Arsenic-containing ribofuranosides: isolation from brown kelp Ecklonia radiata and nuclear magnetic resonance spectra

Abstract

2-Hydroxy-3-sulphopropyl 5-deoxy-5-(dimethylarsinoyl)-β-ribofuranoside (1a) and 2,3-dihydroxypropyl 5-deoxy-5-(dimethylarsinoyl)-β-ribofuranoside (1b) have been isolated from the brown kelp Ecklonia radiata. Extraction of a second batch of Ecklonia yielded 3-‘glycerophosphoryl’-2-hydroxy-1-[5-deoxy-5-(dimethylarsinoyl)-β-ribofuranosyloxy] propane (1c) together with compound (1a). These compounds were identified chiefly by n.m.r. spectroscopy. N.m.r. data for the related (2S)-3-[5-deoxy-5-(dimethylarsinoyl)-β-D-ribofuranosyloxy]-2-hydroxypropyl hydrogen sulphate (1d), extracted [together with compound (1b)] from the giant clam Tridacna maxima, are presented also.