Citation: Xiao-Feng He, Ji-Jun Chen, Tian-Ze Li, Jing Hu, Xu-Ke Zhang, Yuan-Qiang Guo, Xue-Mei Zhang, Chang-An Geng. Tsaokols A and B, unusual flavanol-monoterpenoid hybrids as α-glucosidase inhibitors from Amomum tsao-ko[J]. Chinese Chemical Letters, ;2021, 32(3): 1202-1205. doi: 10.1016/j.cclet.2020.08.050 shu

Tsaokols A and B, unusual flavanol-monoterpenoid hybrids as α-glucosidase inhibitors from Amomum tsao-ko

Xiao-Feng He ^{a, c} ,
Ji-Jun Chen ^{a, c} ,
Tian-Ze Li ^a ,
Jing Hu ^a ,
Xu-Ke Zhang ^b ,
Yuan-Qiang Guo ^b ,
Xue-Mei Zhang ^a ,
Chang-An Geng ^{a, *,}

a.
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, China
b.
College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

gengchangan@mail.kib.ac.cn

Received Date: 10 June 2020
Revised Date: 1 August 2020
Accepted Date: 30 August 2020
Available Online: 4 September 2020

Figures(3)

Tsaokols A (1) and B (2), two complicated flavanol-monoterpenoid hybrids, were isolated from the dried fruits of Amomum tsao-ko under the guidance of LCMS and bioassay. Their structures were determined by extensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 shared a flavanol backbone fused with 5/7 and 5/6 bicyclic monoterpenoid scaffolds, which were biogenetically condensed by Michael addition and acetalization. Compounds 1 and 2 exhibited significant α-glucosidase inhibitory activity with IC₅₀ values of 18.8 and 38.6 μmol/L (acarbose, IC₅₀ = 213 μmol/L). Docking study supported the strong interactions of 1 and 2 bonding with enzyme by mainly hydrophobic and hydrogen-bond effects. Compounds 1 and 2 could be fast distinguished by the diagnostic ions at m/z 289 and 313 in negative MS² experiments.
- Amomum tsao-ko,
- Zingiberaceae,
- Flavanol-monoterpenoid hybrids,
- α-Glucosidase inhibitors
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