title: Acylated oleanane-type saponins from Ganophyllum giganteum.
abstract: Five oleanane-type saponins, 3-O-β-D-glucuronopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (1), 3-O-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (2), zanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (3), zanhic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester (4), medicagenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the β-D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated.
authors.affiliation: Laboratoire de Pharmacognosie, EA 4267 (FDE/UFC), Faculté de Pharmacie, Université de Bourgogne, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France; Laboratorio de Productos Naturales. Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela.
authors.forename: Elier Galarraga
authors.initials: EG
authors.lastname: Montes
authors.affiliation: Laboratoire de Pharmacognosie, EA 4267 (FDE/UFC), Faculté de Pharmacie, Université de Bourgogne, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
authors.forename: Anne-Claire
authors.initials: AC
authors.lastname: Mitaine-Offer
authors.affiliation: Laboratorio de Productos Naturales. Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela.
authors.forename: Juan Manuel
authors.initials: JM
authors.lastname: Amaro-Luis
authors.affiliation: Universität Siegen, OC-II, Naturwissenschaftlich-Technische Fakultät, Adolf-Reichwein-Str. 2, D-57076 Siegen, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Paululat
authors.affiliation: Centre de Recherche Phytochimique, Université de Liège, Institut de Chimie-B6, Sart Tilman, B-4000 Liège I, Belgium.
authors.forename: Clément
authors.initials: C
authors.lastname: Delaude
authors.affiliation: Institut des Sciences Moléculaires, CNRS-UMR 5255 et Institut Européen de Chimie et Biologie, Université de Bordeaux, 2 rue Robert Escarpit, 33607 Pessac Cedex, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Pouységu
authors.affiliation: Institut des Sciences Moléculaires, CNRS-UMR 5255 et Institut Européen de Chimie et Biologie, Université de Bordeaux, 2 rue Robert Escarpit, 33607 Pessac Cedex, France.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Quideau
authors.affiliation: Laboratorio de Productos Naturales. Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela.
authors.forename: Luis B
authors.initials: LB
authors.lastname: Rojas
authors.affiliation: Cohiro, UFR Médecine, 7, Bd. Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Delemasure
authors.affiliation: Cohiro, UFR Médecine, 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/UFC), Faculté de Pharmacie, Université de Bourgogne, 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: D000215:Acylation; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006868:Hydrolysis; D007249:Inflammation / Q000188:drug therapy; D051379:Mice; D008968:Molecular Conformation; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D029631:Sapindaceae / Q000737:chemistry*; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D000972:Antineoplastic Agents, Phytogenic; D001688:Biological Products; D012503:Saponins; C413246:oleanane; D009828:Oleanolic Acid
keywords: Ganophyllum giganteum; Medicagenic acid; Sapindaceae; Saponins; Zanhic acid