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WO2008119852A1 - Extrait des feuilles de couroupita guianensis, procédé d'obtention et utilisation cosmétique de cet extrait en tant qu'antioxydant/antiradicalaire/filtre uv - Google Patents

Extrait des feuilles de couroupita guianensis, procédé d'obtention et utilisation cosmétique de cet extrait en tant qu'antioxydant/antiradicalaire/filtre uv Download PDF

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Publication number
WO2008119852A1
WO2008119852A1 PCT/ES2008/000178 ES2008000178W WO2008119852A1 WO 2008119852 A1 WO2008119852 A1 WO 2008119852A1 ES 2008000178 W ES2008000178 W ES 2008000178W WO 2008119852 A1 WO2008119852 A1 WO 2008119852A1
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Prior art keywords
guianensis
extracts
couropita
extraction
abs
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English (en)
Spanish (es)
Inventor
Ana María MARTÍNEZ MORÁN
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Caroi'line Cosmetica Sl
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Caroi'line Cosmetica Sl
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Publication of WO2008119852A1 publication Critical patent/WO2008119852A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • Oxidative stress is defined as the situation of cellular damage that results when the generation and / or exogenous incidence of RLO exceeds the capacity of the different physiological mechanisms of the organism to prevent or intercept its accumulation.
  • Natural antioxidants in addition to protecting the body from damage caused by free radicals, responsible for degenerative diseases such as cancer, arteriosclerosis, arthritis and neurodegenerative and aging processes; they can present antibactericidal, antiviral, antimutagenic, antiulcer or anticarlogenic activity.
  • UV 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). Of these ultraviolet radiation, the most lethal is UV-C radiation, although most of it is absorbed by ozone. Therefore, those that may have the greatest influence on the skin are UV-A and UV-B radiation.
  • Couroupita guianensis is a plant used in India for the treatment of skin diseases [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
  • indole alkaloids of the indole type [2, 1-6] quinazolo-6,12-diones, isolated from the fruits of Couroupita guianensis, and in particular of tryphantrin and its derivatives.
  • These alkaloids have antibacterial, antituberculous activity [a) L. A. Mitscher et al., Puré & Applied Chemistry; 1998, 70 (2), 365-371. b) WO951380], antimalarial [US2006160827 Al] and anti-inflammatory activity, for acting as inhibitors of prostaglandins and leukotrienes [H. Danz et al., Planta Medica; 2001, 67, 411-416].
  • Citrus, malic and isocitric acids have been isolated from the fruits of Couroupita guianensis [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], chlorogenic acids [P. V. 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 [alkaline] alkaloids [a) J. Bergman et al.
  • the present invention describes extracts of Couroupita guianenis leaves, their method of obtaining and their cosmetic use as antioxidants / anti-radicals / UV filters (ultraviolet).
  • 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. Extracts frequently have higher antioxidant activity than synthetic antioxidants such as BHT (butyrohydroxytoluene), BHA (butyrohydroxyanisole) or Trolox (soluble equivalent of ⁇ -tocopherol or vitamin E).
  • BHT butyrohydroxytoluene
  • BHA butyrohydroxyanisole
  • Trolox soluble equivalent of ⁇ -tocopherol or vitamin E
  • 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.
  • Liquid solid ratios are used high, preferably 30 g / g.
  • Water and / or hydroalcoholic and / or alcoholic solvents are used as solvent to be extracted.
  • Ci to C 4 alcohols and, preferably, ethanol or methanol are advantageously chosen.
  • a 1: 1 ethanol / water mixture is advantageously chosen.
  • the extraction temperature is the reflux of the solvent or mixture of extraction solvents and is in the range of 60-120 0 C and preferably between 85-95 0 C.
  • the extraction time is in the range of 3 hours to 21 days
  • the extractive process is protected from light to avoid possible alterations.
  • the yield of the extractive process ranges from 15% to 40% (g / g).
  • High liquid: solid ratios are used, preferably 99 g / g.
  • water and / or hydro-glycol and / or glycol solutions are used.
  • Cz to Ce glycols are advantageously chosen.
  • these glycols it is preferred to use propylene glycol and butylene glycol.
  • a 1: 1 butylene glycol / water mixture is advantageously chosen.
  • the extraction temperature is room temperature, approximately 20 0 C.
  • Extraction time is prolonged, from 3 to 21 days.
  • UV (ultraviolet) radiation is classified as 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), therefore, if a product absorbs radiation between 250 to 400 nm it can be used as a sunscreen.
  • the absorbency (Abs) of the filtered liquid extracts of Couroupita guianensis 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.
  • ii) Determination of the phenolic content of the filtered liquid extracts of Couroupita guianensis The phenolic compounds have a high antioxidant activity [YS Velioglu, op.
  • the phenolic content of the liquid extracts of Couroupita guianensis is determined according to the Folin Ciocalteu's method [A. Escarpa et al., Analytica Chinaca 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 the reagent is measured Ciocalteau's Folin (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 absorbency with a straight standard of gallic acid (0-100 ppm).
  • 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%.
  • the IC 50 or concentration that inhibits 50% of the DPPH * radical is measured.
  • 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.
  • ⁇ -carotene pro-vitamin A
  • linoleic acid a solution of ⁇ -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.
  • CAA [(Abs extract 120 min - Abs control 120 min) / (Abs control 0 min - Abs control 120 min)] * 100
  • 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.
  • a PBS buffer pH 7.4 is prepared (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 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 is read at 734 years. The reagent is diluted until it has an absorbance close to 0.7. 20 ⁇ L of the antioxidant extract is added to 2 mL of the reagent.
  • the filtered liquid extracts of Couroupita guianensis obtained according to the extraction procedure, have a capacity of inhibition of the ABTS * * 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).
  • 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).
  • 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).
  • 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 porous plate No. 3, and the final product, the filtered liquid extract of
  • Couroupita guianensis is stored refrigerated at 4 0 C and protected from light to prevent its alteration.
  • the phenolic content of the extract is determined by comparing the absorbance with a straight gallic acid standard (0-100 ppm).
  • the extract obtained according to the procedure described in this example 1 has a phenolic content of 32%.
  • the IC50 or concentration that inhibits 50% of the DPPH * radical was measured.
  • Oxidation inhibitory activity in an emulsified medium based on the oxidation inhibition of an emulsion of ⁇ -carotene (pro-vitamin A) and linoleic acid [G. J.
  • a solution of ⁇ -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 ⁇ L of the extract in 5 mL of emulsion) and of the control (200 ⁇ L of absolute ethanol in 5 mL of emulsion) are measured after 2 hours at 50 0 C. a blank following the same procedure but without adding ⁇ -carotene.
  • the antioxidant activity coefficient is measured (CAA,%), which is the oxidation ratio of ⁇ -carotene, or pro-vitamin A, in the presence and absence of antioxidant.
  • CAA [(Abs extract 120 min - Abs control 120 min) / (Abs control 0 min - Abs control 120 min)] * 100
  • the extract obtained according to the procedure described in this example 1 has a CAA of 58% at 250 ppm concentration.
  • 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, 0.2 g sodium azide) is prepared.
  • the TEAC reagent 38.4 mg ABTS * * 7 mM, 6.62 mg potassium persulfate 2.45 mM in 10 mL of 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.
  • 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).
  • 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 0 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).
  • the extract obtained according to the procedure described in this example 1 has at 100 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).
  • 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 0 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).
  • 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 porous plate No. 3, and the final product, the filtered liquid extract of Couroupita guianensis, is stored refrigerated at 4 0 C and protected from light to prevent its alteration.
  • the IC 50 or concentration that inhibits 50% of the DPPH * radical was measured.
  • Oxidation inhibitory activity in emulsified medium based on the oxidation inhibition of an emulsion of ⁇ -carotene and linoleic acid [G. /. Marco, op. cited (1968)].
  • a solution of ⁇ -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 ⁇ L of the extract in 5 mL of emulsion) and of the control (200 ⁇ L of absolute ethanol in 5 mL of emulsion) are measured after 2 hours at 50 0 C. a blank following the same procedure but without adding ⁇ -carotene.
  • the coefficient of antioxidant activity (CAA,%) which is the oxidation ratio of ⁇ -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)] * 100
  • the extract obtained according to the procedure described in this example 2 has a CAA of 40% at 250 ppm concentration.
  • 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 is prepared 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 of 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.
  • 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).
  • the antioxidant extract is diluted in ethanol, 2.5 mL of pH 6.60.2 M phosphate buffer and 2.5 mL of 1% potassium ferrocyanide are added to 1 mL thereof. Incubate at 50 0 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).
  • 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).

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Abstract

L'invention concerne un extrait des feuilles de Couroupita guianenis, son procédé d'obtention et son utilisation cosmétique en tant qu'antioxydant/antiradicalaire/filtre UV (ultraviolet). Les extraits obtenus à partir de feuilles sèches, moulues et tamisées, par extraction avec de l'eau, et/ou des alcools, par évaporation de ce dissolvant, par extraction ultérieure avec de l'eau et/ou des glycols de l'extrait sec de Couroupita guianensis et par filtrage; qui peuvent être utilisés dans le soin de la peau et/ou des cheveux, par exemple comme antioxydants ou inhibiteurs de radicaux, en tant qu'agents destinés à combattre le vieillissement ou comme protection solaire.
PCT/ES2008/000178 2007-03-30 2008-03-27 Extrait des feuilles de couroupita guianensis, procédé d'obtention et utilisation cosmétique de cet extrait en tant qu'antioxydant/antiradicalaire/filtre uv Ceased WO2008119852A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ESP200700856 2007-03-30
ES200700856A ES2304323B1 (es) 2007-03-30 2007-03-30 Extracto de las hojas de couroupita guianensis, procedimiento de obtencion y su uso cosmetico como antioxidante/antirradicalario/filtro uv.

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WO2008119852A1 true WO2008119852A1 (fr) 2008-10-09

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190132214A (ko) * 2018-05-17 2019-11-27 경남과학기술대학교 산학협력단 캐논볼나무의 신규 용도

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008035572A1 (fr) * 2006-09-19 2008-03-27 Noevir Co., Ltd. Agent hydratant, agent anti-vieillissement, agent blanchissant la peau et agent anti-oxydant

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008035572A1 (fr) * 2006-09-19 2008-03-27 Noevir Co., Ltd. Agent hydratant, agent anti-vieillissement, agent blanchissant la peau et agent anti-oxydant

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DESAI S.T. ET AL.: "Larvicidal property of Couroupita guianensis Aubl", INDIAN DRUGS, vol. 40, no. 8, 2003, pages 484 - 486 *
ERKNATH A.A. ET AL.: "Beta amyrin palmitate - Isolation from Couroupita guianensis Aubl. leaves", INDIAN DRUGS, vol. 39, no. 4, 2002, pages 213 - 216 *
GHEETA M. ET AL.: "Analgesic and anti-inflammatory activity of Couroupita guianensis Aubl", JOURNAL OF NATURAL REMEDIES, vol. 4, no. 1, 2004, pages 52 - 55 *
KHAN M.R. ET AL.: "Antibiotic activity of Couroupita guianensis", JOURNAL OF HERBS, SPICES AND MEDICAL PLANTS, vol. 10, no. 3, 2003, pages 95 - 108 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190132214A (ko) * 2018-05-17 2019-11-27 경남과학기술대학교 산학협력단 캐논볼나무의 신규 용도
KR102180876B1 (ko) 2018-05-17 2020-11-20 경남과학기술대학교 산학협력단 캐논볼나무의 신규 용도

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Publication number Publication date
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ES2304323A1 (es) 2008-10-01

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