Biosynthesis of the algal pheromone fucoserratene by the freshwater diatom Asterionella formosa (Bacillariophyceae)

✍ Scribed by Marc Hombeck; Wilhelm Boland

• Book ID: 104208800
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 583 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00660-7

✦ Synopsis

The freshwater diatom Asterionellaformosa (Bacillariophyceae) produces octa-l,3E,5Z-triene (6) (fucoserratene), previously identified as the sexual pheromone of the brown seaweed Fucus serratus. Fucoserratene is biosynthesised from eicosa-5,8,11,14,17-pentaenoic acid (7) by oxidative cleavage of the corresponding 12-hydroperoxy intermediate 8. The biosynthetic sequence was established using eicosa-5,8,11,14-tetraen-17-ynoic acid (18), a structural analogue of 7, which was converted to octa-l,3E-dien-5yne ( 21), a structural analogue of 6, by homogenates of Asterionella formosa. In addition, a general approach to highly unsaturated eicosanoids from arachidonic acid is described.