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Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

2013; Elsevier BV; Volume: 88; Linguagem: Inglês

10.1016/j.phytochem.2012.12.001

1873-3700

Gaoussou Timité, Anne‐Claire Mitaine‐Offer, Tomofumi Miyamoto, Chiaki Tanaka, Jean-François Mirjolet, Olivier Duchamp, Marie‐Aleth Lacaille‐Dubois,

Natural product bioactivities and synthesis

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