Oleanolic acid and hederagenin glycosides from Weigela stelzneri

Abdelmalek Rezgui, Anne Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasure, Patrick Dutartre, Marie Aleth Lacaille-Dubois

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, and 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosylhederagenin 28-O-β-d-xylopyranosyl-(1 → 6)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid and 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.

Original languageEnglish
Pages (from-to)40-47
Number of pages8
JournalPhytochemistry
Volume123
DOIs
Publication statusPublished - Mar 1 2016

Fingerprint

Weigela
Oleanolic Acid
oleanolic acid
Glycosides
glycosides
Acids
acids
Cytotoxicity
cytotoxicity
Esters
esters
Cells
cell lines
Spectroscopic analysis
interleukin-1
Tumor Cell Line
anti-inflammatory activity
Interleukin-1
Mass spectrometry
Toxicity

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Rezgui, A., Mitaine-Offer, A. C., Miyamoto, T., Tanaka, C., Delemasure, S., Dutartre, P., & Lacaille-Dubois, M. A. (2016). Oleanolic acid and hederagenin glycosides from Weigela stelzneri. Phytochemistry, 123, 40-47. https://doi.org/10.1016/j.phytochem.2015.12.016

Oleanolic acid and hederagenin glycosides from Weigela stelzneri. / Rezgui, Abdelmalek; Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Delemasure, Stéphanie; Dutartre, Patrick; Lacaille-Dubois, Marie Aleth.

In: Phytochemistry, Vol. 123, 01.03.2016, p. 40-47.

Research output: Contribution to journalArticle

Rezgui, A, Mitaine-Offer, AC, Miyamoto, T, Tanaka, C, Delemasure, S, Dutartre, P & Lacaille-Dubois, MA 2016, 'Oleanolic acid and hederagenin glycosides from Weigela stelzneri', Phytochemistry, vol. 123, pp. 40-47. https://doi.org/10.1016/j.phytochem.2015.12.016
Rezgui, Abdelmalek ; Mitaine-Offer, Anne Claire ; Miyamoto, Tomofumi ; Tanaka, Chiaki ; Delemasure, Stéphanie ; Dutartre, Patrick ; Lacaille-Dubois, Marie Aleth. / Oleanolic acid and hederagenin glycosides from Weigela stelzneri. In: Phytochemistry. 2016 ; Vol. 123. pp. 40-47.
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abstract = "Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, and 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosylhederagenin 28-O-β-d-xylopyranosyl-(1 → 6)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid and 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50{\%} significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23{\%} and 28{\%}, respectively.",
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T1 - Oleanolic acid and hederagenin glycosides from Weigela stelzneri

AU - Rezgui, Abdelmalek

AU - Mitaine-Offer, Anne Claire

AU - Miyamoto, Tomofumi

AU - Tanaka, Chiaki

AU - Delemasure, Stéphanie

AU - Dutartre, Patrick

AU - Lacaille-Dubois, Marie Aleth

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N2 - Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, and 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosylhederagenin 28-O-β-d-xylopyranosyl-(1 → 6)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid and 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.

AB - Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, and 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosylhederagenin 28-O-β-d-xylopyranosyl-(1 → 6)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid and 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.

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