Novel polyunsaturated n-alkenes in the marine diatom Rhizosolenia setigera

Abstract

Four previously unknown n-C25 and n-C27 heptaenes of the marine diatom Rhizosolenia setigera were isolated and identified using NMR spectroscopy. They possess six methylene interrupted (Z)-double bonds starting at C-3 and an additional terminal or n-2 (Z)-double bond. Structural and stable carbon isotopic evidence suggests that these polyenes are biosynthesized by chain elongation of the C22:6n-3 fatty acid, followed by decarboxylation and introduction of double bonds at specific positions.