BIOSYNTHESIS OF IRIDOIDS IN SYRINGA AND FRAXINUS - CARBOCYCLIC IRIDOID PRECURSORS

被引:22
作者
DAMTOFT, S
FRANZYK, H
JENSEN, SR
机构
[1] Department of Organic Chemistry, The Technical University of Denmark
关键词
FRAXINUS EXCELSIOR; SYRINGA JOSIKAEA; S-VULGARIS; OLEACEAE; SECOIRIDOID GLUCOSIDES; BIOSYNTHESIS; OLEOSIDES; OLEUROPEIN;
D O I
10.1016/0031-9422(95)00210-X
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
Feeding experiments with deuterium-labelled precursors to Fraxinus excelsior, Syringa josikaea and S. vulgaris have shown that the biosynthesis of the oleoside-type secoiridoids (e.g. oleuropein) proceeds via iridodial, iridotrial, deoxy-loganic acid aglucon and deoxy-loganic acid. Hydroxylation of the 7 alpha-position is followed by oxidation and methylation of C-11 to give 7-ketologanin, the last carbocyclic iridoid precursor of the oleosides. The sequences of the steps between deoxy-loganic acid and 7-ketologanin may differ with plant species and time of year. 8-Epi-kingisidic acid and 8-epi-kingiside can be formed from 8-ketologanic acid (and its methyl ester). The secoiridoids, fliederoside and lilacoside, from S. vulgaris have been characterized.
引用
收藏
页码:785 / 792
页数:8
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