Spirostane and cholestane glycosides from the bulbs of Allium nigrum L.

A phytochemical investigation of the fresh bulbs of Allium nigrum L. led to the isolation of new spirostane-type glycosides as two inseparable isomer mixtures, nigrosides A1/A2 (1a/1b) and nigrosides B1/B2 (2a/2b), two new cholestane-type glycosides, nigrosides C and D (3 and 4), together with the known compounds, 25(R,S)-5 alpha-spirostan-2 alpha,3 beta,6 beta-trio1-3-O-beta-D-glucopyranosyl-(1 -> 2)-O-[beta-D-xylopyranosyl-(1 -> 3)]-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-galactopyranoside (5a/5b) and 25(R,S)-5 alpha-spirostan-2a,3 beta,6 beta-trio1 3-O-beta-d-glucopyranosyl-(1 -> 2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaryl-beta-D-xylopyranosyl-(1 -> 3)]-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-galactopyranoside (6a/6b), isolated from this plant for the first time. All structures were elucidated mainly by spectroscopic analysis (1D and 2D NMR experiments, FABMS, HRESIMS) and by comparison with literature data. Cytotoxicity of the isolated compounds was assessed against human colon carcinoma (HT-29 and HCT 116) cell lines. Compounds 5a/5b and 6a/6b were found to be the most active with IC50 values 1.09 and 2.82 mu M against HT-29 and 1.59 and 3.45 mu M against HCT 116, respectively. (C) 2010 Elsevier Ltd All rights reserved.