Triterpenoid Saponins from the Fruits of Akebiae quinata

Dan Jiang, Qi Pin Gao, She Po Shi, Peng Fei Tu
2006 Chemical and pharmaceutical bulletin  
Akebiae quinata (THUNB.) DECNE. a well-known Chinese medicinal plant, is widely distributed in China, the fruits of the plant named "Bayuezha" is popularly used as an antineoplastic, diuretic agent in traditional Chinese medicine. Previous investigations revealed the genus Akebiae possessing rich triterpenoid saponins. Up to date, more than thirty triterpenoid saponins have been isolated from the fruits, leaves and roots of the plant of this genus. 1) As a continuous investigation on the
more » ... l constituents of the fruits of Akebiae quinata, eleven triterpenoid saponins including three new ones have been afforded. Herein we describe the isolation and structure elucidation of the new compounds. Results and Discussion The dried fruits of Akebiae quinata (THUNB.) DECNE. were extracted with hot 95% ethanol, After removal of the solvent under reduced pressure at 60 °C, the residue was suspended in water and defatted with petroleum ether. The aqueous layer was further extracted with ethyl acetate and n-butanol successively. A portion of the n-butanol extract was subjected to D101 porous polymer resin, silica gel, ODS C18 column chromatography and purefied by preparative HPLC (PHPLC) to afford eleven triterpinoid saponins including three new compounds. By comparing their NMR data with literatures, the known compounds were elucidated as hederagenin 3-O-a-L-arabinopyranoside (1), 2) oleanolic acid 3- 8), 7) oleanolic acid 3-O-b-D-xylopyranosyl(1→2)-a -L-arabinopyranosyl-28-O-b -D-glucopyranosyl(1→6)-b-D-glucopyranoside (10) 8) and hederagenin 3-O-a -L-rhamnopyranosyl(1→2)-a -L-arabinopyranosyl-28-Oa-L-rhamnopyranosyl(1→4)-b-D-glucopyranosyl(1→6)-b-Dglucopyranoside (11). 9) The new compounds 2, 3 and 9 were elucidated on the basis of their spectroscopic and physiochemical evidence. Compound 2 was obtained as a white amorphous powder. The positive mode HR-FAB-MS showed a [MϩNa] ϩ ion peak at m/z 757.4157, in accordance with an empirical mo-lecular formula of C 40 H 62 O 12 , which was supported by the 13
doi:10.1248/cpb.54.595 pmid:16651751 fatcat:65cwawact5hdxjyed3vy3kkoie