Specific Synthesis of 5,5‘-Dicapsaicin by Cell Suspension Cultures of Capsicum annuum Var. annuum (Chili Jalapeño Chigol) and Their Soluble and NaCl-Extracted Cell Wall Protein Fractions

• Published in: Journal of agricultural and food chemistry 2004-02, Vol.52 (4), p.972-979
• Main Authors: Martínez-Juárez, Víctor M, Ochoa-Alejo, Neftali, Lozoya-Gloria, Edmundo, Villarreal-Ortega, María L, Ariza-Castolo, Armando, Esparza-García, Fernando J, Calva-Calva, Graciano
• Format: Article
• Language: English
• Subjects: Biological and medical sciences; Capsaicin - analogs & derivatives; Capsaicin - metabolism; Capsicum - metabolism; Cell Wall - chemistry; Cells, Cultured; Food industries; Fruit and vegetable industries; Fundamental and applied biological sciences. Psychology; Magnetic Resonance Spectroscopy; Plant Extracts - chemistry; Plant Proteins - metabolism; Sodium Chloride
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf035214p

HPLC-UV, 1H NMR, 13C NMR, and 1H−1H COSY analyses revealed that exogenous capsaicin was specifically converted into 5,5‘-dicapsaicin by both cell suspension cultures of Capsicum annuum var. annuum (chili Jalapeño chigol) and their soluble and NaCl-extracted cell wall protein fractions under oxidative conditions. In cell suspension cultures 5,5‘-dicapsaicin was found only in biomass of capsaicin-fed cultures. This compound has not been detected before either in fresh fruits or in in vitro cultures of Capsicum. The transformation of capsaicin by different protein fractions revealed that most of the enzymatic activity was located in the NaCl-extracted, or ionic cell wall bound, protein, and that it was strictly dependent on H2O2. These results might in part explain some previously described features of capsaicin production by in vitro cultures of Capsicum. The implications of the results regarding the catabolism of capsaicinoids are discussed. Keywords: Capsaicin; 5,5‘-dicapsaicin; capsaicinoids; Capsicum; chili pepper; capsaicin catabolism; capsaicin degradation; 5,5‘-dicapsaicin NMR