Spirostane and cholestane glycosides from the bulbs of Allium nigrum L

Aymen Jabrane, Hichem Ben Jannet, Tomofumi Miyamoto, Jean François Mirjolet, Olivier Duchamp, Féthia Harzallah-Skhiri, Marie Aleth Lacaille-Dubois

Research output: Contribution to journalArticle

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Abstract

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)-5α-spirostan-2α,3β,6β-trio1-3-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (5a/5b) and 25(R,S)-5α-spirostan-2α,3β,6β-trio1 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaryl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-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 2.82μM against HT-29 and 1.59 and 3.45μM against HCT 116, respectively.

Original languageEnglish
Pages (from-to)447-455
Number of pages9
JournalFood Chemistry
Volume125
Issue number2
DOIs
Publication statusPublished - Mar 15 2011

Fingerprint

Spirostans
Cholestanes
Allium
Glycosides
Galactose
bulbs
glycosides
HCT116 Cells
Spectroscopic analysis
Phytochemicals
Cytotoxicity
varespladib methyl
Isomers
phytopharmaceuticals
Inhibitory Concentration 50
carcinoma
colon
isomers
inhibitory concentration 50
cytotoxicity

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Food Science

Cite this

Jabrane, A., Ben Jannet, H., Miyamoto, T., Mirjolet, J. F., Duchamp, O., Harzallah-Skhiri, F., & Lacaille-Dubois, M. A. (2011). Spirostane and cholestane glycosides from the bulbs of Allium nigrum L. Food Chemistry, 125(2), 447-455. https://doi.org/10.1016/j.foodchem.2010.09.028

Spirostane and cholestane glycosides from the bulbs of Allium nigrum L. / Jabrane, Aymen; Ben Jannet, Hichem; Miyamoto, Tomofumi; Mirjolet, Jean François; Duchamp, Olivier; Harzallah-Skhiri, Féthia; Lacaille-Dubois, Marie Aleth.

In: Food Chemistry, Vol. 125, No. 2, 15.03.2011, p. 447-455.

Research output: Contribution to journalArticle

Jabrane, A, Ben Jannet, H, Miyamoto, T, Mirjolet, JF, Duchamp, O, Harzallah-Skhiri, F & Lacaille-Dubois, MA 2011, 'Spirostane and cholestane glycosides from the bulbs of Allium nigrum L', Food Chemistry, vol. 125, no. 2, pp. 447-455. https://doi.org/10.1016/j.foodchem.2010.09.028
Jabrane A, Ben Jannet H, Miyamoto T, Mirjolet JF, Duchamp O, Harzallah-Skhiri F et al. Spirostane and cholestane glycosides from the bulbs of Allium nigrum L. Food Chemistry. 2011 Mar 15;125(2):447-455. https://doi.org/10.1016/j.foodchem.2010.09.028
Jabrane, Aymen ; Ben Jannet, Hichem ; Miyamoto, Tomofumi ; Mirjolet, Jean François ; Duchamp, Olivier ; Harzallah-Skhiri, Féthia ; Lacaille-Dubois, Marie Aleth. / Spirostane and cholestane glycosides from the bulbs of Allium nigrum L. In: Food Chemistry. 2011 ; Vol. 125, No. 2. pp. 447-455.
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abstract = "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)-5α-spirostan-2α,3β,6β-trio1-3-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (5a/5b) and 25(R,S)-5α-spirostan-2α,3β,6β-trio1 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaryl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-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 2.82μM against HT-29 and 1.59 and 3.45μM against HCT 116, respectively.",
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