Skip to main content
Log in

Hydroxytyrosol and tyrosol as the main compounds found in the phenolic fraction of steam-exploded olive stones

  • Published:
Journal of the American Oil Chemists' Society

Abstract

The lignocellulosic by-products, whole stones, and seed husks obtained from processing pitted table olives and oil olives were pretreated under various conditions of steam explosion, with and without previous acid impregnation. The various water-soluble noncarbohydrate compounds generated during steam explosion, such as sugar degradation compounds (furfural and hydroxymethylfurfural), lignin degradation compounds (vanillic acid, syringic acid, vanillin, and syringaldehyde) and the simple phenolic compounds characteristic of olive fruit (tyrosol and hydroxytyrosol), were identified. The amount of hydroxytyrosol solubilized was higher than that of the other compounds, and increased with increasing steaming temperature and time. This suggests its presence as a structural component of the olive stone.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Garrido, A., Aceitunas de mesa en España. Una perpectiva actual, Olivae 50:21–27 (1994).

    Google Scholar 

  2. Mingo, M., and J.M. Romero, Estudio Químico-Analítico del Aceite de Huesos de Aceitunas, Rev. R. Acad. Cienc. Exactas Fis. Nat. Madrid 47:553–585 (1953).

    Google Scholar 

  3. Fernández-Díez, M.J., Las Protéinas de la Semilla de Aceitunas. La Fracción Soluble en Agua Destilada, Grases Aceites 11:19–25 (1960).

    Google Scholar 

  4. Rivas, M., Azúcares de la Semilla de Aceitunas I. Identificación por Cromatografía sobre Papel y Cromatofgrafía Gas-Líquido, Ibid.:13–16 (1983).

    Google Scholar 

  5. Maestro-Durán, R., R. León-Cabello, V. Ruíz-Gutiérrez, P. Fiestas, and A. Vázquez-Roncero, Glucósidos Fenólicos Amargos de las Semillas del Olivo (Olea europaea), Ibid.:332–335 (1994).

    Google Scholar 

  6. Heredia, A., R. Guillén, J. Fernández-Bolaños, and M. Rivas, Olive Stones as a Source of Fermentable Sugars, Biomass 14:143–148 (1987).

    Article  Google Scholar 

  7. Coimbra, M.A., K. Waldron, and R.R. Selvendran, Isolation and Characteristics of Cell Wall Polymers from Olive Pulp (Olea europaea), Carbohydrate Res. 252:245–262 (1994).

    CAS  Google Scholar 

  8. González, M.T., M. Molina-Sabio, and F. Rodríguez-Reinoso, Steam Activation of Olive Stone Chars in Development of Porosity, Carbon 32:1407–1413 (1994).

    Article  Google Scholar 

  9. Duff, S.J.B., and W.D. Murray, Bioconversion of Forest Products Industry Waste Cellulosics to Fuel Ethanol: A Review, Biores. Technol. 55:1–33 (1996).

    Article  CAS  Google Scholar 

  10. Vlasenko, E.Y., H. Ding, J.M. Labavitch, and S.P. Shoemaker, Enzymatic Hydrolysis of Pretreated Rice Straw, Ibid.:109–119 (1997).

    Article  CAS  Google Scholar 

  11. Donaldson, L.A., K.K.Y. Wong, and K.L. Mackie, Ultrastructure of Steam-Exploded Wood, Wood Sci. Technol. 22:103–114 (1988).

    Article  CAS  Google Scholar 

  12. Castro, F.B., P.M. Hotten, E.R. Orskov, and M. Rebeller, Inhibition of Rumen Microbes by Compounds Formed in the Steam Treatment of Wheat Straw, Biores. Technol. 50:25–30 (1994).

    Article  CAS  Google Scholar 

  13. Palmqvist, E., B. Hahn-Hägerdal, Z. Szengyel, G. Zacchi, and K. Rèczey, Simultaneous Detoxification and Enzyme Production of Hemicellulose Hydrolysates Obtained After Steam Pretreatment, Enz. Microb. Technol. 20:286–293 (1997).

    Article  CAS  Google Scholar 

  14. Ruíz-Barba, J.L., M. Brenes-Balbuena, R. Jiménez-Díaz, P. García-García, and A. Garrido-Fernández, Inhibition of Lactobacillus plantarum by Polyphenols Extracted from Two Different Kinds of Olive Brine, J. Appl. Bacteriol. 74:15–19 (1993).

    ADS  Google Scholar 

  15. Baldioli, M., M. Servili, G. Perretti, and G.F. Montedoro, Antioxidant Activity of Tocopherols and Phenolic Compounds of Virgin Olive Oil, J. Am. Oil Chem. Soc. 73:1589–1593 (1996).

    Article  CAS  Google Scholar 

  16. Heitz, M., F. Carrasco, M. Rubio, A. Brown, and E. Chornet, Physicochemical Characterization of Lignocellulosic Substrates Pretreated Via Autohydrolysis: An Application to Tropical Woods, Biomass 13:255–273 (1987).

    Article  CAS  Google Scholar 

  17. Graciani, E., and A. Vázquez, A Study of the Polar Compounds in Olive Oil by High Performance Liquid Chromatography (HPLC). Chromatography in Inverse Phase, Grasas Aceites 31:237–243 (1980).

    Google Scholar 

  18. Tanahashi, M., Characterization and Degradation Mechanism of Wood Components by Steam Explosion and Utilization of Exploded Wood, Wood Res. 77:49–117 (1990)

    CAS  Google Scholar 

  19. Mes-Hartree, M., and J.N. Saddler, The Nature of Inhibitory Materials Present in Pretreated Lignocellulosic Substrates Which Inhibit the Enzymatic Hydrolysis of Cellulose, Biotechnol. Lett. 5:531–536 (1983).

    Article  CAS  Google Scholar 

  20. Hishiyama, S., and K. Sudo, Degradation Mechanism of Lignin by Steam-Explosion, Mokuzai Gakkaishi 38:944–949 (1992).

    CAS  Google Scholar 

  21. Clark, T.A., and K.L. Mackie, Fermentation Inhibitors in Wood Hydrolysates Derived from the Softwood Pinus radiata, J. Chem. Tech. Biotechnol. 34:101–110 (1984).

    Google Scholar 

  22. Kuznetsov, B.N., A.A. Efrenov, V.A. Levdanskii, S.A. Kuznetsova, N.I. Polezhayeva, T.A. Shikina, and I.V. Krotova, The Use of Non-Isobaric Pre-Hydrolysis for the Isolation of Organic Compounds from Wood and Bark, Biores. Technol. 58:181–188 (1996).

    Article  CAS  Google Scholar 

  23. Scalbert, A., B. Monties, E. Guittet, and J.Y. Lallemand, Comparison of Wheat Straw Lignin Preparations. I. Chemical and Spectroscopic Characterization, Holzforschung 40:119–127 (1986).

    Article  CAS  Google Scholar 

  24. Burtscher, E., O. Bobleter, W. Schwald, R. Concin, and H. Binder, Chromatographic Analysis of Biomass Reaction Products Produced by Hydrothermolysis of Poplar Wood, J. Chromatogr. 390:401–412 (1987).

    Article  CAS  Google Scholar 

  25. Ando, S., Y. Arai, K. Koichi, and S. Hanai, Identification of Aromatic Monomers in Steam-Exploded Poplar and Their Influences on Ethanol Fermentation by Saccharomyces cerevisiae, J. Ferment. Technol. 64:567–570 (1986).

    Article  CAS  Google Scholar 

  26. Excoffier, G., A. Peguy, M. Rinaudo, and M.R. Vignon, Evolution of Lignocellulosic Components During Steam Explosion. Potential Applications, in Steam Explosion Techniques. Fundamentals and Industrial Applications, edited by B. Focher, V. Marzetti, and V. Crescenzi, Gordon and Breach Science Publishers, Amsterdam, 1990, pp. 53–56.

    Google Scholar 

  27. Marchal, R., M. Ropars, J. Pourquié, F. Fayole, and J.P. Vandecasteele, Large-Scale Enzymatic Hydrolysis of Agricultural Lignocellulosics Biomass. Part 2: Conversion into Acetone-Butanol, Biores. Technol. 42:205–217 (1992).

    Article  CAS  Google Scholar 

  28. Fleuriet, A., J.J. Machaix, C. Andary, and P. Villemur, Mise en evidence et dosage par chromatographie liquide à haute performance du verbascoside dans la fruit de six cultivars d’Olea europaea L. Cr. Acad. Sci. 7:253–256 (1984).

    Google Scholar 

  29. Brenes, M., L. Rejano, P. García, A.H. Sánchez, and A. Garrido, Biochemical Phenolic Compounds During Spanish-Style Green Olive Processing, J. Agric. Food Chem. 43:2702–2706 (1995).

    Article  CAS  Google Scholar 

  30. Wanasundara, P.K.J.P.D., F. Shahidi, and V.K.S. Shukla,

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Heredia.

About this article

Cite this article

Fernández-Bolaños, J., Felizón, B., Brenes, M. et al. Hydroxytyrosol and tyrosol as the main compounds found in the phenolic fraction of steam-exploded olive stones. J Amer Oil Chem Soc 75, 1643–1649 (1998). https://doi.org/10.1007/s11746-998-0106-8

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-998-0106-8

Key Words

Navigation