Biotransformation of Betulonic Acid by the Fungus Rhizopus arrhizus CGMCC 3.868 and Antineuroinflammatory Activity of the Biotransformation Products

Biotransformation of betulonic acid (1) by Rhizopus arrhizus CGMCC 3.868 resulted in the production of 16 new (3, 5, 6, and 9–21) and five known compounds. Structures of the new compounds were established by analysis of spectroscopic data. Hydroxylation, acetylation, oxygenation, glycosylation, and...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2021-10, Vol.84 (10), p.2664-2674
Main Authors: Song, Kai-Nan, Lu, You-Jia, Chu, Cheng-Jiao, Wu, Yan-Ni, Huang, Hui-Lian, Fan, Bo-Yi, Chen, Guang-Tong
Format: Article
Language:English
Subjects:
Acetylation
Animals
Anti-Inflammatory Agents - pharmacology
Biotransformation
Cell Line
Glycosylation
Hydroxylation
Mice
Molecular Structure
Neuroglia - drug effects
Nitric Oxide
Oleanolic Acid - analogs & derivatives
Oleanolic Acid - metabolism
Oleanolic Acid - pharmacology
Rhizopus oryzae - metabolism
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Summary:Biotransformation of betulonic acid (1) by Rhizopus arrhizus CGMCC 3.868 resulted in the production of 16 new (3, 5, 6, and 9–21) and five known compounds. Structures of the new compounds were established by analysis of spectroscopic data. Hydroxylation, acetylation, oxygenation, glycosylation, and addition reactions involved the C-20–C-29 double bond. Antineuroinflammatory activities of the obtained compounds in NO production were tested in lipopolysaccharides-induced BV-2 cells. Compared with the substrate betulonic acid, biotransformation products 3, 8, 9, 14, and 21 exhibited an improved inhibitory effect, with IC50 values of 10.26, 11.09, 5.38, 1.55, and 4.69 μM, lower than that of the positive control, N G-monomethyl-l-arginine.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.1c00480