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Pinoresinol and 1-acetoxypinoresinol, two new phenolic compounds identified in olive oil

  • Manuel Brenes
  • Francisco J. Hidalgo
  • Aranzazu García
  • José J. Rios
  • Pedro García
  • Rosario Zamora
  • Antonio Garrido
Article

Abstract

Polyphenols of olive oil show autoprotective, sensory, and nutritional-therapeutic effects. Two new phenolic compounds have been isolated from virgin olive oils by preparative high-performance liquid chromatography and their structures established on the basis of their mass spectra and nuclear magnetic resonance spectral data. The compounds identified are the lignans pinoresinol and 1-acetoxypinoresinol. Both have been found in all the commercial virgin olive oils analyzed. Pinoresinol concentration was rather similar in all the oils. In contrast, 1-acetoxypinoresinol concentration was higher in oils of the Arbequina and Empeltre cultivars than in Picual or Picudo cultivars. Pinoresinol and 1-acetoxypinoresinol may represent the major phenolic compounds in some Arbequina and Empeltre oils. Lignans possess biological and pharmacological properties and, therefore, the two new compounds identified in olive oils may contribute to the reported beneficial effects which are attributed to polyphenols on human health of a diet rich in olive oil.

Key Words

1-Acetoxypinoresinol MS NMR olive oil phenols pinoresinol 

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References

  1. 1.
    Willet, W.C., S. Sacks, A. Trichopoulou, G. Drescher, A. Ferro-Luzi, E. Helsing, and D. Trichopoulos, Mediterranean Diet Pyramid a Cultural Model for Healthy Eating, Am. J. Clin. Nutr. 61:1402S-1406S (1995).Google Scholar
  2. 2.
    Lipworth, L., M.E. Martinez, J. Angell, C.C. Hsien, and D. Trichopoulos, Olive Oil and Human Cancer, an Assessment of the Evidence, Prev. Med. 26:81–190 (1997).CrossRefGoogle Scholar
  3. 3.
    Wiseman, S.A., J.N. Mathot, N.J. de Fouw, and L.B. Tijburg, Dietary Non-tocopherol Antioxidants Present in Extra Virgin Olive Oil Increase the Resistance of Low Density Lipoproteins to Oxidation in Rabbits, Atherosclerosis 120:15–23 (1996).CrossRefGoogle Scholar
  4. 4.
    Visioli, F., and C. Galli, Olive Oil Phenols and Their Potential Effects on Human Health, J. Agric. Food Chem. 46:4292–4296 (1998).CrossRefGoogle Scholar
  5. 5.
    Montedoro, G.F., M. Servili, M. Baldioli, R. Selvaggini, E. Miniati, and A. Macchioni, Simple and Hydrolyzable Compounds in Virgin Olive Oil. 3. Spectroscopic Characterization of the Secoiridoid Derivatives, ——Ibid. 41:2228–2234 (1993).CrossRefGoogle Scholar
  6. 6.
    Cortesi, N., M. Azzolini, P. Rovellini, and E.I. Fedeli, Minor Polar Components of Virgin Olive Oils: A Hypothetical Structure by LC-MS, Riv. Ital. Sostanze Grasse 72:241–251 (1995).Google Scholar
  7. 7.
    Angerosa, F., N. d'Alessandro, F. Corana, and G. Mellerio, Characterization of Phenolic and Secoiridoid Aglycons Present in Virgin Oil by Gas Chromatography-Chemical Ionization Mass Spectrometry, J. Chromatogr. A 736:195–203 (1996).CrossRefGoogle Scholar
  8. 8.
    Pirisi, F., A. Angioni, P. Cabras, V.L. Garau, M.L. Sanjust di Teulada, M. Kaim dos Santos, and G. Bandino, Phenolic Compounds in Virgin Olive Oils. I. Low-Wavelength Quantitative Determination of Complex Phenols by High-Performance Liquid Chromatography Under Isocratic Elution, ——Ibid. 768:207–213 (1997).CrossRefGoogle Scholar
  9. 9.
    Manna, C., P. Galletti, V. Cucciolla, G.F. Montedoro, and V. Zappia, Olive Oil Hydroxytyrosol Protects Human Erythrocytes Against Oxidative Damages, J. Nutr. Biochem. 10:159–165 (1999).CrossRefGoogle Scholar
  10. 10.
    Giovannini, C., E. Straface, D. Modesti, E. Coni, A. Cantafora, M. De Vincenzi, W. Malorni, and R. Masella, Tyrosol, the Major Olive Oil Biophenol, Protects against Oxidized-LDL-Induced Injury in Caso-2-Cell, J. Nutr. 129:1269–1277 (1999).Google Scholar
  11. 11.
    Rovellini, P., N. Cortesi, and E.I. Fedeli, Analysis of Flavonoids from Olea europaea by HPLC-UV and HPLC-Electrospray-MS, Riv. Ital. Sostanze Grasse 74:273–279 (1997).Google Scholar
  12. 12.
    Bianco, A., R.A. Mazzei, C. Melchioni, G. Romeo, M.L. Scarpati, A. Soriero, and N. Uccella, Microcomponents of Olive Oil-III. Glucosides of 2(3,4-dihydroxyphenyl) Ethanol, Food Chem. 63:461–464 (1998).CrossRefGoogle Scholar
  13. 13.
    Brenes, M., A. García, P. García, J.J. Rios, and A. Garrido, Phenolic Compounds in Spanish Olive Oils, J. Agric. Food Chem. 47:3535–3540 (1999).CrossRefGoogle Scholar
  14. 14.
    Montedoro, G.F., M. Servili, M. Baldioli, and E. Miniati, Simple and Hydrolyzable Phenolic Compounds in Virgin Olive Oil. 2. Initial Characterization of the Hydrolyzable Fraction, ——Ibid. 40:1577–1580 (1992).CrossRefGoogle Scholar
  15. 15.
    Montedoro, G.F., M. Servili, M. Baldioli, and E. Miniati, Simple and Hydrolyzable Phenolic Compounds in Virgin Olive Oil. 1. Their Extraction, Separation and Quantitative and Semiquantitative Evaluation by HPLC, ——Ibid. 40:1571–1576 (1992).CrossRefGoogle Scholar
  16. 16.
    Hidalgo, F.J., R. Zamora, and E. Vioque, Syntheses and Reactions of Methyl (Z)-9,10-Epoxy-13-oxo-(E)-11-octadecenoate and Methyl (E)-9,10-Epoxy-13-oxo-(E)-11-octadecenoate, Chem. Phys. Lipids 60:225–233 (1992).CrossRefGoogle Scholar
  17. 17.
    Servili, M., M. Baldioli, R. Selvaggini, E. Miniati, A. Macchioni, and G.F. Montedoro, High-Performance Liquid Chromatography Evaluation of Phenols in Olive Fruit, Virgin Oil, Vegetation Waters, and Pomace and 1D- and 2D-Nuclear Magnetic Resonance Characterization, J. Am. Oil Chem. Soc. 76:873–882 (1999).Google Scholar
  18. 18.
    Pretsch, E., T. Clerc, J. Seibl, and W. Simon, Tabellen sur Strukturaufklärung Organischer Verbindungen mit Spektroskopischen Metoden, Springer-Verlag, Berlin, 1976.Google Scholar
  19. 19.
    Tsukamoto, H., S. Hisada, and S. Nishibe, Lignans from Bark of the Olea Plants. I, Chem. Pharm. Bull. 32:2730–2735 (1984).Google Scholar
  20. 20.
    Harborne, J.B., and H. Baxter, Phytochemical Dictionary: A Handbook of Bioactive Compounds, Taylor and Francis, Philadelphia, 1999, pp. 480–490.Google Scholar
  21. 21.
    Lin-gen, Z., O. Seligmann, K. Jurcic, and H. Wagner, Constituents of Daphne tangutica, Planta Med. 45:172–176 (1982).Google Scholar
  22. 22.
    Katayama, T., L.B. Davin, and N.G. Lewis, An Extraordinary Accumulation of (-)-Pinoresinol in Cell-Free Extracts of Forsythia intermedia: Evidence for Enantiospecific Reduction of (+)-Pinoresinol, Phytochemistry 31:3875–3881 (1992).CrossRefGoogle Scholar
  23. 23.
    Nikaido, T., T. Ohmoto, T. Kinoshita, U. Sankawa, S. Nishibe, and S. Hisada, Inhibition of Cyclic AMP Phosphodiesterase by Lignans, Chem. Pharm. Bull. 29:3586–3592 (1981).Google Scholar
  24. 24.
    MacRae, W.D., and G.H.N. Towers, Biological Activities of Lignans, Phytochemistry 23:1207–1220 (1984).CrossRefGoogle Scholar
  25. 25.
    Oomah, B.D., and G. Mazza, Flaxseed Products for Disease Prevention, in Functional Foods, edited by G. Mazza, Technomic Publishing Company, Inc., Lancaster, 1998, pp. 91–138.Google Scholar
  26. 26.
    Sih, C.J., P.R. Ravikumar, F.-C. Huang, C. Buckner, and H. Whitlock, Isolation and Synthesis of Pinoresinol Diglucoside, a Major Antihypertensive Principle of Tu-Chung (Eucommia ulmoides, Oliver), J. Am. Chem. Soc. 98:5412–5413 (1976).CrossRefGoogle Scholar
  27. 27.
    Kawagishi, S., T. Oosawa, and H. Katsuzaki, Pinoresinol Glucoside, Sesame Seed Extract Containing Glycoside, and Its Use for Preventing Oxidation of Lipids, Jpn. Patent 6116282, 1994, pp. 1–5.Google Scholar
  28. 28.
    Meagher, L.P., G.R. Beecher, V.P. Flanagan, and N.W. Li, Isolation and Characterization of the Lignans, Isolariciresinol and Pinoresinol, in Flaxseed Meal, J. Agric. Food Chem. 47:3173–3180 (1999).CrossRefGoogle Scholar
  29. 29.
    Tsukamoto, H., S. Hisada, and S. Nishibe, Lignans from Bark of the Olea Plants. II, Chem. Pharm. Bull. 33:1232–1241 (1985).Google Scholar
  30. 30.
    Tanahashi, T., N. Nagakura, K. Inoue, H. Inouye, and T. Shingu, Sambacolignoside, a New Lignan-Secoiridoid Glucoside from Jasminum sambac, Chem. Pharm. Bull. 35:5032–5035 (1987).Google Scholar

Copyright information

© AOCS Press 2000

Authors and Affiliations

  • Manuel Brenes
    • 1
  • Francisco J. Hidalgo
    • 1
  • Aranzazu García
    • 1
  • José J. Rios
    • 1
  • Pedro García
    • 1
  • Rosario Zamora
    • 1
  • Antonio Garrido
    • 1
  1. 1.Food Biotechnology Department, Instituto de la GrasaCSICSevillaSpain

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