Abstract
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-derived Penicillium purpurogenum G59. Structures and absolute configurations of 1 and 2 were determined by extensive spectroscopic methods, especially 2D NMR and electronic circular dichroism (ECD) analysis. Possible biosynthetic pathways for 1–3 were also proposed and discussed. Compounds 1 and 2 significantly inhibited human cancer K562, HL-60, HeLa, BGC-823 and MCF-7 cells, and compound 3 also inhibited the K562 and HL-60 cells. Both bioassay and chemical analysis (HPLC, LC-ESIMS) demonstrated that the parent strain G59 did not produce 1–3, 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 for 1–3 production.
Highlights
Meroterpenoids, generally occurring in nature, display a huge range of structural diversity with a broad spectrum of important biological activities [1]
Bioassay-guided column chromatography of the extract delivered active fractions, which were subjected to a semi-preparative HPLC separation to afford bioactive metabolites 1–3
122–123 °C, [α] D +21.0 (c 1.0, MeOH), and its molecular formula C24H34O6 was determined by HRESIMS (m/z 419.2431 [M + H]+; Δ = +0.3 mmu)
Summary
Meroterpenoids, generally occurring in nature, display a huge range of structural diversity with a broad spectrum of important biological activities [1]. We have reported a new and simple approach to activate the dormant secondary metabolite production by introducing gentamicin resistance in P. purpurogenum G59 [44] Using this method, we obtained nine antitumor mutants from strain G59 [44], and several antitumor secondary metabolites newly produced by two bioactive mutants were explored previously [44,45]. The isolation, structure elucidation, cytotoxicity assay, and HPLC and LC-ESIMS analysis for 1–3 are reported in detail in this paper
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