Isolation of 10-hydroxycoronaridine from Tabernaemontana penduliflora and its estrogen-like activity.

The methanol extract of Tabernaemontana penduliflora was found to appreciably inhibit [ 3 H]-estradiol binding to estrogen receptors. Activity-guided fractionation led to the isolation of two known alkaloids, 10-hydroxycoronaridine (1) and its 10-O-methyl ether, voacangine (2). These alkaloids together with other related alkaloids were tested for their estrogenic activities. Among these molecules, 1 was found to be the most potent estrogen agonist and is distinctly more active than genistein.