title: Resin glycosides from Ipomoea wolcottiana as modulators of the multidrug resistance phenotype in vitro.
abstract: Recycling liquid chromatography was used for the isolation and purification of resin glycosides from the CHCl3-soluble extracts prepared using flowers of Ipomoea wolcottiana Rose var. wolcottiana. Bioassay-guided fractionation, using modulation of both antibiotic activity against multidrug-resistant strains of Gram-negative bacteria and vinblastine susceptibility in breast carcinoma cells, was used to isolate the active glycolipids as modulators of the multidrug resistance phenotype. An ester-type dimer, wolcottine I, one tetra- and three pentasaccharides, wolcottinosides I-IV, in addition to the known intrapilosin VII, were characterized by NMR spectroscopy and mass spectrometry. In vitro assays established that none of these metabolites displayed antibacterial activity (MIC>512 μg/mL) against multidrug-resistant strains of Escherichia coli, and two nosocomial pathogens: Salmonella enterica serovar Typhi and Shigella flexneri; however, when tested (25 μg/mL) in combination with tetracycline, kanamycin or chloramphenicol, they exerted a potentiation effect of the antibiotic susceptibility up to eightfold (64 μg/mL from 512 μg/mL). It was also determined that these non-cytotoxic (CI50>8.68 μM) agents modulated vinblastine susceptibility at 25 μg/mL in MFC-7/Vin(+) cells with a reversal factor (RFMCF-7/Vin(+)) of 2-130 fold.
authors.affiliation: Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 DF, Mexico.
authors.forename: Berenice
authors.initials: B
authors.lastname: Corona-Castañeda
authors.affiliation: Departamento de Química de Biomacromoléculas, Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 DF, Mexico.
authors.forename: Daniel
authors.initials: D
authors.lastname: Rosas-Ramírez
authors.affiliation: Grupo Químico de Investigación y Desarrollo Ambiental, Facultad de Ciencias y Tecnologías, Universidad del Quindío, Armenia, Colombia.
authors.forename: Jhon
authors.initials: J
authors.lastname: Castañeda-Gómez
authors.affiliation: Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 DF, Mexico.
authors.forename: Manuel Alejandro
authors.initials: MA
authors.lastname: Aparicio-Cuevas
authors.affiliation: Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 DF, Mexico.
authors.forename: Mabel
authors.initials: M
authors.lastname: Fragoso-Serrano
authors.affiliation: Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 DF, Mexico.
authors.forename: Gabriela
authors.initials: G
authors.lastname: Figueroa-González
authors.affiliation: Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 DF, Mexico. Electronic address: pereda@unam.mx.
authors.forename: Rogelio
authors.initials: R
authors.lastname: Pereda-Miranda
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018432:Drug Resistance, Multiple / Q000187:drug effects*; D004926:Escherichia coli / Q000187:drug effects; D005260:Female; D035264:Flowers / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D027741:Ipomoea / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012116:Resins, Plant / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012475:Salmonella / Q000187:drug effects; D014747:Vinblastine / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D006027:Glycosides; D012116:Resins, Plant; D014747:Vinblastine
keywords: Convolvulaceae; Glycolipids; Ipomoea wolcottiana; Multidrug-resistance; Resin glycosides; Structural spectroscopy