Identification of (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-beta-D-glucopyranosides as damascenone progenitors in the flowers of Rosa damascena Mill

Biosci Biotechnol Biochem. 2002 Dec;66(12):2692-7. doi: 10.1271/bbb.66.2692.

Abstract

The progenitors of damascenone (1), the most intensive C13-norisoprenoid volatile aroma constituent of rose essential oil, were surveyed in the flowers of Rosa damascena Mill. Besides 9-O-beta-D-glucopyranosyl-3-hydroxy-7,8-didehydro-beta-ionol (4b), a stable progenitor already isolated from the residual water after steam distillation of flowers of R. damascena Mill., two labile progenitors were identified to be (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-beta-D-glucopyranosides (2b) based on their synthesis and HPLC-MS analytical data. Compound 2b gave damascenone (1), 3-hydroxy-beta-damascone (3) and 4b upon heating under acidic conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Cyclohexanes / chemistry
  • Cyclohexanes / metabolism
  • Flowers / metabolism*
  • Glucosides / chemistry
  • Glucosides / metabolism*
  • Molecular Structure
  • Norisoprenoids*
  • Rosa / metabolism*
  • Terpenes / chemistry
  • Terpenes / metabolism*

Substances

  • 3-hydroxy-beta-damascone
  • 9-O-glucopyranosyl-3-hydroxy-7,8-didehydro-beta-ionol
  • Cyclohexanes
  • Glucosides
  • Norisoprenoids
  • Terpenes
  • megastigma-6,7-dien-3,5,9-triol 9-O-glycopyranoside
  • beta-damascenone