Purpurogemutantin and Purpurogemutantidin, New Drimenyl Cyclohexenone Derivatives Produced by a Mutant Obtained by Diethyl Sulfate Mutagenesis of a Marine-Derived Penicillium purpurogenum G59
Two new drimenyl cyclohexenone derivatives, named purpurogemutantin (1) and purpurogemutantidin (2), and the known macrophorin A (3) were isolated from a bioactive mutant BD-1-6 obtained by random diethyl sulfate (DES) mutagenesis of a marine-derivedPenicillium purpurogenumG59. Structures and absolute configurations of1and2were determined by extensive spectroscopic methods, especially 2D NMR and electronic circular dichroism (ECD) analysis. Possible biosynthetic pathways for1–3were also proposed and discussed. Compounds1and2significantly inhibited human cancer K562, HL-60, HeLa, BGC-823 and MCF-7 cells, and compound3also inhibited the K562 and HL-60 cells. Both bioassay and chemical analysis (HPLC, LC-ESIMS) demonstrated that the parent strain G59 did not produce1–3, and that DES-induced mutation(s) in the mutant BD-1-6 activated some silent biosynthetic pathways in the parent strain G59, including one set for1–3production.Keywords:purpurogemutantin;purpurogemutantidin;sesquiterpene;meroterpenoid;structure determination;antitumor activity;Penicillium purpurogenum;marine-derived fungus;DES mutagenesis
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