2D-NMR; Cytotoxicity; Fabaceae; Millettia laurentii; Oleanane-type glycosides; Glycosides; Saponins; oleanane; Oleanolic Acid; Animals; Glycosides/chemistry; Mice; Molecular Structure; Oleanolic Acid/analogs & derivatives; Trees; Millettia; Saponins/chemistry; Pharmacology; Drug Discovery; General Medicine
Abstract :
[en] Seven previously undescribed oleanane-type glycosides were isolated from the trunk barks of a Central African tree named Millettia laurentii De Wild (Fabaceae). After the extraction from the barks, the isolation and purification of these compounds were achieved using various solid/liquid chromatographic methods. Their structures were established mainly by 1D and 2D NMR (COSY, TOCSY, ROESY, HSQC, HMBC) and mass spectrometry (ESI-MS), as 3-O-β-D-glucuronopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-β-D-glucuronopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-[β-d-xylopyranosyl-(1 → 2)]-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 2)]-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-α-L-arabinofuranosyl-(1 → 2)-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyloleanolic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 2)]-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyloleanolic acid. In addition, the cytotoxicity of six glycosides among the isolated ones, was evaluated against 4 T1 cell line from a mouse mammary gland tissue, using MTS method.
Pertuit, David; Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche Comté, 7, Bd Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France
Mitaine-Offer, Anne-Claire; Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche Comté, 7, Bd Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France. Electronic address: anne-claire.offer@u-bourgogne.fr
Miyamoto, Tomofumi; Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan
Tanaka, Chiaki; Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan
Delaude, Clément ; Université de Liège - ULiège > Département de chimie (sciences) > Centre de recherche phytochimique
Bellaye, Pierre-Simon; Plateforme d'Imagerie et de Radiothérapie Précliniques, Service de Médecine Nucléaire, Centre Georges-François Leclerc, BP77980 -, 21079 Dijon cedex, France
Collin, Bertrand; Plateforme d'Imagerie et de Radiothérapie Précliniques - ICMUB UMR CNRS 6302, Service de Médecine Nucléaire, Centre Georges-François Leclerc, BP77980, 21079 Dijon cedex, France
Lacaille-Dubois, Marie-Aleth; Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche Comté, 7, Bd Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France
Language :
English
Title :
Oleanane-type glycosides isolated from the trunk barks of the Central African tree Millettia laurentii.
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