Sporidesmins. Part VI. Isolation and structure of dehydrogliotoxin a metabolite of Penicillium terlikowskii

Abstract

Pencillium terlikowskii(HLX 136) produced dehydrogliotoxin, C₁₃H₁₂N₂O₄S₂, when grown on defined media in surface culture. Sulphur, 1,2,3,4-tetrahydro-6-hydroxy-2-methyl-3-methylene-1,4-dioxopyrazino[1,2-a]-indole and the corresponding 1,3,4-trioxo-derivative were obtained when dehydrogliotoxin was treated with anhydrous acid. This reaction is analogous to known reactions in the sporidesmin series and it established both the presence of a 3,6-epidithia-2,5-dioxopiperazine system and the orientation of one hydroxyl group. The second hydroxyl group was shown to be located at position 3a by analysis of the nuclear magnetic resonance spectrum of the antibiotic.