Characterization of a xylose containing oligosaccharide, an inhibitor of multidrug resistance in Staphylococcus aureus, from Ipomoea pes-caprae.
Pescaprein XVIII (1), a type of bacterial efflux pump inhibitor, was obtained from the CHCl(3)-soluble resin glycosides of beach morning glory (Ipomoea pes-caprae). The glycosidation sequence for pescaproside C, the glycosidic acid core of the lipophilic macrolactone 1 containing D-xylose and L-rhamnose, was characterized by means of several NMR techniques and FAB mass spectrometry. Recycling HPLC also yielded eight non-cytotoxic bacterial resistance modifiers, the two pescapreins XIX (2) and XX (3) as well as the known murucoidin VI (4), pecapreins II (6) and III (7), and stoloniferins III (5), IX (8) and X (9), all of which contain simonic acid B as their oligosaccharide core. Compounds 1-9 were tested for in vitro antibacterial and resistance-modifying activity against strains of Staphylococcus aureus possessing multidrug resistance efflux mechanisms. All of the pescapreins potentiated the action of norfloxacin against the NorA over-expressing strain by 4-fold (8 microg/mL from 32 microg/mL) at a concentration of 25 microg/mL.
Escobedo-Martínez
Carolina
C
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Mexico City, DF, Mexico.
Cruz-Morales
Sara
S
Fragoso-Serrano
Mabel
M
Rahman
M Mukhlesur
MM
Gibbons
Simon
S
Pereda-Miranda
Rogelio
R
D001426:Bacterial Proteins / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D018432:Drug Resistance, Multiple / Q000187:drug effects*; D035264:Flowers / Q000737:chemistry; D027741:Ipomoea / Q000737:chemistry*; D015394:Molecular Structure; D027425:ATP-Binding Cassette, Sub-Family C Proteins / Q000187:drug effects; D009643:Norfloxacin / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000235:genetics; D014994:Xylose / Q000737:chemistry*
D001426:Bacterial Proteins; D027425:ATP-Binding Cassette, Sub-Family C Proteins; D009643:Norfloxacin; D009844:Oligosaccharides; D014994:Xylose; C075040:NorA protein, Staphylococcus