Synthesis, α-Glucosidase inhibition and molecular docking studies of tyrosol derivatives

To find a potent α-glucosidase inhibitor, 24 tyrosol derivatives with different substituents located at the meta, ortho, or para position of the phenyl group have been synthesised via the Mitsunobu reaction, characterised by 1 H NMR, 13 C NMR, ESI-MS and IR and evaluated for inhibition. The derivati...

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Bibliographic Details
Published in:Natural product research 2021-05, Vol.35 (10), p.1596-1604
Main Authors: Zhang, Luyun, Xu, Qian, Zhu, Junyi, Xia, Guangqing, Zang, Hao
Format: Article
Language:English
Subjects:
Acarbose
Binding
Chemical synthesis
Glucosidase
Molecular docking
NMR
Nuclear magnetic resonance
structure activity relationship
synthesis
Tyrosol
α-Glucosidase
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Summary:To find a potent α-glucosidase inhibitor, 24 tyrosol derivatives with different substituents located at the meta, ortho, or para position of the phenyl group have been synthesised via the Mitsunobu reaction, characterised by 1 H NMR, 13 C NMR, ESI-MS and IR and evaluated for inhibition. The derivatives possessed varying degrees of in vitro inhibitory activity against α-glucosidase and a relationship between the structure and activity was subsequently established for all compounds. Two of these compounds with substituents at the para position showed significant inhibitory effects surpassing that of the control standard acarbose. Molecular docking studies performed to better understand the binding interactions between the enzyme and the two most active compounds showed substantial binding within the active site of α-glucosidase. Taken together, these results indicate that the position of the substituent plays a crucial role in this inhibition and may facilitate the development of new α-glucosidase inhibitors.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2019.1628750