Identification and quantification of phenolic compounds in fresh and processed table olives of cv. ‘Kalamata’

  • Constantinos SALIS Agricultural University of Athens, School of Food, Biotechnology and Development, Department of Biotechnology, Genetics Laboratory, 75 Iera Odos 11855, Athens (GR)
  • Ioannis E. PAPADAKIS Agricultural University of Athens, School of Plant Sciences, Department of Crop Science, Pomology Laboratory, 75 Iera Odos 11855, Athens (GR)
  • Marianna HAGIDIMITRIOU Agricultural University of Athens, School of Food, Biotechnology and Development, Department of Biotechnology, Genetics Laboratory, 75 Iera Odos 11855, Athens (GR)
Keywords: HPLC-DAD, LC-(ESI)-MS/MS, Mediterranean diet, phenolic compounds, processing, table olives

Abstract

Mediterranean diet is almost synonymous to the healthy lifestyle and diet nowadays. Some of the major components of the diet are the products of the olive tree, fruits and olive oil, which are classified as medical foods, due to their nutraceutical benefits and their protective properties against cancer, cardiovascular diseases, age-related diseases, neurodegenerative disorders and other diseases. The key contributors to these properties are the phenolic compounds such as hydroxytyrosol, tyrosol and oleuropein. Table olives are being processed with several methods in order to reduce the bitterness of the olive fruit and the impact of the processing on phenolic compounds has not been studied extensively. In the present study, changes in the concentration of the most important phenolic compounds were quantified in fresh, Greek-style and Spanish-style processed olive fruits of cv. ‘Kalamata’, using two different analytical methods for identification and quantification: high-performance liquid chromatography diode array detector (HPLC-DAD) and ultrahigh-performance liquid chromatography tandem mass spectrometry (LC-(ESI)-MS/MS). The phenolic compounds that were identified and quantified were hydroxytyrosol, tyrosol, verbascocide, rutin, oleuropein and luteolin. Both processing methods used altered the phenolic compounds concentration in ‘Kalamata’ olive fruits compared to untreated fruits. In both analytical methods, a statistically significant increase in verbascoside and hydroxytyrosol concentration and a statistically significant decrease in rutin concentration was observed in both, Greek-style and Spanish-style, processed olive fruits.

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References

Akdemir Z, Kahraman, Ç, Tatlı I. I, Akkol E, K., Süntar I, Keles H (2011). Bioassay-guided isolation of anti-inflammatory, antinociceptive and wound healer glycosides from the flowers of Verbascum mucronatum Lam. Journal of Ethnopharmacology 136(3):436-443. https://doi.org/10.1016/j.jep.2010.05.059

Ambra R, Natella F, Bello C, Lucchetti S, Fort V, Pastore G (2017). Phenolics fate in table olives (Olea europaea L. cv. Nocellara del Belice) debittered using the Spanish and Castelvetrano methods. Food Research International 100:369-376. https://doi.org/10.1016/j.foodres.2017.07.027

Artajo LS, Romero MP, Suárez M (2007). Partition of phenolic compounds during the virgin olive oil industrial extraction process. European Food Research Technology 225:617-625. https://doi.org/10.1007/s00217-006-0456-0

Barbaro B, Toietta G, Maggio R, Arciello M, Tarocchi M, Galli A, Balsano C (2014). Effects of the olive-derived polyphenol oleuropein on human health. International Journal of Molecular Sciences 15(10):18508-18524. https://doi.org/10.3390/ijms151018508

Bartolini G, Petruccelli R (2002). Classification, origin, diffusion and history of the olive. Food & Agriculture Org.

Basdeki E, Salis C, Hagidimitriou M (2020). The effects of Mediterranean diet and EVOO consumption in relation to human health. Notulae Scientia Biologicae 12(3):466-485. http://doi.org/10.15835/nsb123107

Bendini A, Cerretani L, Carrasco-Pancorbo A, Gómez-Caravaca AM, Segura-Carretero A, Fernández-Gutiérrez A, Lercker G (2007). Phenolic molecules in virgin olive oils: a survey of their sensory properties, health effects, antioxidant activity and analytical methods. An overview of the last decade Alessandra. Molecules 12(8):1679-1719. https://doi.org/10.3390/12081679

Bianco A, Buiarelli F, Cartoni G, Coccioli F, Jasionowska R, Margherita P (2003). Analysis by liquid chromatography‐tandem mass spectrometry of biophenolic compounds in olives and vegetation waters. Part I. Journal of Separation Science 26(5):409-416. https://doi.org/10.1002/jssc.200390053

Blekas G, Vassilakis C, Harizanis C, Tsimidou M, Boskou DG (2002). Biophenols in table olives. Journal of Agricultural and Food Chemistry 50(13):3688-3692. https://doi.org/10.1021/jf0115138

Boskou D, Blekas G, Tsimidou M (2005). Phenolic compounds in olive oil and olives. Current Topics in Nutraceutical Research 3(2):125-136.

Brenes-Balbuena M, Garcia-Garcia P, Garrido-Fernandez A (1992). Phenolic compounds related to the black color formed during the processing of ripe olives. Journal of Agricultural and Food Chemistry 40(7):1192-1196. https://doi.org/10.1021/jf00019a023

Carrasco‐Pancorbo A, Neusüß C, Pelzing M, Segura‐Carretero A, Fernández‐Gutiérrez A (2007). CE‐and HPLC‐TOF‐MS for the characterization of phenolic compounds in olive oil. Electrophoresis 28(5):806-821. https://doi.org/10.1002/elps.200600382

Charoenprasert S, Mitchell A (2012). Factors influencing phenolic compounds in table olives (Olea europaea). Journal of Agricultural and Food Chemistry 60(29):7081-7095. https://doi.org/10.1021/jf3017699

Chang CY, Huang IT, Shih HJ, Chang YY, Kao MC, Shih PC, Huang CJ (2019). Cluster of differentiation 14 and toll-like receptor 4 are involved in the anti-inflammatory effects of tyrosol. Journal of Functional Foods 53:93-104. https://doi.org/10.1016/j.jff.2018.12.011

Cicerale S, Lucas LJ, Keast RSJ (2012). Antimicrobial, antioxidant and anti-inflammatory phenolic activities in extra virgin olive oil. Current Opinion in Biotechnology 23(2):129-135. https://doi.org/10.1016/j.copbio.2011.09.006

D’Antuono I, Garbetta A, Ciasca B, Linsalata V, Minervini F, Lattanzio VM, Cardinali A (2016). Biophenols from table olive cv Bella di Cerignola: Chemical characterization, bioaccessibility, and intestinal absorption. Journal of Agricultural and Food Chemistry 64(28):5671-5678. https://doi.org/10.1021/acs.jafc.6b01642

Di Benedetto R, Varì R, Scazzocchio B, Filesi C, Santangelo C, Giovannini C, Masella R (2007). Tyrosol, the major extra virgin olive oil compound, restored intracellular antioxidant defences in spite of its weak antioxidative effectiveness. Nutrition, Metabolism and Cardiovascular Diseases 17(7):535-545. https://doi.org/10.1016/j.numecd.2006.03.005

Dierkes G, Krieger S, Dück R, Bongartz A, Schmitz OJ, Hayen H (2012). High-performance liquid chromatography–mass spectrometry profiling of phenolic compounds for evaluation of olive oil bitterness and pungency. Journal of Agricultural and Food Chemistry 60(31):7597-7606. https://doi.org/10.1021/jf3020574

Esti M, Cinquanta L, La Notte E (1998). Phenolic compounds in different olive varieties. Journal of Agricultural and Food Chemistry 46:32-35. https://doi.org/10.1021/jf970391+

Fu S, Segura-Carretero A, Arraez-Roman D, Menendez JA, De La Torre A, Fernandez-Gutierrez A (2009). Tentative characterization of novel phenolic compounds in extra virgin olive oils by rapid-resolution liquid chromatography coupled with mass spectrometry. Journal of Agricultural and Food Chemistry 57(23):11140-11147. https://doi.org/10.1021/jf901590n

Gerber M, Hoffman R (2015). The Mediterranean diet: health, science and society. British Journal of Nutrition 113(S2):S4-S10. https://doi.org/10.1017/S0007114514003912

Hassen I, Casabianca H, Hosni K (2015). Biological activities of the natural antioxidant oleuropein: Exceeding the expectation – A mini-review. Journal of Functional Foods 18:926-940. https://doi.org/10.1016/j.jff.2014.09.001

Janbaz KH, Saeed SA, Gilani A (2002). Protective effect of rutin on paracetamol-and CCl4-induced hepatotoxicity in rodents. Fitoterapia 73(7-8):557-563. https://doi.org/10.1016/S0367-326X(02)00217-4

Javed H, Khan MM, Ahmad A, Vaibhav K, Ahmad ME, Khan A, Safhi MM (2012). Rutin prevents cognitive impairments by ameliorating oxidative stress and neuroinflammation in rat model of sporadic dementia of Alzheimer type. Neuroscience 210:340-352. https://doi.org/10.1016/j.neuroscience.2012.02.046

Jerman Klen T, Golc Wondra A, Vrhovšek U, Mozetič Vodopivec B (2015). Phenolic profiling of olives and olive oil process-derived matrices using UPLC-DAD-ESI-QTOF-HRMS analysis. Journal of Agricultural and Food Chemistry 63(15):3859-3872. https://doi.org/10.1021/jf506345q

Johnson R, Melliou E, Zweigenbaum J, Mitchell AE (2018). Quantitation of oleuropein and related phenolics in cured Spanish-style green, California-style black ripe, and Greek-style natural fermentation olives. Journal of Agricultural and Food Chemistry 66(9):2121-2128. https://doi.org/10.1021/acs.jafc.7b06025

Kanakis P, Termentzi A, Michel T, Gikas E, Halabalaki M, Skaltsounis AL (2013). From olive drupes to olive oil. An HPLC-orbitrap-based qualitative and quantitative exploration of olive key metabolites. Planta Medica 79(16):1576-1587. http://dx.doi.org/ 10.1055/s-0033-1350823

Karakaya S, Nehir ElS (1999). Quercetin, luteolin, apigenin and kaempferol contents of some foods. Food Chemistry 66:289-292. https://doi.org/10.1016/S0308-8146(99)00049-7

Karkoula E, Skantzari A, Melliou E, Magiatis P (2012). Direct measurement of oleocanthal and oleacein levels in olive oil by quantitative 1H NMR. Establishment of a new index for the characterization of extra virgin olive oils. Journal of Agricultural and Food Chemistry 60(47):11696-11703. https://doi.org/10.1021/jf3032765

Khalatbary AR (2013). Olive oil phenols and neuroprotection. Nutritional Neuroscience 16(6):243-249. https://doi.org/10.1179/1476830513Y.0000000052

Kingston DG (2011). Modern natural products drug discovery and its relevance to biodiversity conservation. Journal of Natural Products 74(3):496-511. https://doi.org/10.1021/np100550t

Korkina LG (2007). Phenylpropanoids as naturally occurring antioxidants: from plant defense to human health. Cellular and Molecular Biology 53(1):15-25.

Kumral A, Korukluoglu M, Romero C, de Castro A, Ruiz-Barba JL, Brenes M (2013). Phenolic inhibitors involved in the natural fermentation of Gemlik cultivar black olives. European Food Research and Technology 236(1):101-107. https://doi.org/10.1007/s00217-012-1859-8

Lee JH, Lee JY, Kang HS, Jeong CH, Moon H, Whang WK, Sim SS (2006). The effect of acteoside on histamine release and arachidonic acid release in RBL-2H3 mast cells. Archives of Pharmacological Research 29(6):508. https://doi.org/10.1007/BF02969425

Lenoir L, Rossary A, Joubert-Zakeyh J, Vergnaud-Gauduchon J, Farges MC, Fraisse D, Felgines C (2011). Lemon verbena infusion consumption attenuates oxidative stress in dextran sulfate sodium-induced colitis in the rat. Digestive Diseases and Sciences 56(12):3534-3545. https://doi.org/10.1007/s10620-011-1784-x

Lin Y, Shi R, Wang X, Shen HM (2008). Luteolin, a flavonoid with potential for cancer prevention and therapy. Current Cancer Drug Targets 8(7):634-646. https://doi.org/10.2174/156800908786241050

López-Fernández O, Domínguez R, Pateiro M, Munekata P, Rocchetti G, Lorenzo JM (2020). Determination of polyphenols using liquid chromatography-tandem mass spectrometry technique (LC-MS/MS): A review. Antioxidants 9(6):479. https://doi.org/10.3390/antiox9060479

Mazza G, Miniati E (1993). Anthocyanins in fruits, vegetables and grains Boca Raton, FL: CRC Press, pp 64-67.

Melliou E, Zweigenbaum JA, Mitchell AE (2015). Ultrahigh-pressure liquid chromatography triple-quadrupole tandem mass spectrometry quantitation of polyphenols and secoiridoids in California-style black ripe olives and dry salt-cured olives. Journal of Agricultural and Food Chemistry 63(9):2400-2405. https://doi.org/10.1021/jf506367e

Mitsopoulos G, Papageorgiou V, Komaitis M, Hagidimitriou M (2016). Phenolic profile of leaves and drupes of ten olive varieties. Notulae Botanicae Horti Agrobotanici Cluj-Napoca 44(1):162-166. https://doi.org/10.15835/nbha44110382

Nassiri-Asl M, Mortazavi SR, Samiee-Rad F, Zangivand AA, Safdari F, Saroukhani S, Abbasi E (2010). The effects of rutin on the development of pentylenetetrazole kindling and memory retrieval in rats. Epilepsy & Behavior 18(1-2):50-53. https://doi.org/10.1016/j.yebeh.2010.03.005

Parkinson L, Cicerale S (2016). The health benefiting mechanisms of virgin olive oil phenolic compounds. Molecules 21(12):1734. https://doi.org/10.3390/molecules21121734

Qiao H, Zhang X, Zhu C, Dong L, Wang L, Zhang X, Cao X (2012). Luteolin downregulates TLR4, TLR5, NF-κB and p-p38MAPK expression, upregulates the p-ERK expression, and protects rat brains against focal ischemia. Brain Research 1448:71-81. https://doi.org/10.1016/j.brainres.2012.02.003

Richetti SK, Blank M, Capiotti KM, Piato AL, Bogo MR, Vianna MR, Bonan CD (2011). Quercetin and rutin prevent scopolamine-induced memory impairment in zebrafish. Behavioral Brain Research 217(1):10-15. https://doi.org/10.1016/j.bbr.2010.09.027

Rigacci S, Stefani M (2016). Nutraceutical properties of olive oil polyphenols. An itinerary from cultured cells through animal models to humans. International Journal of Molecular Sciences 17(6):843. https://doi.org/10.3390/ijms17060843

Robles-Almazan M, Pulido-Moran M, Moreno-Fernandez J, Ramirez-Tortosa C, Rodriguez-Garcia C, Quiles JL, Ramirez-Tortosa M (2018). Hydroxytyrosol: Bioavailability, toxicity, and clinical applications. Food Research International 105:654-667. https://doi.org/10.1016/j.foodres.2017.11.053

Romani A, Mulinacci N, Pinelli P, Vincieri FF, Cimato A (1999). Polyphenolic content in five Tuscany cultivars of Olea europaea L. Journal of Agricultural and Food Chemistry 47:964–967. https://doi.org/10.1021/jf980264t

Romero C, Brenes M, Garcia P, Garrido A (2002). Hydroxytyrosol 4-β-D- glucoside, an important phenolic compound in olive fruits and derived products. Journal of Agricultural and Food Chemistry 50:3835-3839. https://doi.org/10.1021/jf011485t

Romero C, Medina E, Mateo MA, Brenes M (2017). Quantification of bioactive compounds in Picual and Arbequina olive leaves and fruit. Journal of the Science of Food and Agriculture 97(6):1725-1732. https://doi.org/10.1002/jsfa.7920

Ryan D, Robards K (1998). Phenolic compounds in olives. Analyst 123:31-44.

Sahan Y, Cansev A, Gulen H (2013). Effect of processing techniques on antioxidative enzyme activities, antioxidant capacity, phenolic compounds, and fatty acids of table olives. Food Science and Biotechnology 22(3):613-620. https://doi.org/10.1007/s10068-013-0122-9

Salas-Salvadó J, Bulló M, Estruch R, Ros E, Covas MI, Ibarrola-Jurado N, Romaguera D (2014). Prevention of diabetes with Mediterranean diets: a subgroup analysis of a randomized trial. Annals of internal medicine 160(1):1-10. https://doi.org/10.7326/M13-1725

Salis C, Papageorgiou L, Papakonstantinou E, Hagidimitriou M, Vlachakis D (2020). Olive Oil Polyphenols in Neurodegenerative Pathologies. In: Vlamos P (Ed). GeNeDis 2018. Advances in Experimental Medicine and Biology. Vol 1195. Springer, Cham. https://doi.org/10.1007/978-3-030-32633-3_12

Segura-Carretero A, Carrasco-Pancorbo A, Bendini A, Cerretani L, Fernández-Gutiérrez A (2010). Analytical determination of polyphenols in olive oil. In: Olives and olive oil in health and disease prevention. Academic Press, pp 509-523. https://doi.org/10.1016/B978-0-12-374420-3.00056-5

Selli S, Kelebek H, Kesen S, Sonmezdag AS (2018). GC‐MS olfactometric and LC‐DAD‐ESI‐MS/MS characterization of key odorants and phenolic compounds in black dry‐salted olives. Journal of the Science of Food and Agriculture 98(11):4104-4111. https://doi.org/10.1002/jsfa.8927

Servili M, Selvaggini R, Esposto S, Taticchi A, Montedoro G, Morozzi G (2004). Health and sensory properties of virgin olive oil hydrophilic phenols: agronomic and technological aspects of production that affect their occurrence in the oil. Journal of Chromatography A 1054(1-2):113-127. https://doi.org/10.1016/j.chroma.2004.08.070

Siliani S, Mattei A, Innocenti LB, Zanoni B (2006). Bitter taste and phenolic compounds in extra virgin olive oil: an empirical relationship. Journal of Food Quality 29(4):431-441. https://doi.org/10.1111/j.1745-4557.2006.00084.x

Soler-Rivas C, Espın JC, Wichers HJ (2000). Oleuropein and related compounds. Journal of the Science of Food and Agriculture 80:1013-1023. https://doi.org/10.1002/(SICI)1097-0010(20000515)80:7<1013::AID-JSFA571>3.0.CO;2-C

Theoharides TC, Stewart JM, Hatziagelaki E (2015). Brain “fog”, inflammation and obesity: key aspects of neuropsychiatric disorders improved by luteolin. Frontiers in Neuroscience 9:225. https://doi.org/10.3389/fnins.2015.00225

Tomé-Carneiro J, Crespo MC, Iglesias-Gutierrez E, Martín R, Gil-Zamorano J, Tomas-Zapico C, Herrera E (2016). Hydroxytyrosol supplementation modulates the expression of miRNAs in rodents and in humans. The Journal of Nutritional Biochemistry 34:146-155. https://doi.org/10.1016/j.jnutbio.2016.05.009

Valenzuela R, Echeverria F, Ortiz M, Rincón-Cervera MÁ, Espinosa A, Hernandez-Rodas MC, Videla LA (2017). Hydroxytyrosol prevents reduction in liver activity of Δ-5 and Δ-6 desaturases, oxidative stress, and depletion in long chain polyunsaturated fatty acid content in different tissues of high-fat diet fed mice. Lipids in Health and Disease 16(1):64. https://doi.org/10.1186/s12944-017-0450-5

Vasto S, Barera A, Rizzo C, Di Carlo M, Caruso C, Panotopoulos G (2014). Mediterranean diet and longevity: an example of nutraceuticals? Current Vascular Pharmacology 12(5):735-738.

Vinha AF, Ferreres F, Silva BM, Valentao P, Gonçalves A, Pereira JA, Andrade PB (2005). Phenolic profiles of Portuguese olive fruits (Olea europaea L.): Influences of cultivar and geographical origin. Food Chemistry 89(4):561-568. https://doi.org/10.1016/j.foodchem.2004.03.012

Visioli F, Poli A, Gall C (2002). Antioxidant and other biological activities of phenols from olives and olive oil. Medicinal Research Reviews 22(1):65-75. https://doi.org/10.1002/med.1028

Zoidou E, Melliou E, Gikas E, Tsarbopoulos A, Magiatis P, Skaltsounis AL (2010). Identification of Throuba Thassos, a traditional Greek table olive variety, as a nutritional rich source of oleuropein. Journal of Agricultural and Food Chemistry 58(1):46-50. https://doi.org/10.1021/jf903405e

Published
2021-06-24
How to Cite
SALIS, C., PAPADAKIS, I. E., & HAGIDIMITRIOU, M. (2021). Identification and quantification of phenolic compounds in fresh and processed table olives of cv. ‘Kalamata’. Notulae Botanicae Horti Agrobotanici Cluj-Napoca, 49(2), 12394. https://doi.org/10.15835/nbha49212394
Section
Research Articles
CITATION
DOI: 10.15835/nbha49212394