Singular Olive Oils from a Recently Discovered Spanish North-Western Cultivar: An Exhaustive 3-Year Study of Their Chemical Composition and In-Vitro Antidiabetic Potential

In this work, the quality and physicochemical parameters, phenolic composition, and antidiabetic potential of olive oils obtained from olives belonging to centenarian olive trees of the so-called 'Mansa de Figueiredo' cultivar were evaluated during three consecutive crop seasons (2017-2019). The oils produced during the three crop years were classified as extra virgin based on the quality-related indices, sensory analysis, and the genuineness-related parameters. In addition, LC-ESI-TOF MS was used to get a comprehensive characterisation of the phenolic fraction while LC-ESI-IT MS was applied for quantitation purposes. The content of phenolic compounds (ranging from 1837 to 2434 mg/kg) was significantly affected by the harvest year due to the environmental conditions and ripening index. Furthermore, although significant differences in the inhibitory effects against the alpha-glucosidase enzyme for the EVOOs extracted throughout the three successive years were detected, all the studied EVOOs exhibited a stronger inhibitor effect than that found for acarbose.Spanish Government RTI2018-098633-B-I00FEDER/Junta de Andalucia-Consejeria de Transformacion Economica, Industria, Conocimiento y Universidades P20_00263FQM-297 research group (Environmental, Biochemical and Nutritional Analytical Control) FEDER/Junta de AndaluciaConsejeria de Economia y Conocimiento B-AGR-416-UGR18Spanish Government FPU19/0070

Geographical Indication Labels in Moroccan Olive Oil Sector: Territorial Dimension and Characterization of Typicality: A Case Study of Meknès Region

Geographical indications (GIs) implementation is, nowadays, one of the most prominent differentiation strategies used in olive oil market. The proliferation of these labels, however, causes debate and controversy, in particular regarding their usefulness, effectiveness, and suitability of some protected areas to acquire them. This chapter discusses the use of GI labels in olive oil market, and proposes a four-stage methodological approach to examine the potential of Meknès region—a Moroccan olive growing area—to acquire a GI label. Based on this approach, Meknès region territorial dimensions were defined, the typicality of its olive oil was characterized, a general scheme for the GI recognition was proposed, and the adopted strategy to enhance the meaning of this label on domestic, national, and international markets was highlighted. The main findings of this study justify the suitability of Meknès region to protect its olive oil with a GI label

Fruit Phenolic and Triterpenic Composition of Progenies of Olea europaea subsp. cuspidata, an Interesting Phytochemical Source to Be Included in Olive Breeding Programs

Olea europaea subsp. cuspidata has a relatively low commercial value due to the low size and pulp to stone ratio of its drupes compared to commercial olive cultivars. Nevertheless, this subspecies could represent a valid source of useful traits for olive breeding. In the current work, the drupe metabolic composition (secoiridoids, flavonoids, simple phenols, triterpenic acids, etc.) of a progeny of 27 cuspidata genotypes coming from free pollination and their female parent was evaluated by applying a powerful LC-MS method. A total of 62 compounds were detected within the profiles; 60 of them were annotated and 27 quantified. From a quantitative point of view, the genotypes from the progeny of cuspidata showed quite different metabolic profiles to olive common cultivars (“Arbequina”, “Frantoio”, “Koroneiki” and “Picual”) used as controls. Cuspidata drupes were richer in terms of several bioactive compounds such as rutin, hydroxytyrosol glucoside, a few interesting secoiridoids and the compounds of m/z 421 and 363. The relationships among several secondary metabolites determined in the progeny inferred from the results of both PCA and crosscorrelation analysis were explained according to metabolic biosynthesis pathways in olive drupes. These outcomes underlined the potential of cuspidata genetic resources as a source of potentially interesting variability in olive breeding programs.FEDER/Junta de Andalucia-Consejeria de Transformacion Economica, Industria, Conocimiento y Universidades P20_00263FEDER/Junta de AndaluciaConsejeria de Economia y Conocimiento B-AGR-416-UGR18Andalusian Institute of Agricultural and Fisheries Research and Training (IFAPA) AVA2019.027European CommissionSpanish Government FPU19/0070

Storage Stability of Arauco Virgin Olive Oil: Evolution of Its Quality Parameters and Phenolic and Triterpenic Compounds under Different Conservation Conditions

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/plants12091826/s1This research was funded by Universidad Nacional de Cuyo (A102-SIIP-UNCuyo to R.P.M.), FEDER/Junta de Andalucia-Consejeria de Transformacion Economica, Industria, Conocimiento y Universidades, Proyecto P20_00263, and FEDER/Junta de Andalucia-Consejeria de Economia y Conocimiento, Proyecto B-AGR-416-UGR18. The authors appreciate the funding received from the Spanish Government (FPU19/00700) (I.S.-G.), UE-NextGenerationUE (R.P.M. and L.O.-G.), and AUIP (R.P.M.).The storage conditions are very critical to minimize hydrolytic and oxidative reactions of virgin olive oils (VOOs). These reactions are logically influenced by the composition of the VOO, so that each variety may have a specific behavior. The aim of this study was to evaluate changes in quality parameters and in the phenolic and triterpenic profile of Arauco VOOs, a unique local variety from Argentina, after storage under different conditions. The effects of exposure to light (darkness and light), temperature (24 and 40 ?), packaging material (polyethylene (PET) and dark glass), and headspace (air and N-2 atmosphere) were investigated for 76 days. A reduction in total phenolic compounds was observed after storage treatments, but all samples still complied with the EFSA health claim after the different handlings. Overall, the results revealed that the preservation of the oils in PET appears adequate, with improved stability when N-2 was used in the headspace, along with darkness and low temperature. The study of phenolic profiles showed that substances previously reported as possible markers of olive oil aging, such as hydroxytyrosol and an isomer of decarboxymethyl oleuropein aglycone, also have a similar behavior during the aging of Arauco variety oil. Interestingly, some evidence was found that another oleuropein-derived compound (oleuropein aglycone isomer 3) could also be used as an aging marker.Universidad Nacional de Cuyo A102-SIIP-UNCuyoFEDER/Junta de Andalucia-Consejeria de Transformacion Economica, Industria, Conocimiento y Universidades P20_00263FEDER/Junta de Andalucia-Consejeria de Economia y Conocimiento B-AGR-416-UGR18Spanish Government FPU19/00700UE-NextGenerationUEAUI

Nutraceutical Potential of Phenolics from `Brava´ and `Mansa´ Extra-Virgin Olive Oils on the Inhibition of Enzymes Associated to Neurodegenerative Disorders in Comparison with Those of `Picual´ and `Cornicabra´

The increasing interest in theMediterranean diet is based on the protective effects against several diseases, including neurodegenerative disorders. Polyphenol-rich functional foods have been proposed to be unique supplementary and nutraceutical treatments for these disorders. Extra-virgin olive oils (EVOOs) obtained from 0Brava0 and 0Mansa0, varieties recently identified from Galicia (northwestern Spain), were selected for in vitro screening to evaluate their capacity to inhibit key enzymes involved in Alzheimer0s disease (AD) (acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) and 5-lipoxygenase (5-LOX)), major depressive disorder (MDD) and Parkinson0s disease (PD) (monoamine oxidases: hMAO-A and hMAO-B respectively). 0Brava0 oil exhibited the best inhibitory activity against all enzymes, when they are compared to 0Mansa0 oil: BuChE (IC50 = 245 ± 5 and 591 ± 23 mg.mL-1), 5-LOX (IC50 = 45 ± 7 and 106±14 mg.mL-1), hMAO-A (IC50 = 30 ± 1 and 72 ± 10 mg.mL-1) and hMAO-B (IC50 = 191 ± 8 and 208 ±14 mg.mL-1), respectively. The inhibitory capacity of the phenolic extracts could be associated with the content of secoiridoids, lignans and phenolic acids.This work received financial support from Programa de Cooperación Interreg V-A España—Portugal (POCTEP) 2014–2020 (projects Ref.: 0181_NANOEATERS_01_E and Ref: 0377_IBERPHENOL_6_E)

Exploratory analysis of human urine by LC–ESI-TOF MS after high intake of olive oil: understanding the metabolism of polyphenols

Olive oil polyphenols have important biological properties which closely depend on their bioavailability, therefore it is essential to understand how polyphenols are absorbed, metabolized and eliminated from the body. An analytical methodology based on rapid resolution liquid chromatography (RRLC) coupled to mass spectrometry detection with a time of flight analyzer (RRLC-ESI-TOF MS) was developed for the determination of the main olive oil phenolic compounds and their metabolites in human urine. Urine samples from ten healthy volunteers were collected before and 2, 4 and 6 h after the intake of 50 mL of extra-virgin olive oil. The proposed method includes liquid-liquid extraction with ethyl acetate that provides extraction recoveries of the phenolic compounds studied between 35 and 75% from spiked urine samples. Good repeatability was obtained, since the relative standard deviations (RSDs) of peak areas in the intra- and inter-day studies were 4.3 and 6.5%, respectively. Statistical studies allowed us to discriminate between the urine samples before and after the intake, and facilitated to find out the m/z values responsible of this discrimination. Based on the very accurate mass information and the isotopic pattern provided by TOF-MS analyzer, together with other available information, ten of these biomarkers and more than 50 metabolites, obtained through phase I and phase II biotransformation reactions, were tentatively identified. Additionally, kinetic studies of the metabolites identified as possible biomarkers were developed, obtaining maximal values in the first two hours for most compounds.The authors are very grateful to Ministry of Education and Science (FPU, AP2005-4356 and Project AGL 2008- 05108-613 CO3-03/ALI), and Junta de Andalucía (P07-AGR-02629 and P09-FQM-5469)

Unravelling the Distribution of Secondary Metabolites in Olea europaea L.: Exhaustive Characterization of Eight Olive-Tree Derived Matrices by Complementary Platforms

In order to understand the distribution of the main secondary metabolites found in Olea europaea L., eight different samples (olive leaf, stem, seed, fruit skin and pulp, as well as virgin olive oil, olive oil obtained from stoned and dehydrated fruits and olive seed oil) coming from a Picudo cv. olive tree were analyzed. All the experimental conditions were selected so as to assure the maximum coverage of the metabolome of the samples under study within a single run. The use of LC and GC with high resolution MS (through different ionization sources, ESI and APCI) and the annotation strategies within MetaboScape 3.0 software allowed the identification of around 150 compounds in the profiles, showing great complementarity between the evaluated methodologies. The identified metabolites belonged to different chemical classes: triterpenic acids and dialcohols, tocopherols, sterols, free fatty acids, and several sub-types of phenolic compounds. The suitability of each platform and polarity (negative and positive) to determine each family of metabolites was evaluated in-depth, finding, for instance, that LC-ESI-MS (+) was the most efficient choice to ionize phenolic acids, secoiridoids, flavonoids and lignans and LC-APCI-MS was very appropriate for pentacyclic triterpenic acids (MS (-)) and sterols and tocopherols (MS (+)). Afterwards, a semi-quantitative comparison of the selected matrices was carried out, establishing their typical features (e.g., fruit skin was pointed out as the matrix with the highest relative amounts of phenolic acids, triterpenic compounds and hydroxylated fatty acids, and seed oil was distinctive for its high relative levels of acetoxypinoresinol and tocopherols)

Separation and Determination of Some of the Main Cholesterol-Related Compounds in Blood by Gas Chromatography-Mass Spectrometry (Selected Ion Monitoring Mode)

Oxysterols are metabolites produced in the first step of cholesterol metabolism, which is related to neurodegenerative disorder. They can be detected by testing blood, plasma, serum, or cerebrospinal fluid. In this study, some cholesterol precursors and oxysterols were determined by gas chromatography coupled to mass spectrometry. The selected cholesterol-related compounds were desmosterol, lathosterol, lanosterol, 7 -hydroxycholesterol, 7 -hydroxycholesterol, 24(S)-hydroxycholesterol, 25-hydroxycholesterol, 7-ketocholesterol, and 27-hydroxycholesterol. A powerful method was developed and validated considering various analytical parameters, such as linearity index, detection and quantification limits, selectivity and matrix effect, precision (repeatability), and trueness (recovery factor) for each cholesterol-related compound. 7 -hydroxycholesterol, 7 -hydroxycholesterol, and desmosterol exhibited the lowest detection and quantification limits, with 0.01 and 0.03 g/mL, respectively, in the three cases. 7-ketocholesterol and lathosterol showed matrix effect percentages between 95.5% and 104.8%, respectively (demonstrating a negligible matrix effect), and very satisfactory repeatability values (i.e., overall performance of the method). Next, the method was applied to the analysis of a very interesting selection of mouse plasma samples (9 plasma extracts of non-transgenic and transgenic mice that had been fed different diets). Although the number of samples was limited, the current study led to some biologically relevant conclusions regarding brain cholesterol metabolism.The authors are grateful for the interesting collaboration with the biotechnology-based company Neuron Bio. The research project was funded by CEI BioTic/University of Granad

Comparative Extraction of Phenolic Compounds from Olive Leaves Using a Sonotrode and an Ultrasonic Bath and the Evaluation of Both Antioxidant and Antimicrobial Activity

This study is part of the project SHEALTHY that has received funding from European Union's Horizon 2020 Research and Innovation Programme under grant agreement No 817936. This study was also supported by project RTI2018-099835-A-I00 financed by MCIN/AEI/10.13039/5011000 11033/FEDER "Una manera de hacer Europa".A sonotrode ultrasound-assisted extraction of phenolic compounds from olive leaves has been developed using a Box-Behnken design to optimize the effects of solvent composition and ultrasound parameters. The determination of single phenolic compounds was performed by HPLC-MS and the highest recovery in total compounds, oleuropein and hydroxytyrosol was achieved using EtOH/H2O (55:45, v/v), 8 min and 100% of amplitude. The optimal conditions were applied on leaves from seven olive cultivars grown under the same conditions and the results were compared with those found by using a conventional ultrasonic bath, obtaining no statistical differences. Moreover, antioxidant activity by FRAP, DPPH and ABTS in these olive leaf extracts was evaluated and they exhibited a significant correlation with oleuropein and total phenolic content. All cultivars of olive leaf extracts were found to be active against S. aureus and methicillin-resistant S. aureus with minimum bactericidal concentration (MBC) values) that ranged from 5.5 to 22.5 mg mL(-1). No extracts showed antimicrobial activity against C. albicans. The percentages of mycelium reduction in B. cinerea ranged from 2.2 and 18.1%. Therefore, sonotrode could be considered as an efficient and fast extraction technique that could be easily scaled-up at industrial level, thus allowing for olive leaves to be revalorized.European Union's Horizon 2020 Research and Innovation Programme 817936MCIN/AEI/FEDER "Una manera de hacer Europa" RTI2018-099835-A-I0