title: Jalapinoside, a macrocyclic bisdesmoside from the resin glycosides of Ipomea purga, as a modulator of multidrug resistance in human cancer cells.
abstract: The first macrocyclic bisdesmoside resin glycoside, jalapinoside (4), was purified by preparative-scale recycling HPLC from the MeOH-soluble extracts of Ipomoea purga roots, the officinal jalap. Purgic acid C (3), a new glycosidic acid of ipurolic acid, was identified as 3-O-β-d-quinovopyranoside, 11-O-β-d-quinovopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-fucopyranosyl-(1→4)]-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-quinovopyranoside (3S,11S)-dihydroxytetradecanoic acid. The acylating residues of this core were acetic, (+)-(2S)-methylbutanoic, and dodecanoic acids. The site of lactonization was defined as C-3 of the second saccharide moiety. Reversal of multidrug resistance by this noncytotoxic compound was evaluated in vinblastine-resistant human breast carcinoma cells.
authors.affiliation: Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México , Mexico City, 04510 DF, Mexico.
authors.forename: Elihú
authors.initials: E
authors.lastname: Bautista
authors.forename: Mabel
authors.initials: M
authors.lastname: Fragoso-Serrano
authors.forename: Rogelio
authors.initials: R
authors.lastname: Pereda-Miranda
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D018432:Drug Resistance, Multiple / Q000187:drug effects*; D019008:Drug Resistance, Neoplasm / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D027741:Ipomoea / Q000737:chemistry*; D008800:Mexico; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012116:Resins, Plant / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism; D014747:Vinblastine / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D012116:Resins, Plant; D012503:Saponins; C511987:bisdesmoside; C000596052:jalapinoside; D014747:Vinblastine