Chemical and Biological Investigation of Olive Mill Waste Water – OMWW Secoiridoid Lactones^[*]

Abstract

Olive mill waste water is the major byproduct of the olive oil industry containing a range of compounds related to Olea europaea and olive oil constituents. Olive mill waste water comprises an important environmental problem in olive oil producing countries, but it is also a valuable material for the isolation of high added value compounds. In this study, an attempt to investigate the secoiridoid content of olive mill waste water is described with the aid of ultrahigh-performance liquid chromatography-electrospray ionization (±)-high-resolution mass spectrometry and centrifugal partition chromatography methods. In total, seven secoiridoid lactones were isolated, four of which are new natural products. This is the first time that a conjugate of hydroxytyrosol and a secoiridoid lactone has been isolated from olive mill waste water and structurally characterized. Furthermore, the range of isolated compounds allowed for the proposal of a hypothesis for the biotransformation of olive secoiridoids during the production of olive mill waste water. Finally, the ability of the representative compounds to reduce the intracellular reactive oxygen species was assessed with the dichlorofluorescein assay in conjunction with the known antioxidant agent hydroxytyrosol.

Key words

Olea europaea - Oleaceae - Olive mill waste water (OMWW) - olive oil - secoiridoid lactones - oleacein - oleuropein

• References

• 1 López-Miranda J, Pérez-Jiménez F, Ros E, De Caterina R, Badimón L, Covas MI, Escrich E, Ordovás JM, Soriguer F, Abiá R, Alarcón de la Lastra C, Battino M, Corella D, Chamorro-Quirós J, Delgado-Lista J, Giugliano D, Esposito K, Estruch R, Fernandez-Real JM, Gaforio JJ, La Vecchia C, Lairon D, López-Segura F, Mata P, Menéndez JA, Muriana FJ, Osada J, Panagiotakos DB, Paniagua JA, Pérez-Martinez P, Perona J, Peinado MA, Pineda-Priego M, Poulsen HE, Quiles JL, Ramírez-Tortosa MC, Ruano J, Serra-Majem L, Solá R, Solanas M, Solfrizzi V, de la Torre-Fornell R, Trichopoulou A, Uceda M, Villalba-Montoro JM, Villar-Ortiz JR, Visioli F, Yiannakouris N. Olive oil and health: summary of the II international conference on olive oil and health consensus report, Jaén and Córdoba (Spain) 2008. Nutr Metab Cardiovasc Dis 2010; 20: 284-294
• 2 Di Giovacchino L, Costantini N, Serraiocco A, Surricchio G, Basti C. Natural antioxidants and volatile compounds of virgin olive oils obtained by two or three-phases centrifugal decanters. Eur J Lipid Sci Tech 2001; 103: 279-285
• 3 Justino C, Pereira R, Freitas A, Rocha-Santos T, Panteleitchouk T, Duarte A. Olive oil mill wastewaters before and after treatment: a critical review from the ecotoxicological point of view. Ecotoxicology 2012; 21: 615-629
• 4 Elmekawy A, Diels L, Bertin L, De Wever H, Pant D. Potential biovalorization techniques for olive mill biorefinery wastewater. Biofuel Bioprod Bior 2014; 8: 283-293
• 5 Ganzenko O, Huguenot D, van Hullebusch ED, Esposito G, Oturan MA. Electrochemical advanced oxidation and biological processes for wastewater treatment: A review of the combined approaches. Environ Sci Pollut R 2014; 21: 8493-8524
• 6 Appels L, Dewil R. Biomass valorization to energy and value added chemicals: The future of chemical industry. Resour Conserv Recy 2012; 59: 1-3
• 7 Obied HK, Allen MS, Bedgood DR, Prenzler PD, Robards K, Stockmann R. Bioactivity and analysis of biophenols recovered from olive mill waste. J Agric Food Chem 2005; 53: 823-837
• 8 Cardinali A, Cicco N, Linsalata V, Minervini F, Pati S, Pieralice M, Tursi N, Lattanzio V. Biological activity of high molecular weight phenolics from olive mill wastewater. J Agric Food Chem 2010; 58: 8585-8590
• 9 Capasso R, de Martino A, Arienzo M. Recovery and characterization of the metal polymeric organic fraction (polymerin) from olive oil mill wastewaters. J Agric Food Chem 2002; 50: 2846-2855
• 10 Lemus C, Angelis A, Halabalaki M, Skaltsounis AL. γ-Oryzanol. An attractive bioactive component from rice bran. In: Watson RR, Preedy V, Zibadi S, editors Wheat and rice in disease prevention and health. London: Elsevier, Inc.; 2014: 409-430
• 11 Zoidou E, Agalias A, Magiatis P, Skaltsounis AL. New iridoid derivatives from table olives cv Throuba Thassos and olive mill waste waters. Planta Med 2008; 74: PB168
• 12 Agalias A, Magiatis P, Skaltsounis AL, Mikros E, Tsarbopoulos A, Gikas E, Spanos I, Manios T. A new process for the management of olive oil mill waste water and recovery of natural antioxidants. J Agric Food Chem 2007; 55: 2671-2676
• 13 Gil M, Haïdour A, Ramos JL. Two glutaric acid derivatives from olives. Phytochemistry 1998; 49: 1311-1315
• 14 Damak N, Allouche N, Hamdi B, Litaudon M, Damak M. New secoiridoid from olive mill wastewater. Nat Prod Res 2011; 26: 125-131
• 15 Napora-Wijata K, Robins K, Osorio-Lozada A, Winkler M. Whole-cell carboxylate reduction for the synthesis of 3-hydroxytyrosol. ChemCatChem 2014; 6: 1089-1095
• 16 Cardinali A, Pati S, Minervini F, DʼAntuono I, Linsalata V, Lattanzio V. Verbascoside, isoverbascoside, and their derivatives recovered from olive mill wastewater as possible food antioxidants. J Agric Food Chem 2012; 60: 1822-1829
• 17 Mousouri E, Melliou E, Magiatis P. Isolation of megaritolactones and other bioactive metabolites from ʼMegaritikiʼ table olives and debittering water. J Agric Food Chem 2014; 62: 660-667
• 18 Kanakis P, Termentzi A, Michel T, Gikas E, Halabalaki M, Skaltsounis AL. From olive drupes to olive oil. An HPLC-orbitrap-based qualitative and quantitative exploration of olive key metabolites. Planta Med 2013; 79: 1576-1587
• 19 Piperno A, Toscano M, Uccella NA. The Cannizzaro-like metabolites of secoiridoid glucosides in some olive cultivars. J Sci Food Agr 2004; 84: 341-349
• 20 Macahig RA, Harinantenaina L, Matsunami K, Otsuka H, Takeda Y, Shinzato T. Secoiridoid and iridoid glucosides from the leaves of Fraxinus griffithii . J Nat Med 2010; 64: 1-8
• 21 Bianco AD, Piperno A, Romeo G, Uccella N. NMR experiments of oleuropein biomimetic hydrolysis. J Agric Food Chem 1999; 47: 3665-3668