BIOSYNTHESIS OF IRIDOID GLUCOSIDES IN THUNBERGIA-ALATA

被引:12
作者
DAMTOFT, S
FREDERIKSEN, LB
JENSEN, SR
机构
[1] Department of Organic Chemistry, The Technical University of Denmark
关键词
THUNBERGIA ALATA; ACANTHACEAE; IRIDOID GLUCOSIDES; STILBERICOSIDE; BIOSYNTHESIS; H-2; NMR;
D O I
10.1016/S0031-9422(00)89574-6
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
Deoxy-[6,7,8,10-H-2] loganic acid and 8-epideoxy-[6,7,8,10-H-2] loganic acid were fed to Thunbergia alata. The former was incorporated into stilbericoside with retention of the label at H-6, H-7 and H-8. Administration of deuterium-labelled loganic acid, adoxosidic acid, capensioside and 8(S)-bisdeoxy-7,8-dihydroaucubin showed that the first steps in the biosynthesis of stilbericoside from deoxyloganic acid are most probably 10-hydroxylation followed by decarboxylation.
引用
收藏
页码:1599 / 1603
页数:5
相关论文
共 14 条
[1]   MONOTERPENE BIOSYNTHESIS .I. OCCURRENCE AND MEVALONOID ORIGIN OF GENTIOPICROSIDE AND LOGANIC ACID IN SWERTIA CAROLINIENSIS [J].
COSCIA, CJ ;
GUARNACCIA, R ;
BOTTA, L .
BIOCHEMISTRY, 1969, 8 (12) :5036-+
[2]   FURTHER NOTES ON RETZIACEAE - ITS CHEMICAL CONTENTS AND AFFINITIES [J].
DAHLGREN, R ;
NIELSEN, BJ ;
GOLDBLATT, P ;
ROURKE, JP .
ANNALS OF THE MISSOURI BOTANICAL GARDEN, 1979, 66 (03) :545-556
[3]   ALATOSIDE AND THUNALOSIDE, 2 IRIDOID GLUCOSIDES FROM THUNBERGIA-ALATA [J].
DAMTOFT, S ;
FREDERIKSEN, LB ;
JENSEN, SR .
PHYTOCHEMISTRY, 1994, 35 (05) :1259-1261
[4]   C-13 AND H-1-NMR SPECTROSCOPY AS A TOOL IN THE CONFIGURATIONAL ANALYSIS OF IRIDOID GLUCOSIDES [J].
DAMTOFT, S ;
JENSEN, SR ;
NIELSEN, BJ .
PHYTOCHEMISTRY, 1981, 20 (12) :2717-2732
[5]   IRIDOIDS AND VERBASCOSIDES IN RETZIA [J].
DAMTOFT, S ;
FRANZYK, H ;
JENSEN, SR ;
NIELSEN, BJ .
PHYTOCHEMISTRY, 1993, 34 (01) :239-243
[6]   BIOSYNTHESIS OF IRIDOID GLUCOSIDES IN LAMIUM-ALBUM [J].
DAMTOFT, S ;
JENSEN, SR ;
NIELSEN, BJ .
PHYTOCHEMISTRY, 1992, 31 (01) :135-137
[7]  
GEISSMAN T. A., 1966, TETRAHEDRON LETT, V12, P1245
[8]   CHEMOTAXONOMY OF THE ACANTHACEAE IRIDOIDS AND QUATERNARY AMINES [J].
JENSEN, HFW ;
JENSEN, SR ;
NIELSEN, BJ .
PHYTOCHEMISTRY, 1988, 27 (08) :2581-2589
[9]  
Jensen S. R., 1991, P PHYTOCHEMICAL SOC, P133
[10]  
JENSEN SR, 1989, PHYTOCHEMISTRY, V28, P97, DOI 10.1016/0031-9422(89)85017-4