Reactivity of chalcones with 1-hydroxymethyl radicals

Radiation Research

Volumn 166, Issue 6, 2006, Pages 928-941

  Mokrini, Redouane ^a   Trouillas, Patrick ^a   Kaouadji, Mourad ^a   Champavier, Yves ^b   Houée Lévin, Chantal ^c   Fagnère, Catherine ^a   Duroux, Jean Luc ^a,b  

^a UNIVERSITÉ DE LIMOGES   (France)

^b UNIVERSITY OF LIMOGES   (France)

^c UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYMETHYL RADICAL; CHALCONE; HYDROXYL RADICAL; RADICAL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; FOOD PRESERVATION; GAMMA IRRADIATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOLYSIS; ULTRAVIOLET SPECTROSCOPY;

CHALCONES; FREE RADICALS; METHANOL;

EID: 33845356648     PISSN: 00337587     EISSN: None     Source Type: Journal    
DOI: 10.1667/RR0615.1     Document Type: Article

References (43)

1. W. M. Urbain, Food Irradiation (Food Science Technology). Academic Press, Orlando, FL, 1986.
2. J. Raffi, Identifying irradiated foods. TRAC-Trends Anal. Chem. 17, 226-233 (1998).
3. J. F. Diehl, Safety of Irradiated Foods, 2nd ed. Marcel Dekker, New York, 1995.
4. Wholesomeness of Irradiated Food. Report of a Joint FAO/IAEA/ WHO Expert Committee. WHO Technical Report Series, No. 659, World Health Organization, Geneva, 1981.
5. High-dose Irradiation: Wholesomeness of Food Irradiated with Doses above 10 kGy. Report of a Joint FAO/IAEA/WHO Expert Committee. WHO Technical Report Series, No. 890, World Health Organization, Geneva, 1997.
6. J. B. Harborne, Ed., The Flavonoids: Advances in Research Since 1986. Chapman & Hall, London, 1994.
7. G. Cioffi, L. M. Escobar, A. Braca and N. De Tommasi, Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria. J. Nat. Prod. 66, 1061-1064 (2003).
8. N. C. Cook and S. Samman, Flavonoids-chemistry, metabolism, cardioprotective effects, and dietary sources. J. Nutr. Biochem. 7, 66-76 (1996).
9. R. J. Anto, K. Sukumaran, G. Kuttan, M. N. Rao, V. Subbaraju and R. Kuttan, Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer Lett. 97, 33-37 (1995).
10. M. Lopez-Lazaro, Flavonoids as anticancer agents: Structure-activity relationship study. Curr. Med. Chem. Anticancer Agents 2, 691-714 (2002).
11. U. Wenzel, S. Kuntz, M. D. Brendel and H. Daniel, Dietary flavone is a potent apoptosis inducer in human colon carcinoma cells. Cancer Res. 60, 3823-3831 (2000).
12. H. K. Hsieh, T. H. Lee, J. P. Wang, J. J. Wang and C. N. Lin, Synthesis and anti-inflammatory effect of chalcones and related compounds. Pharm. Res. 15, 39-46 (1998).
13. S. J. Won, C. T. Liu, L. T. Tsao, J. R. Weng, H. H. Ko, J. P. Wang and C. N. Lin, Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur. J. Med. Chem. 40, 103-112 (2005).
14. Y. M. Lin, Y. Zhou, M. T. Flavin, L. M. Zhou, W. Nie and F. C. Chen, Chalcones and flavonoids as anti-tuberculosis agents. Bioorgan. Med. Chem. 10, 2795-2802 (2002).
15. A. L. Ahmad, A. B. Dowsett and D. A. Tyrrell, Studies of rhinovirus resistant to an antiviral chalcone, Antiviral Res. 8, 27-39 (1987).
16. T. Torigoo, M. Arisawa, S. Hoch, M. Fujiu and H. B. Mayuyama, Anti-mutagenic chalcones: Antagonizing the mutagenicity of benzo(a)pyrene on Salmonella typhimurium. Biochem. Biophys. Res. Commun. 112, 833-842 (1983).
17. K. Sukumaran and R. Kuttan, Screening of 11 ferns for cytotoxic and antitumor potential with special reference to Pityrogramma calomelanos. J. Ethnopharmacol. 34, 93-96 (1991).
18. R. J. Anto, K. Sukumaran, G. Kuttan, M. N. Rao, V. Subbaraju and R. Kuttan, Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer Lett. 97, 33-37 (1995).
19. - and α-hydroxyethyl radical in deaerated ethanol solution under γ-irradiation. Radiat. Phys. Chem. 45, 217-222 (1995).
20. 2-saturated ethanol solution. Radiat. Phys. Chem. 55, 285-291 (1999).
21. A. Marfak, P. Trouillas, D. P. Allais, C. A. Calliste, J. Cook-Moreau and J. L. Duroux, Reactivity of flavonoids with 1-hydroxyethyl radical: a γ-radiolysis study. Biochim. Biophys. Acta 1670, 28-39 (2004).
22. Z. Cai, H. Yongke and J. L. Wu, Hydroxylethylation of baicalin by γ-ray irradiation of baicalin in ethanol. Radiat. Phys. Chem. 47, 213-215 (1996).
23. I. B. Hryntsevich and O. I. Shadyro, Reactions of α-hydroxyethyl radicals with flavonoids of various structures. Bioorg. Med. Chem. Lett. 15, 4252-4255 (2005).
24. H. Fricke and E. J. Hart, In Radiation Dosimetry, Vol. II, Instrumentation (F. H. Attix, W. C. Roesch and E. Tochilin, Eds.), pp. 167-237. Academic Press, New York, 1966.
25. T. J. Mabry, K. R. Markham and M. B. Thomas, The Systematic Identification of Flavonoids. Springer-Verlag, Berlin, Heidelberg, New York, 1970.
26. D. N. Dhar, The Chemistry of Chalcones and Related Compounds. Wiley-Interscience, New York, 1981.
27. H. H. Szmant and J. A. Basso, The absorption spectra of substituted chalcones. J. Am. Chem. Soc. 74, 4397-4400 (1952).
28. B. Black and R. E. Lutz, Ultraviolet absorption spectra of chalcones. Identification of chromophores. J. Am. Chem. Soc. 77, 5134-5138 (1954).
29. G. R. Freeman, In The Radiolysis of Alcohols, Kinetics of Nonhomogeneous Processes: A Practical Introduction for Chemists, Biologists, Physicists, and Materials Scientists (G. R. Freeman, Ed.). pp. 73-101. Wiley-Interscience, New York, 1987.
30. J. H. Baxendale, Rate of reaction of solvated electrons with hydrogen ions in methanol. Int. J. Radiat. Phys. Chem. 4, 113-115 (1972).
31. N. Getoff, A. Ritter, F. Schwoerer and P. Bayer, Primary yields of methoxy and hydroxymethyl radicals resulting in the radiolysis of high purity methanol. Radiat. Phys. Chem. 41, 797-801 (1993).
32. J. Lind, A. Jowko and T. E. Eriksen, Methoxy radical production in methanol radiolysis. Radiat. Phys. Chem. 13, 159-163 (1979).
33. G. Wang and J. Wu, Selecting ethanol as a model organic solvent in radiation chemistry-4: Radiation chemistry of diallyl sulphide in ethanol solution. Radiat. Phys. Chem. 55, 25-34 (1999).
34. R. Mokrini, P. Trouillas, M. Kaouadji, Y. Champavier, C. Houée-Lévin, C. A. Calliste and J. L. Duroux, Radiolytic transformation of 2,2′,4′-trihydroxychalcone. Radiat. Res. 165, 730-740 (2006).
35. A. Marfak, P. Trouillas, D. P. Allais, C. A. Calliste and J. L. Duroux, Redox reactions obtained by γ irradiation of quercetin methanol solution are similar to in vivo metabolism. Radiat. Res. 159, 218-227 (2003).
36. A. Marfak, P. Trouillas, D. P. Allais, C. A. Calliste, J. Cook-Moreau and J. L. Duroux, Transformation mechanism of the antioxidant kaempferol into depsides. γ-Radiolysis study in methanol and ethanol. Radiat. Res. 160, 355-365 (2003).
37. C. A. Rice-Evans, N. J. Miller and G. Paganga, Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20, 933-956 (1996).
38. H. Y. Zhang, Y. M. Sun and D. Z. Chen, O-H bond dissociation energies of phenolic compounds are determined by field/inductive effect of resonance effect? A DFT study and its implication. QSAR 20, 148-152 (2001).
39. H. Y. Zhang, Y. M. Sun and X. L. Wang, Electronic effects on O-H proton dissociation energies of phenolic cation radicals: A DFT study. J. Org. Chem. 67, 2709-2712 (2002).
40. H. Y. Zhang, Y. M. Sun and X. L. Wang, Substituent effects on O-H bond dissociation enthalpies and ionization potentials of catechols: A DFT study and its implications in the rational design of phenolic antioxidants and elucidation of structure-activity relationships for flavonoid antioxidants. Chem. Eur. J. 9, 502-508 (2003).
41. M. Leopoldini, I. P. Pitarch, N. Russo and M. Toscano, Structure, conformation, and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study. J. Phys. Chem. A 108, 92-96 (2004).
42. P. Trouillas, P. Marsal, D. Siri, R. Lazzaroni and J. L. Duroux, A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: The specificity of the 3-OH site. Food Chem. 97, 679-688 (2005).
43. S. V. Jovanovic, S. Steenken, M. Tosic, B. Marjanovic and M. G. Simic, Flavonoids as antioxidants. J. Am. Chem. Soc. 116, 4846-4851 (1994).