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Antioxidants antioxidants Article Composition and Antioxidant Properties of Spanish Extra Virgin Olive Oil Regarding Cultivar, Harvest Year and Crop Stage Thays Helena Borges 1, Adriana Serna 2, Luis Carlos López 3 , Luis Lara 1, Rosa Nieto 1 and Isabel Seiquer 1,* 1 Departamento de Fisiología y Bioquímica de la Nutrición Animal, Estación Experimental del Zaidín, Consejo Superior de Investigaciones Científicas (CSIC), Camino del Jueves, Armilla, 18100 Granada, Spain 2 Policlínica de Especialidades Médicas. Federico Medrano 620, San Francisco del Rincón, Guanajuato 36300, Mexico; 3 Instituto de Biotecnología, Centro de Investigación Biomédica, Universidad de Granada, Avda. del Conocimiento, 18016 Granada, Spain * Correspondence: [email protected]; Tel.: +34-958-572-757; Fax: +34-958-572-753 Received: 25 June 2019; Accepted: 7 July 2019; Published: 11 July 2019 Abstract: The health benefits of extra virgin olive oil (EVOO) are related to its chemical composition and the presence of bioactive compounds with antioxidant properties. The aim of this study was to evaluate antioxidant compounds (pigments, coenzyme Q10 (CoQ10) and phenolic compounds) and antioxidant properties of EVOO from the same region comparing different cultivars (Hojiblanca and Arbequina), harvest year and crop stage. Antioxidant properties of oils were studied before and after a gastrointestinal digestion process, by in vitro assays (DPPH, ABTS and FRAP) and antioxidant markers in Caco-2 cells (reactive oxygen species production). The content of bioactive compounds measured was significantly affected by cultivar and harvest year (except for carotenoids) and by the crop stage (except for coenzyme Q10). Higher amounts of coenzyme Q10 were observed in Hojiblanca than in Arbequina EVOO. Total phenol content and antioxidant properties were also different depending on cultivar and harvest year and the in vitro digestion process strongly improved antioxidant marker values. Antioxidant potential in bioaccessible fractions was mainly related to the content of coenzyme Q10 and phenolic compounds in EVOO. Chemometric analysis showed that the oils were clearly classified by cultivars, harvest and crop stage, according to the chemical composition and antioxidant activity analyzed in the present study. Keywords: extra virgin olive oil; Hojiblanca; Arbequina; antioxidant properties; polyphenols; chemometric analysis 1. Introduction The health benefits of extra virgin olive oil (EVOO) are significantly attributed to its high antioxidant potential, which, in turn, is deeply linked to its chemical composition [1]. Some of the bioactive compounds with antioxidant activity identified in EVOO are carotenoids, coenzymes and phenolic compounds, among others [2,3]. Multiple health benefits have been ascribed to phenolic compounds, such as prevention of cardiovascular disease; anti-inflamatory, antimicrobial and antiviral activities; and general protection against oxidative damage [4,5]. Antioxidants present in EVOO delay oxidative stress by inhibiting the formation or preventing the propagation of free radicals by several mechanisms; methods usually used to evaluate the antioxidant capacity are mainly focused on assessing the free radical scavenging ability, such as 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) or the ferric Antioxidants 2019, 8, 217; doi:10.3390/antiox8070217 www.mdpi.com/journal/antioxidants Antioxidants 2019, 8, 217 2 of 16 reducing antioxidant power (FRAP) and are commonly applied in chemical extracts of the oils [6]. These methods may be useful to determine the oil oxidative stability of the oil, but the biological effect of antioxidant compounds in vivo will depend on their bioavailability [7]. In this sense, it is accepted that the primary requisite for a bioactive compound to exert an antioxidant activity in vivo is to be bioaccessible, i.e., be released from the from matrix during the digestive process and, moreover, maintain its properties after the biotransformations caused by the gastrointestinal digestion [8]. The determination of antioxidant activity after in vitro digestion, considering all the transformations of the EVOO matrix, and consequently of its bioactive compounds has been investigated in previous works [6,8–11]. It is widely known that composition and antioxidant properties of EVOO may be affected by several agronomic factors, such as cultivar, fruit ripening stage and agroclimatic conditions [5,12,13]. The olive ripeness and the cultivar have been described as the most important factors affecting the EVOO phenolic profile [14,15], while organoleptic characteristic such flavour have been linked to geographic and climatic factors more than to cultivar or ripening stage [13,16]. Nevertheless, studies about how these aspects could affect the bioaccessible fraction of EVOO are still very scarce. In the present work, we aimed to evaluate some relevant aspects of chemical composition (pigments, coenzyme Q10 (CoQ10) and phenolic compounds) and the antioxidant potential of Spanish EVOO from the same geographic region, comparing different cultivars, harvest years and crop stages (early and late). As the content of bioactive compounds may also influence the oil colour, colour coordinates were also measured. The antioxidant activity was studied after and before an in vitro gastrointestinal digestion, and methods based on H-atom and single-electron transfer (DPPH, ABTS, FRAP) together with cell culture markers (generation of reactive oxygen species (ROS)) were applied. 2. Materials and Methods 2.1. Chemicals The chemicals used were all of high purity or analytical reagent grade. Bidistilled deionized water (Milli-Q purification system, Millipore, Bedford, MA, USA) was used. Ethanol and methanol were provided by VWR (Barcelona, Spain), sodium bicarbonate, acetate sodium, sodium carbonate, hydrochloric acid (37%), caffeic acid, hydrochloric acid, anhydrous sodium carbonate and potassium hexacyanoferrate (III) were acquired to Merck (Darmstad, Germany). Folin–Ciocalteau reagent, 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid (Trolox), DPPH, Pepsin, Pancreatin, bile salts, (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid) (HEPES) and tert-butylhydroperoxide (t-BOOH), the cell culture media, cell culture-grade chemicals, standards for individual phenolic compounds and. CoQ10 analysis were purchased to Sigma (Sigma-Aldrich, St, Louis, MO, USA). The ABTS was obtained from Amresco (Solon, USA). 2,4,6-Tri(2-pyridyl)-s-triazine (TPTZ) and iron (III) chloride for the ferric reducing power (FRAP) assay were from Fluka Chemicals (Fluka Chemicals, Madrid, Spain). 2.2. Samples EVOO from two cultivars (Arbequina and Hojiblanca) from the South of Spain (Estepa, Sevilla; latitude 30◦170N, longitude 4◦520W) were analyzed. The olives were harvested in two years (2014 and 2015) at two crop stages: early stage (September–October, stage 1) and late stage (November–December, stage 2). The oil was extracted within 24 hours under a two-phase extraction system. The samples (n = 3 from each stage and season) were directly donated by the producers from the same cooperative and sent to the Spanish National Research Council laboratories (CSIC, Granada, Spain) protected from light and high temperature until analysis. All the samples meet standards of quality established by the European Union regulation n◦ 2568/91 for EVOO The description of samples and the climatic conditions of seasons are presented in Table1. Antioxidants 2019, 8, 217 3 of 16 Table 1. Description of the extra virgin olive oil (EVOO) samples. Cultivar Year Stage Mean Temperature (◦C) Mean Rainfall (mm) Arbequina/Hojiblanca 2014 1 22.2 102.5 2 16.2 140.7 Arbequina/Hojiblanca 2015 1 20.6 125.5 2 16.2 45.2 Mean temperature and rainfall were supplied by the Spanish Meteoroly Agency, (Aemet, http://www.aemet.es), and corresponds to the province of Seville. 2.3. Determination of CoQ10 The analysis of Co Q10 was performed as described by Borges et al. [17]. Briefly, 1-propanol was mixed with oil, vortexed and centrifuged at 11,300 g, 5 min. The supernatant was diluted (1/500) in 1-propanol before the high-performance liquid chromatography (HPLC) injection. CoQ10 in the oil extract was determined by HPLC (reversed-phase high-performance liquid chromatography, Gilson, Middleton, WI, USA) with a C18 symmetry column (3.5 µm, 4.6 150 mm) (Waters Chromatography, × Barcelona, Spain) using methanol, ethanol, 2-propanol, glacial acetic acid (500:500:15:15) and 50 mM sodium acetate at a flow rate of 0.9 mL/min as a mobile phase. The electrochemical detector consisted of an ESA Coulochem III with the following setting: Guard cell (upstream of the injector) at +900 mV and the analytical cell at +350 mV. Reduced CoQ10 (ubiquinol) and oxidized CoQ10 (ubiquinone) could be determined by this method, although ubiquinol was not detected in our conditions of extraction and analysis. The CoQ10 concentration of the oxidized form was estimated comparing the peak areas with those of standard solutions; values of the calibration curve were reported previously [17]. The results were expressed in mg/L of sample. 2.4. Pigments (Chlorophylls and Carotenoids) and Colour Chlorophylls and carotenoids were determined according to Minguez-Mosquera et al. [18]. The samples of oil were dissolved with cyclohexane (1.5:5 w/v) and the absorbance was measured with a UV spectrophotometer (Pharmaspec UV 1700, Shimadzu, Kyoto, Japan). The chlorophyll and the carotenoid fractions were determined at 670 and 470 nm,
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