Miniolins A–C, novel isomeric furanones induced by epigenetic manipulation of Penicillium minioluteum

Abstract

Cultivation of Penicillium minioluteum with azacitidine, a DNA methyltransferase inhibitor, led to the isolation of a novel type of aspertetronin dimer, named miniolins A–C (1–3), along with their precursor aspertetronin A (4). The structures of 1–3 were elucidated by extensive spectroscopic methods, and the absolute configurations were assigned by the chiral HPLC analysis of chemical degradation products and electronic circular dichroism associated with the TDDFT computational method (CAM-B3LYP/TZVP). The miniolins showed moderate cytotoxic activity against Hela cell lines.