Hostname: page-component-78c5997874-v9fdk Total loading time: 0 Render date: 2024-11-09T01:32:13.441Z Has data issue: false hasContentIssue false
  • English
  • Français

Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in ‘orujo’ olive oil, on rat aorta

Published online by Cambridge University Press:  09 March 2007

Rosalía Rodríguez-Rodríguez ,
María Dolores Herrera ,
Javier S. Perona  and
Valentina Ruiz-Gutiérrez
Rosalía Rodríguez-Rodríguez
Affiliation:
Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avda Padre García Tejero n. 4, 41012 Sevilla, Spain
María Dolores Herrera
Affiliation:
Departamento de Farmacología, Facultad de Farmacia, Universidad de Sevilla, C/Profesor García González n. 2, 41012 Sevilla, Spain
Javier S. Perona
Affiliation:
Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avda Padre García Tejero n. 4, 41012 Sevilla, Spain
Valentina Ruiz-Gutiérrez*
Affiliation:
Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avda Padre García Tejero n. 4, 41012 Sevilla, Spain
*
*Corresponding author: Dr V. Ruiz-Gutiérrez, fax +34 954616790, email [email protected]
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the ‘Save PDF’ action button.

‘Orujo’ olive oil is obtained by chemical processes from the waste resulting from the mechanical extraction of virgin olive oil. The aim of the present study was to evaluate a new pharmacological property of two natural triterpenoids contained in olive oil, as vasodilatory agents, and to determine their mechanism of action. The two compounds studied were oleanolic acid and erythrodiol. The vasorelaxant effect induced by these pentacyclic triterpenoids was studied in isolated thoracic rat aorta. Oleanolic acid and erythrodiol, accumulatively added, showed vasorelaxant activities in aortic rings with endothelium pre-contracted by 10−6 M-phenylephrine (maximum percentage of relaxation 86·38 (SEM 2·89) and 73·53 (SEM 6·01), respectively). They had almost no relaxant effect on depolarised or endothelium-denuded aortic segments. The relaxation was significantly attenuated by pre-treatment with the NO synthase inhibitor Nω-nitro-L-arginine-methylester (L-NAME; 3×10−4 m). To characterise the involvement of endothelial factors, in addition to NO, arteries with endothelium were exposed to 10−5 M-indomethacin (INDO), a cyclo-oxygenase inhibitor, or INDO plus L-NAME. INDO did not have any significant effect on the relaxant response of both compounds. The combination of L-NAME plus INDO only abolished the oleanolic acid-induced relaxation. The present results suggest that the mechanism of relaxation seems to be mainly mediated by the endothelial production of NO; however, other mechanisms cannot be excluded. It can be concluded that oleanolic acid and erythrodiol may have interesting therapeutic potential as new vasodilator drugs, thus protecting the cardiovascular system. Therefore, the intake of ‘orujo’ olive oil, as a source of these compounds, might be beneficial in this regard.

Keywords

‘Orujo’ olive oilOleanolic acidErythrodiolVasorelaxationEndotheliumRat aorta
Type
Research Article
Information
British Journal of Nutrition , Volume 92 , Issue 4 , October 2004 , pp. 635 - 642
Copyright
Copyright © The Nutrition Society 2004

References

Álvarez, de, Sotomayor, M, Pérez-Guerrero, C, Herrera, MD & Marhuenda, E (2001) Effect of simvastatin on vascular smooth muscle responsiveness: involvement of Ca(2+) homeostasis. Eur J Pharmacol 415, 217–224.CrossRefGoogle Scholar
American Dietetic Association (1999) Position of the American Dietetic Association: functional foods. J Am Diet Assoc 99, 1278–1285.CrossRefGoogle Scholar
Boulanger, CM (1999) Secondary endothelial dysfunction: hypertension and heart failure. J Mol Cell Cardiol 31, 39–49.CrossRefGoogle ScholarPubMed
Choi, CY, You, HJ & Jeong, HG (2001) Nitric oxide and tumor necrosis factor-alpha production by oleanolic acid via nuclear factor-kappaB activation in macrophages. Biochem Biophys Res Commun 288, 49–55.CrossRefGoogle ScholarPubMed
De la Puerta, R, Martínez-Domínguez, E, Ruíz-Gutiérrez, V (2000) Effect of minor components of virgin olive oil on topical antiinflammatory assays. Z Naturforsch 55, 814–819.CrossRefGoogle ScholarPubMed
De la Puerta, R, Ruíz-Gutiérrez, V, Hoult, JRS (1999) Inhibition of leukocyte 5-lipooxygenase by phenolics from virgin olive oil. Biochem Pharmacol 57, 445–449.CrossRefGoogle Scholar
Furchgott, RF & Vanhoutte, PM (1989) Endothelium-derived relaxing and contracting factors. FASEB J 3, 2007–2018.CrossRefGoogle ScholarPubMed
Furchgott, RF & Zawadzki, JV (1980) The obligatory role of endothelial cells in the relaxation of arterial smooth muscle by acetylcholine. Nature 299, 373–376.CrossRefGoogle Scholar
Godfraind, T, Miller, R & Wibo, M (1986) Calcium antagonism and calcium entry blockade. Pharmacol Rev 38, 321–416.Google ScholarPubMed
Honda, T, Rounds, BV, Bore, L, Finlay, HJ, Favaloro, FG Jr, Suh, N, Wang, Y, Sporn, MB, Gribble, GW (2000) Synthetic oleanane and ursane triterpenoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages. J Med Chem 43, 4233–4246.CrossRefGoogle Scholar
Hsu, HY, Yang, JJ & Lin, CC (1997) Effects of oleanolic acid and ursolic acid on inhibiting tumor growth and enhancing the recovery of hematopoietic system postirradiation in mice. Cancer Lett 111, 7–13.CrossRefGoogle ScholarPubMed
Kashiwada, Y, Wang, HK & Nagao, T (1998) Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids. J Nat Prod 61, 1090–1095.CrossRefGoogle ScholarPubMed
Keys, A (1995) Mediterranean diet and public health: personal reflections. Am J Clin Nutr 61, 1321S–1323S.CrossRefGoogle Scholar
Kim, ND, Kang, SY & Schini, VB (1994) Gingenosides evoke endothelium-dependent vascular relaxation in rat aorta. Gen Pharmacol 25, 1071–1077.CrossRefGoogle ScholarPubMed
Laight, DW, Kaw, AV, Carrier, MJ & Anggard, EE (1998) Interaction between superoxide anion and nitric oxide in the regulation of vascular endothelial function. Br J Pharmacol 124, 238–244.CrossRefGoogle ScholarPubMed
Libby, P (2002) Inflammation and atherosclerosis. Nature 420, 868–874.CrossRefGoogle Scholar
Liu, J (1995) Pharmacology of oleanolic acid and ursolic acid. J Ethnopharmacol 49, 57–68.CrossRefGoogle ScholarPubMed
Liu, Y, Hartley, DP & Liu, J (1998) Protection against carbon tetrachloride hepatotoxicity by oleanolic acid is not mediated through metallothionein. Toxicol Lett 95, 77–85.CrossRefGoogle Scholar
Lückhoff, A, Pohl, U, Mulsch, A & Busse, R (1988) Differential role of extra- and intracellular calcium in the release of EDRF and prostacyclin from cultured endothelial cells. Br J Pharmacol 95, 189–196.CrossRefGoogle ScholarPubMed
Lüscher, TF & Barton, M (1997) Biology of the endothelium. Clin Cardiol 20, Suppl. 2,II-3–II-10..CrossRefGoogle ScholarPubMed
Mañez, S, Recio, MC, Giner, RM, Ríos, JL (1997) Effect of selected triterpenoids on chronic dermal inflammation. Eur J Pharmacol 334, 103–105.CrossRefGoogle ScholarPubMed
Matsuda, H, Li, Y, Murakami, T, Matsumura, N, Yamahara, J & Yoshikawa, M (1998) Antidiabetic principles of natural medicines. III. Structure-related inhibitory activity and action mode of oleanolic acid glycosides on hypoglycemic activity. Chem Pharm Bull (Tokyo) 46, 1399–1403.CrossRefGoogle ScholarPubMed
Mengoni, F, Lichtner, M, Battinelli, L, Marzi, M, Mastroianni, CM, Vullo, V & Mazzanti, G (2002) In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells. Planta Med 68, 111–114.CrossRefGoogle ScholarPubMed
Mombouli, JV & Vanhoutte, PM (1999) Endothelial dysfunction: from physiology to therapy. J Mol Cell Cardiol 31, 61–74.CrossRefGoogle ScholarPubMed
Moncada, S, Palmer, RM & Higgs, EA (1991) Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev 43, 109–142.Google ScholarPubMed
Pérez-Camino, MC & Cert, A (1999) Quantitative determination of hydroxy pentacyclic triterpene acids in vegetable oils. J Agric Food Chem 47, 1558–1562.CrossRefGoogle ScholarPubMed
Perona, JS, Ruíz-Gutiérrez, V (2000) Effect of two high-oleic oils on the liver lipid composition of spontaneously hypertensive rats. Life Sci 66, 521–531.CrossRefGoogle ScholarPubMed
Recio, MC, Giner, RM, Mañez, S & Rios, JL (1995) Structural requirements for the anti-inflammatory activity of natural triterpenoids. Planta Med 61, 182–185.CrossRefGoogle ScholarPubMed
Ringbom, T, Segura, L, Noreen, Y, Perera, P & Bohlin, L (1998) Ursolic acid from Plantago major, a selective inhibitor of cyclooxygenase-2 catalyzed prostaglandin biosynthesis. J Nat Prod 61, 1212–1215.CrossRefGoogle Scholar
Somova, LI, Nadar, A, Rammanan, P & Shode, FO (2003 a) Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension. Phytomedicine 10, 115–121.CrossRefGoogle ScholarPubMed
Somova, LI, Shode, FO, Ramnanan, P & Nadar, A (2003 b) Antihypertensive, antiatherosclerotic and antioxidant activity of triterpenoids isolated from Olea europaea, subspecies africana leaves. J Ethnopharmacol 84, 299–305.CrossRefGoogle ScholarPubMed
Tanner, MA, Bu, X, Steimle, JA & Myers, PR (1999) The direct release of nitric oxide by gypenosides derived from the herb Gynostemma pentaphyllum. Nitric Oxide 3, 359–365.CrossRefGoogle ScholarPubMed
Vanhoutte, PM (2001) Endothelium-derived free radicals: for worse and for better. J Clin Invest 107, 23–25.CrossRefGoogle ScholarPubMed
Vázquez-Roncero, A & Janer, ML (1969) Ácidos triterpénicos del olivo (Triterpenoid acids of the olive tree). Grasas y Aceites 20, 133–138.Google Scholar
Vioque, E & Maza, MP (1963) Sobre los ácidos triterpénicos del aceite de orujo y oliva (About orujo and olive oil triterpenic acids). Grasas y Aceites 14, 9–11.Google Scholar
Vioque, E & Morris, LJ (1961) Minor components of olive oils. I. Triterpenoid acids in an acetone-extracted orujo oil. J Am Oil Chem Soc 38, 485–488.CrossRefGoogle Scholar
Visioli, F & Galli, C (1998) The effect of minor constituents of olive oil on cardiovascular disease: new findings. Nutr Rev 56, 142–147.CrossRefGoogle ScholarPubMed
Yang, D, Feletou, M, Boulanger, CM, Wu, HF, Levens, N, Zhang, JN & Vanhoutte, PM (2002) Oxygen-derived free radicals mediate endothelium-dependent contractions to acetylcholine in aortas from spontaneously hypertensive rats. Br J Pharmacol 136, 104–110.CrossRefGoogle ScholarPubMed
Yim, TK, Wu, WK, Pak, WF & Ko, KM (2001) Hepatoprotective action of an oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice. Phytother Res 15, 589–592.CrossRefGoogle ScholarPubMed
Yoshikawa, M & Matsuda, H (2000) Antidiabetogenic activity of oleanolic acid glycosides from medicinal foodstuffs. Biofactors 13, 231–237.CrossRefGoogle ScholarPubMed
Zheng, XF, Kwan, CY & Daniel, EE (1994) Role of intracellular Ca2+ in EDRF release in rat aorta. J Vasc Res 31, 18–24.CrossRefGoogle ScholarPubMed
Zhu, YM, Shen, JK, Wang, HK, Cosentino, LM & Lee, KH (2001) Synthesis and anti-HIV activity of oleanolic acid derivatives. Bioorg Med Chem Lett 11, 3115–3118.CrossRefGoogle ScholarPubMed