Amomutsaokols A-K, diarylheptanoids from Amomum tsao-ko and their α-glucosidase inhibitory activity

Xiao-Feng He; Hui-Mei Wang; Chang-An Geng; Jing Hu; Xue-Mei Zhang; Yuan-Qiang Guo; Ji-Jun Chen

doi:10.1016/j.phytochem.2020.112418

Amomutsaokols A-K, diarylheptanoids from Amomum tsao-ko and their α-glucosidase inhibitory activity

Phytochemistry. 2020 Sep:177:112418. doi: 10.1016/j.phytochem.2020.112418. Epub 2020 Jul 15.

Authors

Xiao-Feng He¹, Hui-Mei Wang², Chang-An Geng³, Jing Hu³, Xue-Mei Zhang³, Yuan-Qiang Guo², Ji-Jun Chen⁴

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, PR China; University of Chinese Academy of Sciences, Beijing, 100049, PR China.
² College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin, 300071, PR China.
³ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, PR China.
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, PR China; University of Chinese Academy of Sciences, Beijing, 100049, PR China. Electronic address: chenjj@mail.kib.ac.cn.

PMID: 32679346
DOI: 10.1016/j.phytochem.2020.112418

Abstract

Eleven undescribed diarylheptanoids, amomutsaokols A‒K (1-11), together with 13 known ones (13-24), were isolated from the active fraction of the fruits of Amomum tsao-ko. The structures of the undescribed compounds were determined by extensive 1D and 2D NMR, HRESIMS and ECD calculations. Compounds 3-5, 7, 8, 12, 14 and 19 showed obviously α-glucosidase inhibitory activity with IC₅₀ values ranging from 12.9 to 48.8 μM. An enzyme kinetic analysis indicated that compounds 8 and 9 were α-glucosidase noncompetitive inhibitors with K_i values of 18.5 and 213.0 μM, respectively. This study supported diarylheptanoids as the active constituents of A. tsao-ko with α-glucosidase inhibitory effects.

Keywords: Amomum tsao-ko; Amomutsaokols A‒K; Diarylheptanoids; α-Glucosidase inhibitory activity.

MeSH terms

Amomum*
Diarylheptanoids*
Glycoside Hydrolase Inhibitors
Kinetics
alpha-Glucosidases

Substances

Diarylheptanoids
Glycoside Hydrolase Inhibitors
alpha-Glucosidases