WO2000018416A1 - Compositions d'antioxydants et leur procede de preparation - Google Patents

Compositions d'antioxydants et leur procede de preparation Download PDF

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Publication number
WO2000018416A1
WO2000018416A1 PCT/NZ1998/000146 NZ9800146W WO0018416A1 WO 2000018416 A1 WO2000018416 A1 WO 2000018416A1 NZ 9800146 W NZ9800146 W NZ 9800146W WO 0018416 A1 WO0018416 A1 WO 0018416A1
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WO
WIPO (PCT)
Prior art keywords
extract
antioxidant
polar solvent
seeds
acetone
Prior art date
Application number
PCT/NZ1998/000146
Other languages
English (en)
Inventor
Lai Yeap Foo
Original Assignee
Industrial Research Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Industrial Research Limited filed Critical Industrial Research Limited
Priority to PCT/NZ1998/000146 priority Critical patent/WO2000018416A1/fr
Priority to AU93691/98A priority patent/AU9369198A/en
Publication of WO2000018416A1 publication Critical patent/WO2000018416A1/fr

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Classifications

    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • 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]
    • 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

  • the invention relates to antioxidant compositions and processes for preparing them.
  • Oxidative spoilage of refined vegetable oils and foods containing them are associated almost exclusively with unsaturated fatty acids.
  • the reactions may be catalysed by several factors including UV light and metal ions and involved free radical participation.
  • the most susceptible portions of the fatty acids are in the vicinity of the carbon-carbon double bonds which readily react with free radical species.
  • These reactive intermediates propagate and degrade to give rise to a host of volatile acids, ketones and aldehydes to give rise to the characteristic "rancid" odours.
  • Antioxidants are widely employed to prevent these oxidative degradations and they represent one of the oldest established groups of modern food additives.
  • antioxidants The performance of an antioxidant is known to be highly specific. ⁇ -Tocopherol for instance serves as a better antioxidant in animal fats than vegetable oils and that the response of a specific substrate to any antioxidant can depend on the stereochemistry of the antioxidant molecule in biological systems and in processed foods. Evans and Reynhout 2 reported that certain antioxidants in model systems appear to be specific for one or more of the radicals formed in the oxidation process and radical formation varies with the degree of unsaturation, carbon chain length, enzyme activity, temperature and trace metals. Photoxidation affects the cis-trans configuration of breakdown products and the response to antioxidants and therefore oxidative reaction is more effectively inhibited by a combination of phenolic molecules that are specific for the substrate environments and the decomposition intermediate.
  • oxygen is also a source of degeneration, disease and aging. This is due to the reactive nature of the oxygen molecule or associated radicals such as the superoxide, the highly reactive hydroxy radical, that cause damage in the human body, attacking DNA leading to dysfunction, mutation and cancer. They can attack cell membranes enzymes and proteins, disrupting normal cell activities. Unsaturated fatty acid components are very susceptible to these attacks and cause damage in cells that line our arteries leading to their hardening and thickening and eventually to heart attacks and strokes. Free radical attacks on the protein in collagen can cause cross-linking resulting in stiffness in the body, reduce suppleness and increase wrinkling in the skin. It has been estimated that at least 85% of chronic and degenerative diseases are the result of oxidative damage 3 .
  • One particularly effective and desirable antioxidant is 1, 2, 3, 4, 6 - pentagalloyl glucose (I).
  • an extract of an Oenothera species comprising antioxidant Preferably the extract comprises 1,
  • the extract further comprises at least one of catechin (II) and procyanidin gallate (III). Most preferably the extract comprises 1, 2, 3, 4, 6 - pentagalloyl glucose, catechin and procyanidin gallate.
  • the species is Oenothera biennis (evening primrose).
  • the extract is a seed extract.
  • the extract is a polar solvent extract.
  • the polar solvent comprises at least one of acetone, ethanol, methanol and water.
  • the polar solvent is aqueous ethanol, aqueous acetone or aqueous methanol.
  • evening primrose seeds after oil removal are treated 10- 100% (preferably 30-70%) acetone, 10- 100% (preferably 40-90%) ethanol or 10- 100% (preferably 40-90%) methanol.
  • the polar solvent comprises at least one of acetone, ethanol, methanol or water.
  • the polar solvent is aqueous ethanol, aqueous methanol or aqueous acetone.
  • the extraction is carried out with 10- 100% (preferably 30- 70%) aqueous acetone, 10- 100% (preferably 40-90%) methanol or 10- 100% (preferably 40-90%) aqueous ethanol and the starting material is evening primrose.
  • the preferred Oenothera species is Oenothera biennis.
  • a method for preparing a 1, 2, 3, 4, 6 - pentagalloyl glucose extract comprising the step of extracting seeds of an Oenothera species with a polar solvent.
  • the polar solvent comprises at least one of acetone, ethanol, methanol or water.
  • the polar solvent is aqueous ethanol, aqueous methanol or aqueous acetone.
  • the extraction is carried out with 10- 100% (preferably 30- 70%) aqueous acetone, 10- 100% (preferably 40-90%) methanol or 10- 100% (preferably 40-90%) aqueous ethanol and the starting material is evening primrose.
  • the 1, 2, 3, 4, 6 pentagalloyl glucose extract may be further purified by chromatography, preferably by adsorption chromatography, more preferably by chromatography on Sephadex LH20.
  • the product of the above process is a preferred antioxidant for use in ingestible and topical compositions. It may be used in such compositions either alone or in combination with other antioxidants including other antioxidants from an Oenothera species eg catechin and/or procyanidin gallate.
  • Oenothera species eg catechin and/or procyanidin gallate.
  • an ingestible composition comprising an antioxidant-containing extract from an Oenothera species, preferably Oenothera biennis.
  • the ingestible composition comprises a preferred extract of a previously described aspect of the invention.
  • the ingestible composition is prepared in a unit dosage form containing 0.1 mg- 1000 mg (preferably lmg-250 mg) of extract.
  • the unit dosage form is a capsule or tablet.
  • a topical composition comprising an antioxidant-contai-oing extract of an Oenothera species.
  • the extract is a preferred extract of a previously described aspect of the invention.
  • the topical composition also comprises a cosmetic base.
  • a 60% aqueous acetone extract was prepared from spent Oenothera biennis seeds from which the oil had previously been removed.
  • the extracts are concentrated by a rotary evaporation and the residue diluted with water and dried to produce a powder.
  • This powder may be incorporated into tablets or capsules eg gelatin capsules.
  • topical compositions of the invention may be incorporated into a cosmetic cream.
  • a cosmetic cream may be prepared using either a water in oil emulsion or an oil in water emulsion.
  • Tablets, capsules and topical compositions may be prepared in a wide variety of ways known to those skilled in the preparation of pharmaceuticals, cosmetics and the like.
  • the critical feature is that the tablet, capsule or topical composition contains an antioxidant composition of the invention.
  • Ratios of solvents are by volume unlessj otherwise indicated.
  • Linoleic acid 99%; and b-carotene 95% were purchased from Aldrich Chemical Company.
  • Tween 20 came from Serva Feinbiochemica GmbH & Co. Spent evening primrose seeds were obtained from Industrial Research Limited's Chemical Processing Unit.
  • Antioxidant Activity The detection of antioxidant activity of the fractions was done by the method of Nakamura 5 . Fractions were separately spotted on a silica gel plate and the plate sprayed with a dilute solution of ⁇ -carotene, followed by irradiation with ultra-violet light. After several minutes of exposure, the plate was decolorized and fractions with antioxidant activity appeared as yellow spots.
  • the antioxidant activity of extracts was measured using the coupled ⁇ - carotene/linoleic acid reaction of Miller 6 .
  • 2.0 mL of ⁇ -carotene solution in chloroform (0. 167 mg/mL) were mixed with 50 mg/g linoleic acid and 400 mg of tween 20.
  • Chloroform was evaporated off in a rotovapor and 100 mL of oxygenated distilled water was added to the residue in small volume with vigorous agitation so as to form an emulsion.
  • 5.0 mL of this were added to tubes containing samples (10- 100 mg/mL) for evaluation.
  • the absorbance of the mixtures at 470 nm were measured immediately after the samples were mixed at 35°C, and then at regular intervals. In most cases, each extract or fraction was evaluated using 3 or 5 different concentrations in duplicates.
  • AAC [A E (t)-A C (t)]/[A(c( ⁇ )-A(c(t))
  • AAC is the antioxidant activity coefficient ranging from 0- 1000; AE is absorbance at t min for extract or sample; and Ac(o) and Ac(t) are the absorbances of the control at 0 and t min, respectively.
  • Antioxidant Activity of Extracts The rate of decline of the ⁇ -carotene 470 nm peak is related to the effectiveness of the antioxidant activity of the extracts. When compared with the control, all extracts showed varying degrees of antioxidant activity. As expected, the hexane extract produced the least amount of materials with the lowest antioxidant activity. The. evening primrose seeds, after all, had been previously stripped with hexane so that most hexane soluble materials would have been removed.
  • H 2 0 extract also exhibited good antioxidant activity, significantly superior to EtOAc extract, showing that the most active components were likely to be polar compounds.
  • a proanthocyanidin fraction obtained by eluting the Sephadex LH20 column with 60% aqueous acetone after it had been through with the EtOH described earlier, also showed good antioxidant activity.
  • the freeze-dried material was analysed by 13 C NMR, which showed many of the features exhibited by catechin, thus indicating the proanthocyanidin structure based at least in significant proportion on the catechin structure.
  • the relatively strong peak (-76 ppm) in the heterocyclic region indicated that an epicatechin 7 structural unit also was involved.
  • a relatively strong signal (166 ppm) was present, and the high field position of the signal indicated the presence of ester carbonyl units.
  • Antioxidant Activity Coefficient The antioxidant activity of the various extracts determined by the coupled b-carotene/linoleic acid reaction was expressed as the antioxidant activity coefficient used by Mallet 11 .
  • Test sample The test sample was prepared by extraction of spent evening primrose seeds (after oil removal) with aqueous acetone. The extract was concentrated and the resulting aqueous suspension diluted with H 2 0 and filtered over glass wool and the filtrate purified over XAD-4 resin to give the "activated" extract as freeze-dried powder. The sample was dissolved in DMSO prior to testing.
  • Chinese Hamster Cells The Chinese hamster cell line V79-5 was originally obtained from W R Inch (London, Ontario, Canada) and has been maintained in the Cancer Research Laboratory since 1979. It is stored as frozen aliquots in liquid nitrogen and, once thawed, it is maintained in a CO 2 incubator at 37°C by weekly trypsinisation and subculture in T25 flasks.
  • the culture medium used for maintaining the cell line is ⁇ -MEM, without ribo- and deoxyribo- nucleosides containing 10% heat inactivated foetal calf serum from Gibco, New Zealand, penicillin (100 units/mL) and streptomycin (100 ⁇ g/mL).
  • Rat Liver Microsomal Enzymes and Cofactors S9 was obtained as Arclor 1254-induced Sprague Dawley male liver lyophilised S-9 (MolTox LS-9) lot number 0406, from Molecular Toxicology Inc Maryland, USA. MolTox LS-9 vials were stored -70° and were reconstituted to 2.1 mL immediately prior to each test.
  • the mixture was stored on ice for the duration of the assay, and any remaining at the end of the day was discarded.
  • Micronucleus Assay For each experiment V79 cells were dispersed at 1 x 10 5 cells/mL in 100 mm tissue culture dishes containing 15 mLs of ⁇ -MEM and 10% foetal calf serum and incubated for 24 hours in a C0 2 incubator at 37°C. The medium was removed and cells were washed with phosphate buffered saline then 10 mLs of ⁇ -MEM, containing an appropriate dose of test substances, 1 mL of "S9" mix and no foetal calf serum, was added to each dish. The cells were then incubated or 4 hours in the presence of the test substances.
  • the medium containing the test compounds was removed, the cells were washed with phosphate buffered saline, trypsinised and resuspended in fresh growth medium. Cell densities were determined using an electronic Particle counter (Coulter Electronics).
  • cells were plated in a 60 mm tissue culture dish containing a sterile coverslip at a concentration of 1 x 10 5 cells/mL in 5 mLs of ⁇ -MEM containing 10% foetal calf serum.
  • Cytochalasin B was added to each dish to give a final concentration of 3 ⁇ g/mL and the cells were incubated for 20 hours then stained as described by T R Chen 12 . Then all but 1 L of medium was removed, and 1 mL of Carnoy's fixative (redistilled methanol: analytical grade acetic acid, 3: 1) was added at room temperature. After 2 minutes the fixative was aspirated and the coverslip allowed to air dry in the petri dish.
  • the coverslip was then stained by flooding with a sufficient volume of 80 ⁇ M Hoechst-33258 stain. After 8 to 10 minutes, protected from light, the coverslip was washed in deionised water, mounted on a slide and examined under a Nikon episcopic fluorescence microscope. Binucleate cells were scored for micronuclei identified using the criteria of Heddle et al 13 . At least 1000 cells were scored from each experiment.
  • the number of micronuclei and multiple micronulei counted in binucleate cells are summarised in Table 2 which shows that the evening primrose extract is associated with a significant and dose related decrease in the number of cells containing micronuclei induced by 3 ⁇ g/ l and 5 ⁇ g/ml PhlP (p>0.01).
  • Gelatin capsules are prepared by incorporation of lOOmg of the freeze dried powder from the 60% aqueous acetone extract of Example 1 into each capsule.

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Abstract

Cette invention se rapporte à un extrait acceptable dans le domaine alimentaire, cosmétique et pharmaceutique d'un antioxydant contenant l'espèce Oenothera, que l'on prépare en utilisant essentiellement l'extraction par solvant polaire. Cette invention présente des compositions ingérables et topiques contenant de tels extraits. Des extraits particulièrement préférés renferment du glucose 1, 2, 3, 4, 6-pentagalloyle.
PCT/NZ1998/000146 1998-09-30 1998-09-30 Compositions d'antioxydants et leur procede de preparation WO2000018416A1 (fr)

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Application Number Priority Date Filing Date Title
PCT/NZ1998/000146 WO2000018416A1 (fr) 1998-09-30 1998-09-30 Compositions d'antioxydants et leur procede de preparation
AU93691/98A AU9369198A (en) 1998-09-30 1998-09-30 Antioxidant compositions and process for their preparation

Applications Claiming Priority (1)

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PCT/NZ1998/000146 WO2000018416A1 (fr) 1998-09-30 1998-09-30 Compositions d'antioxydants et leur procede de preparation

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002009734A1 (fr) * 2000-08-01 2002-02-07 Oryza Oil & Fat Chemical Co.,Ltd. Inhibiteurs d'absorption de sucre et leur procede de production
WO2009010587A1 (fr) * 2007-07-19 2009-01-22 Marc Schwaller Utilisation d'au moins un extrait de parties aériennes de l'epilobe et/ou de l'onagre pour la préparation d'une composition destinée à restaurer la fonction barrière des tissus kératinisés ou des muqueuses.
WO2009128738A2 (fr) * 2008-04-18 2009-10-22 Warszawski Uniwersytet Medyczny Utilisation de l'extrait de graines déshuilées de primevère
US20100209407A1 (en) * 2007-06-06 2010-08-19 Basf Beauty Care Solutions France S.A.S. Mc-1r, mc-2r, and/or mu opioid receptors modulation
US20110189313A1 (en) * 2003-10-06 2011-08-04 Oryza Oil & Fat Chemical Co., Ltd. Method of using a green coffee bean extract to promote carnitine palmitoyltransferase activity
WO2013081046A1 (fr) * 2011-11-29 2013-06-06 国立大学法人信州大学 Extrait issu de rachis de raisin
US11331102B2 (en) 2018-08-03 2022-05-17 Nectero Medical, Inc. Purified pentagalloyl glucose and devices for delivery

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JPS60181006A (ja) * 1984-02-27 1985-09-14 Kanebo Ltd 皮膚化粧料
FR2574661A1 (fr) * 1984-12-19 1986-06-20 Roussel Uclaf Nouvelles compositions pour les soins de la peau renfermant de l'huile d'onagre et des extraits tissulaires de rate
FR2606279A1 (fr) * 1984-12-19 1988-05-13 Roussel Uclaf Nouvelles compositions renfermant de l'huile d'onagre et des produits bloqueurs de la formation des radicaux libres et d'oxygene singulets
JPH0987620A (ja) * 1995-09-21 1997-03-31 Matsumi Iehara 子葉処理体及びその製造方法
US5639460A (en) * 1995-06-07 1997-06-17 Raymond; Hal C. Aqueous plant extract having antiviral activity

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Publication number Priority date Publication date Assignee Title
JPS60181006A (ja) * 1984-02-27 1985-09-14 Kanebo Ltd 皮膚化粧料
FR2574661A1 (fr) * 1984-12-19 1986-06-20 Roussel Uclaf Nouvelles compositions pour les soins de la peau renfermant de l'huile d'onagre et des extraits tissulaires de rate
FR2606279A1 (fr) * 1984-12-19 1988-05-13 Roussel Uclaf Nouvelles compositions renfermant de l'huile d'onagre et des produits bloqueurs de la formation des radicaux libres et d'oxygene singulets
US5639460A (en) * 1995-06-07 1997-06-17 Raymond; Hal C. Aqueous plant extract having antiviral activity
JPH0987620A (ja) * 1995-09-21 1997-03-31 Matsumi Iehara 子葉処理体及びその製造方法

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Title
BALASINSKA ET AL.: "Total Antioxidative Activity of Evening Primrose (Oenothera paradoxa) cake Extract", J. AGRIC. FOOD CHEM., vol. 46, no. 9, 1998, pages 3558 - 3563 *
Nutr., Lipids, Health, Dis., (Proc. UNESCO Conf.) 1995, Meeting Data 1994, Editor(s): ONG, AUGUSTINE S.H. NIKI, ETSUO: PACKER, LESTER, Publisher: AOCS Press, Champaign, Ill., LU FEI et al., "Phenolic Antioxidant Components of Evening Primrose", pages 86-95. *
PATENT ABSTRACTS OF JAPAN *
PATENT ABSTRACTS OF JAPAN (C - 326) *
SHAHIDI ET AL.: "Antioxidant Activity of Phenolic Extracts of Evening Primrose (Oenothera Biennis): A Preliminary Study", J. FOOD LIPIDS, vol. 4, no. 2, 1997, pages 75 - 86 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6932990B2 (en) * 2000-08-01 2005-08-23 Oryza Oil & Fat Chemical Co., Ltd. Carbohydrate absorption inhibitor and method for manufacturing the same
WO2002009734A1 (fr) * 2000-08-01 2002-02-07 Oryza Oil & Fat Chemical Co.,Ltd. Inhibiteurs d'absorption de sucre et leur procede de production
JP4873824B2 (ja) * 2000-08-01 2012-02-08 オリザ油化株式会社 糖質吸収阻害剤およびその製造方法
US8802164B2 (en) * 2003-10-06 2014-08-12 Oryza Oil & Fat Chemical Co., Ltd. Method for promoting carnitine palmitoyltransferase activity using green coffee bean extract
US20110189313A1 (en) * 2003-10-06 2011-08-04 Oryza Oil & Fat Chemical Co., Ltd. Method of using a green coffee bean extract to promote carnitine palmitoyltransferase activity
US20100209407A1 (en) * 2007-06-06 2010-08-19 Basf Beauty Care Solutions France S.A.S. Mc-1r, mc-2r, and/or mu opioid receptors modulation
FR2918882A1 (fr) * 2007-07-19 2009-01-23 Marc Schwaller Utilisation d'au moins un extrait de parties aeriennes de l'epilobe et/ou de l'onagre pour la preparation d'une composition destinee a restaurer la fonction barriere des tissus keratinises ou des muqueuses
WO2009010587A1 (fr) * 2007-07-19 2009-01-22 Marc Schwaller Utilisation d'au moins un extrait de parties aériennes de l'epilobe et/ou de l'onagre pour la préparation d'une composition destinée à restaurer la fonction barrière des tissus kératinisés ou des muqueuses.
WO2009128738A3 (fr) * 2008-04-18 2010-06-10 Warszawski Uniwersytet Medyczny Utilisation de l'extrait de graines déshuilées de primevère
WO2009128738A2 (fr) * 2008-04-18 2009-10-22 Warszawski Uniwersytet Medyczny Utilisation de l'extrait de graines déshuilées de primevère
WO2013081046A1 (fr) * 2011-11-29 2013-06-06 国立大学法人信州大学 Extrait issu de rachis de raisin
JPWO2013081046A1 (ja) * 2011-11-29 2015-04-27 国立大学法人信州大学 ブドウ梗由来抽出物
US11331102B2 (en) 2018-08-03 2022-05-17 Nectero Medical, Inc. Purified pentagalloyl glucose and devices for delivery

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