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The present invention relates to an olive oil enriched with oleanolic acid that comprises a concentration of oleanolic acid between 580 and 650 mg/kg. This functional olive has proven to be effective in the treatment and prevention of type 2 Diabetes Mellitus and pre-diabetes. Also, the invention relates to a process for the preparation of said functional olive oil enriched with oleanolic acid.

Diabetes, one of the most prevalent chronic diseases, represents a major public health problem worldwide. In 2017, there were 425 million diabetic people in 2017, and a significant increase in the prevalence is expected in the next years, estimating that the number of diabetics in the world will achieve 629 million in 2045. An essential topic of diabetes approach is prevention, especially in people at high risk. Oleanolic acid (OA), a natural component of olive (Olea europaea L.), has demonstrated antidiabetic action in vitro and in experimental animals. However, a similar action had not been proved in humans. The PREDIABOLE (PREvention of DIABetes with OLEanolic acid) Study is a randomised and controlled trial, entirely performed in primary care, designed to assess whether the regular intake of an OA-enriched olive oil is effective in the prevention of diabetes. Diabetes is preceded by a period of dysglycemia, known as prediabetes, in which plasma glucose is higher than normal but not meet the criteria for diabetes. Prediabetes is defined by impaired fasting glucose (IFG), and/or impaired glucose tolerance (IGT) and/or a glycated hemoglobin (HbA1C) in the range 5.7¿6.4% (39¿47 mmol/mol). Prediabetes is associated with obesity, dyslipidemia and hypertension. Compared to euglycemics, people with both IFG and IGT have 20-fold higher risk of developing type 2 diabetes at short time. Therefore, they are ideal target population to investigate new preventive strategies against diabetes. In PREDIABOLE, prediabetic individuals (IFG + IGT) of both sex (176 patients, 30-80 years old) were randomised to receive OA-enriched olive oil (equivalent-dose 30 mg OA/day) (intervention group; IG) or the same oil not enriched (control group; CG). The main outcome was the incidence of new onset type 2 diabetes in both groups. After a median 27.5 months of follow-up, 48 new diabetes cases occurred, 31 in the CG and 17 in the IG. Multivariate adjusted hazard ratio was 0.45 (95% CI, 0.24-0.

Aim To assess whether the regular intake of an oleanolic acid (OA)‐enriched olive oil is effective in the prevention of diabetes. Methods In the PREDIABOLE study, prediabetic individuals (impaired fasting glucose and impaired glucose tolerance) of both sexes (176 patients, aged 30‐80 years) were randomized to receive 55 mL/day of OA‐enriched olive oil (equivalent dose 30 mg OA/day) [intervention group (IG)] or the same oil not enriched [control group (CG)]. The main outcome was the incidence of new‐onset type 2 diabetes in both groups. Results Forty‐eight new diabetes cases occurred, 31 in the CG and 17 in the IG. The multivariate‐adjusted hazard ratio was 0.45 (95% CI, 0.24‐0.83) for the IG compared with the CG. Intervention‐related adverse effects were not reported. Conclusions The intake of OA‐enriched olive oil reduces the risk of developing diabetes in prediabetic patients. The results of the PREDIABOLE study promote the use of OA in new functional foods and drugs for the prevention of diabetes in individuals at risk of developing it.

Procedimiento de obtención de oleuropeína. La presente invención se refiere a un procedimiento de obtención de oleuropeína a partir de hojas de olivo que comprende las siguientes etapas: a) secado de las hojas de olivo; b) peletizado de las hojas secas obtenidas en la etapa (a); y c) extracción sólido/líquido de los pellets obtenidos en la etapa (b) con un disolvente seleccionado de agua, metanol, etanol y cualquiera de sus mezclas.

Procedimiento de obtención de oleuropeína. La presente invención se refiere a un procedimiento de obtención de oleuropeína a partir de hojas de olivo que comprende las siguientes etapas: a) secado de las hojas de olivo; b) peletizado de las hojas secas obtenidas en la etapa (a); y c) extracción sólido/líquido de los pellets obtenidos en la etapa (b) con un disolvente seleccionado de agua, metanol, etanol y cualquiera de sus mezclas.

Procedimiento de obtención de oleuropeína. La presente invención se refiere a un procedimiento de obtención de oleuropeína a partir de hojas de olivo que comprende las siguientes etapas: a) secado de las hojas de olivo; b) peletizado de las hojas secas obtenidas en la etapa (a); y c) extracción sólido/líquido de los pellets obtenidos en la etapa (b) con un disolvente seleccionado de agua, metanol, etanol y cualquiera de sus mezclas.

This work tackles the study of the quality and authenticity of oils labeled and commercialized as extra virgin sacha inchi oil. Major and minor components as triglycerides, fatty acid methyl esters, tocopherols, sterols and hydrocarbons are determined as well as other physicochemical parameters (density, viscosity, acidity and peroxide value). The results showed that some of the commercialized oils do not fulfill the basic requirement established in the regulation such as the content of ¿-linolenic acid, higher than 44.7 or 55.0% in the cases of P. volubilis and P. huayllabambana, respectively. The calculated stigmasterol/campesterol ratio for genuine sacha inchi oils should be around 4, however not all commercial oils analyzed comply with this requirement. The presence of the flavons sesamin and sesamolin indicates the addition of compounds from sesame oils. Finally, some of the commercial oils showed to contain trans fatty acids although this was not accompanied by the sterene hydrocarbon presence.

© 2015 John Wiley & Sons, Ltd. Analytical interest of OA determination in human serum has increased owing to the increasing interest in pharmaceutical research by pharmaceutical properties. A simple, specific, precise and accurate GC method with flame ionization detector (FID) developed and validated for the determination of oleanolic acid (OA) in human serum (HS). To an aliquot of HS, internal standard was added and a combination of liquid-liquid extraction with a mixture of diethyl ether-isopropyl alcohol, filtration and consecutive GC resulted in separation and quantification of OA. The organic phase was analyzed using a GC system equipped with a 30×0.25mm i.d. Rtx-65TG capillary column and FID detection. Total chromatographic time was 10min and no interfering peaks from endogenous components in blank serum were observed. The OA/internal standard peak area ratio was linearly fitted to the OA concentration (r=0.992) over the range 10-1500ng/mL. The mean serum extraction recovery of OA was 96.7±1.0% and the lower limit of quantification based on 5mL of serum was 10.7ng/mL. The intra-day coefficient of variation ranged from 1.3 to 3.6% and inter-day varied from 1.4 to 4.5%. The developed method was used to study the pharmacokinetics of OA after oral administration in humans. The assay was simple, sensitive, precise and accurate for the use in the study of the mechanisms of absorption and distribution of OA in humans.

Olive leaves are an agricultural residue resulting from the pruning of olive trees that may be considered an available industrial byproduct. The olive tree is biochemically characterized for the presence of secoiridoids, carbohydrates, sugar alcohols, and terpenoids. Oleuropein, especially abundant in the olive leaves (up to 14% DW), have the greatest biological interest. The polyalcohol mannitol, which represents approx. a 3% of the leaf dry weight, has been used by the food and pharmaceutical industries as excipient, due to its high sweetness and poor caloric power. Likewise, oleanolic acid is present in the olive leaf in significant concentrations (z3% DW) and has been endorsed with very important pharmacological properties. In this work we describe a novel procedure for the determination of the major bioactive compounds from the olive leaf by SPE and HPLC. These bioactive compounds were determined in the four most significant Spanish Olea europaea cultivars. Olive leaf contains important amounts of oleanolic acid, oleuropein and mannitol, whose recovery could be interesting for the pharmaceutical, cosmetics and food industries. The analytical methodology presented in this work would serve as a very suitable tool for the control of any industrial process designed to obtain these high added-value compounds.

The suitability of using visible/near infrared spectroscopy (Vis/NIR), as a rapid and non-destructive technique for monitoring the quality of argan seeds (Argania spinosa Skeels) was studied. The analyzed parameters were the fatty acid composition of argan seed oil, seed moisture content, seed oil content and oil stability index (OSI). The ratio between major unsaturated and saturated fatty acids (U/S) during the oxidation assay at constant temperature was studied. Values from infrared drying were used as a laboratory reference for the moisture. Argan seed oil content was determined by Soxhlet extraction. A fatty acid analysis was carried out by gas chromatography and the OSI was determined by the Rancimat test. Predictive models of argan seed moisture, ratio U/S and OSI showed good accuracy. Therefore, Vis/NIR measurements can be used for controlling several argan seed quality parameters. This procedure might be of interest to the argan oil industry, which is currently in the process of modernization and expansion.

This work deals with the characterization of the main glyceridic and unsaponifiable components of oils obtained from Sacha inchi (Plukenetia huayllabambana L.) seed ecotypes collected during two harvests in the Department of Amazonas in Peru. The seed-oil yield was 30.3¿41.2%; standing out are the high percentages of the ¿3- and ¿6-fatty acids series whose ranges lie within those of the present Regulation for Sacha inchi oils. Triacylglycerols with even equivalent carbon number (ECN; 36¿42) were the main components. Minor glyceridic polar compounds such as oxidized triglycerides, diglycerides, monoglycerides, and free fatty acids were determined by high-performance size exclusion chromatography. The low campesterol/stigmasterol ratio (1:6), unusual in the majority of vegetable oils, stands out. Regarding aliphatic hydrocarbons, these oils showed a particular profile for the saturated series of odd and even carbon atom numbers. According to our results Sacha inchi P. huayllabambana oils can be offered as a good alternative to P. volubilis, the species mainly commercialized for this vegetable oil.

[Introducción]: En estos últimos años, han surgido numerosos artículos sobre las posibles aplicaciones terapéuticas de los ácidos terpénicos. Para facilitar los estudios farmacocinéticos y toxicológicos de estos compuestos, se ha desarrollado un procedimiento analítico para la determinación de los ácidos triterpénicos pentacíclicos en suero humano, basado en la cromatografía líquida de alta resolución (HPLC). Se describe la extracción, purificación y posterior separación, identificación y cuantificación mediante HPLC de los ácidos oleanólico y betulínico. [Material y métodos]: Para analizar las diferencias en la actividad biológica de los ácidos oleanólico y betulínico, se estudiaron mediante absorción UV-vis, las interacciones entre estos dos ácidos y las proteínas del suero humano. La validez del método analítico se estableció mediante las determinaciones de linealidad, recuperación, precisión y los límites de detección y cuantificación. La repetibilidad del método fue buena y los límites de cuantificación para el betulínico y el oleanólico fueron de 12,7 y 14,3 ng/mL, respectivamente. Ambos compuestos pueden distinguirse bien por orden de elución durante la cromatografía líquida. La identificación de los triterpenos se realizó por comparación con los de los patrones correspondientes. La cuantificación se llevo a cabo usando patrón interno. [Resultados y conclusiones]: Los espectros de absorción en el UV–vis (240-340 nm) indican que las estructuras de las proteínas son modificadas en presencia de los ácidos oleanólico y betulínico.

This work reports for the first time the presence of pentacyclic triterpenic acids in Argania spinosa. By solid/liquid extraction with absolute ethanol and GC-FID analysis, we report that ursolic acid is the major triterpene in the leaf and fruit of argan (0.10-0.44% DW), followed by significant amounts of oleanolic acid (0.05-0.19% DW). Their contents in the leaf were four times higher than in the fruit. Minor levels of betulinic and maslinic acids were also determined in the fruit pulp. Our results suggest that the developmental stage of the plant organ and the environmental conditions modulate the biosynthesis of triterpenic acids in argan. Advanced stages of ontogeny and severe climatic conditions induced a selective production of lupenyl and ursanyl structures. Argan fruits and leaves constitute interesting raw materials for the obtaining of ursolic and oleanolic acids that are strongly demanded by the functional food and pharmaceutical industries. The utilization of dry pulp of argan fruits, a by-product of the argan oil industry, for the obtaining of new triterpene-based formulations of high added value would increase the profitability of these crops and might help to guarantee the survival of the A. spinosa forests in the long term. Practical applications: Argan fruits and leaves constitute interesting raw materials for obtaining ursolic and oleanolic acids. Morocco accumulates every year more than 44500tons of dry fruit pulp as a by-product of the argan oil industry. The utilization of this biomass for the obtaining of bioactive compounds of high added value that could be used in the design of new functional food and drugs would help to increase the profitability of the argan crops and represent an intelligent manner of contributing to the A. spinosa survival. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

This work establishes a new procedure for the extraction and analysis of pentacyclic triterpenes, with which fruits and leaves from three Spanish olive cultivars (“Picual”, “Hojiblanca”, and “Arbequina”) has been studied. The leaf contains important amounts of oleanolic acid (3.0−3.5% DW), followed by significant concentrations of maslinic acid and minor levels of ursolic acid, erythrodiol, and uvaol. The abundance and profile of triterpenoids change during the leaf ontogeny. In the fruit, triterpenes are exclusively located in the epicarp at concentrations 30-fold lower than that in the leaf. Maslinic acid is the main triterpenoid, only accompanied of oleanolic acid. Along the ripening the levels of these triterpenes decreased. All the analyzed leaves and fruits come from the same agricultural estate, with identical climate and culturing conditions. For this reason, the found differences could majorly be attributable to the genetic factors of the olive cultivars.

Molecular distillation, or short-path distillation (SPD), is particularly appropriate for processing of low-volatility compounds, which are easily altered at high temperature. Olea europaea L. leaves constitute an olive tree by-product very interesting for their natural antioxidants content. In this research, molecular distillation technology has been applied to obtain high-value-added compounds by the SPD fractionation of an olive tree leaf extract. The process consists of two stages: (a) ethanolic extraction of the olive leaves, followed by incorporation of the extract into glycerine and (b) molecular distillation of the glycerine enriched in olive leaf extract compounds (terpenic and phenolic compounds). Four molecular distillation tests under different conditions were carried out. Results showed that 80.9% 3,4-dihydroxy-phenylethanol (hydroxytyrosol) was recovered from the glycerine admixture under a pressure of 1.50-2.00 mbar, a temperature of 190°C and a feed rate of 15 mL/min.

A study was carried out to determine the changes in phenolic composition induced by tuberculosis infection in olive trees. Four ethanolic extracts were compared: olive leaf from shoots affected by Pseudomonas savastanoi pv. Savastanoi, nodules induced by this bacteria, leaf from healthy (asymptomatic) shoots, and shoots. Among the differences found, the presence of a phenolic compound in nodules was significant in much larger quantities than in leaf or shoots. Mass spectrometric analysis showed this compound to be verbascoside. The enhancement of its biosynthesis could be related to the defense mechanisms of the tree in the nodules induced by P. savastanoi and suggests the possibility of exploration of natural and biotechnological sources of this compound.

Research into finding new uses for olive products, particularly by-products of olive oil production, is of great relevance not only to the economy, but also to the environment, in the towns where olives are grown. A large number of research articles has been published dealing with the chemical composition of olives and olive oil; however, only a few studies have centered on isolating and identifying compounds in the olive leaf. In this article an overview of the present body of knowledge on the chemical composition of the olive leaf will be presented. Also to be discussed is the use of solid residue, namely, the olive leaf and the olive stone. Both of these types of residue result from olive oil and table olive production, and can be used as a renewable energy source, as well as to obtain high added-value compounds. The latter, bioactive compounds are directed towards the cosmetic, pharmaceutical, and natural food supplements markets, all of which are currently highly receptive to products of natural origin., La investigación de nuevos aprovechamientos del olivar y en particular de lo subproductos del proceso de producción del aceite, tiene gran relevancia tanto en la economía como en el medio ambiente de los pueblos donde se desarrolla este cultivo. Son numerosos los trabajos publicados sobre la composición química de la aceituna y el aceite de oliva, en cambio sólo existen algunos estudios sobre el aislamiento e identificación de los compuestos de la hoja de olivo, en esta contribución se revisan los conocimientos sobre la composición química de la hoja de olivo, así como, las utilizaciones de los residuos sólidos -hoja de olivo y hueso de aceituna- que se originan en la producción del aceite de oliva y de aceitunas de mesa, como energía renovable y para la obtención de compuestos de alto valor añadido. Estos últimos, compuestos bioactivos dirigidos a los mercados de los aditivos alimentarios naturales, farmacéutico y cosmético, todos ellos muy receptivos en la actualidad a los productos de origen natural.

[EN] The invention relates to a method of obtaining high-value-added compounds from olive leaves. The inventive method comprises the following steps, namely: a first step in which the leaves are subjected to solid-liquid extraction with organic solvents, preferably hexane or ethanol, and the crude extract thus obtained is vacuum concentrated; and a second step in which the crude extract is fractionated by means of supercritical CO2 countercurrent column extraction and separation into two cells with different fixed pressure and/or temperature conditions which alter the dissolving power of the CO2, thereby precipitating different compounds. The invention can be used to extract natural products of interest from olive leaves for the food, pharmaceutical and cosmetic industries, such as waxes, squalene, beta -carotene, alpha -tocopherol, oleuropein, hydroxytyrosol and other phenolic compounds, beta-sitosterol, alpha - and beta-amyrin, erythrodiol, uvaol and other terpenic alcohols, oleanolic acid, ursolic acid and maslinic acid, among others., [ES] Mediante el procedimiento de la invención se obtienen compuestos de alto valor añadido a partir de hoja de olivo. En una primera etapa se someten las hojas a extracción sólido-líquido con disolventes orgánicos, preferentemente hexano o etanol, y se concentra a vacío el extracto bruto obtenido. En una segunda etapa se realiza un fraccionamiento de ese extracto bruto por extracción en contracorriente en columna con COz supercrítico y separación en dos celdas en que se fijan diferentes condiciones de presión y/o temperatura que cambian el poder disolvente del CO2, precipitando diferentes compuestos. El procedimiento de la invención permite extraer de la hoja de olivo productos naturales de interés para las industrias alimentaria, farmacéutica y cosmética, como ceras, escualeno, beta- caroteno, alfa-tocoferol, oleuropeina, hidroxitirosol y otros compuestos fenólicos, beta-sitosterol, a y beta-amirina, eritrodiol, uvaol y otros alcoholes terpénicos, ácido oleanólico, ácido ursólico y ácido maslínico, entre otros.

High-oleic high-palmitic sunflower oil (HOHPSO) has been obtained from field-grown mutant sunflower seeds CAS-12. The fatty acid and triacylglycerol compositions, the thermo-oxidative stability and the physical properties of the HOHPSO were determined and compared with those of the conventional and high oleic sunflower oils and those of a liquid fraction of palm oil (olein). The major fatty acids of the HOHPSO were monoenes (57.7% oleic, 7.3% palmitoleic) and palmitic (27, 8%), while the content of linoleic acid was low (2.3%). The saturated fatty acids were almost absent from the sn-2 position and, thus, the major triacylglycerol (TAG) molecular species were those with one or two saturated fatty acids at the sn-1, 3 positions and oleic acid at the sn-2 position (mainly POO and POP). Total polar compounds and their distribution in oxidised TAG monomers and TAG polymers were determined after 10 h at 180 °C. The HOHPSO showed enhanced thermal stability, producing half the amount of total polar compounds, and much less TAG polymers, as the palm olein. The stability index (Rancimat) of the HOHPSO was unusually high (19 h at 120 °C). The thermal properties of the HOHPSO (determined from the differential scanning calorimetry thermograms) were different from those of the palm olein. The HOHPSO presents lower solid fat con-tents than the palm olein above 15 °C and hence remains liquid at common working temperatures.

Los ácidos terpénicos y en particular el ácido oleanólico son de utilidad en la industria farmacéutica, entre otras, por su actividad antitumoral, antiinflamatoria y bactericida. Se describe un procedimiento para la obtención de ácido oleanólico, de las hojas de olivo, mediante extracción sólido/líquido con etanol, posterior tratamiento del extracto y concentración en condiciones definidas, siendo posible obtener en una sola etapa de extracción un rendimiento del 90 % del contenido de la hoja (2-3 %, referido al peso de hoja), y con un grado de pureza superior al 95 %. La materia prima es un subproducto, procedente de la poda anual del olivar y de la limpieza de las aceitunas. Se describe un método para la cuantificación de los ácidos terpénicos del extracto alcohólico de la hoja de olivo mediante el fraccionamiento en cromatografía preparativa en capa fina y cuantificación por cromatografía gaseosa con patrón de ácido betulínico., The terpenic acids, mainly the oleanolic acid, are used for the pharmaceutical industry, among other, for its antitumoral, anti-inflammatory and germicide activities. A process of obtainment of oleanolic acid from olive leafs is described. The process includes solid/liquid extraction with ethanol and treatment of the extract and concentration under defined conditions, being possible to obtain in a single extraction stage a yield of 90% of the leaf content (2-3%, referred to the leaf weight) and with richness in excess of 95%. The raw material is a by-product, coming from that of pruning yearly of the olive grove and of the cleaning of the olives. A method is described for the quantification of the terpenic acids from olive leaf of the alcoholic extract, by preparative thin layer chromatography fractionation and gas liquid chromatography quantification with betulinic acid standard.

[ES] Se describe un método analítico, sencillo y rápido, para la cuantificación de escualeno en aceites comestibles. El método consiste en realizar primero una metilación alcalina en frío de la muestra grasa disuelta en hexano y, posterior análisis de la disolución de hexano por cromatografía gaseosa usando patrón interno. Se presentan una recta de calibrado con patrones cromatográficos puros, así como, los coeficientes de variación de muestras de aceites con alto, medio y bajo contenido en escualeno., [EN] A simple and rapid analytical method for the quantification of squalene in vegetable oils is described. The method consists of a cold alkaline methylation of the oil sample diluted with hexane followed by quantitation by gas chromatography with internal standard. A calibration curve obtained using different standard solutions, and coefficients of variation for three different samples with high, medium and low content of squalene, are reported.

Sistema actuador de mandos para una estación remota autochequeada de teleoperaciones, caracterizado por estar compuesto por tres módulos, dos de los cuales, encargados del gobierno lógico de los mandos, son idénticos ya que únicamente les distingue una programación eléctrica realizada en el conector al cual van enchufados, conteniendo el tercer módulo las etapas finales de actuación, referentes a dieciséis mandos; los dos módulos de gobierno lógico de los mandos establecen los diálogos con la unidad de control de la estación remota a través de los siguientes canales comunes de comunicación: Un bus de selección de ocho líneas, a través del cual los módulos reciben el número de mando que se desea seleccionar; un bus de operación de dos líneas a través del cual los módulos reciben el control de las operaciones elementales; un bus de actuación de dos líneas a través del cual se canalizan las órdenes de ejecución y anulación de los mandos; un bus de datos de cuatro líneas, a través del cual estos módulos envían a la unidad de control, el número del mando que ha quedado seleccionado y, finalmente, un bus falso que será utilizado cuando en la estación se haya asociado a un determinado telemando una telemedida con objeto de proceder a una telerregulación de ésta.

Un sistema modular de adquisición y conformación de datos analógicos y digitales para una estación remota de teleoperadores de alta flexibilidad, caracterizado por estar compuesto por tres módulos diferentes: modulo de teleseñalizaciones, modulo de telemedidas numericas y módulos de telemedidas analógicas, compartiendo los mismos canales de comunicación con la unidad de control de la estación de la que forman parte, de tal forma que éstos son utilizados secuencialmente en el tiempo por cada uno de los módulos, mediante la activación selectiva de las etapas de salida compuestas por cuatro puertas de tres estados en cada modulo y la utilización de un decodificador especifico en las entradas de aquellos; cada uno de los módulos que componen este sistema, dispone de un mecanismo de multiplexacion en su etapa de salida para suministrar el bus común una primera información, a través de las puertas de tres estados, mediante la cual, el modulo en cuestión se identifica, indicando de cual de los tres tipos citados es, lo que hace posible el que dichos módulos sean directamente intercambiables en su posición espacial.

Unidad de control para una estación remota autochequeada de teleoperadores, caracterizada por estar constituida por un microprocesador junto a una serie de memorias muertas que almacenan el programa de actuación, estando formado éste por un programa principal que mantiene a la estación remota en espera permanente de una orden enviada desde la estación central, la cual, una vez validada, se interpreta generándose un salto incondicional a la rutina correspondiente que será una de las siguientes: leer conjunto de datos, seleccionar mando, ejecutar mando y anular mandos; asimismo, esta unidad de control incluye una etapa de transmisión/recepción de tipo asíncrono.