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Production of Octadienal in the Marine Diatom Skeletonema costatum

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Istituto di Chimica Biomolecolare (ICB) del CNR, Via Campi Flegrei 34, 80078 Pozzuoli (Napoli), Italy, Stazione Zoologica “A. Dohrn”, Villa comunale, 80121 Napoli, Italy, and Dipartimento di Chimica, Facoltà di Scienze, University of Salerno, Via S. Allende, 84041 Baronissi (Salerno), Italy
Cite this: Org. Lett. 2003, 5, 6, 885–887
Publication Date (Web):February 25, 2003
https://doi.org/10.1021/ol034057c
Copyright © 2003 American Chemical Society
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    Marine diatoms produce α,β,γ,δ-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 C16 fatty acids.

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    NMR and MS spectra of the biosynthetic precursor and target compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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