EP1337235A1 - Procede cosmetique de traitement de la peau - Google Patents

Procede cosmetique de traitement de la peau

Info

Publication number
EP1337235A1
EP1337235A1 EP01997293A EP01997293A EP1337235A1 EP 1337235 A1 EP1337235 A1 EP 1337235A1 EP 01997293 A EP01997293 A EP 01997293A EP 01997293 A EP01997293 A EP 01997293A EP 1337235 A1 EP1337235 A1 EP 1337235A1
Authority
EP
European Patent Office
Prior art keywords
skin
pinolenic acid
treating
boosting
improving
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP01997293A
Other languages
German (de)
English (en)
Inventor
Sarah Louise Unilever R & D Colworth BLACHFORD
Rebecca Susan Unilever R & D Colworth GINGER
Preyesh Unilever R & D Colworth PARMAR
Julia Sarah Unilever R & D Colworth ROGERS
Paula Rachel Unilever R & D Colworth YATES
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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 Unilever PLC, Unilever NV filed Critical Unilever PLC
Publication of EP1337235A1 publication Critical patent/EP1337235A1/fr
Withdrawn legal-status Critical Current

Links

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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61Q19/004—Aftersun 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
    • A61Q19/005—Preparations for sensitive skin
    • 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
    • A61Q19/007—Preparations for dry skin
    • 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

Definitions

  • This invention relates to a cosmetic method of improving the condition and appearance of skin and to the use of pinolenic acid in the preparation of topical compositions for improving the condition and appearance of skin.
  • fatty acids including pinolenic acid
  • pine nut oil which contains pinolenic acid
  • pine nut oil can have an anti- inflammatory effect, where it is used to coat nail files to inhibit any infections caused on use of the files.
  • pinolenic acid which are useful in cosmetic compositions for topical application to skin to provide previously undisclosed skin care benefits.
  • a topical composition for application to the human skin comprising an effective amount of pinolenic acid.
  • a cosmetic method of providing at least one skin care benefit selected from: treating/preventing wrinkling, sagging, aged and/or photodamaged skin; boosting collagen deposition in skin, boosting decorin production in skin, enhancing tissue repair; improving skin condition and resilience through enhanced barrier formation; treating dry and flaky skin; reduced hyperproliferation; soothing irritated, red and/or sensitive skin; and improving skin texture, smoothness and/or firmness; the method comprising applying to the skin a topical composition comprising pinolenic acid and/or derivatives thereof.
  • the present invention also encompasses the use of pinolenic acid and/or derivatives thereof in a topical composition for providing at least one skin care benefit selected from treating/preventing wrinkling, sagging, aged and/or photodamaged skin; boosting collagen deposition in skin, boosting decorin production in skin, enhancing tissue repair; improving skin condition and resilience through enhanced barrier formation; treating dry and flaky skin; reduced hyperproliferation; soothing irritated, red and/or sensitive skin; improving skin texture, smoothness and/or firmness .
  • the inventive methods and use of pinolenic acid thus provide anti-aging benefits which result in the promotion of smooth and supple skin with improved elasticity and a reduced or delayed appearance of wrinkles and aged skin, with improved skin colour.
  • a general improvement in the appearance, texture and condition, in particular with respect to the radiance, clarity, and general youthful appearance of skin may be achieved.
  • the inventive methods and uses are also beneficial for soothing and calming sensitive and/or irritated skin.
  • the inventive methods advantageously provide a wide range of skin care benefits.
  • treating includes within its scope reducing, delaying and/or preventing the above mentioned skin conditions such as wrinkled, aged, photodamaged, and/or irritated skin and generally enhancing the quality of skin and improving its appearance and texture by preventing or reducing wrinkling and increasing flexibility, firmness, smoothness, suppleness and elasticity of the skin.
  • the cosmetic methods and the uses of pinolenic acid and/or derivatives according to the invention may be useful for treating skin which is already in a wrinkled, aged, photodamaged, dry and irritated condition or for treating youthful skin to prevent or reduce those aforementioned deteriorative changes due to the normal aging/photoaging process.
  • Pinoleic acid is an unsaturated long chain (C18) fatty acid, having three double bonds at the 5,9, and 12 positions. It may be found in e.g. pine nut oil at levels of around 25%.
  • the invention also includes derivatives of the free acid which thus comprise pinolenic acid moieties.
  • Preferable derivatives include those derived from substitution of the carboxyl group of the acid, such as esters (eg retinyl esters, triglyceride esters, monoglyceride esters, diglyceride esters, phosphoesters) , amides (eg ceramide derivatives) , salts (eg alkali metal and alkali earth metal salts, ammonium salts) ; and/or those derived from substitution of the C18 carbon chain, such as alpha hydroxy and/or beta hydroxy derivatives.
  • esters eg retinyl esters, triglyceride esters, monoglyceride esters, diglyceride esters, phosphoesters
  • amides eg ceramide derivatives
  • salts eg alkali metal and alkali earth metal salts, ammonium salts
  • substitution of the C18 carbon chain such as al
  • triglyceride ester derivatives all positional isomers of pinolenic acid substituents on the glycerol backbone are included.
  • the triglycerides must contain at least one pinolenic acid moiety.
  • the 1 and 2 positions may be esterified with pinolenic acid and by another lipid at position 3 or as an alternative, the glycerol backbone could be esterified by PA at the 1 and 3 positions with another lipid at position 2. Oils that may be rich in pinolenic acid triglyceride would thus also suitable for use in the present invention.
  • pinolenic refers to pinolenic fatty acyl portion (s) of a pinolenic derivative.
  • the active, pinolenic acid, to be employed in accordance with the present invention is present in the topical composition in an effective amount. Normally the total amount of the active is present in an amount between 0.0001% and 50% by weight of the composition. More preferably the amount is from 0.01% to 10% and most preferably from 0.1% to 5% in order to maximise benefits at a minimum cost.
  • composition used according to the invention also comprises a dermatologically/cosmetically acceptable vehicle to act as a dilutant, dispersant or carrier for the active pinolenic acid or its derivative.
  • vehicle may comprise materials commonly employed in skin care products such as water, liquid or solid emollients, silicone oils, emulsifiers, solvents, humectants, thickeners, powders, propellants and the like.
  • the vehicle will usually form from 5% to 99.9%, preferably from 25% to 80% by weight of the composition, and can, in the absence of other cosmetic adjuncts, form the balance of the composition.
  • the vehicle may also further include adjuncts such as perfumes, opacifiers, preservatives, colourants and buffers.
  • the usual manner for preparing skin care products may be employed.
  • the active components are generally incorporated in a dermatologically acceptable carrier in conventional manner.
  • the active components can suitably first be dissolved or dispersed in a portion of the water or another solvent or liquid to be incorporated in the composition.
  • the preferred compositions are oil-in-water or water-in-oil emulsions.
  • the composition may be in the form of conventional skin-care products such as a cream, gel or lotion or the like.
  • the composition can also be in the form of a so-called "wash- off” product e.g. a bath or shower gel, possibly containing a delivery system for the actives to promote adherence to the skin during rinsing.
  • wash- off product e.g. a bath or shower gel, possibly containing a delivery system for the actives to promote adherence to the skin during rinsing.
  • the product is a "leave-on” product; a product to be applied to the skin without a deliberate rinsing step soon after its application to the skin.
  • composition may packaged in any suitable manner such as in a jar, a bottle, tube, roll-ball, or the like, in the conventional manner.
  • the method of the present invention may be carried out one or more times daily to the skin which requires treatment.
  • the improvement in skin appearance will usually become visible after 3 to 6 months, depending on skin condition, the concentration of the active components used in the inventive method, the amount of composition used and the frequency with which it is applied.
  • a small quantity of the composition for example from 0.1 to 5 ml is applied to the skin from a suitable container or applicator and spread over and/or rubbed into the skin using the hands or fingers or a suitable device.
  • a rinsing step may optionally follow depending on whether the composition is formulated as a "leave-on" or a "rinse-off" product.
  • Figures 1 and 2 show the effect of pinolenic acid on decorin and procollagen I upregulation
  • Figures 3 and 4 demonstrate the effect of pinolenic acid on stimulated PGE2 levels in fibroblasts and on PMA stimulated sICAM-1 levels in fibroblasts
  • - Figure 5 shows the effect of pinolenic acid on cornified envelope formation
  • Figure 6 shows the effect of pinolenic acid on keratinocyte differentiation.
  • Dot Blot Assay for Procollagen-I and Decorin Protein in Dermal Fibroblast Conditioned Medium Samples of conditioned medium from dermal fibroblasts treated with vehicle (as a control) or test reagents were supplemented with 20mM dithiothreitol (1:10 dilution of 200mM stock solution) and 0.1% sodium dodecylsulphate (1:100 dilution of 10% stock solution) , mixed well and then incubated at 75°C for 2 minutes.
  • a standard for the assay was generated by serial dilution of neat fibroblast conditioned medium from fibroblasts seeded at 10000 cells/cm 2 in a 175cm 2 flask and maintained in serum free DMEM as described above.
  • the membranes were subsequently washed with TBS/ 0.05% Tween 20 (3 5 minutes) and then incubated with 1:1000 dilution of 125 I-conjugated anti-rat or anti-rabbit F(ab')2 fragments (Amersham) as required for 1 hour at room temperature.
  • Table 1 indicates the effects of pinolenic acid on procollagen-I and decorin synthesis in human dermal fibroblasts, and the amounts in which it was applied. In order to normalise the results the effects of the test substance was determined relative to a vehicle treated control value of 100 arbitrary units. Figures 1 and 2 show the results for more data points graphically.
  • the level of decorin in skin is associated with improved condition and appearance of skin. Increasing the level of decorin in skin is important for controlled and correct deposition of collagen in skin which is associated with many skin benefits such as wrinkle effacement and dermal repair of photodamaged skin.
  • This example measures the effect of pinolenic acid on reducing the inflammatory response of dermal fibroblasts.
  • Intracellular adhesion molecules IAM
  • PEG2 production by human skin fibroblasts can be induced by the inflammatory stimulus PMA (phorbal myristate acetate) .
  • PMA represents an external stressor which induces oxidative stress and inflammatory responses in cells. This model , is used to model inflammation in vivo.
  • Prostaglandin E2 (PGE 2 ) assay Volumes of 50 ⁇ l culture medium were taken for PGE 2 assay after gently shaking the culture plate. PGE 2 levels in the medium were determined with a Biotrak PGE 2 immunoassay kit (Amersham, UK) . The assay is based on the competition between unlabelled PGE 2 in the sample and a fixed quantity of horseradish peroxidase labeled PGE 2 for a limited amount of fixed PGE 2 specific antibody. Concentrations of unlabelled sample PGE 2 are determined according to a standard curve which was obtained at the same time.
  • ICAM-1 assay Media were discarded and cells washed with Dulbecco PBS.
  • DMEM Dubleccos Modified Eagles Medium
  • the cells were grown for 3 days prior to treatment.
  • the treatment vehicle was DMSO.
  • the cells were harvested and washed three times with lOO ⁇ l phosphate buffered saline (PBS) .
  • the cells were then extracted in 1% Triton X100, 50mM Tris pH 8.0, 0.02mM Leupeptin, 0.02mM Pepstatin. 60 ⁇ l/well of extract was then assayed for DNA concentration (ng/well) , Pico Green DNA assay, Molecular Probes.
  • the cells were then washed in 200 ⁇ l PBS, and then lOO ⁇ l of 2% SDS, 20mM DTT was added to each well.
  • the plates were then sealed with a Titertek plate sealer (ICN) and incubated at 60°C over night in an air tight damp environment (i.e. a sealed sandwich box lined with damp paper) .
  • the extract was then filtered through a PVDF transfer membrane (Bio-rad) under gravity using Dot-Blot apparatus (Bio-rad) .
  • the membrane is then washed in distilled water prior to silver staining (Bio-rad Silver Stain kit) .
  • the stained dot blot membrane is then analysed using Phoretix array software (Phoretix International) .
  • the formulation below describes an oil in water cream suitable for the methods and uses according to the present invention.
  • the percentages indicated are by weight of the composition.
  • the formulation below describes an emulsion cream according to the present invention.
  • compositions of examples 4 and 5 provide an effective cosmetic treatment to improve the appearance of wrinkled, aged, photo-damaged, and/or irritated skin, when applied to skin that has deteriorated through the aging or photoaging or when applied to youthful skin to help prevent or delay such deteriorative changes.
  • the compositions can be processed in conventional manner.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Emergency Medicine (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne un procédé cosmétique permettant de traiter la peau âgée, sensible, sèche, squameuse, ridée et/ou dégradée par la lumière grâce à l'application locale d'une composition contenant de l'acide fenchénique et/ou des dérivés de celui-ci. L'invention concerne également des compositions adaptées à de tels traitements cosmétiques.
EP01997293A 2000-11-21 2001-11-07 Procede cosmetique de traitement de la peau Withdrawn EP1337235A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0028355 2000-11-21
GBGB0028355.6A GB0028355D0 (en) 2000-11-21 2000-11-21 Cosmetic method of treating skin
PCT/EP2001/013039 WO2002041865A1 (fr) 2000-11-21 2001-11-07 Procede cosmetique de traitement de la peau

Publications (1)

Publication Number Publication Date
EP1337235A1 true EP1337235A1 (fr) 2003-08-27

Family

ID=9903574

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01997293A Withdrawn EP1337235A1 (fr) 2000-11-21 2001-11-07 Procede cosmetique de traitement de la peau

Country Status (10)

Country Link
EP (1) EP1337235A1 (fr)
JP (1) JP2004523488A (fr)
KR (1) KR20030062349A (fr)
CN (1) CN1486174A (fr)
AU (2) AU2069402A (fr)
CA (1) CA2428634A1 (fr)
GB (1) GB0028355D0 (fr)
MX (1) MXPA03004449A (fr)
WO (1) WO2002041865A1 (fr)
ZA (1) ZA200303776B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1506042A (zh) * 2002-12-11 2004-06-23 苏加璐 使用来自胎儿细胞和组织的化合物改善皮肤状况的方法和组合物
JP2004224742A (ja) * 2003-01-23 2004-08-12 Umeken:Kk 皮膚外用剤
JP2007063195A (ja) * 2005-08-31 2007-03-15 Katakura Chikkarin Co Ltd 美白剤およびこれを含有する皮膚外用剤
HU227970B1 (en) 2007-07-10 2012-07-30 Egis Gyogyszergyar Nyrt Pharmaceutical compositions containing silicones of high volatility
GB0814105D0 (en) * 2008-08-01 2008-09-10 Springdale Sustainable Develop Composition for accelerated production of collagen
US11154535B2 (en) 2012-07-31 2021-10-26 Egis Pharmaceuticals Plc Transdermal formulation containing COX inhibitors
US10045935B2 (en) 2012-07-31 2018-08-14 Egis Pharmaceuticals Plc Transdermal formulation containing COX inhibitors

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6163610A (ja) * 1984-09-05 1986-04-01 Nisshin Oil Mills Ltd:The 化粧料
FR2756465B1 (fr) * 1996-12-03 1999-02-19 D A Noste Additif alimentaire, composition cosmetique et medicament a base d'huile de graines de pin
GB9918023D0 (en) * 1999-07-30 1999-09-29 Unilever Plc Skin care composition
DK1088552T3 (da) * 1999-09-30 2006-05-29 Loders Croklaan Bv Sammensætninger, der indeholder pinolensyre, samt deres anvendelse som en sund bestanddel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0241865A1 *

Also Published As

Publication number Publication date
CN1486174A (zh) 2004-03-31
MXPA03004449A (es) 2003-08-19
KR20030062349A (ko) 2003-07-23
GB0028355D0 (en) 2001-01-03
WO2002041865A1 (fr) 2002-05-30
AU2002220694B2 (en) 2005-02-10
JP2004523488A (ja) 2004-08-05
ZA200303776B (en) 2004-05-17
AU2069402A (en) 2002-06-03
CA2428634A1 (fr) 2002-05-30

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Inventor name: YATES, PAULA, RACHEL,UNILEVER R & D COLWORTH

Inventor name: ROGERS, JULIA, SARAH,UNILEVER R & D COLWORTH

Inventor name: PARMAR, PREYESH,UNILEVER R & D COLWORTH

Inventor name: GINGER, REBECCA, SUSAN,UNILEVER R & D COLWORTH

Inventor name: BLACHFORD, SARAH, LOUISE,UNILEVER R & D COLWOR

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Owner name: UNILEVER N.V.

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