title: Triterpene saponins from Eryngium kotschyi.
abstract: Four new oleanane-type saponins 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyl-22-O-β,β-dimethylacryloylA1-barrigenol (1), 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyl-22-O-angeloylA1-barrigenol (2), 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-21,22,28-O-triacetyl-(3β,21β,22α)-olean-12-en-16-one (3), and 3-O-β-D-glucopyranosyl-(1 → 2)-glucopyranosyl-22-O-β-D-glucopyranosylsteganogenin (4), along with the known 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-22-O-angeloylA1-barrigenol and 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyloleanolic acid, were isolated from a methanol extract of the roots of Eryngium kotschyi by multiple chromatographic steps. Saponins 3 and 4 are unusual by the original structure of their aglycon. Compound 3 possessed an oleanane-type skeleton with a 21,22,28-triacetylation and a ketone function at the C-16 position. For compound 4, the 17,22-seco-oleanolic acid skeleton is rarely found in natural saponins.
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; Department of Pharmacognosy, Faculty of Pharmacy, Ankara University, Tandogan, 06100 Ankara, Turkey.
authors.forename: Sinem
authors.initials: S
authors.lastname: Aslan Erdem
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: Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
authors.forename: Tomofumi
authors.initials: T
authors.lastname: Miyamoto
authors.affiliation: Department of Pharmacognosy, Faculty of Pharmacy, Ankara University, Tandogan, 06100 Ankara, Turkey.
authors.forename: Murat
authors.initials: M
authors.lastname: Kartal
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: D031049:Eryngium / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D018517:Plant Roots / Q000737:chemistry; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D014421:Turkey
chemical_list: D012503:Saponins; C413246:oleanane; D009828:Oleanolic Acid
keywords: 2D NMR; A1-barrigenol; Apiaceae; Eryngium kotschyi; Steganogenin