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

页码：3755 / 3766

页数：12

共 27 条

[1] BIOGENETICALLY INSPIRED STEREOSPECIFIC SYNTHESIS OF THE DIENYLVINYLCYCLOPROPANE GAMETE ATTRACTANT DICTYOPTERENE-B [J].