title: Isolation of a reduced form of cyanidin 3-O-β-D-glucoside from immature black soybean (Glycine max (L.) Merr.) and its reducing properties.
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.
authors.affiliation: Department of Bioscience and Biotechnology, Faculty of Bioenvironmental Science, Kyoto Gakuen University, Kyoto, Japan. fukami@kyotogakuen.ac.jp
authors.forename: Harukazu
authors.initials: H
authors.lastname: Fukami
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Yano
authors.forename: Takashi
authors.initials: T
authors.lastname: Iwashita
mesh_terms: D000872:Anthocyanins / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D044946:Biflavonoids / Q000032:analysis / Q000302:isolation & purification; D002392:Catechin / Q000032:analysis / Q000302:isolation & purification; D005960:Glucosides / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification*; D006851:Hydrochloric Acid / Q000737:chemistry; D044945:Proanthocyanidins / Q000032:analysis / Q000302:isolation & purification; D012639:Seeds / Q000737:chemistry*; D013025:Glycine max / Q000737:chemistry*
chemical_list: D000872:Anthocyanins; D044946:Biflavonoids; D005960:Glucosides; D044945:Proanthocyanidins; C462279:cyanidin-3-O-beta-glucopyranoside; C479580:procyanidin B2; D002392:Catechin; D006851:Hydrochloric Acid