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

doi:10.1016/j.bioorg.2020.103826

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

Bioorg Chem. 2020 Jun:99:103826. doi: 10.1016/j.bioorg.2020.103826. Epub 2020 Apr 6.

Authors

Wei Wang¹, Weiwei Wang², Haixia Ge³, Guolong Li⁴, Pingping Shen⁴, Shaohua Xu⁵, Boyang Yu⁴, Jian Zhang⁶

Affiliations

¹ State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of TCM Evaluation and Translational Research, China Pharmaceutical University, Nanjing 211198, PR China. Electronic address: 1721020352@stu.cpu.edu.cn.
² State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of TCM Evaluation and Translational Research, China Pharmaceutical University, Nanjing 211198, PR China. Electronic address: weiweiwang@cpu.edu.cn.
³ School of Life Sciences, Huzhou University, Huzhou 313000, PR China.
⁴ State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of TCM Evaluation and Translational Research, China Pharmaceutical University, Nanjing 211198, PR China.
⁵ College of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, PR China.
⁶ State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of TCM Evaluation and Translational Research, China Pharmaceutical University, Nanjing 211198, PR China. Electronic address: wilsonzhang99@cpu.edu.cn.

PMID: 32315895
DOI: 10.1016/j.bioorg.2020.103826

Abstract

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.

Keywords: Allylic oxidation; Bacillus megaterium; Biotransformation; Pentacyclic triterpenes; Δ(5)-steroids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Allyl Compounds / chemistry
Allyl Compounds / metabolism*
Bacillus megaterium / metabolism*
Hydroxylation
Molecular Conformation
Oxidation-Reduction
Steroids / chemistry
Steroids / metabolism*
Triterpenes / chemistry
Triterpenes / metabolism*

Substances

Allyl Compounds
Steroids
Triterpenes