Two glucosylated abscisic acid derivates from avocado seeds (Persea americana Mill. Lauraceae cv. Hass)

Phytochemistry. 2004 Apr;65(7):955-62. doi: 10.1016/j.phytochem.2003.12.007.

Abstract

Phytochemical investigation of avocado seed material (Persea americana Mill., Lauraceae) resulted in the isolation of two glucosylated abscisic acid derivates. One of these was not known as a natural product and can be regarded as a potential 'missing link' in abscisic acid metabolism in plants. After fractionation by high-speed countercurrent chromatography, and multiple steps of column chromatography, structures were elucidated by 1D-, 2D-NMR, electrospray-MS to be the novel beta-d-glucoside of (1'S,6'R)-8'-hydroxyabscisic acid, and (1'R,3'R,5'R,8'S)-epi-dihydrophaseic acid beta-d-glucoside. Absolute configuration was determined by circulardichroism, optical rotation, and by NOE experiments.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abscisic Acid / analogs & derivatives*
  • Abscisic Acid / isolation & purification
  • Abscisic Acid / metabolism
  • Circular Dichroism
  • Countercurrent Distribution
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Glucosides / metabolism
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Persea / chemistry*
  • Seeds / chemistry
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Glucosides
  • Abscisic Acid