Structure and stereochemistry of triflavanoids containing both ether and carbon-carbon interflavanyl bonds

被引:7
作者
Bennie, L
Coetzee, J
Malan, E
Ferreira, D [1 ]
机构
[1] Univ Mississippi, Pharmaceut Sci Res Inst, Natl Ctr Nat Prod Res, Sch Pharm, University, MS 38677 USA
[2] Univ Orange 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 caffra; Leguminosae; triflavanoids; pro-/leucoanthocyanidins; pro-/leucoteracacinidins; pro-/leucomelacacinidins; absolute configuration; reductive cleavage;
D O I
10.1016/S0031-9422(01)00044-9
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 first triflavanoids with both C-C and C-O-C interflavanyl bonds, epioritin-(4 beta -->6)-epioritin-(4 alpha -->4)-epioritin-4 beta -ol, epioritin-(4 beta -->3)-epioritin-(4 beta -->6)-epioritin-4 beta -ol and epioritin-(4 beta -->3)-epioritin-(4 beta --> 6)-epimesquitol-4 alpha -ol. were identified in the heartwood of Acacia caffra. The ethereal interflavanyl bond is readily susceptible to reductive cleavage with sodium cyanoborohydride in trifluoroacetic acid/dichloromethane which hence permits the unequivocal assignment of the absolute configuration of constituent flavanyl units. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1023 / 1034
页数:12
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