Evaluation of the structure-activity relationship of flavonoids as antioxidants and toxicants of zebrafish larvae

Food Chemistry

Volumn 134, Issue 2, 2012, Pages 717-724

  Chen, Yau Hung ^a   Yang, Zhi Shiang ^a   Wen, Chi Chung ^a   Chang, Yeong Sheng ^a   Wang, Bo Cheng ^a   Hsiao, Chih Ang ^a   Shih, Tzenge Lien ^a  

^a TAMKANG UNIVERSITY   (Taiwan)

Author keywords

Antioxidant; Fin; Flavone; QSAR; UV; Zebrafish

Indexed keywords

ANTIOXIDANT; FIN; FLAVONE; QSAR; UV; ZEBRAFISH;

COMPUTATIONAL CHEMISTRY; FINS (HEAT EXCHANGE); FORCED CONVECTION; SCAVENGING; TOXICITY;

FLAVONOIDS;

3',4' DIHYDROXYFLAVONE; 3',4',5,7 DIHYDROXYFLAVONE; 3,6 DIHYDROXYFLAVONE; 6 AMINOFLAVONE; 6 METHOXYFLAVONE; 7 AMINOFLAVONE; 7 HYDROXYFLAVONE; 7 METHOXYFLAVONE; 7,8 DIHYDROXYFLAVONE; CHRYSIN; FLAVONE; FLAVONOID; KAEMPFEROL; MORIN; MYRICETIN; QUERCETIN; REACTIVE OXYGEN METABOLITE; RUTOSIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; EMBRYO; FIN (ORGAN); LARVAL STAGE; LD 50; NONHUMAN; PREDICTIVE VALUE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RADIATION EXPOSURE; ULTRAVIOLET B RADIATION; ZEBRA FISH;

ANIMALS; ANTIOXIDANTS; BIOLOGICAL ASSAY; FLAVONES; FLAVONOIDS; LARVA; STRUCTURE-ACTIVITY RELATIONSHIP; ZEBRAFISH;

DANIO RERIO;

EID: 84862822767     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.02.166     Document Type: Article

References (30)

1. T. Akama, Y. Shida, T. Sugaya, H. Ishida, K. Gomi, and M. Kasai Novel 5-aminoflavone derivatives as specific antitumor agents in breast cancer Journal of Medicinal Chemistry 39 1996 3461 3496
2. B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, and M. Karplus CHARMM: A program for macromolecular energy, minimisation, and dynamics calculations Journal of Computational Chemistry 4 1983 187 217
3. Chang, Y. S., Yang, L. L., & Wang, B. C. (2010). Pharmacophore modeling of tyrosine kinase inhibitors: 4-anilinoquinazoline derivatives. Journal of the Chinese Chemical Society, 57, 916-924.
4. Y.H. Chen, W.C. Lee, C.F. Liu, and H.J. Tsai Molecular structure, dynamic expression and promoter analysis of zebrafish (Daniorerio) myf-5 gene Genesis 29 2001 22 35
5. Y.H. Chen, Y.T. Lin, and G.H. Lee Novel and unexpected functions of zebrafishCCAAT box binding transcription factor (NF-Y) B subunit during cartilages development Bone 44 2009 777 784
6. Chen, Y. H., Wen, C. C., Lin, C. Y., Chou, C. Y., Yang, Z. S., & Wang, Y. H. (2011). UV-Induced fin damage in zebrafish as a system for evaluating the chemopreventive potential of broccoli and cauliflower extracts. Toxicology Mechanisms and Methods, 21, 63-69.
7. S. Chirumbolo The role of quercetin, flavonols and flavones in modulating inflammatory cell function Inflammation Allergy Drug Targets 9 2010 263 285
8. lck Journal of Natural Products 54 1991 1345 1352
9. M. Cushman, H. Zhu, R.L. Geahlen, and A.J. Kraker Synthesis and biochemical evaluation of a series of aminoflavones as potential inhibitors of protein-tyrosine kinases p56lck, EGFr, and p60v-src Journal of Medicinal Chemistry 37 1994 3353 3362
10. D. Dauzonne, B. Folléas, L. Martines, and G.G. Chabot Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones European Journal of Medicinal Chemistry 32 1997 71 82
11. B.L. Deng, J.A. Lepoivre, and G. Lemire Synthesis of 7-vinylflavone and 7-aminoflavone by palladium-catalyzed coupling reactions European Journal of Organic Chemistry 10 1999 2683 2688
12. P.R. Duchowicz, M.G. Vitale, E.A. Castro, M. Fernández, and J. Caballero QSAR analysis for heterocyclic antifungals Bioorganic & Medicinal Chemistry 15 2007 2680 2689
13. Gao, H., & Kawabata, J. (2005). α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl- containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors. Bioorganic & Medicinal Chemistry, 13, 1661-1671.
14. H. Göker, G. Ayhan, M. Tunqbilek, R. Ertan, G. Leoncini, and R. Garzoglio Synthesis and antiaggregator activity of some new derivatives of 4H-1-benzopyran-4-one European Journal of Medicinal Chemistry 30 1995 561 567
15. Harborne, J. B., & Williams, C. A. (2000). Advances in flavonoid research since 1992. Phytochemistry, 55, 481-504.
16. B.H. Havsteen The biochemistry and medical significance of flavonoids Pharmacology & Therapeutics 96 2002 67 202
17. K.E. Heim, A.R. Tagliaferro, and D.J. Bobilya Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships Journal of Nutritional Biochemistry 13 2002 572 584
18. Y. Katsuyama, N. Funa, I. Miyahisa, and S. Horinouchi Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli Chemistry & Biology 14 2007 613 621
19. Kimmel, C., Ballard, W. W., Kimmel, S. R., Ullmann, B., & Schilling, T.F. (1995). Stages of embryonic development in the zebrafish. Developmental Dynamics, 203, 253-310.
20. Lee, E. R., Kang, Y. J., Kim, J. H., Lee, H. T., & Cho, S. G. (2005). Modulation of apoptosis in HaCaT keratinocytes via differential regulation of ERK signaling pathway by flavonoids. Journal of Biological Chemistry, 280, 31498-31507.
21. Lee, E. R., Kim, J. H., Kang, Y. J., & Cho, S. G. (2007). The anti-apoptotic and anti-oxidant effect of eriodictyol on UV-induced apoptosis in keratinocytes. Biological & Pharmaceutical Bulletin, 30, 32-37.
22. G.H. Lee, M.Y. Chang, C.H. Hsu, and Y.H. Chen Essential roles of basic helix-loop-helix transcription factors, Capsulin and Musculin, during craniofacial myogenesis of zebrafish Cellular and Molecular Life Sciences 68 2011 4065 4078
23. Liao, H. R., Chang, Y. S., Lin, Y. C., Yang, L. L., Chou, Y. M., & Wang, B. C. (2006). QSAR analysis of the lipid peroxidation inhibitory activity with structure and energetic of 36 flavonoids derivatives. Journal of the Chinese Chemical Society, 53, 1251-1261.
24. Liao, Y. F., & Chen, Y. H. (2010). Zebrafish is emerging to be a model to find sun-protective compounds. Household & Personal Care Today, 4, 6-8.
25. A. Mazur, D. Bayle, C. Lab, E. Rock, and Y. Rayssiguier Inhibitory effect of procyanidin-rich extracts on LDL oxidation in vitro Atherosclerosis 145 1999 421 422
26. M. Ono, N. Yoshida, K. Ishibashi, M. Haratake, Y. Arano, and H. Mori Radioiodinated flavones for in vivo imaging of beta-amyloid plaques in the brain Journal of Medicinal Chemistry 48 2005 7253 7260
27. Shao, Z. H., Li, C. Q., VandenHoek, T. L., Becker, L. B., Schumacker, P. T., Wu, J. A., Attele, A. S., & Yuan, C. S. (1999). Extract from ScutellariabaicalensisGeorgi attenuates oxidant stress in cardiomyocytes. Journal of Molecular and Cellular Cardiology, 10, 1885-1895.
28. A. Takechi, H. Tokikawa, H. Miyake, and M. Sasaki Synthesis of 3-aminoflavones from 3-hydroxyflavones via 3-tosyloxy- or 3-mesyloxyflavones Chemistry Letters 35 2006 128 129
29. Tsai, I. T., Yang, Z. S., Lin, Z. Y., Wen, C. C., Cheng, C. C., & Chen, Y. H. (in press). Flavone is efficient to protect zebrafish fins from UV-induced damages. Drug and Chemical Toxicology.
30. Wang, Y. H., Wen, C. C., Yang, Z. S., Cheng, C. C., Tsai, J. N., Ku, C. C., Wu, H. J., & Chen, Y. H. (2009). Development of a whole-organism model to screen new compounds for sun protection. Marine Biotechnology, 11, 419-429.