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Org Lett. 2003 Mar 20;5(6):885-7.

Production of octadienal in the marine diatom Skeletonema costatum.

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  • 1Istituto di Chimica Biomolecolare (ICB) del CNR, Via Campi Flegrei 34, 80078 Pozzuoli (Napoli), Italy.


[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.

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