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Design, synthesis and α-glucosidase inhibition study of novel embelin derivatives.

ABSTRACT: Embelin is a naturally occurring para-benzoquinone isolated from Embelia ribes (Burm. f.) of the Myrsinaceae family. It was first discovered to have potent inhibitory activity (IC₅₀ = 4.2 μM) against α-glucosidase in this study. Then, four series of novel embelin derivatives were designed, prepared and evaluated in α-glucosidase inhibition assays. The results show that most of the embelin derivatives synthesised are effective α-glucosidase inhibitors, with IC₅₀ values at the micromolar level, especially 10d, 12d, and 15d, the IC₅₀ values of which are 1.8, 3.3, and 3.6 μM, respectively. Structure-activity relationship (SAR) studies suggest that hydroxyl groups in the 2/5-position of para-benzoquinone are very important, and long-chain substituents in the 3-position are highly preferred. Moreover, the inhibition mechanism and kinetics studies reveal that all of 10d, 12d, 15d, and embelin are reversible and mixed-type inhibitors. Furthermore, docking experiments were carried out to study the interactions between 10d and 15d with α-glucosidase.

SUBMITTER: Chen X

PROVIDER: S-EPMC7006637 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Design, synthesis and α-glucosidase inhibition study of novel embelin derivatives.

Chen Xiaole X Gao Min M Jian Rongchao R Hong Weiqian David WD Tang Xiaowen X Li Yuling Y Zhao Denggao D Zhang Kun K Chen Wenhua W Zheng Xi X Sheng Zhaojun Z Wu Panpan P

Journal of enzyme inhibition and medicinal chemistry 20201201 1

Embelin is a naturally occurring para-benzoquinone isolated from Embelia ribes (Burm. f.) of the Myrsinaceae family. It was first discovered to have potent inhibitory activity (IC50 = 4.2 μM) against α-glucosidase in this study. Then, four series of novel embelin derivatives were designed, prepared and evaluated in α-glucosidase inhibition assays. The results show that most of the embelin derivatives synthesised are effective α-glucosidase inhibitors, with IC50</sub ...[more]

PMID: 31969031

Dataset Information

Design, synthesis and α-glucosidase inhibition study of novel embelin derivatives.

Publications

Design, synthesis and α-glucosidase inhibition study of novel embelin derivatives.

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