WO2004045573A1 - Composition a base de n-acetylphytosphingosine pour blanchiment de la peau - Google Patents

Composition a base de n-acetylphytosphingosine pour blanchiment de la peau Download PDF

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Publication number
WO2004045573A1
WO2004045573A1 PCT/KR2003/002474 KR0302474W WO2004045573A1 WO 2004045573 A1 WO2004045573 A1 WO 2004045573A1 KR 0302474 W KR0302474 W KR 0302474W WO 2004045573 A1 WO2004045573 A1 WO 2004045573A1
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WO
WIPO (PCT)
Prior art keywords
acetylphytosphingosine
composition
skin
tyrosinase
melanin
Prior art date
Application number
PCT/KR2003/002474
Other languages
English (en)
Inventor
Chang Seo Park
Jin Wook Kim
You-A Hwang
Mee Kyung Park
Young Sook Yoo
She Yoon Yi
Original Assignee
Doosan Corporation
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 Doosan Corporation filed Critical Doosan Corporation
Priority to AU2003280880A priority Critical patent/AU2003280880A1/en
Publication of WO2004045573A1 publication Critical patent/WO2004045573A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • 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
    • A61K31/13—Amines
    • A61K31/133—Amines having hydroxy groups, e.g. sphingosine
    • 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
    • A61K8/42—Amides
    • 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
    • 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 a sphingolipid inhibiting the synthesis of melanin in the melanocytes which play a key role in determining the color of human skin. More particularly, the present invention relates to the effective use of N- acetylphytosphingosine, which is a acetylated derivative of phytosphingosine, in whitening cosmetics and pharmaceuticals for the prevention and treatment of discoloration, freckles, senile chromelasma and hyperpigmentation due to the potential inhibitory functions of N-acetylphytosphingosine on melanin synthesis and tyrosinase activity.
  • N- acetylphytosphingosine which is a acetylated derivative of phytosphingosine
  • sphingolipids are involved in intracellular signal transmission and play a critical role in cellular growth, differentiation and death. It is also known that ceramides, which are the most widely found lipids in the skin, inhibit moisture vaporization from the skin and prevent the progress of aging and skin diseases. Further, phytosphingosine as a long-chain base of the sphingolipids, or an acetylated derivative thereof is known to have excellent antibacterial and anti- inflammatory effects and is involved in ceramide biosynthesis within the skin. Although a great deal of research on ceramide and sphingolipid derivatives in the keratinocytes has been conducted, no research has been conducted on the synthesis of melanin.
  • Kim et al. first conducted their research associated with melanin synthesis using sphingolipid derivatives (D. S. Kim, Cellular signaling 14 (2002) 779-785). As a result, they found that a ceramide derivative (C2 ceramide) exhibits better inhibitory effects on melanin synthesis at a concentration of 1-1 O ⁇ M than kojic acid, and reported the finding that sphingosine-1 -phosphate inhibits melanin synthesis by regulating the signal transmission processes of melanin synthesis.
  • the present invention has been made in view of the above problems, and it is an object of the present invention to provide a method for inhibiting the activity of tyrosinase using a sphingolipid derivative, thereby preventing melanin hyperpigmentation of the skin and thus preventing skin pigment-related symptoms such as discoloration, freckles, senile chromelasma and hyperpigmentation.
  • composition for inhibiting the activity of tyrosinase which comprises N- acetylphytosphingosine as an active ingredient, represented by Formula 1 below:
  • composition for peeling hype ⁇ igmented skin cells which comprises N- acetylphytosphingosine of Formula 1 as an active ingredient.
  • compositions for skin whitening which comprises N-acetylphytosphingosine of Formula 1 as an active ingredient.
  • the present invention is characterized in that the compositions are those for external use, in particular, cosmetic compositions, and are preferably prepared into cosmetic formulations such as softening lotions, nutritive lotions, massage creams, gels, nutritive creams, packs and skin patches for external use.
  • compositions of the present invention preferably comprise N- acetylphytosphingosine in an amount of 0.005-10% by weight.
  • compositions of the present invention may be prepared into formulations for transdermal administration such as lotions, ointments, gels, creams, patches and nebulas.
  • Fig. 1 is the result of RT-PCR (reverse transcription polymerase chain reaction) analysis showing the influence of N-acetylphytosphingosine used in the present invention on the expression of the TRP-2 (tyrosinase related protein 2) gene;
  • Fig. 2 is the result of RT-PCR (reverse transcription polymerase chain reaction) analysis showing the influence of N-acetylphytosphingosine used in the present invention on the expression of the TRP-1 (tyrosinase related protein 1) gene; and
  • Fig. 3 is the result of RT-PCR (reverse transcription polymerase chain reaction) analysis showing the influence of N-acetylphytosphingosine used in the present invention on the expression of the tyrosinase gene.
  • the color of human skin is determined by various skin components. Of these skin components, melanin produced in the melanocytes is most responsible for skin color.
  • the skin melanocytes are regulated by various genetic characteristics according to race so as to exhibit the characteristic skin colors of different races.
  • melanin is increasingly synthesized, migrates to adjacent keratinocytes through the melanosome and is finally peeled off from the skin (desquamation).
  • Melanin is synthesized in the melanosome of the melanocyte, which originates from the endoplasmic reticulum. Due to the internal structure of the melanosome, the synthesized melanin is regularly accumulated in the melanosome.
  • Tyrosinase is an enzyme converting tyrosine to melanin. Tyrosinase is synthesized in the Golgi apparatus and then migrates to the melanosome. In premature melanosomes, while tyrosine goes through oxidation by the action of the tyrosinase, the biosynthesis of melanin begins. The premature melanosomes where melanin synthesis begins undergo 4 growth stages until they develop into mature melanosomes.
  • the mature melanosomes migrate to adjacent keratinocytes.
  • the color of human skin is determined by the number, size and distribution of melanin in the keratinocytes.
  • the melanosomes migrate from the stratum basale of the epidermis to the keratinocytes and then migrate to the stratum corneum of the skin while protecting the keratinocytes. During migration, the melanosomes are degraded, but the melanin is not degraded and is finally desquamated from the skin.
  • the tyrosinase playing the most important role in the biosynthesis of melanin is synthesized in the Golgi apparatus and undergoes glycosylation.
  • glycosylated tyrosinase migrates to the melanosomes, it is converted to its active state by physphorylation.
  • Melanin synthesis begins with the oxidation of tyrosine as the substrate by the activated tyrosinase.
  • the tyrosine is converted to dihydroxyphenylalanine (DOPA) by tyrosinase, and then converted to DOPA quinone by the same enzyme.
  • DOPA quinone binds with glutathione or cysteines to produce cysteinyl DOPA, which is further converted to pheomelanin.
  • the DOPA quinone is converted to DOPA chrome to produce 5,6-dihydroxyindole, which is converted to indole-5,6-quinone by the action of tyrosinase.
  • the indole-5,6-quinone is finally converted to eumelanin.
  • tyrosinase is involved not only in the initial synthetic step but also in the final synthetic step of melanin and thus plays the most important role in the synthesis of melanin. Accordingly, many substances having inhibitory effects on melanin synthesis have been developed focusing on the inhibition of tyrosinase activity.
  • the compositions of the present invention comprise N-acetylphytosphingosine as an active ingredient to inhibit tyrosinase activity.
  • the eumelanin and pheomelanin synthesized in the melanocytes are present in various ratios depending on race or body sites. These ratios between the eumelanin and pheomelanin represent different colors of human skin.
  • the eumelanin is black or brown, and the pheomelanin is orange, both of which are synthesized from two amino acids, i.e. tyrosine and cysteine, respectively.
  • the melanin functions to protect the skin from UV light and to protect skin organs lying beneath the hypodermis.
  • the melanin also captures reactive oxygen and free radicals and thus protects proteins and nucleic acids.
  • abnormal formation of melanin and pigmentation of the skin cause skin conditions such as discoloration, freckles and skin pigment anomalies.
  • compositions of the present invention comprising 0.005-10% by weight of N-acetylphytosphingosine as an active ingredient are pharmaceutical compositions for transdermal administration, they are preferably administered in an appropriate amount twice daily.
  • the present inventors measured melanin synthesis and tyrosinase activity using phytosphingosine derivatives, which can be easily prepared by yeast fermentation, and as a result discovered that an acetylated derivative, N-acetylphytosphingosine among the phytosphingosine derivatives exhibits better inhibitory effects on melanin synthesis and tyrosinase activity than kojic acid, even at much lower concentration (1/1,000).
  • N-acetylphytosphingosine exhibits better inhibitory effects on melanin synthesis and tyrosinase activity than C2 ceramide (having a sphingosine backbone structure) and sphingosine-1 -phosphate reported by Kim et al. Furthermore, the present inventors found that when human skin cells were artificially hype ⁇ igmented and then a cream prepared from the composition according to the present invention was applied on the hype ⁇ igmented skin cells, the hype ⁇ igmented skin cells were peeled off in a short time.
  • Example 1 Some preferred creams (Examples 1 to 4) containing N-acetylphytosphingosine at various concentrations were prepared to have the compositions shown in Table 1 below.
  • a cream of Comparative Example 1 was prepared as a negative control to have the composition shown in Table 1 below.
  • Phytosphingosine, N-acetylphytosphingosine and tetraacetylphytosphingosine were chosen as sphingolipids, and their inhibitory effect on melanin synthesis were evaluated.
  • the phytosphingosine derivatives were synthesized by acetylation of phytosphingosine prepared by yeast fermentation.
  • the sphingolipids were dissolved in DMSO (dimethylsulfoxide) before use.
  • DMSO dimethylsulfoxide
  • B16F10 mouse melanoma cells were used as a cell line used in the present invention.
  • the cell line was incubated in DMEM (Dulbecco's Modified Eagle Medium) in a 5% CO 2 incubator at 37°C supplemented with 10% FBS (fetal bovine serum) and antibiotics.
  • DMEM Dulbecco's Modified Eagle Medium
  • the melanin content was measured in accordance with the following procedure. First, the B16F10 mouse melanoma cells were inoculated on a 24- ell multi-plate in an amount of 2 x 10 3 cells/well, and then incubated in a 5% CO 2 incubator for 24 hours. Following pre-incubation, the sphingolipids were diluted in serum-free DMEM (Dulbecco's Modified Eagle Medium). After the cell line was treated with the compounds at various concentrations, it was cultured for 96 hours. The cultures were washed with PBS, and 0.85N KOH was added thereto. After the resulting cultures were dissolved by sonication, the light absorbance was measured at 475nm to determine the total melanin content.
  • Eumelanin and pheomelanin were fractionally quantified using high speed chromatography. The obtained values were expressed as percentage relative to the control. The results are shown in Table 2 below. The values shown in Table 2 represent the formation rates of melanin, i.e. formation percentages (%) relative to that of the untreated group.
  • DMEM Dulbecco's Modified Eagle Medium
  • the B16F10 mouse melanoma cells were inoculated on a 96- well multi-plate in an amount of 1 x 10 4 cells/well, and then incubated in a 5% CO 2 incubator for 24 hours. Following pre-incubation, the test compounds were diluted in serum-free DMEM (Dulbecco's Modified Eagle Medium). After the cell line was treated with the compounds at various concentrations, it was cultured for 96 hours.
  • FBS fetal bovine serum
  • TRP-1 tyrosinase related protein 1
  • TRP-2 tyrosinase related protein 2
  • RT-PCR reverse transcription polymerase chain reaction
  • the results obtained associated with TRP-2 are shown in Fig. 1.
  • Lane 1 represents the results obtained before culture
  • lane 2 represents the results obtained after treating with l ⁇ M N-acetylphytosphingosine for 48 hours
  • lane 3 represents the results obtained after treating with 5 ⁇ M N-acetylphytosphingosine for 48 hours
  • lane 4 represents the results obtained after treating with l ⁇ M N-acetylphytosphingosine for 72 hours
  • lane 5 represents the results obtained after treating with 5 ⁇ M N- acetylphytosphingosine for 72 hours, respectively.
  • the results obtained associated with TRP-1 are shown in Fig. 2. As shown in
  • lane 1 represents the results obtained before culture
  • lane 2 represents the results obtained after treating with l ⁇ M N-acetylphytosphingosine for 48 hours
  • lane 3 represents the results obtained after treating with 5 ⁇ M N-acetylphytosphingosine for 48 hours
  • lane 4 represents the results obtained after treating with l ⁇ M N- acetylphytosphingosine for 72 hours
  • lane 5 represents the results obtained after treating with 5 ⁇ M N-acetylphytosphingosine for 72 hours, respectively.
  • lane 1 represents the results obtained before culture
  • lane 2 represents the results obtained after treating with l ⁇ M N-acetylphytosphingosine for 48 hours
  • lane 3 represents the results obtained after treating with 5 ⁇ M N-acetylphytosphingosine for 48 hours
  • lane 4 represents the results obtained after treating with l ⁇ M N- acetylphytosphingosine for 72 hours
  • lane 5 represents the results obtained after treating with 5 ⁇ M N-acetylphytosphingosine for 72 hours, respectively.
  • N-acetylphytosphingosine did not inhibit the expression of the tyrosinase gene. Based on this finding, it is expected that N- acetylphytosphingosine would have direct inhibitory effects on tyrosinase activity.
  • ⁇ L L value measured on final day after application of a test compound - L value before application of the test compound
  • N-acetylphytosphingosine used in the present invention inhibits melanin synthesis and tyrosinase activity, skin pigment- related symptoms such as discoloration, freckles, senile chromelasma and hype ⁇ igmentation can be prevented.
  • N-acetylphytosphingosine peels hype ⁇ igmented skin cells, skin pigment-related symptoms such as discoloration, freckles, senile chromelasma and hype ⁇ igmentation can be treated.
  • N-acetylphytosphingosine has peeling effects on hype ⁇ igmented skin cells as well as whitening effects, it can be effectively used in the cosmetic and pharmaceutical industries.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Dermatology (AREA)
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  • Biophysics (AREA)
  • Molecular Biology (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Abstract

La présente invention concerne une composition à base de N-acétylphytosphingosine qui favorise le blanchiment de la peau par inhibition de l'activité de la tyrosinase ou par desquamation de cellules cutanées hyperpigmentées. Cette composition empêche efficacement la synthèse de la mélanine dans la mesure où elle réprime l'activité de la tyrosinase et par là même empêche l'apparition de symptômes en rapport avec les pigments de la peau tels que décoloration, taches de rousseur, « chromelasme » (sic) sénile ou hyperpigmentation. La composition convient également pour le traitement de symptômes associés aux pigments de la peau tels que décoloration, taches de rousseur, chromelasme sénile ou hyperpigmentation par desquamation des cellules cutanées hyperpigmentées, De plus, cette composition trouve des application dans les domaines cosmétique et pharmaceutique.
PCT/KR2003/002474 2002-11-19 2003-11-18 Composition a base de n-acetylphytosphingosine pour blanchiment de la peau WO2004045573A1 (fr)

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AU2003280880A AU2003280880A1 (en) 2002-11-19 2003-11-18 Composition for skin whitening containing n-acetylophytosphingosine

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2894961A1 (fr) * 2005-12-16 2007-06-22 Oreal Utilisation de ceramides pour depigmenter la peau
FR2963233A1 (fr) * 2010-07-28 2012-02-03 Oreal Procede pour diminuer les hyperpigmentations post-reactionnelles
WO2014088296A1 (fr) * 2012-12-04 2014-06-12 재단법인 경기과학기술진흥원 Composition de blanchiment de la peau employant xylosma congesta
WO2022171292A1 (fr) 2021-02-12 2022-08-18 Symrise Ag Médicament pour la prévention et le traitement de l'hyperpigmentation

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KR20050051862A (ko) * 2003-11-28 2005-06-02 주식회사 두산 스핑고지질-폴리에틸렌글리콜 중합체 및 그를 함유한 피부외용제 조성물
KR20200097131A (ko) 2019-02-07 2020-08-18 주식회사 엘씨에스바이오텍 신규 스핑고지질 유도체, 그 제조방법 및 이를 함유하는 조성물

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KR20020027919A (ko) * 2000-10-06 2002-04-15 박경찬 스핑고리피드 또는 그 대사산물을 함유하는 미백 화장료조성물

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2894961A1 (fr) * 2005-12-16 2007-06-22 Oreal Utilisation de ceramides pour depigmenter la peau
WO2007071875A2 (fr) * 2005-12-16 2007-06-28 L'oréal Utilisation de céramides pour dépigmenter la peau
WO2007071875A3 (fr) * 2005-12-16 2007-10-11 Oreal Utilisation de céramides pour dépigmenter la peau
JP2009519306A (ja) * 2005-12-16 2009-05-14 ロレアル 皮膚の色素除去のためのセラミドの使用
US8268805B2 (en) 2005-12-16 2012-09-18 L'oreal Use of ceramides for depigmenting the skin
FR2963233A1 (fr) * 2010-07-28 2012-02-03 Oreal Procede pour diminuer les hyperpigmentations post-reactionnelles
WO2012022899A2 (fr) 2010-07-28 2012-02-23 L'oreal Procédé pour diminuer les hyperpigmentations post-réactionnelles
WO2012022899A3 (fr) * 2010-07-28 2012-04-12 L'oreal Procédé pour diminuer les hyperpigmentations post-réactionnelles
WO2014088296A1 (fr) * 2012-12-04 2014-06-12 재단법인 경기과학기술진흥원 Composition de blanchiment de la peau employant xylosma congesta
WO2022171292A1 (fr) 2021-02-12 2022-08-18 Symrise Ag Médicament pour la prévention et le traitement de l'hyperpigmentation

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AU2003280880A1 (en) 2004-06-15
KR20040043645A (ko) 2004-05-24

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