(4→6)-coupled proteracacinidins and promelacacinidins from Acacia galpinii and Acacia caffra

被引:13
作者
Bennie, L
Coetzee, J
Malan, E
Ferreira, D [1 ]
机构
[1] Univ Mississippi, Natl Ctr Nat Prod Res, Pharmaceut Sci Res Inst, Sch Pharm, University, MS 38677 USA
[2] Univ Free State, Dept Chem, ZA-9300 Bloemfontein, South Africa
基金
新加坡国家研究基金会;
关键词
Acacia galpinii; Acacia caffra; Leguminosae; biflavanoids; proteracacinidins; promelacacinidins; proanthocyanidins;
D O I
10.1016/S0031-9422(02)00124-3
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The series of naturally occurring proanthocyanidins with 7,8-dihydroxylated A-rings is extended by identification of the proteracacinidins epioritin-(4beta-->6)-oritin-4alpha-ol, epiortin-(4beta-->6)-ent-oritin-4alpha-ol, ent-oritin-(4beta-->6)-epioritin-4alpha-ol, ent-oritin-(4beta-->6)oritin-4alpha-ol, ent-oritin-(4alpha-->6)-epioritin-4alpha-ol, ent-oritin-(4alpha-->6)-oritin-4alpha-ol, ent-oritin-(4alpha-->6)-epioritin-4beta-ol, the 'mixed' proteracacinidins/-melacacinidins epioriitin-(4beta-->6)-epimesquitol-4alpha-ol, epioritin-(4beta-->6)-epimesquitol-4beta-ol and epimesquitol-(4beta-->6)-epioritin-4alpha-ol, and the promelacacinidin epimesquitol-(4beta-->6)-epimesquitol-4alpha-ol. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:521 / 532
页数:12
相关论文
共 28 条
[1]   Structure and stereochemistry of dimeric proteracacinidins possessing the rare C-4(C) → C-5(D) interflavanyl linkage [J].
Bennie, L ;
Coetzee, J ;
Malan, E ;
Ferreira, D .
PHYTOCHEMISTRY, 2002, 59 (06) :673-678
[2]   Structure and stereochemistry of triflavanoids containing both ether and carbon-carbon interflavanyl bonds [J].
Bennie, L ;
Coetzee, J ;
Malan, E ;
Ferreira, D .
PHYTOCHEMISTRY, 2001, 57 (06) :1023-1034
[3]   Oligomeric flavanoids.: Part 34:: Doubly-linked proteracacinidin analogues from Acacia caffra and Acacia galpinii [J].
Bennie, L ;
Coetzee, J ;
Malan, E ;
Woolfrey, JR ;
Ferreira, D .
TETRAHEDRON, 2001, 57 (04) :661-667
[4]   Oligomeric flavonoids -: Part 32 -: Structure and synthesis of ether-linked proteracacinidin and promelacacinidin proanthocyanidins from Acacia caffra [J].
Bennie, L ;
Malan, E ;
Coetzee, J ;
Ferreira, D .
PHYTOCHEMISTRY, 2000, 53 (07) :785-793
[5]   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
[6]   The formation and stability of flavans with 2,3-cis-3,4-cis configuration [J].
Coetzee, J ;
Malan, E ;
Ferreira, D .
TETRAHEDRON, 1999, 55 (33) :9999-10004
[7]   Oligomeric flavanoids - Part 29: Structure and synthesis of novel ether-linked [4-O-4]bis-teracacinidins [J].
Coetzee, J ;
Malan, E ;
Ferreira, D .
TETRAHEDRON, 1998, 54 (31) :9153-9160
[8]  
COETZEE J, 1998, J CHEM RES, V526, P2287
[9]   PLANT PROANTHOCYANIDINS .3. CONFORMATIONAL AND CONFIGURATIONAL STUDIES OF NATURAL PROCYANIDINS [J].
FLETCHER, AC ;
PORTER, LJ ;
HASLAM, E ;
GUPTA, RK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (14) :1628-1637