Antioxidative compounds isolated from the rhizomes of smaller galanga (Alpinia officinarum Hance)

Biofactors. 2004;21(1-4):305-8. doi: 10.1002/biof.552210159.

Abstract

Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1-7) were obtained and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, (E)-p-coumaryl alcohol gamma-O-methyl ether (1) and (E)-p-coumaryl alcohol (6); and the five novel compounds, stereoisomers of (4E)-1,5-bis(4-hydroxy-phenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxy-phenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-1,5-bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (7). Compounds 1-7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bulk phase.

MeSH terms

  • Alpinia / chemistry*
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification*
  • Linoleic Acids / chemistry
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Rhizome / chemistry*

Substances

  • Antioxidants
  • Linoleic Acids
  • methyl linoleate