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

共 34 条

[11] CONDENSED TANNINS .15. INTERRELATIONSHIPS OF FLAVONOID COMPONENTS IN WATTLE-BARK EXTRACT [J].

DREWES, SE ;

ROUX, DG .

BIOCHEMICAL JOURNAL, 1963, 87 (01) :167-&

[12] DIVERSITY OF STRUCTURE AND FUNCTION IN OLIGOMERIC FLAVANOIDS [J].

FERREIRA, D ;

STEYNBERG, JP ;

ROUX, DG ;

BRANDT, EV .

TETRAHEDRON, 1992, 48 (10) :1743-1803

[13]

HASHIMOTO F, 1989, CHEM PHARM BULL, V37, P3255

[14] PLANT PROANTHOCYANIDINS .2. PROANTHOCYANIDIN-A2 AND ITS DERIVATIVES [J].

JACQUES, D ;

HASLAM, E ;

BEDFORD, GR ;

GREATBANKS, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (23) :2663-2671

[15] KINETICS OF EPIMERIZATION OF (+)-CATECHIN AND ITS REARRANGEMENT TO CATECHINIC ACID [J].

KIATGRAJAI, P ;

WELLONS, JD ;

GOLLOB, L ;

WHITE, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (15) :2910-2912

[16] STUDIES ON ANTI-INFLAMMATORY AGENTS .6. ANTI-INFLAMMATORY CONSTITUENTS OF CINNAMOMUM-SIEBOLDII MEISSN [J].

OTSUKA, H ;

FUJIOKA, S ;

KOMIYA, T ;

MIZUTA, E ;

TAKAMOTO, M .

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1982, 102 (02) :162-172

[17] COLD-SET TANNIN-RESORCINOL-FORMALDEHYDE ADHESIVES OF LOWER RESORCINOL CONTENT [J].

PIZZI, A ;

OROVAN, E ;

CAMERON, FA .

HOLZ ALS ROH-UND WERKSTOFF, 1988, 46 (02) :67-71

[18]

PORTER LJ, 1986, J CHEM RES-S, P86

[19]

PORTER LJ, 1988, FLAVONOIDS ADV RES 1, P100

[20]

Roux D.C., 1975, J APPL POLYM SCI POL, V28, P335

← 1 2 3 4 →