WO2002015869A1 - Compositions cosmetiques - Google Patents

Compositions cosmetiques Download PDF

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Publication number
WO2002015869A1
WO2002015869A1 PCT/EP2001/009652 EP0109652W WO0215869A1 WO 2002015869 A1 WO2002015869 A1 WO 2002015869A1 EP 0109652 W EP0109652 W EP 0109652W WO 0215869 A1 WO0215869 A1 WO 0215869A1
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WIPO (PCT)
Prior art keywords
thr
lys
cosmetic composition
composition according
neosynthesis
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PCT/EP2001/009652
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English (en)
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WO2002015869A9 (fr
Inventor
Sylvie Le Squer
Pascale Oger
Christelle Marcantuani
Carine Bobier-Rival
Alain Fructus
Anne-Marie Matta
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Beiersdorf Ag
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Priority to EP01969626A priority Critical patent/EP1408925A1/fr
Publication of WO2002015869A1 publication Critical patent/WO2002015869A1/fr
Publication of WO2002015869A9 publication Critical patent/WO2002015869A9/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/645—Proteins of vegetable origin; Derivatives or degradation 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • 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
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin

Definitions

  • the present invention relates to new cosmetic compositions containing at least one compound stimulating the neosynthesis of laminins, and/or ⁇ 2 ⁇ 1 integrin and/or collagen IV of the dermo-epidermal junction.
  • Human skin is composed of three superimposed tissues: the hypodermis (the deepest), the dermis and finally the epidermis (the outermost).
  • the epidermis In order to fulfil its function as the first line of protection against aggressive influences (mechanical, chemical, microbiological), the epidermis has a highly differentiated structure: from the basal layer, the cells known as keratinocytes undergo a metabolic process of keratinisation which causes them to be transformed as they migrate towards the upper layers, finally becoming extremely resistant and relatively impermeable corneocytes which, with the epidermal lipids secreted by the keratinocytes of the granular layer, form the stratum corneum, the outermost layer of the epidermis, in contact with the external environment.
  • keratinocytes undergo a metabolic process of keratinisation which causes them to be transformed as they migrate towards the upper layers, finally becoming extremely resistant and relatively impermeable corneocytes which, with the epidermal lipids secreted by the keratinocytes of the granular layer, form the stratum corneum, the outermost layer of the epidermis, in contact with the external environment.
  • the epidermis contains other types of cells having important functions and a great capacity for communication: melanocytes, Langerhans' cells, Merckel cells.
  • the dermis is a tissue composed of a fundamental substance interspersed with a few cells (fibroblasts) and very numerous fibres (collagens and elastin), which gives the dermis an amorphous and compact structure though capable of stretching under a mechanical stress and then reverting to its initial size when the stress is released.
  • the epidermis is a stratified type with a high density of contiguous, columnar cells.
  • the DEJ is thus capable of ensuring cohesion between these two tissues with relatively incompatible mechanical properties when the skin is mechanically deformed.
  • the DEJ takes the shape of highly pronounced waves.
  • the DEJ has a very important role from a metabolic and mechanical angle for the good health of the skin.
  • the important role of the DEJ is also attested by the possibility of metabolic diseases when one of the components of the DEJ is absent or of poor quality.
  • the case of bullous pemphigoid may be mentioned, in which the absence of an important component (laminin-5) leads to the formation of blisters: the epidermis becomes detached from the dermis and forms blisters which develop into sores which are difficult to heal.
  • the structure of the DEJ is becoming increasingly better known: four layers can be distinguished, each of which has specific constituents and a very precise role (Allen J., Br.J.Dermatol. 1997 Dec; 137(6): 907-15), (M.Aumailley, Kidney Internal, Vol 47, Suppl.49 (1995), pp S-4-S-7).
  • a new trend involves stimulating the synthesis of the important components of the DEJ.
  • ursolic acid and oleanolic acid which are not described in the literature for this type of properties, are in fact capable of stimulating the neosynthesis of collagen IV and that, moreover, the combination with a specific palmitoyl pentapeptide -Lys-Thr- Thr-Lys-Ser for this activity, increased their stimulating capacity in an unexpected synergistic manner.
  • this palmitoyl pentapeptide -Lys-Thr-Thr-Lys-Ser is capable of stimulating the synthesis of 2 ⁇ 1 integrin and laminin.
  • a peptide extract of white lupin known for its anti-elastase and anti-collagenase (anti- metalloproteinase) properties is also capable of stimulating significantly the synthesis of collagen IV.
  • the present application provides a cosmetic composition containing at least one compound stimulating the neosynthesis of at least one and preferably two, particularly three important components of the dermo- epidermal junction and more particularly laminins, and/or ⁇ 2 ⁇ 1 integrin and/or collagen IV.
  • Examples of compounds which stimulate the neosynthesis of important components of the dermo-epidermal junction include preferably ursolic acid, oleanolic acid, palmitoyl pentapeptide in which the pentapeptide has the formula: -Lys-Thr-Thr-Lys-Ser and peptide extracts of white lupin.
  • Ursolic acid is a pentacyclic triterpene: 3 ⁇ -hydroxyurs-12-en-28-oic acid. It is found in a large number of plants, particularly rosemary. It is generally associated in these plants, and in the commercially available extracts, with its isomer oleanolic acid (3-hydroxyolean-12-en-oic acid).
  • the mixtures of ursolic acid/oleanolic acid are generally in the form of a sodium salt, the respective proportions of the two ranging from 80 - 20 to 70 - 30 depending on the plant from which said mixtures are extracted, the purity of the mixture of the two ranging from 60% to 98%. Consequently, the compositions according to the invention may contain either or both of the acids.
  • the peptide extract of white lupin (variety L. albus) contains pure peptides with a low molecular weight obtained from seeds from which the lipids have been removed according to a bioengineering process which removes polysaccharides.
  • This process which comprises the unit steps of solubilisation of the vegetable proteins, enzymatic hydrolysis and ultrafiltration, makes it possible to obtain peptides containing 5 to 6 units of amino acids, on average.
  • This type of product is sold, in particular, by the company Expanchimie under the commercial name of "Actimp1.9.3®" and it is known for its inhibiting properties with respect to matrix metalloproteinases (MMP).
  • MMP matrix metalloproteinases
  • Palmitoyl pentapeptide-Lys-Thr-Thr-Lys-Ser is a mimetic of a fragment of Type I procollagen. It is obtained by peptide synthesis and then bound to a palmitic acid chain in order to improve its lipophilic properties and hence its penetration of the skin.
  • Palmitoyl pentapeptide -Lys-Thr-Thr-Lys-Ser is sold by the company Sederma under the commercial name Matrixyl®, contained in a gel in a quantity of 100 ppm, the gel containing about 25% of water, about 20% of butylene glycol, about 1% of carbomer and about 0.5% of polysorbate 20.
  • the commercial product is in the form of a whitish opalescent gel with a pH of 4 to 6, a density at 20 °C of 1.140 to 1.160 and with a refractive index at 25 °C from 1.425 to 1.445.
  • composition as mentioned above contains ursolic acid and/or oleanolic acid and also palmitoyl pentapeptide in which the pentapeptide has the formula: -Lys-Thr-Thr-Lys-Ser.
  • ursolic acid may represent, for example, from 0.001% to 10%, particularly 0.01% to 5%, preferably from 0.05% to 2% and more particularly from 0.07% to 1% of the finished composition.
  • Oleanolic acid may represent, for example, from 0.00025% to 2.5%, particularly 0.0025% to 1.3%, preferably from 0.0125% to 0.5% and more particularly from 0.0175% to 0.25% of the finished composition.
  • Palmitoyl pentapeptide may represent, for example, from 0.1 ppm to 30 ppm, particularly 0.5 ppm to 20 ppm, preferably from 1 ppm to 15 ppm and more particularly from 2 ppm to 10 ppm of the finished composition.
  • the peptide extract of white lupin may represent, for example, from 0.2% to 10%, particularly 0.5% to 5%, preferably from 0.7% to 4% and more particularly from 1 % to 3% of the finished composition.
  • compositions containing from 0.01% to 5% of ursolic acid/oleanolic acid combined with 0.1 ppm to 30 ppm of palmitoyl pentapeptide-Lys-Thr-Thr-Lys- Ser, and those containing from 0.2% to 2% of ursolic acid/oleanolic acid combined with 1 ppm to 10 ppm of palmitoyl pentapeptide-Lys-Thr-Thr-Lys-Ser may be mentioned more particularly.
  • Particularly preferred combinations of active principles are combinations in the same composition of
  • ursolic acid and/or oleanolic acid palmitoyl pentapeptide-Lys-Thr-Thr- Lys-Ser and peptide extract of white lupin.
  • compositions according to the invention are intended substantially for application to the skin.
  • they will take the form of hydro-alcoholic gels or hydro-glycolic gels, water/oil or oil/water emulsions with or without emulsifiers, with or without lamellar phases, water/oil/water or oil/water/oil triple emulsions, microemulsions, mini-emulsions.
  • compositions forming the subject matter of the present invention have very attractive properties. In particular, they have remarkable properties for combating the effects of skin ageing.
  • compositions according to the present invention are used, for example, in the fight both to cure and prevent the effects of skin ageing.
  • compositions according to the present invention are prepared by conventional methods.
  • the active compound(s) may be incorporated in excipients normally used in cosmetic compositions intended for topical application, such as glycerol, sorbitol, stearates, PEG, silicones, cocoa butter, aqueous or non-aqueous vehicles, oil substances of animal or vegetable origin, paraffin derivatives, glycols, alcohols or oil acids, various moisturisers, dispersing agents or emulsifiers, preservatives, perfumes.
  • the present invention also provides a process for the preparation of a composition described above, characterised in that the active principle(s) is (are) mixed, by inherently known methods, with acceptable excipients, particularly cosmetically acceptable excipients.
  • active principle(s) is (are) mixed, by inherently known methods, with acceptable excipients, particularly cosmetically acceptable excipients.
  • an aqueous phase and an oil phase will be prepared separately, then mixed at elevated temperature with stirring.
  • the present application also provides the use of a compound which stimulates the neosynthesis of at least one and preferably two, particularly three important components of the dermo-epidermal junction and more particularly laminins, and/or ⁇ 2 ⁇ 1 integrin and/or collagen IV for the treatment of skin and particularly for curing and preventing the effects of skin ageing, and a process for curing and preventing the effects of skin ageing in which an effective amount of a composition as described above is applied topically.
  • An anti-wrinkle cream for normal skins and combination skins was prepared as follows:
  • the following oil phase was prepared: Cetyl alcohol and glyceryl stearate and PEG-7S stearate and ceteth-20 and steareth-20 4 g
  • This mixture was heated to 70 °C and homogenised thoroughly.
  • aqueous phase Purified water, quantum sufficit (q.s.) 100 g Tetrasodium EDTA 0.05 g
  • the homogeneous oil phase heated to 70 °C was poured slowly over the aqueous phase heated to the same temperature, with fairly vigorous stirring. Stirring was maintained for 10 minutes after the end of the introduction of the oil phase.
  • the emulsion was then cooled with moderate stirring.
  • Polyethylene glycol 400 (10/90) 2 g
  • the emulsion was cooled to 30 °C with slow stirring.
  • the following oil phase was prepared: Cetyl alcohol and glyceryl stearate and PEG-7S stearate and ceteth-20 and steareth-20 4 g Jojoba oil 4 g
  • Silicone oil (phenyl trimethicone) 5 g
  • This mixture was heated to 70 °C and homogenised thoroughly.
  • the homogeneous oil phase heated to 70 °C was poured slowly over the aqueous phase heated to the same temperature, with fairly vigorous stirring. Stirring was maintained for 10 minutes after the end of the introduction of the oil phase.
  • the emulsion was then cooled with moderate stirring.
  • Polyethylene glycol 400 (10/90) 2 g
  • the emulsion was cooled to 30 °C with slow stirring.
  • the oil phase was composed of:
  • This oil phase was heated to 70 °C and homogenised thoroughly.
  • the oil phase homogenised and heated to 70 °C, was poured slowly over the aqueous phase heated to the same temperature with fairly vigorous stirring. Stirring was maintained for 10 minutes after the end of the introduction of the oil phase.
  • the emulsion was then cooled with moderate stirring.
  • the emulsion was cooled to 30 °C with slow stirring.
  • the oil phase was composed of:
  • This oil phase was heated to 60 °C and homogenised thoroughly.
  • the oil phase homogenised and heated to 60 °C, was poured slowly over the aqueous phase heated to the same temperature with fairly vigorous stirring. Stirring was maintained for 10 minutes after the end of the introduction of the oil phase.
  • the emulsion was then cooled with moderate stirring.
  • the emulsion was cooled to 30 °C with slow stirring.
  • a white, very oily cream was obtained, suitable for application at night.
  • Example 5 Oil/water cream with lamellar phases The following oil/water cream with lamellar phases was prepared:
  • the oil phase was composed of:
  • This oil phase was heated to 80 °C and homogenised thoroughly.
  • the oil phase homogenised and heated to 80 °C, was poured slowly over the aqueous phase heated to the same temperature with fairly vigorous stirring. Stirring was maintained for 10 minutes after the end of the introduction of the oil phase.
  • the emulsion was then cooled with moderate stirring.
  • the emulsion was cooled to 30 °C with slow stirring.
  • a white, very oily cream with lamellar phases was obtained which may facilitate the penetration of the active principles and prolong hydration thereof.
  • Experiment 1 Effect of the products tested on the production of collagen IV, laminin and ⁇ 2 ⁇ 1 integrin by human fibroblasts (immunoenzyme method of the immunoblot type).
  • -P1 1 % or 2% gel of palmitoyl pentapeptide-Lys-Thr-Thr-Lys-Ser -P2: 1 % or 2% malt extract -P3: 2% or 3% yeast extract
  • Normal human dermal fibroblasts (NHDF, R8PF2, used in the 8th passage) were seeded onto an MEM/M199 (Gibco) medium without serum. They were cultured to confluence at 37 °C and under 5% of CO 2 . They were then treated in triplicate respectively with the 12 preparations or mixtures, continuously for 72 hours.
  • the cell lawns were observed at the end of the treatments and . the samples were frozen at -80 °C. At the end of the treatments, sodium dodecyl sulfate (SDS) (1 % final) was added to the culture media, and the cell and extracellular proteins were extracted for 30 min with stirring; extraction was completed with gentle sonication of all the samples.
  • SDS sodium dodecyl sulfate
  • Immunoblotting was then carried out.
  • the protein fractions were transferred onto nitrocellulose (Hybond, ECL, Amersham) using a MilliBlot module (Millipore, transfer under vacuum). Two nitrocelluloses were used for each antibody used (8 membranes in total, 45 spots per membrane).
  • control wells without cell
  • culture medium containing the test products in the greatest concentrations were prepared (in order to detect whether the test product was recognised by either of the antibodies).
  • controls without primary antibodies were carried out (untreated cells).
  • the membranes were saturated by incubation for 16 hours (4 °C) in a phosphate buffer PBS/0.05% Tween 20/5% skimmed milk (PBSTL).
  • PBSTL phosphate buffer PBS/0.05% Tween 20/5% skimmed milk
  • the strips of control wells without primary antibody were cut out for separate treatment (incubation with the peroxidase conjugate only).
  • the specific antigen sites were labelled with primary antibodies (see table below) in the dilutions indicated (in PBSTL, see table below), for 1 hour at 37 °C.
  • the primary antibodies fixed were revealed by an anti-immunoglobuiin-peroxidase conjugate.
  • the evaluation parameter was MTT hydrolysis.
  • the raw data were transferred and processed using PRISM® software (Graph Pad Software).
  • the inter-group comparisons were carried out by analysis of variance (ANOVA) using the DUNNETT multiple comparison test.
  • the immunofluorescence controls were carried out on untreated cell lawns (references) fixed with methanol at -20 °C and dried. The principle, the reagents and the times were the same as for immunoblotting.
  • the secondary antibodies were fluorescein-N-isothiocyanate conjugates (FITC) (see table below) instead of peroxidase conjugates.
  • FITC fluorescein-N-isothiocyanate conjugates
  • the cell nuclei were stained by incubation in a solution of 1 ⁇ g/ml Hoechst dye (bis-benzimide, Sigma B1155).
  • the sections were observed under an epifluorescence microscope (NIKON, Diaphot 300).
  • the images were captured using a COHU camera controlled by Visiolab 200 software.
  • Actin was used as a reference marker to show that the cell model used was valid. A relative fluctuation in the results was observed with the anti-actin monoclonal antibody. As a general rule, none of the products or mixtures showed any appreciable stimulation of actin expression (no significantly increased cell proliferation; the experiment was carried out to confluence). Moreover, the products and mixtures did not significantly reduce the production of actin, although malt extract (2% and 1%) and ursolic acid/oleanolic acid, sodium salt (0.0075%) apparently had a tendency to reduce the signal measured.
  • yeast extract the product alone (without cell) produced a visible signal suggesting that a component of the product was recognised by the anti-actin monoclonal antibody.
  • the mixtures showed variable activities.
  • the gel of palmitoyl pentapeptide-Lys-Thr-Thr-Lys-Ser strongly stimulated the production of collagen IV; moreover, all the mixtures containing the gel of palmitoyl pentapeptide-Lys-Thr-Thr-Lys-Ser stimulated the production of collagen IV by a factor of more than 2.
  • yeast extract is not recognised by anti-collagen IV (no significant signal in the control of yeast extract without cells).
  • Ursolic acid/oleanolic acid, sodium salt showed a significant intensification of the signal (factor of 1.5); less stimulation (not significant) was observed at 0.0037%.
  • the results obtained with the isolated products are shown in the table below (densitometric analysis, results in % relative to the untreated reference).
  • the gel of palmitoyl pentapeptide-Lys-Thr-Thr-Lys-Ser (P1) stimulated the production of the three selected markers of the dermo-epidermal junction.
  • the activity of the product was particularly pronounced on collagen IV.
  • Yeast extract produced artefacts with the anti-actin antibody and above all with the anti-integrin antibody.
  • the product alone or in mixture did not show any particular activity with respect to laminin and collagen IV.
  • Ursolic acid/oleanolic acid, sodium salt stimulated the production of collagen IV.
  • the effect observed was less pronounced than with the gel of palmitoyl pentapeptide-Lys-Thr-Thr-Lys-Ser; this effect is, however, apparently reproducible (reproduced with the mixtures containing ursolic acid/oleanolic acid, sodium salt).
  • Reconstructed 13 day epidermis models of the Skinethic type (4 cm 3 ) were used, cultivated in Skinethic medium.
  • the expression of the messengers ⁇ 2 ⁇ 1 integrin and collagen IV was verified in the reconstructed epidermis models by the RT polymerase chain reaction method (RT-PCR).
  • 20 epidermis models were treated with the formulations or the placebo applied topically in a quantity of 5 mg/cm 2 per epidermis (20 ⁇ l).
  • Four epidermis models were treated with 20 ⁇ l for each product; for each treatment, two epidermis models were cultured for 18 h and extracted for analysis; the two other epidermis models of each batch were again treated and re-cultured for 48 additional hours before extraction (72 h treatment in total).
  • RNA were then analysed by Northern blotting and the proteins by Southern blotting.
  • the DNA probes below were prepared from fragments of cDNA produced during the preliminary steps, after reamplification and purification.
  • the antisense strand of each cDNA was amplified using the following reaction mixture (25 ⁇ l; final concentrations): 25 U/ml RedTaq (Sigma D4309); 2.5 ⁇ l buffer RedTaq 10x; 20 ⁇ M dTTP; 20 ⁇ M dCTP; 20 ⁇ M dGTP; 2 ⁇ M [ ⁇ - 32 P]-dATP (15 ⁇ l, 150 ⁇ Ci, 3000 Ci/mmole, Amersham PB10204); 1 ng/ ⁇ l purified cDNA; 1 ⁇ M antisense primer (-).
  • PCR conditions 94 °C 2 min; then 30 times the sequence (95 °C 1 min, 55 °C 1 min, 72 °C 2 min), then 1 elongation cycle of 7 min at 72 °C then purification of the three probes over 3 Chroma Spin- 200 columns (Clontech S0269) according to the supplier's directions; purification monitored by liquid scintillation counting; collection of the fractions relating to each probe.
  • the epidermis models were separated from their boat and frozen immediately (-80 °C) in 1.25 ml of Tri-Reagent (TR, Sigma T9424) in an Eppendorf tube without RNase.
  • the proteins were repurified from the water/solvent interfaces derived from the purification protocol for the RNA.
  • the total protein fraction was prepared as specified in the protocol for using Tri-Reagent.
  • the proteins were finally dissociated in an SDS electrophoresis depot buffer (SDS PAGE); the final concentrations of SDS and 2-mercaptoethanol were 2%.
  • the proteins were separated by SDS-PAGE (8% acrylamide gels) and transferred (electric transfer in a liquid medium) onto nitrocellulose (Hybond, ECL, Amersham). In each series, controls in the absence of primary antibodies were carried out. The membranes were saturated by incubation for 16 hours (4 °C) in a PBS buffer/0.05% Tween 20/5% skimmed milk (PBSTL). The strips of control wells without primary antibody were cut out for separate treatment (incubation with the peroxidase conjugate only). After washing, the specific antigen sites were labelled with the primary antibodies in the dilutions indicated in PBSTL (see table below) for 1 hour at 37 °C.
  • the primary antibodies fixed were revealed by an anti-immunoglobulin-peroxidase conjugate. After extensive washing in PBST, the peroxidase activity was detected by the ECL method Enhanced ChemiLuminescence, Amersham) on Kodak MP film. The images were captured on GelPrint 2000i (BioPhotonics Corp.); the densitometric analyses were obtained using One-D-Scan software (Scanalytics).
  • RNA of all the samples was quantified; the same amount of RNA was deposited for all the samples treated.
  • the quantity of actin messengers must be stable in the absence of profound modifications of the expression profile of the cell genes (hyperproliferation, cytotoxicity).
  • the amount of actin messenger measured was relatively stable after 18 h of treatment; larger fluctuations were observed at time 72 h.
  • the measurement of the expression of the various markers in each sample was related to the relative expression of actin in the same sample.
  • Formulation F1 had a tendency to stimulate expression at 18 h (+ 16% compared with the reference) and at 72 h (+ 12%).
  • F2 also had a tendency to stimulate expression, at 72 h only (+ 12% compared with the reference).
  • Formulations F1 and F4 had a tendency to stimulate expression at time 18 h (of the order of + 20% compared with the reference). All the treatments inhibited the expression of collagen IV at time 72 h; this effect is apparently linked with a great intensity of marking of collagen IV in the placebo, at 72 h.
  • the immunoenzyme analysis was carried out on repurified protein fractions and after separation by SDS-PAGE. Actin (reference)
  • the actin band was perfectly clear and relatively homogeneous within each group of samples (18 h and 72 h; one gel per treatment time).
  • the epidermis extracts treated with F1 for 18 h had an intensity of marking of collagen IV greater than that of the references (+ 53% compared with the reference). The effect was less pronounced at time 72 h. These results confirm those obtained by Northern blotting.
  • ursolic acid and palmitoyl pentapeptide both increase the neosynthesis of 2 ⁇ 1 integrin without having a synergistic effect between them.
  • these two compounds each have a minor effect on the neosynthesis of collagen IV; on the other hand, at 72 hours, they have a considerable synergistic effect when they are used together.
  • the peptide extract of white lupin although having a negligible effect on the neosynthesis of ⁇ 2 ⁇ 1 integrin, has a very good activity on the neosynthesis of collagen IV at 72 hours.
  • Experiment 3 test with 3 compounds in mixture in comparison with the separate compounds, according to the same protocol as above and involving only the analysis of the expression of collagen IV.
  • ursolic acid/oleanolic acid shows an increase in the neosynthesis of collagen IV compared with the placebo, whereas the mixture of the three compounds shows a significantly greater increase in the neosynthesis of collagen IV with an obvious synergistic effect.
  • experimenters applied the composition of example 1 twice daily for 8 weeks in the usual quantity to the face as a whole, around the eyes, and to the neck.
  • the self-assessment questionnaires reflected a very favourable perception of the composition of example 1 by a very large majority of the volunteers, both as regards its cosmetic qualities and its efficacy; it was considered to be effective or very effective both in terms of its anti-wrinkle effect and firming effect by 91% of the volunteers, and 87.5% of the volunteers would buy the product which they rated 8/10 on average.
  • composition of example 2 were studied on a population of 34 Caucasian women with an average age of 52, 17 of whom were of phototype HI and 17 of phototype IV as regards skin type: 15 with a slightly dry skin and 19 with a moderately dry skin.
  • experimenters applied the composition of example 2 twice daily for 8 weeks in the usual quantity to the face as a whole, around the eyes and to the neck, and to the forearm.
  • the anti-wrinkle effect was characterised clinically by a significant reduction in skin slackness, the quantity of wrinkles and their depth; these improvements were statistically significant from the first month of treatment. A reduction in the length of the furrows also commenced in a significant manner during the second month of treatment.
  • the self-assessment questionnaires reflected a very favourable perception of the product tested by a very large majority of the volunteers, both as regards its cosmetic qualities and its efficacy; it was considered to be effective or very effective as a moisturiser, anti-wrinkle and firming agent by 91% of the volunteers, and 82% of the volunteers would buy the product which they rated 8/10 on average.

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Abstract

Cette invention concerne des compositions cosmétiques renfermant au moins un composé qui stimule la néosynthèse d'un moins un composant important de la jonction dermo-épidermique.
PCT/EP2001/009652 2000-08-21 2001-08-20 Compositions cosmetiques WO2002015869A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP01969626A EP1408925A1 (fr) 2000-08-21 2001-08-20 Compositions cosmetiques

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0010773A FR2813018B1 (fr) 2000-08-21 2000-08-21 Compositions cosmetiques renfermant au moins un compose stimulant la neosynthese des laminines, et/ou de l'integrine alpha-2 beta-1 et/ou du collagene iv de la jonction dermo- epidermique
FR00/10773 2000-08-21

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WO2002015869A1 true WO2002015869A1 (fr) 2002-02-28
WO2002015869A9 WO2002015869A9 (fr) 2002-06-13

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1566170A1 (fr) * 2004-02-20 2005-08-24 Beiersdorf AG Produit pour le soin de la peau contenant acide ursolique et un extrait de gingko
BE1020210A3 (fr) * 2011-09-06 2013-06-04 Auriga Internat Composition dermatologique a base de fragments d'hyaluronate ou d'acide hyaluronique.
EP2510919A3 (fr) * 2010-12-28 2014-08-13 Sami Labs Limited Composition de peptide d'oléanoyle et procédé de traitement du vieillissement de la peau
WO2016001430A1 (fr) * 2014-07-03 2016-01-07 Laboratoires Expanscience∅∅ Extraits peptidiques de lupin et fermete de la peau
CN105979968A (zh) * 2013-12-09 2016-09-28 Newmedic股份公司 具有持久性的透明质酸凝胶组合物
WO2018081779A1 (fr) 2016-10-31 2018-05-03 Sytheon Limited Compositions et procédés d'amélioration de la peau
WO2018236069A1 (fr) * 2017-06-21 2018-12-27 코오롱인더스트리 주식회사 Composition cosmétique respectueuse de l'environnement pour l'hydratation et l'amélioration de l'élasticité de la peau
KR20180138515A (ko) * 2017-06-21 2018-12-31 코오롱인더스트리 주식회사 피부 보습 및 탄력 증진용 친환경 화장료 조성물
WO2020192865A1 (fr) * 2019-03-22 2020-10-01 Symrise Ag Peptides de plante et leurs utilisations
EP3554461B1 (fr) 2016-12-16 2021-03-24 L'oreal Composition cosmétique comprenant des corps gras solides et un polymère gélifiant

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Publication number Priority date Publication date Assignee Title
EP1327438A1 (fr) * 2002-01-12 2003-07-16 Dr. Scheller Cosmetics AG Composition cosmetique et son application
FR2848116B1 (fr) * 2002-12-10 2007-01-05 Nuxe Lab Composition cosmetique comprenant un inhibiteur des metallo-proteinases et un lipopeptide.

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WO1998013019A1 (fr) * 1996-09-27 1998-04-02 Unilever Plc Compositions pour le soin de la peau contenant un acide, et un retinoide
JPH1112122A (ja) * 1997-06-20 1999-01-19 Pola Chem Ind Inc 皮膚改善化粧料
FR2778565A1 (fr) * 1998-05-14 1999-11-19 Silab Sa Procede d'extraction de principes actifs vegetaux a partir de graines de lupin blanc doux, extrait obtenu et composition utilisant au moins une fraction de cet extrait
FR2779059A1 (fr) * 1998-05-29 1999-12-03 Guerlain Procede de traitement cosmetique pour lutter contre les effets du vieillissement cutane; nouvelles compositions cosmetiques pour sa mise en oeuvre
FR2779058A1 (fr) * 1998-05-29 1999-12-03 Dior Christian Parfums Utilisation d'au moins une saponine ou un sapogenol cosmetiquement acceptable, comme agent cosmetique destine a augmenter la quantite de collagene iv dans la jonction dermo-epidermique
FR2783169A1 (fr) * 1998-09-15 2000-03-17 Sederma Sa Utilisation cosmetique ou dermopharmaceutique de peptides pour la cicatrisation et pour l'amelioration de l'aspect cutane lors du vieillissement naturel ou accelere (heliodermie, pollution)
FR2792202A1 (fr) * 1999-04-19 2000-10-20 Pharmascience Lab Extrait peptidique de lupin et composition pharmaceutique ou cosmetique ou nutraceutique comprenant un tel extrait
WO2000062743A2 (fr) * 1999-04-19 2000-10-26 The Procter & Gamble Company Compositions de soin pour la peau contenant une combinaison de principes actifs de soin pour la peau
FR2797186A1 (fr) * 1999-08-02 2001-02-09 Silab Sa Procede d'extraction d'un principe actif a partir de levures, notamment pour le traitement des rides, principe actif obtenu, compositions cosmetiques et traitement adaptes

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1566170A1 (fr) * 2004-02-20 2005-08-24 Beiersdorf AG Produit pour le soin de la peau contenant acide ursolique et un extrait de gingko
EP2510919A3 (fr) * 2010-12-28 2014-08-13 Sami Labs Limited Composition de peptide d'oléanoyle et procédé de traitement du vieillissement de la peau
BE1020210A3 (fr) * 2011-09-06 2013-06-04 Auriga Internat Composition dermatologique a base de fragments d'hyaluronate ou d'acide hyaluronique.
CN105979968A (zh) * 2013-12-09 2016-09-28 Newmedic股份公司 具有持久性的透明质酸凝胶组合物
EP3081232A4 (fr) * 2013-12-09 2017-06-14 New Medic Co., Ltd. Composition de gel d'acide hyaluronique ayant une propriété de libération prolongée
JP2017519787A (ja) * 2014-07-03 2017-07-20 ラボラトワール エクスパンシアンス ルピンペプチド抽出物および皮膚の張り
FR3023164A1 (fr) * 2014-07-03 2016-01-08 Expanscience Lab Extraits peptidiques de lupin et fermete de la peau
WO2016001430A1 (fr) * 2014-07-03 2016-01-07 Laboratoires Expanscience∅∅ Extraits peptidiques de lupin et fermete de la peau
JP6999267B2 (ja) 2014-07-03 2022-01-18 ラボラトワール エクスパンシアンス ルピンペプチド抽出物および皮膚の張り
CN106470670A (zh) * 2014-07-03 2017-03-01 科学发展实验室 羽扇豆肽提取物和皮肤紧实度
US10463593B2 (en) 2014-07-03 2019-11-05 Laboratoires Expanscience Lupin peptide extracts and skin firmness
WO2018081779A1 (fr) 2016-10-31 2018-05-03 Sytheon Limited Compositions et procédés d'amélioration de la peau
EP4299077A2 (fr) 2016-10-31 2024-01-03 Sytheon Limited Compositions et procédés d'amélioration de la peau
EP3554461B1 (fr) 2016-12-16 2021-03-24 L'oreal Composition cosmétique comprenant des corps gras solides et un polymère gélifiant
KR101990097B1 (ko) * 2017-06-21 2019-06-18 코오롱인더스트리 주식회사 피부 보습 및 탄력 증진용 친환경 화장료 조성물
CN110536675A (zh) * 2017-06-21 2019-12-03 可隆工业株式会社 用于皮肤保湿以及增加弹性的绿色环保化妆料组合物
KR20180138515A (ko) * 2017-06-21 2018-12-31 코오롱인더스트리 주식회사 피부 보습 및 탄력 증진용 친환경 화장료 조성물
WO2018236069A1 (fr) * 2017-06-21 2018-12-27 코오롱인더스트리 주식회사 Composition cosmétique respectueuse de l'environnement pour l'hydratation et l'amélioration de l'élasticité de la peau
WO2020192865A1 (fr) * 2019-03-22 2020-10-01 Symrise Ag Peptides de plante et leurs utilisations

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FR2813018B1 (fr) 2004-02-06

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