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Title: Microbial metabolism Part 14 Isolation and bioactivity evaluation of microbial metabolites of resveratrol

Author
item HERATH, WIMAL - University Of Mississippi
item KHAN, SHABANA - University Of Mississippi
item KHAN, IKHLAS - University Of Mississippi

Submitted to: Natural Product Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/12/2012
Publication Date: 9/6/2012
Citation: Herath, W., Khan, S.I., Khan, I.A. 2012. Microbial metabolism Part 14 Isolation and bioactivity evaluation of microbial metabolites of resveratrol. Natural Product Research. 32:1377-1382.

Interpretive Summary: Resveratrol (1) found in grapes, peanuts, cranberries and in several non-edible plants is associated with a wide array of biological properties including cardioprotective, anticarcinogenic, antioxidative, antiinflammatory and phytoestrogenic activities. It is shown that resveratrol is rapidly absorbed and metabolized to sulfates and glucuronides which predominantly circulate in plasma. The rapid conversion and elimination restrict bioavailability of 1 in vivo significantly cast doubts as to its relevance as a bioactive agent when considering the concentrations used in vitro studies. However, the possibility of deconjugation of resveratrol sulfates and glucronides to release the substrate to exert the biological activities at the target sites suggests that these metabolites could be the key determinants of its biological properties. In the present study, microbial models were used to obtain mammalian metabolites of resveratrol in sufficient quantities for further investigations. Fungi, Beauveria bassiana and Penicillium chrysogenium converted resveratrol to resveratrol-3-O-sulfate. The former, in addition, gave 5-methoxyresveratrol-3-O-ß-glucoside with the latter yielding 5-methoxyresveratrol-3-O-sulfate. The structures of the metabolites were determined by spectroscopic methods. Evaluation of biological activity of metabolites through a series of mammalian cell based assays indicated that resveratrol tends to lose its anti-inflammatory, cytotoxic and antioxidant activities with the substitution of its hydroxyl groups.

Technical Abstract: The fungi, Beauveria bassiana (ATCC 13144) and Penicillium chrysogenium (ATCC 9480) transformed resveratrol (1) to resveratrol-3-O-sulfate (4). The former, in addition, gave 5-methoxyresveratrol-3-O-ß-glucoside (2) with the latter yielding 5-methoxyresveratrol-3-O-sulfate (3). The structures were established by spectroscopic methods. Evaluation of biological activity of metabolites through a series of mammalian cell based assays indicated that resveratrol tends to lose its anti-inflammatory, cytotoxic and antioxidant activities with the substitution of its hydroxyl groups.