Saponins of Pericarps of Sapindus mukurossi GAERTN. and Solubilization of Monodesmosides by Bisdesmosides

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From pericarps of Sapindus mukurossi (Japanese name : Enmei-hi), saponins of hederagenin (1), 2-7,9,11 and 12 were isolated along with sapindosides A (10) and B (8), both of which have already been isolated from this crude drug. Saponins 7 and 9 were identified as α-L-arabinopyranosyl (1→3)-α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoside and α-L-arabinofuranosyl (1→3)-α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoside of 1,respectively, both of which were recently isolated from Lecaniodiscus cupanoides by Sandberg et al. New saponins named mukurozi-saponins E_1 (11) and G (12) were proved to be the mono-acetate of 8 and the di-acetate of 7,respectively. By means of mass and ^<13>C nuclear magnetic resonance (NMR) spectroscopy, the locations of the acetyl groups of 11 and 12 were established to be at the 4-hydroxyl group of the xylosyl unit of 8 and at the 3,4-hydroxyl groups of the terminal arabinosyl unit of 7,respectively. The other new saponins, named mukurozi-saponins X (6), Y_1 (5) and Y_2 (4), were revealed to be β-sophorosyl esters of 10,8 and 7,respectively, by comparison of the mass and ^<13>C NMR spectra with those of the β-sophorosyl ester of 1 (13), which was synthesized from 1 as a reference compound for the study of the anomalous glycosylation shifts. Studies on the structures of the remaining saponins, 2 and 3,are in progress. The water solubilities of the monodesmosides, 7-9,which cause remarkable enhancement of the absorption of sodium ampicillin from rat intestine and rectum, were greatly increased by the bisdesmosides, 4-6.
公益社団法人日本薬学会の論文
1983-06-25

Saponins of Pericarps of Sapindus mukurossi GAERTN. and Solubilization of Monodesmosides by Bisdesmosides

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