AmAT19, an acetyltransferase from Astragalus membranaceus, catalyses specific 6α-OH acetylation for tetracyclic triterpenes and steroids

Linlin Wang; Kuan Chen; Zilong Wang; Yang Yi; Meng Zhang; Aobulikasimu Hasan; Yi Kuang; Sharpkate Shaker; Rong Yu; Haotian Wang; Haiyang Liu; Min Ye; Xue Qiao

doi:10.1039/D1OB01106E

AmAT19, an acetyltransferase from Astragalus membranaceus, catalyses specific 6α-OH acetylation for tetracyclic triterpenes and steroids†

Linlin Wang,

^a Kuan Chen,

^a Zilong Wang,

^a Yang Yi,^a Meng Zhang,^a Aobulikasimu Hasan,^a Yi Kuang,^a Sharpkate Shaker,^a Rong Yu,^a Haotian Wang,^a Haiyang Liu,

^b Min Ye

*^a and Xue Qiao

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China
E-mail: yemin@bjmu.edu.cn, qiaoxue@bjmu.edu.cn

^b State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China

Abstract

Tetracyclic triterpenes and steroids are pharmacologically important molecules, and acetylation could improve their bioactivities. In this study, a highly regio- and stereo-specific acetyltransferase, AmAT19, was discovered from Astragalus membranaceus. AmAT19 could selectively catalyze the 6α-OH acetylation of four tetracyclic triterpenes and steroids. The strict selectivity is associated with different orientations of the 6α/β-OH as indicated by molecular docking. Acetylated products 1a, 3a and 4a remarkably increased the inhibitory activity against the 3-chymotrypsin-like protease (3CL^pro) of SARS-CoV-2, compared to 1, 3, and 4. AmAT19 could be a promising catalyst for specific 6α-OH acetylation to expand the molecular diversity of triterpenes and steroids.

This article is part of the themed collection: Chemical Biology in OBC

Organic & Biomolecular Chemistry

AmAT19, an acetyltransferase from Astragalus membranaceus, catalyses specific 6α-OH acetylation for tetracyclic triterpenes and steroids†

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AmAT19, an acetyltransferase from Astragalus membranaceus, catalyses specific 6α-OH acetylation for tetracyclic triterpenes and steroids

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