Constituents with potent α-glucosidase inhibitory activity from Pueraria lobata (Willd.) ohwi.
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 IC50value of 1.79μM and 23.01μM (IC50of 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.
Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, Shaanxi, PR China. Electronic address: xlwangwang@163.com.
Xiao-Ling
XL
Wang
Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, Shaanxi, PR China.
Fu-Rong
FR
Jiao
College of Chemistry & Materials Science, Northwest University, Xi'an 710062, Shaanxi, PR China.
Meng
M
Yu
Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, Shaanxi, PR China.
Li-Bin
LB
Lin
Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, Shaanxi, PR China. Electronic address: xjxs163@126.com.
Jian
J
Xiao
College of Science, Northwest A&F University, Yangling 712100, Shaanxi, PR China.
Qiang
Q
Zhang
Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, Shaanxi, PR China.
Le
L
Wang
Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, Shaanxi, PR China.
Dong-Zhu
DZ
Duan
College of Chemistry & Materials Science, Northwest University, Xi'an 710062, Shaanxi, PR China.
Gang
G
Xie
D002867:Chromones / Q000737:chemistry / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000494:pharmacology*; D047309:Flavones / Q000737:chemistry / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D007004:Hypoglycemic Agents / Q000737:chemistry / Q000494:pharmacology; D007529:Isoflavones / Q000737:chemistry / Q000494:pharmacology; D062105:Molecular Docking Simulation; D029908:Pueraria / Q000737:chemistry*; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000378:metabolism
D002867:Chromones; D004365:Drugs, Chinese Herbal; D047309:Flavones; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents; D007529:Isoflavones; D000520:alpha-Glucosidases
Chromone; Flavones; Isoflavones; Pueraria lobata (Willd.) ohwi.; α-Glucosidase inhibitor