Isolation and identification of arsenic-containing ribofuranosides and inorganic arsenic from Japanese edible seaweed Hizikia fusiforme

Abstract
(2S)-3-[5-Deoxy-5-(dimethylarsinoyl)-β-D-ribofuranosyloxy]-2-hydroxypropyl hydrogen sulphate (1a), 3-[5-deoxy-5-(dimethylarsinoyl)-β-D-ribofuranosyloxy]-2-hydroxypropene-1-sulphonic acid (1b), 1-‘glycerophosphoryl’-2-hydroxy-3-[5-deoxy-5-(dimethylarsinoyl)-β-ribofuranosyloxy]propane (1c), and 2-amino-3-[5-deoxy-5-(dimethylarsinoyl)-β-D-ribofuranosyloxy]propene-1-sulphonic acid (1d), together with inorganic arsenic have been isolated from the edible seaweed Hizikia fusiforme. Structures have been determined chiefly by n.m.r. spectroscopy. Compound (1d) has not been reported previously. Compound (1b) is apparently present in Hizikia as a pair of C-2 diastereoisomers.