Highly Polymerized Procyanidins in Brown Soybean Seed Coat with a High Radical-Scavenging Activity

1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity of the 70% aqueous acetone extract from the seed coat of the brown soybean variety, Akita-Zairai, was investigated. The activity of the seed coat of Akita-Zairai was much higher than that of three other reddish-brown varieties, but lower than that of two black varieties, and was closely dependent on the content of phenolic compounds. In the LH20 column chromatography of Akita-Zairai, high DPPH radical-scavenging activities were detected in the fractions eluted with MeOH and 70% aqueous acetone. Proanthocyanidins were also detected in fractions showing high radical-scavenging activities. Matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry analysis showed that the degree of polymerization (DP) of the procyanidins contained in the brown or black soybean seed coat was as high as DP30.