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Preliminary Investigation of Different Drying Systems to Preserve Hydroxytyrosol and Its Derivatives in Olive Oil Filter Cake Pressurized Liquid Extracts

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Preliminary Investigation of Different Drying Systems to Preserve Hydroxytyrosol and Its Derivatives in Olive Oil Filter Cake Pressurized Liquid Extracts foods Article Preliminary Investigation of Different Drying Systems to Preserve Hydroxytyrosol and Its Derivatives in Olive Oil Filter Cake Pressurized Liquid Extracts Lucía López-Salas 1, Inés Cea 2,3, Isabel Borrás-Linares 4,*, Tatiana Emanuelli 5 , Paz Robert 2, Antonio Segura-Carretero 4,6,† and Jesús Lozano-Sánchez 1,4,† 1 Department of Food Science and Nutrition, University of Granada, Campus Universitario S/N, 18071 Granada, Spain; [email protected] (L.L.-S.); [email protected] (J.L.-S.) 2 Departamento de Ciencia de los Alimentos y Tecnología Química, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Casilla 133, Santiago 8380494, Chile; [email protected] (I.C.); [email protected] (P.R.) 3 Center for Systems Biotechnology, Fraunhofer Chile Research, Av. Del Cóndor 844 Floor 3, Santiago 8580704, Chile 4 Functional Food Research and Development Centre (CIDAF), Health Sciencie Technological Park, Avda. Del Conocimiento S/N, 18016 Granada, Spain; [email protected] 5 Department of Food Technology and Science, Center of Rural Sciences, Federal University of Santa Maria, Camobi, Santa Maria 97105-900, RS, Brazil; [email protected] 6 Citation: López-Salas, L.; Cea, I.; Department of Analytical Chemistry, Faculty of Sciences, University of Granada, 18071 Granada, Spain * Correspondence: [email protected]; Tel.: +34-9586-37083 Borrás-Linares, I.; Emanuelli, T.; † These authors are joint senior authors on this work. Robert, P.; Segura-Carretero, A.; Lozano-Sánchez, J. Preliminary Investigation of Different Drying Abstract: Phenolic compounds present in extra virgin olive oil (EVOO) could be retained in its Systems to Preserve Hydroxytyrosol byproducts during processing. Among them, hydroxytyrosol and its derivatives deserve special and Its Derivatives in Olive Oil Filter attention due to their health benefits recognized by The European Food Safety Authority (EFSA). Cake Pressurized Liquid Extracts. In the present research, the presence of these compounds in the filter cake byproduct was studied Foods 2021, 10, 1407. https:// by combining pressurized liquid extraction (PLE) and high-performance liquid chromatography doi.org/10.3390/foods10061407 coupled to time-of-flight mass spectrometry (HPLC-TOF-MS). The applied optimum extraction parameters were 1500 psi, 120 ◦C and aqueous ethanol (50:50, v/v). The influence of different drying Academic Editors: Cosima methods (vacuum-, freeze- and spray-drying) in the recovery of phenolic compounds was also Damiana Calvano, evaluated. A total of 16 compounds from EVOO were identified in the extracts, 3 of them being Antonia Tamborrino and hydroxytyrosol-related compounds, 6 substances of oleoside and elenolic acid derivatives, together Theodoros Varzakas with 6 secoiridoids and 1 lignan. The results highlighted the great number of phenolic compounds recovered from filter cake with these techniques, being even higher than the reported content in Received: 26 April 2021 Accepted: 17 June 2021 EVOO and other byproducts. The combination of PLE and freeze-drying resulted in being the best Published: 18 June 2021 procedure for the recovery of phenolic compounds from filter cake byproduct. Publisher’s Note: MDPI stays neutral Keywords: olive oil byproducts; hydroxytyrosol; PLE; freeze drying; spray drying; HPLC-MS; with regard to jurisdictional claims in bioactive compounds published maps and institutional affil- iations. 1. Introduction The Mediterranean diet is characterized by high ingestion of non-ultra-processed nat- Copyright: © 2021 by the authors. ural food products such as legumes, fruits, vegetables, cereals, nuts and mainly extra virgin Licensee MDPI, Basel, Switzerland. olive oil (EVOO). This dietary pattern has been related to health benefits and protective This article is an open access article properties against various pathologies, such as several types of cancer, neurodegenerative distributed under the terms and and cardiovascular diseases [1–9]. Its distinguishing features with respect to other dietary conditions of the Creative Commons regimes are important from the nutritional and biological point of view: principally, the Attribution (CC BY) license (https:// use of olive oil and the consumption of fruits and vegetables, which are almost absent in creativecommons.org/licenses/by/ many other diets, such as northern Europeans [10]. 4.0/). Foods 2021, 10, 1407. https://doi.org/10.3390/foods10061407 https://www.mdpi.com/journal/foods Foods 2021, 10, 1407 2 of 12 From all the foods that characterized the Mediterranean diet, EVOO should be high- lighted; it is a highly valuable and appreciated product around the world for its beneficial health effects related to its chemical composition. The major compounds in EVOO are triacylglycerols, along with a minor fraction composed of many compounds in very low amounts (around 2% by weight of the oil). These minor substances are mainly tocopherols, pigments, volatile and phenolic compounds [11,12]. In recent years, these phenolic com- pounds have acquired great importance for their beneficial health properties, as antioxidant, anticancer, estrogenic, antidiabetic, antihypertensive, antithrombotic or anti-inflammatory capacities, among others effects [13–17]. Thus, phenolic compounds naturally present in EVOO have aroused great interest in the scientific world since the European Food Safety Authority (EFSA) recognized their beneficial antioxidant effects for the health at the minimum dose of 5 mg in 20 g of olive oil [18–20]. This health potential is associated with its protection against oxidative damage of LDL particles responsible for the transport of lipid molecules [18]. Hydroxytyrosol and its derivatives are considered the most important phenolic compounds present in EVOO due to their strong preventive effects exerted against many pathological processes. In fact, the EFSA authorized the health claim “contribute to the protection of blood lipids from oxidative stress” for EVOO, providing that its content is at least 250 mg/kg of these phenolic compounds. Most of the Mediterranean countries (especially Spain, Italy and Morocco) produce almost all of the world’s olive oil. In this industrial processing, large quantities of wastes are generated in different steps over the production [1,21]. Industrial processing plants provided with a three-phase decanter generate two types of byproducts, olive-mill wastew- ater (OMWW or alpechin) and pomace (orujo, solid waste) [22,23]. On the other hand, the two-phase decanter plants generate alperujo as the main byproduct, which is made up of a combination of solid and liquid wastes (orujo and alpechin)) [4,23]. Neverthe- less, other byproducts generated during EVOO production are liquid wastes and cakes, which are solid and liquid wastes from EVOO storage and filtering, apart from twigs and leaves [12,23]. Additionally, in the EVOO industrial processing, a partition of phenolic compounds present in the fruit between the EVOO and the generated byproducts occurs, leading to a transfer of these compounds from the EVOO to the olive oil wastes. In this sense, filter cakes are generated in large amounts in the final step of cloudy oil filtration. The main objective of the filtration process is to remove humidity and suspended solids of EVOO in order to obtain good quality oil for consumer acceptance, as well as to improve oil stability [24]. The loss of water leads to a decrease in polar compounds content in EVOO, including phenolic compounds. This fact originates filter cakes enriched in these compounds of interest with much potentials, such as hydroxytyrosol and derivatives [11]. Therefore, these byproducts could be used as a source of bioactive compounds for valued applications, reducing the economic and environmental impact of the waste treatment in the industry, enabling a more sustainable EVOO production inside a circular economy approach. In this line, the main objective of this research was to explore the potential combina- tion of an advanced extraction technique (pressurized liquid extraction, PLE) coupled to vacuum-, freeze- and spray-drying systems to obtain the best innovative process to recover hydroxytyrosol and its antioxidant derivatives from filter cake generated during EVOO production. The above-mentioned techniques were complemented by a deep chemical characterization of the extracted bioactive compounds carried out by high-performance liq- uid chromatography coupled with time-of-flight mass spectrometry (HPLC-ESI-TOF-MS). According to our knowledge, this is the first time that a detailed quantitative characteriza- tion of individual phenolic compounds recovered from a filter cake by the combination of PLE with different drying alternatives was evaluated. Foods 2021, 10, 1407 3 of 12 2. Materials and Methods 2.1. Reagents The chemicals employed during the development of this research were of analytical grade reagent. Milli-Q water for PLE and mobile phase preparation was obtained with a Millipore system (Bedford, MA, USA). Ethanol was provided by VWR Chemicals (Radnor, PA, USA), while Fisher Chemicals (Waltham, MA, USA) supplied cellulose filters and sand for PLE experiments. The mobile phase composition was obtained with acetic acid supplied by Sigma–Aldrich (Steinheim, Germany) and LC-MS-grade acetonitrile from Fisher Chemi- cals (Waltham, MA, USA). The commercial standards for quantitation purposes (quinic acid, hydroxytyrosol, pinoresinol, and oleuropein) were acquired from Sigma–Aldrich (St. Louis, MO, USA), Arbo Nova (Turku, Finland) and Extrasynthese (Lyon, France). 2.2.
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