Vavilosides A1/A2–B1/B2, new furostane glycosides from the bulbs of Allium vavilovii with cytotoxic activity

Abstract

A phytochemical analysis of the bulbs of Allium vavilovii M. Pop. & Vved. was attained for the first time extensively, affording to the isolation of four new furostanol saponins, named vavilosides A1/A2–B1/B2 (1a/b–2a/2b), as two couple of isomers in equilibrium, together with ascalonicoside A1/A2 (3a/3b) and 22-O-methyl ascalonicoside A1/A2 (4a/4b), previously isolated from shallot, Allium ascalonicum. High concentrations of kaempferol, kaempferide, and kaempferol 4I-glucoside were also isolated. The chemical structures of the new compounds, established through a combination of extensive nuclear magnetic resonance, mass spectrometry and chemical analyses, were identified as (25R)-furost-5(6)-en-1b,3b,22a,26- tetraol 1-O-a-L-rhamnopyranosyl-(1?2)-O-b-D-galactopyranosyl 26-O-a-L-rhamnopyranoside (vaviloside A1), (25R)-furost-5(6)-en-1b,3b,22b,26-tetraol 1-O-a-L-rhamnopyranosyl-(1?2)-O-b-D-galactopyranosyl 26-O-a-L-rhamnopyranoside (vaviloside A2), (25R)-furost-5(6)-en-1b,3b,22a,26-tetraol 1-O-a-Lrhamnopyranosyl-( 1?2)-O-b-D-xylopyranosyl 26-O-a-L-rhamnopyranoside (vaviloside B1), (25R)-furost- 5(6)-en-1b,3b,22b,26-tetraol 1-O-a-L-rhamnopyranosyl-(1?2)-O-b-D-xylopyranosyl 26-O-a-Lrhamnopyranoside (vaviloside B2). The isolated saponins showed cytotoxic activity on J-774, murine monocyte/macrophage, and WEHI-164, murine fibrosarcoma, cell lines with the following rank: vaviloside B1/B2 > ascalonicoside A1/A2 > vaviloside A1/A2. 2013 Elsevier Ltd. All rights reserved

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