR THE OXIDATIVE TRANSFORMATION OF B-TO A-TYPE PROCYANIDINS [J].
BURGER, JFW ;
KOLODZIEJ, H ;
HEMINGWAY, RW ;
STEYNBERG, JP ;
YOUNG, DA ;
FERREIRA, D .
TETRAHEDRON, 1990, 46 (16) :5733-5740
[5]   CONSTITUENTS OF DRAGONS BLOOD .1. STRUCTURE AND ABSOLUTE CONFIGURATION OF NEW OPTICALLY ACTIVE FLAVANS [J].
CARDILLO, G ;
MERLINI, L ;
NASINI, G ;
SALVADORI, P .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (23) :3967-+
[6]   COLOURING MATTERS OF AUSTRALIAN PLANTS .16. MINOR CONSTITUENTS OF DIANELLA-REVOLUTA AND STYPANDRA-GRANDIS [J].
COOKE, RG ;
DOWN, JG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (06) :1257-+
[7]   IDENTIFICATION OF 3 HYDROXYFLAVAN PHYTOALEXINS FROM DAFFODIL BULBS [J].
COXON, DT ;
ONEILL, TM ;
MANSFIELD, JW ;
PORTER, AEA .
PHYTOCHEMISTRY, 1980, 19 (05) :889-891
[8]   ASSESSMENT OF 3,4-TRANS AND 3,4-CIS RELATIVE CONFIGURATIONS IN THE A-SERIES OF (4,8)-LINKED PROANTHOCYANIDINS [J].
CRONJE, A ;
BURGER, JFW ;
BRANDT, EV ;
KOLODZIEJ, H ;
FERREIRA, D .
TETRAHEDRON LETTERS, 1990, 31 (26) :3789-3792
[9]   SOME STEREOCHEMICALLY IDENTICAL BIFLAVANOLS FROM BARK TANNINS OF ACACIA MEARNSII [J].
DREWES, SE ;
ROUX, DG ;
SAAYMAN, HM ;
EGGERS, SH ;
FEENEY, J .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (14) :1302-&
[10]   STEREOCHEMISTRY OF BIFLAVANOLS FROM BLACK WATTLE BARK - LEUCOROBINETINIDIN-(+)-CATECHIN AND LEUCOROBINETINIDIN-(+)-GALLOCATECHIN [J].
DREWES, SE ;
ROUX, DG ;
SAAYMAN, HM ;
FEENEY, J ;
EGGERS, SH .
CHEMICAL COMMUNICATIONS, 1966, (12) :370-&