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p-Coumaroyl-6́-secologanoside (comselogoside) is a secoiridoid identified in large amounts in olive fruits, although no studies in vitro or in vivo of comselogoside have been reported. This work focuses on the recovery and purification of this compound from olive mill waste (alperujo). The successive isolation on Amberlite XAD-16 and Sephadex LH-20 resins, allowed a comselogoside extract with 80-85% of purity. A photoisomerization of the vinyl-double bond in the p-coumaroyl moiety occurred when the extract was exposed to ultraviolet radiation and a mixture of the trans and cis-isomers was obtained. Both isomers were characterized using NMR, mass spectroscopy, and UV spectrometry. The J (coupling constant) of the protons on the C7 and C8 on the unsaturated chain were found to be the difference between cis (12.8 Hz) and trans- (15.9 Hz) comselogoside. Cis-isomer exhibited lower radical-scavenging activity than trans, although a synergistic effect occurred when the cis-isomer was supplement by the trans-isomer.

The pectin from the cell walls of olive waste (alperujo) and apple, orange and strawberry fruits was extracted using choline chloride (ChCl) and the yield and chemical and structural compositions were compared to pectin extracted using citric acid (CA) and ammonium oxalate/oxalic acid (AOOA). According to the results, the alperujo pectin extracted using ChCl from alcohol-insoluble residue (AIR) showed a higher yield (2.20–2.88% on the basis of dry weight of AIR) than using CA (0.65–1.22%) but lower than using AOOA (3.92–5.42%). For fruit pectin, the highest yield was obtained using CA (8.81–16%), followed by AOOA (5.4–6.63%), although for apple pectin, ChCl gave a similar yield (5.36%) to AOOA. The uronic acid contents in all ChCl pectins (45.9–70.6% dry basis AIR) were higher or similar to that of the other extracting agents (30.6–65.2%), although a lower level of neutral sugar side chains was detected, with a lower degree of branching and degree of methylation. The NMR and FT-IR spectroscopy of the pectin isolated using ChCl confirmed its slightly different structural composition with respect to CA and AOOA pectin. Therefore, depending on the source material and functionality, pectin isolated using ChCl could be an acid-free alternative to pectin production.

The olive oil sector is continuously evolving in order to improve the quality of olive oil and its by-products. In fact, the trend is to use increasingly greener olives to improve quality by decreasing the extraction yield, thus obtaining a higher content of antioxidant phenolics. The application of a cold-pressing system to the olive before the extraction of oil was tested with three varieties: picual at three different stages of maturity and arbequina and hojiblanca at early stages of maturity. The Abencor system was used for the extraction of virgin olive oil and its by-products. For the quantification of phenols and total sugars for all phases, organic solvent extractions and colorimetric measurements and high-performance liquid chromatography (HPLC) with a UV detector were used. The results show that the new treatment significantly improved the amount of oil extracted by between 1 and 2% and even increased its concentration of total phenols by up to 33%. Regarding the by-products, the concentrations of the main phenols, such as hydroxytyrosol, increased by almost 50%, as did the glycoside. The treatment also facilitated the separation of phases in by-products and improved the phenolic profile, although not in terms of total phenols, but individual phenols with higher antioxidant activity were obtained.

The pomace olive oil sector needs to improve its use of the main olive oil by-product, called alperujo, which is currently used mainly for combustion after extraction of pomace oil, with all the problems this process entails due to the high degree of humidity, organic load and phytotoxic substances. In this work, a solution at an industrial level that uses thermo-malaxation at a temperature close to 65 °C for one or two hours followed by centrifugation in three phases is proposed. In this way, over 40% of the pomace oil that is rich in minor compounds, a solid with a lower degree of humidity (55%), and a liquid aqueous fraction that is rich in bioactive compounds such as phenolics and sugars are obtained. This aqueous fraction can be treated through subsequent storage stages to increase its content of the main phenolic, hydroxytyrosol, to up to 1.77 g/L, decreasing its percentage of insoluble solids by up to 1.9%, making it possible to obtain extracts that are rich in hydroxytyrosol using systems that are commonly in place at the industrial level. The aqueous fraction, without phenolics, could be used for energy production. A solid with a slightly higher fat content than the initial alperujo remains, thus the rest of the oil content can be extracted from it using solvent, making it, once defatted, suitable for application in subsequent bioprocesses.

The main by-product from olive oil extraction (alperujo) was extracted with hot water, citric acid, natural deep eutectic solvent (choline chloride: citric acid), and only choline chloride. The purified extracts were composed of macromolecular complexes constituting polyphenols associated with pectin. The extracts were structurally characterized by FT-IR and solid-NMR spectroscopy and an in vitro test revealed distinct antioxidant and antiproliferative activity, depending on the extracting agents. The choline chloride-extracted complex contained the highest amount of polyphenols among the examined agents, which exhibited a strong antioxidant activity and significant antiproliferative capacity. However, the complex extracted by hot water showed the highest antiproliferative capacity in vitro against the colon carcinoma Caco-2 cell line. In this finding, choline chloride could be used as a novel, green and promising alternative to the conventional extracting agent for the production of complexes that combine the antioxidant activity of phenolic compounds and the physiological effects of pectic polysaccharides.

The formation of the molecule 4,5-dihydroxy-2-cyclopenten-1-one (DHCP) from the thermal treatment of pectin-containing foods was investigated in small-scale laboratory preparation of sterilized vegetable puree (carrot, zucchini and tomato) and fruit puree (peach and mixture of pear and apple) and in commercial baby foods. DHCP attracts attention due to its cytotoxicity as well as potential antiviral and anti-inflammatory effects. However, its effects and the difficulty of its identification in food are mediated in part by the formation of Michael adducts of DHCP with amino acids. The results revealed that DHCP reacted efficiently with cysteine and glutathione, and to a lesser extent with histidine. Mass spectrometry analysis confirmed the formation of adducts of DHCP with amino acids in a model system, being in a real food system difficult to investigate. However, these formed adducts are of potential interest, although it is not known whether they are safe, bioactive or reversible.

The growing interest in natural compounds is helping to improve the management of agro-industrial by-products such as the date seed as sources of such compounds. In this work, the application of a hydrothermal treatment at 160 and 180 °C for 60 min was studied to achieve the solubilization of its phenolic components and sugars in order to obtain biologically active extracts. The percentage of phenols and total sugars in the final extracts were very similar, at 45 and 25% for the 160 and 180 °C treatments, respectively. The treatment at a higher temperature allowed greater solubilization of other components. The antioxidant activity was measured as free-radical scavenging capacity. For the DPPH• method, expressed as EC50, the results were 0.34 and 0.37 mg/L, the TEAC values for the ABTS• method were 6.61 and 3.28 mg/g dried extract, and the values obtained by the ORAC method were 12.82 and 9.91 mmol Trolox/g dried extract, for 160 and 180 °C, respectively. All these values are higher than those of other plant extracts and extracts obtained using the whole date. Therefore, the date seed is a very important source of phenols, and through thermal and chromatographic processes, it is possible to obtain extracts with high antioxidant activity.

The aim of this work was to recover phenolic compounds such as oleacein and oleocanthal from low commercial value olive oils destined for refining [lampante olive oil (LOO)]. For this, the ability of three extraction systems of phenols from oils was evaluated. A new quick and simple extraction method (NM) for obtaining phenols was developed, consisting of the acidified mixture MeOH/H2O (50:50) (v/v) 0.1% formic acid, and it was compared to a conventional method (CM) widely used for the analytical determination of phenolic compounds in olive oil using MeOH: H2O (80:20) (v/v). NM showed a higher yield for the extraction of oleacein with an increase of 14% compared to CM; no significant differences were observed in the extraction of oleocanthal between the two methods. The third method, using two formulations of deep eutectic solvents (DESs) based on ChCl, showed higher extractive efficiency for the two secoiridoids than CM and NM when DES consisted of ChCl and xylitol. On the other hand, the concentrations of oleacein and oleocanthal were determined in 14 samples of blended oils that were previously classified as extra virgin olive oil and LOO according to EU regulation. LOO contained amounts up to 109.89 and 140.16 mg/kg of oleacein and oleocanthal, respectively. Oleacein (>98%) and oleocanthal (>95%) were successfully recovered from phenolic extracts obtained from LOO oils through chromatographic separation and purification by semipreparative high-performance liquid chromatography. Therefore, these low-quality oils are an inexpensive source of bioactive substances.

The aim of this study was to prepare a complex between the olive phenolic compounds, hydroxytyrosol (HT), 3,4-dihydroxyphenylglycol (DHPG) and their mixture, with the soluble and insoluble dietary fiber of apple cell wall. A strong interaction between phenols and the apple cell wall occurred during the drying phase and it was confirmed by ultraviolet–visible spectrometry, Fourier transform infrared spectrometry, differential scanning calorimetry, thermogravimetry and especially by solid-state 13C NMR spectroscopy. The antiradical activity by DPPH, ABTS and ORAC assays confirmed that the simple phenolic HT/DHPG maintained in part their antioxidant activity after complexation with the apple cell wall. In addition, the HT/DHPG-soluble and insoluble fractions obtained after simulated gastrointestinal fluids retained this antioxidant activity. These complexes may be protected from absorption during gastrointestinal transit to reach the colon. In the case of the soluble dietary fiber, an enzymatic treatment, in a simulation of hydrolysis by colonic microflora, released oligomers with potential antioxidant activity from this complex. Therefore, the intake of HT/DHPG bound to the fiber of apple cell wall could provide many of the health benefits associated with dietary fiber, and be fermented by gut bacteria to contribute to a healthy antioxidant environment. © 2019 Elsevier Ltd

Melanosis is an unsolved problem of the crustacean industry and the cause of great loss of value. This study investigates the effect of two potent, natural antioxidants isolated from olive waste (hydroxytyrosol, HT and 3,4-dihydroxyphenylglycol, DHPG) and three novel HT-derivatives containing selenium and sulfur (dihydroxytyrosyl diselenide, N-hydroxytyrosyl selenourea, and N- hydroxytyrosyl thiourea) on the prevention of melanosis in Atlantic ditch shrimp (Palaemonetes varians) during refrigerated storage. These results clearly demonstrate the positive inhibitory effect of DHPG and dihydroxytyrosyl diselenide on delaying melanosis in vivo, although this effect was not dose dependent. The effect was associated with a concomitant-inhibitory effect on tyrosinase activity in vitro. To our knowledge, so far no studies on the prevention of melanosis have been conducted on this small specie of shrimp which is available in large quantities at any time of the year at low cost. Studies with these promising compounds could then be extended to other more economically important species with a greater guarantee of success.

[ES] Procedimiento de obtención de 3,4-dihidroxifenilqlicol (DHFG). La presente invención se refiere a un procedimiento de extracción del fenol 3,4-dihidroxifenilglicol (DHFG) presente en cualquier parte de la planta, productos o subproductos derivados del olivo o cualquier otro producto vegetal de la familia Oleaceae, Orobanchaceae, Plantaginaceae, Compositae, Lamiaceae, Acanthaceae y/o Scrophulariaceae, particularmente en la hoja del olivo, y en el aceite de oliva (CA) con una baja liberación del fenol hidroxitirosol (HT)., [EN] Procedure for obtaining 3,4-dihydroxyphenylqlycol (DHFG). The present invention refers to a process for the extraction of the phenol 3,4-dihydroxyphenylglycol (DHFG) present in any part of the plant, products or by-products derived from the olive tree or any other plant product of the Oleaceae, Orobanchaceae, Plantaginaceae, Compositae family. Lamiaceae, Acanthaceae and/or Scrophulariaceae, particularly in the olive leaf, and in olive oil (CA) with a low release of phenol hydroxytyrosol (HT).

The toxicity on oenological yeasts and plant pathogens of eight deep eutectic solvents (DESs) composed of ChCl:Sucrose (1:2), ChCl:1,4-butanediol (1:5), ChCl:Xylitol (2:1), ChCl:1,2-propanediol (1:1), Fructose:Glucose:Sucrose (1:1:1), Betaine:Sucrose (2:1), Betaine:Sucrose (4:1) and Fructose-Glucose-Sucrose (2:3.6:1) was evaluated and compared with the classic solvents dimethylsulfoxide (DMSO), ethanol and glycerol. Most yeast and bacteria were tolerant to DESs consisting of three sugars in a concentration range of 75–600 x 103mg/L for yeasts and 75–1200 x 103mg/L for bacteria. These DESs showed less toxicity than glycerol or DMSO for most microorganisms. The effect of six DESs, ChCl:Sucrose (1:2), ChCl:Xylitol (2:1), Fructose:Glucose:Sucrose (1:1:1), Betaine:Sucrose (2:1), Betaine:Sucrose (4:1) and Fructose-Glucose-Sucrose (2:3.6:1) in different human cancer cell lines (Caco-2, HeLa and HepG2 cells), as well as in peripheral blood mononuclear cells (PBMCs) from healthy volunteers, was studied using flow cytometry. As a result, DESs at concentrations below 1%, affected tumor cells; however, healthy PBMCs were unaffected. In addition, the solubility of poorly-soluble subtances in water (quercetin, phenylmethylsulfonyl fluoride (PFMS), camptothecin (CPT), oleanolic acid, palmitic acid and Red O oil) was evaluated in all DESs previously tested plus two organic acidbased DESs, Betaine:Levulinic acid (1:2) and ChCl:Glycolic acid:Oxalic acid (1:1.6:0.4). All they were compared with conventional solvents (water, DMSO or ethanol) to determine their efficacy as drug solvents. As a result, DESs solubilized quercetin and CPT in the same range as conventional solvents. The antioxidant properties of quercetin solubilized in two DESs and in DMSO were studied in Caco-2 cells. A solution of tert-butyl hydroperoxide (TBH) was used as an inducer of intracellular reactive oxygen species (ROS), resulting in that quercetin's ability to reduce ROS production did not differ when it was so

Melanosis is an unsolved problem of the crustacean industry and the cause of great loss of value. This study investigates the effect of two potent, natural antioxidants isolated from olive waste (hydroxytyrosol, HT and 3,4-dihydroxyphenylglycol, DHPG) and three novel HT-derivatives containing selenium and sulfur (dihydroxytyrosyl diselenide, N-hydroxytyrosyl selenourea, and N-hydroxytyrosyl thiourea) on the prevention of melanosis in Atlantic ditch shrimp (Palaemonetes varians) during refrigerated storage. These results clearly demonstrate the positive inhibitory effect of DHPG and dihydroxytyrosyl diselenide on delaying melanosis in vivo, although this effect was not dose dependent. The effect was associated with a concomitant-inhibitory effect on tyrosinase activity in vitro. To our knowledge, so far no studies on the prevention of melanosis have been conducted on this small specie of shrimp which is available in large quantities at any time of the year at low cost. Studies with these promising compounds could then be extended to other more economically important species with a greater guarantee of success.

The study investigated the phenols, sugar and the antioxidant capacities of date fruit extracts obtained by organic solvents and by hydrothermal treatment from six different Algerian cultivars at two ripening stages for the first time. The analyzed cultivars exhibited potent antioxidant properties (ferric reducing antioxidant power (FRAP), 1,1-Diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) scavenging capacities) and different phenols regardless of the solvents and the maturity stages. About 18 phenols were identified and quantified, mainly in the hydrothermal extracts. The earlier stages were characterized by high amounts of o-coumaric acid, cinnamic acid and luteolin, with a noticeable absence of quercetin. The tamr stage presented the highest sugar content (78.15–86.85 mg/100 mg dry weight (DW)) with an abundance of glucose. Galactose was present only in some cultivars from the kimri stage (tamjouhert). Uronic acids were mostly detected at the tamr stage (4.02–8.82 mg gallic acid equivalent/100 mg dried weight). The obtained results highlight the potential of using date fruit extracts as natural antioxidants, especially at industrial scales that tend use hydrothermal extraction.

The aim of this research was to investigate the interaction of phenols and pectic polysaccharides during the olive oil extraction process. For this, pectin was extracted from fresh olive fruits and compared to the pectin isolated from the paste resulting from the extraction of the olive oil after milling with malaxation at 30 °C/30 min and subsequent centrifugation of the olive paste from the same lot of olive fruits in a system called ABENCOR (AB). The results indicate that these interactions were enhanced during the olive oil extraction process. In addition, the resulting AB extracts exhibited high antioxidant activity (ORAC) and strong antiproliferative activity in vitro against colon carcinoma Caco-2 cell lines compared to olive fruit extracts. The polyphenols associated mainly with the acidic pectin substance, with a higher content in AB extracts, seem to be responsible for these activities, and appear to maintain their activities in part after complexation. However, even in olive fruit extracts with smaller amounts of phenols in their compositions, pectic polysaccharides may also be involved in antioxidant and antiproliferative activities.

Bladder cancer (BC) is one of the most common human cancers. There is an interest in controlling and treating BC and other types of cancer via the use of natural substances and/or combination chemotherapy. Modified forms of pectin have been reported to possess anticancer bioactivity related to the interaction of galactosyl, a main component of pectin, with galectin-3, a carbohydrate-binding protein that is overexpressed on many types of cancer cells. In this study, the antiproliferative effect on BC of novel modified pectins extracted from olives was evaluated. Pectoliv extracts, with high polyphenol content associated to polysaccharides rich in pectin, exhibited an important antiproliferative capacity in vitro against four human BC cells lines, RT112, T24, J82, and SCaBER. Pectoliv treatment reduced the expression of galectin-1 and galectin-3 and significantly inhibited the agglutination of erythrocytes. Thus, Pectoliv may have the potential for development as a novel galectin-3 inhibitor.

Environmentally friendly natural deep eutectic solvents (NADES) have been shown to efficiently extract a wide range of phenolic compounds from virgin olive oil (VOO). The objective of this work was to optimize the yield of olive oil phenols extracted by NADES based on xylitol/choline choride (Xyl/ChCl). Different extraction and recovery conditions were investigated, including the effect of different extraction operating parameters (temperature, time, VOO:NADES ratio) and subsequent recovery conditions (XAD resin height, wash-water and eluent volume and pH). The highest concentration of phenols (555.36 mg/kg VOO) was obtained from extraction at 40 °C for 1 h, with a 1:1 ratio, using an adsorption resin XAD-16 with bed height of 10 cm, 250 mL acidified wash-water and 300 mL EtOH 100% as eluent. No statistically significant loss of the sum of phenolic compounds was observed when compared with the concentration values obtained by direct analysis in HPLC without the elimination of NADES. Additionally, a sequential desorption with different concentration of ethanol was used to determine the effect of the solvent concentration on polyphenol yield. Polar compounds, such as hydroxytyrosol and tyrosol, were recovered at 81.7% and 83.6%, respectively with 50 and 80% ethanol; however, 100% ethanol was required for the complete elution of oleacein (3,4-DHPEA-EDA) and oleocanthal (p-HPEA-EDA). In this paper we present an effective process for the extraction of polyphenols from VOO by NADES for direct analysis in HPLC and for the recovery and concentration of polyphenols by removing the solvent (NADES) with no losses of yield and solvent recycling.

The natural antioxidant hydroxytyrosol (HT) was used to functionalize a strawberry puree. The effect of the antioxidant on the stability of the two bioactive forms of vitamin C (ascorbic acid-AA and dehydroascorbic acid-DHAA) in strawberry puree stored at 4 °C, compared with the effect on a model system of AA in water, was investigated. In the absence of HT, the concentration of vitamin C in strawberry puree decreased but not in the model system. Low concentrations of HT in strawberry puree (0.05 and 0.1 mg HT/g puree) stabilized vitamin C and improved its antioxidant activity. However, at high concentrations of HT (from 0.5 mg HT/g puree), although the antioxidant activity improved, degradation of vitamin C occurred. Therefore, the concentration of HT used to obtain a functionalized strawberry puree it is very important. An adequate concentration increases the antioxidant activity and protects vitamin C from degradation, developing a functional food. However, an inadequate concentration of HT affects the vitamin C content, which is essential for the human diet because it cannot be biosynthetized by the organism.

The current management of alperujo as the main solid by-product from the two-phase olive oil extraction system has led to the appearance of a new liquid effluent that until now was treated together with the alperujo itself. The composition and antioxidant properties of its bioactive components at different depths of the pond were studied using colorimetric and HPLC with UV and MS detectors, DPPH, reducing power and rancimat. The concentration of suspended solids varied between 1.71 and 8.49 g/L, total fat was between 0.74 and 1.47 g/L, and total phenols were found between 3.74 and 4.11 g/L, which included hydroxytyrosol, 3,4-dihydroxyphenylglycol and tyrosol as the main phenols. Two types of extracts were obtained through two industrial systems with ethyl acetate and by chromotography, with an average content in total sugars of 2.1% and 3.16%, total phenols of 17.9% and 28.6% and hydroxytyrosol of 51.5 and 79.0 mg/g of extract, respectively. The activity presented by the chromatographic extract was higher in terms of free radical sequestering capacity, reducing power and the inhibition of lipid oxidation. Obtaining bioactive extracts would improve the formulation of food with natural components and at the same time would be the first step in a biorefinery to improve the management of the new effluent.

Thermal treatments are the latest developments in the olive oil biorefinery industry to extract bioactive compounds from its by-products, mainly the alperujo. To reach these goals and reduce energy consumption the utilization of deep eutectic solvents has been studied. An initial screening led to define a eutectic mix of choline chloride, glycolic and oxalic acid (DES9) as one of the adequate solvents to increase the solubilization of phenols and sugars, with a temperature reduction from 180 °C to 120 °C. DES9 increased the concentration of acid sugars by six times and the concentration of hydroxytyrosol by 30 times, to up to 85.81 mg/g of dry matter. The activity of DES9 is not due to the activity of each component separately or to the mixture of the two acids, but to the eutectic mixture of all of them. In the future, these solvents could improve the extraction, stability and bioavailability of bioactive compounds and the biorefinery of alperujo.

La industria del aceite de oliva, consciente de la necesidad de eliminar los residuos medioambientalmente nocivos, está evolucionando para lograr el aprovechamiento integral de cada uno de los residuos que se generan de ella. El alperujo subproducto mayoritario del proceso de extracción del aceite de oliva, que retiene el 98% de los fenoles y otros compuestos minoritarios de las aceitunas, está siendo tratado térmicamente permitiendo la solubilización de una gran parte de compuestos de interés que pasan a formar parte de una fracción líquida. Esta fracción líquida está siendo ya utilizada por la industria, y dos antioxidantes fenólicos muy activos, el hidroxitirosol (HT) y el 3,4-dihidroxifenilglicol (DHFG) están siendo recuperados. Esta tesis se centra en el estudio de estabilidad, biodisponibilidad y mejoras de la funcionalidad de estos dos compuestos fenólicos así como en el estudio y recuperación de componentes de la pared celular con actividad biológica a partir de estas fracciones acuosas. La capacidad de las pectinas para actuar como vehículo de liberación de compuestos bioactivos junto con sus propiedades nutracéuticas y funcionales, al actuar como fibra alimentaria soluble, ser aplicada en la conservación de alimentos, además de combatir o prevenir el cáncer, nos ha llevado a considerar esta molécula, ya sea comercial o aislada del propio alperujo, el principal candidato para llevar a cabo estos estudios. Por tanto, en esta tesis doctoral se ha conseguido encapsular mediante formulación en base de pectina, los dos antioxidantes de la aceituna, HT y DHFG, en cantidades suficientes para alcanzar el colon, comprobándose la formación de un complejo pectina-fenol, el cual mantiene parte de la actividad antioxidante de los fenoles, así como su efecto antiinflamatorio in vivo. Así mismo, se han conseguido formular películas y recubrimientos comestibles con los dos antioxidantes HT y DHFG, presentando buenas propiedades fisicoquímicas, y protegiendo del ataque de h

Extracts rich in pectic polysaccharides associated to polyphenols were obtained from alperujo, the by-product of olive oil extraction, by different thermal treatments and subsequent chemical treatments. The resulting “Pectoliv” extracts exhibited strong antioxidant activities and a high antiproliferative capacities in vitro against colon carcinoma Caco-2 and leukemia monocytic THP-1 cell lines. Bleaching of the extracts with sodium chlorite removed the phenolic compounds and significantly reduced antiproliferative and antioxidant activities, confirming that these were due mainly to the associated polyphenols present in Pectoliv. However, even after bleaching, these activities remained very similar to that of a commercial citrus modified pectin obtained by chemical treatment from citrus pectin, which has been implicated in cancer treatment and prevention. Thus Pectolivs have a high potential as antiproliferative or antioxidant agents.

La presente invención se refiere al uso del compuesto 3,4-dihidroxifenilglicol (DHFG), composiciones que lo comprendan y métodos de uso de los mismos como fitorreguladores efectivos para el tratamiento de cultivos y malas hierbas

The present invention relates to the use of the compound 3,4-dihydroxyphenylglycol (DHPG), compositions containing same, and methods for using said compositions as effective plant growth regulators for the treatment of crops and weeds

The development of thermal treatments is helping to optimize the management of waste generated by the two-phase olive oil extraction system. A new treatment reactor, based on the steam explosion system, has been scaled up to the industrial level and offers several physical and chemical advantages. The reactor has been adapted to work into the pomace oil extractors. Chemical advantages include the efficient solubilization of simple phenols, like hydroxytyrosol, and sugars in the liquid fraction, and a significant reduction of humidity and toxicity of the residual solid fraction, in which cellulose and oil are concentrated, making the solid residual waste more suitable for subsequent bioprocess applications. All of these parameters will lead to the widespread use of steam treatment in the near future to improve the management and obtain the maximum exploitation of this byproduct.

The aim of the present work was to evaluate the effects of a thermal pre-treatment of olive mill solid waste (OMSW) and phenol extraction process on the semi-continuous anaerobic digestion of this pre-treated waste during a prolonged operational period (275 days) in order to assess the organic loading rates (OLR) of 1 ad 2 g Volatile Solids (VS)/(L·d). The anaerobic digestion of thermally pre-treated and de-phenolized OMSW was stable at an OLR of 1 g VS/(L·d), which permitted a specific production rate of 172 ± 60 mL CH4/(g VS·d). However, the system was not able to operate at an OLR of 2 g VS/(L·d), which resulted in the total failure of the process. Regardless of the applied OLR, the phenolic compounds were effectively degraded and the inhibition thresholds were not reached. The inhibition of the anaerobic digestion process at an OLR of 2 g VS/(L·d) was probably due to the overloading of the system, indicated by the accumulation of organic matter and volatile fatty acids. The operation of the anaerobic digester under stable conditions allowed for high profitability for the proposed bio-refinery concept, which would still be profitable at a phenol extract price above 51.8 €/kg, which is 90% lower than the current price of 520 €/kg.

Cocoa bean husk extract (CBHE)was obtained by thermal treatment at 170 °C for 30 min. The CBHE was added to a virgin olive oil jam in a freeze-dried form or encapsulated. Phenols, theobromine, and antioxidant activity were determined over 28 days in both jams and compared to a control jam. Total phenols, epicatechin, and theobromine were higher in the water fraction of the jam with non-encapsulated extract (J-CBHE)at day 28: 1140, 19.14 and 70 ppm, respectively. For the oil fraction of J-CBHE, total phenols, epicatechin, and theobromine contents were 120, 2.54, and 0.13 ppm at day 28, respectively. The oil content in jam with the non-encapsulated extract showed the best Rancimat induction time, with a 32% increase compared to the control, keeping for longer without becoming rancid. Nevertheless, the jam with encapsulated extract showed the best retention of bioactive compounds during the storage time.

Three olive modified pectin extracts have been produced by heat and acid treatment of the major by-product of olive oil production. Their effect on proliferation of the colon carcinoma Caco-2 and the leukemia monocytic THP-1 cell lines has been studied in order to determine possible anti-tumor properties. All extracts inhibited proliferation at some of the concentrations ranging from 1 to 10 mg ml−1. Interestingly none of the extracts inhibited the growth of confluent Caco-2 cells, showing the specificity of the antiproliferative effect for the transformed Caco-2 phenotype. All the extracts inhibited agglutination of red blood cells by galectin-3, a lectin involved in tumor growth, metastasis, and immune cell regulation that has been proposed as a mediator of the anti-tumor effects of modified pectins. In addition, activation of caspase-3 in THP-1 cells indicates that treatment with the pectin-rich extracts triggers apoptosis. These results point to a possible use as health-promoting food ingredients or supplements.

Strawberries have antioxidant, cardiovascular, and antiproliferative properties. The agroindustrial production of strawberry concentrate generates a food waste after extrudation that is usually landfilled. This strawberry extrudate is a rich source of valuable bioactive compounds such as phenols and sugars. In the present study, industrial thermal treatments currently in use for the valorization of other agricultural wastes were determined to be suitable for the treatment of strawberry extrudate. Thermal treatment conditions in the range of 90 °C to 200 °C were studied. Thermal treatment at 150 °C for 60 min without acid addition was the most efficient process based on the solubilization of sugars and phenols as well as the antioxidant capacity of the liquid phase produced. Instead of sending this residual fraction to landfill, such treatment would permit the use of strawberry extrudate as a source for the recovery of valuable bioactive compounds.

Steam-explosion is a promising technology for recovering phenolic compounds from olive mill solid waste (OMSW) due to its high impact on the structure of the fibre. Moreover, the recovery of the phenols, which are well-known microbial inhibitors, could improve the subsequent biomethanization of the dephenolized OMSW to produce energy. However, there is a considerable lack of knowledge about how the remaining phenolic compounds could affect a long-term biomethanization process of steam-exploded OMSW. This work evaluated a semi-continuous mesophilic anaerobic digestion of dephenolized steam-exploited OMSW during a long operational period (275 days), assessing different organic loading rates (OLRs). The process was stable at an OLR of 1 gVS/(L·d), with a specific production rate of 163 ± 28 mL CH4/(gVS·d). However, the increment of the OLR up to 2 gVS/(L·d) resulted in total exhaust of the methane production. The increment in the propionic acid concentration up to 1486 mg/L could be the main responsible factor for the inhibition. Regardless of the OLR, the concentration of phenolic compounds was always lower than the inhibition limits. Therefore, steam-exploited OMSW could be a suitable substrate for anaerobic digestion at a suitable OLR

The objective of this research was to evaluate the effect of the addition of two antioxidants naturally present in olives, hydroxytyrosol (HT) and 3,4-dihydroxyphenylglycol (DHPG), to a pectin-fish gelatin edible film on the preservation of raw beef meat during refrigerated storage. A new composite film that included beeswax was also prepared, resulting in a reduction in the film's oxygen permeability. Results showed that the meat samples wrapped with film containing antioxidants reduced the formation of oxidation products in the form of thiobarbituric acid reaction substances (TBARS) compared with control film without antioxidants. HT added at 0.5% to the film with beeswax suppressed the lipid oxidation of beef meat during 7 days of storage at 4 °C, possibly by the combined effect of acting as an oxygen barrier and the specific antioxidant activity. The interference of plasticizer agents (glycerol and sorbitol) incorporated to the film on the TBARS method was showed for the first time.

The interaction of strawberry cell wall with hydroxytyrosol (HT) and 3,4-dihydroxyphenylglycol (DHPG), two potent phenolic antioxidants naturally found in olive fruit with important biological properties, was investigated. The interaction occurred with drying and seemed to be more complex, strong and irreversible than a simple association. MALDI TOF-TOF analysis suggested covalent (ester bond) and non-covalent (strong hydrogen-bonding, mostly) interactions. The oxygen radical absorbance capacity (ORAC) assay confirmed that the phenols maintained partially their antioxidant activity after binding to the soluble dietary fraction. This soluble dietary fiber was obtained following digestion simulated in vitro with gastric and intestinal fluids. Although the antioxidant activity of HT and DHPG was affected by the dietary fiber interaction, this activity was restored when polysaccharide size was reduced by enzymatic treatment, suggesting that a similar process could occur in the colon. Thus, the use of this novel antioxidant-enriched soluble dietary fiber as a functional food ingredient could potentially promote intestinal health.

[Background] Cocoa bean husk (CBH) is the principal by-product of the cocoa industry and a significant agro-industrial residue. In this study, using different hydrothermal treatments of CBH, it is shown that CBH is an important source of bioactive compounds, including theobromine, epicatechin and catechin., [Results] Treatment over 150 °C significantly increased the yield of total and individual phenols and theobromine as well as the antioxidant capacity of the liquid fraction. A total of 52 different genotypes of CBH harvested in two seasons of production were analyzed. Overall, higher amounts of total phenols, theobromine and epigallocatechin were detected in samples from the 2015 season, while samples from 2014 had higher quantities of catechin and similar quantities of epicatechin., [Conclusion] CBH treatment at 170 °C for 30 min produces an antioxidant-rich extract high in phenols (55 mg g), sugars (220 mg g) and theobromine (56 mg g) that is suitable for applications in the food, cosmetic and nutraceutical industries. © 2018 Society of Chemical Industry.

The present invention relates to the use of the compound 3,4-dihydroxyphenylglycol (DHPG), compositions containing same, and methods for using said compositions as effective plant growth regulators for the treatment of crops and weeds. [EN], La presente invención se refiere al uso del compuesto 3,4-dihidroxifenilglicol (DHFG), composiciones que lo comprendan y métodos de uso de los mismos como fitorreguladores efectivos para el tratamiento de cultivos y malas hierbas. [ES]

La presente invención se refiere al uso del compuesto 3,4-dihdroxifenilglicol (DHFG), composiciones que lo comprendan y métodos de uso de los mismo como fitorreguladores efectivos para el tratamiento de cultivos y malas hierbas.

In a society where the environmental conscience is gaining attention, it is necessary to evaluate the potential valorization options for agricultural biomass to create a change in the perception of the waste agricultural biomass from waste to resource. In that sense, the biorefinery approach has been proposed as the roadway to increase profit of the agricultural sector and, at the same time, ensure environmental sustainability. The biorefinery approach integrates biomass conversion processes to produce fuels, power, and chemicals from biomass. The present review is focused on the extraction of value-added compounds, anaerobic digestion, and composting of agricultural waste as the biorefinery approach. This biorefinery approach is, nevertheless, seen as a less innovative configuration compared to other biorefinery configurations, such as bioethanol production or white biotechnology. However, any of these processes has been widely proposed as a single operation unit for agricultural waste valorization, and a thoughtful review on possible single or joint application has not been available in the literature up to now. The aim is to review the previous and current literature about the potential valorization of agricultural waste biomass, focusing on valuable compound extraction, anaerobic digestion, and composting of agricultural waste, whether they are not, partially, or fully integrated.

Purpose The objective of this study was to evaluate the capacity of modified phenols synthesized from hydroxytyrosol, a natural olive oil phenol, specifically those containing a selenium or sulphur group, to inhibit lipid peroxidation. Methods The compounds’ abilities to inhibit lipid peroxidation in liver microsomes obtained from vitamin E-deficient rats were compared to hydroxytyrosol. Results All synthetic compounds had a significant higher ability to inhibit lipid peroxidation than hydroxytyrosol. Selenium derivates displayed a higher antioxidant activity than sulphur derivatives. In addition, the antioxidant activity increased with a higher number of heteroatoms in the hydroxytyrosol molecular structure. Conclusion The study shows, for the first time, the ability of synthetic compounds, derived from the most active phenol present in olives in free form (hydroxytyrosol), and containing one or two atoms of sulphur or selenium, to inhibit the lipid peroxidation of vitamin E-deficient microsomes. The antioxidant activity of five thioureas, a disulfide, a thiol, three selenoureas, a diselenide, and a selenonium were evaluated and the results showed a higher inhibition of lipid peroxidation than the natural phenol. Selenium and sulphur derivatives of hydroxytyrosol are novel antioxidants with the potential to supplement the lack of vitamin E in the diet as natural alternatives for the prevention of diseases related to oxidative damage.

Purpose: Evaluate the efficacy of hydroxytyrosol in the local treatment of inflammatory colitis. Currently, the existing treatments for inflammatory bowel diseases does not cure the disease and it is associated with high rates of side effects and complications. Hydroxytyrosol is a phenyl-ethyl-alcohol derived from the hydrolysis of oleuropein and present in olive oil, previous studies have demonstrated the anti-inflammatory effect of dietary hydroxytyrosol supplement, with no toxicity. Materials & Methods: Colitis has been induced by using Trinitrobenzene Sulfonic Acid at 40 rats. They were divided into four groups randomly: 10 rats without treatment; 10 rats with pectin/alginate mixture; 10 rats treated with pectin/alginate + olive oil; 10 rats treated with pectin/alginate + olive oil + hydroxytyrosol. Animals were sacrificed 10 days after induction of trinitrobenzene sulfonic acid, receiving 5 days of continuous treatment. Samples of the rectal area were studied and observed under a microscope to determine the damage by Hunter scoring modified, assessing inflammatory infiltration, number of intestinal walls involved, damage to the mucosal architecture, and edema. Results: When the rectum was analyzed in a global way, nonsignificant differences were observed; however, when performing an individualized analysis, statistically significant differences in the inflammatory infiltrate are present in the samples, which were evaluated using the ANOVA and Student-T statistics. Conclusions: Local treatment with the natural antioxidant hydroxytyrosol combined with pectin/alginate and olive oil of inflammatory bowel disease has been shown to be effective against inflammatory infiltration of TNBS-induced colitis.

The aim of the study was to test the neuroprotective effect of hydroxytyrosol (HT) on experimental diabetic retinopathy. Animals were divided in four groups: (1) control nondiabetic rats, (2) streptozotocin-diabetic rats (DR), (3) DR treated with 1 mg/kg/day p.o. HT, and (4) DR treated with 5 mg/kg/day p.o. HT. Treatment with HT was started 7 days before inducing diabetes and was maintained for 2 months. In the DR group, total area occupied by extracellular matrix was increased, area occupied by retinal cells was decreased; both returned to near-control values in DR rats treated with HT. The number of retinal ganglion cells in DR was significantly lower (44%) than in the control group, and this decrease was smaller after HT treatment (34% and 9.1%). Linear regression analysis showed that prostacyclin, platelet aggregation, peroxynitrites, and the dose of 5 mg/kg/day HT significantly influenced retinal ganglion cell count. In conclusion, HT exerted a neuroprotective effect on diabetic retinopathy, and this effect correlated significantly with changes in some cardiovascular biomarkers.

This study explored the interaction of pectin with 3,4-dihydroxyphenylglycol (DHPG), a potent phenolic antioxidant naturally found in olive fruit, via encapsulation into pectinate beads. MALDI TOF-TOF analysis supported the formation of complexes between DHPG and pectin. A combination of covalent bonds (ester bonds) and non-covalent interactions, mostly hydrogen bonding, were suggested as the cause of DHPG-pectin complex formation. Free radical scavenging assays confirmed that DHPG maintained its antioxidant activity after complexation and after a digestion simulated in vitro with gastric and intestinal fluids. Therefore, DHPG-pectin beads could reach the large intestine and contribute to a healthy antioxidant environment.

A characterization of the phenolic profile of 25 cocoa genotypes established in a Mexican gene bank was carried out. From five different extraction methods commonly used for phenols, extraction with acidified methanol–water was chosen as the best to quantify the concentrations of theobromine and individual phenols in cocoa beans. High concentrations of individual and total phenols were found for genotypes native to Mexico (like RIM105, M031, and M033) or from Peru and Ecuador (INI10), but not the commercial mix (CAF), and were directly associated with their antioxidant activities. Despite the loss of some theobromine and phenols during fermentation, epicatechin remained in the fermented cotyledon in high concentrations. This study could help promote the commercialization of Mexican genotypes of cocoa and reports the possibility of upcycling fermented cocoa husks, which are rich in bioactive compounds and fiber, as novel functional extracts for use in food formulation or for nutraceutical purposes.