Amphidinolide X, a Novel 16-Membered Macrodiolide from Dinoflagellate Amphidinium sp.

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Abstract
A novel cytotoxic 16-membered macrodiolide, amphidinolide X (1), has been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42). The gross structure of 1 was elucidated on the basis of spectroscopic data including one-bond and long-range 13C−13C correlations. The relative and absolute stereochemistries were determined by combined analyses of NOESY data and 1H−1H and 1H−13C coupling constants of 1 and NMR data of the degradation products. Amphidinolide X (1) is the first macrodiolide consisting of polyketide-derived diacid and diol units from natural sources. The biosynthetic origins of 1 were investigated by means of feeding experiments with 13C-labeled acetates.