Studies in the biochemistry of micro-organisms. 97. Flavipin, a crystalline metabolite of Aspergillus flavipes (Bainier & Sartory) Thom & Church and Aspergillus terreus Thom

Abstract

A hitherto undescribed mold metabolite, now named flavipin, has been isolated from culture filtrates of Aspergillus flavipes grown on Raulin-Thom solution and of A. terreus grown on Czapek-Dox solution. Flavipin, C9H8O5, forms pale-yellow rods, m.p. 233-234[degree] (decomp.). A number of its functional derivatives and degradation products are described, from the structures of which it is deduced that flavipin is l,2-diformyl-4,5,6-trihydroxy-3-methylbenzene. Flavipin is the 3rd mold metabolite to be described which is a substituted o-phthalaldehyde, the other 2 being gladiolic acid from Penicillium gladioli and cyclopaldic acid from P. cyclopium. All 3 substances are powerful antifungal agents. Flavipin is also a substituted pyrogallol, a class of compounds which occur only rarely as fungal metabolic products.