In vitro flavon-3-ol oxidation mediated by a B ring hydroxylation pattern

Chemical Research in Toxicology

Volumn 17, Issue 6, 2004, Pages 795-804

  Krishnamachari, Venkat ^a   Levine, Lanfang H ^b   Zhou, Chun ^a   Paré, Paul W ^a  

^a TEXAS TECH UNIVERSITY   (United States)

^b DYNAMAC CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' AZOBISISOBUTYRONITRILE; 3 HYDROXYFLAVONE; 3 METHOXYQUERCETIN; ANTIOXIDANT; BUTYRONITRILE; CATION; FLAVONOL DERIVATIVE; HYDROXYL GROUP; LUTEOLIN; QUERCETIN; UNCLASSIFIED DRUG;

ARTICLE; DIMERIZATION; HYDROXYLATION; OXIDATION; REACTION ANALYSIS; SPECTROSCOPY;

CHROMATOGRAPHY, LIQUID; DIMERIZATION; FLAVONOIDS; FLAVONOLS; HYDROXYLATION; LUTEOLIN; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METHYLATION; NITRILES; OXIDATION-REDUCTION;

EID: 3042842883     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx034242z     Document Type: Article

References (32)

1. Hollman, P. C. H., van Trijp, J. M. P., Buysman, M. N. C. P., Gaag, M. S. V. D., Mengelers, M. J. B., Vries, J. H. M., and Katan, M. B. (1997) Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man. FEBS Lett. 418, 152-156.
2. Geleijnse, J. M., Launer, L. J., van der Kurp, D. A. M., Hofman, A., and Witteman, J. C. M. (2002) Inverse association of tea and flavonoid intakes with incidence of myocardial infraction: the Rotterdam Study. Am. J. Clin. Nutr. 75, 880-886.
3. Laughton, M. J., Halliwell, B., Evans, P. J., and Hoult, J. R. S. (1989) Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin. Effects on lipid peroxidation, hydroxyl radical generation and bleomycin-dependent damage to DNA. Biochem. Pharmacol. 38, 2859-2865.
4. Bors, W., Heller, W., Michel, C., and Saran, M. (1990) Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Methods Enzymol. 186, 343-355.
5. Kano, K., Mabuchi, T., Uno, B., Esaka, Y., Tanaka, T., and Iinuma, M. (1994) Superoxide anion radical-induced dioxygenolysis of quercetin as a mimic of quercetinase. J. Chem. Soc., Chem. Commun. 5, 593-594.
6. Tournaire, C., Hocquaux, M., Beck, I., Oliveros, E., and Maurette, M. (1994) Activité anti-oxidante de flavonoïdes Ré activité avec le superoxyde de potassium en phase hété rogène. Tetrahedron 50, 9303-9314.
7. Krishnamachari, V., Levine, L. H., and Paré, P. W. (2002) Flavonoid oxidation by the radical generator AIBN: A unified mechanism for quercetin radical scavenging. J. Agric. Food Chem. 50, 4357-4363.
8. Ohashi, H., Kyogoku, T., Ishikawa, T., Kawase, S., and Kawai, S. (1999) Antioxidative activity of tree phenolic constituents 1: Radical-capturing reaction of flavon-3-ols with radical initiator. J. Wood Sci. 45, 53-63.
9. Ishikawa, T., Takagi, M., Kanou, M., Kawai, S., and Ohashi, H. (1999) Radical-capturing reaction of 5,7,3′,4′-tetramethylquercetin with the AIBN radical initiator. Biosci., Biotechnol., Biochem. 63, 173-177.
10. Marfak, A., Trouillas, P., Allais, D. P., Champavier, Y., Calliste, C. A., and Duroux, J. L. (2002) Radiolysis of quercetin in methanol solution: observation of depside formation. J. Agric. Food Chem. 50, 4827-4833.
11. Marfak, A., Trouillas, P., Allais, D. P., Champavier, Y., Calliste, C. A., and Duroux, J. L. (2003) Radiolysis of kaempferol in water/methanol mixtures. Evaluation of antioxidant activity of kaempferol and products formed. J. Agric. Food Chem. 51, 1270-1277.
12. Jorgensen, L. V., Cornett, C., Justesen, U., Skibsted, L. H., and Dragsted, L. O. (1998) Two-electron electrochemical oxidation of quercetin and kaempferol changes only the flavonoid C-ring. Free Radical Res. Commun. 29, 339-350.
13. Dangles, O., Fargeix, G., and Dufour, C. (1999) One-electron oxidation of quercetin and quercetin derivatives in protic and non protic media. J. Chem. Soc. Perkin Trans. 2, 1387-1395.
14. Awad, H. M., Boersma, M. G., Boeren, S., van Bladeren, P. J., Vervoort, J., and Rietjens, I. M. C. M. (2001) Structure-activity study on the quinone/quinone methide chemistry of flavonoids. Chem. Res. Toxicol. 14, 398-408.
15. Hirose, Y., Fujita, T., and Nakayama, M. (1999) Structure of doubly linked oxidative product of quercetin in lipid peroxidation. Chem. Lett. 8, 775-776.
16. Anand, N. K., Gupta, S. R., Jain, A. C., Mathur, S. K., Pankajamani, K. S., and Seshadri, T. R. (1962) Synthesis of certain partial methyl ethers of flavonols: Rhamnetin, 3-O-methyl quercetin, 3,3′-O-dimethyl quercetin, ombuin, 3,7-O-dimethyl gossypetin and reso-oxyayanin-A. J. Sci. Ind. Res. 21B, 322-329.
17. Smith, M. A., Neumann, R. M., and Webb, R. A. (1968) A modification of the Algar-Flynn-Oyamada preparation of flavonols. J. Heterocycl. Chem. 5, 425-426.
18. Ozawa, H., Okuda, T., Kawanishi, M., and Fujii, K. (1951) Synthesis of 3, 4-dihydroxy- 3-flavonol and related compounds. J. Pharm. Soc. Jpn. 71, 1178-1183.
19. Statistical Analysis Systems Institute, Inc. (2001) SAT/STAT User's Guide, Version 6.11, Vol. 1, Statistical Analysis Systems Institute Inc., Cary, NC.
20. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., and Stewart, J. J. P. (1985) The development and use of quantum-mechanical molecular-models. 76. AM1 - a new general-purpose quantum-mechanical molecular-model. J. Am. Chem. Soc. 107, 3902-3909.
21. 40 cluster. Phys. Chem. Chem. Phys. 4, 2546-2553.
22. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery, J. A., Jr., Stratmann, R. E., Burant, J. C., Dapprich, S., Millam, M. J., Daniels, A. D., Kudin, K. N., Strain, M. C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q., Morokuma, K., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Cioslowski, J., Ortiz, J. V., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Andres, J. L., Gonzalez, C., Head-Gordon, M., Replogle, E. S., and Pople, J. A. (1998) Gaussian 98, Rev. A.11, Gaussian, Inc., Pittsburgh PA.
23. The heats of formation were calculated using CS MOPAC Pro, MOPAC 97, Cambridge Soft Corporation, 1997.
24. Matsuura, T., Matsushima, H., and Nakashima, R. (1970) Photoinduced reactions XXXVI, Photosensitized oxygenation of 3-hydroxyflavones as a nonenzymatic model for quercetinase. Tetrahedron 26, 435-443.
25. Dangles, O., Dufour, C., and Bret, S. (1999) Flavonol-serum albumin complexation. Two electron oxidation of flavonols and their complexes with serum albumin. J. Chem. Soc., Perkin Trans. 2, 737-744.
26. Makris, D., and Rossiter, J. T. (2002) An investigation on structural aspects influencing product formation in enzymic and chemical oxidation of quercetin and related flavonols. Food Chem. 77, 177-185.
27. Awad, H. M., Boersma, M. G., Boeren, S., van Bladeren, P. J., Vervoort, J., and Rietjens, I. M. C. M. (2002) The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methide is pH-dependent. Chem. Res. Toxicol. 15, 343-351.
28. Awad, H. M., Boersma, M. G., Vervoort, J., and Rietjens, M. C. M. (2000) Peroxidase-catalyzed formation of quercetin quinone methide-gluthione adducts. Arch. Biochem. Biophys. 378, 224-233.
29. Jungbluth, G., Rühling, I., and Ternes, W. (2000) Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media. J. Chem. Soc., Perkin Trans 2, 1946-1952.
30. Utaka, M., and Takeda, A. (1985) Copper(II)-catalyzed oxidation of quereetin and 3-hydroxyflavone. J. Chem. Soc. Chem. Commun. 24, 1824-1826.
31. Balogh-Hergovich, E., and Speier, G. (1992) Oxidation of 3-hydroxyflavones in the presence of copper(I) and copper(II) chlorides. J. Mol. Catal. 71, 1-5.
32. Arora, A., Valcic, S., Lorenzo, S., Nair, M. G., Timmermann, B. N., and Liebler, D. C. (2000) Reactions of genistein with alkyl peroxyl radicals. Chem. Res. Toxicol. 13, 638-645.