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Tsaokols A and B, unusual flavanol-monoterpenoid hybrids as alpha-glucosidase inhibitors from Amomum tsao-ko
He,Xiao-Feng; Chen,Ji-Jun; Li,Tian-Ze; Hu,Jing; Zhang,Xu-Ke; Guo,Yuan-Qiang; Zhang,Xue-Mei; Geng,Chang-An
2021
Source PublicationCHINESE CHEMICAL LETTERS
ISSN1001-8417
Volume32Issue:3Pages:1202-1205
AbstractTsaokols 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 alpha-glucosidase inhibitory activity with IC50 values of 18.8 and 38.6 mu mol/L (acarbose, IC50 = 213 mu mol/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. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
KeywordAmomum tsao-ko Zingiberaceae Flavanol-monoterpenoid hybrids alpha-Glucosidase inhibitors ANTIOXIDANT ACTIVITY ESSENTIAL OIL CONSTITUENTS CREVOST
DOI10.1016/j.cclet.2020.08.050
WOS IDWOS:000642399500014
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Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/73676
Collection中国科学院昆明植物研究所
Affiliation1.[He, Xiao-Feng
2.Chen, Ji-Jun
3.Li, Tian-Ze
4.Hu, Jing
5.Zhang, Xue-Mei
6.Chinese Acad Sci, Yunnan Key Lab Nat Med Chem, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
7.[Zhang, Xu-Ke
8.Nankai Univ, Coll Pharm, Tianjin 300071, Peoples R China
9.Nankai Univ, Tianjin Key Lab Mol Drug Res, Tianjin 300071, Peoples R China
10.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
He,Xiao-Feng,Chen,Ji-Jun,Li,Tian-Ze,et al. Tsaokols A and B, unusual flavanol-monoterpenoid hybrids as alpha-glucosidase inhibitors from Amomum tsao-ko[J]. CHINESE CHEMICAL LETTERS,2021,32(3):1202-1205.
APA He,Xiao-Feng.,Chen,Ji-Jun.,Li,Tian-Ze.,Hu,Jing.,Zhang,Xu-Ke.,...&Geng,Chang-An.(2021).Tsaokols A and B, unusual flavanol-monoterpenoid hybrids as alpha-glucosidase inhibitors from Amomum tsao-ko.CHINESE CHEMICAL LETTERS,32(3),1202-1205.
MLA He,Xiao-Feng,et al."Tsaokols A and B, unusual flavanol-monoterpenoid hybrids as alpha-glucosidase inhibitors from Amomum tsao-ko".CHINESE CHEMICAL LETTERS 32.3(2021):1202-1205.
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