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Pure Appl. Chem., 2007, Vol. 79, No. 4, pp. 481-490

Chemistry of oxylipin pathways in marine diatoms

Angelo Fontana1, Giuliana d'Ippolito1, Adele Cutignano1, Antonio Miralto2, Adrianna Ianora2, Giovanna Romano2 and Guido Cimino1

1 Istituto di Chimica Biomolecolare, CNR, Via Campi Flegrei 34, 80078, Pozzuoli (Napoli), Italy
2 Stazione Zoologica "A. Dohrn", Villa Comunale, 80121 Napoli, Italy

Abstract: Oxylipins are important signal transduction molecules widely distributed in animals and plants where they regulate a variety of events associated with physiological and pathological processes. The family embraces several different metabolites that share a common origin from the oxygenase-catalyzed oxidation of polyunsaturated fatty acids. The biological role of these compounds has been especially studied in mammalians and higher plants, although a varied and very high concentration of these products has also been reported from marine macroalgae. This article gives a summary of our results concerning the oxylipin chemistry of marine diatoms, a major class of planktonic microalgae that discourage predation from their natural grazers, zooplanktonic copepods, using chemical warfare. These apparently harmless microscopic cells produce a plethora of oxylipins, including short-chain unsaturated aldehydes, hydroxyl-, keto-, and epoxyhydroxy fatty acid derivatives, that induce reproductive failure in copepods through abortions, congenital malformations, and reduced larval growth. The biochemical process involved in the production of these compounds shows a simple regulation based on decompartmentation and mixing of preexisting enzymes and requires hydrolysis of chloroplast-derived glycolipids to feed the downstream activities of C16 and C20 lipoxygenases.