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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 Publication | CHINESE CHEMICAL LETTERS |
ISSN | 1001-8417 |
Volume | 32Issue:3Pages:1202-1205 |
Abstract | 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 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. |
Keyword | Amomum tsao-ko Zingiberaceae Flavanol-monoterpenoid hybrids alpha-Glucosidase inhibitors ANTIOXIDANT ACTIVITY ESSENTIAL OIL CONSTITUENTS CREVOST |
DOI | 10.1016/j.cclet.2020.08.050 |
WOS ID | WOS:000642399500014 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.kib.ac.cn/handle/151853/73676 |
Collection | 中国科学院昆明植物研究所 |
Affiliation | 1.[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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