Protective effect and relation structure-activity of nonivamide and iododerivatives in several models of lipid oxidation

Chemico-Biological Interactions

Volumn 180, Issue 2, 2009, Pages 183-192

  Rosa, Antonella ^a   Appendino, Giovanni ^b   Melis, M Paola ^a   Deiana, Monica ^a   Atzeri, Angela ^a   Alessandra, Incani ^a   Minassi, Alberto ^b   Dessì, M Assunta ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

^b UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

Antioxidants; Cholesterol; Iodononivamides; Linoleic acid; Low density lipoprotein; Nonivamide

Indexed keywords

2 IODONONIVAMIDE; 5 IODONONIVAMIDE; 6 IODONONIVAMIDE; ALPHA TOCOPHEROL; ANTIOXIDANT; BUTYLCRESOL; CHOLESTEROL; IODODERIVATIVE; LINOLEIC ACID; LOW DENSITY LIPOPROTEIN; LUTEOLIN; NONIVAMIDE; PHENOL DERIVATIVE; POLYUNSATURATED FATTY ACID; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; LIPID OXIDATION; LIPID PEROXIDATION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIOXIDANTS; CAPSAICIN; CELL LINE; CHOLESTEROL, LDL; CYTOTOXINS; IODINE; LIPID PEROXIDATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

EID: 67349243632     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2009.01.002     Document Type: Article

References (37)

1. Aruoma O.I. Free radicals, oxidants and antioxidants: trend towards the year 2000 and beyond. In: Aruoma O.I., and Halliwell B. (Eds). Molecular Biology of Free Radicals in Human Diseases (1998), OICA International, London 1-28
2. Salonen J.T. Markers of oxidative damage and antioxidant protection: assessment of LDL oxidation. Free Radic. Res. 33 (2000) S41-46
3. Aldred S. Oxidative and nitrative changes seen in lipoproteins following exercise. Atherosclerosis 192 (2007) 1-8
4. Prigol M., Wilhelm E.A., Schneider C.S., and Nogueira C.W. Protective effect of unsymmetrical dichalcogenide, a novel antioxidant agent, in vitro and in vivo model of brain oxidative damage. Chem. Biol. Interact. 176 (2008) 129-136
5. Duthie G., and Crosier A. Plant-derived phenolic antioxidants. Curr. Opin. Clin. Nutr. Metab. Care 3 (2000) 447-451
6. Lapointe A., Couillard C., and Lemieux S. Effect of dietary factors on oxidation of low-density lipoprotein particles. J. Nutr. Biochem. 17 (2006) 645-658
7. Rice-Evans C.A., Miller N.J., and Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20 (1996) 933-956
8. Fang J.Y., Leu Y.L., Wang Y.Y., and Tsai Y.H. In vitro topical application and in vivo pharmacodynamic evaluation of nonivamide hydrogels using Wistar rat as an animal model. Eur. J. Pharm. Sci. 15 (2002) 417-423
9. Sancho R., Lucena C., Macho A., Calzado M.A., Blanco Molina M., Minassi A., Appendino G., and Munoz E. Immunosuppressive activity of capsaicinoids: capsiate derived from sweet peppers inhibits NF-kB activation and is a potent anti-inflammatory compound in vivo. Eur. J. Immunol. 32 (2002) 1753-1763
10. Appendino G., Daddario N., Minassi A., Moriello A.S., De Petrocellis L., and Di Marzo V. The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination. J. Med. Chem. 48 (2005) 4663-4669
11. Lee Y.S., Kang Y.S., Lee J.S., Nicolova S., and Kim J.A. Involvment of NADPH oxidase-mediated generation of reactive oxygen species in the apoptotic cell death by capsaicin in HepG2 human hepatoma cells. Free Radic. Res. 4 (2004) 405-412
12. Kogure K., Goto S., Nishimura M., Yasumoto M., Abe K., Ohiwa C., Sassa H., Kusumi T., and Terada H. Mechanism of potent antiperoxidative effect of capsaicin. Biochim. Biophys. Acta 1573 (2002) 84-92
13. Henderson D.E., and Slickman A.M. Quantitative HPLC determination of the antioxidant activity of capsaicin on the formation of lipid hydroperoxides of linoleic acid: a comparative study against BHT and melatonin. J. Agric. Food Chem. 47 (1999) 2563-2570
14. Kempaiah R.K., Manjunatha H., and Srinivasan K. Protective effect of dietary capsaicin on induced oxidation of low-density lipoprotein in rats. Mol. Cell. Biochem. 275 (2004) 7-13
15. Dairam A., Fogel R., Daya S., and Limson J.L. Antioxidant and iron-binding properties of curcumin, capsaicin, and S-allylcysteine reduce oxidative stress in rat brain homogenate. J. Agric. Food Chem. 56 (2008) 3350-3356
16. Constant H.L., and Cordell G.A. Nonivamide, a constituent of Capsicum oleoresin. Mol. Cell. Biochem. 59 (1996) 425-426
17. Appendino G., Harrison S., De Petrocellis L., Daddario N., Bianchi F., Schiano Moriello A., Trevisani M., Benvenuti F., Geppetti P., and Di Marzo V. Halogenation of a capsaicin analogue leads to novel vanilloid TRPV1 receptor antagonists. Br. J. Pharmacol. 139 (2003) 1417-1424
18. Banni S., Contini M.S., Angioni E., Deiana M., Dessì M.A., Melis M.P., Carta G., and Corongiu F.P. A novel approach to study linoleic acid autoxidation: importance of simultaneous detection of the substrate and its derivative oxidation products. Free Radic. Res. 25 (1996) 43-53
19. Dessì M.A., Deiana M., Rosa A., Piredda M., Cottiglia F., Bonsignore L., Deidda D., Pompei R., and Corongiu F.P. Antioxidant activity of extracts from plants growing in Sardinia. Phytother. Res. 15 (2001) 511-518
20. Rosa A., Deiana M., Atzeri A., Corona G., Incani A., Melis M.P., Appendino G., and Dessì M.A. Evaluation of the antioxidant and cytotoxic activity of arzanol, a prenylated alpha-pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp. microphyllum. Chem. Biol. Interact. 165 (2007) 117-126
21. Kim S.K., and Nawar W.W. Parameters influencing cholesterol oxidation. Lipids 28 (1993) 917-922
22. Schiller C.J., Klainz A., Mynett K., and Gescher A. Assessment of viability of hepatocytes in suspension using the MTT assay. Toxicol. in Vitro 6 (1992) 575-578
23. Bradford M. Rapid and sensitive method for quantification of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
24. Rosa A., Melis M.P., Deiana M., Atzeri A., Appendino G., Corona G., Incani A., Loru D., and Dessì M.A. Protective effect of the oligomeric acylphloroglucinols from Myrtus communis on cholesterol and human low density lipoprotein oxidation. Chem. Phys. Lipids 155 (2008) 16-23
25. Folch J., Lees M., and Sloane-Stanley G.H. A simple method for the isolation and purification of total lipid from animals tissues. J. Biol. Chem. 226 (1957) 497-509
26. Rosa A., Deiana M., Casu V., Appendino G., Ballero M., and Dessì M.A. Antioxidant activity of capsinoids. J. Agric. Food Chem. 50 (2003) 7396-7401
27. Rosa A., Deiana M., Corona G., Atzeri A., Incani A., Appendino G., and Dessì M.A. Protective effect of capsinoid on lipid peroxidation in rat tissues induced by Fe-NTA. Free Radic. Res. 39 (2005) 1155-1162
28. Heijnen C.G.M., Haenen G.R.M.M., Minou Oostveen R., Stalpers E.M., and Bast A. Protection of flavonoids against lipid peroxidation: the structure activity relationship revisited. Free Radic. Res. 36 (2002) 575-581
29. Frankel E.N. Chemistry of antioxidation. In: Frankel E.N. (Ed). Antioxidant in Food and Biology (2007), The Oily Press, Bridgwater, England 21-42
30. Gerry A.B., Satchell L., and Leake D.S. A novel method for production of lipid hydroperoxide-or oxysterol-rich low-density lipoprotein. Atherosclerosis 197 (2008) 579-587
31. Ak T., and Gulcin I. Antioxidant and radical scavenging properties of curcumin. Chem. Biol. Interact. 174 (2008) 27-37
32. Chen W.F., Deng S.L., Zhou B., Yang L., and Liu Z.L. Curcumin its analogues as potent inhibitors of low density lipoprotein oxidation: H-atom abstraction from the phenolic groups and possible involvement of the 4-hydroxy-3-methoxyphenyl groups. Free Radic. Biol. Med. 40 (2006) 526-535
33. Rocha-Guzman N.E., Gallegos-Infante J.A., Gonzalez-Laredo R.F., Ramos-Gomez M., Rodriguez-Munoz M.E., Reynoso-Camacho R., Rocha-Uribe A., and Roque-Rosales M.R. Antioxidant effect of oregano (Lippia berlandieri v. Shauer) essential oil and mother liquors. Food Chem. 102 (2007) 330-335
34. Kaneko T., Kaji K., and Matsuo M. Protection of linoleic acid hydroperoxide-induced cytotoxicity by phenolic antioxidants. Free Radic. Biol. Med. 16 (1994) 405-409
35. Thanh H.T., Beney L., Simonin H., Nguyen T.X.S., Gervais P., Belin J.M., and Husson F. Toxicity of fatty acid hydroperoxides towards Yarrowia lipolytica: implication of their membrane fluidizing action. Biochim. Biophys. Acta 1768 (2007) 2256-2262
36. Guardiola F., Codony R., Addis P.B., Rafecas M., and Boatella J. Biological effects of oxysterols: current status. Food Chem. Toxicol. 34 (1996) 193-211
37. Neudorffer A., Dersvergne J.P., Bonnefont-Rousselot D., Legrand A., Fleury M.B., and Largeron M. Protective effect of 4-hydroxycinnamic ethyl ester derivatives and related dehydrodimers against oxidation of LDL: radical scavengers or metal chelators?. J. Agric. Food Chem. 54 (2006) 1898-1905