Biocatalytic allylic hydroxylation of unsaturated triterpenes and steroids by Bacillus megaterium CGMCC 1.1741.

Wei Wang, Weiwei Wang, Haixia Ge, Guolong Li, Pingping Shen, Shaohua Xu, Boyang Yu, Jian Zhang

Bioorganic chemistry 2020 Jun

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In this study, we described the microbial catalyzed allylic oxidation by Bacillus megaterium CGMCC 1.1741 of three Δ12-pentacyclic triterpenes, erythrodiol (1), uvaol (2), hederagenin (3) and of four steroids including Δ5-steroids, diosgenin (4), pennogenin (5), 25(R,S)-ruscogenin (6) and Δ4-steroid, diosgenone (7). As a result, fourteen metabolites were generated with allyl hydroxyl moiety. Ten (1a-c, 2a, 2c, 3a, 5a-b, and 6a-b) of them were new natural products and their structures were determined on the basis of 1D/2D NMR and HR-MS data. Biocatalytic allylic oxidation by B. megaterium CGMCC 1.1741 is thus a potential non-toxic and efficient alternative method toward metal-mediated oxidation procedures in the synthesis of natural products and medicines. Copyright © 2020 Elsevier Inc. All rights reserved.

Citation

Wei Wang, Weiwei Wang, Haixia Ge, Guolong Li, Pingping Shen, Shaohua Xu, Boyang Yu, Jian Zhang. Biocatalytic allylic hydroxylation of unsaturated triterpenes and steroids by Bacillus megaterium CGMCC 1.1741. Bioorganic chemistry. 2020 Jun;99:103826