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Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum

Allium leucanthum C. Koch is an endemic Caucasian species that grows in Georgia. The flowers are used in traditional medicine. Phytochemical investigation allowed the isolation of seven spirostanol type saponins from the flowers. Their structures were elucidated on the base of NMR and HRESIMS spectr...

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Autores principales: Mskhiladze, Lasha, Legault, Jean, Lavoie, Serge, Mshvildadze, Vakhtang, Kuchukhidze, Jumber, Elias, Riad, Pichette, André
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245281/
https://www.ncbi.nlm.nih.gov/pubmed/19037184
http://dx.doi.org/10.3390/molecules13122925
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author Mskhiladze, Lasha
Legault, Jean
Lavoie, Serge
Mshvildadze, Vakhtang
Kuchukhidze, Jumber
Elias, Riad
Pichette, André
author_facet Mskhiladze, Lasha
Legault, Jean
Lavoie, Serge
Mshvildadze, Vakhtang
Kuchukhidze, Jumber
Elias, Riad
Pichette, André
author_sort Mskhiladze, Lasha
collection PubMed
description Allium leucanthum C. Koch is an endemic Caucasian species that grows in Georgia. The flowers are used in traditional medicine. Phytochemical investigation allowed the isolation of seven spirostanol type saponins from the flowers. Their structures were elucidated on the base of NMR and HRESIMS spectrometry data. A new compound, which we have named leucospiroside A (5), has been identified as (25R)-5α-spirostane-2α,3β,6β-triol 3-O-β-glucopyranosyl-(1→3)-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-β-glucopyranosyl-(1→4)-β-galactopyranoside. The six others were known substances, but are described in this plant for the first time. The crude extract, spirostanol and furostanol fractions, as well as isolated compounds, were evaluated for their in vitro cytotoxic activity. Compounds 1-3 and 5 were found to be the most active, with relatively similar IC(50) values ranging from 3.7 to 5.8 µM for a lung cancer cell line (A549) and 5.6 to 8.2 µM for a colon cancer cell line (DLD-1).
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spelling pubmed-62452812018-11-26 Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum Mskhiladze, Lasha Legault, Jean Lavoie, Serge Mshvildadze, Vakhtang Kuchukhidze, Jumber Elias, Riad Pichette, André Molecules Article Allium leucanthum C. Koch is an endemic Caucasian species that grows in Georgia. The flowers are used in traditional medicine. Phytochemical investigation allowed the isolation of seven spirostanol type saponins from the flowers. Their structures were elucidated on the base of NMR and HRESIMS spectrometry data. A new compound, which we have named leucospiroside A (5), has been identified as (25R)-5α-spirostane-2α,3β,6β-triol 3-O-β-glucopyranosyl-(1→3)-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-β-glucopyranosyl-(1→4)-β-galactopyranoside. The six others were known substances, but are described in this plant for the first time. The crude extract, spirostanol and furostanol fractions, as well as isolated compounds, were evaluated for their in vitro cytotoxic activity. Compounds 1-3 and 5 were found to be the most active, with relatively similar IC(50) values ranging from 3.7 to 5.8 µM for a lung cancer cell line (A549) and 5.6 to 8.2 µM for a colon cancer cell line (DLD-1). MDPI 2008-11-26 /pmc/articles/PMC6245281/ /pubmed/19037184 http://dx.doi.org/10.3390/molecules13122925 Text en © 2008 by the authors. Licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Mskhiladze, Lasha
Legault, Jean
Lavoie, Serge
Mshvildadze, Vakhtang
Kuchukhidze, Jumber
Elias, Riad
Pichette, André
Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
title Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
title_full Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
title_fullStr Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
title_full_unstemmed Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
title_short Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
title_sort cytotoxic steroidal saponins from the flowers of allium leucanthum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245281/
https://www.ncbi.nlm.nih.gov/pubmed/19037184
http://dx.doi.org/10.3390/molecules13122925
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