title: Oleanolic acid and hederagenin glycosides from Weigela stelzneri.
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.
authors.affiliation: Laboratoire de Pharmacognosie, EA 4267, FDE, Université de Bourgogne Franche-Comté, UFR Sciences de Santé, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
authors.forename: Abdelmalek
authors.initials: A
authors.lastname: Rezgui
authors.affiliation: Laboratoire de Pharmacognosie, EA 4267, FDE, Université de Bourgogne Franche-Comté, UFR Sciences de Santé, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
authors.forename: Anne-Claire
authors.initials: AC
authors.lastname: Mitaine-Offer
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
authors.forename: Tomofumi
authors.initials: T
authors.lastname: Miyamoto
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
authors.forename: Chiaki
authors.initials: C
authors.lastname: Tanaka
authors.affiliation: Cohiro, UFR Sciences de Santé, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Delemasure
authors.affiliation: Cohiro, UFR Sciences de Santé, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
authors.forename: Patrick
authors.initials: P
authors.lastname: Dutartre
authors.affiliation: Laboratoire de Pharmacognosie, EA 4267, FDE, Université de Bourgogne Franche-Comté, UFR Sciences de Santé, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France. Electronic address: m-a.lacaille-dubois@u-bourgogne.fr.
authors.forename: Marie-Aleth
authors.initials: MA
authors.lastname: Lacaille-Dubois
mesh_terms: D027922:Caprifoliaceae / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D053583:Interleukin-1beta / Q000032:analysis / Q000187:drug effects / Q000378:metabolism; D008070:Lipopolysaccharides / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D053583:Interleukin-1beta; D008070:Lipopolysaccharides; D009828:Oleanolic Acid; C025763:hederagenin
keywords: Anti-inflammatory; Cytotoxicity; Glycoside; Hederagenin; NMR; Oleanolic acid; Weigela stelzneri (Caprifoliaceae)