Free radical generation in rosmarinic acid investigated by electron paramagnetic resonance spectroscopy

Free Radical Research

Volumn 43, Issue 1, 2009, Pages 47-57

  Pirker, Katharina F ^a   Kay, Christopher W M ^b   Stolze, Klaus ^c   Tunega, Daniel ^d,e   Reichenauer, Thomas ^a   Goodman, Bernard ^a,f  

^a ARC SEIBERSDORF RESEARCH GMBH   (Austria)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF VETERINARY MEDICINE   (Austria)

^d UNIVERSITY OF VIENNA   (Austria)

^e UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^f GUANGXI UNIVERSITY   (China)

Author keywords

Auto oxidation; EPR spectroscopy; Free radical; Rosmarinic acid; Superoxide anion radical

Indexed keywords

FREE RADICAL; ROSMARINIC ACID;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; OXIDATION; PH;

ANTIOXIDANTS; CINNAMATES; DEPSIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; OXIDANTS; OXIDATION-REDUCTION;

EID: 63349107784     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760802585236     Document Type: Article

References (26)

1. Rice-Evans, CA, Miller, NJ and Paganga, G. (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med, 20, pp. 933-956.
2. Miller, E. and Schreier, P. (1985) Studies on flavonol degradation by peroxidase (donor: H2O2-oxidoreductase, EC 1.11.1.7): Part 1-Kaempferol. Food Chem, 17, pp. 143-154.
3. Pirker, KF, Stolze, K., Reichenauer, TG, Nohl, H. and Goodman, BA. (2006) Are the biological properties of kaempferol determined by its oxidation products?. Free Radic Res, 40, pp. 513-521.
4. Cotelle, N., Bernier, J-L, Catteau, J-P, Pommery, J., Wallet, J-C and Gaydou, EM. (1996) Antioxidant properties of hydroxy-flavones. Free Radic Biol Med, 20, pp. 35-43.
5. Pedersen, JA. (2000) Distribution and taxonomic implications of some phenolics in the family Lamiaceae determined by ESR spectroscopy. Biochem Syst Ecol, 28, pp. 229-253.
6. Berger, A. (2001) Versuche zur Klonierung der Rosmarinsauresynthase und anderer Gene der Rosmarinsaure-Biosynthese aus Coleus blumei [dissertation]. Heinrich-Heine-Universitat, Dusseldorf (D)
7. Bors, W., Michel, C., Stettmaier, K., Lu, Y. and Foo, LY. (2004) Antioxidant mechanisms of polyphenolic caffeic acid oligomers, constituents of Salvia officinalis. Biol Res, 37, pp. 301-311.
8. Cao, H., Cheng, W-X, Li, C., Pan, X-L, Xie, X-G and Lie, T-H. (2005) DFT study on the antioxidant activity of rosmarinic acid. J Mol Struc-Theochem, 719, pp. 177-183.
9. Milic, BL and Milic, NB. (1998) Protective effects of spice plants on mutagenesis. Phytother Res, 12, pp. S3-S6.
10. Ito, H., Miyazaki, T., Ono, M. and Sakurai, H. (1998) Antiallergic activities of rabdosiin and its related compounds: Chemical and biochemical evaluations. Bioorgan Med Chem, 6, pp. 1051-1056.
11. Maegawa, Y., Sugino, K. and Sakurai, H. (2007) Identification of free radical species derived from caffeic acid and related polyphenols. Free Radic Res, 41, pp. 110-119.
12. Mouhajir, F., Pedersen, JA, Rejdali, M. and Towers, GHN. (2001) Phenolics in Moroccan medicinal plant species as studied by electron spin resonance spectroscopy. Pharm Biol, 39, pp. 391-398.
13. Pedersen, JA. (1978) Naturally occurring quinols and quinones studied as semiquinones by electron spin resonance. Phytochemistry, 17, pp. 775-778.
14. Petrucci, R., Astolfi, P., Greci, L., Firuzi, O., Saso, L. and Marrosu, G. (2007) A spectroelectrochemical and chemical study on oxidation of hydroxycinnamic acids in aprotic medium. Electrochim Acta, 52, pp. 2461-2470.
15. Bors, W., Michel, C., Stettmaier, K., Lu, Y. and Foo, LY. (2003) Pulse radiolysis, electron paramagnetic resonance spectroscopy and theoretical calculations of caffeic acid oligomer radicals. Biochim Biophys Acta, 1620, pp. 97-107.
16. Miura, T., Muraoka, S. and Fujimoto, Y. (2003) Inactivation of creatine kinase induced by quercetin with horseradish peroxidase and hydrogen peroxidase: Pro-oxidative and anti-oxidative actions of quercetin. Food Chem Toxicol, 41, pp. 759-765.
17. Blank, I., Pascual, EC, Devaud, S., Fay, LB, Stadler, RH, Yeretzian, C. and Goodman, BA. (2002) Degradation of the coffee flavor compound furfuryl mercaptan in model Fenton-type reaction systems. J Agr Food Chem, 50, pp. 2356-2364.
18. Valentine, JS, Miksztal, AR and Sawyer, DT. (1984) Methods for the study of superoxide chemistry in nonaqueous solutions. Methods Enzymol, 105, pp. 71-81.
19. Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Montgomery Jr, JA, Vreven, T., Kudin, KN, Burant, JC, Millam, JM, Iyengar, SS, Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, GA, Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, JE, Hratchian, HP, Cross, JB, Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, RE, Yazyev, O., Austin, AJ, Cammi, R., Pomelli, R., Ochterski, JW, Ayala, PY, Morokuma, K., Voth, GA, Salvador, P., Dannenberg, JJ, Zakrzewski, VG, Dapprich, S., Daniels, AD, Strain, MC, Farkas, O., Malick, DK, Rabuck, AD, Raghavachari, K., Foresman, JB, Ortiz, JV, Cui, Q., Baboul, AG, Clifford, S., Cioslowski, J., Stefenov, BB, Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, RL, Fox, DJ, Keith, T., Al-Laham, MA, Peng, CY, Nanayakkara, A., Challacombe, M., Gill, PMW, Johnson, B., Chen, W., Wong, MW, Gonzalez, C. and Pople, JA. (2004) Gaussian 03, Revision C.02, Gaussian, Inc, Wallingford, CT
20. Pedersen, JA and Ollgaard, B. (1982) Phenolic acids in the genus Lycopodium. Biochem Syst Ecol, 10, pp. 3-9.
21. Ashworth, P. (1976) Electron spin resonance studies of structure and conformation in anion radicals formed during the autoxidation of hydroxylated coumarins. J Org Chem, 41, pp. 2920-2927.
22. Dixon, WT, Moghimi, M. and Murphy, D. (1975) Electron spin resonance study of the stereochemistry of radicals related to cinnamic acid. J Chem Soc Perk T 2, pp. 1189-1191.
23. Buettner, GR and Oberley, LW. (1978) Considerations in the spin trapping of superoxide and hydroxyl radical in aqueous systems using 5,5-dimethyl-1-pyrroline-1-oxide. Biochem Biophys Res Co, 83, pp. 69-74.
24. Masuoka, N., Isobe, T. and Kubo, I. (2006) Antioxidants from Rabdosia japonica. Phytother Res, 20, pp. 206-213.
25. Mondal, MS and Mitra, S. (1996) The inhibition of bovine xanthine oxidase activity by Hg2+ and other metal ions. J Inorg Biochem, 62, pp. 271-279.
26. Jakopitsch, C., Wanasinghe, A., Jantschko, W., Furtmuller, PG and Obinger, C. (2005) Kinetics of interconversion of ferrous enzymes, compound II and compound III, of wild-type Synechocystis catalase-peroxidase and Y249F. J Biol Chem, 280, pp. 9037-9042.