Abstract
The fresh water diatom Gomphonema parvulum (Bacillariophyceae) produces the algal pheromones hormosirene 2 (C 11H 16) and dictyopterene A 16 (C 11H 18) from highly unsaturated eicosanoic acids like 20:5 ( ω−3) 21 and 20:4 ( ω−6) 14. The oxidative degradation is believed to proceed by cleavage of an intermediate 9-hydroperoxide like 6 by a hydroperoxide-lyase to yield 9-oxo-nona-(5 Z.7 E)-dienoic acid 8 and the corresponding C 11 hydrocarbon. The biosynthetic sequence is confirmed by identification and synthesis of the novel polar fatty acid fragment 8.
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