Pharbitis nil CHOISY [ϭIpomoea nil (L.) ROTH] is found throughout Southeast Asia. The seeds and the resin extracted from the plant are medicinal. The main use is as a purgative.1) The Japanese morning glory has been domesticated as an ornamental plant in Japan. There have been several reports on the isolation of resin glycosides, 2-4) a diterpenoid, pharbitic acid, 5) flavonoids, caffeic acid, and chlorogenic acid derivatives, 6) and anthocyanins 7-10) from the seeds and flowers of this plant but there has been no report on the chemical investigation of the saponins in the seeds. In continuation of our studies on phytochemical studies on naturally occurring bioactive glycosides, [11][12][13][14] we became interested in the saponin content of the seeds of the plant. This paper describes the structural determination of the two new saponins isolated from the MeOH extract of the seeds.The powdered seeds of P. nil were sonicated with MeOH and partitioned as described in the Experimental. b-Sitosterol and its glucoside and caffeic acid and its methyl ester were isolated by successive chromatography using silica gel and reverse-phase C 18 from the hexane and EtOAc fractions, respectively. The BuOH-soluble fraction after repeated chromatographic purification over MCI gel and reverse-phase C 18 afforded two compounds designated pharbitosides A (1) and B (2).Pharbitoside A (1) was obtained as colorless crystalline needles. High-resolution (HR) FAB-MS gave the composition C 48 H 78 O 18 . An inspection of the 1 H-and 13 C-NMR spectra of the compound readily indicated the presence of three monosaccharide units through easily identifiable signals for anomeric protons and carbons. Acid hydrolysis of 1 afforded glucose (Glc) and rhamnose (Rha) as the sugar components identified on TLC analysis by comparison with authentic samples. The absolute configurations of sugars were determined to be the L-form for Rha and D-form for Glc, respectively, which were identified by GLC analysis of the thiazolidine derivatives.15) The negative-ion mode FAB mass spectrum of 1 exhibited an [MϪH] Ϫ ion at m/z 941, which is consistent with a trisaccharide glycoside carrying two Glc, one Rha, and an aglycon with a molecular mass of 472. Ϫ showed the presence of a linear sugar chain, and the sugar sequence appeared to be that of Glc-Glc-Rha.16) The spectroscopic data of the aglycon moiety of 1 were closely related to those of oleanolic acid 17) ; however, the molecular formula of the aglycon moiety was higher by one oxygen atom than that of oleanolic acid, implying the presence of one more hydroxyl group in addition to the C-3 hydroxyl group. The oxygenated methylene protons at