Talarophenol Sulfate and Talarophilones from the Australian mud Dauber Wasp-associated Fungus, Talaromyces sp. CMB-W045

Abstract

Chemical analysis of a jasmine rice cultivation of an Australian mud dauber wasp-associated fungus, Talaromyces sp. CMB-W045, led to the discovery of a new p-terphenyl, talarophenol sulfate (1). The structure elucidation of 1 was achieved by detailed spectroscopic analysis supported by acid hydrolysis to the p-hydroquinone talarophenol (2), and subsequent in situ air oxidation to trace amounts of the p-quinone talaroquinone (3). The same jasmine rice cultivation also yielded the new talarophilones A (4) and B (5), and known (+)-mitorubrin (6) and pochonin D (7), with structures assigned by detailed spectroscopic analysis. Neither 1 or 4–7 exhibited growth inhibitory properties against a panel of human cell lines, or bacterial or fungal pathogens, although 1 did exhibit selective antibacterial activity against Streptococcus pyogenes ATCC 12344 (IC50 10 µM).