Hydroxytyrosol and oleuropein from olive leaves: Potent anti-inflammatory and analgesic activities

Journal of Food, Agriculture and Environment

Volumn 9, Issue 3-4, 2011, Pages 128-133

  Haloui, Ehsen ^a   Marzouk, Belsem ^a   Marzouk, Zohra ^a   Bouraoui, Abderrahman ^a   Fenina, Nadia ^a  

^a UNIVERSITY OF MONASTIR   (Tunisia)

Author keywords

Analgesic activity; Anti inflammatory activity; Hydroxytyrosol; Olea europaea L. cv. Chemlali; Oleuropein; Paw oedema; Writhing test

Indexed keywords

ACETYLSALICYLIC ACID; CARRAGEENAN; HYDROXYTYROSOL; OLEUROPEIN; OLIVE EXTRACT; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFECT; FEMALE; INFLAMMATION; MALE; MOUSE; NOCICEPTION; NONHUMAN; OLIVE; OLIVE TREE; PAW EDEMA; PLANT LEAF; RAT; TOXICITY TESTING; WRITHING TEST;

OLEA EUROPAEA;

EID: 80655134664     PISSN: 14590255     EISSN: 14590263     Source Type: Journal    
DOI: None     Document Type: Article

References (68)

1. Gariboldi, P., Jommi, G. and Verotta, L. 1986. Secoiridoids from Olea europaea. Phytochemistry 25(4):865-869.
2. Heimler, D., Pieroni, A., Tattini, M. and Cimato, A. 1992. Determination of flavonoid glycosides and biflavonoids in Olea europaea L. leaves. Chromatographia 33:369-373.
3. Tutour, B. and Guedon, D. 1992. Antioxidative activities of Olea europaea leaves and related phenolic compounds. Phytochem. 31:1173-1178.
4. Romani, A., Baldi, A., Tattini, M. and Vincieri, F. F. 1994. Extraction, purification procedures and HPLC-RI analysis of carbohydrates in olive (Olea europaea L.) plants. Chromatographia 39:35-39.
5. Pieroni, A., Heimler, D., Pieters, L., Van Poel, B. and Vlietnick, A. J. 1996. In vitro anti-complementary activity of flavonoids from olive (Olea europaea L.) leaves. Pharmazie 51:765-768.
6. Savournin, C., Baghdikian, B., Elias, R., Dargouth-Kesraoui, F., Boukef, K. and Balansard, G. 2001. Rapid high-performance liquid chromatography analysis for the quantitative determination of oleuropein in Olea europaea leaves. J. Agric. Food Chem. 49:618-621.
7. Jemai, H., Bouaziz, M., Fki, I., El-Feki, A. and Sayadi, S. 2008. Hypolipidimic and antioxidant activities of oleuropein and its hydrolysis derivative-rich extracts from Chemlali olive leaves. Chem. Biol. Interact. 176:88-98.
8. Jemai, H., Fki, I., Bouaziz, M., Bouallagui, Z., El-Feki, A., Isoda, H. and Sayadi, S. 2008. Lipid-lowering and antioxidant effects of hydroxytyrosol and its triacetylated derivative recovered from olive tree leaves in cholesterol-fed rats. J. Agric. Food Chem. 56:2630-2636.
9. Lee, O. H., Lee, B. Y., Lee, J., Lee, H. B., Son, J. Y., Park, C. S., Shetty, K. and Kim, Y. C. 2009. Assessment of phenolics-enriched extract and fractions of olive leaves and their antioxidant activities. Bioresour. Technol. 100:6107-6113.
10. Briante, R., Patumi, M., Terenziani, S., Bismuto, E., Febbraio, F. and Nucci, R. 2002. Olea europaea: Leaf extract and derivatives, antioxidant properties. J. Agric. Food Chem. 50:4934-4940.
11. Brenes, M., García, A., García, P. and Garrido, A. 2001. Acid hydrolysis of secoiridoid aglycons during storage of virgin olive oil. J. Agric. Food Chem. 49:5609-5614.
12. González, M., Zarzuelo, A., Gámez, M. J., Utrilla, M. P., Jiménez, J. and Osuna, I. 1992. Hypoglycemic activity of olive leaf. Planta Méd. 58:513-515.
13. Petkov, V. and Manolov, P. 1978. Pharmacological studies on substances of plant origin with coronary dilatating and antiarrhythmatic action. Comparative Medicine East and West 6:123-130.
14. Zarzuelo, A., Duarte, J., Jiménez, M. and Utrilla, P. 1991. Vasodilator effect of olive leaf. Planta Méd. 57:417-419.
15. Bisignano, G., Tomaino, A., Lo Cascio, R., Crisafi, G., Uccella, N. and Saija, A. 1999. On the in vitro antimicrobial activity of oleuropein and hydroxytyrosol. J. Pharm. Pharmacol. 51:971-974.
16. Tranter, H. S., Tassou, C. C. and Nychas, G. J. E. 1993. The effect of the olive phenolic compound, oleuropein, on growth and enterotoxin B production by Staphylococcus aureus. J. Appl. Bact. 74:253-259.
17. Furneri, P. M., Marino, A., Saija, A., Uccella, N. and Bisignano, G. 2002. In vitro antimycoplasmal activity of oleuropein. Int. J. Antimicrob. Agents 20:293-296.
18. Ribeiro, R. A., Fiuza de Melo, M. M., De Barros, F., Gomes, C. and Trolin, G. 1986. Acute antihypertensive effect in conscious rats produced by some medicinal plants used in the state of Sao Paulo. J. Ethnopharmacol 15:261-269.
19. Khayyal, M. T., El-Ghazaly, M. A., Abdallah, D. M., Nassar, N. N., Okpanyi, S. N. and Kreuter, M. H. 2002. Blood pressure lowering effect of an olive leaf extract (Olea europaea) in L-NAME induced hypertension in rats. Arznem Forsch 52:797-802.
20. Díaz, A. M., Abad, M. J., Fernández, L., Recuero, C., Villaescusa, L., Silvan, A. M. and Bermejo, P. 2000. In vitro anti-inflammatory activity of iridoids and triterpenoid compounds isolated from Phillyrea latifolia L. Biol. Pharm. Bull. 23:1307-1313.
21. Visioli, F., Bellasta, S. and Galli, C. 1998. Oleuropein, the bitter principle of olives, enhances nitric oxide production by mouse macrophages. Life Sci. 62:541-546.
22. Visioli, F. and Galli, C. 2001. Antiatherogenic components of olive oil. Curr. Ather. Rep. 3:64-67.
23. Carluccio, M. A., Siculella, L., Ancora, M. A., Massaro, M., Scoditti, E., Storelli, C., Visioli, F., Distante, A. and De Caterina, R. 2003. Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: Antiatherogenic properties of Mediterranean diet phytochemicals. Arterioscler. Thromb. Vas. 23:622-629.
24. Visioli, F., Bellomo, G., Montedoro, G. F. and Galli, C. 1995. Low-density lipoprotein oxidation is inhibited in vitro by olive oil constituents. Atherosclerosis 117:25-32.
25. Visioli, F., Poli, A. and Galli, C. 2002. Antioxidant and other biological activities of phenols from olives and olive oil. Med. Res. Rev. 22:65-75.
26. Andrikopoulos, N. K., Kaliora, A. C., Assimopoulou, A. N and Papageorgiou, V. P. 2002. Inhibitory activity of minor polyphenolic and non-polyphenolic constituents of olive oil against in vitro low-density lipoprotein oxidation. J. Med. Food 5:1-7.
27. De la Puerta, R., Ruiz Gutiérrez, V. and Hoult, J. R. 1999. Inhibition of leukocyte 5-lipoxygenase by phenolics from virgin olive oil. Biochem. Pharmacol. 57:445-449.
28. Gordon, M. H., Paiva-Martins, F. and Almeida, M. 2001. Antioxidant activity of hydroxytyrosol acetate compared with that of other olive oil polyphenols. J. Agric. Food Chem. 49:2480-2485.
29. Visioli, F., Bellomo, G. and Galli, C. 1998. Free radical-scavenging properties of olive oil polyphenols. Biochem. Biophys. Res. Commun. 247:60-64.
30. Visioli, F., Caruso, D., Plasmati, E., Patelli, R., Mulinacci, N., Romani, A., Galli, G. and Galli, C. 2001. Hydroxytyrosol, as a component of olive mill waste water, is dose-dependently absorbed and increases the antioxidant capacity of rat plasma. Free Radical Res. 34:301-305.
31. Saija, A., Trombetta, D., Tomaino, A., Lo Cascio, R., Trinci, P., Uccella, N., Bonina, F. and Castelli, F. 1998. In vitro evaluation of the antioxidant activity and biomembrane interaction of the plant phenols oleuropein and hydroxytyrosol. Int. J. Pharm. 166:123-133.
32. Stupans, I., Kirlich, A., Tuck, K. L. and Hayball, P. J. 2002. Comparison of radical scavenging effect, inhibition of microsomal oxygen free radical generation and serum lipoprotein oxidation of several natural antioxidants. J. Agric. Food Chem. 50:2464-2469.
33. Hamden, K., Allouche, N., Damak, M. and El-Feki, A. 2009. Hypoglycemic and antioxidant effects of phenolic extracts and purified hydroxytyrosol from olive mill waste in vitro and in rats. Chem.-Biol. Interact. 180(3):421-432.
34. Leger, C. L., Carbonneau, M. A. and Michel, F. 2005. A thromboxane effect of a hydroxytyrosol-rich olive oil wastewater extract in patients with uncomplicated type I diabetes. Eur. J. Clin. Nutr. 59:727-730.
35. Covas, M. I., De la Torre, K. and Farre-Albaladejo, M. 2006. Postprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humans. Free Radical Bio. Med. 40:608-616.
36. Deiana, M., Incani, A., Rosa, A., Corona, G., Atzeri, A., Loru, D., Melis, M. P. and Dessì, M. A. 2008. Protective effect of hydroxytyrosol and its metabolite homovanillic alcohol on H2O2-induced lipid peroxidation in renal tubular epithelial cells. Food Chem. Toxicol. 46:2984-2990.
37. Beauchamp, G. K., Keast, R. S., Morel, D., Lin, J., Pika, J., Han, Q., Lee, C. H., Smith, A. B and Breslin, P. A. 2005. Phytochemistry: Ibuprofen-like activity in extra virgin olive oil. Nature 437:45-46.
38. Pacheco, Y. M., Bermúdez, B., López, S., Abia, R., Villar, J. and Muriana, F. J. 2007. Minor compounds of olive oil have postprandial anti-inflammatory effects. Br. J. Nutr. 29:1-4.
39. Aziz, N. H., Farag, S. E., Mousa, L. A and Abo-Zaid, M. A. 1998. Comparative antibacterial and antifungal effects of some phenolic compounds. Microbios 93:43-54.
40. Furneri, P. M., Piperno, A., Sajia, A. and Bisignano, G. 2004. Antimycoplasmal activity of hydroxytyrosol. Antimicrob. Agents Chemother. 48:4892-4894.
41. Yamada, K., Ogawa, H., Hara, A., Yoshida, Y., Yonezawa, Y., Karibe, K., Bui Nghia, V., Yoshimura, H., Yamamoto, Y., Yamada, M., Nakamura, K. and Imai, K. 2009. Mechanism of the antiviral effect of hydroxytyrosol on influenza virus appears to involve morphological change of the virus. Antivir. Res. 83:35-44.
42. Manna, C., Galletti, P., Cucciola, V., Montedoro, G. and Zappia, V. 1999. Olive oil hydroxytyrosol protects human erythrocytes against oxidative damages. J. Nutr. Biochem. 10:159-165.
43. Liu, Z., Sun, L., Zhu, L., Jia, X., Li, X. and Jia, H. 2007. Hydroxytyrosol protects retinal pigment epithelial cells from acrolein-induced oxidative stress and mitochondrial dysfunction. J. Neurochem. 103:2690-2700.
44. Zhu, L., Liu, Z., Feng, Z., Hao, J., Shen, W., Li, X., Sun, L., Sharman, E., Wang, Y., Wertz, K., Weber, P., Shi, X. and Liu, J. 2010. Hydroxytyrosol protects against oxidative damage by simultaneous activation of mitochondrial biogenesis and phase II detoxifying enzyme systems in retinal pigment epithelial cells. J. Nutr. Biochem. 21:1089-1098.
45. D'Angelo, S., Ingrosso, D., Migliardi, V., Sorrentino, A., Donnarumma, G., Baroni, A., Masella, L., Tufano, M. A., Zappia, M. and Galletti, P. 2005. Hydroxytyrosol, a natural antioxidant from olive oil, prevents protein damage induced by long-wave ultraviolet radiation in melanoma cells. Free Radical Biol. Med. 38:908-919.
46. Carluccio, M. A., Massaro, M., Ancora, M. A., Scoditti, E., Storelli, C. and Distante, A. 2006. Hydroxytyrosol, a phenolic antioxidant from olive and olive oil, reduces metalloproteinase (MMP)-9 expression and activity in human monocytoid cells: Possible contribution to plaque stability. Eur. Heart J. 27:455.
47. González-Santiago, M., Martín-Bautista, E., Carrero, J. J., Fonollá, J., Baró, L. and Bartolomé, M. V. 2006. One-month administration of hydroxytyrosol, a phenolic antioxidant present in olive oil, to hyperlipemic rabbits improves blood lipid profile, antioxidant status and reduces atherosclerosis development. Atherosclerosis 188:35-42.
48. Manna, C., Galletti, P., Cucciola, V., Moltedo, O., Leone, A. and Zappia, V. 1997. The protective effect of the olive oil polyphenol (3,4-dihydroxyphenyl) ethanol counteracts reactive oxygen metabolite-induced cytotoxicity in Caco-2 cells. J. Nutr. 127:286-292.
49. Fabiani, R., De Bartolomeo, A., Rosignoli, P., Servili, M., Montedoro, G. F and Morozzi, G. 2002. Cancer chemoprevention by hydroxytyrosol isolated from virgin olive oil through G1 cell cycle arrest and apoptosis. Eur. J. Cancer Prev. 11:351-358.
50. Pottier-Alapetite, G. 1981. Flore de Tunisie: Angiospermes-Dicotylédones: Gamopétales. Imprimerie officielle de la République Tunisienne.
51. Jemai, H., El-Feki, A. and Sayadi, S. 2009. Antidiabetic and antioxidant effects of hydroxytyrosol and oleuropein from olive leaves in alloxan-diabetic rats. J. Agric. Food Chem. 57(19):8798-8804.
52. Miller, L. C. and Tainter, M. L. 1944. Estimation of the ED50 and its error by means of logprobit graphic paper. Proceeding of the Society for Experimental Biology and Medicine 57:261-264.
53. Koster, R., Anderson, M. and De Beer, E. J. 1959. Acetic acid for analgesic screening. Fed. Proc. 18:418-420.
54. Winter, C. A., Risley, E. A., Nuss, G. W. 1962. Carrageenan induced edema hind paw of the rat as an essay for anti-inflammatory drugs. Proceedings of the Society for Experimental Biology and Medicine 3:544-547.
55. Gong, D., Geng, C., Jiang, L., Cao, J., Yoshimura, H. and Zhong, L. 2009. Effects of hydroxytyrosol-20 on carrageenan induced acute inflammation and hyperalgesia in rats. Phytother. Res. 23:646-650.
56. Esmaeili-Mahani, S., Rezaeezadeh-Roukerd, M., Esmaeilpour, K., Abbasnejad, M., Rasoulian, B., Sheibani, V., Kaeidi, A. and Hajializadeh, Z. 2010. Olive (Olea europaea L.) leaf extract elicits antinoceptive activity, potentiates morphine analgesia and suppresses morphine hyperalgesia in rats. J. Ethnopharmacol 132:200-205.
57. Collier, H. O., Dinneen, L. C., Johnson, C. A. and Schneider, C. 1968. The abdominal construction response and its suppression by analgesic drugs in the mouse. Brit. J. Pharmacol. 32:295-310.
58. Bentley, G. A., Newtown, S. H. and Starr, J. 1983. Studies on the anti-nociceptive action of α-agonist drug and their interaction with opioid mechanisms. Brit. J. Pharmacol. 73:125-134.
59. Spereni, E., Cervellati, R., Innocenti, G., Costa, S., Guerra, M. C., Dall'Acqua, S. and Govoni, P. 2005. Anti-inflammatory, anti-nociceptive and antioxidant activities of Balanites aegyptica (L.) Delile. J. Ethnopharmacol 98:117-125.
60. Dhara, A. K., Suba, V., Sen, T., Pal, S. and Nag Chaudurhi, A. K. 2000. Preliminary studies on the anti-inflammatory and analgesic activity of the methanolic fraction the of root extract of 'Tagria' involucrate. J. Ethno. 72:265-268.
61. Levini, J. D., Lau, W., Kwait, G. and Goetzl, E. L. 1984. Leukotriene B4 produces hyperalgesia that is dependent on the polymorphonuclear leucocytes. Science 225:743-745.
62. Deraedt, R., Jougney, S., Benzoni, J. and Peterfalvi, M. 1980. Release of prostaglandins E and F in algogenic reaction and its inhibition. Eur. J. Pharmacol. 61:17-24.
63. García, M. D., Fernández, M. A., Álvarez, A. and Saenz, M. T. 2004. Anti-nociceptive and anti-inflammatory effect of the aqueous extract from leaves of Pimenta racemosa var. ozua (Mirtaceae). J. Ethnopharmacol 91:69-73.
64. Olajide, O. A., Makinde, M. J. and Awe, S. O. 1999. Effects of the aqueous extract of Bridelia ferruginea stem bark on carrageenan-induced oedema and granuloma tissue formation in rats and mice. J. Ethnopharmacol 66:113-117.
65. Moreira, A. S., Spitzer, V., Schapoval, E. E. and Schenkel, E. P. 2000. Anti-inflammatory activity of extracts and fractions from the leaves of Gochnatia polymorpha. Phytother. Res. 14:638-640.
66. Ueda, H., Yamazaki, C. and Yamazaki, M. 2002. Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens. Biol. Pharm. Bull. 25:1197-1202.
67. Petroni, A., Blasevic, M., Salami, M., Papii, N., Montedoro, G. F. and Galli, C. 1995. Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil. Thromb. Res. 78:151-160.
68. Miles, E. A., Zoubouli, P. and Calder, P. C. 2005. Differential anti-inflammatory effects of phenolic compounds from extra virgin olive oil identified in human whole blood cultures. Nutrition 21:389-394.