Microbial Transformation of Terreusinone, an Ultraviolet-A (UV-A) Protecting Dipyrroloquinone, by Streptomyces sp.

Abstract

Biotransformation study was conducted on the marine dipyrroloquinone, terreusinone (1) isolated from the marine-derived fungus Aspergillus terreus. Preparative-scale fermentation of terreusinone with Streptomyces sp. has resulted in the isolation of a new oxidized metabolite, terreusinol (2). The structure was elucidated as 2-[(1R)-1-hydroxyisobutyl]-6-[(1R)-1,2-dihydroxyisobutyl]-1H,5H-pyrrolo[2,3-b]indole-4,8-dione (2) on the basis of physicochemical evidence. Terreusinol (2) showed an ultraviolet-A (UV-A) (320—390 nm) protecting activity with ED₅₀ values of 150 μM, which is more active than oxybenzone (ED₅₀, 350 μM) currently being used as sunscreen.