Bioactive Polyhydroxanthones from Penicillium purpurogenum
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Published on: August 31, 2015
Jinghua Xue1, Hanxiang Li1, Ping Wu1
1Key Laboratory of Plant Resources Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
Abstract:
Eight new polyhydroxanthones, penicixanthones A-H (1-8), including four monomers (1-4) and four dimers (5-8), were isolated from solid cultures of Penicillium purpurogenum SC0070. Their structures were elucidated by extensive spectroscopic analysis, X-ray single-crystal diffraction, and theoretical computations of ECD spectra. Penicixanthone B (2) has a hexahydroxanthone structure featuring an unusual oxygen bridge between C-6 and C-8a. Penicixanthone D (4) is distinct from other penicixanthones in stereochemistry, and its biosynthetic mechanism was proposed based on theoretical simulations for the reaction pathway of C-10a epimerization. Penicixanthone G (6) exhibited the most potent cytotoxicity (IC50: 0.3-0.6 μM) when tested against human carcinoma A549, HeLa, and HepG2 cells, whereas it was nontoxic to the normal Vero cells (IC50 > 50 μM). It also displayed the strongest antibacterial activity (MIC: 0.4 μg/mL) against both Staphylococcus aureus and the methicillin-resistant strain MRSA.
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