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Molecules 2015, 20(9), 17016-17040; doi:10.3390/molecules200917016

Synthesis and Biological Activity of Isoflavone Derivatives from Chickpea as Potent Anti-Diabetic Agents

1
School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100029, China
2
Health Cultivation Laboratory of the Ministry of Education, Beijing University of Chinese Medicine, Beijing 100029, China
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 20 July 2015 / Revised: 30 August 2015 / Accepted: 3 September 2015 / Published: 17 September 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [9651 KB, uploaded 17 September 2015]   |  

Abstract

A set of novel isoflavone derivatives from chickpea were synthesized. The structures of derivatives were identified by proton nuclear magnetic resonance (1H-NMR), carbon-13 (13C)-NMR and mass spectrometry (MS) spectral analyses. Their anti-diabetic activities were evaluated using an insulin-resistant (IR) HepG2 cell model. Additionally, the structure-activity relationships of these derivatives were briefly discussed. Compounds 1c, 2h, 3b, and 5 and genistein exhibited significant glucose consumption-enhancing effects in IR-HepG2 cells. In addition, the combinations of genistein, 2h, and 3b (combination 6) and of 3b, genistein, and 1c (combination 10) exhibited better anti-diabetic activity than the individual compounds. At the same dosage, there was no difference in effect between the combination 10 and the positive control (p > 0.05). Aditionally, we found the differences between the combination 10 and combination 6 for the protective effect of HUVEC (human umbilical vein endothelial cells) under high glucose concentration. The protective effects of combination 10 was stronger than combination 6, which suggested that combination 10 may have a better hypoglycemic activity in future studies. This study provides useful clues for the further design and discovery of anti-diabetic agents. View Full-Text
Keywords: chickpea; isoflavones; derivative synthesis; anti-diabetic activity chickpea; isoflavones; derivative synthesis; anti-diabetic activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Li, P.; Shi, X.; Wei, Y.; Qin, L.; Sun, W.; Xu, G.; Xu, T.; Liu, T. Synthesis and Biological Activity of Isoflavone Derivatives from Chickpea as Potent Anti-Diabetic Agents. Molecules 2015, 20, 17016-17040.

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