AS2077715: a novel antifungal antibiotic produced by Capnodium sp. 339855

Abstract

A novel antifungal agent, AS2077715, was isolated from the fermentation broth of a fungal strain (339855) identified as a new Capnodium species based on morphological characteristics and large-subunit ribosomal DNA sequencing. AS2077715 was isolated as a white powder via solvent extraction, HP-20 and ODS-B column chromatography and crystallization, and was determined to have the molecular formula C25H41NO7. AS2077715 has a structure related to that of funiculosin, an inhibitor of mitochondrial cytochrome bc1 complex (complex III), and showed antifungal activity against Trichophyton species.

Biosynthesis of AS2077715 and Funiculosin: Pathway Reconstitution and Identification of Enzymes that Form the All-cis Cyclopentanetetraol Moiety

“…A remarkable example of aromatic dearomatization and ring contraction is seen in the fungal natural products AS2077715 ( 1 ) and funiculosin ( 2 ), isolated from Capnodium sp. 339855 and Penicillium funicolosum, respectively. Both compounds show significant antifungal activity by inhibiting mitochondrial cytochrome bc 1 complex. , The defining structural feature of 1 and 2 is the all- cis cyclopentanetetraol moiety that is connected to the 5-position of a N- methyl-3-pyranyl-4-hydroxy-2-pyridone.…”

“…A remarkable example of aromatic dearomatization and ring contraction is seen in the fungal natural products AS2077715 (1) and funiculosin (2), isolated from Capnodium sp. 339855 15 and Penicillium funicolosum, 16 respectively. Both compounds show significant antifungal activity by inhibiting mitochondrial cytochrome bc 1 complex.…”