Anti-apoptotic activity of hydroxytyrosol and hydroxytyrosyl laurate

Food and Chemical Toxicology

Volumn 55, Issue , 2013, Pages 248-256

  Burattini, Sabrina ^a   Salucci, Sara ^a   Baldassarri, Valentina ^a   Accorsi, Augusto ^a   Piatti, Elena ^a   Madrona, Andres ^b   Espartero, Josè L ^b   Candiracci, Manila ^a,b   Zappia, Giovanni ^a   Falcieri, Elisabetta ^a,c  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF SEVILLE   (Spain)

^c CNR   (Italy)

Author keywords

Apoptosis; H2O2; HyT; Laur HyT

Indexed keywords

HYDROGEN PEROXIDE; HYDROXYTYROSOL; HYDROXYTYROSYL LAURATE; POLYPHENOL; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CELL PROTECTION; DRUG EFFECT; HUMAN; HUMAN CELL; MONOCYTE; MOUSE; MYOBLAST; NONHUMAN;

ANIMALS; APOPTOSIS; CELL LINE; HUMANS; LAURIC ACIDS; MICE; PHENYLETHYL ALCOHOL; REACTIVE OXYGEN SPECIES;

EID: 84873678239     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2012.12.049     Document Type: Article

References (50)

1. Bendini A., Cerretani L., Carrasco-Pancorbo A., Gómez-Caravaca A.M., Segura-Carretero A., Fernández-Gutiérrez A., Lercker G. Phenolic molecules in virgin olive oils: a survey of their sensory properties, health effects, antioxidant activity and analytical methods. An overview of the last decade. Molecules 2007, 12(8):1679-1719.
2. Bitler C.M., Viale T.M., Damaj B., Crea R. Hydrolyzed olive vegetation water in mice has anti-inflammatory activity. J. Nutr. 2005, 135(6):1475-1479.
3. Briante R., La Cara F., Febbraio F., Patumi M., Nucci R. Bioactive derivatives from oleuropein by a biotransformation on Olea europaea leaf extracts. J. Biotechnol. 2002, 93:109-119.
4. Burattini S., Ferri P., Battistelli M., D'Emilio A., Biagiotti L., Sestili P., Rocchi M.B., Falcieri E. Apoptotic DNA fragmentation can be revealed in situ: an ultrastructural approach. Microsc. Res. Tech. 2009, 72(12):913-923.
5. Burattini S., Battistelli M., Falcieri E. Morpho-functional features of in-vitro cell death induced by physical agents. Curr. Pharm. Des. 2010, 16(12):1376-1386.
6. Burattini S., Salucci S., Baldassarri V., Accorsi A., Candiracci M., Piersanti G., Espartero Sanchez J.L., Zappia G., Falcieri E. Hydroxytyrosol derivatives vs. apoptosis: a protective action?. In: 10th Multinational Congress on Microscopy, Urbino 4-9 September, 2011. p. 165.
7. Burke W.J. 3,4-dihydroxyphenylacetaldehyde: a potential target for neuroprotective therapy inParkinson's disease. Curr. Drug Targets CNS Neurol. Disord. 2003, 2(2):143-148.
8. Covas M.I., Ruiz-Gutiérrez V., De la Torre R., Kafatos A. Minor components of olive oil: evidence to date of health benefits in humans. Nutr. ReV. 2006, 64:S20.
9. Curci R., Battistelli M., Burattini S., D'Emilio A., Ferri P., Lattanzi D., Ciuffoli S., Ambrogini P., Cuppini R., Falcieri E. Surface and inner cell behaviour along skeletal muscle cell in vitro differentiation. Micron 2008, 39(7):843-851.
10. Daccache A., Lion C., Sibille N., Gerard M., Slomianny C., Lippens G. Oleuropein and derivatives from olives as Tau aggregation inhibitors. Neurochem. Int. 2011, 58(6):700-707.
11. D'Angelo S., Manna C., Migliardi V., Mazzoni O., Morrica P., Capasso G., Pontoni G., Galletti P., Zappia V. Pharmacokinetics and metabolism of hydroxytyrosol, a natural antioxidant from olive oil. Drug Metab. Dispos. 2001, 29(11):1492-1498.
12. Dell'Agli M., Maschi O., Galli G.V., Fagnani R., Dal Cero E., Caruso D. Inhibition of platelet aggregation by olive oil phenols via cAMP-phosphodiesterase. Br. J. Nutr. 2008, 99(5):945-951.
13. De Leonardis A., Aretini A., Alfano G., Macciola V., Ranalli G. Isolation of a hydroxytyrosol-rich extract from olive leaves (Olea europaea L) and evaluation of its antioxidant properties and bioactivity. Eur. Food Res Technol. 2008, 226(4):653-659.
14. D'Emilio A., Biagiotti L., Burattini S., Battistelli M., Canonico B., Evangelisti C., Ferri P., Papa S., Martelli A.M., Falcieri E. Morphological and biochemical patterns in skeletal muscle apoptosis. Histol. Histopathol. 2010, 25(1):21-32.
15. Fabiani R., Rosignoli P., De Bartolomeo A., Fuccelli R., Servili M., Montedoro G.F., Morozzi G. Oxidative DNA damage is prevented by extracts of olive oil, hydroxytyrosol, and other olive phenolic compounds in human blood mononuclear cells and HL60 cells. J. Nutr. 2008, 138(8):1411-1416.
16. Feng Z., Bai L., Yan J., Li Y., Shen W., Wang Y., Wertz K., Weber P., Zhang Y., Chen Y., Liu J. Mitochondrialdynamicremodelingin strenuous exercise-induced muscle andmitochondrialdysfunction: regulatory effects of hydroxytyrosol. Free Radic. Biol. Med. 2011, 50(10):1437-1446.
17. Fitó M., Covas M.I., Lamuela-Raventós R.M., Vila J., Torrents L., de la Torre C., Marrugat J. Protective effect of olive oil and its phenolic compounds against low density lipoprotein oxidation. Lipids 2000, 35(6):633-638.
18. González-Correa J.A., Navas M.D., Lopez-Villodres J.A., Trujillo M., Espartero J.L., De La Cruz J.P. Neuroprotective effect of hydroxytyrosol and hydroxytyrosol acetate in rat brain slices subjected to hypoxia-reoxygenation. Neurosci. Lett. 2008, 446(2-3):143-146.
19. Goya L., Mateos R., Bravo L. Effect of the olive oil phenol hydroxytyrosol on human hepatoma HepG2 cells. Protection against oxidative stress induced by tert-butylhydroperoxide. Eur. J. Nutr. 2007, 46(2):70-78.
20. Granados-Principal S., Quiles J.L., Ramirez-Tortosa C.L., Sanchez-Rovira P., Ramirez-Tortosa M.C. Hydroxytyrosol: from laboratory investigations to future clinical trials. Nutr. Rev. 2010, 68(4):191-206.
21. Hashimoto T., Ibi M., Matsuno K., Nakashima S., Tanigawa T., Yoshikawa T., Yabe-Nishimura C. An endogenous metabolite of dopamine, 3,4-dihydroxyphenylethanol, acts as a unique cytoprotective agent against oxidative stress-induced injury. Free Radic. Biol. Med. 2004, 36(5):555-564.
22. Liu Z., Sun L., Zhu L., Jia X., Li X., Jia H., Wang Y., Weber P., Long J., Liu J. Hydroxytyrosolprotectsretinalpigmentepithelialcellsfromacrolein-inducedoxidativestressandmitochondrialdysfunction. J. Neurochem. 2007, 103(6):2690-2700.
23. Loro E., Rinaldi F., Malena A., Masiero E., Novelli G., Angelini C., Romeo V., Sandri M., Botta A., Vergani L. Normal myogenesis and increased apoptosis in myotonic dystrophy type-1 muscle cells. Cell Death Differ. 2010, 17(8):1315-1324.
24. Luchetti F., Canonico B., Curci R., Battistelli M., Mannello F., Papa S., Tarzia G., Falcieri E. Melatonin prevents apoptosis induced by UV-B treatment in U937 cell line. J. Pineal Res. 2006, 40:158-167.
25. Madrona, D.A., 2012. Tesis Doctoral. éteres alquílicos derivados de polifenoles del olivo. Síntesis y evaluación de su actividad antioxidante. Universidad de Sevilla, Facultad de Farmacia, Marzo de.
26. Manna C., Galletti P., Cucciolla V., Montedoro G., Zappia V. Olive oil hydroxytyrosol protects human erythrocytes against oxidative damages. J. Nutr. Biochem. 1999, 10(3):159-165.
27. Mateos R., Trujillo M., Pereira-Caro G., Madrona A., Cert A., Espartero J.L. New lipophilic tyrosyl esters. Comparative antioxidant evaluation with hydroxytyrosyl esters. J. Agric. Food Chem. 2008, 56(22):10960-10966.
28. Medina I., Lois S., Alcántara D., Lucas R., Morales J.C. Effect of lipophilization of hydroxytyrosol on its antioxidant activity in fish oils and fish oil-in-water emulsions. J. Agric. Food Chem. 2009, 57(20):9773-9779.
29. Omar S.H. Oleuropein in olive and its pharmacological effects. Sci. Pharm. 2010, 78(2):133-154.
30. Paiva-Martins F., Fernandes J., Rocha S., Nascimento H., Vitorino R., Amado F., Borges F., Belo L., Santos-Silva A. Effects of olive oil polyphenols on erythrocyte oxidative damage. Mol. Nutr. Food Res. 2009, 53(5):609-616.
31. Paiva-Martins F., Fernandes J., Santos V., Silva L., Borges F., Rocha S., Belo L., Santos-Silva A. Powerful protective role of 3,4-dihydroxyphenylethanol-elenolic acid dialdehyde against erythrocyte oxidative-induced hemolysis. J. Agric. Food Chem. 2010, 58(1):135-140.
32. Pereira-Caro G., Madrona A., Bravo L., Luis Espartero J., Alcudia F., Cert A., Mateos R. Antioxidant activityevaluation of alkyl hydroxytyrosyl ethers, a new class ofhydroxytyrosolderivatives. Food Chem. 2009, 115(1):86-91.
33. Pereira-Caro G., Sarriá B., Madrona A., Espartero J.L., Goya L., Bravo L., Mateos R. Alkyl hydroxytyrosyl ethers show protective effects against oxidative stress in HepG2 cells. J. Agric. Food Chem. 2011, 59(11):5964-5976.
34. Piersanti G., Retini M., Espartero J.L., Madrona A., Zappia G. An efficient, economical synthesis of hydroxytyrosol and its protected forms via Baeyer-Villiger oxidation. Tetrahedron Lett. 2011, 52(38):4938-4940. (and reference therein).
35. Pignatelli P., Di Santo S., Buchetti B., Sanguigni V., Brunelli A., Violi F. Polyphenols enhance platelet nitric oxide by inhibiting protein kinase C-dependent NADPH oxidase activation: effect on platelet recruitment. FASEB J. 2006, 20(8):1082-1089.
36. Raederstorff D. Antioxidant activity of olive polyphenols in humans: a review. Int. J. Vitam. Nutr. Res. 2009, 79(3):152-165.
37. Rafehi H., Smith A.J., Balcerczyk A., Ziemann M., Ooi J., Loveridge S.J., Baker E.K., El-Osta A., Karagiannis T.C. Investigation into the biological properties of the olive polyphenol, hydroxytyrosol: mechanistic insights by genome-wide mRNA-Seq analysis. Genes Nutr. 2012, 7(2):343-355.
38. Rietjens S.J., Bast A., Haenen G.R. New insights into controversies on the antioxidant potential of the olive oil antioxidant hydroxytyrosol. J. Agric. Food Chem. 2007, 55(18):7609-7614.
39. Rodríguez-Ramiro I., Martín M.á., Ramos S., Bravo L., Goya L. Olive oil hydroxytyrosol reduces toxicity evoked by acrylamide in human Caco-2 cells by preventing oxidative stress. Toxicology 2011, 288(1-3):43-48.
40. Salucci S., Battistelli M., Burattini S., Squillace C., Canonico B., Gobbi P., Papa S., Falcieri E. C2C12 myoblast sensitivity to different apoptotic chemical triggers. Micron 2010, 41(8):966-973.
41. Salucci S., Baldassarri V., Burattini S., Accorsi A., Piatti E., Zappia G., Piersanti G., Espartero Sanchez J.L., Falcieri E., 2011. Protective action of hydroxytyrosol derivates vs. apoptosis: apreliminary study. Congresso della Società Italiana di Istochimica. San Benedetto del Tronto 7-9 Giugno, vol. 55(suppl.1). p. 23.
42. Sandri M. Autophagy in skeletal muscle. FEBS 2010, 584(7):1411-1416.
43. Tasset I., Pontes A.J., Hinojosa A.J., de la Torre R., Túnez I. Olive oil reduces oxidative damage in a 3-nitropropionic acid-induced Huntington's disease-like rat model. Nutr. Neurosci. 2011, 14(3):106-111.
44. Teixeira V.de O., Filippin L.I., Xavier R.M. Mechanisms of muscle wasting in sarcopenia. Rev. Bras. Reumatol. 2012, 52(2):252-259.
45. Tofani D., Balducc i V., Gasperi T., Incerpi S., Gambacorta A. Fatty acid hydroxytyrosyl esters: structure/antioxidant activity relationship by ABTS and in cell-culture DCF assays. J. Agric. Food Chem. 2010, 58(9):5292-5299.
46. Tripoli E., Giammanco M., Tabacchi G., Di Majo D., Giammanco S., La Guardia M. The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health. Nutr. Res. ReV. 2005, 18:98-112.
47. Trujllo, M., Mateos, R., Collantes de Teran, L., Espartero, J.L., Cert, R., Jover, M., Alcudia F., Bautista, J., Cert, A., Parrado, J., 2006. Lipophilic Hydroxytyrosyl Esters. Antioxidant Activity in Lipid Matrices and Biological Systems J. Agric. Food Chem. 54, 3779-3785; see also: Alcudia, F., Cert, A., Espartero, J.L., Mateos, R., Trujillo, M. 2004. Method of preparing hydroxytyrosol esters, esters thus obtained and use of same. PCT WO 2004/005237.
48. Visioli F., Bernardini E. Extra virgin olive oil's polyphenols: biological activities. Curr. Pharm. Des. 2011, 17(8):786-804.
49. Waterman E., Lockwood B. Active components and clinical applications ofolive oil. Altern. Med. Rev. 2007, 12(4):331-342.
50. Zhang S., Li X., Li L., Yan X. Autophagy up-regulation by early weaning in the liver, spleen andskeletal muscle of piglets. Br. J. Nutr. 2011, 27:1-5.