Organic Letters 2003-03-20

Production of octadienal in the marine diatom Skeletonema costatum.

Giuliana D'Ippolito, Giovanna Romano, Tonino Caruso, Aldo Spinella, Guido Cimino, Angelo Fontana

Index: Org. Lett. 5(6) , 885-7, (2003)

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Abstract

[reaction: see text] Marine diatoms produce alpha,beta,gamma,delta-unsaturated aldehydes that have detrimental effects on the reproduction of their natural predators. The production of these defensive metabolites is suggested to involve enzymatic oxidation of polyunsaturated fatty acids. In this paper, feeding experiments with labeled precursor provide clear evidence in support of the origin of octadienals 1 and 2 from 6,9,12-hexadecatrienoic acid (5), thus proving the involvement of novel lipoxygenase/lyase activity for the oxidation of C(16) fatty acids.