WO2013146797A1 - Promoteur de la production d'héparane sulfate - Google Patents

Promoteur de la production d'héparane sulfate Download PDF

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Publication number
WO2013146797A1
WO2013146797A1 PCT/JP2013/058825 JP2013058825W WO2013146797A1 WO 2013146797 A1 WO2013146797 A1 WO 2013146797A1 JP 2013058825 W JP2013058825 W JP 2013058825W WO 2013146797 A1 WO2013146797 A1 WO 2013146797A1
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Prior art keywords
heparan sulfate
glucosamine
sulfate production
production promoter
extract
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PCT/JP2013/058825
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English (en)
Japanese (ja)
Inventor
雅人 飯野
俊介 入山
留美子 藤原
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株式会社資生堂
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Publication of WO2013146797A1 publication Critical patent/WO2013146797A1/fr

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    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7008—Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
    • 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)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/896—Liliaceae (Lily family), e.g. daylily, plantain lily, Hyacinth or narcissus
    • 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]
    • A61K8/9794—Liliopsida [monocotyledons]
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • 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
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • the present invention provides a heparan sulfate production promoter comprising a mixture of madonna lily (Lilium Candidum) extract and glucosamine.
  • Heparan sulfate is a linear polysaccharide composed of glucosamine, glucuronic acid, and iduronic acid, and is often in the form of heparan sulfate proteoglycans in which multiple heparan sulfate chains are covalently bound to proteins on the cell surface and extracellular matrix of animals.
  • Heparan sulfate proteoglycans bind to a wide variety of physiologically active proteins such as cell growth factors, chemokines, cytokines, morphogenic factors, etc., and regulate cell differentiation, cell growth, cell morphogenesis, cell adhesion, mutual recognition, cell invasion It plays various roles in the body, such as protection and promotion of wound healing.
  • heparan sulfate proteoglycans are known to function to accumulate heparin-binding growth factors (bFGF, HGF, VEGF, HB-EGF, etc.) outside the cell.
  • Pearlcan a kind of heparan sulfate proteoglycan, is also present in the epidermis basement membrane located at the boundary between the epidermis and dermis. In the skin, heparin-binding growth factor is bound to the epidermis basement membrane to bind it between the epidermis and the dermis. It controls the movement of growth factors.
  • perlecan present in the epidermal basement membrane also regulates the action of growth factors on epidermal basal cells bound to the basement membrane, and it has been clarified that it is essential for the good growth and differentiation of the epidermis. .
  • enhancing the production of heparan sulfate also leads to prevention and suppression of wrinkles (Experimental Dermatology Vol. 20, 10, Oct. 2011, PP.810-814: Non-patent literature) 1 and WO2009 / 123215: Patent Document 1).
  • WO2011 / 040696 Patent Document 2
  • VEGF-A vascular endothelial growth factor-A
  • FGF-7 fibroblast growth factor-7
  • heparan sulfate synergistically accumulates in keratinocytes due to activation of melanocytes by inflammation and promotion of melanosome delivery by failure of FGF-7 control. Therefore, increasing the production of heparan sulfate also leads to a whitening effect for preventing and suppressing pigmentation such as spots, dullness, and freckles.
  • Heparan sulfate has various structures due to modifications such as sulfation and epimerization. Heparan sulfate proteoglycans are responsible for the physiological activity of oligosaccharides, and their sugar chain length, sugar chain sequence, and specific sulfate group arrangement are important for cell function. Shows a unique pattern and interacts with a specific protein. Therefore, heparan sulfate is responsible for the expression of cellular properties. In addition, heparan sulfate has been shown to be responsible for the cellular receptors of various viruses, including respiratory syncytial virus.
  • Lily extract is known to inhibit heparanase in WO 2009/123215 (Patent Document 1).
  • JP-A-2011-225564 (Patent Document 4) exhibits excellent preventive and ameliorating effects on skin aging phenomena such as wrinkles, sagging, spots, and freckles, and keeps the skin youthful and healthy.
  • Or improved and improved skin-beautifying and skin-whitening ingredients with low skin irritation, obtained from plant buds belonging to the family Liliaceae (Lilium), elastase activity inhibitory action, Cosmetics containing as an active ingredient an extract having an antioxidant action, a protein saccharification inhibiting action and a tyrosinase activity inhibiting action are known.
  • JP 2012-41284 contains, as an active ingredient, a plant extract of the genus Liliaceae that excels in anti-aging, whitening, antioxidant, slimming, and anti-inflammatory effects.
  • a whitening agent, an antioxidant, a slimming agent and an anti-inflammatory agent could be provided.
  • Glucosamine hydrochloride is known in Japanese Patent Application Laid-Open No. 2003-261432 (Patent Document 6) as an external preparation for skin containing an advanced glycation end products production inhibitor and a whitening agent (glucosamine is described as one of the components).
  • Patent Document 6 Japanese Patent Application Laid-Open No. 2003-261432
  • Patent Document 7 one or more selected from a plant having a melanin production inhibitory action selected from glucosamine and derivatives thereof, and an algal extract;
  • a skin external preparation having a markedly improved skin whitening effect characterized by containing a lavender extract is known.
  • heparan sulfate is an important component for humans and animals and has various physiological functions.
  • drugs that promote its production are not well known.
  • An object of the present invention is to provide a novel heparan sulfate production promoter.
  • a heparan sulfate production promoter comprising a mixture of a madonna lily (Lilium Candidum) extract and glucosamine.
  • a whitening agent comprising the heparan sulfate production promoter of (1) or (2) as a whitening component.
  • a wrinkle formation preventive or inhibitor comprising the heparan sulfate production promoter of (1) or (2) as an anti-aging component.
  • the heparan sulfate production promoter according to (1) or (2) which is a whitening agent.
  • the heparan sulfate production promoter of the present invention can efficiently promote the production of heparan sulfate, it can improve, treat, prevent, and normalize various conditions or symptoms related to degradation, reduction, and deficiency of heparan sulfate.
  • Use for whitening such as blemishes, freckles, dullness improvement, anti-aging purposes such as wrinkle improvement, wound healing promotion, etc., eg cell differentiation, regulation of cell proliferation, cells Can be suitably used for normalization of abnormalities in cell morphogenesis, cell adhesion, mutual recognition, cell infiltration, and the like.
  • the present invention provides a heparan sulfate production promoter composed of a mixture of Madonna lily (Lilium Candidum) extract and glucosamine hydrochloride.
  • Madonna lily is a perennial plant native to Asia that belongs to the lily family (Liliaceae), and grows naturally and grows separately in bulbs.
  • Madonna lily extract is used for prescription of arthritis and rheumatic pain, and is said to be good for preventing wrinkles as a cosmetic effect.
  • the above extract can be obtained by a conventional method.
  • a part or all of a plant that is the origin of the extract can be obtained by soaking or heating and refluxing together with an extraction solvent at room temperature or after heating, filtering and concentrating.
  • an extraction solvent for extraction, any part of a plant such as leaves, flowers, seeds, roots, stems, buds, branches, and bark may be used, but an extract from a bulb is preferred.
  • the extraction site Prior to solvent extraction, the extraction site may be dried.
  • the extraction solvent any solvent can be used as long as it is usually used for extraction.
  • organic solvents such as alcohols such as methanol, ethanol, propylene glycol, 1,3-butylene glycol and glycerin, hydrous alcohols , Chloroform, dichloroethane, carbon tetrachloride, acetone, ethyl acetate, hexane, or an aqueous solvent such as water, physiological saline, phosphate buffer, borate buffer, etc., either alone or in combination. it can.
  • one or more kinds selected from water, methanol, ethanol, and 1,3-butylene glycol are preferably used as the solvent.
  • a mixture of water, ethanol and 1,3-butylene glycol is used as the solvent.
  • the extract obtained by extraction with the above solvent can be used as it is or, for example, an extract concentrated by lyophilization or the like, and if necessary, an adsorbent method, for example, an ion exchange resin removed impurities, A polymer (eg, Amberlite XAD-2) adsorbed on a column, eluted with a desired solvent, and further concentrated can be used.
  • an adsorbent method for example, an ion exchange resin removed impurities,
  • a polymer eg, Amberlite XAD-2
  • Glucosamine is a kind of “amino sugar” whose chemical name is “2-amino-2-deoxy-D-glucose”, and has a structure in which the hydroxyl group at the 2-position of glucose is substituted with an amino group. It is widely known that it is a constituent of chitin contained in insects and chitosan, which is an N-acetylated form of chitin, but N-acetylated forms (N-acetylglucosamine) are also found in mammals. It is present in various glucosaminoglycans, including hyaluronic acid, glycoproteins and glycolipids.
  • Glucosamine is mostly “glucosamine hydrochloride” obtained by decomposing chitin with hydrochloric acid, but “glucosamine sulfate” is also frequently used.
  • Preferred in the present invention is glucosamine hydrochloride.
  • the content of the mixture of madonnalyri and glucosamine is not particularly limited as long as it is an amount sufficient to effectively exert the heparan sulfate production promotion effect. What is necessary is just to select suitably according to a use.
  • the blending amount of madonna lily relative to the whole heparan sulfate production promoter is usually 0.000001% by mass to 1% by mass, especially 0.00001% by mass to 0.1% by mass
  • the amount of glucosamine is usually 0.00001% by mass to 0.1% by mass, more preferably 0.00005% by mass to 0.05% by mass, especially 0.0001% by mass to 0%.
  • the ratio of Madonna Lilly to glucosamine is 10: 1 to 1: 100, preferably 1: 1 to 1:10, more preferably 1: 2 with the amount of Madonna Lilly as a dry weight. As good as
  • the heparan sulfate production promoter according to the present invention can be formulated according to a conventional method, and can also be prepared as a component constituting an external preparation for skin.
  • skin such as cosmetics and pharmaceuticals including quasi drugs is used.
  • Components used for external preparations such as oils, surfactants, powders, coloring materials, water, alcohols, thickeners, chelating agents, silicones, antioxidants, UV absorbers, humectants, fragrances, various medicinal effects Components, preservatives, pH adjusters, neutralizers and the like are appropriately blended as necessary.
  • the other components are not particularly limited and may be appropriately selected depending on the use, dosage form, administration form, and the like of the pharmaceutical composition.
  • Examples include pharmaceutically acceptable carriers and / or adjuvants.
  • adjuvants include diluents, binders, disintegrants, thickeners, dispersants, reabsorption accelerators, corrigents, buffers, surfactants, solubilizers, preservatives, emulsifiers, isotonic agents. , Stabilizers, pH adjusters and the like.
  • heparan sulfate production promoter of the present invention when used as an external preparation for skin, components usually used in external preparations such as whitening agents, moisturizers, antioxidants, oily components, ultraviolet absorbers, surfactants , Thickeners, alcohols, powder components, colorants, aqueous components, water, various skin nutrients, and the like can be appropriately blended as necessary.
  • edetate disodium edetate trisodium, sodium citrate, sodium polyphosphate, sodium metaphosphate, sequestering agents such as gluconic acid, preservatives such as methylparaben, ethylparaben, butylparaben, caffeine, tannin, Verapamil, tranexamic acid and its derivatives, licorice extract, grabrizine, hot water extract of karin fruit, various herbal medicines, tocopherol acetate, glycyrrhizic acid and its derivatives or salts thereof, vitamin C, magnesium ascorbate phosphate, Suitable for whitening agents such as ascorbic acid glucoside, arbutin, kojic acid, sugars such as glucose, fructose, mannose, sucrose, trehalose, vitamin A derivatives such as retinoic acid, retinol, retinol acetate, retinol palmitate, etc. It can be formulated.
  • administration route and dosage form of the heparan sulfate production promoter of the present invention are not limited, and may be appropriately selected according to the application.
  • administration routes include topical administration (external skin use, etc.), oral administration, parenteral administration (intravenous administration, intraperitoneal administration, etc.), etc., but when used as an anti-aging agent or whitening agent, the skin It is preferable to use it as an external preparation.
  • a dosage form in the case of topical administration (external skin material), a solution system, a solubilization system, an emulsification system, a powder dispersion system, a water-oil two-layer system, a water-oil-powder three-layer system, etc., a patch agent, examples include ointments, creams, emulsions, lotions, gels, aerosols and the like.
  • solid preparations such as tablets, coated tablets, dragees, granules, powders, capsules (eg, hard or soft gelatin capsules), liquid preparations (solutions, suspensions) such as internal liquids, syrups, etc.
  • a form such as an injection solution may be mentioned.
  • whitening refers to the blackening of the skin due to accumulation of melanosomes in keratinocytes resulting from the activation and activation of melanocytes associated with degradation and reduction of heparan sulfate in the basement membrane through the promotion of heparan sulfate production. It means to suppress, improve stains, freckles and dullness.
  • the “whitening method” as used in the present invention means a cosmetic purpose unless otherwise specified, but in some cases, it may be a medical purpose.
  • anti-aging refers to skin changes associated with heparan sulfate-binding growth factor caused by degradation or decrease of heparan sulfate in basement membrane proteoglycan by aging or photoaging through promotion of heparan sulfate production, specifically Prevents and improves skin wrinkles, sagging and hardening by inhibiting epidermal differentiation abnormalities, dermal neovascularization, lymphatic dilation, and elastin degradation, and maintains an elastic, youthful and healthy skin condition Means that.
  • the “anti-aging method” as used in the present invention means a cosmetic purpose unless otherwise specified, but in some cases, it may be a medical purpose.
  • the heparan sulfate production promoter of the present invention is not limited to use as a whitening agent such as stain, freckles, dullness improvement, anti-aging purpose such as wrinkle improvement, use for promoting wound healing, heparan sulfate Can be used to treat, ameliorate, prevent, normalize various other conditions or symptoms associated with degradation, reduction, deficiency.
  • conditions or symptoms related to heparan sulfate degradation, reduction, or deficiency may include abnormalities in cell differentiation, cell growth regulation, cell morphogenesis, cell adhesion, mutual recognition, cell invasion, etc. Examples include cancer cell proliferation or metastasis, and angiogenesis.
  • Each well of a 24-well plate was seeded with 40,000 cells of HaCaT cells (source: German Cancer Research Center, Heidelberg, Germany), which were human epidermal cells, and cultured in DMEM medium containing 10% FBS for 3 days.
  • the medium of each well is a sample containing only 0.0005% of Madonna Lily Extract (source: Gatefosse) as an active ingredient in a dry weight, a sample containing only 0.001% of glucosamine hydrochloride (TSI Health Sciences), or Madonna. It was replaced with the same medium containing a sample containing a mixture of Lily extract 0.0005% and glucosamine hydrochloride 0.001%, and further cultured for 2 days.
  • a cell disruption solution having the following composition was added to each well, pipetted, and then frozen. 10 mmol / L Tris-HCl pH 7.4, 150 mmol / L NaCl, 2 mmol / L ethylenediaminetetraacetic acid, 250 lmol / L phenylmethylsulfonyl fluoride, 0.1 mmol / L N-ethylmaleimide, 0.3% Nonidet P40, 0.05% Triton X-100, 0.3% sodium deoxycholate, 0.1% sodium dodecyl sulfate, 0.1% BSA
  • Table 1 shows the raw data of the results shown in Figure 1 and the statistical processing results.
  • the raw data of the controls are 99.0565, 98.5847, 97.1694, and 105.189
  • the raw data of the Madonna Lily extract alone are 102.673, 100.157, 118.556, and 120.601, and the P value of Student's t-test (two-sided test) Becomes “0.108734”.
  • 0.108734> 0.05 that is, there is no significant difference between the two in terms of heparan sulfate production. Therefore, it is clear that Madonna lily extract itself has no effect on the production of heparan sulfate.
  • the heparan sulfate production promoter of the present invention can efficiently promote the production of heparan sulfate, it can improve, treat, prevent, and normalize various conditions or symptoms related to degradation, reduction, and deficiency of heparan sulfate.
  • Use for whitening such as blemishes, freckles, dullness improvement, anti-aging purposes such as wrinkle improvement, wound healing promotion, etc., eg cell differentiation, regulation of cell proliferation, cells Can be suitably used for normalization of abnormalities in cell morphogenesis, cell adhesion, mutual recognition, cell infiltration, and the like.

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  • Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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Abstract

L'invention concerne un promoteur de production d'héparane sulfate comprenant un mélange d'un extrait de lis blanc (Lilium Candidum) et de glucosamine.
PCT/JP2013/058825 2012-03-29 2013-03-26 Promoteur de la production d'héparane sulfate WO2013146797A1 (fr)

Applications Claiming Priority (2)

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JP2012-076968 2012-03-29
JP2012076968A JP5258993B1 (ja) 2012-03-29 2012-03-29 ヘパラン硫酸産生促進剤

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3026946A1 (fr) * 2014-10-08 2016-04-15 Laboratoires De Biologie Vegetale Yves Rocher Utilisation cosmetique d'un extrait de lilium candidum comme agent anti-rougeur et/ou pour ameliorer le lissage de la peau

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JP6718202B2 (ja) * 2014-06-20 2020-07-08 共栄化学工業株式会社 皮膚外用剤
JPWO2018225728A1 (ja) 2017-06-05 2020-04-02 昭和電工株式会社 グリコサミノグリカン産生促進剤及びグリコサミノグリカン産生促進用組成物

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JP2004083434A (ja) * 2002-08-23 2004-03-18 Rohto Pharmaceut Co Ltd コラーゲン合成促進剤
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JP2010018594A (ja) * 2008-07-14 2010-01-28 Noevir Co Ltd グリコサミノグリカン産生促進剤
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JPH08133945A (ja) * 1994-11-02 1996-05-28 Noevir Co Ltd 美白用皮膚外用剤
JP2003238343A (ja) * 2002-02-12 2003-08-27 Ichimaru Pharcos Co Ltd メラニン生成抑制剤又は化粧料組成物
JP2004083434A (ja) * 2002-08-23 2004-03-18 Rohto Pharmaceut Co Ltd コラーゲン合成促進剤
JP2004083432A (ja) * 2002-08-23 2004-03-18 Rohto Pharmaceut Co Ltd エラスターゼ阻害剤
JP2008195629A (ja) * 2007-02-09 2008-08-28 Naris Cosmetics Co Ltd 皮膚光老化改善剤
WO2009123215A1 (fr) * 2008-03-31 2009-10-08 株式会社資生堂 Préparation destinée à prévenir ou à améliorer les rides, devant être prise par voie orale, par injection ou par application cutanée externe, et procédé cosmétique
JP2011225564A (ja) * 2010-04-01 2011-11-10 Kyoei Kagaku Kogyo Kk 化粧料

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3026946A1 (fr) * 2014-10-08 2016-04-15 Laboratoires De Biologie Vegetale Yves Rocher Utilisation cosmetique d'un extrait de lilium candidum comme agent anti-rougeur et/ou pour ameliorer le lissage de la peau

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TW201343194A (zh) 2013-11-01
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