ES2378809A1 - Method for extracting bioinsecticide derivatives from the plant artemisia absinthium l - Google Patents
Method for extracting bioinsecticide derivatives from the plant artemisia absinthium l Download PDFInfo
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- ES2378809A1 ES2378809A1 ES201031389A ES201031389A ES2378809A1 ES 2378809 A1 ES2378809 A1 ES 2378809A1 ES 201031389 A ES201031389 A ES 201031389A ES 201031389 A ES201031389 A ES 201031389A ES 2378809 A1 ES2378809 A1 ES 2378809A1
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- plant
- extracts
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- extraction
- extracting
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0203—Solvent extraction of solids with a supercritical fluid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/028—Flow sheets
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Botany (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Procedimiento de extracción de derivados bioinsecticidas de la planta Artemisia absinthium L.Extraction procedure for bioinsecticide derivatives of the Artemisia absinthium L plant.
La presente memoria descriptiva se refiere, como su título indica, a un procedimiento de extracción de derivados bioinsecticidas de la planta Artemisia absinthium L, comúnmente conocida como Ajenjo, caracterizado por unos parámetros agronómicos y económicos de producción orgánica de la planta con un quimiotipo específico con el fin de producir extractos orgánicos consistentes en aceite esencial y extracto no volátil, y en otra fase extractos supercríticos de composición química caracterizada, obtenidos con CO_{2} a presión como disolvente mayoritario, siendo las principales aplicaciones industriales de los extractos y aceites así extraídos su uso como materia base para formulaciones de insecticidas naturales, de especial aplicación en agricultura ecológica para el control de insectos plaga, especialmente áfidos y lepidópteros, así como su uso como ingrediente para formulaciones mixtas, en combinaciones sinergistas junto con otros componentes activos naturales.The present specification refers, as its title indicates, to a procedure for the extraction of bioinsecticide derivatives of the Artemisia absinthium L plant, commonly known as Wormwood, characterized by agronomic and economic parameters of organic production of the plant with a specific chemotype with in order to produce organic extracts consisting of essential oil and non-volatile extract, and in another phase supercritical extracts of characterized chemical composition, obtained with pressurized CO2 as the majority solvent, the main industrial applications of the extracts and oils thus extracted its use as a base material for formulations of natural insecticides, of special application in organic farming for the control of pest insects, especially aphids and lepidoptera, as well as its use as an ingredient for mixed formulations, in synergistic combinations together with other natural active components.
La Artemisia absinthium L, denominada comúnmente "ajenjo", es una planta herbácea medicinal de la familia de las asteráceas. Cada año produce desde su base rama rectas, de 0.50 a 1.20 m de altura, que se secan en otoño tras la fructificación. Las partes basales de estas ramas permanecen durante el invierno y en la estación siguiente se producen nuevas ramas a partir de sus yemas. Toda la planta tiene una coloración blanquecina, debido a su abundancia de pelos que cubren prácticamente toda la superficie de tallo y hojas. Su área de distribución abarca principalmente desde Asia Central hasta Europa Occidental, con algunas localidades en el Norte de África. Ha sido una planta muy cultivada por su carácter aromático, especialmente en los Estados Unidos, la antigua URSS y Francia. La planta se recolecta cuando está en plena floración, entre julio y agosto. El primer año la recolección es escasa, pero en los años sucesivos es posible hacer dos recolecciones, en julio y a finales de octubre, si las condiciones meteorológicas lo permiten. Artemisia absinthium L , commonly referred to as " wormwood ", is a medicinal herbaceous plant of the Asteraceae family. Every year it produces straight branches from its base, 0.50 to 1.20 m high, which are dried in autumn after fruiting. The basal parts of these branches remain during the winter and in the following season new branches are produced from their buds. The whole plant has a whitish coloration, due to its abundance of hairs that cover practically the entire surface of stem and leaves. Its range covers mainly from Central Asia to Western Europe, with some locations in North Africa. It has been a very cultivated plant for its aromatic character, especially in the United States, the former USSR and France. The plant is collected when it is in full bloom, between July and August. The first year the collection is scarce, but in the following years it is possible to make two collections, in July and at the end of October, if the weather conditions allow it.
Aunque la forma más común de obtener el ajenjo que se comercializa son los cultivos, en muchos lugares se recogen poblaciones silvestres de esta planta, obteniéndose así un producto heterogéneo en calidad y rendimiento. También se han desarrollado métodos de micropropagación de ajenjo para producir plantas con el fin de obtener metabolitos secundarios.Although the most common way to get wormwood crops are marketed, in many places they are collected wild populations of this plant, thus obtaining a product Heterogeneous in quality and performance. Have also been developed wormwood micropropagation methods to produce plants with the In order to obtain secondary metabolites.
Esta planta era conocida desde muy antiguo ya por los egipcios y transmitida después a los griegos gracias a sus múltiples aplicaciones curativas como tónico, febrífugo y antihelmíntico. Además de por sus virtudes medicinales, el ajenjo ha sido utilizado tradicionalmente como aromatizante, empleándose su principio activo absintina (sustancia amarga) en la preparación de bebidas comerciales como por ejemplo el vermouth. El aceite esencial de ajenjo y el alcohol constituyen los ingredientes básicos de la absenta, bebida que fue prohibida en algunos países a principios del siglo XX por su toxicidad. Los efectos neurotóxicos y alucinógenos, así como su nefrotoxicidad son atribuidos a la tuyona, una monoterpenocetona presente en su aceite esencial.This plant was known since ancient times by the Egyptians and later transmitted to the Greeks thanks to their multiple healing applications such as tonic, febrifuge and anthelmintic In addition to its medicinal virtues, wormwood has traditionally used as a flavoring, using its active substance absintin (bitter substance) in the preparation of commercial drinks such as vermouth. Essential oil of wormwood and alcohol constitute the basic ingredients of the Absinthe, a drink that was banned in some countries in the early 20th century for its toxicity. The neurotoxic and hallucinogenic effects, as well as its nephrotoxicity are attributed to the tuyona, a Monoterpenoketone present in its essential oil.
El ajenjo ha sido asimismo empleado desde tiempos remotos para el tratamiento de trastornos digestivos ya que estimula el apetito, previene la formación de gases en el tubo digestivo, estimula la secreción de jugos gástricos y de bilis tanto por la vesícula biliar como por el hígado y protege frente a dolencias hepáticas. Asimismo presenta propiedades antipiréticas, antioxidantes y antiinflamatorias. También se ha utilizado como antídoto para el opio y otros venenos depresores del sistema nervioso central. También se le conocen aplicaciones en perfumes, como por ejemplo encontramos en la Patente inglesa GB0105589 "Composiciones de perfume", o como elementos para su uso en medicinas alternativas, como por ejemplo se describe en la patente española ES2076896 "Procedimiento para producir moxas".Absinthe has also been used since ancient times for the treatment of digestive disorders since it stimulates appetite, prevents the formation of gases in the digestive tract, stimulates the secretion of gastric juices and bile both by the gallbladder and by the liver and protects against liver ailments. It also has antipyretic, antioxidant and anti-inflammatory properties. It has also been used as an antidote for opium and other central nervous system depressant poisons. Also known in perfume applications, as for example found in English patent GB0105589 " Perfume compositions ", or as elements for use in alternative medicines, as for example described in Spanish patent ES2076896 " Procedure for producing moxas ".
Asimismo son conocidas tradicionalmente, y frecuentemente utilizadas, sus propiedades insecticidas y repelentes en la lucha contra las plagas, especialmente pulgones, ácaros, cochinillas, hormigas, orugas, y otros insectos pulverizando su extracto sobre las plantas afectadas. También repele la mariposa de la col, ácaros, roya, caracoles y babosas si se pulveriza preventivamente. La aplicación tradicional del ajenjo ha sido realizada hasta ahora por métodos tradicionales como la maceración de la planta, decocción, infusión o mediante purín fermentado. Estos métodos, aparte de que su utilización dosificación y efectividad está basada casi siempre en la tradición y en la experiencia, presentan el inconveniente de que no permiten un completo aprovechamiento de toda la capacidad bioinsecticida de la planta, además de no ser aprovechables industrialmente, ya que no es predecible ni el aprovechamiento, ni la concentración ni la efectividad de las soluciones utilizadas.They are also traditionally known, and frequently used, its insecticidal and repellent properties in the fight against pests, especially aphids, mites, mealybugs, ants, caterpillars, and other insects spraying their extract on the affected plants. It also repels the butterfly of cabbage, mites, rust, snails and slugs if sprayed preventively The traditional application of wormwood has been done so far by traditional methods such as maceration of the plant, decoction, infusion or by fermented slurry. These methods, apart from its use dosage and effectiveness It is almost always based on tradition and experience, they have the disadvantage that they do not allow a complete harnessing the entire bioinsecticidal capacity of the plant, besides not being industrially usable, since it is not predictable neither the exploitation nor the concentration nor the effectiveness of the solutions used.
Aunque los plaguicidas naturales se han utilizado durante cientos de años para proteger los cultivos, estos han sido reemplazados casi totalmente durante los últimos años por compuestos de síntesis más eficaces. Sin embargo, el aumento de los problemas asociados a resistencias cruzadas, riesgos para la salud pública y daños al medioambiente, han promovido la búsqueda de productos naturales con propiedades plaguicidas. Además estos productos naturales pueden presentar nuevos modos de acción que reducen el riesgo de resistencias cruzadas. Son conocidos y utilizados muchos insecticidas orgánicos, como por ejemplo los descritos en la Patente alemana DE9200220 "Procedimiento para la elaboración de un insecticida almacenable rico en Azadirachtin a partir de semillas de Neem", y en las Patentes españolas ES8802602 "Procedimiento de preparar ingrediente activo para insecticidas" y ES0262168 "Un método para producir una nueva composición insecticida", derivados de distintos productos naturales distintos del ajenjo.Although natural pesticides have been used for hundreds of years to protect crops, they have been almost completely replaced in recent years with more effective synthetic compounds. However, the increase in problems associated with cross-resistance, risks to public health and damage to the environment have promoted the search for natural products with pesticide properties. In addition, these natural products may present new modes of action that reduce the risk of cross resistance. Many organic insecticides are known and used, such as those described in German Patent DE9200220 " Process for the preparation of a storable insecticide rich in Azadirachtin from Neem seeds ", and in Spanish patents ES8802602 " Method of preparing active ingredient for insecticides "and ES0262168" A method to produce a new insecticidal composition ", derived from different natural products other than wormwood.
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A pesar de ello, se necesita encontrar insecticidas todavía más selectivos y biodegradables para reemplazar a los plaguicidas de síntesis que persisten en el medio ambiente y poseen un amplio espectro de toxicidad. Ello es especialmente relevante ya que la producción orgánica mediante agricultura ecológica es un mercado emergente, para el que existe una demanda cada vez mayor de agroquímicos naturales.Despite this, you need to find even more selective and biodegradable insecticides to replace to synthetic pesticides that persist in the environment and They have a broad spectrum of toxicity. It is especially relevant since organic production through agriculture Ecological is an emerging market, for which there is a demand growing of natural agrochemicals.
Para solventar esa necesidad se ha ideado el procedimiento de extracción de derivados bioinsecticidas de la planta Artemisia absinthium L. objeto de la presente invención, el cual consigue un aprovechamiento óptimo de los extractos de dicha planta, con resultados reproducibles y aplicables industrialmente. Para ello, se han establecido los parámetros agronómicos y económicos de producción orgánica de la planta del ajenjo (Artemisia absinthium L.) con un quimiotipo específico en parcelas experimentales con el fin de producir extractos orgánicos consistentes en aceite esencial y extracto no volátil, y en otra fase de extracción, extractos supercríticos de composición química caracterizada, obtenidos con CO_{2} a presión como disolvente mayoritario, con efectos repelentes experimentalmente demostrados frente a larvas de lepidópteros, por ejemplo de la especia Spodoptera littoralis, y pulgones además de tener efectos sobre el desarrollo radicular de cebada Hordeum vulgare.To solve this need, the procedure for extracting bioinsecticide derivatives from the Artemisia absinthium L plant has been devised. object of the present invention, which achieves optimum use of the extracts of said plant, with reproducible and industrially applicable results. For this, the agronomic and economic parameters of organic production of the wormwood plant ( Artemisia absinthium L. ) have been established with a specific chemotype in experimental plots in order to produce organic extracts consisting of essential oil and non-volatile extract, and in another extraction phase, supercritical extracts of characterized chemical composition, obtained with pressurized CO2 as a major solvent, with experimentally proven repellent effects against larvae of lepidoptera, for example of the spice Spodoptera littoralis , and aphids in addition to having effects on the root development of barley Hordeum vulgare .
Las principales aplicaciones industriales de los extractos y aceites así extraídos consisten en su uso como materia base para formulaciones de insecticidas naturales, de especial aplicación en agricultura ecológica para el control de insectos plaga, especialmente áfidos y lepidópteros, así como su uso como ingrediente para formulaciones mixtas, en combinaciones sinergistas junto con otros componentes activos naturales.The main industrial applications of extracts and oils thus extracted consist of their use as matter base for natural insecticide formulations, especially application in organic farming for insect control plague, especially aphids and lepidoptera, as well as its use as ingredient for mixed formulations, in synergistic combinations together with other natural active components.
Este procedimiento de extracción de derivados bioinsecticidas de la planta Artemisia absinthium L. que se presenta aporta múltiples ventajas sobre los disponibles en la actualidad siendo la más importante que específica una metodología de producción mediante el cultivo en campo de un quimiotipo seleccionado y mediante una extracción controlada de la materia prima, propiciando una producción controlada, predecible e industrializable.This procedure of extraction of bioinsecticidal derivatives of the Artemisia absinthium L plant. that is presented provides multiple advantages over those currently available, being the most important that specifies a production methodology by cultivating a selected chemotype in the field and by controlling the raw material, promoting controlled, predictable and industrializable production.
Asimismo debemos destacar la ventaja de control en origen que implica la estandarización química y biológica.We must also highlight the control advantage in origin that implies chemical and biological standardization.
Es importante destacar que este procedimiento de extracción genera unos productos con ausencia de tuyonas tóxicas en el aceite esencial.It is important to note that this procedure of extraction generates products with absence of toxic tuyonas in the essential oil
Otra importante ventaja es que la producción de extracto supercrítico con CO_{2} a presión como disolvente mayoritario, permite optimizar el rendimiento del proceso de extracción, propiciando su aplicación industrial y su rentabilidad económica.Another important advantage is that the production of supercritical extract with CO2 under pressure as solvent majority, allows to optimize the performance of the process extraction, promoting its industrial application and profitability economical
Para comprender mejor el objeto de la presente invención, en la figura -1- se ha representado el procedimiento de extracción de derivados bioinsecticidas de la planta Artemisia absinthium L. En dicha figura -1- se muestra un diagrama de bloques simplificado de las fases diferenciadas que componen el procedimiento: fase de producción (1), fase de extracción de extractos orgánicos (2), y fase de extracción (4) con CO_{2} (22) a presión como disolvente principal, obteniendo como resultados por un lado aceite esencial y extracto no volátil (3), proveniente de la fase de extracción de extractos orgánicos (2), y por otro lado extractos supercríticos (5) provenientes de la fase de extracción (4).In order to better understand the object of the present invention, in Figure -1- the process of extracting bioinsecticidal derivatives of the Artemisia absinthium L plant has been represented. In said figure -1- a simplified block diagram of the differentiated phases that make up the process is shown: production phase (1), organic extract extraction phase (2), and extraction phase (4) with CO2 } (22) under pressure as the main solvent, obtaining on the one hand essential oil and non-volatile extract (3), from the extraction phase of organic extracts (2), and on the other hand supercritical extracts (5) from the extraction phase (4).
La figura -2- muestra unas curvas del rendimiento de extractos supercríticos (5) obtenidos en la fase de extracción (4), representados en el eje vertical, en función de la cantidad de CO_{2} (22) a presión como disolvente principal, representada en el eje horizontal, obtenidas experimentalmente en diversas condiciones de presión y temperatura:Figure -2- shows some curves of the yield of supercritical extracts (5) obtained in the phase of extraction (4), represented on the vertical axis, depending on the amount of CO2 (22) under pressure as the main solvent, represented on the horizontal axis, obtained experimentally in various pressure and temperature conditions:
- \bullet?
- La curva (41) muestra los resultados obtenidos con una presión de 18.0 Mpa y una temperatura de 40ºC,Curve (41) shows the results obtained with a pressure of 18.0 Mpa and a temperature of 40 ° C,
- \bullet?
- la curva (42) muestra los resultados obtenidos con una presión de 18.0 Mpa y una temperatura de 50ºC,curve (42) shows the results obtained with a pressure of 18.0 Mpa and a temperature of 50 ° C,
- \bullet?
- la curva (43) muestra los resultados obtenidos con una presión de 13.5 MPa y una temperatura de 40ºC,curve (43) shows the results obtained with a pressure of 13.5 MPa and a temperature of 40 ° C,
- \bullet?
- la curva (44) muestra los resultados obtenidos con una presión de 13.5 MPa y una temperatura de 50ºC,curve (44) shows the results obtained with a pressure of 13.5 MPa and a temperature of 50 ° C,
- \bullet?
- la curva (45) muestra los resultados obtenidos con una presión de 9.0 MPa y una temperatura de 40ºC, ythe curve (45) shows the results obtained with a pressure of 9.0 MPa and a temperature of 40 ° C, and
- \bullet?
- la curva (46) muestra los resultados obtenidos con una presión de 9.0 MPa y una temperatura de 50ºC.curve (46) shows the results obtained with a pressure of 9.0 MPa and a temperature of 50 ° C
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La figura -3- muestra una imagen obtenida en el microscopio electrónico de una hoja de ajenjo a 2000x.Figure -3- shows an image obtained in the electron microscope of a wormwood leaf at 2000x.
La figura -4- muestra una imagen obtenida en el microscopio electrónico de una hoja de ajenjo a 400x.Figure -4- shows an image obtained in the Electron microscope of a wormwood leaf at 400x.
La figura -5- una representación gráfica de los derivados obtenidos a partir de la planta.Figure -5- a graphic representation of the derivatives obtained from the plant.
La figura -6- muestra una representación simplificada de la estructura molecular de los principales compuestos terpénicos obtenidos en el aceite esencial de Artemisia absinthium L.Figure -6- shows a simplified representation of the molecular structure of the main terpenic compounds obtained in the essential oil of Artemisia absinthium L.
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El procedimiento de extracción de derivados bioinsecticidas de la planta Artemisia absinthium L. objeto de la presente invención, comprende básicamente en su realización preferente, como puede apreciarse en la figura -1-, tres fases diferenciadas:The procedure for extracting bioinsecticide derivatives from the Artemisia absinthium L plant. object of the present invention, basically comprises in its preferred embodiment, as can be seen in Figure -1-, three distinct phases:
- \bullet?
- fase de producción (1),production phase (1),
- \bullet?
- fase de extracción de extractos orgánicos (2), obteniendo aceite esencial y extracto no volátil (3),extract extraction phase organic (2), obtaining essential oil and non-volatile extract (3),
- \bullet?
- fase de extracción (4) de extractos supercríticos (5), con CO_{2} (22) a presión como disolvente principal.extraction phase (4) of supercritical extracts (5), with CO2 (22) under pressure as main solvent
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La fase de producción (1) comprende el cultivo (6) en campo de un quimiotipo seleccionado por su adaptabilidad al cultivo y por su composición química mediante la multiplicación preferentemente realizada mediante esquejes o semillas en vivero-semillero (7) para su posterior plantación en el terreno de asiento. Este terreno de asiento estará preferentemente ubicado en zonas altas con pluviométrica superior a los 400-450 mm anuales y se trabajará mediante cultivo mecanizado. El cultivo entra en producción en el primer año de su plantación, recolectándose (8) las hojas y sumidades floridas cuando las plantas se encuentran en estadio fenológico de plena floración para posteriormente someterse a un proceso de secado (9) y posterior molido (10), obteniendo el material recolectado (11). El proceso de secado (9) se realiza preferentemente a la sombra, bajo corriente de aire y durante un período de 8 días aproximadamente.The production phase (1) comprises the cultivation (6) in the field of a chemotype selected for its adaptability to the crop and for its chemical composition by means of the multiplication preferably carried out by means of cuttings or seeds in nursery-seedbed (7) for later planting in the seating area This seating area will preferably be located in high areas with rainfall greater than 400-450 mm per year and will be worked by mechanized cultivation. The crop goes into production in the first year of its plantation, collecting (8) the leaves and flowering tops when the plants are in a phenological stage of full flowering to subsequently undergo a drying process (9) and subsequent grinding (10) , obtaining the collected material (11). The drying process (9) is preferably carried out in the shade, under a stream of air and for a period of approximately 8 days.
La fase de extracción de extractos orgánicos (2) se realiza mediante hidrodestilación (12) y extracción orgánica (13) del material recolectado (11), obteniendo aceite esencial y extracto no volátil (3).The extraction phase of organic extracts (2) is carried out by hydrodestilation (12) and organic extraction (13) of the collected material (11), obtaining essential oil and non-volatile extract (3).
La fase de obtención (4) de extractos supercríticos (5) con CO_{2} (22) a presión como disolvente principal se realiza utilizando una bomba de compresión (47) con un filtro (48), un cilindro de extracción (15), dos colectores (16, 17), un dispositivo de refrigeración (18) cilíndrico, un intercambiador de calor (19), un sensor de presión (20) y un medidor de flujo (21). Para ello el material recolectado (11) se introduce primeramente en el cilindro de extracción (15) y es embebido simétricamente con materiales porosos inertes que permiten un flujo homogéneo de CO_{2} (22), a continuación se calienta hasta que se alcanza una temperatura de 40ºC, para a continuación comprimir en la bomba (47) el CO_{2} (22) hasta conseguir una presión de 90 bar, momento en el que el fluido supercrítico a la presión de trabajo llena el cilindro de extracción (15), regulándose en los dos colectores (16, 17) la presión, mediante las oportunas válvulas, y la temperatura mediante el dispositivo de refrigeración (18), de tal forma que el primero de los colectores (16) sirve para eliminar compuestos pesados, como ceras, y el segundo colector (17) para la recogida del aceite esencial obtenido como extracto supercrítico (5). El valor medio de tamaño de partícula del material recolectado utilizado es preferentemente de 0.5 mm., y el flujo de gas a través del cilindro extractor (15) a 25º y 1 atm es preferentemente de 10,5 l/min.The phase of obtaining (4) supercritical extracts (5) with CO2 (22) under pressure as the main solvent is carried out using a compression pump (47) with a filter (48), an extraction cylinder (15) , two manifolds (16, 17), a cylindrical cooling device (18), a heat exchanger (19), a pressure sensor (20) and a flow meter (21). For this, the collected material (11) is first introduced into the extraction cylinder (15) and is symmetrically embedded with inert porous materials that allow a homogeneous flow of CO2 (22), then it is heated until a temperature of 40 ° C, then compress the CO2 (22) in the pump (47) until a pressure of 90 bar is achieved, at which time the supercritical fluid at the working pressure fills the extraction cylinder (15) , regulating in the two manifolds (16, 17) the pressure, by means of the appropriate valves, and the temperature by means of the cooling device (18), such that the first of the manifolds (16) serves to eliminate heavy compounds, such as waxes, and the second collector (17) for the collection of the essential oil obtained as a supercritical extract (5). The average particle size value of the collected material used is preferably 0.5 mm., And the gas flow through the extractor cylinder (15) at 25 ° and 1 atm is preferably 10.5 l / min.
Los extractos así obtenidos (3, 5), o sus combinaciones, está previsto que se utilicen como materia base para formulaciones de insecticidas naturales, o bien combinados con otros componentes activos naturales para formulaciones mixtas de tipo sinergista, principalmente para el control de insectos plaga, como por ejemplo áfidos ó lepidópteros en agricultura ecológica.The extracts thus obtained (3, 5), or their combinations, it is intended to be used as a base material for natural insecticide formulations, or combined with others natural active components for mixed type formulations synergist, mainly for pest insect control, such as for example aphids or lepidoptera in organic farming.
La efectividad de este procedimiento ha sido
verificada experimentalmente. Para ello se han realizado numerosos
estudios de poblaciones de ajenjo para analizar la composición
química del aceite esencial de A. absinthium L. En la mayoría
de los casos los compuestos mayoritarios son \alpha y
\beta-tuyonas, sin embargo, también se han
encontrado aceites de ajenjo sin tuyonas, hecho que representa una
ventaja en el uso de los extractos de ajenjo en la industria
alimentaria. En algunos casos los componentes mayoritarios
encontrados son cis-epoxiocimeno, acetato de
crisantenilo, acetato de sabinilo o una mezcla de ellos, dependiendo
principalmente del origen de la planta. De acuerdo con sus
componentes mayoritarios, las poblaciones de A. absinthium L.
de la Península Ibérica se dividen en siete quimiotipos con
composición química significativamente distinta. Además del origen,
existen numerosos factores que pueden afectar a la composición del
aceite esencial, como son las condiciones de crecimiento y el estado
de desarrollo de la
planta.The effectiveness of this procedure has been verified experimentally. For this, numerous studies of wormwood populations have been carried out to analyze the chemical composition of the essential oil of A. absinthium L. In most cases the major compounds are α and β-tuyonas, however, wormwood oils without tuyonas have also been found, which represents an advantage in the use of wormwood extracts in the food industry. In some cases the major components found are cis-epoxyocimeno, chrysanthenyl acetate, sabinyl acetate or a mixture of them, depending mainly on the origin of the plant. According to their major components, the populations of A. absinthium L. The Iberian Peninsula is divided into seven chemotypes with a significantly different chemical composition. In addition to the origin, there are numerous factors that can affect the composition of the essential oil, such as the growth conditions and the state of development of the
plant.
Se han utilizado cultivos con características agroclimáticas diferentes, junto con otras poblaciones distintas, se han estudiado química y biológicamente para conocer la evolución de los metabolitos y el potencial antiparasitario e insecticida de esta especie. Para ello se han realizado valoraciones anuales de los extractos y aceites esenciales de las poblaciones mediante cromatografía de gases masa (GC-MS) y ensayos de actividad biológica (insecticida, antiparasitaria y fitotóxica).Cultures with characteristics have been used different agroclimatic, along with other different populations, are have studied chemically and biologically to know the evolution of the metabolites and the antiparasitic and insecticidal potential of this species. For this, annual assessments of the extracts and essential oils of the populations through mass gas chromatography (GC-MS) and assays of biological activity (insecticide, antiparasitic and phytotoxic).
Se puede observar una importante variación, tanto en la composición cualitativa como cuantitativa, entre aceites de una misma población clónica cultivados en diferentes condiciones de luz y temperatura. Las condiciones no controladas en invernadero, se relacionan con un aceite más rico en monoterpenos oxigenados y con una menor cantidad de sesquiterpenos.An important variation can be observed, both in the qualitative and quantitative composition, between oils from the same clonic population grown under different conditions of light and temperature. The uncontrolled conditions in the greenhouse, they are related to an oil richer in oxygenated monoterpenes and with a smaller amount of sesquiterpenes.
Del mismo modo, se han observado variaciones en la composición química del aceite esencial, provocadas por las condiciones de crecimiento, en un estudio comparativo realizado con plantas de A. absinthium L. cultivadas in vitro, en invernadero y en campos de cultivo. Se observó cómo la composición de las plantas cultivadas in vitro era totalmente diferente a las otras dos, con ausencia de monoterpenos y tuyonas y presencia de compuestos de mayor peso molecular, mientras que las plantas cultivadas en invernadero y en el campo presentaron tuyonas y monoterpenos en elevada proporción.Similarly, variations in the chemical composition of the essential oil, caused by growth conditions, have been observed in a comparative study conducted with A. absinthium L plants. grown in vitro , in the greenhouse and in crop fields. It was observed how the composition of the plants grown in vitro was totally different from the other two, with the absence of monoterpenes and tuyonas and the presence of compounds of greater molecular weight, while the plants grown in the greenhouse and in the field presented tuyonas and monoterpenes in high proportion
El aceite esencial suele consistir en una mezcla más o menos compleja de compuestos terpénicos, compuestos fenólicos de bajo peso molecular y compuestos que contienen nitrógeno o azufre. Todos estos compuestos están muy ampliamente distribuidos entre las plantas vasculares y se sintetizan durante el desarrollo normal de la planta y la composición química del aceite es generalmente característica de cada especie.The essential oil usually consists of a mixture more or less complex of terpenic compounds, phenolic compounds low molecular weight and nitrogen containing compounds or sulfur. All these compounds are very widely distributed between vascular plants and are synthesized during development normal plant and the chemical composition of the oil is Generally characteristic of each species.
El interés del aceite esencial radica en la actividad de sus componentes, ya sea por su carácter aromático, por su toxicidad, como por su funcionalidad fisiológica. Los componentes mayoritarios del aceite esencial de las especies de Artemisia, como podemos ver en la Fig. 6, son fundamentalmente terpénicos, pertenecientes a diversos tipos estructurales, monoterpenos (hidrocarburos, alcoholes, cetonas, esteres, aldehídos, óxidos) y sesquiterpenos (hidrocarburos, óxidos y alcoholes).The interest of the essential oil lies in the activity of its components, either for its aromatic character, for its toxicity, as per its physiological functionality. The components essential oil majority of Artemisia species, such as we can see in Fig. 6, they are fundamentally terpenic, belonging to various structural types, monoterpenes (hydrocarbons, alcohols, ketones, esters, aldehydes, oxides) and sesquiterpenes (hydrocarbons, oxides and alcohols).
El rendimiento del aceite esencial en A. absinthium L. se encuentra entre el 0.2-0.6% sobre el peso fresco del material vegetal, siendo la \beta-tuyona (23), uno de los compuestos con más relevancia, que puede aparecer en concentraciones superiores al 30%.The essential oil yield in A. absinthium L. It is between 0.2-0.6% of the fresh weight of the plant material, with β-tuyone (23), one of the most relevant compounds, which can appear in concentrations greater than 30%.
A pesar de que tradicionalmente se había descrito la \beta-tuyona (23) como compuesto mayoritario del aceite esencial de ajenjo, han sido muchos autores los que a lo largo de los años han descrito plantas con bajo contenido en tuyonas o incluso sin ellas, describiéndose diferentes quimiotipos que contienen como compuesto mayoritario acetato de cis-crisantenilo (26), cis-crisantenol (27), cis-epoxiocimeno (24), acetato de sabinilo (25) o acetato de bornilo (31).Although it had traditionally been β-tuyone (23) described as compound majority of the wormwood essential oil, have been many authors those who over the years have described plants with low content in tuyonas or even without them, describing different chemotypes containing as the majority compound acetate cis-chrysanthenyl (26), cis-chrysanthenol (27), cis-epoxyocimeno (24), sabinyl acetate (25) or bornyl acetate (31).
Otros compuestos terpénicos abundantes descritos en el aceite esencial son alcanfor (28) y cineol (29), siendo también frecuentes aunque en cantidades menores otros mono y sesquiterpenos como linalol (32), borneol (30), camazuleno (33), selineno (38), elemol (39), espatulenol (40).Other abundant terpenic compounds described in the essential oil are camphor (28) and cineole (29), being also frequent although in smaller quantities other mono and sesquiterpenes such as linalool (32), borneol (30), camazulene (33), selineno (38), elemol (39), spatulenol (40).
La concentración de sesquiterpenos identificados en A. absinthium L. no suele superar el 10% del aceite esencial, siendo los más frecuentes el \beta-cariofileno (34), el germacreno-D (35), el óxido de cariofileno (36) y el \alpha-bisabolol (37).The concentration of sesquiterpenes identified in A. absinthium L. It does not usually exceed 10% of the essential oil, the most frequent being β-Caryophylene (34), Germacrene-D (35), Caryophylene Oxide (36) and α-Bisabolol (37).
Otra familia de compuestos identificados en el aceite esencial de numerosas especies son los bencenoides derivados del ácido cinámico en la ruta del siquimato.Another family of compounds identified in the Essential oil of numerous species are benzenoids derived of cinnamic acid in the route of the siquimato.
Así mismo, en varias especies del género Artemisia se han identificado pequeñas concentraciones de algunos compuestos de esta familia como eugenol, metil eugenol, elemicina y cinamato de etilo y metilo.Likewise, in several species of the genus Artemisia have identified small concentrations of some compounds of this family such as eugenol, methyl eugenol, elemicin and ethyl and methyl cinnamate.
Los compuestos pertenecientes a las familias de los terpenos y de los bencenoides son los más frecuentes en el aceite esencial del ajenjo y son los responsables de su aroma.Compounds belonging to the families of Terpenes and benzenoids are the most frequent in the Absinthe essential oil and are responsible for its aroma.
Existe una alta variabilidad en la composición del aceite esencial de A. absinthium L, que depende de muchos factores como las condiciones de crecimiento, el estado de desarrollo, el momento de la recolección así como la presencia de flores, frutos o raíces. Esta variabilidad intraespecífica detectada en la composición de los aceites es bastante superior a la que presentan otros metabolitos secundarios, por lo que se han utilizado para definir quimiotipos o razas químicas, que algunas veces pueden relacionarse con factores ecológicos o geográficos.There is a high variability in the composition of the essential oil of A. absinthium L , which depends on many factors such as growth conditions, the state of development, the time of collection as well as the presence of flowers, fruits or roots. This intraspecific variability detected in the composition of the oils is much higher than that presented by other secondary metabolites, so they have been used to define chemotypes or chemical races, which can sometimes be related to ecological or geographical factors.
Se han realizado asimismo pruebas de la actividad biológica. La actividad antibacteriana y fungicida del aceite esencial de A. absinthium L. ya era ampliamente conocida. La tuyona (23), el alcanfor (28) y el cineol (29), que son componentes mayoritarios del aceite han demostrado tener actividades antifúngicas y antibacterianas, así como otros monoterpenos presentes en el aceite como borneol (30), \alpha y \beta pineno, terpinenol, linanol (32).Biological activity tests have also been performed. The antibacterial and fungicidal activity of the essential oil of A. absinthium L. It was already widely known. Tuyona (23), camphor (28) and cineole (29), which are major components of the oil have been shown to have antifungal and antibacterial activities, as well as other monoterpenes present in the oil such as borneol (30),? And \ beta pinene, terpinenol, linanol (32).
Desde la antigüedad el ajenjo se ha utilizado contra parásitos intestinales. El extracto de las hojas de A. absinthium L. presenta actividad antimalárica, así como dos homoditerpenos peróxidos que se han aislado de esta planta.Since ancient times wormwood has been used against intestinal parasites. The extract of the leaves of A. absinthium L. It presents antimalarial activity, as well as two peroxide homoditerpenes that have been isolated from this plant.
El aceite esencial tiene actividad acaricida frente a la araña roja e insecticida frente a gorgojos y mosca común. Además se ha utilizado como repelente de pulgas, moscas, mosquitos, polillas y garrapatas. Por otro lado, el extracto también ha resultado tener efectos tóxicos y antialimentarios frente al escarabajo de la patata (Leptinotarsa decemlineata).The essential oil has acaricidal activity against the red spider and insecticide against weevils and common fly. It has also been used as a repellent for fleas, flies, mosquitoes, moths and ticks. On the other hand, the extract has also proved to have toxic and anti-food effects against the potato beetle ( Leptinotarsa decemlineata ).
Cabe destacar el papel ecológico que juega el aceite esencial en las relaciones bióticas con animales y plantas (herbivorismo, polinización, alelopatía). El cineol y el alcanfor, que son compuestos mayoritarios del aceite, están considerados entre los monoterpenos como las toxinas más efectivas capaces de inhibir el crecimiento de plantas y la germinación de semillas.The ecological role played by the essential oil in biotic relationships with animals and plants (herbivorism, pollination, allelopathy). The cineole and camphor, which are major oil compounds, are considered among monoterpenes as the most effective toxins capable of inhibiting Plant growth and seed germination.
Se han llevado a cabo distintos ensayos de actividad biológica para determinar la actividad antiparasitaria, antialimentaria, repelente, fungicida y fitotóxica de los aceites y extractos en las poblaciones y muestras estudiadas.Different tests of biological activity to determine antiparasitic activity, antialimentary, repellent, fungicidal and phytotoxic oils and extracts in the populations and samples studied.
La actividad antiparasitaria de las poblaciones y muestras de ajenjo se ensayó con protozoos Leishmania infantum y Trypanosoma cruzi, así como también se realizaron ensayos para determinar la citotoxicidad inespecífica de las mismas sobre células de mamífero.The antiparasitic activity of the populations and samples of wormwood was tested with Leishmania infantum and Trypanosoma cruzi protozoa, as well as tests to determine the non-specific cytotoxicity of these on mammalian cells.
Los componentes mayoritarios de las muestras de aceite esencial ensayadas (tuyona, acetato de bornilo, crisantenol, cis-epoxiocimeno, 2,6-dimetil-5,7-octadien-2,3-diol), así como de extractos (artemetina y casticina), no han sido descritos anteriormente como antiparasitarios frente a los géneros Leishmania y Trypanosoma. En ensayos con Trypanosoma brucei rhodesiense, la flavona produce efectos sinérgicos aumentando la actividad tripanocida de otras flavonas. Además potencia la actividad antiplasmódica de la artemisinina en Artemisia annua. Todos los compuestos han presentado actividad antimalárica in vitro con parásitos de Plasmodium falciparum. En nuestros ensayos, ninguna de las dos flavonas presentó efectos antiparasitarios con L. infantum y T. cruzi. Por tanto, los efectos antiparasitarios observados para los extractos, pueden ser efecto de la acción sinérgica entre las flavonas y otros compuestos presentes en esas muestras.The major components of the essential oil samples tested (tuyone, bornyl acetate, chrysanthenol, cis-epoxyocimeno, 2,6-dimethyl-5,7-octadien-2,3-diol), as well as extracts (artemetin and casticin ), have not previously been described as antiparasitic against the genera Leishmania and Trypanosoma. In trials with Trypanosoma brucei rhodesiense , flavone produces synergistic effects by increasing the trypanocidal activity of other flavones. It also enhances the antiplasmodic activity of artemisinin in Artemisia annua . All compounds have presented in vitro antimalarial activity with Plasmodium falciparum parasites. In our trials, neither flavone showed antiparasitic effects with L. infantum and T. cruzi . Therefore, the antiparasitic effects observed for the extracts may be the effect of the synergistic action between the flavones and other compounds present in those samples.
Todos los extractos fueron citotóxicos, a una concentración de 1000 \mug/ml, con una viabilidad celular que en ningún caso supera el 9%. Esto puede indicar que la toxicidad observada en los parásitos sea de tipo inespecífico. No se han descrito efectos citotóxicos de componentes mayoritarios de estas muestras con la excepción de la tuyona (con citotoxicidad frente a células Vero), la artemetina y la casticina, que presentan actividad frente a líneas celulares tumorales. Nuestros ensayos han demostrado la actividad citotóxica de estas dos flavonas frente a la línea celular CHO. Por tanto, el efecto citotóxico observado en los extractos puede ser debido a la presencia de estos compuestos, pero no explican la citotoxicidad de los aceites, y puede estar relacionada con la elevada concentración en la que han sido ensayados.All extracts were cytotoxic, at one 1000 µg / ml concentration, with a cell viability that in no case exceeds 9%. This may indicate that the toxicity observed in parasites is of nonspecific type. Not have described cytotoxic effects of major components of these samples with the exception of tuyone (with cytotoxicity against Vero cells), artemetin and casticin, which have activity in front of tumor cell lines. Our trials have shown the cytotoxic activity of these two flavones against the line CHO cell. Therefore, the cytotoxic effect observed in the Extracts may be due to the presence of these compounds, but do not explain the cytotoxicity of oils, and may be related to the high concentration in which they have been rehearsed
La elevada actividad antiparasitaria observada para todas las muestras ensayadas de A. absinthium L, respaldan su uso como antiparasitarios.The high antiparasitic activity observed for all tested samples of A. absinthium L , support its use as antiparasitic.
Se realizaron asimismo ensayos sobre actividad antialimentaria y repelente de insectos con Spodoptera littoralis, Myzus persicae y Rhopalosiphum padi L. sobre los distintos extractos y aceites de las poblaciones de A. absinthium L. Los extractos obtenidos por fluidos supercríticos han resultado ser más activos que los extractos y aceites de las muestras de las que proceden. Esto nos indica que esta metodología es la más adecuada como método de extracción de en el caso de A. absinthium L.Trials on antialimentary and insect repellent activity were also performed with Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi L. on the different extracts and oils of the populations of A. absinthium L. The extracts obtained by supercritical fluids have proved more active than the extracts and oils of the samples from which they come. This indicates that this methodology is the most suitable as an extraction method in the case of A. absinthium L.
Los monoterpenos son compuestos abundantes en la naturaleza que reúnen las características de bajo coste y baja toxicidad, necesarias para ser unos buenos candidatos en la búsqueda de nuevas drogas. Existen monoterpenos puros que han demostrado tener actividad antiparasitaria, e incluso muchos extractos de plantas y aceites esenciales ricos en monoterpenos han resultado activos frente a Plasmodium y Leishmania. Además, monoterpenoides como el espintanol, el piquerol A y el terpinen-4-ol, así como hidroperóxidos derivados del mentano presentan actividad tripanocida frente a Trypanosoma cruzi.Monoterpenes are abundant compounds in nature that have the characteristics of low cost and low toxicity, necessary to be good candidates in the search for new drugs. There are pure monoterpenes that have been shown to have antiparasitic activity, and even many plant extracts and essential oils rich in monoterpenes have been active against Plasmodium and Leishmania. In addition, monoterpenoids such as spintanol, piquerol A and terpinen-4-ol, as well as hydroperoxides derived from mint have trypanocidal activity against Trypanosoma cruzi .
A su vez, los monoterpenos son los componentes mayoritarios de los aceites esenciales en plantas y suelen presentar efectos repelentes. El 1,8-cineol, componente mayoritario del aceite esencial de ajenjo, es repelente y tóxico con la mayoría de los insectos, sin embargo, también presenta una actividad atrayente para algunos insectos, incluyendo las abejas. Presenta actividad acaricida, insecticida e inhibidora del asentamiento de áfidos con Myzus persicae. El linalol es un eficaz repelente frente a Tyrophagus putrescentiae, Culex pipiens, Thrips tabaci e incluso Myzus persicae. El \alpha-terpineol y el mirceno también son repelentes y tóxicos frente a varias especies de ácaros. El \alpha y \beta pineno producen efectos tóxicos sobre insectos. El epi-\alpha-selineno ha sido identificado en secreciones de glándulas de varias especies de termitas con funciones de defensa. Además, el compuesto 2,6-dimetil-5,7-octadien-2,3-diol presenta actividad frente a Spodoptera littoralis.In turn, monoterpenes are the major components of essential oils in plants and usually have repellent effects. 1,8-cineole, a major component of wormwood essential oil, is repellent and toxic with most insects, however, it also has an attractive activity for some insects, including bees. It has acaricidal, insecticidal and inhibiting activity of aphid settlement with Myzus persicae . Linalool is an effective repellent against Tyrophagus putrescentiae, Culex pipiens, Thrips tabaci and even Myzus persicae . Α-terpineol and myrcene are also repellent and toxic against several species of mites. The α and β pinene produce toxic effects on insects. Epi-? -Selineno has been identified in gland secretions of several termite species with defense functions. In addition, the 2,6-dimethyl-5,7-octadien-2,3-diol compound exhibits activity against Spodoptera littoralis .
De la misma forma se han realizado estudios de actividad fungicida. Se han descrito las propiedades antifúngicas de numerosos aceites esenciales, así como de algunos de sus componentes mayoritarios. El ?-cariofileno y el óxido de cariofileno presentan actividad fungistática frente a varias especies de Fusarium, \alpha-terpineol y \alpha-terpinen-4-ol presentan actividad fungicida frente a Aspergillus flavus y el p-cimeno ha sido descrito recientemente como antifúngico frente a F. oxysporum. También se han descrito las propiedades antifúngicas del aceite esencial de una población de A. absinthium L. procedente de Turquía sobre 34 especies de hongos entre los que se encuentran Fusarium solani y Fusarium oxysporum.In the same way, fungicidal activity studies have been carried out. The antifungal properties of numerous essential oils, as well as some of their major components, have been described. ? -Caryophylene and Caryophylene oxide have fungistatic activity against several species of Fusarium ,? -Terpineol and? -Terpinen-4-ol have fungicidal activity against Aspergillus flavus and p-Cimeno has recently been described as antifungal vs. F. oxysporum . The antifungal properties of the essential oil of a population of A. absinthium L have also been described. from Turkey on 34 species of fungi among which are Fusarium solani and Fusarium oxysporum .
También se ha estudiado la actividad fitotóxica germinativa. Los ensayos de actividad fitotóxica se realizaron con semillas de Triticum aestivum (trigo), Hordeum vulgare (cebada) y Latuca sativa (lechuga), en diversas muestras, seleccionadas en función de la cantidad disponible. Además se ha utilizado la juglona, compuesto de conocida actividad alelopática, como control positivo. En los ensayos de germinación con semillas de trigo se han podido observar efectos significativos en el caso de la juglona y del aceite esencial, con unos porcentajes de inhibición de la germinación de 95 y 49% respectivamente. Los efectos sobre la germinación a las 48 horas del ensayo no fueron significativos en ninguno de los casos. En relación a los experimentos llevados a cabo con semillas de cebada no se observó ningún efecto significativo en la germinación durante todo el ensayo.The germinative phytotoxic activity has also been studied. Phytotoxic activity tests were carried out with seeds of Triticum aestivum (wheat), Hordeum vulgare (barley) and Latuca sativa (lettuce), in various samples, selected according to the quantity available. In addition, juglone, composed of known allelopathic activity, has been used as a positive control. In the germination tests with wheat seeds, significant effects have been observed in the case of juglone and essential oil, with germination inhibition rates of 95 and 49% respectively. The effects on germination at 48 hours of the trial were not significant in any of the cases. In relation to the experiments carried out with barley seeds, no significant effect on germination was observed throughout the test.
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| Application Number | Priority Date | Filing Date | Title |
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| ES201031389A ES2378809B1 (en) | 2010-09-16 | 2010-09-16 | PROCEDURE FOR EXTRACTION OF BIOINSECTICIDE DERIVATIVES OF THE PLANT ARTEMISIA ABSINTHIUM L. |
| ES201390029A ES2405210B1 (en) | 2010-09-16 | 2011-09-14 | PROCEDURE FOR EXTRACTION OF BIOINSECTICIDE DERIVATIVES OF THE PLANT ARTEMISIA ABSINTHIUM L. |
| PCT/ES2011/070641 WO2012035187A1 (en) | 2010-09-16 | 2011-09-14 | Method for extracting bioinsecticide derivatives from the plant artemisia absinthium l |
| CO13041759A CO6680690A2 (en) | 2010-09-16 | 2013-03-01 | Extraction procedure of bioinsecticidal derivatives of the plant (artemisia absinthium l.) |
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| ES201390029A Expired - Fee Related ES2405210B1 (en) | 2010-09-16 | 2011-09-14 | PROCEDURE FOR EXTRACTION OF BIOINSECTICIDE DERIVATIVES OF THE PLANT ARTEMISIA ABSINTHIUM L. |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5591435A (en) * | 1991-12-06 | 1997-01-07 | The Research And Development Institute, Inc. | Insecticidal or insect behaviorally active preparations from aromatic plants |
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| US5591435A (en) * | 1991-12-06 | 1997-01-07 | The Research And Development Institute, Inc. | Insecticidal or insect behaviorally active preparations from aromatic plants |
Non-Patent Citations (3)
| Title |
|---|
| 01.05.2009, E. Langa et al. "The evolution of hyssop oil composition in the supercritical extraction curve: Modelling of the oil extraction process" The Journal of Supercritical Fluid (mayo 2009) Vol. 49, N °. 1, páginas 37 - 44; DOI 10.1016/j.supflu.2008.11.022; todo el documento. * |
| 01.06.2009, E. Langa et al. "Supercritical fluid extraction of Spanish sage essential oil: optimization of the process parameters and modelling" The Journal of SupercriticalFluids (junio 2009) Vol. 49, N °. 2, páginas 174 - 181; DOI 10.1016/j.supflu.2008.12.007; todo el documento. * |
| 17.06.2007, S.M. Pourmortazavi et al. "Supercritical fluid extraction in plant essential and volatile oil analysis" Journal of Chromatography A (17 junio 2007) Vol. 1163, N °. 1-2, páginas 2 - 24; DOI 10.1016/j.chroma.2007.06.021; todo el documento. * |
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| ES2405210A1 (en) | 2013-05-30 |
| WO2012035187A1 (en) | 2012-03-22 |
| CO6680690A2 (en) | 2013-05-31 |
| ES2405210B1 (en) | 2014-04-02 |
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