title: Potent production of capsaicinoids and capsinoids by Capsicum peppers.
abstract: The fundamental structure of capsinoids is a fatty acid ester with vanillyl alcohol, whereas in capsaicinoids, a fatty acid amide is linked to vanillylamine. To clarify the relationship between their biosynthesis in Capsicum plants, we carried out an in vivo tracer experiment using stable isotopically labeled putative precursors. Liquid chromatography-tandem mass spectrometry was used to measure the uptake of isotopes into metabolites after injection of the labeled precursors into intact fruits of a pungent cultivar, Peru, and a non-pungent cultivar, CH-19 Sweet. Labeled vanillylamine was incorporated into capsaicinoids in both cultivars. While labeled vanillyl alcohol was incorporated into capsinoids in both cultivars, the accumulation of intact capsaicinoids in Peru was suppressed by over 60% after administration of vanillyl alcohol. In Peru, labeled vanillin was converted to both vanillylamine and, in 5-fold excess, vanillyl alcohol. Moreover, labeled vanillin was converted exclusively to vanillyl alcohol in CH-19 Sweet. These data are consistent with the incorporation of labeled vanillin into capsaicinoids and capsinoids in both cultivars. We conclude that pungent cultivars are highly potent producers of vanillyl alcohol that is incorporated into capsinoids and that biosynthesis of capsinoids is catalyzed by capsaicin synthase.
authors.affiliation: Graduate School of Integrated Pharmaceutical and Nutritional Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Kobata
authors.forename: Mai
authors.initials: M
authors.lastname: Sugawara
authors.forename: Makoto
authors.initials: M
authors.lastname: Mimura
authors.forename: Susumu
authors.initials: S
authors.lastname: Yazawa
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Watanabe
mesh_terms: D000577:Amides / Q000737:chemistry / Q000378:metabolism*; D001547:Benzaldehydes / Q000737:chemistry / Q000378:metabolism; D001592:Benzyl Alcohols / Q000737:chemistry / Q000378:metabolism; D001596:Benzylamines / Q000737:chemistry / Q000378:metabolism; D053898:Biosynthetic Pathways; D002211:Capsaicin / Q000737:chemistry / Q000378:metabolism*; D002212:Capsicum / Q000737:chemistry / Q000378:metabolism*; D002396:Catechols / Q000737:chemistry / Q000378:metabolism*; D007553:Isotope Labeling; D010936:Plant Extracts / Q000096:biosynthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D001547:Benzaldehydes; D001592:Benzyl Alcohols; D001596:Benzylamines; D002396:Catechols; D010936:Plant Extracts; C003754:vanillylamine; C100058:vanillin; D002211:Capsaicin; C024078:vanillyl alcohol