WO2013077574A1 - Composition topique contenant des dérivés de la théanine et destinée à être utilisée sur la peau - Google Patents

Composition topique contenant des dérivés de la théanine et destinée à être utilisée sur la peau Download PDF

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Publication number
WO2013077574A1
WO2013077574A1 PCT/KR2012/009377 KR2012009377W WO2013077574A1 WO 2013077574 A1 WO2013077574 A1 WO 2013077574A1 KR 2012009377 W KR2012009377 W KR 2012009377W WO 2013077574 A1 WO2013077574 A1 WO 2013077574A1
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WO
WIPO (PCT)
Prior art keywords
composition
skin
deanine
butyl
skin according
Prior art date
Application number
PCT/KR2012/009377
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English (en)
Korean (ko)
Inventor
이진영
유재원
최향태
김한별
이성훈
김지성
배지현
Original Assignee
주식회사 아모레퍼시픽
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
Priority claimed from KR1020120125391A external-priority patent/KR101956155B1/ko
Application filed by 주식회사 아모레퍼시픽 filed Critical 주식회사 아모레퍼시픽
Priority to CN201280057063.XA priority Critical patent/CN103957904B/zh
Priority to US14/360,371 priority patent/US9192791B2/en
Priority to JP2014543407A priority patent/JP6154819B2/ja
Publication of WO2013077574A1 publication Critical patent/WO2013077574A1/fr
Priority to HK14108405.6A priority patent/HK1194986A1/zh

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    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7016—Disaccharides, e.g. lactose, lactulose
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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

Definitions

  • the present invention relates to an external composition for skin containing a deanine derivative as an active ingredient, and more specifically, to an anti-aging, skin wrinkle improvement, skin barrier enhancement, skin immunity, skin moisturizing and
  • the present invention relates to a topical skin composition having an atopic improvement effect.
  • Theanine is an amino acid contained in green tea (Camellia sinesis), which is produced by the enzymatic reaction of glutamine (L-glutamine) and ethylamine (ethylamine). Occupy and are mainly present in the form of free amino acids. Deanine inhibits caffeine-induced excitability (Toxicol Lett. 2001 123 (2-3), 159-167, Biosci. Biotechnol. Biochem. 2000 Feb; 64 (2): 287-93). alpha-waves) to relieve tension (Nippon Nogeikagaku Kaishi 1998; 72: 153-157) and antistress actions such as suppressing stress-induced heart rate increases and reducing stress response factors (Biol Psychol. 2007 74 (1): 39-45).
  • the present inventors have found that anti-aging, skin wrinkle improvement, skin barrier enhancement, skin immunity enhancement, skin moisturizing and atopy improvement as a superior and discriminating physiological effect beyond the imitation of the effect of deanine nucleus due to the physiological activity of the deanine derivative. It has been found to have an effect and the present invention has been completed.
  • an object of the present invention is to provide an external composition for skin having excellent anti-aging, skin wrinkle improvement, skin barrier enhancement, skin immunity, skin moisturizing and atopic improvement effect by containing a deanine derivative as an active ingredient.
  • the present invention relates to an anti-aging, skin wrinkle improvement, skin barrier reinforcement, skin immunity enhancement, skin moisturizing and atopy improvement composition containing a deanine derivative as an active ingredient.
  • the external preparation composition for skin containing the deanine derivative of the present invention is more excellent and differentiates the physiological effect of the deanine nucleus due to the physiological activity of the deanine derivative as anti-aging, skin wrinkle improvement, skin barrier strengthening, It has the effect of strengthening skin immunity, moisturizing skin and improving atopic dermatitis.
  • 1 is a graph showing the expression rate of keratin 1 gene by deanine and the deanine derivative of the present invention.
  • Figure 2 is a graph showing the transglutaminase 1 gene expression rate by the deanine and the dean derivative of the present invention.
  • 3 is a graph showing the expression rate of filaggrin gene by deanine and the deanine derivative of the present invention.
  • Figure 4 is a result showing the intracellular calcium migration pattern when treated with deanine and the dean derivative of the present invention.
  • the deanine derivative used in the present invention has a structure represented by the following general formula (1) or (2).
  • R 1 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl
  • R2 is hydrogen, methyl, ethyl, propyl, isopropyl, n- Butyl, isobutyl and tert-butyl.
  • R 1 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl
  • R2 is hydrogen, methyl, ethyl, propyl, isopropyl, n- Butyl, isobutyl and tert-butyl.
  • the deanine derivative of the present invention is preferably contained in 0.0001 to 20% by weight based on the total weight of the composition. If it is less than 0.0001% by weight can not expect the desired effect, if it exceeds 20% by weight because it is not easy to control the viscosity of the cosmetic formulation.
  • the epidermal layer produces a complete stratum corneum through proliferation and differentiation and has homeostasis that drops off at the right time.
  • keratinocytes that divide in the basal layer are transformed into keratinocytes by synthesizing various proteins and lipids to form a keratinous layer.
  • Differentiation in the basal cells of the epidermis leads to the disappearance of the nucleus and intracellular organs, flattening and increasing the keratin intermediate fibers.
  • intracellular calcium concentration is important.
  • the proliferation of keratinocytes is promoted.
  • proliferation is suppressed and differentiation occurs.
  • the keratin protein constituting the keratin intermediate microfibers is expressed in keratin5, keratin 14 in the basal layer and keratin 1, keratin 10 in the granule layer.
  • keratin 1 is used as an indicator for epidermal differentiation.
  • Aging of the skin is divided into photo-aging and natural aging, all of which are different from the epidermis of young skin.
  • photoaging the thickness of the epidermis is abnormally thickened.
  • natural aging the thickness of the epidermis decreases and the formed keratinocytes do not fall off well. All of this is due to lack of normal turn-over of the epidermis and inadequate differentiation control.
  • These changes in epidermis are also involved in the formation of wrinkles in photoaging, according to a paper (JDS, 2001, Kambaytashi) that studies the mechanism of wrinkle formation by irradiating chronic low-dose UV radiation on hairless mice. According to the study, UV-irradiated skin produces wrinkles, and the amount of keratin 1 and filaggrin is significantly reduced.
  • the deanine derivative of the present invention has the effect of increasing the expression of keratin 1, this effect may result in the improvement of the homeostasis of the epidermal proliferation and differentiation, and through such homeostasis not only improve the natural aging skin but also ultraviolet light It can prevent or alleviate the formation of wrinkles.
  • One of the most important functions that skin performs is its function as a barrier against the free movement of various substances inside and outside the skin.
  • the skin barrier rapidly transitions from the granular layer to the stratum corneum, the keratin intermediate fine fibers are entangled to form a bundle of fibers, forming a stratum corneum that surrounds the inside of the cell membrane, cross-linking with protein components and other intracellular proteins in the stratum corneum
  • the cell membrane is replaced.
  • the keratin protein membrane and the keratin lipid membrane are combined to form a cornified envelope that forms the boundary of keratinocytes and completes the complete skin barrier structure.
  • Filaggrin promotes the binding between keratin microfibers in the stratum corneum and granules to strengthen the barrier.
  • Transglutaminase 1 crosslinks the various proteins necessary for the formation of the thick film.
  • the long chain hydroxyceramide is linked to proteins to contribute to the formation of keratin lipid membranes.
  • the deanine derivative of the present invention is excellent in increasing the expression of Filaggrin (Filaggrin), Transglutaminase 1 (Transglutaminase 1). Therefore, the deanine derivative of the present invention has the effect of strengthening the barrier function, which is the main function of the skin, by helping to form the keratin thickening membrane, thereby strengthening the physical protective film of the skin, thereby enhancing the innate immunity of the skin.
  • Filaggrin Filaggrin
  • Transglutaminase 1 Transglutaminase 1
  • Natural moisturizing factor is one of the important factors for skin moisturizing and consists of amino acids and its derivatives. It contains moisture and keeps skin moisturized.
  • the strengthening effect of the skin barrier is also a factor contributing to the skin moisturizing effect.
  • Filaggrin not only functions to strengthen the barrier by promoting the binding between keratin microfibers in the stratum corneum and granules, but also breaks down into amino acids to form natural moisturizing factors.
  • Filaggrin gene abnormality may be associated with the outbreak of atopic dermatitis.
  • filaggrin not only enhances epidermal barrier function but also acts as a natural moisturizing factor, and is also involved in atopic dermatitis.
  • the deanine derivative of the present invention increases the expression of filaggrin as described above, and due to this effect, it can show skin moisturizing effect through increasing the natural moisturizing factor along with enhancing epidermal barrier function, and atopy due to the decrease of filaggrin. It has the effect of alleviating the symptoms of dermatitis.
  • the cosmetic composition is not particularly limited in formulation, and may be appropriately selected as desired.
  • skin lotion, skin softener, skin toner, astringent, lotion, milk lotion, moisturizing lotion, nutrition lotion, massage cream, nutrition cream, moisturizing cream, hand cream, foundation, essence, nutrition essence, pack, soap, cleansing It may be prepared in any one or more formulations selected from the group consisting of foam, cleansing lotion, cleansing cream, body lotion and body cleanser, but is not limited thereto.
  • the formulation of the present invention is a paste, cream or gel
  • animal carriers vegetable fibers, waxes, paraffins, starches, tracantes, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc or zinc oxide, etc.
  • carrier components can be used as carrier components.
  • lactose When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, and especially in the case of spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether.
  • a solvent, solvating or emulsifying agent is used as the carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 Fatty acid esters of, 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.
  • liquid carrier diluents such as water, ethanol or propylene glycol
  • suspension agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline Cellulose, aluminum metahydroxy, bentonite, agar or tracant and the like can be used.
  • the carrier component is aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid amide.
  • Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, linolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.
  • the cosmetic composition may further include functional additives and components included in the general cosmetic composition in addition to the added deanine derivative.
  • the functional additive may include a component selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymer polysaccharides, sphingolipids, and seaweed extracts.
  • Human neonatal epithelial keratinocytes (HEK; Lonza, NHEK-Neo-Neonatal Normal Human Epidermal Keratinocytes, Pooled) were dispensed in 6-well medium (KBM-gold, Lonza) each at 1 ⁇ 10 5 for 24 hours at 37 ° C. The culture was discarded, and the deanine derivatives were treated with a medium containing 100 ⁇ M and 500 ⁇ M (KBM-gold, Lonza, respectively) and cultured at 37 ° C. for 5 days.
  • quantitative real-time PCR was performed using a probe (TaqManTM fluorogenic probe, Hs00196158_m1), and the expression patterns of Keratin 1 were observed, and the results are shown in FIG. 1.
  • 100 ⁇ M and 500 ⁇ M deanine (Sigma, T6576) were used instead of the untreated group and the deanine derivative, respectively.
  • Transglutaminase 1 gene expression was confirmed in human neonatal epithelial keratinocytes (HEK)
  • Human neonatal epithelial keratinocytes (HEK; Lonza, NHEK-Neo-Neonatal Normal Human Epidermal Keratinocytes, Pooled) were dispensed in 6-well medium (KBM-gold, Lonza) each at 1 ⁇ 10 5 for 24 hours at 37 ° C. The culture was discarded, and the deanine derivatives were treated with a medium containing 100 ⁇ M and 500 ⁇ M (KBM-gold, Lonza, respectively) and cultured at 37 ° C. for 5 days.
  • RNeasy mini kit qiagen
  • cDNA was synthesized by RT-PCR with Superscript III kit invitrogen.
  • the expression pattern of transglutaminase was observed by performing quantitative real-time PCR using a probe (TaqManTM fluorogenic probe, Hs00165929_m1). Shown in As a control, 100 ⁇ M and 500 ⁇ M deanine (Sigma, T6576) were used instead of the untreated group and the deanine derivative, respectively.
  • Human neonatal epithelial keratinocytes (HEK; Lonza, NHEK-Neo-Neonatal Normal Human Epidermal Keratinocytes, Pooled) were dispensed in 6-well medium (KBM-gold, Lonza) each at 1 ⁇ 10 5 for 24 hours at 37 ° C. The culture was discarded, and the deanine derivatives were treated with a medium containing 100 ⁇ M and 500 ⁇ M (KBM-gold, Lonza, respectively) and cultured at 37 ° C. for 5 days.
  • a quantitative real-time PCR was performed using a probe (TaqManTM fluorogenic probe, Hs00856927_g1), and the expression patterns of transglutaminase were observed.
  • FIG. 3 As a control, 100 ⁇ M and 500 ⁇ M deanine (Sigma, T6576) were used instead of the untreated group and the deanine derivative, respectively.
  • Stabilized human neonatal epithelial keratinocytes (HEK; Lonza, NHEK-Neo-Neonatal Normal Human Epidermal Keratinocytes, Pooled) were obtained by 2x10 4 in confocal dishes, 2.5 mM deanine and deanine derivative 0.5. After 5 minutes of mM treatment, 1 ⁇ m fluo 3-AM was treated for 15 minutes to detect intracellular calcium fluoride by confocal microscopy (Nikon, Japan). It evaluated, and the result is shown in FIG.
  • Example 1 To prepare Example 1 and Comparative Example 1 according to the composition of Table 1.
  • Example 2 when treating Example 1 containing a deanine derivative, it can be seen that the transdermal moisture loss returns to normal at a rapid rate and the barrier damage is recovered.
  • Example 2 Comparative Example 2 Purified water To 100 To 100 Deanine derivatives One - Vegetable Cured Oil 1.50 1.50 Stearic acid 0.60 0.60 Glycerol Stearate 1.00 1.00 Stearyl alcohol 2.00 2.00 Polyglyceryl-10 Pentastearate & Behenyl Alcohol & Sodium Stearoyl Lactylate 1.00 1.00 Arakidil Behenyl Alcohol & Arakidil Glucoside 1.00 1.00 Cetylaryl Alcohol & Cetearyl Glucoside 2.00 2.00 PEG-100 Stearate & Glycerolate & Propylene Glycol 1.50 1.50 Caprylic / Carric Triglycerides 11.00 11.00 Cyclomedicon 6.00 6.00 Preservative, incense Quantity Quantity Triethanol amine 0.1 0.1 0.1
  • Comparative Example 2 shows a water increase rate of about 30% up to 4 weeks after the application, but after stopping the application, the amount of skin moisture decreases, but it contains the deanine derivative.
  • the skin moisture increase rate is more than 30% even after the application is stopped.
  • the skin moisturizing effect of the composition according to the invention containing the deanine derivative is very excellent.
  • the external preparation composition for skin which has an effect of strengthening immunity, moisturizing skin and improving atopic dermatitis can be provided.

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Abstract

La présente invention porte sur une composition topique destinée à être utilisée sur la peau et contenant en tant que composants actifs des dérivés de la théanine, notamment sur une composition topique utilisée sur la peau et possédant des effets anti-âge, réparateur anti-rides, d'amélioration des propriétés barrières de la peau, de renforcement de l'immunité et d'hydratation de la peau et de soulagement de l'atopie grâce à sa teneur en dérivés de théanine utilisés en tant que composants actifs.
PCT/KR2012/009377 2011-11-23 2012-11-08 Composition topique contenant des dérivés de la théanine et destinée à être utilisée sur la peau WO2013077574A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201280057063.XA CN103957904B (zh) 2011-11-23 2012-11-08 含有茶氨酸衍生物的皮肤外用剂组合物
US14/360,371 US9192791B2 (en) 2011-11-23 2012-11-08 Topical composition containing theanine derivatives for use on skin
JP2014543407A JP6154819B2 (ja) 2011-11-23 2012-11-08 デアニン誘導体を含有する皮膚外用剤組成物
HK14108405.6A HK1194986A1 (zh) 2011-11-23 2014-08-18 含有茶氨酸衍生物的皮膚外用劑組合物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2011-0122748 2011-11-23
KR20110122748 2011-11-23
KR1020120125391A KR101956155B1 (ko) 2011-11-23 2012-11-07 데아닌 유도체를 함유하는 피부 외용제 조성물
KR10-2012-0125391 2012-11-07

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WO2013077574A1 true WO2013077574A1 (fr) 2013-05-30

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113925812A (zh) * 2021-11-12 2022-01-14 广州睿森生物科技有限公司 一种促进睡眠和肌肤修复的功效组合物及其在化妆品中的应用
CN116715706A (zh) * 2023-06-08 2023-09-08 安徽农业大学 一种延长茶氨酸体内半衰期的化学修饰方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100513616B1 (ko) * 2003-04-24 2005-09-09 주식회사 태평양 녹차 성분을 함유하는 피부 외용제 조성물
US20080009505A1 (en) * 2006-07-04 2008-01-10 Conopco Inc. D/B/A Unilever Theanine derivatives, uses thereof and processes for the manufacture thereof
KR20090064743A (ko) * 2007-12-17 2009-06-22 (주)아모레퍼시픽 데아닌을 함유하는 프롤린 리사이클링 촉진용 피부 외용제또는 미용 식품 조성물

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100513616B1 (ko) * 2003-04-24 2005-09-09 주식회사 태평양 녹차 성분을 함유하는 피부 외용제 조성물
US20080009505A1 (en) * 2006-07-04 2008-01-10 Conopco Inc. D/B/A Unilever Theanine derivatives, uses thereof and processes for the manufacture thereof
KR20090064743A (ko) * 2007-12-17 2009-06-22 (주)아모레퍼시픽 데아닌을 함유하는 프롤린 리사이클링 촉진용 피부 외용제또는 미용 식품 조성물

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113925812A (zh) * 2021-11-12 2022-01-14 广州睿森生物科技有限公司 一种促进睡眠和肌肤修复的功效组合物及其在化妆品中的应用
CN113925812B (zh) * 2021-11-12 2023-08-11 广州睿森生物科技有限公司 一种促进睡眠和肌肤修复的功效组合物及其在化妆品中的应用
CN116715706A (zh) * 2023-06-08 2023-09-08 安徽农业大学 一种延长茶氨酸体内半衰期的化学修饰方法
CN116715706B (zh) * 2023-06-08 2024-02-06 安徽农业大学 一种延长茶氨酸体内半衰期的化学修饰方法

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