US20090012155A1 - Composition Of Skin External Application For Anti-Aging - Google Patents

Composition Of Skin External Application For Anti-Aging Download PDF

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US20090012155A1
US20090012155A1 US12/064,887 US6488706A US2009012155A1 US 20090012155 A1 US20090012155 A1 US 20090012155A1 US 6488706 A US6488706 A US 6488706A US 2009012155 A1 US2009012155 A1 US 2009012155A1
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composition
skin
green tea
catechin
theanine
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US12/064,887
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Inventor
Jeong Ki Kim
Hyun Jung Shin
Su Nam Kim
Byeong Gon Lee
Ih Seop Chang
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Amorepacific Corp
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Amorepacific Corp
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Priority claimed from KR1020050083665A external-priority patent/KR101219293B1/ko
Priority claimed from KR1020050083667A external-priority patent/KR101219296B1/ko
Priority claimed from KR1020060021797A external-priority patent/KR20070091964A/ko
Application filed by Amorepacific Corp filed Critical Amorepacific Corp
Assigned to AMOREPACIFIC CORPORATION reassignment AMOREPACIFIC CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHANG, IH SEOP, KIM, JEONG KI, KIM, SU NAM, LEE, BYEONG GON, SHIN, HYUN JUNG
Publication of US20090012155A1 publication Critical patent/US20090012155A1/en
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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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions

Definitions

  • the present invention relates to an anti-aging composition for external use on skin, and more particularly, to an anti-aging composition for external use on skin comprising at least one of catechins and flavonols as an active ingredient to inhibit decomposition and promote generation or protection at the dermis-epidermis junction.
  • the skin which is a primary barrier of the human body protects organs in the body from change of temperature and humidity and stimulation from the outer environment such as UV rays and pollutants and plays an important role for homeostasis such as regulation of body temperature.
  • excessive physical and chemical stimulation from the outside, UV rays, stress and malnutrition may deteriorate normal functions of the skin and promote skin aging such as elasticity loss, keratinization and wrinkle formation.
  • the dermis-epidermis junction is severely damaged by UV irradiation.
  • Gelatinase (MMP-2, MMP-9) is an enzyme to decompose type IV collagen, type VII collagen and other extracellular matrix which are components of the dermis-epidermis junction.
  • MMP-2 and MMP-9 are detected in the UV-exposed epidermis.
  • the activity of gelatinase in the skin is detected near epidermal stratum basalis and stratum spinosum in the chilled forehead skin.
  • gelatinase is detected in the epidermis of the UV-exposed skin such as the face.
  • UV rays induce formation of gelatinase in the epidermal stratum basalis, a part of them participates in destruction of the dermis-epidermis junction and the rest stays in the epidermis and reaches the epidermis.
  • the dermis-epidermis junction When the dermis-epidermis junction is damaged, wrinkle is formed by flattering of the junction, multiplication and heat insulation, and the skin is sagged and is apt to be damaged. Also, by the loss of the characteristic barrier function, the dermis-epidermis junction fails to filter pollutants from the outer environment, whereby noxious materials can readily infiltrate to the dermis and the skin can be damaged. In order to recover the damaged dermis-epidermis junction or maintain it at the healthy state, its components should be maintained as they are. The components which is known that whose biosynthesis is decreased, as the age increases, are type IV collagen, type VII collagen and laminin 10/11.
  • Laminin 5 does not shown change while the components whose biosynthesis is increased are gelatinase (MMP-2 and MMP-9) which is known to be associated with decomposition (Lavker et. Al. J. Invest. Derm. 1979, 73:59-65, Pouliot et. Al. Exp. Dermatol. 2002, 11:387-397).
  • the present inventors have searched a method for effectively controlling various factors affecting skin aging and found that various change of the junction between the dermis and epidermis caused by natural aging and photo-aging, including degeneration, heat insulation and multiplication, can be prevented or recovered by using a composition for external use on skin comprising at least one of catechins and flavonols which are extracted from green tea.
  • a composition for external use on skin comprising at least one of catechins and flavonols which are extracted from green tea.
  • catechins or flavonols from the green tea extract can inhibit the decomposition and promote the generation at the dermis-epidermis junction, thereby strengthening the bonding between the dermis and the epidermis, whereby they can be used in cosmetic preparations and pharmaceutical compositions for anti-aging.
  • composition for external use on skin with excellent anti-aging effect comprising at least one of catechins and flavonols as an active ingredient.
  • composition for external use on skin with excellent anti-aging effect comprising theanine in addition to the above-described components from the green tea extract as an active ingredient.
  • composition for external use on skin comprising at least one of catechins and flavonols of the green tea extract as an active ingredient can reduce biosynthesis of gelatinase (MMP-2, MMP-9) and increase biosynthesis of type IV collagen, type VII collagen and laminin 10/11 to inhibit the decomposition and promote the generation at the dermis-epidermis junction, thereby protect the dermis-epidermis junction.
  • MMP-2 gelatinase
  • MMP-9 type IV collagen, type VII collagen and laminin 10/11 to inhibit the decomposition and promote the generation at the dermis-epidermis junction, thereby protect the dermis-epidermis junction.
  • FIG. 1 is a graph showing the result of the measurement of MMP-1 biosynthesis by various test samples.
  • composition for external use on skin comprises at least one of catechins and flavonols from the green tea extract as an active ingredient.
  • the catechins used according to the present invention is extracted from green tea and includes epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), epicatechin gallate (ECG), catechin gallate (CG), epigallocatechin (EGC), gallocatechin (GC), ( ⁇ )epicatechin (EC), (+)epicatechin (EC), ( ⁇ )catechin (CA) and (+)catechin (CA), with preference being epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), epicatechin gallate (ECG) and catechin gallate (CG) expressed by the following formulae 1 to 4.
  • the flavonols used according to the present invention is extracted from green tea and includes quercetin, kaempferol and myricetin, with preference being kaempferol and myricetin, more preference being myricetin.
  • the composition for external use according to the present invention comprises 0.001 to 10 wt %, preferably 0.01 to 5 wt % of the active ingredient, based on the total weight of the composition. If the content is less than 0.001 wt %, it is difficult to expect significant effects, while if the content excesses 10 wt %, it is impossible to formulate the composition.
  • composition for external use on skin further comprising theanine as an active ingredient, in addition to the component from the green tea extract.
  • Theanine is one of amino acids giving savory taste of green tea and has effect of inhibiting excitation caused by caffeine. In fact, it has been observed that human bodies intaking theanine shows increase in a wave appearance showing stabilized and tranquil state of mind (Nippon Nogeikagaku Kaishi, 1998, 72 (2): 153-157).
  • the theanine used according to the present invention may be one selected from L-form which is extracted from green tea, and L-theanine, D-theanine and DL-theanine which are chemically synthesized, or may be prepared other methods.
  • the composition for external use on skin comprises theanine in combination with at least one of catechins and flavonols from the green tea extract
  • the content of at least one of catechins and flavonols from the green tea extract in the composition is determined from the result of in vitro experiments and in vivo experiments and is preferably 0.0004 to 0.025 wt %, based on the total weight of the composition.
  • the content is less than 0.0004 wt % the component cannot act as an effective ingredient, while if the content excesses 0.025 wt % the improvement of the symptoms is rather deteriorated.
  • the content of theanine is determined from the result of in vitro experiments and in vivo experiments and is preferably 0.008 to 2.5 wt %, based on the total weight of the composition.
  • the content is less than 0.008 wt %, the component cannot act as an effective ingredient, while if the content excesses 2.5 wt % the improvement of the symptoms is rather deteriorated.
  • composition for external use on skin comprises the green tea extract and theanine in a predetermined mixing ratio.
  • catechin to theanine is 1:20 to 1:100 for optimal anti-aging effect of skin.
  • composition for external use on skin prevent and improve skin aging through promotion of collagen synthesis, improvement skin elasticity and improvement of skin wrinkles.
  • composition for external use on skin activates peroxisome proliferator-activated receptor-alpha (PPAR- ⁇ ) to inhibit tumor necrosis factor ⁇ (TNF- ⁇ ) and biosynthesis of MMP-1, thereby inhibiting skin aging.
  • PPAR- ⁇ peroxisome proliferator-activated receptor-alpha
  • Peroxisome is one of organelles providing causes of abnormal metabolic functions leading hyperlipidemia, diabetes and obesity. For a long time, this organelle has been considered to play a tiny role in the cell. However, according to many recent studies, it has been reported that it plays very important role in control of cell multiplication/differentiation, control of inflammatory mediators and the like and widely affects metabolism of oxygen, glucose, lipid and hormones. It has been found that peroxisome affects the formation of the cell membrane and adipocyte as well as insulin sensitivity, through lipid metabolism and glucose metabolism and plays an important role in aging and tumorigenesis through action on oxidative stress (J Cutan Med Sirg 5 (3):231-43, 2001, J Cutan Med Sirg 5 (4):315-22, 2001).
  • PPARs peroxisome proliferator-activated receptos
  • PPAR- ⁇ peroxisome proliferator-activated receptos
  • the present inventors have exams general information on biology of these PPARs and effects and working mechanism of PPAR- ⁇ on skin, particularly relation with skin aging to find a ligand capable of inducing activation.
  • the composition for external use on skin according to the present invention it is possible to inhibit inflammation induced by natural aging and photo-aging, thereby preventing or recovering skin aging.
  • the composition for external use according to the present invention can inhibit expression of matrix metalloproteinase-1, an enzyme to decompose the dermis by inflammation inhibiting mechanism through activation of PPAR- ⁇ .
  • composition for external use according to the present invention is not particularly limited in its formulation but may be cosmetic compositions including, for example, skin softener, skin lotion, massage cream, nourishing cream, pack, gel or skin adhesive type cosmetic formulations, or transdermal formulations such as lotion, ointment, gel, cream, patch or spray.
  • cosmetic compositions including, for example, skin softener, skin lotion, massage cream, nourishing cream, pack, gel or skin adhesive type cosmetic formulations, or transdermal formulations such as lotion, ointment, gel, cream, patch or spray.
  • composition for external use in various formulation types may comprise the above-described essential components in combination with other components which may be selected by the workers in the art without any difficulty according to the formulation type or the purpose of use.
  • Human keratinocytes were cultured in a 24-well plate type incubator at a concentration of 10 4 . After 24 hours, the plate was irradiated by UV-B at 30 mJ/cm 2 . The media were exchanged with new medium containing 10 ppm of each test substance. After 2 days of cultivation, each supernatant was harvested and subjected to the zymography using gelatine gel to obtain produced MMP-2 and MMP-9, quantities of which were then measured by a densitometer. The data were calculated as comparative values, referred to 100 of UV control and the result is shown in Table 1.
  • the active ingredient used as an active ingredient in the present invention myricetin, epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), epicatechin gallate (ECG), catechin gallate (CG), green tea catechin extract and green tea extract reduced biosynthesis of MMP-2 and MMP-9, enzymes to decompose type IV collagen and type VII collagen of dermal matrix, thereby preventing decomposition of the dermis-epidermis junction.
  • EGCG epigallocatechin gallate
  • GCG gallocatechin gallate
  • ECG epicatechin gallate
  • CG catechin gallate
  • green tea catechin extract and green tea extract reduced biosynthesis of MMP-2 and MMP-9, enzymes to decompose type IV collagen and type VII collagen of dermal matrix, thereby preventing decomposition of the dermis-epidermis junction.
  • Human keratinocytes were cultured in a 24-well plate type incubator at a concentration of 5 ⁇ 10 4 .
  • the media were exchanged with new medium containing 10 ppm of each test substance. After 24 hours of cultivation, each supernatant was harvested and subjected to the Dot Blot method to measure the amount of produced type IV collagen.
  • the data were calculated as comparative values, referred to 100 of UV control and the result is shown in Table 2.
  • the active ingredient used as an active ingredient in the present invention myricetin, epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), epicatechin gallate (ECG), catechin gallate (CG), green tea catechin extract and green tea extract increased biosynthesis of type IV collagen.
  • Human fibroblasts were cultured in a 24-well plate type incubator at a concentration of 10 4 .
  • the media were exchanged with new medium containing 10 ppm of each test substance.
  • each supernatant was harvested and subjected to the Dot Blot method to measure the amount of produced type VII collagen.
  • the data were calculated as comparative values, referred to 100 of UV control and the result is shown in Table 3.
  • the active ingredient used as an active ingredient in the present invention myricetin, epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), epicatechin gallate (ECG), catechin gallate (CG), green tea catechin extract and green tea extract increased biosynthesis of type VII collagen.
  • Human keratinocytes were cultured in a 24-well plate type incubator at a concentration of 5 ⁇ 10 4 .
  • the media were exchanged with new medium containing 10 ppm of each test substance. After 24 hours of cultivation, each supernatant was harvested and subjected to the Western Blot method to measure the amount of produced laminin 10/11.
  • the data were calculated as comparative values, referred to 100 of UV control and the result is shown in Table 4.
  • Examples 1 to 9 and Comparative example 1 were prepared in a nourishing cream formulation as shown in Table 5 and applied on the back of a nude mouse 5 times per week for 2 weeks. Then, the formulations were applied 5 times on the back while the back was irradiated with UV 3 times per week for 12 weeks. Through biopsy, the change at the dermis-epidermis junction was examined using an electron microscope.
  • myricetin when myricetin is used in combination with epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), epicatechin gallate (ECG), catechin gallate (CG), green tea catechin extract and green tea extract, the effect was better, as compared to the case when myricetin is used alone. Also, it was more preferable to use myricetin at a low concentration in combination with catechin, as compared to the case when it is used alone at a high concentration.
  • EGCG epigallocatechin gallate
  • GCG gallocatechin gallate
  • ECG epicatechin gallate
  • green tea catechin extract green tea extract
  • Human fibroblasts were cultured in a 48-well plate type incubator at a concentration of 10 4 .
  • the media were exchanged with new medium (theanine: 1, 10, 100 um) containing each test substance of Table 7 at a concentration of 0.001 ⁇ M, 0.01 ⁇ M, 0.1 ⁇ M, 0.5 ⁇ M and 2 ⁇ M.
  • new medium theanine: 1, 10, 100 um
  • each supernatant was harvested and subjected to ELISA (Takara MK101) to measure the amount of produced pro-collagen.
  • the data were calculated as comparative values, referred to 100 of untreated control and the result is shown in Table 7.
  • compositions for external use comprising catechin and theanine in a predetermined mixing ratio according to Examples 10 to 13 showed excellent effect of improving skin wrinkle.
  • Nourishing creams prepared according to the compositions of Table 9 were examined for their effect to improve skin elastic.
  • 100 healthy women over 30 years old were divided into 10 groups.
  • Each group applied one of the nourishing cream of Comparative examples 2 to 7 and Examples 10 to 13 on the face twice per day at a temperature of 24-26° C. and a humidity of 75% for cream for 12 weeks and was examined for skin elasticity using Cutometer SEM 575, (C+K Electronic Co., Germany).
  • Cutometer SEM 575 (C+K Electronic Co., Germany).
  • the result is shown in Table 11.
  • the data of Table 11 are described as R8 (R8 (left)-R8 (right)) of the Cutometer SEM 575, in which RS means skin viscoelasticity.
  • Monkey kidney epithelial cell line CV-1 (ATCC CCL 70) was subcultured in a DMEM medium containing 10% fetal bovine serum treated with charcol/dextran, which was a phenol red-free medium to remove the effect by estrogen of phenol red.
  • Three different plasmids each comprising a universal promoter capable of being expressed in a general culturing conditions and having PPAR- ⁇ gene in the down stream, a universal promoter having PPRE (PPARs Response Element), which is activated by bonding to PPAR- ⁇ of ligand bonding type, and firefly luciferase gene, which functions as a reporter and a universal promoter with Renilla luciferase gene attached as a reference were used.
  • PPRE PPARs Response Element
  • CV-1 cells were distributed in a 24-well plate type incubator at a concentration of 5 ⁇ 10 4 . After 24 hours cultivation, the 3 different plasmids were transient transfected. After 24 hours cultivation, the plate was washed with 1 ⁇ PBS (Phosphate Buffered Saline) and treated with ligand candidates at various concentrations. After 24 hours cultivation, the plate was washed with 1 ⁇ PBS and the cells were lyzed with 1 ⁇ PLB (Passive Lysis Buffer) and measured for luciferase activity using Dual-Luciferase R Reporter Assay System kit.
  • 1 ⁇ PBS Phosphate Buffered Saline
  • ligand candidates at various concentrations.
  • 1 ⁇ PLB Passive Lysis Buffer
  • the positive control was Wy-14,643 which was known to be most powerful PPAR- ⁇ ligand and the negative control was ethanol which was used to dissolve the samples and non-treated group.
  • the result is shown in Table 13, with the data as comparative values referred to as 1.0 of the negative control and the non-treated group.
  • Human keratinocytes were cultured in a 12-well plate type incubator at a concentration of 10 4 .
  • the plate was irradiated by UV-B at 30 mJ/cm 2 .
  • the media were exchanged with new medium containing 10 ⁇ M of each test substance (10 ppm of extract).
  • the cells were harvested and subjected to ELISA (Pharmingen 555212) to determine the amount of produced tumor necrosis factor ⁇ (TNF- ⁇ ).
  • ELISA Pharmingen 555212
  • Wy-14,643 was used as comparative values, referred to 100 of UV control.
  • Human fibroblasts isolated from the skin of new born baby were cultured in a 48-well plate type incubator at a concentration of 10 4 . after 24 hours, the plate was irradiated by UV-A at 15 J/cm 2 and antibody against tumor necrosis factor alpha was added thereto in a concentration of 1 ug/ml. At the second day of cultivation, the supernatants were harvested and subjected to ELISA (AP biotech RPN2610) to determine the amount of produced type I collagenase. The result is shown in Table 15 as comparative values, referred to 100 of control which was not treated.
  • composition for external use on skin according to the present invention is not limited thereto.
  • composition for external use on skin comprises at least one of catechins and flavonols which are components of green tea as an active ingredient to reduce biosynthesis of gelatinase (MMP-2, MMP-9) and increase biosynthesis of type IV collagen, type VII collagen and laminin 10/11 thereby inhibiting decomposition and promoting generation of the dermis-epidermis junction and protecting the dermis-epidermis junction.
  • catechins and flavonols which are components of green tea as an active ingredient to reduce biosynthesis of gelatinase (MMP-2, MMP-9) and increase biosynthesis of type IV collagen, type VII collagen and laminin 10/11 thereby inhibiting decomposition and promoting generation of the dermis-epidermis junction and protecting the dermis-epidermis junction.

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US12/064,887 2005-09-08 2006-09-08 Composition Of Skin External Application For Anti-Aging Abandoned US20090012155A1 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
KR1020050083665A KR101219293B1 (ko) 2005-09-08 2005-09-08 최적 농도의 카테킨과 데아닌을 함유하는 피부 외용제조성물
KR10-2005-0083667 2005-09-08
KR1020050083667A KR101219296B1 (ko) 2005-09-08 2005-09-08 표피-진피 경계부 보호용 피부 외용제 조성물
KR10-2005-0083665 2005-09-08
KR10-2006-0021797 2006-03-08
KR1020060021797A KR20070091964A (ko) 2006-03-08 2006-03-08 퍼옥시좀 증식체 활성화 수용체 알파 활성화용 피부 외용제조성물
PCT/KR2006/003571 WO2007029982A1 (en) 2005-09-08 2006-09-08 Composition of skin external application for anti-aging

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FR2997855A1 (fr) * 2012-11-15 2014-05-16 Rocher Yves Biolog Vegetale Utilisation d'un extrait de saba senegalensis dans une composition cosmetique apaisante et/ou uniformisant la couleur de la peau
US9132294B2 (en) 2010-06-30 2015-09-15 Avon Products, Inc. Compositions and methods for stimulation MAGP-1 to improve the appearance of skin
US9409860B2 (en) 2010-06-30 2016-08-09 Avon Products Inc. Cosmetic use of N-substituted sulfonyloxybenzylamines and related compounds
US20180021411A1 (en) * 2016-07-20 2018-01-25 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Composition and Method for Improving Sleep Duration and Quality
US10980735B2 (en) 2016-09-30 2021-04-20 Amorepacific Corporation Externally-applied dermal preparation composition containing extract of green tea cultivated under extreme shading

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KR101404398B1 (ko) * 2007-06-20 2014-06-09 (주)뉴트리 주름개선 화장료 조성물
IT1393841B1 (it) * 2009-04-30 2012-05-11 Giuliani Spa Composizione farmaceutica o dermatologica o nutrizionale o cosmetica per combattere l'azione di immunosoppressione provocata sulla pelle da agenti aggressivi
FR2956977A1 (fr) * 2010-03-03 2011-09-09 Emulscience Composition cosmetique anti-age, utilisation et procede d'application correspondant
US8455518B2 (en) * 2010-12-28 2013-06-04 Avon Products, Inc. Method of treating skin with microRNA modulators
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US20160175217A1 (en) 2016-06-23

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