Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

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

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)61-66
Number of pages6
JournalPhytochemistry
Volume88
DOIs
Publication statusPublished - Apr 1 2013

Fingerprint

Chive
Spirostans
Allium schoenoprasum
steroid saponins
glycols
Spectroscopic analysis
Saponins
Phytochemicals
Cytotoxicity
Glycosides
colorectal neoplasms
Galactose
Colonic Neoplasms
phytopharmaceuticals
Mass spectrometry
glycosides
cytotoxicity
Mass Spectrometry
Cells
cell lines

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Timité, G., Mitaine-Offer, A. C., Miyamoto, T., Tanaka, C., Mirjolet, J. F., Duchamp, O., & Lacaille-Dubois, M. A. (2013). Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum. Phytochemistry, 88, 61-66. https://doi.org/10.1016/j.phytochem.2012.12.001

Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum. / Timité, Gaoussou; Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Mirjolet, Jean François; Duchamp, Olivier; Lacaille-Dubois, Marie Aleth.

In: Phytochemistry, Vol. 88, 01.04.2013, p. 61-66.

Research output: Contribution to journalArticle

Timité, G, Mitaine-Offer, AC, Miyamoto, T, Tanaka, C, Mirjolet, JF, Duchamp, O & Lacaille-Dubois, MA 2013, 'Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum', Phytochemistry, vol. 88, pp. 61-66. https://doi.org/10.1016/j.phytochem.2012.12.001
Timité, Gaoussou ; Mitaine-Offer, Anne Claire ; Miyamoto, Tomofumi ; Tanaka, Chiaki ; Mirjolet, Jean François ; Duchamp, Olivier ; Lacaille-Dubois, Marie Aleth. / Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum. In: Phytochemistry. 2013 ; Vol. 88. pp. 61-66.
@article{e99bfd7c5a4042e5a445008a50ec898b,
title = "Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum",
abstract = "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.",
author = "Gaoussou Timit{\'e} and Mitaine-Offer, {Anne Claire} and Tomofumi Miyamoto and Chiaki Tanaka and Mirjolet, {Jean Fran{\cc}ois} and Olivier Duchamp and Lacaille-Dubois, {Marie Aleth}",
year = "2013",
month = "4",
day = "1",
doi = "10.1016/j.phytochem.2012.12.001",
language = "English",
volume = "88",
pages = "61--66",
journal = "Phytochemistry",
issn = "0031-9422",
publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

AU - Timité, Gaoussou

AU - Mitaine-Offer, Anne Claire

AU - Miyamoto, Tomofumi

AU - Tanaka, Chiaki

AU - Mirjolet, Jean François

AU - Duchamp, Olivier

AU - Lacaille-Dubois, Marie Aleth

PY - 2013/4/1

Y1 - 2013/4/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84874376819&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84874376819&partnerID=8YFLogxK

U2 - 10.1016/j.phytochem.2012.12.001

DO - 10.1016/j.phytochem.2012.12.001

M3 - Article

C2 - 23357597

AN - SCOPUS:84874376819

VL - 88

SP - 61

EP - 66

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

ER -