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

Molecules

Pengshou Li¹  Xiaojuan Shi¹  Ying Wei¹  Lingling Qin²  Wen Sun²  Guangyuan Xu²  Tunhai Xu¹  Tonghua Liu² 

[1]School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100029, China

[2] E-Mails:

[3]Health Cultivation Laboratory of the Ministry of Education, Beijing University of Chinese Medicine, Beijing 100029, China

[4] E-Mails:

关键词: chickpea;    isoflavones;    derivative synthesis;    anti-diabetic activity;   

DOI  :  10.3390/molecules200917016

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.