Abstract
Olive mill by-products are effluents generated during olive oil production process. The two-phase centrifugation system produces a semi-solid olive pomace called “alperujo.” This by-product is a combination of liquid and solid wastes derived from the three-phase manufacturing process. A direct and fast analytical method by ultra-high-pressure liquid chromatography-DAD coupled with ESI/MS-MS has been developed for the profiling of phenolic compounds. Thirty-five metabolites belonging to phenyl alcohols, secoiridoids, flavonoids, and iridoids were identified as the main constituents of alperujo in 12 min, including p-coumaroyl aldarate and a verbascoside derivative found for the first time in alperujo and a new ligstroside derivative. Six quantitatively significant components were determined at concentrations ranging from 17.7 mg/L for p-coumaric acid to 370.7 mg/L for hydroxytyrosol. Our data confirm that alperujo is an interesting source of phenolic compounds that could be extracted for use as nutraceuticals.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Change history
22 November 2017
The original version of this article unfortunately contained a mistake. The sentence in the abstract section should read “A direct and fast analytical method by ultra-high-performance liquid chromatography-DAD coupled with ESI/MS-MS has been developed for the profiling of phenolic compounds.”
References
Alburquerque JA, Gonzálvez J, García D, Cegarra J (2006) Measuring detoxification and maturity in compost made from “alperujo”, the solid by-product of extracting olive oil by the two-phase centrifugation system. Chemosphere 64:470–477
Aranda E, García-Romera I, Ocampo JA, Carbone V, Mari A, Malorni A, Sannino F, De Martino A, Capasso R (2007) Chemical characterization and effects on Lepidium sativum of the native and bioremediated components of dry olive mill residue. Chemosphere 69:229–239
Bouaziz M, Jemai H, Khabou W, Sayadi S (2010) Oil content, phenolic profiling and antioxidant potential of Tunisian olive drupes. J Sci Food Agric 90:1750–1758
Cardinali A, Pati S, Minervini F, D’Antuono I, Linsalata V, Lattanzio V (2012) Verbascoside, isoverbascoside, and their derivatives recovered from olive mill wastewater as possible food antioxidants. J Agric Food Chem 60:1822–1829
Cardoso SM, Guyot S, Marnet N, Lopes-da-Silva JA, Renard CM, Coimbra MA (2005) Characterisation of phenolic extracts from olive pulp and olive pomace by electrospray mass spectrometry. J Sci Food Agric 85:21–32
Cardoso SM, Falcão SI, Peres AM, Domingues MRM (2011) Oleuropein/ligstroside isomers and their derivatives in Portuguese olive mill wastewaters. Food Chem 129:291–296
Conseil Oléicole International (2013) ECONOMIE: 1,5 milliards d’oliviers dans le monde—Olive Info
D’Antuono I, Kontogianni VG, Kotsiou K, Linsalata V, Logrieco AF, Tasioula-Margari M, Cardinali A (2014) Polyphenolic characterization of olive mill wastewaters, coming from Italian and Greek olive cultivars, after membrane technology. Food Res Int 65:301–310
Dermeche S, Nadour M, Larroche C, Moulti-Mati F, Michaud P (2013) Olive mill wastes: biochemical characterizations and valorization strategies. Process Biochem 48:1532–1552
El-Abbassi A, Kiai H, Hafidi A (2012) Phenolic profile and antioxidant activities of olive mill wastewater. Food Chem 132:406–412
Giordano E, Dangles O, Rakotomanomana N, Baracchini S, Visioli F (2015) 3-O-Hydroxytyrosol glucuronide and 4-O-hydroxytyrosol glucuronide reduce endoplasmic reticulum stress in vitro. Food Funct 6:3275–3281
Herrero M, Temirzoda TN, Segura-Carretero A, Quirantes R, Plaza M, Ibañez E (2011) New possibilities for the valorization of olive oil by-products. J Chromatogr A 1218:7511–7520
Kalogerakis N, Politi M, Foteinis S, Chatzisymeon E, Mantzavinos D (2013) Recovery of antioxidants from olive mill wastewaters: a viable solution that promotes their overall sustainable management. J Environ Manag 128:749–758
Kanakis P, Termentzi A, Michel T, Gikas E, Halabalaki M, Skaltsounis A-L (2013) From olive drupes to olive oil. An HPLC-Orbitrap-based qualitative and quantitative exploration of olive key metabolites. Planta Med 79:1576–1587
Kapellakis IE, Tsagarakis KP, Crowther JC (2008) Olive oil history, production and by-product management. Rev Environ Sci Biotechnol 7:1–26
Leouifoudi I, Zyad A, Amechrouq A, Oukerrou MA, Mouse HA, Mbarki M (2014) Identification and characterisation of phenolic compounds extracted from Moroccan olive mill wastewater. Food Sci Technol Camp 34:249–257
Lozano-Sánchez J, Castro-Puyana M, Mendiola J, Segura-Carretero A, Cifuentes A, Ibáez E (2014) Recovering bioactive compounds from olive oil filter cake by advanced extraction techniques. Int J Mol Sci 15:16270–16283
Niaounakis M, Halvadakis CP (2006) Olive processing waste management literature review and patent survey. Elsevier, Amsterdam; London
Obied HK, Allen MS, Bedgood DR, Prenzler PD, Robards K (2005) Investigation of Australian olive mill waste for recovery of biophenols. J Agric Food Chem 53:9911–9920
Obied HK, Bedgood DR, Prenzler PD, Robards K (2007a) Bioscreening of Australian olive mill waste extracts: biophenol content, antioxidant, antimicrobial and molluscicidal activities. Food Chem Toxicol 45:1238–1248
Obied HK, Bedgood DR, Prenzler PD, Robards K (2007b) Chemical screening of olive biophenol extracts by hyphenated liquid chromatography. Anal Chim Acta 603:176–189
Ollivier D, Pinatel C, Ollivier V, Artaud J (2014) Composition en acides gras et en triglycérides d’huiles d’olive vierges de 34 variétés et 8 Appellations d’Origine Françaises et de 2 variétés étrangères implantées en France: Constitution d’une banque de données (1ère partie). Olivae 36–48
Peralbo-Molina Á, Priego-Capote F, Luque de Castro MD (2012) Tentative identification of phenolic compounds in olive pomace extracts using liquid chromatography–tandem mass spectrometry with a quadrupole–quadrupole-time-of-flight mass detector. J Agric Food Chem 60:11542–11550
Priego-Capote F, Ruiz-Jiménez J, Luque de Castro M (2004) Fast separation and determination of phenolic compounds by capillary electrophoresis–diode array detection. J Chromatogr A 1045:239–246
Rubio-Senent F, Rodríguez-Gutíerrez G, Lama-Muñoz A, Fernández-Bolaños J (2012) New phenolic compounds hydrothermally extracted from the olive oil byproduct alperujo and their antioxidative activities. J Agric Food Chem 60:1175–1186
Rubio-Senent F, Rodríguez-Gutiérrez G, Lama-Muñoz A, Fernández-Bolaños J (2013) Phenolic extract obtained from steam-treated olive oil waste: characterization and antioxidant activity. LWT—Food Sci Technol 54:114–124
Rubio-Senent F, Martos S, Lama-Muñoz A, Fernández-Bolaños JG, Rodríguez-Gutiérrez G, Fernández-Bolaños J (2015) Isolation and identification of minor secoiridoids and phenolic components from thermally treated olive oil by-products. Food Chem 187:166–173
Sanz M, Simón BF, Cadahía E, Esteruelas E, Muñoz AM, Hernández T, Estrella I, Pinto E (2012) LC-DAD/ESI-MS/MS study of phenolic compounds in ash (Fraxinus excelsior L. and F. americana L.) heartwood. Effect of toasting intensity at cooperage: LC-DAD/ESI-MS/MS of ash wood phenolic compounds. J Mass Spectrom 47:905–918
Savarese M, Demarco E, Sacchi R (2007) Characterization of phenolic extracts from olives (Olea europaea cv. Pisciottana) by electrospray ionization mass spectrometry. Food Chem 105:761–770
Silva S, Gomes L, Leitao F, Coelho AV, Boas LV (2006) Phenolic compounds and antioxidant activity of Olea europaea L. fruits and leaves. Food Sci Technol Int 12:385–395
Silva S, Gomes L, Leitão F, Bronze M, Coelho AV, Boas LV (2010) Secoiridoids in olive seed: characterization of nüzhenide and 11-methyl oleosides by liquid chromatography with diode array and mass spectrometry. Grasas Aceites 61:157–164
Steingass CB, Glock MP, Schweiggert RM, Carle R (2015) Studies into the phenolic patterns of different tissues of pineapple (Ananas comosus [L.] Merr.) infructescence by HPLC-DAD-ESI-MS n and GC-MS analysis. Anal Bioanal Chem 407:6463–6479
Suárez M, Macià A, Romero M-P, Motilva M-J (2008) Improved liquid chromatography tandem mass spectrometry method for the determination of phenolic compounds in virgin olive oil. J Chromatogr A 1214:90–99
Suárez M, Romero M-P, Ramo T, Macià A, Motilva M-J (2009) Methods for preparing phenolic extracts from olive cake for potential application as food antioxidants. J Agric Food Chem 57:1463–1472
Visioli F, Bernardini E (2011) Extra virgin olive oil’s polyphenols: biological activities. Curr Pharm Des 17:786–804
Acknowledgements
This work was supported by the SFR TERSYS, University of Avignon. We thank Mr. Jean-Benoît Hugues and his team (Moulin Castelas, Baux-de-Provence, France) for providing us the two-phase olive pomace.
Funding
This study was funded by the SFR TERSYS, University of Avignon.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of Interest
Aurélia Malapert declares that she has no conflict of interest. Emmanuelle Reboul declares that she has no conflict of interest. Michèle loonis declares that she has no conflict of interest. Olivier Dangles declares that he has no conflict of interest. Valérie Tomao declares that she has no conflict of interest.
Ethical Approval
This article does not contain any studies with human participants or animals performed by any of the authors.
Informed Consent
Not applicable.
Additional information
A correction to this article is available online at https://doi.org/10.1007/s12161-017-1107-8.
Rights and permissions
About this article
Cite this article
Malapert, A., Reboul, E., Loonis, M. et al. Direct and Rapid Profiling of Biophenols in Olive Pomace by UHPLC-DAD-MS. Food Anal. Methods 11, 1001–1010 (2018). https://doi.org/10.1007/s12161-017-1064-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12161-017-1064-2