Isolation of a reduced form of cyanidin 3-O-β-D-glucoside from immature black soybean (Glycine max (L.) Merr.) and its reducing properties

J Oleo Sci. 2013;62(8):623-9. doi: 10.5650/jos.62.623.

Abstract

5,7,3',4'-Tetrahydroxyflav-2-en-3-ol 3-O-β-D-glucoside was isolated from the seed coats of immature black soybeans (Glycine max (L.) Merr.). This compound is a reduced form of cyanidin 3-O-β-D-glucoside (cyanidin 3-G) which was obtained by reaction with hydrochloric acid. The molecule has reducing activity for a tetrazolium derivative (WST-1) in the presence of 1-methoxy-5-methylphenazinium methylsulfate (1-methoxy PMS) in a similar manner to NADH. The seed coats of immature black soybeans also contain epicatechin as a major constituent, while cyanidin 3-G and procyanidin B2 are present at lower concentrations. Immature brown soybeans did not contain 5,7,3',4'-tetrahydroxyflav-2-en-3-ol 3-O-β-D-glucoside, but did contain both epicatechin and procyanidin B2. Immature yellow soybeans contained none of them.

MeSH terms

  • Anthocyanins / analysis
  • Anthocyanins / chemistry
  • Anthocyanins / isolation & purification*
  • Biflavonoids / analysis
  • Biflavonoids / isolation & purification
  • Catechin / analysis
  • Catechin / isolation & purification
  • Glucosides / analysis
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glycine max / chemistry*
  • Hydrochloric Acid / chemistry
  • Proanthocyanidins / analysis
  • Proanthocyanidins / isolation & purification
  • Seeds / chemistry*

Substances

  • Anthocyanins
  • Biflavonoids
  • Glucosides
  • Proanthocyanidins
  • cyanidin-3-O-beta-glucopyranoside
  • procyanidin B2
  • Catechin
  • Hydrochloric Acid