ES2304323B1 - EXTRACT OF THE COUROUPITA GUIANENSIS SHEETS, PROCEDURE OF OBTAINING AND ITS COSMETIC USE AS AN ANTIOXIDANT / ANTIRRADICALARY / UV FILTER. - Google Patents
EXTRACT OF THE COUROUPITA GUIANENSIS SHEETS, PROCEDURE OF OBTAINING AND ITS COSMETIC USE AS AN ANTIOXIDANT / ANTIRRADICALARY / UV FILTER. Download PDFInfo
- Publication number
- ES2304323B1 ES2304323B1 ES200700856A ES200700856A ES2304323B1 ES 2304323 B1 ES2304323 B1 ES 2304323B1 ES 200700856 A ES200700856 A ES 200700856A ES 200700856 A ES200700856 A ES 200700856A ES 2304323 B1 ES2304323 B1 ES 2304323B1
- Authority
- ES
- Spain
- Prior art keywords
- extracts
- couroupita guianensis
- couroupita
- guianensis
- extraction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 240000009027 Couroupita guianensis Species 0.000 title claims abstract description 92
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- 239000002537 cosmetic Substances 0.000 title claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 238000000605 extraction Methods 0.000 claims abstract description 27
- 238000001704 evaporation Methods 0.000 claims abstract description 6
- 230000008020 evaporation Effects 0.000 claims abstract description 6
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- 239000000516 sunscreening agent Substances 0.000 claims abstract description 5
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 55
- 239000007788 liquid Substances 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 235000006708 antioxidants Nutrition 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 claims description 16
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Abstract
Extracto de las hojas de Couroupita guianensis, procedimiento de obtención y su uso cosmético como antioxidante/antirradicalario/filtro UV (ultravioleta). Extractos obtenidos a partir de hojas secas, molidas y tamizadas, extracción con agua, y/o alcoholes, evaporación de este disolvente, posterior extracción con agua y/o glicoles del extracto seco de Couroupita guianensis y filtración; que pueden ser utilizados para el cuidado de la piel y/o el cabello, por ejemplo como antioxidantes o inhibidores de radicales, como agentes para combatir el envejecimiento o protectores solares. Couroupita guianensis leaf extract, procedure for obtaining and its cosmetic use as antioxidant / anti-radical / UV filter (ultraviolet). Extracts obtained from dried, ground and sieved leaves, extraction with water, and / or alcohols, evaporation of this solvent, subsequent extraction with water and / or glycols of the dry extract of Couroupita guianensis and filtration; which can be used for skin and / or hair care, for example as antioxidants or radical inhibitors, as agents to combat aging or sunscreens.
Description
Extracto de las hojas de Couroupita guianensis, procedimiento de obtención y su uso cosmético como antioxidante/antirradicalario/filtro UV. Couroupita guianensis leaf extract, procedure for obtaining and its cosmetic use as antioxidant / anti-radical / UV filter.
La presente invención se engloba dentro del campo técnico de los extractos vegetales, y su obtención para su uso cosmético como antioxidantes, antirradicalarios y filtros UV.The present invention is encompassed within the technical field of plant extracts, and their obtaining for cosmetic use as antioxidants, anti-radicals and filters UV
A principios del siglo XX Mulliken investigó la reactividad fotolumínica demostrando que durante el proceso de peroxidación y fotoexcitación se formaba un estado excitado del oxígeno (oxígeno singlete: ^{1}O^{\bullet}_{2}). El desarrollo de estas investigaciones llevó a la introducción del término de especies reactivas de oxígeno (ERO) y de radicales libres de oxígeno (RLO) en el campo de la biología y a la demostración de que estas especies radicalarias eran las responsables de los efectos tóxicos del oxígeno.At the beginning of the 20th century Mulliken investigated the photoluminic reactivity demonstrating that during the process of peroxidation and photoexcitation formed an excited state of oxygen (singlet oxygen: 1 O 2). The development of these investigations led to the introduction of the term of reactive oxygen (ERO) and free radical species of oxygen (RLO) in the field of biology and to the demonstration that these radical species were responsible for the effects Toxic oxygen.
Por lo tanto, dado que los ERO/RLO son especies que se generan de forma continuada como productos de la utilización celular del O_{2}, en los organismos aerobios se han desarrollado estrategias biológicas para desactivarlos, como el sistema enzimático superóxido dismutasa, glutatión peroxidasa o catalasa.Therefore, since ERO / RLO are species which are generated continuously as utilization products O2 cell, in aerobic organisms have been developed biological strategies to deactivate them, such as the system Enzymatic superoxide dismutase, glutathione peroxidase or catalase
Con frecuencia, estos mecanismos básicos de defensa no son suficientes para eliminar todas las especies radicalarias generadas de forma endógena (respiración celular y otros procesos fisiológicos) o las de origen exógeno (radiaciones, polución ambiental, fármacos, tóxicos) que desde el entorno inciden en el organismo. La pérdida de equilibrio entre el nivel de prooxidación y el tono antioxidante de un órgano o tejido puede producir daño celular y, secundariamente, condicionar la aparición de estados de enfermedad. Se define el estrés oxidativo como la situación de daño celular que resulta cuando la generación y/o incidencia exógena de RLO supera la capacidad de los diferentes mecanismos fisiológicos del organismo para prevenir o interceptar su acumulación.Often, these basic mechanisms of defense are not enough to eliminate all species endogenously generated radicals (cellular respiration and other physiological processes) or those of exogenous origin (radiation, environmental pollution, drugs, toxic) that affect the environment in the organism The loss of balance between the level of prooxidation and the antioxidant tone of an organ or tissue can produce cellular damage and, secondarily, condition the appearance of disease states. Oxidative stress is defined as the cell damage situation that results when the generation and / or exogenous incidence of RLO exceeds the capacity of different physiological mechanisms of the organism to prevent or intercept its accumulation.
Además de los mecanismos de defensa enzimáticos a lo largo de la evolución biológica, los organismos han desarrollado la capacidad de sintetizar moléculas con actividad antioxidante: ubiquinona, glutatión, ceruloplasmina, transferina y ácido úrico en mamíferos; y compuestos como ácido ascórbico (vitamina C), \alpha-tocoferol (vitamina E), \beta-caroteno (pro-vitamina A), diversos flavonoides y otros compuestos fenólicos en el caso de los vegetales. Así, es bien conocida la relación entre el contenido fenólico de los extractos vegetales y su actividad antioxidante [Y. S. Velioglu et al., Journal of Agricultural and Food Chemistry; 1998, 46 (10), 4113-4117].In addition to enzymatic defense mechanisms throughout biological evolution, organisms have developed the ability to synthesize molecules with antioxidant activity: ubiquinone, glutathione, ceruloplasmin, transferin and uric acid in mammals; and compounds such as ascorbic acid (vitamin C),? -tocopherol (vitamin E),? -carotene (pro-vitamin A), various flavonoids and other phenolic compounds in the case of vegetables. Thus, the relationship between the phenolic content of plant extracts and their antioxidant activity is well known [ YS Velioglu et al., Journal of Agricultural and Food Chemistry ; 1998 , 46 (10), 4113-4117 ].
Los antioxidantes naturales además de proteger al organismo del daño producido por los radicales libres, responsables de las enfermedades degenerativas como el cáncer, arterioesclerosis, artritis y procesos neurodegenerativos y de envejecimiento; pueden presentar actividad antibactericida, antivírica, antimutagénica, antiúlcera o anticarlogénica.Natural antioxidants in addition to protecting to the organism from damage caused by free radicals, responsible for degenerative diseases such as cancer, arteriosclerosis, arthritis and neurodegenerative processes and of aging; they may have antibactericidal activity, antiviral, antimutagenic, antiulcer or anticarlogenic.
Además, si los antioxidantes naturales absorben radiación ultravioleta pueden ser empleados como filtros solares [EP0781544B1]. La radiación UV (ultravioleta) puede ser clasificada en UV-C (longitud de onda menor de 280 nm); UV-B (longitud de onda entre 280 nm y 320 nm) y UV-A (longitud de onda entre 320 nm y 400 nm). De estas radiaciones ultravioletas, la más letal es la radiación UV-C, aunque la mayoría de la misma es absorbida por el ozono. Por ello, las que pueden tener mayor influencia sobre la piel son las radiaciones UV-A y UV-B.In addition, if natural antioxidants absorb ultraviolet radiation can be used as sunscreens [EP0781544B1]. UV (ultraviolet) radiation can be classified in UV-C (wavelength less than 280 nm); UV-B (wavelength between 280 nm and 320 nm) and UV-A (wavelength between 320 nm and 400 nm). From these ultraviolet radiation, the most lethal is radiation UV-C, although most of it is absorbed for ozone. Therefore, those that may have the greatest influence on the skin is UV-A radiation and UV-B
Couroupita guianensis (Lecitidaceae) es un árbol original de la alta selva tropical que se extiende desde el Amazonas hasta Venezuela. También se encuentra en Panamá y Costa Rica y en la India y Sri Lanka. Couroupita guianensis (Lecitidaceae ) is an original tree from the high tropical rainforest that extends from the Amazon to Venezuela. It is also found in Panama and Costa Rica and in India and Sri Lanka.
Couroupita guianensis es una planta utilizada en la India para el tratamiento de enfermedades de la piel [a) A. S. R. Anjaneyulu et al., Indian Journal of Chemistry, Section B; 1998, 37B(4), 382-386. b) The useful plants of India; Publications & Information Directorate; CSIR, New Delhi, 1986, 144. c) J. Anjaria et al., Nature Helas, A glossary of selected indigenous medicinal plants of India; SRISTI Innovations, 1997, 23]. Couroupita guianensis is a plant used in India for the treatment of skin diseases [ a) ASR Anjaneyulu et al ., Indian Journal of Chemistry, Section B ; 1998 , 37B (4), 382-386. b) The useful plants of India; Publications & Information Directorate; CSIR, New Delhi , 1986 , 144. c) J. Anjaria et al ., Nature Helas, A glossary of selected indigenous medicinal plants of India; SRISTI Innovations , 1997 , 23 ].
Se ha determinado actividad antimicrobiana, antibacteriana y antibiótica de extractos de hojas, tallos, flores, frutos, raíces y corteza de Couroupita guianensis y actividad antifúngica de extractos de tallos, corteza y flores [a) S. J. Vahanwala et al., Indian Drugs; 2000, 37, 343-345. b) M. R. Khan et al., Journal of herbs, spices & medicinal plants; 2003, 10 (3), 95-108. c) M. Poonkothai et al., Plant Archives; 2005, 5 (1), 93-95].It has been determined antimicrobial, antibacterial and antibiotic activity of extracts of leaves, stems, flowers, fruits, roots and bark of Couroupita guianensis and antifungal activity of extracts of stems, bark and flowers [ a) SJ Vahanwala et al ., Indian Drugs ; 2000 , 37, 343-345. b) MR Khan et al ., Journal of herbs, spices & medicinal plants ; 2003 , 10 (3), 95-108. c) M. Poonkothai et al ., Plant Archives ; 2005 , 5 (1), 93-95 ].
Por otra parte, se ha estudiado la actividad antilarvaria de extractos de flores y frutos de Couroupita guianensis [S. T. Desal et al., Indian Drug; 2003, 40 (8), 484-486].On the other hand, the antilarvaria activity of flower and fruit extracts of Couroupita guianensis [ST Desal et al., Indian Drug ; 2003 , 40 (8), 484-486 ].
Asimismo, se ha determinado la actividad analgésica y antiinflamatoria de extractos de flores y corteza de Couroupita guianensis [M. Geetha et al., Journal: of Natural Remedies; 2004, 4 (1), 52-55].Likewise, the analgesic and anti-inflammatory activity of flowers and bark extracts of Couroupita guianensis [M. Geetha et al., Journal: of Natural Remedies ; 2004 , 4 (1), 52-55 ].
Por otra parte, hay estudios sobre el efecto de extractos de corteza y flores de Couroupita guianensis en el ciclo reproductivo en ratas [M. Geetha et al., Journal of Natural Remedies; 2005, 5 (2), 121-125] y estudios sobre el efecto de extractos de semillas de Couroupita guianensis en la reproducción de peces [G. R. Dave et al., Indian Botanical Contacto; 1991, 8 (3), 99-106].On the other hand, there are studies on the effect of bark and flower extracts of Couroupita guianensis on the reproductive cycle in rats [ M. Geetha et al., Journal of Natural Remedies ; 2005 , 5 (2), 121-125 ] and studies on the effect of Couroupita guianensis seed extracts on fish reproduction [ GR Dave et al., Indian Botanical Contact ; 1991 , 8 (3), 99-106 ].
También, se ha determinado la actividad analgésica y antiinflamatoria de dos extractos, butanólico y acuoso, de las hojas de Couroupita guianensis obtenidos tras un fraccionamiento entre disolventes orgánicos de diferente polaridad (metanol, hexano, diclorometano y acetona) [A. M. Martínez Morán; Estudio químico de la Couroupita guianensis y de la Ilex guayusa y nuevas aplicaciones sintéticas de las 1-(3-feniletil)isoquinolinas y de las 2-bencilidén-1-indanonas: síntesis total de benzofluorenos y de benzofuronaftalenos, Tesis doctoral, 1999].Also, the analgesic and anti-inflammatory activity of two extracts, butanolic and aqueous, of the leaves of Couroupita guianensis obtained after a fractionation between organic solvents of different polarity (methanol, hexane, dichloromethane and acetone) [ AM Martínez Morán; Chemical study of Couroupita guianensis and Ilex guayusa and new synthetic applications of 1- (3-phenylethyl) isoquinolines and 2-benzylidene-1-indanones: total synthesis of benzofluorenes and benzofuronaphthalenes, PhD Thesis , 1999 ].
Por último, hay bastantes estudios de actividad de los alcaloides indólicos, de tipo indolo[2,1-b]quinazolo-6,12-dionas, aislados de los frutos de Couroupita guianensis, y en concreto del tryphantrin y sus derivados. Estos alcaloides presentan actividad antibacteriana, antituberculosa [a) L. A. Mitscher et al, Pure & Applied Chemistry; 1998, 70 (2), 365-371. b) WO951380], antimalárica [US2006160827A1] y actividad antiinflamatoria, por actuar como inhibidores de prostaglandinas y leucotrienos [H. Danz et al., Planta Medica; 2001, 67, 411-416].Finally, there are many studies of the activity of indole alkaloids, of the indole type [2,1- b ] quinazolo-6,12-dionas, isolated from the fruits of Couroupita guianensis , and in particular of tryphantrin and its derivatives. These alkaloids have antibacterial, antituberculous activity [ a) LA Mitscher et al , Pure & Applied Chemistry ; 1998 , 70 (2), 365-371 . b) WO951380], antimalarial [US2006160827A1] and anti-inflammatory activity, acting as inhibitors of prostaglandins and leukotrienes [ H. Danz et al., Planta Medica ; 2001 , 67, 411-416 ].
Hay diversos estudios sobre la composición fitoquímica de Couroupita guianensis.There are several studies on the phytochemical composition of Couroupita guianensis .
Se han aislado de los frutos de Couroupita guianensis los ácidos cítrico, málico e isocítrico [a) E. K. Nelson et al., Journal of the American Chemical Society; 1937, 59, 2499-2500. b) T. R. Soderstrom, American Journal of Botany; 1962, 49(8), 850-855], ácidos clorogénicos [P. V. Pontes et al., Journal of the Science of Food and Agricultura; 2002, 82(10), 1177-1181], los esteroles estigmaesterol y camfesterol; y los alcaloides indólicos tryptanthrina, couropitina A, couropitina B o indirrubina, índigo e isatina [a) J. Bergman et al., Tetrahedron; 1985, 41(14), 2879-2881. b) J. Bergman et al., Tetrahedron Letters; 1977, 30, 2625-2626. c) A. K. Sen et al., Tetrahedron Letters; 1974, 7, 609-610. c) A. L. Dyakonov et al., Chemistry of Natural Compounds; 1997, 33 (3), 221-267].Citrus, malic and isocitric acids have been isolated from the fruits of Couroupita guianensis [ a) EK Nelson et al., Journal of the American Chemical Society ; 1937 , 59, 2499-2500. b) TR Soderstrom, American Journal of Botany ; 1962 , 49 (8), 850-855 ], chlorogenic acids [ PV Pontes et al., Journal of the Science of Food and Agriculture ; 2002 , 82 (10), 1177-1181 ], stigmaesterol and camfesterol sterols; and the tryptanthrine, couropitin A, couropitin B or indirubin, indigo and isatin indol alkaloids [ a) J. Bergman et al., Tetrahedron ; 1985 , 41 (14), 2879-2881. b) J. Bergman et al., Tetrahedron Letters ; 1977 , 30, 2625-2626. c) AK Sen et al., Tetrahedron Letters ; 1974 , 7, 609-610. c) AL Dyakonov et al., Chemistry of Natural Compounds ; 1997 , 33 (3), 221-267 ].
Hay estudios sobre el contenido en ácidos grasos, proteínas, terpenos, esteroles, y aminoácidos de las semillas de Couroupita guianensis. [a) E. H. A. Andrade et al., Journal of Food Composition and Analysis; 1999, 12(1), 37-51. b) R. C. A. Lago et al., Acta Amazónica; 1987, Volume Date 1986, 16-17(1), 369-376. c) G. R. Dave et al., Fette, Seifen, Anstrichmittel; 1985, 87(3), 111-112. d) N. S. Bai, Bull. Central Research Inst. Univ. Travancor, Trivandrum; 1954, 3, 114-117. e) W. N. Zuo et al., Journal of Agricultural and Food Chemistry; 1996, 44(5), 1206-1210].There are studies on the content of fatty acids, proteins, terpenes, sterols, and amino acids of the seeds of Couroupita guianensis. [a) EHA Andrade et al., Journal of Food Composition and Analysis ; 1999 , 12 (1), 37-51. b) RCA Lago et al., Amazon Act ; 1987 , Volume Date 1986 , 16-17 (1), 369-376. c) GR Dave et al., Fette, Seifen, Anstrichmittel ; 1985 , 87 (3), 111-112. d) NS Bai, Bull. Central Research Inst. Univ. Travancor, Trivandrum ; 1954 , 3, 114-117. e) WN Zuo et al., Journal of Agricultural and Food Chemistry ; 1996 , 44 (5), 1206-1210 ].
Se ha determinado la presencia de taninos, de terpenos, esteroides, ketosteroides y esteroles en la composición química de la corteza [a) A. S. R. Anjaneyulu, op. cited (1998). b) L. R. Row et al., Current Science; 1966, 35(6), 146-147].The presence of tannins, terpenes, steroids, ketosteroids and sterols in the chemical composition of the cortex [ a) ASR Anjaneyulu, op. cited ( 1998 ). b) LR Row et al., Current Science ; 1966 , 35 (6), 146-147 ].
Se ha determinado la presencia de antocianinas, flavonoides, ácidos cinámicos y compuestos de naturaleza lipídica, en los estigmas [F. W. Martin, American Journal of Botany; 1969, 56(9), 1023-1027].The presence of anthocyanins, flavonoids, cinnamic acids and compounds of a lipid nature in stigmas has been determined [ FW Martin, American Journal of Botany ; 1969 , 56 (9), 1023-1027 ].
De las flores de Couroupita guianensis se han identificado, entre los componentes volátiles, linalool, eugenol, nerol, geraniol y (E,E)-farnesol [a) E. H. A. Andrade et al., Journal of Essential Oil Research; 2000, 12(2), 163-166. b) K. C. Wong et al., Journal of Essential Oil Research; 1995, 7(2), 225-227. c) Y S. Lewis et al., Perfumery and Essential Oil Record; 1969, 60(1), 23-24. d) J. T. Knudsen et al., Biotropica; 1996, 28, 42-60]. Asimismo, se han aislado de las flores de Couroupita guianensis un hidrocarburo alifático y estigmasterol [J. B. Rane et al., Indian Journal of Pharmaceutical Sciences; 1994, 56, 72-73].Among the flowers of Couroupita guianensis , among the volatile components, linalool, eugenol, nerol, geraniol and (E, E) -farnesol [ a) EHA Andrade et al., Journal of Essential Oil Research ; 2000 , 12 (2), 163-166. b) KC Wong et al., Journal of Essential Oil Research ; 1995 , 7 (2), 225-227. c) And S. Lewis et al., Perfumery and Essential Oil Record ; 1969 , 60 (1), 23-24. d) JT Knudsen et al., Biotropica ; 1996 , 28, 42-60 ]. Likewise, an aliphatic hydrocarbon and stigmasterol have been isolated from Couroupita guianensis flowers [ JB Rane et al., Indian Journal of Pharmaceutical Sciences ; 1994 , 56, 72-73 ].
De las hojas de Couroupita guianensis se han aislado el éster triperpénico \beta-amirin palmitato [A. A. Eknath et al., Indian Drugs; 2002, 39(4), 213-216], el kaemferol-3-O-neohesperidósido, y dos ácidos hidroxicinámicos, el ácido cafeico y un derivado del mismo, el ácido rosmarinico [A. M. Martínez Morán, op. cited (1999)].From the leaves of Couroupita guianensis , the triperpenic ester? -Amirin palmitate [ AA Eknath et al., Indian Drugs ; 2002 , 39 (4), 213-216 ], kaemferol-3- O -neohesperidósido, and two hydroxycinnamic acids, caffeic acid and a derivative thereof, rosmarinic acid [ AM Martínez Morán, op. cited ( 1999 )].
La presente invención describe extractos de las hojas de Couroupita guianensis, su procedimiento de obtención y su uso cosmético como antioxidantes/antirradicalarios/filtros UV (ultravioleta).The present invention describes extracts of Couroupita guianensis leaves, their method of obtaining and their cosmetic use as antioxidants / anti-radical / UV filters (ultraviolet).
Se describe, entre otras cosas, un nuevo procedimiento para la obtención de extractos de Couroupita guianensis a partir de las hojas, que permite emplear disolventes inocuos, como son agua, glicoles y otros alcoholes, de bajo coste y operación segura para obtener un producto estable, fácil de manejar, de adicionar a diferentes productos y que puede ser empleado como ingrediente de la industria cosmética. También describe dichos extractos de Couroupita guianensis, obtenidos por el procedimiento descrito, es decir, los propios extractos de Couroupita guianensis, caracterizados por presentar, entre otros, elevado contenido fenólico y relevantes propiedades antioxidantes, antirradicalarias y de protección UV, que hace que puedan ser utilizados para el cuidado de la piel y/o el cabello, por ejemplo como antioxidantes o inhibidores de radicales, como agentes para combatir el envejecimiento o protectores solares. Los extractos presentan frecuentemente mayor actividad antioxidante que antioxidantes sintéticos como el BHT (butirohidroxitolueno), el BHA (butirohidroxianisol) o Trolox (equivalente soluble del \alpha-tocoferol o vitamina E).It describes, among other things, a new procedure for obtaining extracts of Couroupita guianensis from the leaves, which allows the use of harmless solvents, such as water, glycols and other alcohols, of low cost and safe operation to obtain a stable product , easy to handle, to add to different products and that can be used as an ingredient of the cosmetic industry. It also describes said extracts of Couroupita guianensis , obtained by the described procedure, that is, the extracts of Couroupita guianensis , characterized by presenting, among others, high phenolic content and relevant antioxidant, anti-radical and UV protection properties, which makes them possible to be used for skin and / or hair care, for example as antioxidants or radical inhibitors, as agents to combat aging or sunscreens. The extracts frequently have higher antioxidant activity than synthetic antioxidants such as BHT (butyrohydroxytoluene), BHA (butyrohydroxyanisole) or Trolox (soluble equivalent of α-tocopherol or vitamin E).
La práctica de la presente invención implica:The practice of the present invention it implies:
Se emplean las hojas secas de Couroupita guianensis molidas y tamizadas. Se someten a un molido, preferentemente en un molino de aspas, y se tamiza, preferentemente a tamaño de partícula de 0,6 mm. aproximadamente.The dried leaves of ground and sifted Couroupita guianensis are used . They are subjected to a grind, preferably in a blade mill, and screened, preferably at a particle size of 0.6 mm. approximately.
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Las hojas secas, molidas y tamizadas de Couroupita guianensis se someten a un proceso de extracción sólido-líquido en continuo con disolventes, preferentemente se realiza una extracción por soxhlet.The dried, ground and sieved sheets of Couroupita guianensis are subjected to a continuous solid-liquid extraction process with solvents, preferably an extraction by soxhlet is performed.
Se emplean relaciones líquido:sólido elevadas, preferentemente de 30 g/g.Liquid: high solid ratios are used, preferably 30 g / g.
Como disolvente a extractar se emplean agua y/o disolventes hidroalcohólicos y/o alcohólicos. Se elige ventajosamente alcoholes C_{1} a C_{4} y, preferentemente, etanol o metanol. Entre ellos, se elige ventajosamente una mezcla etanol/agua 1:1.Water and / or solvent are used as solvent to extract hydroalcoholic and / or alcoholic solvents. Is chosen advantageously C 1 to C 4 alcohols and, preferably, ethanol or methanol Among them, a mixture is advantageously chosen 1: 1 ethanol / water.
La temperatura de la extracción es la de reflujo del disolvente o mezcla de disolventes de extracción y está en el rango de 60-120ºC y, preferentemente, entre 85-95ºC.The temperature of the extraction is that of reflux of the solvent or mixture of extraction solvents and is in the range of 60-120 ° C and preferably between 85-95 ° C.
El tiempo de extracción está en el intervalo de 3 horas a 21 días.The extraction time is in the range of 3 hours to 21 days.
El proceso extractivo se realiza protegido de la luz para evitar posibles alteraciones.The extractive process is carried out protected from light to avoid possible alterations.
El rendimiento del proceso extractivo oscila entre el 15% y el 40% (g/g).The performance of the extractive process oscillates between 15% and 40% (g / g).
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Los extractos acuosos, alcohólicos o hidroalcohólicos obtenidos de las hojas de Couroupita guianensis se someten a evaporación a vacío para eliminar el disolvente y obtener los extractos secos de Couroupita guianensis.Aqueous, alcoholic or hydroalcoholic extracts obtained from the leaves of Couroupita guianensis are subjected to vacuum evaporation to remove the solvent and obtain the dried extracts of Couroupita guianensis .
El agua se elimina mediante evaporación a vacío, preferentemente mediante liofilización.Water is removed by evaporation under vacuum, preferably by lyophilization.
Si, para la obtención de los extractos líquidos de la etapa iv), se emplean como disolventes de extracción agua o hidroglicoles, en algún caso puede eliminarse a vacío sólo el disolvente alcohólico de la etapa ii) y no eliminar el agua, obteniéndose extractos acuosos de Couroupita guianensis.If, in order to obtain the liquid extracts of stage iv), water or hydroglycols are used as extraction solvents, in some cases only the alcoholic solvent of stage ii) can be removed under vacuum and the water cannot be removed, obtaining aqueous extracts of Couroupita guianensis .
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Los extractos secos o los extractos acuosos de Couroupita guianensis obtenidos en la etapa iii), se someten a un nuevo proceso extractivo sólido-líquido en continuo con disolventes, preferentemente mediante maceración con agitación.The dried extracts or aqueous extracts of Couroupita guianensis obtained in step iii), are subjected to a new solid-liquid extractive process in continuous with solvents, preferably by maceration with stirring.
Se emplean relaciones líquido:sólido elevadas, preferentemente de 99 g/g.Liquid: high solid ratios are used, preferably 99 g / g.
Como disolvente a extractar se emplea agua y/o disoluciones hidroglicólicas y/o glicólicas. Se elige ventajosamente glicoles C_{2} a C_{6}. Entre estos glicoles se prefiere utilizar propilenglicol y butilenglicol. Entre ellos, se elige ventajosamente una mezcla butilenglicol/agua 1:1.Water and / or solvent is used as solvent to extract hydroglycolic and / or glycolic solutions. Is chosen advantageously C2 to C6 glycols. Among these glycols are prefers to use propylene glycol and butylene glycol. Among them, it advantageously choose a 1: 1 butylene glycol / water mixture.
La temperatura de extracción es la temperatura ambiente, 20ºC aproximadamente.The extraction temperature is the temperature ambient, approximately 20 ° C.
El tiempo de extracción es prolongado, de 3 a 21 días.Extraction time is prolonged, from 3 to 21 days.
El proceso extractivo se realiza protegido de la luz para evitar posibles alteraciones.The extractive process is carried out protected from light to avoid possible alterations.
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Los sólidos de los extractos líquidos de Couroupita guianensis, obtenidos en la etapa iv), se separan por filtración, preferentemente mediante placa porosa del nº 3 ó 4, o papel de filtro de gramaje 73 g/m^{2}, obteniéndose los extractos líquidos filtrados de Couroupita guianensis.The solids of the liquid extracts of Couroupita guianensis , obtained in step iv), are separated by filtration, preferably by porous plate No. 3 or 4, or weight filter paper 73 g / m2, the extracts being obtained filtered liquids of Couroupita guianensis .
Estos extractos se almacenan refrigerados, preferentemente a 4ºC, y protegidos de la luz para evitar posibles alteraciones.These extracts are stored refrigerated, preferably at 4 ° C, and protected from light to avoid possible alterations
La radiación UV (ultravioleta) se clasifica en UV-C (longitud de onda menor de D 280 nm); UV-B (longitud de onda entre 280 nm y 320 nm) y UV-A (longitud de onda entre 320 nm y 400 nm), por ello, si un producto absorbe radiación entre 250 a 400 nm puede ser empleado como filtro solar.UV (ultraviolet) radiation is classified as UV-C (wavelength less than D 280 nm); UV-B (wavelength between 280 nm and 320 nm) and UV-A (wavelength between 320 nm and 400 nm), by this, if a product absorbs radiation between 250 to 400 nm can be Used as sunscreen.
Se mide la absorbancia (Abs) de los extractos líquidos filtrados de Couroupita guianensis, obtenidos según el procedimiento de extracción, a la concentración de 100 ppm en etanol entre las longitudes de onda de 250 a 400 nm frente a un blanco de etanol. Todos presentan máximos de absorción en la región UV (ultravioleta). Así a la longitud de onda de 250 nm presentan Abs > 1,000; a 280 nm presentan Abs > 0,800; a 320 nm presentan Abs > 0,300 y a 400 nm presentan Abs > 0,100.The absorbance (Abs) of the filtered liquid extracts of Couroupita guianensis , obtained according to the extraction procedure, is measured at the concentration of 100 ppm in ethanol between the wavelengths of 250 to 400 nm against an ethanol blank. All have maximum absorption in the UV (ultraviolet) region. Thus at the wavelength of 250 nm they present Abs>1,000; at 280 nm they present Abs>0.800; at 320 nm they present Abs> 0.300 and at 400 nm they present Abs> 0.100.
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Los compuestos fenólicos presentan una elevada actividad antioxidante [Y. S. Velioglu, op. cited (1998)]. Por ello, se determina el contenido fenólico de los extractos líquidos de Couroupita guianensis según el método de Folin Ciocalteu's [A. Escarpa et al., Analytica Chimica Acta; 2001, 427(1), 119-127]. Se mide la absorbancia a 765 nm de una disolución de 0,5 mL del extracto antioxidante, 3,75 mL de agua destilada, 0,25 mL del reactivo de Folin Ciocalteau's (1:1 con agua destilada) y 0,5 mL de Na_{2}CO_{3} al 10%; después de 1 hora a temperatura ambiente, frente a un blanco sin extracto. Se determina el contenido fenólico del extracto comparando la absorbancia con un recta patrón de ácido gálico (0-100 ppm).Phenolic compounds have a high antioxidant activity [ YS Velioglu, op. cited ( 1998 )]. Therefore, the phenolic content of the liquid extracts of Couroupita guianensis is determined according to the method of Folin Ciocalteu's [ A. Escarpa et al., Analytica Chimica Acta ; 2001 , 427 (1), 119-127 ]. The absorbance at 765 nm of a solution of 0.5 mL of the antioxidant extract, 3.75 mL of distilled water, 0.25 mL of Folin Ciocalteau's reagent (1: 1 with distilled water) and 0.5 mL of 10% Na 2 CO 3; after 1 hour at room temperature, against a white without extract. The phenolic content of the extract is determined by comparing the absorbance with a straight gallic acid standard (0-100 ppm).
Los extractos líquidos filtrados de Couroupita guianensis, obtenidos según el procedimiento de extracción, presentan, según el procedimiento descrito, un alto contenido fenólico, entre 25-35%.The filtered liquid extracts of Couroupita guianensis , obtained according to the extraction procedure, have, according to the described procedure, a high phenolic content, between 25-35%.
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Para medir la actividad captadora del radical \alpha,\alpha-difenil-\beta-picrilhidracilo (DPPH^{\bullet}) [I. Parejo et al., Journal of Agricultural and Food Chemistry; 2002, 50, 6882-6890], se mide la disminución de la absorbancia a 515 nm, después de 16 minutos, de una disolución de 2 mL de DPPH^{\bullet} 6 10^{-5} M en metanol y 50 \muL del extracto antioxidante. El porcentaje de inhibición se calcula según la siguiente fórmula:To measure the capture activity of the α, α-diphenyl-β-picrylhydracil (DPPH) radical [ I. Parejo et al., Journal of Agricultural and Food Chemistry ; 2002 , 50, 6882-6890 ], the decrease in absorbance at 515 nm, after 16 minutes, of a solution of 2 mL of DPPH 6 -5 M in methanol and 50 is measured µL of the antioxidant extract. The percentage of inhibition is calculated according to the following formula:
PI (Porcentaje de Inhibición) Pl(%): [(Abs t=0 min-Abs t=16 min)/Abs t=0 min)]*100PI (Percentage of Inhibition) Pl (%): [(Abs t = 0 min-Abs t = 16 min) / Abs t = 0 min)] * 100
Se mide la IC_{50} o concentración que inhibe el 50% del radical DPPH^{\bullet}.The IC 50 or concentration that inhibits is measured 50% of the DPPH radical.
Los extractos líquidos filtrados de Couroupita guianensis, obtenidos según el procedimiento de extracción, presentan una IC_{50} entre 200 a 400 ppm. La IC_{50} del BHA, medida según el mismo procedimiento, es de 240 ppm y la del BHT de 2790 ppm.The filtered liquid extracts of Couroupita guianensis , obtained according to the extraction procedure, have an IC 50 between 200 and 400 ppm. The IC 50 of the BHA, measured according to the same procedure, is 240 ppm and that of the BHT of 2790 ppm.
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Para medir la actividad inhibitoria de la oxidación en medio emulsionado, basada en la inhibición de la oxidación de una emulsión de \beta-caroteno (pro-vitamina A) y ácido linoleico [G. J. Marco, Journal American Oil Chemists' Society; 1968, 45, 594-8], se prepara una disolución de \beta-caroteno (2 mg en 10 mL de cloroformo). Se añade 1 mL de esta disolución en un tubo con 20 mg de ácido linoleico y 200 mg del emulgente Tween 40. Se homogeniza. Se elimina el cloroformo a vacío. Se añaden 50 mL de agua destilada saturada de oxígeno. Se agita a 6000 rpm para formar la emulsión. Se miden las absorbancias a 470 nm de la muestra del extracto antioxidante (200 \muL del extracto en 5 mL de emulsión) y del control (200 \muL de etanol absoluto en 5 mL de emulsión) después de 2 horas a 50ºC. Se hace un blanco siguiendo el mismo procedimiento pero sin añadir \beta-caroteno. Se mide el coeficiente de actividad antioxidante (CAA, %), que es la relación de oxidación del \beta-caroteno en presencia y ausencia de antioxidante.To measure oxidation inhibitory activity in an emulsified medium, based on the oxidation inhibition of an emulsion of β-carotene (pro-vitamin A) and linoleic acid [ GJ Marco, Journal American Oil Chemists'Society; 1968 , 45, 594-8 ], a solution of β-carotene (2 mg in 10 mL of chloroform) is prepared. 1 mL of this solution is added in a tube with 20 mg of linoleic acid and 200 mg of the Tween 40 emulsifier. It is homogenized. Chloroform is removed in vacuo. 50 mL of distilled water saturated with oxygen are added. Stir at 6000 rpm to form the emulsion. The absorbances at 470 nm of the sample of the antioxidant extract (200 µL of the extract in 5 mL of emulsion) and the control (200 µL of absolute ethanol in 5 mL of emulsion) are measured after 2 hours at 50 ° C. A blank is made following the same procedure but without adding β-carotene. The coefficient of antioxidant activity (CAA,%), which is the oxidation ratio of β-carotene in the presence and absence of antioxidant, is measured.
CAA = [(Abs extract 120 min - Abs control 120 min)/(Abs control 0 min - Abs control 120 min)]*100CAA = [(Abs extract 120 min - Abs control 120 min) / (Abs control 0 min - Abs control 120 min)] * 100
Los extractos líquidos filtrados de Couroupita guianensis, obtenidos según el procedimiento de extracción, presentan a 250 ppm de concentración actividad inhibitoria de la oxidación de entre el 35% al 60%. Los valores de CAA para el BHA a 250 ppm, según el mismo procedimiento, fueron de 80%.The filtered liquid extracts of Couroupita guianensis , obtained according to the extraction procedure, have an oxidation inhibitory activity concentration of between 35% and 60% at 250 ppm. The CAA values for the BHA at 250 ppm, according to the same procedure, were 80%.
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Para medir la capacidad de inhibición del radical ABTS^{\bullet +} y determinar su equivalente en Trolox (equivalente soluble de la vitamina E o \alpha-tocoferol) [R. Re et al., Free Radical Biology and Medicine; 1999, 26, 1231-1237], se prepara un tampón de PBS pH 7,4 (8,0 g NaCl, 0,2 g KH_{2}PO_{4} , 1,15 g Na_{2}HPO_{4}, 0,2 g KCl, 0,2 g azida sódica). Se prepara el reactivo de TEAC (38,4 mg ABTS^{\bullet +} 7 mM, 6,62 mg persulfato potásico 2,45 mM en 10 mL de tampón PBS). Se agita durante 16 horas en ausencia de luz. Se lee la absorbancia a 734 nm. Se diluye el reactivo hasta que presente una absorbancia próxima a 0,7. Se añaden 20 \muL del extracto antioxidante a 2 mL del reactivo. Se calienta a 30ºC y se mide la absorbancia 734 nm a los 10 minutos. Se hace un control con etanol y un blanco con el tampón PBS. Se compara la absorbancia con los valores de una recta patrón con Trolox (0,1 a 1 mM en agua destilada).To measure the capacity of inhibition of the ABTS? Radical and determine its equivalent in Trolox (soluble equivalent of vitamin E or? -Tocopherol) [ R. Re et al., Free Radical Biology and Medicine ; 1999 , 26, 1231-1237 ], a PBS buffer pH 7.4 (8.0 g NaCl, 0.2 g KH 2 PO 4, 1.15 g Na 2 HPO 4 is prepared }, 0.2 g KCl, 0.2 g sodium azide). The TEAC reagent (38.4 mg ABTS? 7 mM, 6.62 mg potassium persulfate 2.45 mM in 10 mL PBS buffer) is prepared. It is stirred for 16 hours in the absence of light. The absorbance at 734 nm is read. The reagent is diluted until it has an absorbance close to 0.7. 20 µL of the antioxidant extract is added to 2 mL of the reagent. It is heated to 30 ° C and the absorbance 734 nm is measured at 10 minutes. A control is made with ethanol and a blank with the PBS buffer. The absorbance is compared with the values of a standard line with Trolox (0.1 to 1 mM in distilled water).
Los extractos líquidos filtrados de Couroupita guianensis, obtenidos según el procedimiento de extracción, presentan a una concentración de 100 ppm una capacidad de inhibición del radical ABTS^{\bullet +} equivalente a entre 0,400 a 0,800 mM de Trolox. Esto implica una relación peso/peso del extracto seco de Couroupita guianensis/Trolox de 1/1 a 1/2 (g/g).The filtered liquid extracts of Couroupita guianensis , obtained according to the extraction procedure, have a capacity of inhibition of the ABTS2 + radical equivalent to between 0.400 to 0.800 mM of Trolox at a concentration of 100 ppm. This implies a weight / weight ratio of the dry extract of Couroupita guianensis / Trolox from 1/1 to 1/2 (g / g).
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Se determina el poder reductor del hierro o actividad antioxidante de los extractos líquidos de Couroupita guianensis según el método de Oyaizu [M. Oyaizu, Japanese Journal of Nutrition; 1986, 44, 307-315]. El extracto antioxidante se diluye en etanol, a 1 mL del mismo se le añaden 2,5 mL de tampón fosfato pH 6,6 0,2 M y 2,5 mL de ferrocianuro potásico al 1%. Se incuba a 50ºC durante 20 minutos. Se añaden 2,5 mL de ácido tricloroacético al 10%. Se pipetean 2,5 mL del sobrenadante y se mezclan con 2,5 mL de agua destilada y 0,5 mL de cloruro férrico al 0,1%. Se mide la absorbancia a 700 nm y se comparan los resultados con un a recta patrón de ácido ascórbico o vitamina C (0,1-1 mM).The reducing power of iron or antioxidant activity of liquid extracts of Couroupita guianensis is determined according to the method of Oyaizu [ M. Oyaizu, Japanese Journal of Nutrition ; 1986 , 44, 307-315 ]. The antioxidant extract is diluted in ethanol, 2.5 mL of phosphate buffer pH 0.6 0.2 M and 2.5 mL of 1% potassium ferrocyanide are added to 1 mL thereof. Incubate at 50 ° C for 20 minutes. 2.5 mL of 10% trichloroacetic acid are added. 2.5 mL of the supernatant is pipetted and mixed with 2.5 mL of distilled water and 0.5 mL of 0.1% ferric chloride. The absorbance at 700 nm is measured and the results are compared with a straight standard of ascorbic acid or vitamin C (0.1-1 mM).
Los extractos líquidos filtrados de Couroupita guianensis, obtenidos según el procedimiento de extracción, presentan a una concentración de 100 ppm un poder reductor del hierro de entre el 20% al 40% y una equivalencia entre 0,200 mM a 0,400 mM en ácido ascórbico o vitamina C. Esto implica una relación peso/peso del extracto seco de Couroupita guianensis/ácido ascórbico o vitamina C entre 1/0,35 a 1/0,70 (g/g).The filtered liquid extracts of Couroupita guianensis , obtained according to the extraction procedure, have at a concentration of 100 ppm an iron reducing power of between 20% to 40% and an equivalence between 0.200 mM to 0.400 mM in ascorbic acid or vitamin C This implies a weight / weight ratio of the dry extract of Couroupita guianensis / ascorbic acid or vitamin C between 1 / 0.35 to 1 / 0.70 (g / g).
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Las hojas secas de Couroupita guianensis, molidas y tamizadas a tamaño de partícula de 0,6 mm aproximadamente, se someten a un proceso extractivo sólido-líquido en continuo, con una relación líquido:sólido de 30 g/g, mediante un soxhlet, con una mezcla etanol/agua 1:1, a la temperatura de reflujo del disolvente (85-95ºC), durante 12 días y protegido de la luz. Se evapora hasta sequedad, a vacío, el disolvente del extracto obtenido. El rendimiento de la extracción es del 36% (g/g).The dried leaves of Couroupita guianensis , ground and sieved at a particle size of approximately 0.6 mm, are subjected to a continuous solid-liquid extractive process, with a liquid: solid ratio of 30 g / g, using a soxhlet, with a 1: 1 ethanol / water mixture, at the reflux temperature of the solvent (85-95 ° C), for 12 days and protected from light. The solvent of the extract obtained is evaporated to dryness in vacuo. The yield of extraction is 36% (g / g).
El extracto seco de Couroupita guianensis obtenido se somete a un nuevo proceso extractivo sólido-líquido en continuo, mediante maceración con agitación, con una relación liquido:sólido de 99 g/g, a temperatura ambiente y protegido de la luz, durante 16 días con una mezcla butilenglicol/agua 1:1. El extracto líquido de Couroupita guianensis obtenido se filtra, mediante placa porosa del nº 3, y el producto final, el extracto líquido filtrado de Couroupita guianensis, se almacena refrigerado a 4ºC y protegido de la luz para evitar su alteración.The dried extract of Couroupita guianensis obtained is subjected to a new continuous solid-liquid extractive process, by maceration with stirring, with a liquid ratio: 99 g / g solid, at room temperature and protected from light, for 16 days with a 1: 1 butylene glycol / water mixture. The liquid extract of Couroupita guianensis obtained is filtered, using a porous plate of No. 3, and the final product, the filtered liquid extract of Couroupita guianensis , is stored refrigerated at 4 ° C and protected from light to prevent its alteration.
- Se midió la absorbancia de este extracto a la concentración de 100 ppm en etanol a las longitudes de onda de 250 nm (Abs = 1,234), 280 nm (Abs = 1,005), 320 nm (Abs = 0,380) y 400 nm (Abs = 0,145) frente a un blanco de etanol.- The absorbance of this extract was measured at concentration of 100 ppm in ethanol at wavelengths of 250 nm (Abs = 1,234), 280 nm (Abs = 1,005), 320 nm (Abs = 0,380) and 400 nm (Abs = 0.145) against an ethanol blank.
- Contenido fenólico según el método de Folin Ciocalteu's [A. Escarpa, op. cited (2001)]. Se mide la absorbancia a 765 nm de una disolución de 0,5 mL del extracto antioxidante, 3,75 mL de agua destilada, 0,25 mL del reactivo de Folin Ciocalteau's (1:1 con agua destilada) y 0,5 mL de Na_{2}CO_{3} al 10%; después de 1 hora a temperatura ambiente, frente a un blanco sin extracto. Se determina el contenido fenólico del extracto comparando la absorbancia con un recta patrón de ácido gálico (0-100 ppm).- Phenolic content according to the method of Folin Ciocalteu's [ A. Escarpa, op. cited ( 2001 )]. The absorbance at 765 nm of a solution of 0.5 mL of the antioxidant extract, 3.75 mL of distilled water, 0.25 mL of Folin Ciocalteau's reagent (1: 1 with distilled water) and 0.5 mL of 10% Na 2 CO 3; after 1 hour at room temperature, against a white without extract. The phenolic content of the extract is determined by comparing the absorbance with a straight gallic acid standard (0-100 ppm).
El extracto obtenido según el procedimiento descrito en este ejemplo 1 presenta un contenido fenólico del 32%.The extract obtained according to the procedure described in this example 1 has a phenolic content of 32%
- Actividad captadora del radical \alpha,\alpha-difenil-\beta-picrilhidracilo (DPPH^{\bullet}) [I. Parejo, op. cited (2002)]. Se mide la disminución de la absorbancia a 515 nm, después de 16 minutos, de una disolución de 2 mL de DPPH^{\bullet} 6 10^{-5} M en metanol y 50 \muL del extracto antioxidante. El porcentaje de inhibición se calcula según la siguiente fórmula:- Activity of the radical α, α-diphenyl-β-picrylhydracil (DPPH?) [ I. Parejo, op. cited ( 2002 )]. The decrease in absorbance at 515 nm, after 16 minutes, of a solution of 2 mL of 10-5-5M DPPH 6 in methanol and 50 µL of the antioxidant extract is measured. The percentage of inhibition is calculated according to the following formula:
PI (Porcentaje de Inhibición) Pl(%): [(Abs t=0 min-Abs t=16 min)/Abs t=0 min)]*100PI (Percentage of Inhibition) Pl (%): [(Abs t = 0 min-Abs t = 16 min) / Abs t = 0 min)] * 100
Se midió la IC_{50} o concentración que inhibe el 50% del radical DPPH^{\bullet}.IC50 or concentration that inhibits was measured 50% of the DPPH radical.
El extracto obtenido según el procedimiento descrito en este ejemplo 1 presenta una IC_{50} = 205 ppm. La actividad inhibitoria del BHA, medida según el mismo procedimiento, es menor, pues presenta una IC_{50} = 240 ppm, al igual que la del BHT con una IC_{50} = 2790 ppm.The extract obtained according to the procedure described in this example 1 has an IC 50 = 205 ppm. The BHA inhibitory activity, measured according to the same procedure, it is lower, since it has an IC 50 = 240 ppm, as well as the BHT with an IC 50 = 2790 ppm.
- Actividad inhibitoria de la oxidación en medio emulsionado, basada en la inhibición de la oxidación de una emulsión de \beta-caroteno (pro-vitamina A) y ácido linoleico [G. J. Marco, op. cited (1968)]. Se prepara una disolución de \beta-caroteno (2 mg en 10 mL de cloroformo). Se añade 1 mL de esta disolución en un tubo con 20 mg de ácido linoleico y 200 mg del emulgente Tween 40. Se homogeniza. Se elimina el cloroformo a vacío. Se añaden 50 mL de agua destilada saturada de oxígeno. Se agita a 6000 rpm para formar la emulsión. Se miden las absorbancias a 470 nm de la muestra del extracto antioxidante (200 \muL del extracto en 5 mL de emulsión) y del control (200 \muL de etanol absoluto en 5 mL de emulsión) después de 2 horas a 50ºC. Se hace un blanco siguiendo el mismo procedimiento pero sin añadir \beta-caroteno. Se mide el coeficiente de actividad antioxidante (CAA, %), que es la relación de oxidación del \beta-caroteno, o pro-vitamina A, en presencia y ausencia de antioxidante.- Oxidation inhibitory activity in an emulsified medium, based on the oxidation inhibition of an emulsion of β-carotene (pro-vitamin A) and linoleic acid [ GJ Marco, op. cited ( 1968 )]. A solution of β-carotene (2 mg in 10 mL of chloroform) is prepared. 1 mL of this solution is added in a tube with 20 mg of linoleic acid and 200 mg of the Tween 40 emulsifier. It is homogenized. Chloroform is removed in vacuo. 50 mL of distilled water saturated with oxygen are added. Stir at 6000 rpm to form the emulsion. The absorbances at 470 nm of the sample of the antioxidant extract (200 µL of the extract in 5 mL of emulsion) and the control (200 µL of absolute ethanol in 5 mL of emulsion) are measured after 2 hours at 50 ° C. A blank is made following the same procedure but without adding β-carotene. The coefficient of antioxidant activity (CAA,%), which is the oxidation ratio of β-carotene, or pro-vitamin A, in the presence and absence of antioxidant is measured.
CAA = [(Abs extract 120 min - Abs control 120 min)/(Abs control 0 min - Abs control 120 min)]*100CAA = [(Abs extract 120 min - Abs control 120 min) / (Abs control 0 min - Abs control 120 min)] * 100
El extracto obtenido según el procedimiento descrito en este ejemplo 1 presenta a 250 ppm de concentración un CAA de 58%. Los valores de CAA para el BHA a 250 ppm, según el mismo procedimiento, fueron de 80%.The extract obtained according to the procedure described in this example 1 has a concentration of 250 ppm CAA of 58%. The CAA values for the BHA at 250 ppm, according to the same procedure, were 80%.
- Actividad capacidad de inhibición del radical ABTS^{\bullet +} y determinación de su equivalente en Trolox (equivalente soluble de la vitamina E) [R. Re, op. cited (1999)]. Se prepara un tampón de PBS pH 7,4 (8,0 g NaCl, 0,2 g KH_{2}PO_{4}, 1,15 g Na_{2}HPO_{4}, 0,2 g KCl, 0,2 g azida sódica). Se prepara el reactivo TEAC (38,4 mg ABTS^{\bullet +} 7 mM, 6,62 mg persulfato potásico 2,45 mM en 10 mL de tampón PBS). Se agita durante 16 horas en ausencia de luz. Se lee la absorbancia a 734 nm. Se diluye el reactivo hasta que presente una absorbancia próxima a 0,7. Se añaden 20 \muL del extracto antioxidante a 2 mL del reactivo. Se calienta a 30ºC y se mide la absorbancia 734 nm a los 10 minutos. Se hace un control con etanol y un blanco con el tampón PBS. Se compara la absorbancia con los valores de una recta patrón con Trolox (0,1 a 1 mM en agua destilada).- Activity capacity of inhibition of the radical ABTS + and determination of its equivalent in Trolox (soluble equivalent of vitamin E) [ R. Re, op. cited ( 1999 )]. A PBS buffer pH 7.4 (8.0 g NaCl, 0.2 g KH 2 PO 4, 1.15 g Na 2 HPO 4, 0.2 g KCl, 0 is prepared , 2 g sodium azide). The TEAC reagent (38.4 mg ABTS? 7 mM, 6.62 mg potassium persulfate 2.45 mM in 10 mL PBS buffer) is prepared. It is stirred for 16 hours in the absence of light. The absorbance at 734 nm is read. The reagent is diluted until it has an absorbance close to 0.7. 20 µL of the antioxidant extract is added to 2 mL of the reagent. It is heated to 30 ° C and the absorbance 734 nm is measured at 10 minutes. A control is made with ethanol and a blank with the PBS buffer. The absorbance is compared with the values of a standard line with Trolox (0.1 to 1 mM in distilled water).
El extracto obtenido según el procedimiento descrito en este ejemplo 1 presenta a 100 ppm de concentración una equivalencia de 0,733 mM en Trolox. Esto implica una relación peso/peso del extracto seco de Couroupita guianensis/Trolox de 1/1,84 (g/g).The extract obtained according to the procedure described in this example 1 has an equivalent of 0.733 mM in Trolox at 100 ppm concentration. This implies a weight / weight ratio of the dry extract of Couroupita guianensis / Trolox of 1 / 1.84 (g / g).
- Poder reductor del hierro o actividad antioxidante según el método de Oyaizu y determinación de su equivalencia en ácido ascórbico o vitamina C [M. Oyaizu, op. cited (1986)]. El extracto antioxidante se diluye en etanol, a 1 mL del mismo se le añaden 2,5 mL de tampón fosfato pH 6,6 0,2 M y 2,5 mL de ferrocianuro potásico al 1%. Se incuba a 50ºC durante 20 minutos. Se añaden 2,5 mL de ácido tricloroacético al 10%. Se pipetean 2,5 mL del sobrenadante y se mezclan con 2,5 mL de agua destilada y 0,5 mL de cloruro férrico al 0,1%. Se mide la absorbancia a 700 nm y se comparan los resultados con un a recta patrón de ácido ascórbico o vitamina C (0,1-1 mM).- Reducing power of iron or antioxidant activity according to the Oyaizu method and determination of its equivalence in ascorbic acid or vitamin C [ M. Oyaizu, op. cited ( 1986 )]. The antioxidant extract is diluted in ethanol, 2.5 mL of phosphate buffer pH 0.6 0.2 M and 2.5 mL of 1% potassium ferrocyanide are added to 1 mL thereof. Incubate at 50 ° C for 20 minutes. 2.5 mL of 10% trichloroacetic acid are added. 2.5 mL of the supernatant is pipetted and mixed with 2.5 mL of distilled water and 0.5 mL of 0.1% ferric chloride. The absorbance at 700 nm is measured and the results are compared with a straight standard of ascorbic acid or vitamin C (0.1-1 mM).
El extracto obtenido según el procedimiento descrito en este ejemplo 1 presenta a 100 ppm un 32% de poder reductor que equivale a 0,316 mM en ácido ascórbico o vitamina C. Esto implica una relación peso/peso del extracto seco de Couroupita guianensis/ácido ascórbico o vitamina C de 1/0,56 (g/g).The extract obtained according to the procedure described in this example 1 has at 32 ppm a 32% reducing power equivalent to 0.316 mM in ascorbic acid or vitamin C. This implies a weight / weight ratio of the dry extract of Couroupita guianensis / ascorbic acid or Vitamin C of 1 / 0.56 (g / g).
Las hojas secas de Couroupita guianensis, molidas y tamizadas a tamafio de partícula de 0,6 mm aproximadamente, se someten a un proceso extractivo sólido-líquido en continuo, con una relación líquido:sólido de 30 g/g, mediante un soxhlet, con una mezcla etanol/agua 1:1, a la temperatura de reflujo del disolvente (85-95ºC), durante 12 días y protegido de la luz. Se evapora hasta sequedad, a vacío, el disolvente del extracto obtenido. El rendimiento de la extracción es del 36% (g/g).The dried leaves of Couroupita guianensis , ground and sieved at a particle size of approximately 0.6 mm, are subjected to a continuous solid-liquid extractive process, with a liquid: solid ratio of 30 g / g, by means of a soxhlet, with a 1: 1 ethanol / water mixture, at the reflux temperature of the solvent (85-95 ° C), for 12 days and protected from light. The solvent of the extract obtained is evaporated to dryness in vacuo. The yield of extraction is 36% (g / g).
El extracto seco de Couroupita guianensis obtenido se somete a un nuevo proceso extractivo sólido-líquido en continuo, mediante maceración con agitación, con una relación líquido:sólido de 99 g/g, a temperatura ambiente y protegido de la luz, durante 16 días con una mezcla propilenglicol/agua 1:1. El extracto líquido de Couroupita guianensis obtenido se filtra, mediante placa porosa del nº 3, y el producto final, el extracto líquido filtrado de Couroupita guianensis, se almacena refrigerado a 4ºC y protegido de la luz para evitar su alteración.The dried extract of Couroupita guianensis obtained is subjected to a new continuous solid-liquid extractive process, by maceration with stirring, with a liquid ratio: 99 g / g solid, at room temperature and protected from light, for 16 days with a 1: 1 propylene glycol / water mixture. The liquid extract of Couroupita guianensis obtained is filtered, using a porous plate of No. 3, and the final product, the filtered liquid extract of Couroupita guianensis , is stored refrigerated at 4 ° C and protected from light to prevent its alteration.
- Se midió la absorbancia de este extracto a la concentración de 100 ppm en etanol a las longitudes de onda de 250 nm (Abs = 1,049), 280 nm (Abs = 0,806), 320 nm (Abs = 0,377) y 400 nm (Abs = 0,154) frente a un blanco de etanol.- The absorbance of this extract was measured at concentration of 100 ppm in ethanol at wavelengths of 250 nm (Abs = 1,049), 280 nm (Abs = 0.806), 320 nm (Abs = 0.377) and 400 nm (Abs = 0.154) against an ethanol blank.
- Contenido fenólico según el método de Folin Ciocalteu's [A. Escarpa, op. cited (2001)]. Se mide la absorbancia a 765 nm de una disolución de 0,5 mL del extracto antioxidante, 3,75 mL de agua destilada, 0,25 mL del reactivo de Folin Ciocalteau's (1:1 con agua destilada) y 0,5 mL de Na_{2}CO_{3} al 10%; después de 1 hora a temperatura ambiente, frente a un blanco sin extracto. Se determina el contenido fenólico del extracto comparando la absorbancia con un recta patrón de ácido gálico (0-100 ppm).- Phenolic content according to the method of Folin Ciocalteu's [ A. Escarpa, op. cited ( 2001 )]. The absorbance at 765 nm of a solution of 0.5 mL of the antioxidant extract, 3.75 mL of distilled water, 0.25 mL of Folin Ciocalteau's reagent (1: 1 with distilled water) and 0.5 mL of 10% Na 2 CO 3; after 1 hour at room temperature, against a white without extract. The phenolic content of the extract is determined by comparing the absorbance with a straight gallic acid standard (0-100 ppm).
El extracto obtenido según el procedimiento descrito en este ejemplo 2 presenta un contenido fenólico del 26%.The extract obtained according to the procedure described in this example 2 has a phenolic content of 26%
- Actividad captadora del radical \alpha,\alpha-difenil-\beta-picrilhidracilo (DPPH^{\bullet}) [I. Parejo, op. cited (2002)]. Se mide la disminución de la absorbancia a 515 nm después de 16 minutos de una disolución de 2 mL de DPPH^{\bullet} 6 10^{-5} M en metanol y 50 \muL del extracto antioxidante. El porcentaje de inhibición se calcula según la siguiente fórmula:- Activity of the radical α, α-diphenyl-β-picrylhydracil (DPPH?) [ I. Parejo, op. cited ( 2002 )]. The decrease in absorbance at 515 nm is measured after 16 minutes of a 2 mL solution of 10-5-5M DPPH? 6 in methanol and 50 µL of the antioxidant extract. The percentage of inhibition is calculated according to the following formula:
PI (Porcentaje de Inhibición) Pl(%): [(Abs t=0 min-Abs t=16 min)/Abs t=0 min)]*100PI (Percentage of Inhibition) Pl (%): [(Abs t = 0 min-Abs t = 16 min) / Abs t = 0 min)] * 100
Se midió la IC_{50} o concentración que inhibe el 50% del radical DPPH^{\bullet}.IC50 or concentration that inhibits was measured 50% of the DPPH radical.
El extracto obtenido según el procedimiento descrito en este ejemplo 2 presenta una IC_{50} = 327 ppm. La actividad inhibitoria del BHA, medida según el mismo procedimiento, es mayor pues presenta una IC_{50} = 240 ppm, y la del BHT, con IC_{50} = 2790 ppm, menor.The extract obtained according to the procedure described in this example 2 has an IC 50 = 327 ppm. The BHA inhibitory activity, measured according to the same procedure, it is higher because it has an IC 50 = 240 ppm, and that of the BHT, with IC 50 = 2790 ppm, lower.
- Actividad inhibitoria de la oxidación en medio emulsionado, basada en la inhibición de la oxidación de una emulsión de \beta-caroteno y ácido linoleico [G. J. Marco, op. cited (1968)]. Se prepara una disolución de \beta-caroteno (2 mg en 10 mL de cloroformo). Se añade 1 mL de esta disolución en un tubo con 20 mg de ácido linoleico y 200 mg del emulgente Tween 40. Se homogeniza. Se elimina el cloroformo a vacío. Se añaden 50 mL de agua destilada saturada de oxígeno. Se agita a 6000 rpm para formar la emulsión. Se miden las absorbancias a 470 nm de la muestra del extracto antioxidante (200 \muL del extracto en 5 mL de emulsión) y del control (200 \muL de etanol absoluto en 5 mL de emulsión) después de 2 horas a 50ºC. Se hace un blanco siguiendo el mismo procedimiento pero sin añadir \beta-caroteno. Se mide el coeficiente de actividad antioxidante (CAA, %), que es la relación de oxidación del \beta-caroteno en presencia y ausencia de antioxidante.- Oxidation inhibitory activity in emulsified medium, based on the oxidation inhibition of an emulsion of β-carotene and linoleic acid [ GJ Marco, op. cited ( 1968 )]. A solution of β-carotene (2 mg in 10 mL of chloroform) is prepared. 1 mL of this solution is added in a tube with 20 mg of linoleic acid and 200 mg of the Tween 40 emulsifier. It is homogenized. Chloroform is removed in vacuo. 50 mL of distilled water saturated with oxygen are added. Stir at 6000 rpm to form the emulsion. The absorbances at 470 nm of the sample of the antioxidant extract (200 µL of the extract in 5 mL of emulsion) and the control (200 µL of absolute ethanol in 5 mL of emulsion) are measured after 2 hours at 50 ° C. A blank is made following the same procedure but without adding β-carotene. The coefficient of antioxidant activity (CAA,%), which is the oxidation ratio of β-carotene in the presence and absence of antioxidant, is measured.
CAA = [(Abs extract 120 min - Abs control 120 min)/(Abs control 0 min - Abs control 120 min)]*100CAA = [(Abs extract 120 min - Abs control 120 min) / (Abs control 0 min - Abs control 120 min)] * 100
El extracto obtenido según el procedimiento descrito en este ejemplo 2 presenta a 250 ppm de concentración un CAA del 40%. Los valores de CAA para el BHA a 250 ppm, según el mismo procedimiento, fueron de 80%.The extract obtained according to the procedure described in this example 2 has a concentration of 250 ppm CAA of 40%. The CAA values for the BHA at 250 ppm, according to the same procedure, were 80%.
- Actividad capacidad de inhibición del radical ABTS^{\bullet +} y determinación de su equivalente en Trolox (equivalente soluble de la vitamina E) [R. Re, op. cited (1999)]. Se prepara un tampón de PBS pH 7,4 (8,0 g NaCl, 0,2 g KH_{2}PO_{4}, 1,15 g Na_{2}HPO_{4}, 0,2 g KCl, 0,2 g azida sódica). Se prepara el reactivo TEAC (38,4 mg ABTS^{\bullet +} 7 mM, 6,62 mg persulfato potásico 2,45 mM en 10 mL de tampón PBS). Se agita durante 16 horas en ausencia de luz. Se lee la absorbancia a 734 nm. Se diluye el reactivo hasta que presente una absorbancia próxima a 0,7. Se añaden 20 \muL del extracto antioxidante a 2 mL del reactivo. Se calienta a 30ºC y se mide la absorbancia 734 nm a los 10 minutos. Se hace un control con etanol y un blanco con el tampón PBS. Se compara la absorbancia con los valores de una recta patrón con Trolox (0,1 a 1 mM en agua destilada).- Activity capacity of inhibition of the radical ABTS + and determination of its equivalent in Trolox (soluble equivalent of vitamin E) [ R. Re, op. cited ( 1999 )]. A PBS buffer pH 7.4 (8.0 g NaCl, 0.2 g KH 2 PO 4, 1.15 g Na 2 HPO 4, 0.2 g KCl, 0 is prepared , 2 g sodium azide). The TEAC reagent (38.4 mg ABTS? 7 mM, 6.62 mg potassium persulfate 2.45 mM in 10 mL PBS buffer) is prepared. It is stirred for 16 hours in the absence of light. The absorbance at 734 nm is read. The reagent is diluted until it has an absorbance close to 0.7. 20 µL of the antioxidant extract is added to 2 mL of the reagent. It is heated to 30 ° C and the absorbance 734 nm is measured at 10 minutes. A control is made with ethanol and a blank with the PBS buffer. The absorbance is compared with the values of a standard line with Trolox (0.1 to 1 mM in distilled water).
El extracto obtenido según el procedimiento descrito en este ejemplo 2 presenta a 100 ppm de concentración una equivalencia de 0,525 mM en Trolox. Esto implica una relación peso/peso del extracto seco de Couroupita guianensis/Trolox de 1/1,32 (g/g).The extract obtained according to the procedure described in this example 2 has an equivalence of 0.525 mM in Trolox at 100 ppm concentration. This implies a weight / weight ratio of the dry extract of Couroupita guianensis / Trolox of 1 / 1.32 (g / g).
- Poder reductor del hierro o actividad antioxidante según el método de Oyaizu [M. Oyaizu, op. cited (1986)]. El extracto antioxidante se diluye en etanol, a 1 mL del mismo se le añaden 2,5 mL de tampón fosfato pH 6,6 0,2 M y 2,5 mL de ferrocianuro potásico al 1%. Se incuba a 50ºC durante 20 minutos. Se añaden 2,5 mL de ácido tricloroacético al 10%. Se pipetean 2,5 mL del sobrenadante y se mezclan con 2,5 mL de agua destilada y 0,5 mL de cloruro férrico al 0,1%. Se mide la absorbancia a 700 nm y se comparan los resultados con un a recta patrón de ácido ascórbico o vitamina C (0,1-1 mM).- Reducing power of iron or antioxidant activity according to the method of Oyaizu [ M. Oyaizu, op. cited ( 1986 )]. The antioxidant extract is diluted in ethanol, 2.5 mL of phosphate buffer pH 0.6 0.2 M and 2.5 mL of 1% potassium ferrocyanide are added to 1 mL thereof. Incubate at 50 ° C for 20 minutes. 2.5 mL of 10% trichloroacetic acid are added. 2.5 mL of the supernatant is pipetted and mixed with 2.5 mL of distilled water and 0.5 mL of 0.1% ferric chloride. The absorbance at 700 nm is measured and the results are compared with a straight standard of ascorbic acid or vitamin C (0.1-1 mM).
El extracto obtenido según el procedimiento descrito en este ejemplo 2 presenta a 100 ppm un 23% de poder reductor que equivale a 0,316 mM en ácido ascórbico o vitamina C. Esto implica una relación peso/peso del extracto seco de Couroupita guianensis/ácido ascórbico o vitamina C de 1/0,40 (g/g).The extract obtained according to the procedure described in this example 2 has at 100 ppm a 23% reducing power equivalent to 0.316 mM in ascorbic acid or vitamin C. This implies a weight / weight ratio of the dry extract of Couroupita guianensis / ascorbic acid or Vitamin C of 1 / 0.40 (g / g).
Claims (16)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200700856A ES2304323B1 (en) | 2007-03-30 | 2007-03-30 | EXTRACT OF THE COUROUPITA GUIANENSIS SHEETS, PROCEDURE OF OBTAINING AND ITS COSMETIC USE AS AN ANTIOXIDANT / ANTIRRADICALARY / UV FILTER. |
| PCT/ES2008/000178 WO2008119852A1 (en) | 2007-03-30 | 2008-03-27 | Extract of the leaves of couroupita guianensis, method for obtaining same and cosmetic use thereof as an antioxidant/antirradical/uv filter |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200700856A ES2304323B1 (en) | 2007-03-30 | 2007-03-30 | EXTRACT OF THE COUROUPITA GUIANENSIS SHEETS, PROCEDURE OF OBTAINING AND ITS COSMETIC USE AS AN ANTIOXIDANT / ANTIRRADICALARY / UV FILTER. |
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| ES2304323A1 ES2304323A1 (en) | 2008-10-01 |
| ES2304323B1 true ES2304323B1 (en) | 2009-08-13 |
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| KR102180876B1 (en) * | 2018-05-17 | 2020-11-20 | 경남과학기술대학교 산학협력단 | Novel use of Couroupita guianensis |
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Non-Patent Citations (4)
| Title |
|---|
| DESAI, S. T. et al. "{}Larvicidal property of Couroupita guianensis Aubl."{}. Indian Drugs, 2003. Vol. 40, n$^{o}$ 8, páginas 484-486. ISSN 0019-462X. * |
| EKNATH, A. A. et al. "{}Beta amyrin palmitate - Isolation from Couroupita guianensis Aubl. leaves"{}. Indian Drugs, 2002. Vol. 39, n$^{o}$ 4, páginas 213-216. ISSN 0019-462X. Ver página 213 columna 2. * |
| GHEETA, M. et al. "{}Analgesic and anti-inflammatory activity of Couroupita guianensis Aubl."{}. Journal of Natural Remedies, 2004. Vol 4, n$^{o}$ 1, páginas 52-55. * |
| KHAN, M. R. et al. "{}Antibiotic activity of Couroupita guianensis"{}. Journal of Herbs, Spices and Medical Plants, 2003. Vol. 10, n$^{o}$ 3, páginas 95-108. ISSN 1049-6475. Ver página 96. * |
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| WO2008119852A1 (en) | 2008-10-09 |
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