Asymmetric synthesis and biological activity of nor-α-tocopherol, a new vitamin E analogue

Chembiochem. 2011 Jan 3;12(1):118-24. doi: 10.1002/cbic.201000511.

Abstract

The vitamin E analogues (2R,4'R,8'R)-nor-α-tocopherol (94 % de) and (2RS,4'R,8'R)-nor-α-tocopherol have been synthesized from (all R)-hexahydrofarnesol and phytol, respectively. According to in vitro experiments with murine macrophages nor-α-tocopherol is an anti-inflammatory compound more potent than α-tocopherol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Cell Line
  • Cytokines / metabolism
  • Inflammation / genetics
  • Macrophages / drug effects
  • Macrophages / enzymology
  • Macrophages / metabolism
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • Nitric Oxide Synthase Type II / metabolism
  • RNA, Messenger / genetics
  • RNA, Messenger / metabolism
  • Stereoisomerism
  • alpha-Tocopherol / analogs & derivatives
  • alpha-Tocopherol / chemical synthesis*
  • alpha-Tocopherol / chemistry
  • alpha-Tocopherol / pharmacology*

Substances

  • Antioxidants
  • Cytokines
  • RNA, Messenger
  • Nitric Oxide Synthase Type II
  • alpha-Tocopherol