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

The roots of olive cultivars differing in tolerance to Verticillium dahliae show quantitative differences in phenolic and triterpenic profiles

This work was supported by the grants PID2019-106283RB-I00, BES-2017-081269 and FPU19/00700 of the Spanish Ministerio de Ciencia, Innovacion y Universidades (MICIU)/Agencia Estatal de Investigacion (AEI), and the grant RYC2021-032996-I funded by MCIN/AEI/10.13039/501100011033 and by "European Union NextGenerationEU/PRTR". This research was partially funded by FEDER/Junta de Andalucia-Consejeria de Conocimiento, Investigacion y Universidad, Junta de Andalucia Transformacion Economica, Industria, Conocimiento y Universidades, Proyecto P20_00263; and FEDER/Junta de Andalucia-Consejeria de Economia y Conocimiento, Proyecto B-AGR-416-UGR18.Verticillium wilt of olive (VWO), caused by Verticillium dahliae, is a major concern in many olive- growing countries. An efficient VWO control measure is the use of tolerant/resistant cultivars. Low information is available about olive secondary metabolites and its relationship with VWO tolerance. In this study, a comprehensive metabolic profiling of the roots of six olive cultivars differing in their level of tolerance/susceptibility to VWO was addressed. Potential changes in the metabolite profiles due to the presence of the pathogen were also assessed. A strong relationship between the quantitative basal composition of the root secondary metabolic profile and VWO tolerance/susceptibility of olive varieties was found. Tolerant cultivars showed higher content of secoiridoids, while the susceptible ones presented greater amounts of verbascoside and methoxypinoresinol glucoside. The presence of V. dahliae only caused few significant variations mostly restricted to the earliest times after inoculation. Thus, a rapid activation of biochemical- based root defense mechanisms was observed.Spanish Ministerio de Ciencia, Innovacion y Universidades (MICIU)/Agencia Estatal de Investigacion (AEI) PID2019-106283RB-I00, BES-2017-081269, FPU19/00700MCIN/AEI RYC2021-032996-IEuropean Union NextGenerationEU/PRTR RYC2021-032996-IFEDER/Junta de Andalucia-Consejeria de Conocimiento, Investigacion y UniversidadJunta de Andalucia Transformacion Economica, Industria, Conocimiento y Universidades P20_00263FEDER/Junta de Andalucia-Consejeria de Economia y Conocimiento B-AGR-416-UGR1

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

Nano- and rapid resolution liquid chromatography-electrospray ionization-time of flight mass spectrometry to identify and quantify phenolic compounds in olive oil

The applicability of nano-liquid chromatography coupled to electrospray ionization-time of flight-mass spectrometry (nanoLC-ESI-TOF MS) for the analysis of phenolic compounds in olive oil was studied and compared with a HPLC method. After the injection, the compounds were focused on a short capillary trapping column (100 μm i.d., effective length 20 mm, 5 μm particle size) and then nanoLC analysis was carried out in a fused silica capillary column (75 μm i.d., effective length 10 cm, 3 μm particle size) packed with C18 stationary phase. The mobile phase was a mixture of water + 0.5% acetic acid and acetonitrile eluting at 300 nL/min in a gradient mode. Phenolic compounds from different families were identified and quantified. The quality parameters of the nanoLC method (linearity, limits of detection and quantification, repeatability) were evaluated and compare to those obtained with HPLC. The new methodology presents better sensitivity (reaching LOD values below 1 ppb) with less consumption of mobile phases, but worse repeatability, especially inter-day repeatability, doing more difficult to get highly accurate quantification. The results described in this paper open up the application fields of this technique to cover a larger variety of compounds and its advantages will make it especially useful for the analysis of samples containing low concentration of phenolic compounds, as for instance, in biological samples.Ministry of Education and Science (FPU, AP2005- 4356 and Proyect AGL 2008-05108-CO3-03/ALI), and Junta de Andalucía (Proyect P07-AGR-02619)

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)

Uptake and metabolism of olive oil polyphenols in human breast cancer cells using nano-liquid chromatography coupled to electrospray ionization–time of flight-mass spectrometry

Polyphenols from extra virgin olive oil (EVOO), a main component of the Mediterranean diet, have demonstrated repeatedly anti-tumor activity in several in vitro and in vivo studies. However, little is known about the efficiency of the absorption process and metabolic conversion of these compounds at cellular level. In this study, a nano liquid chromatography–electrospray ionization–time of flight mass spectrometry (nanoLC–ESI–TOF MS) method was developed to study the cellular uptake and metabolism of olive oil phenols in JIMT-1 human breast cancer cells. After incubation for different time periods with EVOO-derived phenolic extracts, culture media, cytosolic fraction and solid particles fraction were separated and analyzed. Most of the free phenols, mainly hydroxytyrosol, its secoiridoid derivatives, and the flavonoid luteolin, disappeared in the culture media in different ways and at different times. Besides, several metabolites were detected in the culture media, fact that may indicate absorption and intracellular metabolism followed by rapid cellular export. Low intracellular accumulation was observed with only traces of some compounds detected in the cytosolic and solid particles fractions. Methylated conjugates were the major metabolites detected, suggesting a catalytic action of catechol-O-methyl transferase (COMT) in cancer cells.The authors are very grateful to Ministry of Education and Science (FPU, AP2005-4356) and Junta de Andalucia (project P09-FQM-5469, project P07-AGR-02619 and AGL 2008-05108- CO3-03/ALI). Besides, this work was supported in part by Instituto de Salud Carlos III (Ministerio de Sanidad y Consumo, Fondo de Investigación Sanitaria – FIS, Spain, Grants CP05-00090, PI06-0778 and RD06-0020-0028)

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)