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Paper | Regular issue | Vol 91, No. 2, 2015, pp.265-274
Published online, 23rd January, 2015
DOI: 10.3987/COM-14-13132
Iriomoteolide-2a, a Cytotoxic 23-Membered Macrolide from Marine Benthic Dinoflagellate Amphidinium Species

Keiko Kumagai, Masashi Tsuda,* Atsunori Masuda, Eri Fukushi, and Jun Kawabata

*Center for Advanced Marine Core Research , Kochi University, Nankoku, Kochi 783-8502, Japan

Abstract

The first 23-membered macrolide, iriomoteolide-2a (1), was isolated from cultivated algal cells of a marine benthic dinoflagellate Amphidinium species. The structure was determined based on detailed analysis of 2D NMR data. The relative stereochemistries were assigned on the basis of coupling constants and ROESY data, and the absolute configurations were elucidated by analyzing the NMR data of the MTPA esters for 1 and its reduced product. Iriomoteolide-2a (1) exhibited potent cytotoxic activities in vitro and in vivo.