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■ New Noroleanane-Type Triterpene Saponins with Gastroprotective Effect and Platelet Aggregation Activity from the Flowers of Camellia japonica: Revised Structures of Camellenodiol and Camelledionol

Masayuki Yoshikawa,* Toshio Morikawa, Emi Fujiwara, Teruki Ohgushi, Yasunobu Asao, and Hisashi Matsuda

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan

Abstract

The methanolic extract from the flowers of Camellia japonica was found to exhibit potent gastroprotective effect on ethanol-induced gastric mucosal lesions in rats and platelet aggregation activity. Through bioassay-guided separation, three new 28-noroleanane-type triterpene saponins, camelliosides A, B, and C, and an oleanane-type triterpene saponin, camellioside D, were isolated from the methanolic extract. The absolute stereostructures of camelliosides A—D were determined on the basis of physicochemical and chemical evidence, which included the structure revision of the triterpene part, camellenodiol and camelledionol, using X-Ray crystallographic analysis and modified Mosher's method. Camelliosides A and B showed gastroprotective and platelet aggregating effects.