Two new sesquiterpenoids and two new prenylated phenylpropanoids from Illicium fargesii, and neuroprotective activity of macranthol

Chem Pharm Bull (Tokyo). 2008 Aug;56(8):1201-4. doi: 10.1248/cpb.56.1201.

Abstract

Two new seco-prezizaane-type sesquiterpenoids 1, 2 and two new prenylated phenylpropanoids 4, 5 were isolated along with 15 known compounds from Illicium fargesii. The structures of 1, 2 were elucidated as 10-O-(E)- and 10-O-(Z)-cinnamoyl-2-oxo-6-deoxyneoanisatin by analysis of spectroscopic data and by comparison of their NMR data with those of previously reported 2-oxo-6-deoxyneoanisatin (3), respectively, whereas the structures of 4, 5 were identified as 4-allyl-2-(3-methylbut-2-en-1-yl)phenol and 4-allyl-2-(2-methylbut-3-en-2-yl)phenol, respectively, on the basis of spectroscopic data. Among the isolated compounds, macranthol (7) was found to have neuroprotective activity at 5--10 microM in rat cortical neurons cultured in DMEM/N2 medium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / isolation & purification*
  • Alkenes / pharmacology
  • Animals
  • Illicium / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / isolation & purification*
  • Neuroprotective Agents / pharmacology
  • Phenols / isolation & purification*
  • Phenols / pharmacology
  • Propanols / chemistry
  • Propanols / isolation & purification*
  • Propanols / pharmacology
  • Rats
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology

Substances

  • Alkenes
  • Neuroprotective Agents
  • Phenols
  • Propanols
  • Sesquiterpenes
  • macranthol
  • 1-phenylpropanol