Absolute configuration of (+)-pinoresinol 4-O-[6''-O-galloyl]-beta-D-glucopyranoside, macarangiosides E, and F isolated from the leaves of Macaranga tanarius

Phytochemistry. 2009 Jul;70(10):1277-85. doi: 10.1016/j.phytochem.2009.07.020. Epub 2009 Aug 13.

Abstract

A lignan glucoside, (+)-pinoresinol 4-O-[6''-O-galloyl]-beta-D-glucopyranoside (1), and two megastigmane glucosides, named macarangiosides E and F (2,3), together with 15 known compounds (4-18) were isolated from leaves of Macaranga tanarius (L.) Müll.-Arg. (Euphorbiaceae). Their structures were elucidated by spectroscopic and chemical analyses. In addition, the absolute stereochemistry of macarangiosides B and C isolated previously from the same plant was also determined for the first time. Compounds 1 and 2 were galloylated on glucose and possessed potent DPPH radical-scavenging activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cyclohexanones / chemistry
  • Cyclohexanones / pharmacology
  • Euphorbiaceae / chemistry*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology*
  • Glucosides / chemistry*
  • Glucosides / pharmacology*
  • Humans
  • Molecular Structure
  • Norisoprenoids / chemistry
  • Norisoprenoids / pharmacology
  • Plant Leaves / chemistry*

Substances

  • Cyclohexanones
  • Free Radical Scavengers
  • Glucosides
  • Norisoprenoids
  • megastigmane