Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

G Timité; AC Mitaine-Offer; T Miyamoto; C Tanaka; JF Mirjolet; O Duchamp; MA Lacaille-Dubois

doi:10.1055/s-0032-1320936

Planta Medica, Table of Contents

Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

G Timité ¹, AC Mitaine-Offer ¹, T Miyamoto ², C Tanaka ², JF Mirjolet ³, O Duchamp ³, MA Lacaille-Dubois ¹

¹EA 4267, FDE/UFC, Laboratoire de Pharmacognosie, Faculté de Pharmacie, Université de Bourgogne, 21079 Dijon Cedex, France
²Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812–8582, Japan
³Oncodesign, 20 Rue Jean Mazen, BP 27627, 21076 Dijon Cedex, France

Abstract

A phytochemical analysis of the whole plant of Allium schoenoprasum, has led to the isolation of seven new spirostane-type glycosides (1-7) while 1-6 were obtained as three pairs of inseparable (R)/(S)-isomers derivatives 1/2, 3/4, 5/6, and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-spirost-5-en-3β,12β,21-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (1) and its (25S)-isomer (2), (20S,25R)-spirost-5-en-3β,11α,21-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3) and its (25S)-isomer (4), laxogenin 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (5) and its (25S)-isomer (6), and (25R)-5α-spirostan-3β,11α-diol 3-O-β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside (7). Four of the isolated compounds were tested for cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines.