Xiaoan Wen, Jun O. Liu, Luyong Zhang
Nov 1, 2010
Citations
0
Influential Citations
12
Citations
Journal
Chinese Journal of Natural Medicines
Abstract
Abstract Aim To study glycogen phosphorylase inhibitory activity of natural pentacyclic triterpenes bearing 23-hydroxy or 24-hydroxy. Methods Arjunolic acid, bayogenin, hederagonic acid and 4- epi -hederagonic acid were synthesized from oleanolic acid as the starting material and biologically evaluated as glycogen phosphorylase inhibitors. Results Arjunolic acid, bayogenin, hederagonic acid and 4- epi -hederagonic acid were successfully semi-synthesized by multiple steps. The synthesis of arjunolic acid was via 11 steps in about 10% overall yield, and bayogenin via 14 steps in about 12% overall yield. Biological evaluation indicated that arjunolic acid, bayogenin, hederagonic acid and 4- epi -hederagonic acid showed moderate potency of glycogen phosphorylase inhibition with IC 50 of 53-103 μmol·L −1 . Conclusion Arjunolic acid, bayogenin, hederagonic acid and 4- epi -hederagonic acid are glycogen phosphorylase inhibitors with moderate potency. Insert of 23-hydroxy or 24-hydroxy to oleanane skeleton has a tendency to be unfavorable to GP inhibition.