5,5′-Dicapsaicin, 4′-O-5-Dicapsaicin Ether, and Dehydrogenation Polymers with High Molecular Weights Are the Main Products of the Oxidation of Capsaicin by Peroxidase from Hot Pepper

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 10, 1996, Pages 3085-3089

  Bernal, María A ^a   Barceló, A Ros ^b  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b UNIVERSITY OF MURCIA   (Spain)

Author keywords

Capsaicin; Capsaicin oxidation products; Hot pepper; Peroxidase

Indexed keywords

CAPSICUM; CAPSICUM FRUTESCENS;

EID: 0008547429     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf950826y     Document Type: Article

References (17)

1. Bennett, D. J.; Kirby, G. W. Constitution and biosynthesis of capsaicin. J. Chem. Soc. C 1968, 442-446.
2. Bernal, M. A.; Calderón, A. A.; Pedreño, M. A.; Muñoz, R.; Ros Barceló, A.; Merino de Cáceres, F. Capsaicin oxidation by peroxidase from Capsicum annuum (var. annuum) fruits. J. Agric. Food Chem. 1993a, 41, 1041-1044.
3. Bernal, M. A.; Pedreño, M. A.; Calderón, A. A.; Muñoz, R.; Ros Barceló, A.; Merino de Cáceres, F. The subcellular localization of isoperoxidases in Capsicum annuum leaves and their different expression in vegetative and flowered plants. Ann. Bot. 1993b, 72, 415-421.
4. Bernai, M. A.; Calderón, A. A.; Pedreño, M. A.; Ferrer, M. A.; Merino de Cáceres, F.; Ros Barceló, A. Purification of a basic peroxidase isoenzyme from Capsicum fruits and the immunoinhibition of its capsaicin oxidation capacity by antibodies raised against horseradish peroxidase. Z. Lebensm. Unters. Forsch. 1994a, 199, 240-242.
5. Bernal, M. A.; Merino de Cáceres, F.; Ros Barceló, A. Histochemical localization of peroxidase in Capsicum fruits. Lebensm. Wiss. Technol. 1994b, 27, 197-198.
6. 6 from hot pepper. J. Agric. Food Chem. 1995, 43, 352-355.
7. Chung, N.; Aust, S. D. Inactivation of lignin peroxidase by hydrogen peroxide during the oxidation of phenols. Arch. Biochem. Biophys. 1995, 316, 851-855.
8. Evans, J. J.; Himmelsbach, D. S. Incorporation of peroxidase into synthetic lignin. J. Agric. Food Chem. 1991, 39, 830-832.
9. Ferrer, M. A.; Ros Barceló, A. Inactivation of cell wall acidic peroxidase isoenzymes during the oxidation of coniferyl alcohol in Lupinus. Phytochemistry 1994, 36, 1161-1163.
10. Hall, R. D.; Holden, M. A.; Yeoman, M. M. The accumulation of phenylpropanoids and capsaicinoid compounds in cell structures and whole fruit of the chilli pepper, Capsicum frutescens Mill. Plant Cell, Tissue Organ Cult. 1987, 8, 63-176.
11. Hapiot, P.; Pinson, J.; Neta, P.; Francesch, C.; Mhamdi, F.; Rolando, C.; Schneider, S. Mechanism of oxidative coupling of coniferyl alcohol. Phytochemistry 1994, 36, 1013-1020.
12. Iwai, K.; Suzuki, T.; Fujiwake, H. Formation and accumulation of pungent principle of hot pepper fruits, capsaicin and its analogues, in Capsicum annuum var. annuum cv. karayatsubusa at different growth stages after flowering. Agric. Biol. Chem. 1979, 43, 2493-2498.
13. Lai, Y. Z.; Sarkanen, K. V. Structural variation in dehydrogenation polymers of coniferyl alcohol. Cellul. Chem. Technol. 1975, 9, 239-245.
14. Leete, E.; Louden, M. C. L. Biosynthesis of capsaicin and dihydrocapsaicin in Capsicum frutescens. J. Am. Chem. Soc. 1968, 90, 6837-6841.
15. Sottomayor, M.; de Pinto, M. C.; Salema, R.; DiCosmo, F.; Pedreño, M. A.; Ros Barceló, A. The vacuolar localization of a basic peroxidase isoenzyme responsible for the synthesis of α-3,4-anhydro vinblastine in Catharanthus roseus (L.) G. Don leaves. Plant Cell Environ. 1996, 19, 761-767.
16. Sukrasno, N.; Yeoman, M. M. Phenylpropanoid metabolism during growth and development of Capsicum frutescens fruits. Phytochemistry 1993, 32, 839-844.
17. Weymouth, N.; Dean, J. F. D.; Eriksson, K. E. L. Synthesis and spectroscopic characterization of p-hydroxyphenyl, guaiacyl and syringyl lignin polymer models (DHPs). Nord. Pulp Pap. Res. J. 1993, 8, 344-349.