BIOSYNTHESIS OF PHEROMONES IN FEMALE GAMETES OF MARINE BROWN-ALGAE (PHAEOPHYCEAE)

被引：33
|
作者：
STRATMANN, K
BOLAND, W
MULLER, DG
机构：
[1] UNIV KARLSRUHE,INST ORGAN CHEM,RICHARD WILLSTATTER ALLEE 2,W-7500 KARLSRUHE,GERMANY
[2] UNIV CONSTANCE,FAK BIOL,W-7750 CONSTANCE,GERMANY
来源：
TETRAHEDRON | 1993年 / 49卷 / 18期
关键词：
D O I：
10.1016/S0040-4020(01)90228-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Female gametes of the brown algae Ectocarpus siliculosus and Sphacelaria rigidula as well as thalli of Giffordia mitchellae metabolise externally added [H-2(n)]icosanoic acids into the hydrocarbon pheromones ectocarpene (1), dictyotene (2) and finavarrene (5). The series of the C11H16 hydrocarbons originates from all-cis-5,8,11,-14,17-icosapentaenoic acid (7); the C11H18 compound dictyotene (2) is produced from all-cis-5,8,11,14-icosate-traenoic acid (8) (arachidonic acid). The key step in the biosynthesis of giffordene (6) is a thermally allowed [1,7]-hydrogen shift of an 1,3Z,5Z,8Z-undecatetraene (21) intermediate derived from 7.
引用
收藏
页码：3755 / 3766
页数：12
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