WO2012163469A2 - Extraits d'eugenia uniflora - Google Patents

Extraits d'eugenia uniflora Download PDF

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Publication number
WO2012163469A2
WO2012163469A2 PCT/EP2012/001998 EP2012001998W WO2012163469A2 WO 2012163469 A2 WO2012163469 A2 WO 2012163469A2 EP 2012001998 W EP2012001998 W EP 2012001998W WO 2012163469 A2 WO2012163469 A2 WO 2012163469A2
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WO
WIPO (PCT)
Prior art keywords
extract
skin
acid
preparation
derivatives
Prior art date
Application number
PCT/EP2012/001998
Other languages
German (de)
English (en)
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WO2012163469A3 (fr
Inventor
Corinna Wirth
Original Assignee
Merck Patent Gmbh
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 Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to KR1020137034388A priority Critical patent/KR20140034255A/ko
Priority to EP12719938.8A priority patent/EP2720758A2/fr
Priority to CN201280026266.2A priority patent/CN103889510A/zh
Priority to JP2014513068A priority patent/JP2014515380A/ja
Publication of WO2012163469A2 publication Critical patent/WO2012163469A2/fr
Publication of WO2012163469A3 publication Critical patent/WO2012163469A3/fr

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Classifications

    • 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)
    • A61K36/61—Myrtaceae (Myrtle family), e.g. teatree or eucalyptus
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • the present invention relates to the use of extracts of plant parts of Eugenia uniflora for lightening the skin, and to cosmetic preparations containing these extracts and to a process for the preparation of such preparations.
  • Skin and hair color are dependent on the content, size, distribution and type of the nitrogen-containing, dark dye melanin, which is produced in the melanocyte-capable cells (melanocytes).
  • melanin is synthesized within the melanocytes.
  • the melanin is transferred to the keratinocytes in the form of so-called melanosomes.
  • Hyperpigmented areas of skin or lesions contain melasma (also called chloasma), i. irregularly shaped yellowish-brown spots.
  • Freckles are especially prone to skin type I, i. with very light skin and reddish hair.
  • Hyperpigmentation (chloasma), on the other hand, is common in those women who routinely deliver estrogen to their bodies. Very often the sun plays an important role. You can prevent it especially by regular sunscreen with a high SPF. In order to remove unsightly pigment spots, different ones are available
  • a large number of skin-whitening compounds for the treatment of pigmentation marks are available on the market.
  • these are compounds such as e.g. Hydroquinone (1,4-dihydroxybenzene), kojic acid, arbutin, aloesin, niacinamide, vitamin C or rucinol, which suppress the production of melanin in the skin.
  • Plant extracts such as e.g. from Morus alba or Phyllanthus emblica find, especially in the Southeast Asian region, application to brighten the Hautteint.
  • the invention has for its object to overcome the disadvantages indicated in the prior art and to develop effective alternatives that have an effective ability to brighten the skin - with the aim of improving the cosmetic effectiveness while reducing the side effects. Surprisingly, it has now been found that extracts from
  • Extracts of the leaves are used as fragrances due to their content of essential oils.
  • Extracts of Eugenia uniflora have a skin lightening effect is not known in the prior art.
  • JP 05-155750 A describes the use of extracts of Eugenia jambolana for skin lightening. Based on this document, however, the use of Eugenia un / / ora extracts for skin lightening is not suggested, since species of the same genus do not necessarily contain the same ingredients and therefore not the same
  • a first object of the present invention is therefore the
  • the aforementioned use of the extract can be done in in vitro or in vivo models.
  • the susceptibility of a particular cell to treatment with the extract can be determined by testing in vitro.
  • Extract of the invention is incubated at various concentrations for a period of time sufficient to allow the active agents to inhibit the synthesis of melanin, usually between about one hour and one week.
  • Cells from a biopsy sample can be used.
  • the amount of post-treatment melanin in the cells is then determined.
  • the use in vitro is carried out in particular on samples of
  • Mammalian species that suffer from skin pigmentation disorders may be of any mammalian species, e.g. B. one
  • the in vivo dose of the extract is beneficial to the susceptibility of the
  • a cosmetic dose will be sufficient to significantly reduce the undesirable amount of melanin in the target tissue while maintaining and ultimately improving the patient's quality of life.
  • Use will generally continue until there is a significant reduction in tyrosinase activity and melanin production, e.g. at least about 10% reduction in melanin content and can be continued until essentially no undesirable
  • Another preferred embodiment of the present invention is the use of an extract from plant parts of Eugenia uniflora for the prophylaxis, treatment and / or follow-up of pigmentary disorders of the skin.
  • extracts from Eugenia uniflora plant parts are suitable for use in the prophylaxis, treatment and / or follow-up of pigment disorders selected from the group of hyperpigmentation, freckles, age spots and sunspots.
  • the use of the extracts from plant parts of Eugenia uniflora can therefore be more cosmetic or pharmaceutical, in particular
  • dermatological being nature. It is preferably a
  • the plant extract from Eugenia uniflora can be prepared by methods known to those skilled in the art.
  • a plant extract which is particularly suitable for the use according to the invention is prepared as follows:
  • the plant parts can be used directly for the extraction according to step a). Typically, however, the plant parts are first dried and crushed.
  • the drying can be carried out, for example, in air or preferably in a vacuum drying oven at elevated temperature, preferably between 30 and 50 ° C., more preferably at about 40 ° C.
  • the crushing can be done by a common method, for example with the help of cutting tools such as knives or scissors, or with the help of a
  • the plant parts are extracted.
  • the extraction is carried out by methods known to those skilled in the art.
  • the plant parts are mixed with a solvent.
  • solvent selected from water, organic solvents or mixtures thereof.
  • organic solvents are methanol, ethanol, 1-propanol, 2-propanol, acetonitrile, acetone or ethyl acetate.
  • Solvent mixtures of water and organic solvents preferably contain 10-90% by volume of water, more preferably 30-70% by volume of water.
  • the solvent is selected from water or alcohol, preferably ethanol. In a particularly preferred embodiment, water is used as
  • the extraction is typically carried out at temperatures between 20 and 90 ° C, preferably between 50 and 90 ° C, more preferably at 70 ° C.
  • step b) the solvent is removed. This is typically done by filtration.
  • the extract obtained can then be concentrated and / or dried in a step c).
  • Rotary evaporator or a falling film evaporator can also be done under reduced pressure.
  • the drying of the extract can
  • the extract is complete to constant weight
  • extracts according to the invention is due to a combination of different active components in the extracts.
  • the skin-lightening effect of the extract is particularly good when it is prepared by the method described above and in particular according to its preferred embodiments.
  • a further embodiment of the present invention relates to the above-described use of extracts of plant parts of Eugenia uniflora in combination with at least one further active ingredient, preferably from the group of antioxidants, vitamins, UV filters, skin lightening agents, self-tanning agents, anti-inflammatory agents, antimicrobial drugs
  • skin moisturizing agents, anti-aging agents and anti-cellulite agents is selected.
  • the use is in combination with at least one or more UV filters or at least one further active substance or extract with a skin-lightening activity.
  • Another object of the present invention is a preparation containing an extract of plant parts of Eugenia uniflora and one or more UV filters.
  • a preparation comprising an extract of Eugenia uniflora and at least one further active substance or extract having a skin-lightening activity.
  • preparation is synonymous with the term “agent”, “composition” or “formulation” used.
  • the preparations are usually topically applicable preparations, e.g. cosmetic or dermatological formulations or medical devices. Topically applicable means according to the invention that the preparation externally and locally
  • the preparation is applied, i. that the preparation must be suitable, for example, to be applied to the skin can.
  • the preparations in this case contain a cosmetic, pharmaceutical or
  • topical preparations are preferably used as a cosmetic or dermatological preparation, particularly preferably as a cosmetic
  • the preparations may comprise or contain, consist essentially of or consist of the necessary and optional ingredients mentioned above and / or below. All connections or
  • compositions that can be used in the formulations are either known and commercially available or can be synthesized by known methods.
  • the preparations according to the invention preferably contain from 0.01 to 99% by weight of the extract from Eugenia uniflora, based on the total weight of the preparation. Preferably, an amount of 0.05 to 30 wt.% Is used, particularly preferably from 0, 1 to 10 wt.%.
  • the expert does not have any difficulties in selecting the quantities according to the intended effect of the preparation.
  • all UV filters can be used in the preparations according to the invention. Particularly preferred are those UV filters whose physiological harmlessness has already been demonstrated. Both for UVA and UVB filters, there are many known and proven substances from the literature. The compounds listed in the following lists are to be considered as examples only. Of course, other UV filters can be used.
  • Preferred formulations may contain organic UV filters, so-called hydrophilic or lipophilic sunscreen filters, which are in the UVA range and / or UVB range and / or IR and / or VIS range
  • UV filters are effective. These substances can be synthesized in particular under p-aminobenzoic acid derivatives, salicylic acid derivatives, ⁇ , ⁇ -diphenyl acrylate derivatives. derivatives, triazine derivatives, cinnamic acid derivatives and polymeric filters and silicone filters described in application WO 93/04665. Further examples of organic filters are given in the patent application EP-A 0 487 404. In the following, the named UV filters are usually named according to the INCI nomenclature.
  • para-aminobenzoic acid and its derivatives PABA, ethyl PABA, ethyl dihydroxypropyl PABA, ethylhexyl dimethyl PABA, e.g. sold under the name "Escalol 507" by the company ISP, glyceryl PABA, PEG-25 PABA, e.g. sold under the name "Uvinul P25” from BASF.
  • Salicylates homosalates sold under the name "Eusolex HMS” by Merck; Ethyl hexyl salicylates, e.g. sold under the name “Neo Heliopan OS” by Symrise; Dipropylene glycol salicylates, e.g.
  • TEA salicylates e.g. sold under the name "Neo Heliopan TS” by Fa. Symrise.
  • ⁇ , ⁇ -diphenylacrylate derivatives octocrylenes, e.g. distributed under the
  • Terephthalylidenedicamphorosulfonic acid e.g. sold under the name "Mexoryl SX” by Chimex
  • Polyacrylamidomethylbenzylidene camphor sold under the name "Mexoryl SW” from Chimex.
  • Phenylbenzimidazole derivatives phenylbenzimidazole sulfonic acid, e.g.
  • Phenylbenzotriazole derivatives Drometrizol trisiloxanes, e.g. sold under the name “Silatrizole” by the company Rhodia Chimie; Methylenebis (benzotriazolyl) tetramethylbutylphenol in solid form, e.g. sold under the name "MIXXIM BB / 100" from Fairmount Chemical, or in micronized form as an aqueous dispersion, e.g. sold under the name "Tinosorb M” from BASF.
  • Triazine derivatives ethylhexyltriazone, e.g. sold under the name "Uvinul T150" from BASF; Diethylhexylbutamidotriazone, e.g.
  • Anthraniline derivatives menthyl anthranilate, e.g. distributed under the
  • Imidazole derivatives Ethylhexyldimethoxybenzylidenedioxoimidazoline propionate.
  • Benzalmalonate Derivatives Polyorganosiloxanes containing functional benzalmalonate groups, e.g. Polysilicone-15, e.g. sold under the name "Parsol SLX” by Hoffmann LaRoche.
  • 4,4-Diarylbutadiene derivatives 1,1-dicarboxy (2,2'-dimethylpropyl) -4,4-diphenylbutadiene.
  • Benzoxazole Derivatives 2,4-bis [5- (1-dimethylpropyl) benzoxazol-2-yl (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazines, e.g. distributed under the
  • Suitable organic UV-protective substances are preferably to be selected from the following list: ethylhexyl salicylate,
  • Phenylbenzimidazole sulfonic acid benzophenone-3, benzophenone-4, benzophenone-5, n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate, 4-methylbenzylidene camphor, terephthalylidenedicamphor sulfonic acid, disodium phenyldibenzimidazole tetrasulfonate,
  • organic UV filters are incorporated usually in an amount of 0.01 to 20 weight percent, preferably 1 to 20 wt .-%, in formulations.
  • the preparations may contain, in addition to the extract and the optionally organic UV filters, as described above, further inorganic UV filters, so-called particulate UV filters.
  • organic UV filters as described above
  • particulate UV filters are possible both as a powder and as a dispersion or paste of the following types.
  • coated titanium dioxide for example Eusolex ® T-2000, Eusolex ® T-AQUA, Eusolex ® T-AVO, Eusolex ® T-OLEO), zinc oxides (for example Sachtotec® ®),
  • Iron oxides or else cerium oxides and / or zirconium oxides are preferred.
  • pigmentary Titandixoxid or zinc oxide are possible, wherein the particle size of these pigments is greater than or equal to 200 nm, for example ® Hombitan FG or Hombitan ® FF Pharma.
  • the preparations may further be preferred if the preparations contain inorganic UV filters which are prepared by customary methods, such as, for example, in US Pat
  • Cosmetics & Toiletries 1990, 105, 53 have been post-treated. This may include one or more of the following
  • Aftertreatment components are selected: amino acids, beeswax, fatty acids, fatty acid alcohols, anionic surfactants, lecithin,
  • Phospholipids sodium, potassium, zinc, iron or aluminum salts of fatty acids, polyethylenes, silicones, proteins (especially collagen or Elastin), alkanolamines, silica, alumina, other metal oxides, phosphates, such as sodium hexametaphosphate or glycerol.
  • Preferably used particulate UV filters are:
  • untreated titanium dioxides e.g. the products Microtitanium Dioxide MT 500 B from Tayca; Titanium Dioxide P25 from Degussa,
  • Silica post-treatment such as e.g. the product "Microtitanium Dioxide MT 100 SA of Tayca; or the product “Tioveil Fin” from Uniqema,
  • micronised titanium dioxides with alumina and / or aluminum stearates / laurate aftertreatment such as e.g. Microtitanium Dioxide MT 100 T from Tayca, Eusolex T-2000 from Merck,
  • Iron stearates aftertreatment such as e.g. the product "Microtitanium
  • Alumina and silicone aftertreatment such as e.g. the product "Microtitanium Dioxide MT 100 SAS", the company Tayca,
  • the treated micronized titanium dioxides used for combination may also be post-treated with:
  • Alumina and stearic acid such as. the product UV-Titan M160 of the company Sachtleben,
  • Sachtleben Aluminum and silicone oils such as, for example, the product UV titanium M262 from Sachtleben,
  • Polydimethylsiloxanes e.g. the product 70250 Cardre UF Ti02SI3 "from the company Cardre,
  • Escalol Z100 from ISP (alumina aftertreated ZnO dispersed in an ethylhexyl methoxycinnamate / PVP-hexadecenes / methicone copolymer blend)
  • Fuji ZNO-SMS-10 from Fuji Pigment (ZnO aftertreated with silica and polymethylsilsquioxane);
  • mixtures of different metal oxides for example titanium dioxide and cerium oxide with and without after-treatment, such as, for example, the product Sunveil A from Ikeda.
  • mixtures of different metal oxides for example titanium dioxide and cerium oxide with and without after-treatment, such as, for example, the product Sunveil A from Ikeda.
  • too Mixtures of alumina, silica and silicone aftertreated titanium dioxide / zinc oxide mixtures, such as the product UV titanium M261 Fa. Sachtleben be used.
  • These inorganic UV filters are incorporated usually in an amount of 0.1 to 25 weight percent, preferably 2 to 10 wt .-%, in the preparations.
  • UV filters can also be used in encapsulated form.
  • organic UV filters it is beneficial to use organic UV filters in
  • the capsules are in
  • Preparations to be used according to the invention are preferably contained in amounts which ensure that the encapsulated UV filters are present in the above-mentioned weight percent ratios in the preparation.
  • Skin-lightening active ingredients which can be used in the preparations according to the invention can, in principle, be all active ingredients known to the person skilled in the art.
  • melanogenesis inhibitors such as ascorbic acid and its derivatives, aloesin, niacinamide, emblica, elagic acid, licorice extract, mulberry tree extract, kojic acid, licorice root extract, rucinol, hydroquinone, azelaic acid, arbutin, magnesium ascorbyl phosphate or the like are suitable for combination.
  • Preferred examples of compounds having skin-lightening activity are hydroquinone, niacinamide, ascorbic acid and physiologically acceptable salts thereof, kojic acid, arbutin, aloesin, azelaic acid, elagic acid or rucinol.
  • Preferred examples of extracts with skin-lightening activity are licorice extract, mulberry extract or emblica.
  • At least one further active ingredient can be present in the preparations according to the invention.
  • the further active ingredient is preferably selected from the group of UV filters, antioxidants, vitamins, skin-lightening agents, anti-aging agents, anti-inflammatory agents, antimicrobial agents, agents for improving the moisture content of the skin (skin moistness regulators), anti-cellulite agents, Anti-wrinkle agents, anti-dandruff agents, anti-acne agents, deodorants, pigments and
  • Self-tanning substances more preferably from the group of UV filters, antioxidants, vitamins, skin lightening agents, self-tanning substances, anti-aging agents and anti-cellulite agents, most preferably from the group of UV filters, antioxidants, vitamins and skin lightening agents ,
  • These substances may, without being construed as limiting, include, among others, substances belonging to the so-called natural moisturizing factors, e.g. 2-oxopyrrolidines 5-carboxylic acid.
  • the preparation contains one or more antioxidants and / or one or more vitamins.
  • antioxidants Through the use of antioxidants, a protective effect against oxidative stress or against the action of radicals can generally be achieved, whereby the expert has no difficulty in selecting suitable fast or delayed-acting antioxidants.
  • suitable fast or delayed-acting antioxidants There are many well-known and proven from the literature Substances that can be used as antioxidants, eg
  • Amino acids e.g., glycine, histidine, tyrosine, tryptophan
  • amino acids e.g., glycine, histidine, tyrosine, tryptophan
  • imidazoles e.g., urocaninic acid
  • derivatives thereof peptides, e.g. D, L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g.
  • carotenoids such as ⁇ -carotene, ⁇ -carotene, lycopene
  • carotenes such as ⁇ -carotene, ⁇ -carotene, lycopene
  • chlorogenic acid and its derivatives such as dihydrolipoic acid
  • lipoic acid and its derivatives such as dihydrolipoic acid
  • aurothioglucose propylthiouracil and other thiols (such as thioredoxin, glutathione , Cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and
  • Glyceryl esters and their salts, dilauryl thiodipropionate,
  • Distearyl thiodipropionate, thiodipropionic acid and its derivatives such as esters, ethers, peptides, lipids, nucleotides, nucleosides and salts
  • sulfoximine compounds such as buthionine sulfoximines
  • Heptathioninsulfoximin in very low tolerated dosages (such as pmol to ⁇ / kg), (metal) chelators, (such as a-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (such as citric acid, lactic acid, Malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA, pentasodium
  • ethylenediaminetetramethylene phosphonate and its derivatives unsaturated fatty acids and their derivatives, vitamin C and derivatives (e.g.
  • Ascorbyl palmitate magnesium ascorbyl phosphate, ascorbyl acetate
  • Tocopherols and derivatives such as vitamin E acetate
  • vitamin A and derivatives such as vitamin A palmitate
  • Suitable antioxidants are also compounds of the general formulas A or B.
  • X is O or NH
  • R 2 is linear or branched alkyl having 1 to 30 C atoms
  • R 3 is linear or branched alkyl having 1 to 20 C atoms
  • R 4 are each independently H or linear or branched
  • R 5 H linear or branched alkyl having 1 to 8 carbon atoms or
  • R 6 is linear or branched alkyl having 1 to 8 carbon atoms.
  • antioxidants are also suitable for use in the formulations of the invention.
  • Known and commercially available mixtures are, for example, mixtures containing as active Ingredients lecithin, L - (+) - ascorbyl palmitate and citric acid, natural tocopherols, L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and
  • Citric acid such as Oxynex ® K LIQUID
  • tocopherol extracts from natural sources L - (+) - ascorbyl palmitate, L - (+) - ascorbic acid and citric acid (such as Oxynex L LIQUID ®), DL-a-tocopherol, L- ( +) - ascorbyl palmitate, citric acid and lecithin (such as Oxynex ® LM) or butylhydroxytoluene (BHT), L - (+) - ascorbyl palmitate and citric acid (such as Oxynex ® 2004).
  • Such antioxidants are used with compounds of formula (I) or sub-formulas thereof in such compositions usually in weight percent ratios in the range of 1000: 1 to 1: 1000, preferably in weight percent ratios of 100: 1 to 1: 100.
  • the flavonoids or bioflavonoids which are mainly known as plant dyes, frequently have an antioxidant potential.
  • Dihydroxyflavones having an OH group adjacent to the keto function or OH groups in 3'4'- or 6,7- or 7,8-position have antioxidant properties, while other mono- and Dihydroxyflavone partially have no antioxidant properties.
  • Quercetin (cyanidanol, cyanidolone 1522, meietin,
  • the preparations according to the invention may contain vitamins as further ingredients. Preference is given to vitamins and vitamin derivatives selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamin chloride hydrochloride (vitamin Bi), riboflavin (vitamin B 2 ), nicotinamide, Vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D 2 ), vitamin E, DL-oc-tocopherol, tocopherol-E-acetate, tocopherol hydrogen succinate, vitamin K1, esculin (vitamin P active ingredient), thiamin (vitamin bi), Nicotinic acid (niacin),
  • Preparations contain, in particular preferably vitamin A palmitate, vitamin C and its derivatives, DL-a-tocopherol, tocopherol E acetate, nicotinic acid, pantothenic acid and biotin. Vitamins are with the
  • Preparations usually in cosmetic use in the range of 0.01 to 5 wt .-%, based on the total weight added.
  • the preparations according to the invention may additionally contain anti-aging active ingredients, anti-cellulite active ingredients or conventional skin-friendly or skin-care active ingredients. Skin-friendly or
  • skin-care active ingredients may be all active ingredients known to the person skilled in the art.
  • Particularly preferred anti-aging agents are
  • Pyrimidinecarboxylic acids aryloximes, bioflavonoids, bioflavonoid-containing extracts, chromones or retinoids.
  • Suitable anti-aging ingredients especially for skin care
  • Preparations are preferably also so-called compatible solutes. These are substances that are involved in the osmoregulation of
  • osmolytes Plants or microorganisms are involved and made from these organisms can be isolated. Under the generic term compatible solutes also the described in the German patent application DE-A-10133202 osmolytes are taken. Suitable osmolytes are, for example, the polyols, methylamine compounds and amino acids and in each case their precursors. As osmolytes are in the sense of the Germans
  • Patent application DE-A-10133202 especially substances from the group of polyols, such as myo-inositol, mannitol or sorbitol and / or understood one or more of the following osmolytically active substances: taurine, choline, betaine, phosphorylcholine, Glycerophosphorylcholine, glutamine, glycine , ⁇ -alanine, glutamate, aspartate, proline, and taurine.
  • Precursors of these substances are, for example, glucose, glucose polymers, phosphatidylcholine, phosphatidylinositol, inorganic phosphates, proteins, peptides and polyamic acids.
  • Precursors are e.g. Compounds that are converted into osmolytes by metabolic steps.
  • compatible solute substances selected from the group consisting of Pynmidincarbonklaren (such as ectoine and hydroxyectoine), proline, betaine, glutamine, cyclic
  • DIP di-myo-inositol phosphate
  • cDPG cyclic 2,3-diphosphoglycerate
  • DGP 1, 1-diglycerol phosphate
  • ⁇ -mannosylglycerate Firoin
  • ⁇ -Mannosylglyceramide Firoin-A
  • ectoine (S) -1,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyectoine ((S, S) -1,4,5,6-tetrahydro-5 are among the pyrimidinecarboxylic acids hydroxy-2-methyl-4-pyrimidinecarboxylic acid) and their derivatives. Additional can be used as anti-aging active ingredients Merck products, such as 5,7-dihydroxy-2-methyl-chromone, marketed under the
  • RonaCare Luremin ® ® Ronacare isoquercetin, Ronacare ® tiliroside or Ronacare ® cyclopeptide be used. 5
  • chromones for example retinol (vitamin A), retinoic acid, retinaldehyde or else synthetically modified
  • the preparation additionally contains at least one self-tanning substance.
  • a preparation usually has a contrast-reducing effect and enables the achievement of an even skin tone.
  • the extracts from plant parts of Eugenia uniflora can accordingly also be used according to the invention in combination with self-tanning substances for the purpose of reducing the contrast and achieving an even skin tone.
  • a contrast reducing agent is a substance that has a
  • a contrast reduction can be achieved by preparations comprising an extract of Eugenia uniflora plant parts with a self-tanning substance, preferably containing dihydroxyacetone (DHA) and derivatives derived therefrom, DHA rapid, DHA plus or erythrulose, or a mixture of self-tanning substances, preferably DHA, DHA rapid, containing DHA plus and / or erythrulose is combined.
  • a self-tanning substance preferably containing dihydroxyacetone (DHA) and derivatives derived therefrom, DHA rapid, DHA plus or erythrulose
  • DHA dihydroxyacetone
  • Advantageous self-tanning agents in a mixture or preparation containing dihydroxyacetone may be used inter alia: glycerolaldehyde, hydroxymethylglyoxal, ⁇ -dialdehyde, 6-aldo-D-fructose, ninhydrin, 5-hydroxy-1,4-naphthoquinone (juglone) or 2-hydroxy - 1, 4-naphthoquinone (Lawson) or a mixture of said
  • the layer structure of the pigments not being limited.
  • the color pigment should be skin colored or brownish at a level of from 0.5 to 5% by weight.
  • compositions described are particularly suitable for use in the lightening of skin, inhibition of tyrosinase and / or
  • preparations according to the invention e.g. called: solutions, suspensions, emulsions, PIT emulsions, pastes, ointments, gels, creams, lotions, powders, soaps, surfactant-containing cleaning preparations, oils, aerosols, patches, envelopes, dressings and sprays, especially for external use.
  • Other applications are e.g. Sticks, shampoos and shower baths.
  • Further typical cosmetic application forms are also lipsticks, lip balms, powder, emulsion and wax make-up as well as sunscreen, pre-sun and after-sun preparations.
  • Cosmetic and dermatological preparations according to the invention may in particular be an anhydrous preparation, a lotion or emulsion, such as cream or milk, or microemulsion, in each case of the water-in-oil (W / O) or of the oil-in-water type (O / W ), a multiple emulsion, for example of the type Waser-in-oil-in-water (W / O / W) or vice versa (O / W / O), gels or solutions (especially oily-alcoholic, oily-aqueous or aqueous alcoholic gels or solutions), a solid stick, an ointment or even an aerosol.
  • the cosmetic and dermatological according to the invention may in particular be an anhydrous preparation, a lotion or emulsion, such as cream or milk, or microemulsion, in each case of the water-in-oil (W / O) or of the oil-in-water type (O / W ), a multiple emulsion, for example of the type
  • One embodiment of the invention is an emulsion which is present as cream or milk and, for example, fatty alcohols, fatty acids,
  • Fatty acid esters in particular triglycerides of fatty acids, lanolin, natural and synthetic oils or waxes and emulsifiers in
  • Embodiments provide oily lotions based on natural or synthetic oils and waxes, lanolin, fatty acid esters, especially triglycerides of fatty acids, or oily-alcoholic lotions a lower alcohol, such as ethanol, or a glycerol, such as
  • a particularly preferred preparation according to the invention may also be present as an alcoholic gel containing one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycerin, and a thickening agent such as silica.
  • the oily-alcoholic gels also contain natural or synthetic oil or wax.
  • the solid sticks are preferably made of natural or synthetic waxes and oils, fatty alcohols, fatty acids, fatty acid esters, lanolin and others
  • a preparation is formulated as an aerosol, it is preferable to use the customary propellants, such as alkanes, air, nitrogen,
  • Nitrous oxide more preferably alkanes or air.
  • the extract, as described, can be incorporated in the usual way into cosmetic or dermatological preparations.
  • any customary carrier substances, adjuvants and optionally further active ingredients can be added to the preparation.
  • Preferable excipients come from the group of preservatives,
  • Stabilizers solubilizers, colorants, i. Pigments, dyes, emulsifiers or odor improvers.
  • Preparations characterized in that a carrier suitable for cosmetic, pharmaceutical or / and dermatological applications and optionally physiologically acceptable auxiliaries and / or fillers are contained.
  • Ointments, pastes, creams and gels may contain the usual excipients suitable for topical administration, such as
  • Powders and sprays may contain the usual carriers, e.g. Lactose, talc, silicic acid, aluminum hydroxide, calcium silicate and polyamide powder or mixtures of these substances.
  • Sprays may additionally contain the usual volatile, liquefied propellants, e.g.
  • Chlorofluorocarbons propane / butane or dimethyl ether.
  • compressed air is advantageous to use.
  • air can also be used in non-pressurized metering devices, such as e.g. Pump sprays, are used.
  • Solutions and emulsions may be the usual carriers such as
  • Solvents, solubilizers and emulsifiers e.g. Water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol,
  • Cottonseed oil peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerine fatty acid esters, polyethylene glycols and fatty acid esters of
  • Sorbitans or mixtures of these substances are Sorbitans or mixtures of these substances.
  • a preferred solubilizer in general is 2-isopropyl-5-methylcyclohexanecarbonyl-D-alanine methyl ester.
  • Suspensions may be the usual carriers such as liquid
  • Diluents e.g. Water, ethanol or propylene glycol
  • Suspending agents e.g. ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline
  • Soaps may contain the usual excipients such as alkali metal salts of fatty acids, salts of fatty acid monoesters, fatty acid protein hydrolysates, isothionates, lanolin, fatty alcohol, vegetable oils, plant extracts, glycerol, sugars or mixtures of these substances.
  • Surfactant-containing cleaning products the usual carriers such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates,
  • Sulfosuccinic monoesters fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl taurates, sarcosinates,
  • Fatty acid diethanolamides vegetable and synthetic oils, lanolin derivatives, ethoxylated glycerol fatty acid esters or mixtures of these substances.
  • Facial and body oils may contain the usual carriers such as synthetic oils such as fatty acid esters, fatty alcohols, silicone oils, natural oils such as
  • Emulsions of the invention are advantageous and contain e.g. the said fats, oils, waxes and other fatty substances, and water or an aqueous phase, for example with solvents or hydrophilic surfactants, and an emulsifier, as is commonly used for such a type of preparation.
  • mineral oils mineral waxes - Oils such as triglycerides of capric or caprylic acid, also natural oils such. Castor oil;
  • Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes,
  • the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the context of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or or unsaturated,
  • branched and / or unbranched alcohols of a chain length of 3 to 30 carbon atoms, from the group of esters of aromatic carboxylic acid and saturated and / or unsaturated, branched and / or
  • ester oils can then be advantageously selected from the group
  • Oil phase can be advantageously selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12-18 C-atoms.
  • the fatty acid triglycerides can For example, be selected from the group of advantageous
  • oils e.g. As olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like. Any mixtures of such oil and wax components are also advantageous to use in the context of the present invention. It may also be advantageous, if appropriate, to use waxes, for example cetyl palmitate, as the sole lipid component of the oil phase.
  • the aqueous phase of the preparations according to the invention may advantageously contain alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether,
  • Thickening agents which may be advantageously selected from the group of silica, aluminum silicates, polysaccharides and their derivatives, e.g. Hyaluronic acid, xanthan gum,
  • Hydroxypropylmethylcellulose particularly advantageous from the group of polyacrylates, preferably a polyacrylate from the group of so-called Carbopole, for example, Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • Carbopole for example, Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
  • mixtures of the abovementioned solvents are used.
  • Solvents can be another component of water.
  • the preparations according to the invention contain hydrophilic surfactants.
  • the hydrophilic surfactants are preferably selected from the group of alkylglucosides, acyl lactylates, betaines and cocoamphoacetates.
  • emulsifiers for example, the known W / O and O W emulsifiers can be used. It is advantageous to use further customary co-emulsifiers in the preferred O / W emulsions according to the invention.
  • suitable co-emulsifiers are, for example, O / W emulsifiers, primarily from the group of substances with HLB values of 11-16, very particularly advantageously with HLB values of 14.5-15.5, provided that the O / W emulsifiers have W emulsifiers have saturated radicals R and R '. If the O W emulsifiers have unsaturated radicals R and / or R ', or if isoalkyl derivatives are present, the preferred HLB value of such emulsifiers may also be lower or higher.
  • Polyethylene glycol (12) isostearate, polyethylene glycol (13) isostearate,
  • Polyethylene glycol (14) isostearate, polyethylene glycol (15) isostearate,
  • Polyethylene glycol (24) isostearate, polyethylene glycol (25) isostearate,
  • Polyethylene glycol (20) oleate Polyethylene glycol (20) oleate.
  • the sodium laureth-11-carboxylate can be advantageously used.
  • the alkyl ether sulfate sodium laureth-4 sulfate can be advantageously used.
  • polyethyleneglycol (30) cholesteryl ether can be advantageously used.
  • Polyethyleng lycol (25) soybean oil has been proven.
  • the polyethylene glycol (60) Evening Primrose Glycerides can advantageously be used (Evening Primrose
  • Polyethylene glycol (20) to choose sorbitan monooleate
  • W / O emulsifiers can be used:
  • Fatty alcohols having 8 to 30 carbon atoms monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched
  • Particularly advantageous W / O emulsifiers are glyceryl monostearate, glyceryl monoisostearate, glyceryl monomyristate, glyceryl monooleate,
  • Sucrose distearate cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, isobehenyl alcohol, selachyl alcohol, chimyl alcohol,
  • Glyceryl monocaprinate glyceryl monocaprylate or PEG-30 dipolyhydroxystearate.
  • the preparation may contain cosmetic adjuvants which are commonly used in this type of preparation, e.g.
  • Thickeners emollients, moisturizers,
  • surfactants such as soaps, emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or pigments that color the agent itself or the skin, and other ingredients commonly used in cosmetics.
  • polyol or mixtures thereof include ethanol, i-propanol, propylene glycol, glycerine and sorbitol.
  • the present invention also provides a process for
  • an extract of Eugenia uniflora is mixed with at least one carrier suitable for topical applications and optionally with physiologically acceptable excipients and / or fillers.
  • Another embodiment of the present invention relates to a pharmaceutical composition containing an extract of plant parts of Eugenia uniflora.
  • compositions pharmaceutical formulations
  • “Pharmaceutical preparation” here is any agent which in the prophylaxis, therapy, follow-up or treatment of
  • Patients can be used, at least temporarily a pathogenic Show modification of the overall state or condition of individual parts of the patient organism, preferably as a result of pigmentary disorders of the skin.
  • a pathogenic Show modification of the overall state or condition of individual parts of the patient organism preferably as a result of pigmentary disorders of the skin.
  • Adjuvants are added.
  • any substance that enables, enhances or modifies the extracts according to the invention is an "adjuvant.”
  • Known adjuvants are, for example, aluminum compounds such as aluminum hydroxide or aluminum phosphate, saponins such as QS 21, muramyl dipeptide or
  • the introduction of the pharmaceutical agent into a cell or an organism according to the invention can be done in any way that allows tyrosinase with those in the
  • the pharmaceutical agent of the present invention may be administered orally, topically, transdermally, transmucosally, transurethally, vaginally, rectally, pulmonarily, enterally and / or parenterally, preferably topically or transdermally.
  • the chosen mode of administration depends on the indication to be given
  • the different modes of administration allow for site-specific therapy that minimizes side effects and that
  • the dosage forms of the pharmaceutical agent are mixed with the usual solid or liquid carriers and / or diluents and the excipients commonly used according to the desired mode of administration in a suitable dosage and in a conventional manner.
  • pharmaceutically acceptable excipients known to those skilled in the art may form part of the pharmaceutical composition of the invention, the amount of excipient material combined with the active ingredient to produce a single dosage varying with the individual to be treated and the mode of administration.
  • pharmaceutically acceptable additives include salts, buffers, fillers, stabilizers, chelating agents, antioxidants, solvents, binders, lubricants,
  • Tablet coatings examples of such excipients are water, vegetable oils, benzyl alcohols, alkylene glycol, polyethylene glycol,
  • Glycerol triacetate Glycerol triacetate, gelatin, carbohydrates, e.g. Lactose or starch, magnesium stearate, talc and Vaseline.
  • the pharmaceutical formulation may be in the form of tablet, film-coated tablet, dragee, lozenge, capsule, pill, powder, granule, syrup, juice, drops, solution, dispersion, suspension, suppository, emulsion, implant, cream, gel, ointment, paste, lotion, serum , Oil, spray, aerosol, glue, plaster or dressing.
  • the oral dosage form used is preferably tablets, film-coated tablets, dragees, lozenges, capsules, pills, powders, granules, syrups, juices, drops, solutions, dispersions or
  • parenteral dosage forms such as e.g. Suppositories, suspensions,
  • the active pharmaceutical ingredient is at least one pharmaceutical
  • the acceptable carrier such as microcrystalline cellulose
  • excipients such as moisturizers
  • to be applied to the skin solid formulations such as creams, gels, ointments, pastes, powders or emulsions
  • to be applied to the skin liquid formulations such as solutions, suspensions, lotions, serums, oils, sprays or aerosols in the usual way.
  • the pharmaceutical agent is for topical application.
  • the pharmaceutical agent may also be present as a solid composition, for example in the lyophilized state, and then by addition of a dissolving agent, such as e.g. distilled water, before the
  • the concentration of the extract in the formulation may be 0.01 to 99
  • composition Percent by weight. It is crucial that the pharmaceutical composition comprises as active ingredient an effective amount of the extract together with the pharmaceutically acceptable excipients.
  • effective amount or “effective dose” are used herein
  • a pharmaceutical agent having a prophylactic or therapeutically relevant effect on a disease or pathological change in the cell, tissue, organ or mammal having a prophylactic or therapeutically relevant effect on a disease or pathological change in the cell, tissue, organ or mammal.
  • a "prophylactic effect” prevents the onset of a disease and includes an increase in the normal physiological function prophylaxis is particularly advisable when an individual has predispositions for the onset of the aforementioned diseases, such as a family history, a genetic defect or a recent Disease
  • a "therapeutically relevant effect” partially or wholly relieves one, several or all disease symptoms or results in the partial or complete return of one or more or all of the physiological or biochemical parameters associated with or causative of the disease or pathological change , in the normal state.
  • follow-up is understood as a type of therapeutic treatment when the extract is administered at certain intervals, eg to completely eliminate the symptoms of a disease.
  • the dose or dose range for the dose is large enough to achieve the desired prophylactic or therapeutic effect of inducing a biological or medical response.
  • the dose will vary with the age, constitution and gender of the patient, as well as the severity of the disease. It is understood that the specific dose, frequency and duration of administration of a variety of
  • the individual dose can be adjusted both in relation to the primary illness and in relation to the occurrence of possible complications.
  • the exact dose is through one
  • the pharmaceutical composition in order to promote the medicinal effect, may also comprise one or more further active ingredients, simultaneous or sequential administration being conceivable.
  • the therapeutic effect of the pharmaceutical composition according to the invention may be, for example, that the inhibition of the
  • the extracts are also characterized by high application safety and good formulatability. So they are easy to incorporate into preparations and have increased stability in the preparations.
  • water extracts advantageous because they are water-soluble and thus very easy to incorporate.
  • the preparation of the extracts is advantageous, since in particular the production of the water extract is particularly environmentally friendly. Even without further statements, it is assumed that a person skilled in the art can make the most of the above description. All mentioned as well as further constituents or components are familiar to the person skilled in the art and can undergo a special design for the teaching according to the invention in routine experiments. All documents cited in the specification are hereby incorporated by reference in their entirety in the disclosure of the present invention.
  • Fig. 1 shows the HPLC chromatograms of the extract of Eugenia uniflora (a) and of pure eugenin (b) in comparison.
  • Example 1 Extracts from Eugenia uniflora
  • B16V mouse melanoma cells (manufacturer: DSMZ, article number: ACC370) are mixed in RPMI medium (Invitrogen, article no .: 31870), which additionally contains 10% FBS (fetal bovine serum; Invitrogen, article no: 10499044 ), 2 mM L-glutamine (Invitrogen, item no: 25030) and 1 mM sodium pyruvate (Invitrogen, item no: 11360) are added and incubated for 72 h at 37 ° C and 5% C0 2 . The medium is separated and the cells are washed once with 10mL DPBS (Dulbecco's Phosphate-Buffered Salines, Invitrogen, Item No. 14190) and the medium is then aspirated. 1 mL of HyQtase-Cell Detachment Solution (Hyclone,
  • the cells are incubated for 24 h at 37 ° C. and 5% CO 2, after which the medium is removed. Subsequently, 1980 L of the substance dilution
  • the water extract from Example 1 is dissolved in DMSO and then filtered through a sterile filter (0.2 m, Millipore, Article No. SLLG0 3SL). The solution is then mixed with the modified RPMI medium (see above, but in this case the FBS Content only 5%) so that the final concentration of the extract is 0.1 mg / ml or 9.95 mg / ml.
  • alpha-MSH solution alpha-melanocyte stimulating hormone, DMSO, Sigma, Article No.: D2650
  • DMSO fetal sulfate
  • D2650 alpha-melanocyte stimulating hormone
  • the mixture is again incubated at 37 ° for 24 h washed ° C and 5% CO2. the process described in this section as a whole is repeated twice more.
  • the media is aspirated and the cells with 1000 ⁇ _ DPBS (Invitrogen, product no. 14190). the medium is again 250 ⁇ _ HyQtase-Cell
  • Hyclone Item No. SV30030.01
  • Hyclone Item No. SV30030.01
  • the 6-well plate is pivoted several times and the HyQtase- Cell Detachment Solution is then removed by suction. Then the cells are incubated for 5 min in the incubator at 37 ° C and 5% C0 2 .
  • the cells are taken up in 1.5 ml of DPBS (Invitrogen, Item No. 14190) and transferred to a cup (SARSTEDT, Ref. 72.692.005). Subsequently, the cell number is determined. For this, the cells are stained with trypan blue and counted in a Neubauer counting chamber. Centrifuge the cells at 3500g for 1min. The obtained pellets are photographed and
  • Example 1 Since eugenin is soluble in ethanol, the ethanol extract of Example 1 is analyzed by HPLC. For comparison, pure eugenin (purity 99%) is measured.
  • Eluent B 0.1 M sodium dihydrogen phosphate buffer pH 2.6 + 1% acetonitrile gradient:
  • Example 4 O / W emulsions for skin lightening, data in% by weight
  • Example 5 W / O emulsions for skin lightening, data in% by weight
  • phase A Heat phase A to 75 ° C, phase B to 80 ° C. Slowly add phase B into phase A with stirring. Homogenize. Allow to cool with constant stirring and add phase C at 40 ° C.
  • Phase B completely dissolved to phase A give.

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Abstract

La présente invention concerne l'utilisation d'extraits de parties de la plante Eugenia uniflora pour éclaircir la peau, ainsi que des préparations cosmétiques contenant ces extraits, et un procédé de fabrication de ces préparations.
PCT/EP2012/001998 2011-05-30 2012-05-09 Extraits d'eugenia uniflora WO2012163469A2 (fr)

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KR1020137034388A KR20140034255A (ko) 2011-05-30 2012-05-09 유제니아 유니플로라의 추출물
EP12719938.8A EP2720758A2 (fr) 2011-05-30 2012-05-09 EXTRAITS D'EUGENIA UNIFLORA& xA;
CN201280026266.2A CN103889510A (zh) 2011-05-30 2012-05-09 红果仔的提取物
JP2014513068A JP2014515380A (ja) 2011-05-30 2012-05-09 ユーゲニア・ユニフローラからの抽出物

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CN115152858B (zh) * 2022-07-26 2023-08-15 中国农业科学院茶叶研究所 一种基于特征化合物的普洱茶渥堆发酵适度的判别方法

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