Constituents with potent α-glucosidase inhibitory activity from Pueraria lobata (Willd.) ohwi

[Display omitted] One new flavone hydrate named lobatflavate (1), one new chromone named lobatchrosin (2), and one new isoflavone named 3S,4R-tuberosin (3), along with four known isoflavone analogues (4–7), were isolated from the traditional Chinese medicinal plant of Pueraria lobata (Willd.) ohwi....

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Published in:Bioorganic & medicinal chemistry letters 2017-05, Vol.27 (9), p.1993-1998
Main Authors: Wang, Xiao-Ling, Jiao, Fu-Rong, Yu, Meng, Lin, Li-Bin, Xiao, Jian, Zhang, Qiang, Wang, Le, Duan, Dong-Zhu, Xie, Gang
Format: Article
Language:English
Subjects:
alpha-Glucosidases - metabolism
Chromone
Chromones - chemistry
Chromones - pharmacology
Drugs, Chinese Herbal - chemistry
Drugs, Chinese Herbal - pharmacology
Flavones
Flavones - chemistry
Flavones - pharmacology
Glycoside Hydrolase Inhibitors - chemistry
Glycoside Hydrolase Inhibitors - pharmacology
Humans
Hypoglycemic Agents - chemistry
Hypoglycemic Agents - pharmacology
Isoflavones
Isoflavones - chemistry
Isoflavones - pharmacology
Molecular Docking Simulation
Pueraria - chemistry
Pueraria lobata (Willd.) ohwi
Structure-Activity Relationship
α-Glucosidase inhibitor
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Summary:[Display omitted] One new flavone hydrate named lobatflavate (1), one new chromone named lobatchrosin (2), and one new isoflavone named 3S,4R-tuberosin (3), along with four known isoflavone analogues (4–7), were isolated from the traditional Chinese medicinal plant of Pueraria lobata (Willd.) ohwi. Their structures were elucidated by extensive spectroscopic methods of IR, UV, HR-ESI-MS, 1D and 2D NMR. The absolute configuration of 3 was determined by CD spectrum associated with TD-DFT calculation analysis. All compounds except for 2 were assayed the inhibitory activity against α-glucosidase. Every tested compound was proved to be more active than positive control of acarbose. Of which 1 and 4 showed significant activity with IC50 value of 1.79μM and 23.01μM (IC50 of acarbose was 1998.79μM). Enzyme kinetic experiments revealed that 1 was irreversible whereas 4 was reversible and non-competitive α-glucosidase inhibitors. Moreover, structure-activity relationship was discussed and the docking studies of 1, 3 and 4 were also carried out.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2017.03.013