title: Synthesis of stable isotope-labeled precursors for the biosyntheses of capsaicinoids, capsinoids, and capsiconinoids.
abstract: Stable isotope-labeled precursors were synthesized for an analysis by liquid chromatography-tandem mass spectrometry (LC-MS/MS) to elucidate the biosynthetic flow of capsaicinoids, capsinoids, and capsiconinoids. [1'-(13)C][5-(2)H]-Vanillin was prepared by the condensation of guaiacol with [(13)C]-chloroform and a D(2)O treatment. Labeled vanillylamine, vanillyl alcohol, ferulic acid, and coniferyl alcohol were prepared from the labeled vanillin. The labeled vanillylamine was converted to labeled capsaicinoid in a crude enzyme solution extracted from pungent Capsicum fruits.
authors.affiliation: Graduate School of Nutritional and Environmental Sciences and Global COE Program, University of Shizuoka, Suruga-ku, Shizuoka, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Kobata
authors.forename: Makoto
authors.initials: M
authors.lastname: Mimura
authors.forename: Mai
authors.initials: M
authors.lastname: Sugawara
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Watanabe
mesh_terms: D001547:Benzaldehydes / Q000138:chemical synthesis*; D001592:Benzyl Alcohols / Q000138:chemical synthesis*; D001596:Benzylamines / Q000138:chemical synthesis*; D002211:Capsaicin / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D002212:Capsicum / Q000737:chemistry; D002247:Carbon Isotopes; D002625:Chemistry, Organic / Q000379:methods*; D002725:Chloroform / Q000737:chemistry; D002853:Chromatography, Liquid; D003373:Coumaric Acids / Q000138:chemical synthesis*; D017666:Deuterium Oxide; D006139:Guaiacol / Q000737:chemistry; D007553:Isotope Labeling / Q000379:methods*; D010636:Phenols / Q000138:chemical synthesis*; D010936:Plant Extracts / Q000378:metabolism*; D011355:Prodrugs / Q000138:chemical synthesis; D053719:Tandem Mass Spectrometry
chemical_list: D001547:Benzaldehydes; D001592:Benzyl Alcohols; D001596:Benzylamines; D002247:Carbon Isotopes; D003373:Coumaric Acids; D010636:Phenols; D010936:Plant Extracts; D011355:Prodrugs; C003754:vanillylamine; D006139:Guaiacol; D002725:Chloroform; C004999:ferulic acid; C100058:vanillin; C010559:coniferyl alcohol; D017666:Deuterium Oxide; D002211:Capsaicin; C024078:vanillyl alcohol