Characterization of a xylose containing oligosaccharide, an inhibitor of multidrug resistance in Staphylococcus aureus, from Ipomoea pes-caprae

Carolina Escobedo-Martínez, Sara Cruz-Morales, Mabel Fragoso-Serrano, M. Mukhlesur Rahman, Simon Gibbons, Rogelio Pereda-Miranda

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Pescaprein XVIII (1), a type of bacterial efflux pump inhibitor, was obtained from the CHCl3-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 μg/mL from 32 μg/mL) at a concentration of 25 μg/mL.

Original languageEnglish
Pages (from-to)1796-1801
Number of pages6
JournalPhytochemistry
Volume71
Issue number14-15
Early online date30 Jul 2010
DOIs
Publication statusPublished - Oct 2010

Keywords

  • Convolvulaceae
  • Ipomoea pes-caprae
  • Multidrug resistance
  • Pentasaccharide
  • Resin glycoside
  • Staphylococcus aureus
  • Structural spectroscopy

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