The structure of dermocybin

Abstract

1. Dermocybin, a metabolite of the fungus Cortinarius sanguineus, is a tetrahydroxymethoxy-2-methylanthraquinone in which 3 of the hydroxyl groups are in the [alpha] -position and one hydroxyl and the methoxyl group are in the [beta]-position in the anthraquinone nucleus. To elucidate the structure of nordermocybin, l4:5:6:7-pentahydroxy-2-methyl-, l:4:6:7:8-pentahydroxy-2-methyl-, 4:5:6:7:8-pentahydroxy-and 4:5:6:7:8-pentahydroxy-2-methyl-anthraquinone were synthesized. Nordermocybin is identical with 4:5:6:7:8-pentahydroxy-2-methylantra-quinone. Dermocybin has therefore the structure 4:5:6:8-tetrahydroxy-7-methoxy-2-methylanthraquinone or 4:5:7:8-tetrahydroxy-6-methoxy-2 -methylanthraquinone.