γ-Hydroxynitrile glucosides from the seeds of Prinsepia utilis

Phytochemistry. 2014 Sep:105:135-40. doi: 10.1016/j.phytochem.2014.05.018. Epub 2014 Jun 18.

Abstract

γ-Hydroxynitrile glucosides (prinsepicyanosides A-E) were isolated alongside 11 known compounds from seeds of Prinsepia utilis Royle. Their structures were determined by detailed analysis of NMR and MS spectroscopic data. The relative configuration of prinsepicyanoside C was established by Cu-Kα X-ray crystallography. Prinsepicyanoside A, osmaronin, and 4-(hydroxylmethyl)-5H-furan-2-one exhibited borderline antibacterial activity against Salmonella gallinarum, Vibrio parahaemolyticus, and Vibrio cholera with MIC values of 30.1, 20.7, and 22.8μg/mL, respectively.

Keywords: Antibacterial activity; Prinsepia utilis Royle; Rosaceae; γ-Hydroxynitrile glucosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Crystallography, X-Ray
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Furans / chemistry
  • Furans / isolation & purification*
  • Furans / pharmacology
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Nitriles / chemistry
  • Nitriles / isolation & purification*
  • Nuclear Magnetic Resonance, Biomolecular
  • Rosaceae / chemistry*
  • Salmonella / drug effects
  • Seeds / chemistry*
  • Stereoisomerism
  • Vibrio / drug effects

Substances

  • Anti-Bacterial Agents
  • Drugs, Chinese Herbal
  • Furans
  • Glucosides
  • Nitriles
  • prinsepicyanoside A