Synthesis and Evaluation of Coumarin-Chalcone Derivatives as α-Glucosidase Inhibitors

Coumarin and chalcone, two important kinds of natural product skeletons, both exhibit α-glucosidase inhibitory activity. In this work, coumarin-chalcone derivatives 3 ( a∼v ) were synthesized, and their α-glucosidase inhibitory activity was screened. The results showed that all synthetic derivatives...

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Published inFrontiers in chemistry Vol. 10; p. 926543
Main Authors Hu, Chun-Mei, Luo, Yong-Xin, Wang, Wen-Jing, Li, Jian-Ping, Li, Meng-Yue, Zhang, Yu-Fei, Xiao, Di, Lu, Li, Xiong, Zhuang, Feng, Na, Li, Chen
Format Journal Article
LanguageEnglish
Published Frontiers Media S.A 27.06.2022
Subjects
chalcone
Chemistry
coumarin
docking
enzyme inhibitor
α-glucosidase
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Abstract Coumarin and chalcone, two important kinds of natural product skeletons, both exhibit α-glucosidase inhibitory activity. In this work, coumarin-chalcone derivatives 3 ( a∼v ) were synthesized, and their α-glucosidase inhibitory activity was screened. The results showed that all synthetic derivatives (IC 50 : 24.09 ± 2.36 to 125.26 ± 1.18 μM) presented better α -glucosidase inhibitory activity than the parent compounds 3-acetylcoumarin (IC 50 : 1.5 × 10 5  μM) and the positive control acarbose (IC 50 : 259.90 ± 1.06 μM). Among them, compound 3t displayed the highest α -glucosidase inhibitory activity (IC 50 : 24.09 ± 2.36 μM), which was approximately 10 times stronger than that of acarbose. The kinetic assay of 3t ( K I = 18.82 μM, K IS = 59.99 μM) revealed that these compounds inhibited α-glucosidase in a mixed-type manner. Molecular docking was used to simulate the interaction between α-glucosidase and compound 3t .
AbstractList Coumarin and chalcone, two important kinds of natural product skeletons, both exhibit α-glucosidase inhibitory activity. In this work, coumarin-chalcone derivatives 3 ( a∼v ) were synthesized, and their α-glucosidase inhibitory activity was screened. The results showed that all synthetic derivatives (IC 50 : 24.09 ± 2.36 to 125.26 ± 1.18 μM) presented better α -glucosidase inhibitory activity than the parent compounds 3-acetylcoumarin (IC 50 : 1.5 × 10 5  μM) and the positive control acarbose (IC 50 : 259.90 ± 1.06 μM). Among them, compound 3t displayed the highest α -glucosidase inhibitory activity (IC 50 : 24.09 ± 2.36 μM), which was approximately 10 times stronger than that of acarbose. The kinetic assay of 3t ( K I = 18.82 μM, K IS = 59.99 μM) revealed that these compounds inhibited α-glucosidase in a mixed-type manner. Molecular docking was used to simulate the interaction between α-glucosidase and compound 3t .
Coumarin and chalcone, two important kinds of natural product skeletons, both exhibit α-glucosidase inhibitory activity. In this work, coumarin-chalcone derivatives 3 (a∼v) were synthesized, and their α-glucosidase inhibitory activity was screened. The results showed that all synthetic derivatives (IC50: 24.09 ± 2.36 to 125.26 ± 1.18 μM) presented better α-glucosidase inhibitory activity than the parent compounds 3-acetylcoumarin (IC50: 1.5 × 105 μM) and the positive control acarbose (IC50: 259.90 ± 1.06 μM). Among them, compound 3t displayed the highest α-glucosidase inhibitory activity (IC50: 24.09 ± 2.36 μM), which was approximately 10 times stronger than that of acarbose. The kinetic assay of 3t (KI = 18.82 μM, KIS = 59.99 μM) revealed that these compounds inhibited α-glucosidase in a mixed-type manner. Molecular docking was used to simulate the interaction between α-glucosidase and compound 3t.
Author Li, Chen
Zhang, Yu-Fei
Li, Meng-Yue
Feng, Na
Xiao, Di
Wang, Wen-Jing
Luo, Yong-Xin
Li, Jian-Ping
Hu, Chun-Mei
Xiong, Zhuang
Lu, Li
AuthorAffiliation School of Biotechnology and Health Sciences , Wuyi University , Jiangmen , China
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Edited by: Xi Zheng, Rutgers, The State University of New Jersey, United States
Ren Qinggang, Guangdong University of Petrochemical Technology, China
Yushui Bi, Shandong First Medical University, China
These authors have contributed equally to this work
This article was submitted to Organic Chemistry, a section of the journal Frontiers in Chemistry
Reviewed by: Chaoqun Li, Shaanxi Normal University, China
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  contributor:
    fullname: Rocha
– volume: 72
  start-page: 228
  year: 2017
  ident: B31
  article-title: Discovery of 3,3-Di(indolyl)indolin-2-One as a Novel Scaffold for α-glucosidase Inhibitors: In Silico Studies and SAR Predictions
  publication-title: Bioorg. Chem.
  doi: 10.1016/j.bioorg.2017.05.006
  contributor:
    fullname: Wang
SSID ssj0001213420
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Snippet Coumarin and chalcone, two important kinds of natural product skeletons, both exhibit α-glucosidase inhibitory activity. In this work, coumarin-chalcone...
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StartPage 926543
SubjectTerms chalcone
Chemistry
coumarin
docking
enzyme inhibitor
α-glucosidase
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Title Synthesis and Evaluation of Coumarin-Chalcone Derivatives as α-Glucosidase Inhibitors
URI https://search.proquest.com/docview/2689672078
https://pubmed.ncbi.nlm.nih.gov/PMC9271751
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