title: Occurrence of stereoisomers of 1-(2'-pyrrolidinethione-3'-yl)- 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid in fermented radish roots and their different mutagenic properties.
abstract: Stereoisomers of the tetrahydro-beta-carboline derivative, 1-(2-pyrrolidinethione)-3-yl)-1,2,3,4-tetrahydro-beta-carboline- 3-carboxylic acid (PTCC), were formed from L-tryptophan with 4-methylthio-3-butenyl isothiocyanate, and their mutagenic properties and contents in different types of the radish products were studied. The isomers were identified as (1S*, 3S*, 3R*)- and (1R*, 3S*, 3R*)-PTCCs; the former was found as the major compound but had no mutagenic activity, while the latter was mutagenic toward Salmonella typhimurium TA 98 in the presence of a rat microsomal fraction. Both (1S*, 3S*, 3R*)- and (1R*, 3S*, 3R*)-PTCC were detected in a ratio of about 4:1 in a product fermented for 8 months, but only a trace was apparent in products manufactured within a few weeks.
authors.affiliation: Department of Food and Nutrition, Gunma Women's Junior College, Takasaki, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Ozawa
authors.forename: Y
authors.initials: Y
authors.lastname: Uda
authors.forename: H
authors.initials: H
authors.lastname: Matsuoka
authors.forename: M
authors.initials: M
authors.lastname: Abe
authors.forename: S
authors.initials: S
authors.lastname: Kawakishi
authors.forename: T
authors.initials: T
authors.lastname: Osawa
mesh_terms: D000818:Animals; D002243:Carbolines / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D005285:Fermentation; D005506:Food Contamination / Q000032:analysis*; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009152:Mutagenicity Tests; D009153:Mutagens / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D018517:Plant Roots / Q000737:chemistry / Q000633:toxicity; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D051381:Rats; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D013237:Stereoisomerism; D014675:Vegetables / Q000737:chemistry / Q000633:toxicity
chemical_list: C118238:1-(2'-pyrrolidinethione-3'-yl)-1,2,3,4-tetrahydrocarboline-3-carboxylic acid; D002243:Carbolines; D009153:Mutagens; D011759:Pyrrolidines