Eriosema chinense: a rich source of antimicrobial and antioxidant flavonoids

Phytochemistry. 2013 Dec:96:353-9. doi: 10.1016/j.phytochem.2013.06.004. Epub 2013 Oct 15.

Abstract

Six prenylated flavonoids, (2R,3S)-3,5,4'-trihydroxy-6″-6″dimethylpyrano(2″,3″:7,6)-8-(3″', 3″'-dimethylallyl)flavanone, (2R,3S)-3,5,2'-trihydroxy-4'-methoxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(3″',3″'-dimethylallyl)flavanone, (2R,3R)-3,5,2',4'-tetrahydroxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(3″',3″'-dimethylallyl)flavanone, 3,5,2',4'-tetrahydroxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(3″',3″'-dimethylallyl)flavone, (2R,3R,2″'R)-3,5,2″'-trihydroxy-4'-methoxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(3″'-methylbut-3″'-enyl)flavanone, (2R,3R)-3,5-dihydroxy-4'-methoxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(2″',3″'-epoxy-3″'-methyl butyl)flavanone, an isoflavone, 6,7-dimethoxy-5,2',4'-trihydroxyisoflavone, and octaeicosanyl-trans-p-coumarate together with 12 known compounds, were isolated from roots of Eriosema chinense. This structural elucidation was determined by spectroscopic methods. Several isolates and derivatives were evaluated for their antimicrobial and antioxidant activities. Results obtained provide additional evidence showing that the presence of both the free phenolic OH and the lipophilic prenyl groups are crucial for potent antimicrobial activity against yeast, gram positive and gram negative bacteria, whereas the presence of free phenolic OH group is required for strong radical scavenging property.

Keywords: Antimicrobial activity; Antioxidant activity; Eriosema chinense Vogel; Flavonoids; Leguminosae-Papilionoidaeae.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification*
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / pharmacology
  • Candida albicans / drug effects
  • Erythrina / chemistry
  • Fabaceae / chemistry*
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Picrates / pharmacology
  • Plant Roots / chemistry
  • Stereoisomerism
  • Thailand

Substances

  • Anti-Infective Agents
  • Antioxidants
  • Biphenyl Compounds
  • Flavonoids
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl