1,1-Diphenyl-2-picrylhydrazyl radical-scavenging active compounds from greater cardamom (Amomum subulatum Roxb.)

J Nutr Sci Vitaminol (Tokyo). 2001 Apr;47(2):167-71. doi: 10.3177/jnsv.47.167.

Abstract

Constituents of the fruits of greater cardamom (Amomum subulatum) were fractionated into three fractions, the dichloromethane extract, and the ethyl acetate-soluble and water-soluble fractions of the 70% aqueous acetone extract. The ethyl acetate-soluble fraction showed a high radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH). Four compounds were isolated from the ethyl acetate-soluble fraction, and their structures were ascribed to protocatechualdehyde (1), protocatechuic acid (2), 1,7-bis(3,4-dihydroxyphenyl)hepta-4E,6E-dien-3-one (3) and 2,3,7-trihydroxy-5-(3,4-dihydroxy-E-styryl)-6,7,8,9-tetrahydro-5H-benzocycloheptene (4) on the basis of spectroscopic evidence. This is the first isolation of these compounds from greater cardamom. In particular, 4 was a new type of cyclic diarylheptanoid. DPPH radical-scavenging activity of these compounds was measured by colorimetric analysis. Compounds 1 and 3 showed stronger activity than such natural antioxidants as alpha-tocopherol and L-ascorbic acid. Compounds 2 and 4 were comparable to alpha-tocopherol and L-ascorbic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / metabolism*
  • Bepridil / analogs & derivatives*
  • Bepridil / metabolism*
  • Biphenyl Compounds
  • Chromatography, Thin Layer
  • Colorimetry
  • Elettaria / chemistry*
  • Elettaria / metabolism
  • Free Radical Scavengers / metabolism*
  • Fruit / chemistry
  • Fruit / metabolism
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Picrates*
  • Plant Extracts / analysis
  • Plant Extracts / chemistry
  • Plant Extracts / metabolism*

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Free Radical Scavengers
  • Indicators and Reagents
  • Picrates
  • Plant Extracts
  • Bepridil
  • 1,1-diphenyl-2-picrylhydrazyl