Polyunsaturated fatty acid-derived chromones exhibiting potent antioxidant activity

Chemistry and Physics of Lipids

Volumn 170-171, Issue , 2013, Pages 41-45

  Mohamed, Yasser M A ^a   Vik, Anders ^a   Hofer, Tim ^b   Andersen, Jeanette Hammer ^b   Hansen, Trond Vidar ^a  

^a UNIVERSITY OF OSLO   (Norway)

^b UNIVERSITY OF TROMSØ   (Norway)

Author keywords

Antioxidants; Polyunsaturated fatty acids; Reactive oxygen species; Synthesis

Indexed keywords

2 ((5 HYDROXY 2 ((4Z,7Z,10Z,13Z,16Z) NONADECA 4,7,10,13,16 PENTAEN 1 YL) 4 OXY)ACETIC ACID; 5,7 DIHYDROXY 2 ((4Z,7Z,10Z,13Z,16Z) NONADECA 4,7,10,13,16 PENTAEN 1 YL) 4H CHROMEN 4 ONE; 5,7 DIHYDROXY 2 (4Z,7Z,10Z,13Z,16Z NONADECAPENTAENYL; 5,7 DIHYDROXY 2 NONADECYL 4H CHROMEN 4 ONE; 5,7 DIMETHOXY 2 ((4Z,7Z,10Z,13Z,16Z) NONADECA 4,7,10,13,16 PENTAEN 1 YL) 4H CHROMEN ONE; 5,7 DIMETHOXY 2 NONADECYL 4H CHROMEN 4 ONE; CHROMONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL ASSAY; HUMAN; HUMAN CELL; IC 50; LIPID PEROXIDATION; PRIORITY JOURNAL; SYNTHESIS;

ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; BIOLOGICAL PRODUCTS; CELL DEATH; CELL LINE, TUMOR; CELL PROLIFERATION; CHROMONES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; FATTY ACIDS, UNSATURATED; HEP G2 CELLS; HUMANS; LIPID PEROXIDATION; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84875972624     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2013.03.003     Document Type: Article

References (38)

1. H.F. Anwar, and T.V. Hansen First total synthesis of a polyunsaturated chromone metabolite isolated from the brown algae Zonaria tournefortii Organic Letters 11 2009 587 588
2. J.W. Blunt, B.R. Copp, R.A. Kayzers, M.H.G. Munro, and M.R. Prinsep Marine natural products Natural Product Reports 29 2012 144 222
3. A.J. Blackman, G.I. Rogers, and J.K. Volkman Phloroglucinol derivatives from three australian marine algae of the genus Zonaria Journal of Natural Products 51 1988 158 160
4. O. Blokhina, E. Virolainen, and K.V. Fagerstedt Antioxidants, oxidative damage and oxygen depriviation stress: a review Annals of Botany 91 2003 179 194
5. W. Bors, W. Heller, C. Michel, and M. Saran Flavonoids as antioxidants: determination of radical-scavenging efficiencies Methods in Enzymology 186 1990 343 355
6. B. Drew, and C. Leeuwenburgh Aging and the role of reactive nitrogen species Annals of the New York Academy of Science 959 2002 66 81
7. M. Dueñas, S. González-Manzano, A. González- Paramás, and C. Santos-Buelga Antioxidant evaluation of O-methylated metabolites of catechin, epicatechin and quercetin Journal of Pharmaceutical and Biomedical Analysis 51 2010 443 449
8. M. El Hattab, L. Piovetti, and C.E. Chitour Etude Chimique de l'algue brune Zonaria Tournefortii lamouroux recoltee sur les côtes Algeriennes Journal de la Société Algérienne de Chimie 16 2006 69 78
9. I. Erlund, M.L. Silaste, G. Alfthan, M. Rantala, Y.A. Kesäniemi, and A. Aro Plasma concentrations of the flavonoids hesperetin, naringenin and quercetin in human subjects following their habitual diets, and diets high or low in fruit and vegetables European Journal of Clinical Nutration 56 2002 891 898
10. T.V. Hansen, and L. Skattebøl Syntheses of two cytotoxic polyunsaturated pyrrole metabolites of the marine sponge Mycale micracanthoxea Tetrahedron Letters 45 2004 2809 2811
11. T.V. Hansen, and Y. Stenstrøm First total synthesis of (-)-aplyolide A Tetrahedron: Asymmetry 12 2001 1407 1409
12. T.V. Hansen, and Y.A. Stenstrøm Facile formal synthesis of volicitin Synthetic Communications 30 2000 2549 2557
13. B. Halliwell Role of free radicals in the neurodegenerative diseases: therapeutic implications for antioxidant treatment Drugs and Aging 18 2001 685 716
14. A.L. Harvey Natural products in drug discovery Drug Discovery 13 2008 894 901
15. P.C.H. Hollman, M.V.D. Gaag, M.J.B. Mengelers, J.M.P. van Trijp, J.H.M. de Vries, and M.B. Katan Absorption and disposition kinetics of the dietary antioxidant quercetin in man Free Radical Biology and Medicine 21 1996 703 707
16. T. Hofer, T.E. Eriksen, E. Hansen, I. Varmedal, I.-J. Jensen, J. Hammer-Andersen, and R.L. Olsen Cellular and chemical assays for discovery of novel antioxidants in marine organisms S. Basu, L. Wiklund, Studies on Experimental Models, Springer Science series Oxidative Stress in Applied Basic Research and Clinical Practice 2011 978-1-60761-955-0 637 658
17. D. Huang, B. Ou, M. Hampsh-Woodill, J.A. Flanagan, and E.K. Deemer Development and validation of oxygen radical absorbance capacity assay for lipophilic antioxidants using randomly methylated β-cyclodextrin as the solubility enhancer Journal of Agricultural and Food Chemistry 50 2002 1815 1821
18. M.G. Jakobsen, A. Vik, and T.V. Hansen Concise syntheses of three ω-3 polyunsaturated fatty acids Tetrahedron Letters 53 2012 5837 5839
19. J.-M. Kornprobst Encylopedia of Marine Natural Products. vols. 1-3 2010 Wiley-VCH Weinheim
20. V. Lobo, A. Patil, A. Phatak, and N. Chandra Free radicals, antioxidants and functional foods: impact on human health Pharmacognosy Reviews 4 2010 118 126
21. Y.M.A. Mohamed, and T.V. Hansen Synthesis of methyl (5Z,8Z,10E,12E,14Z) eicosapentaenoate Tetrahedron Letters 52 2011 1057 1059
22. Y.M.A. Mohamed, and T.V. Hansen Synthesis of mycalazol and mycalazal analogs with potent antiproliferating activities Pure and Applied Chemistry 83 2011 489 493
23. W.R. Markesbery, and M.A. Lovell DNA oxidation in Alzheimer's disease Antioxidants and Redox Signaling 8 2006 2039 2045
24. W.R. Markesbery Oxidative stress hypothesis in Alzheimer's Disease Free Radical Biology and Medicine 23 1997 134 147
25. W.R. Markesbery Oxidative alterations in Alzheimer's disease Brain Pathology 9 1999 133 146
26. M.D. Nunzio, V. Valli, and A. Bordoni Pro- and anti-oxidant effects of polyunsaturated fatty acid supplementation in HepG2 cells Prostaglandins, Leukotrienes and Essential Fatty Acids 85 2011 121 127
27. K. Odlo, J. Hentzen, J.F. Chabert, S. Ducki, O.A.B.S.M. Gani, I. Sylte, M. Skrede, V.A. Flørenes, and T.V. Hansen 1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin Bioorganic and Medicinal Chemistry 16 2008 4829 4838
28. C. Park, H.-S. So, C.-H. Shin, S.-H. Baek, B.-S. Moon, S.-H. Shin, H.-S. Lee, D.-W. Lee, and R. Park Quercetin protects the hydrogen peroxide-induced apoptosis via inhibition of mitochondrial dysfunction in H9c2 cardiomyoblast cells Biochemical Pharmacology 66 2003 1287 1295
29. C.L. Rock, R.A. Jacob, and P.E. Bowen Update on the Biological Characteristics of the Antioxidant Micronutrients: vitamin C, vitamin E, and the cartenoids Journal of the American Dietetic Association. 96 1996 693 702
30. C.N. Serhan, and N.A. Petasis Resolvins and protectins in inflammation resolution Chemical Reviews 111 2011 5922 5943
31. M. Shimazawa, Y. Nakajima, Y. Mashima, and H. Hara Docosahexaenoic acid (DHA) has neuroprotective effects against oxidative stress in retinal ganglion cells Brain Research 1251 2009 269 275
32. U. Singh, and S. Devaraj Vitamin E: inflammation and atherosclerosis Vitamins and Hormones 76 2007 519 549
33. D. Steinberg Low density lipoprotein oxidation and its pathobiological significance The Journal of Biological Chemistry 272 1997 20963 20966
34. C. Tringali, and M. Piattelli Two chromone derivatives from the brown alga Zonaria Tournefortii Tetrahedron Letters 23 1982 1509 1512
35. A. Vik, T.V. Hansen, A.K. Holmeide, and L. Skattebøl Synthesis of juniperonic acid Tetrahedron Letters 51 2010 2852 2854
36. A. Vik, and T.V. Hansen Synthesis of a polyunsaturated amino ketone isolated from a Guangxi sponge of the genus Haliclona Tetrahedron Letters 53 2011 5837 5839
37. M. Vokurkova, S. Xu, and R.M. Touyz Reactive oxygen species, cell growth, cell cycle progression and vascular remodeling in hypertension Future Cardiology 3 2007 53 63
38. H. Zhang, X. Xiao, M.M. Conte, Z. Khalil, and R.J. Capon Spiralisones A-D: acylphloroglucinol hemiketals from an Australian marine brown alga, Zonaria spiralis Organic and Bimolecular Chemistry 10 2012 9671 9676