Induced production of a new polyketide in <i>Penicillium</i> sp. HS-11 by chemical epigenetic manipulation

Abstract

Chemical investigation into the culture broth of the plant endophyte <i>Penicillium</i> sp. HS-11 in the modified Martin's medium supplemented with subemylanilide hydroxamic acid (SAHA), a well-known histone deacetylase (HDACs) inhibitor, led to the isolation and identification of two induced products 4-epipenicillone B (<b>1</b>) and (<i>R</i>)-(+)-chrysogine (<b>2</b>). 4-epipenicillone B (<b>1</b>) was obtained as a new compound whose structure was elucidated by comprehensive spectroscopic methods including 1 D/2D NMR, HRESMS, and quantum chemistry calculations including DFT GIAO ¹³C NMR and ECD calculation. Acquisition of 4-epipenicillone B (<b>1</b>) enriched the chemical diversities of fungal natural products possessing a tricyclo [5.3.1.0^3,8] undecane skeleton. The cytotoxic activity of <b>1</b> was also evaluated.