Oleanolic acid indole derivatives as novel α-glucosidase inhibitors: Synthesis, biological evaluation, and mechanistic analysis.

Dose-Response Relationship, Drug Glycoside Hydrolase Inhibitors / chemical synthesis Molecular Docking Simulation Molecular Structure Oleanolic Acid / chemical synthesis Saccharomyces cerevisiae / enzymology Structure-Activity Relationship alpha-Glucosidases / metabolism
Antidiabetic Benzene-ring-substituted indole Circular dichroism Docking Oleanolic acid α-glucosidase

Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
02 2021
Historique:
received: 01 12 2020
accepted: 20 12 2020
pubmed: 9 1 2021
medline: 7 9 2021
entrez: 8 1 2021
Statut: ppublish

Résumé

Research efforts have been directed to the development of oleanolic acid (OA) based α-glucosidase inhibitors and various OA derivatives showed improved anti-α-glucosidase activity. However, the inhibitory effects of indole infused OA derivatives on α-glucosidase is unknown. Herein, we synthesized a series of indole-OA (2a-2o) and -OA methyl ester (3a-3 l) derivatives with various electron withdrawing groups inducted to indole benzene ring and evaluated their anti-α-glucosidase activity. Indole OA derivatives (2a-2o) exhibited superior α-glucosidase inhibitory effects as compared to OA methyl ester derivatives (3a-3l) and OA (with IC

Identifiants

DOI: 10.1016/j.bioorg.2020.104580 PMID: 33418317
pubmed: 33418317
pii: S0045-2068(20)31878-2
doi: 10.1016/j.bioorg.2020.104580
pii:
doi:

Substances chimiques

Glycoside Hydrolase Inhibitors 0
Oleanolic Acid 6SMK8R7TGJ
alpha-Glucosidases EC 3.2.1.20

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

104580

Informations de copyright

Copyright © 2020 Elsevier Inc. All rights reserved.

Auteurs

Panpan Wu (P)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China; Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, United Kingdom.

Hao He (H)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China; Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA.

Hang Ma (H)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA.

Borong Tu (B)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Jiahao Li (J)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Shengzhu Guo (S)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Silin Chen (S)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Nana Cao (N)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Wende Zheng (W)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Xiaowen Tang (X)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Dongli Li (D)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Xuetao Xu (X)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Xi Zheng (X)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China.

Zhaojun Sheng (Z)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China. Electronic address: wyuchemszj@126.com.

Weiqian David Hong (W)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China; Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, United Kingdom. Electronic address: davidhwq@liverpool.ac.uk.

Kun Zhang (K)

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, PR China; International Healthcare Innovation Institute (Jiangmen), Jiangmen, 529040, PR China. Electronic address: kzhang@gdut.edu.cn.

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Classifications MeSH

questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes toxicologiques › Relation dose-effet des médicaments › Oleanolic acid indole derivatives as novel...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Hypoglycémiants › Inhibiteurs des glycoside hydrolases › Oleanolic acid indole derivatives as novel...
questionsmedicales.fr › Sciences de l'information › Méthodologies informatiques › Simulation numérique › Simulation de docking moléculaire › Oleanolic acid indole derivatives as novel...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Oleanolic acid indole derivatives as novel...
questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Terpènes › Triterpènes › Acide oléanolique › Oleanolic acid indole derivatives as novel...
questionsmedicales.fr › Eucaryotes › Champignons › Levures › Saccharomyces › Saccharomyces cerevisiae › Oleanolic acid indole derivatives as novel...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Oleanolic acid indole derivatives as novel...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Hydrolases › Glycosidases › Glucosidases › alpha-Glucosidase › Oleanolic acid indole derivatives as novel...