Glochidionionosides A-D: megastigmane glucosides from leaves of Glochidion zeylanicum (Gaertn.) A. Juss

Chem Pharm Bull (Tokyo). 2003 Mar;51(3):286-90. doi: 10.1248/cpb.51.286.

Abstract

Five megastigmane glucosides were isolated from the leaves of Glochidion zeylanicum. One of them was a known compound, blumenol C O-beta-D-glucopyranoside (1), and the structures of the four new compounds, glochidionionosides A-D (2-5), were mainly elucidated by spectroscopic methods, including a modified Mosher's method. The absolute configurations of the six-membered ring of glochidionionoside D (5) were deduced by beta-D-glucopyranosylation-induced shift trends in the (13)C-NMR spectra and confirmed by X-ray analysis as its p-bromobenzoate (5b), and the axis chirality of C-7 was determined to be R.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclohexanones / chemistry*
  • Cyclohexanones / isolation & purification
  • Euphorbiaceae*
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Norisoprenoids*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Leaves

Substances

  • Cyclohexanones
  • Glucosides
  • Norisoprenoids
  • Plant Extracts
  • megastigmane