Resin glycosides from Ipomoea wolcottiana as modulators of the multidrug resistance phenotype in vitro

• Published in: Phytochemistry (Oxford) 2016-03, Vol.123, p.48-57
• Main Authors: Corona-Castañeda, Berenice, Rosas-Ramírez, Daniel, Castañeda-Gómez, Jhon, Aparicio-Cuevas, Manuel Alejandro, Fragoso-Serrano, Mabel, Figueroa-González, Gabriela, Pereda-Miranda, Rogelio
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Convolvulaceae; Drug Resistance, Multiple - drug effects; Escherichia coli - drug effects; Female; Flowers - chemistry; Glycolipids; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Humans; Ipomoea - chemistry; Ipomoea wolcottiana; Molecular Structure; Multidrug-resistance; Nuclear Magnetic Resonance, Biomolecular; Resin glycosides; Resins, Plant - chemistry; Resins, Plant - isolation & purification; Resins, Plant - pharmacology; Salmonella - drug effects; Structural spectroscopy; Vinblastine - pharmacology
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2016.01.004

Six glycolipids were isolated from flowers of Ipomoea wolcottiana as multidrug resistance modulators by exerting a potentiation of antibiotic and vinblastine susceptibility in cells. [Display omitted] •Recycling liquid chromatography was used for the isolation of six resin glycosides from Ipomoea wolcottiana.•Their structures were characterized by NMR spectroscopy and mass spectrometry.•The six resin glycosides potentiated antibiotic susceptibility on multidrug resistant Gram-negative bacteria.•The six resin glycosides modulated vinblastine susceptibility in breast carcinoma cells. 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>512μg/mL) against multidrug-resistant strains of Escherichia coli, and two nosocomial pathogens: Salmonella enterica serovar Typhi and Shigella flexneri; however, when tested (25μg/mL) in combination with tetracycline, kanamycin or chloramphenicol, they exerted a potentiation effect of the antibiotic susceptibility up to eightfold (64μg/mL from 512μg/mL). It was also determined that these non-cytotoxic (CI50>8.68μM) agents modulated vinblastine susceptibility at 25μg/mL in MFC-7/Vin+ cells with a reversal factor (RFMCF-7/Vin+) of 2–130 fold.