EP2753301A2 - Wirkstoff aus torulaspora delbrueckii und kosmetische verwendung zur verbesserung und/oder reparatur der barrierefunktion der haut - Google Patents

Wirkstoff aus torulaspora delbrueckii und kosmetische verwendung zur verbesserung und/oder reparatur der barrierefunktion der haut

Info

Publication number
EP2753301A2
EP2753301A2 EP12773013.3A EP12773013A EP2753301A2 EP 2753301 A2 EP2753301 A2 EP 2753301A2 EP 12773013 A EP12773013 A EP 12773013A EP 2753301 A2 EP2753301 A2 EP 2753301A2
Authority
EP
European Patent Office
Prior art keywords
active ingredient
skin
cosmetic
composition
brueckii
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Withdrawn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
EP12773013.3A
Other languages
English (en)
French (fr)
Inventor
Jean Paufique
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.)
Societe Industrielle Limousine dApplication Biologique SA SILAB
Original Assignee
Societe Industrielle Limousine dApplication Biologique SA SILAB
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 Societe Industrielle Limousine dApplication Biologique SA SILAB filed Critical Societe Industrielle Limousine dApplication Biologique SA SILAB
Publication of EP2753301A2 publication Critical patent/EP2753301A2/de
Withdrawn legal-status Critical Current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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9728—Fungi, e.g. yeasts
    • 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

Definitions

  • the present invention relates to the cosmetic use of Torulaspora brueckii as a cosmetic active ingredient, in particular for improving and / or repairing the barrier function of the skin, as well as a cosmetic skin care process.
  • the invention also relates to an active ingredient derived from Torulaspora de / brueckii, to a process for obtaining the same and to cosmetic compositions containing this active ingredient.
  • the barrier function of the skin is essential for maintaining the hydration and physical properties of the skin tissue. It results from epidermal differentiation, a sequential and oriented process in which keratinocytes undergo numerous morphological and metabolic changes resulting in stratification of the epidermis and formation of the stratum corneum.
  • the skin is continually subjected to aggressions that lead to the destructuring of its barrier function.
  • the alteration of the skin barrier has repercussions on the state of the skin. It can in particular result in a hydration disorder: the skin loses its impermeability, it becomes dehydrated and its insensible loss of water increases.
  • Patent F -0953114 describes an effective solution for improving and / or repairing the cutaneous barrier function, by using in a cosmetic composition at least one agent increasing the expression of the nicotinic acetylcholine nAChR receptors of the skin cells.
  • the objective of the present invention is to propose a specific active principle having such an effect.
  • the invention aims to use an active principle derived from Toru / aspora de / brueckii.
  • Toru / aspora de / brueckii is a yeast isolated from marzipan. It belongs to the branch of ascomycetes, the class Saccharomycetes, the order Saccharomycetae, the family Saccharomycetaceae, the genus Toru / Aspora, the species brueckii. It is also known under the following synonyms: Saccharomyces de / brueckii, Saccharomyces fermentati, Saccharomyces rose.
  • This yeast is used in the food industry for its fermenting power.
  • Toru / aspora de / brueckii has significant effects on the skin with very interesting cosmetic properties.
  • the invention therefore relates to an active ingredient derived from Toru / aspora de / brueckii, as a cosmetic active ingredient in a composition intended to be applied to the skin, for improving and / or repairing the cutaneous barrier function.
  • the invention also specifically relates to a cosmetic active ingredient comprising structural peptides obtained from Toru / aspora de / brueckii as well as a process for obtaining this active ingredient and cosmetic compositions including at least one such active ingredient.
  • the active ingredient according to the invention is obtained by hydrolysis of Toru / aspora de / brueckii.
  • the subject of the invention is also a cosmetic skin care method for improving and / or repairing the cutaneous barrier function.
  • the invention relates to an active ingredient derived from Torulaspora delbrueckii for its application as an active ingredient in a composition for topical application.
  • the invention relates to the cosmetic use of an active ingredient derived from Torulaspora delbrueckii as a cosmetic active ingredient in or for the preparation of a cosmetic composition.
  • Active principle within the meaning of the invention means any molecule or mixture of molecules having a cosmetic efficacy on the skin and not an excipient.
  • active principle derived from Torulaspora delbrueckii or obtained from Torulaspora delbrueckii within the meaning of the invention is meant any molecule or mixture of molecules derived from the structure of the ferment Torulaspora delbrueckii: these may be native molecules of yeast or molecules obtained by hydrolysis of the yeast. Preferably, it is a hydrolyzate of Torulaspora delbrueckii.
  • active ingredient in the sense of the invention excludes the molecules produced by fermentation of Torulaspora delbrueckii.
  • hydrolyzate any extract obtained from Torulaspora delbrueckii, comprising at least one enzymatic or chemical hydrolysis step, preferably enzymatic.
  • the invention aims in particular the use of an active ingredient from Torulaspora delbrueckii as a restructuring cosmetic active ingredient.
  • an active ingredient from Torulaspora delbrueckii ' can indeed be used as a cosmetic agent on the skin to improve and / or repair the cutaneous barrier function.
  • the presence in sufficient quantity of peptides, in particular peptides with a molecular weight of less than 2000 Da, in the active ingredient of Torulaspora delbrueckii makes it possible in particular to confer on it this cosmetic activity.
  • the active ingredient derived from Torulaspora brueckii acts in particular on the nicotinic pathway of acetylcholine nAChRs of the skin.
  • NAChRs are ion channels whose opening is regulated by acetylcholine. They specialize in the transmembrane transport of cations and control many processes involved in the homeostasis of the epidermis. NAChR stimulation induces calcium and sodium influx and potassium efflux, which allows fine regulation of intracellular ionic fluxes and synchronization of metabolic events occurring throughout epidermal differentiation.
  • nACHRs Controlling the influx of calcium into keratinocytes, nACHRs play a major role in regulating the cohesion and differentiation of keratinocytes, processes that are largely involved in the formation of an optimal barrier function.
  • the use on the skin of an active ingredient derived from Torulaspora brueckii can stimulate nAChRs and thus promote epidermal homeostasis.
  • the cohesion of the epidermis is based on the presence of complexes including adherent junctions of the epidermis, which provide strong adhesion between the keratinocytes and which are necessary for the formation and maintenance of the barrier function.
  • These junctions unite the actin cytoskeleton of two adjacent keratinocytes via a transmembrane glycoprotein located in the cytoplasmic membrane of the cells, E-cadherin.
  • these junctions In addition to their role as an intercellular anchor, these junctions also function as signaling platforms controlling cytoskeletal reshaping, cell migration and polarization of the epidermis.
  • the application of an active ingredient derived from Torulaspora brueckii on the skin makes it possible to stimulate interkeratinocyte adhesion, in particular by stimulating the synthesis of E-cadherin.
  • NAChRs are involved in terminal differentiation and cornification of keratinocytes. They influence in particular the expression by keratinocytes of cytokeratin 1 and 10, filaggrin and proteins involved in the formation of the horny envelope such as involucrine, loricrin and transglutaminase-1.
  • the application of an active principle derived from Torulaspora brueckii on the skin can stimulate the terminal differentiation of keratinocytes, including stimulating the synthesis of loricrine.
  • the invention therefore relates to an active ingredient derived from Torulaspora de / brueckii for its application as an active ingredient in a composition for topical application, the active ingredient and / or the composition being used to stimulate nAChRs present on the membranes of keratinocytes, and thus regulate epidermal homeostasis.
  • the active ingredient according to the invention and / or the composition comprising it can be used for:
  • the invention relates to the use of an active principle derived from Toru / aspora brueckii containing peptides with a molecular weight of less than 2000 Da, as described in the following.
  • the invention therefore relates to the use of an active principle derived from Toru / aspora brueckii ' as active ingredient in a composition for topical application.
  • the invention also relates to a particular cosmetic active ingredient comprising peptides obtained from Toru / aspora de / brueckii, preferably an active ingredient comprising peptides with a molecular weight of less than 2000 Da obtained from Toru / aspora de / brueckii.
  • the active ingredient according to the invention comprising peptides obtained from Toru / aspora de / brueckii is a hydrolyzate of Toru / aspora de / brueckii, and even more preferably an enzymatic hydrolyzate of Toru / aspora de / brueckii.
  • the active principle according to the invention comprises a peptide content greater than or equal to 42% relative to the total content of dry matter, preferably greater than 60%.
  • the cosmetic active ingredient according to the invention may also comprise ashes, carbohydrates and polyphenols.
  • the active ingredient according to the invention is preferably in liquid form. It may be defined by at least one of the characteristics set out below, all of them being preferred.
  • the solids content of an active principle derived from Toru / aspora de / brueckii according to the invention, measured by passing in an oven at 105 ° C. in the presence of sand until a constant weight is obtained, is included between 10 and 150 g / l, preferably between 18 and 28 g / l. H measurement:
  • the pH measured by the potentiometric method at ambient temperature leads to values between 4.0 and 7.0, preferably between 5.3 and 6.3.
  • Protein content assay is performed according to the method of LOW Y (Lowry et al., Protein measurement with the reagent reagent, J. Biol Chem, 193, 265-275, 1951).
  • the Folin reaction gives a blue color with certain amino acids. The coloration obtained is compared with that of a curve established with a standard serum.
  • the total protein content is preferably between 6.5 and 107 g / l, more preferably between 12 and 20 g / l.
  • the protein content can also be expressed as a percentage relative to the dry matter. It therefore preferably represents at least 42% by weight relative to the dry matter.
  • the characterization of the protein fraction of the active ingredient according to the invention is carried out by steric exclusion F.P.L.C (Fast Protein Liquid Chromatography).
  • the calibration of the column is carried out by the passage of defined molecular weight markers (Cytochrome C, Aprotinin,
  • the proteins of the active principle according to the invention are composed of at least 60% of peptides with a molecular weight of less than 2000 Da.
  • the raw ash content is determined by the weighing of residues from incineration at 550 ° C in an electric muffle furnace (VULCAN TM). The weight of the residue is calculated by deducting the tare. The raw ash content is expressed as a percentage relative to the dry matter.
  • the raw ash content of an active ingredient according to the invention is preferably between 25% and 31%.
  • the determination of the total sugar content can be carried out by the DUBOIS method (DUBOIS M. et al. , (1956), Analytical Chemistry, 28, No. 3, pp. 350-356) In the presence of concentrated sulfuric acid and from phenol, the reducing sugars give an orange-yellow compound From a standard range, the total sugar content of a sample can be determined.
  • the total sugar content is preferably between 6.2 and 7.7% by weight relative to the dry matter.
  • the molecular weights of the carbohydrates present in the active principle according to the invention are determined by means of high performance liquid chromatography (HPLC).
  • the carbohydrate fraction of the active ingredient according to the invention is composed of glucose, mannose and fructose, in the form of oligosaccharides with a degree of polymerization of less than or equal to 20 (molecular weight less than or equal to 3600 Da).
  • the phenolic compounds form colored compounds detectable at 715 nm.
  • the intensity of coloration is proportional to the amount of phenolic compounds.
  • the readings are made from a standard range of gallic acid ranging from 40 to 120 mg / l.
  • the results obtained for the standards allow to plot a straight optical density as a function of the concentration and the polyphenol level of the samples is read directly on this line.
  • the content of phenolic compounds of an active ingredient obtained from Toru / Aspora de / brueckii according to the invention is less than 0.4% in percentage relative to the dry matter.
  • a fraction B containing mainly sugars obtained by purifying the neutral carbohydrates of the active principle by successive adsorption of the cationic and anionic compounds on ionic resins,
  • fraction C consisting essentially of peptides, obtained by purifying the peptides by adsorption / elution on a cation exchange resin.
  • the study consists in comparing the effect of these different fractions assayed at 1% on the synthesis of loricrin, with the result obtained for the active ingredient according to the invention at 1%.
  • the test is carried out on normal human keratinocytes, according to the operating protocol described in point A.II of the section on evaluation of cosmetic efficacy. The results obtained are shown in the table below:
  • An active ingredient derived from Torulaspora delbrueckii according to the invention can be obtained by a process which makes it possible to obtain and concentrate the active principle in terms of peptides, in particular in terms of peptides with a molecular weight of less than 2000 Da. It includes at least the following steps:
  • At least one enzymatic hydrolysis with a view to obtaining peptides with a molecular weight of less than 2000 Da.
  • At least one enzymatic hydrolysis with a view to obtaining peptides with a molecular weight of less than 2000 Da
  • the method comprises at least the following steps:
  • the enzymatic hydrolysis is preferably carried out using a protease, under conditions making it possible to obtain peptides with a molecular weight of less than 2000 Da.
  • the active ingredient obtained is in the form of a clear liquid aqueous solution of light yellow color.
  • the present invention also covers cosmetic compositions including at least one active ingredient derived from Toru / aspora de / brueckii in different galenic forms, adapted for topical administration to the skin.
  • compositions may be in the form of oil-in-water emulsions, water-in-oil emulsions, multiple emulsions (water / oil / water or oil / water / oil) which may be microemulsions or nanoemulsions, or in the form of solutions, suspensions, hydrodispersion, aqueous gel or powders. They can be more or less fluid and have the appearance of a cream, a lotion, a milk, a serum, an ointment, a gel, a paste or a foam, or in solid form.
  • active ingredient (s) derived from Toru / aspora brueckii according to the present invention, preferably between 0.1% and 3%.
  • compositions comprise, in addition to the active ingredient, a physiologically acceptable and preferably cosmetically acceptable medium, that is to say which does not cause unacceptable sensations of discomfort for the user, such as redness, tightness or tingling.
  • compositions according to the invention may contain as adjuvant at least one compound chosen from:
  • oils which may be chosen in particular from silicone oils, linear or cyclic, volatile or non-volatile;
  • waxes such as ozokerite, polyethylene wax, beeswax or carnauba wax;
  • surfactants preferably emulsifiers, whether they are nonionic, anionic, cationic or amphoteric;
  • co-surfactants such as linear fatty alcohols
  • humectants such as polyols such as glycerine
  • compositions are especially intended for the care, treatment, protection of human skin against the effects of various internal or external aggression, in particular to improve the barrier function and / or the surface condition of the skin.
  • the invention aims at a cosmetic process for the care of human skin, intended to improve the barrier function and / or the surface condition of the skin, comprising the topical application to the skin of a composition containing a principle active ingredient derived from Toru / aspora de / brueckii, in particular a composition containing between 0.01 and 20% by weight of active principle (s) derived from Toru / aspora brueckii ' according to the present invention.
  • a cosmetic process for the care of human skin intended to improve the barrier function and / or the surface condition of the skin, comprising the topical application to the skin of a composition containing a principle active ingredient derived from Toru / aspora de / brueckii, in particular a composition containing between 0.01 and 20% by weight of active principle (s) derived from Toru / aspora brueckii ' according to the present invention.
  • Example 1 Process for Obtaining the Active Ingredient According to the Invention
  • An example of a process for obtaining an active ingredient according to the invention comprises the implementation of the following steps:
  • total protein content 16.2 g / l, ie 64.50% by weight relative to the dry matter
  • total sugar content 1.7 g / l, ie 6.95% by weight relative to the dry matter
  • Example 2 Use of an Active Ingredient According to the Invention in a Moisturizing Gel
  • Example 3 Use of an Active Ingredient According to the Invention in a Night Cream
  • the formulation is as follows:
  • BIOPHILIC H (Lucas Meyer) 2%
  • Example 4 Use of an Active Ingredient According to the Invention in a Gel
  • composition used for the in vivo tests is that of Example 4.
  • the effect of the active principle according to the invention on the differentiation and the adhesion of keratinocytes and its mechanism of action via the nACHRs pathway were studied thanks to the use of an antagonist and an agonist of the nAChRs evaluated. on the synthesis of loricrine (on human keratinocytes in monolayer and on reconstructed epidermis) and cadherin-E (on reconstructed epidermis).
  • the protocol used to validate the agonist and antagonist of nAChRs is illustrated by following for the synthesis of loricrin on reconstructed epidermis. It is also applicable for the synthesis of cadherin-E on reconstructed epidermis.
  • the inserts comprising the epidermis under construction are placed in a culture medium containing:
  • mecamylamine 1000 ⁇ l (reversible antagonist of nACHRs), or
  • the visualization is then performed on a microscope coupled to an image analysis system.
  • the intensity of the fluorescence (green color) is proportional to the synthesis of loricrine.
  • Nicotine 500 ⁇ 113% It is found that in the presence of mecamylamine, the synthesis of loricrin is reduced compared to the untreated control while it is increased during treatment with nicotine.
  • Mecamylamine can therefore be used as a nAChR antagonist and nicotine as a nACHR agonist.
  • This study aims to evaluate the effectiveness of an active ingredient according to the invention on keratinocyte differentiation by studying the synthesis of loricrine. It was carried out by Western Blot on normal human keratinocytes isolated from prepuces, according to the operating protocol described below.
  • human keratinocytes are inoculated and incubated at 37 ° C.
  • the cells are then incubated at 37 ° C.
  • the cell extracts are recovered and the Western blot assay is performed.
  • Active ingredient according to the invention 0.5% +75
  • the active ingredient according to the invention or nicotine increases the synthesis of loricrin by human keratinocytes. Tested at 1%, it increases this synthesis by 282% under the conditions of the study.
  • the active principle according to the invention thus makes it possible to stimulate keratinocyte differentiation, and this effect is mainly dependent on the nAChR pathway.
  • This study aims to evaluate the ability of an active ingredient according to the invention to promote the maturation of the epidermis, the construction of a cohesive and stratified epidermis.
  • This epidermal construct was evaluated using:
  • a terminal differentiation marker loricrine
  • cadherin-E a marker involved in the formation of adherent junctions
  • the operating protocol is described following. At 0, the human keratinocytes are cultured in a culture medium and then seeded on an insert. The culture medium is changed every 2 days in the presence of the active ingredient according to the invention to 1% with or without mecamylamine 1000 ⁇ .
  • the inserts are recovered, fixed, dehydrated and included in paraffin.
  • Sections are then made and immunohistological labeling of loricrine or E-cadherin is performed.
  • the visualization is then performed on a microscope coupled to an image analysis system.
  • the intensity of the fluorescence (green color) is proportional to the synthesis of loricrine or cadherin.
  • the active ingredient according to the invention accelerates the construction of an epidermis and promotes cohesion and maturation by stimulating synthesis:
  • loricrin a marker of terminal keratinocyte differentiation
  • E-cadherin a protein involved in the formation of adherent junctions.
  • the objective of the study is to quantify in vivo on volunteers the effect of the active principle according to the invention formulated at 3% in gel-emulsified on the insensible loss of water (PIE) of the skin, in comparison with the placebo after an artificial disruption of the barrier function with a detergent.
  • PIE insensible loss of water
  • the cutaneous barrier plays a regulating role in the water balance of the skin. When this is harmed, it appears disturbances in the regulation of water exchanges. The water then migrates more easily to the outside environment, which increases the PIE. On the other hand, if the state of the cutaneous barrier improves, the values of water loss decrease because the regulation of the exchanges in water is ensured in a correct way.
  • the present study was performed at the level of the arms on 19 female volunteers, with normal skin.
  • the measurements were carried out using a Tewameter®, a device equipped with a probe that measures the vapor gradient between the skin surface and the ambient air. This measurement makes it possible to appreciate the exchanges of water between the cutaneous surface and the surrounding environment.
  • measurement zones are determined at the level of the upper arms.
  • the measurement zones are as follows:
  • the objective of the study is to quantify in vivo on volunteers the effect of the active principle according to the invention formulated at 3% in gel-emulsified on the insensible loss of water (PIE) of the skin, in comparison with the placebo on skin whose barrier function has previously been artificially disturbed by a detergent, Sodium Lauryl Sulfate (SLS).
  • PIE insensible loss of water
  • SLS Sodium Lauryl Sulfate
  • measurement zones at the level of the calves are determined on each volunteer.
  • the measurement zones are as follows:
  • the volunteers also apply twice daily the product containing the active ingredient according to the invention or the placebo on the zones studied.
  • the active ingredient according to the invention formulated at 3% gel-emulsified decreases the PIE of a skin having an SLS-impaired barrier function of 5, 4% compared to placebo.
  • the acquisitions (corresponding to horizontal sections of the skin) were carried out using a confocal microscope on the volunteers at the level of the stratum corneum after local application of fluorescein.
  • Fluorescein acts as a contrast agent. It diffuses into tissues and spaces interstitials freely, and does not bind specifically. It interferes with the cells of the stratum corneum and accumulates in thicker areas such as scales.
  • the acquisition is carried out using a 445 nm laser in fluorescence mode.
  • the images obtained are then processed and visually analyzed blind by a trained jury, according to the parameters indicated in the following table:
  • measurement zones at the level of the calves are determined on each volunteer.
  • the measurement zones are as follows:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Dermatology (AREA)
  • Biotechnology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Botany (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)
  • Tropical Medicine & Parasitology (AREA)
EP12773013.3A 2011-09-05 2012-09-04 Wirkstoff aus torulaspora delbrueckii und kosmetische verwendung zur verbesserung und/oder reparatur der barrierefunktion der haut Withdrawn EP2753301A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1157843A FR2979541B1 (fr) 2011-09-05 2011-09-05 Principe actif issu de torulaspora delbrueckii et utilisation cosmetique pour ameliorer et/ou reparer la fonction barriere de la peau
PCT/FR2012/051977 WO2013034845A2 (fr) 2011-09-05 2012-09-04 Principe actif issu de torulaspora delbrueckii et utilisation cosmetique pour ameliorer et/ou reparer la fonction barriere de la peau

Publications (1)

Publication Number Publication Date
EP2753301A2 true EP2753301A2 (de) 2014-07-16

Family

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EP12773013.3A Withdrawn EP2753301A2 (de) 2011-09-05 2012-09-04 Wirkstoff aus torulaspora delbrueckii und kosmetische verwendung zur verbesserung und/oder reparatur der barrierefunktion der haut

Country Status (4)

Country Link
US (1) US20140220069A1 (de)
EP (1) EP2753301A2 (de)
FR (1) FR2979541B1 (de)
WO (1) WO2013034845A2 (de)

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FR3008891B1 (fr) * 2013-07-29 2016-10-14 Soc Ind Limousine D'application Biologique Principe actif a application cutanee obtenu a partir de metschnikowia pulcherrima et utilisation cosmetique
FR3061656B1 (fr) 2017-01-09 2019-05-24 Societe Industrielle Limousine D'application Biologique Hydrolysat de pichia minuta et utilisation cosmetique pour lutter contre la chute des cheveux et favoriser leur repousse
JP2023079983A (ja) * 2021-11-27 2023-06-08 共栄化学工業株式会社 育毛用組成物

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WATANABE Y ET AL: "Cloning and sequencing of phospholipase B gene from the yeast Torulaspora delbrueckii", FEMS MICROBIOLOGY LETTERS, WILEY-BLACKWELL PUBLISHING LTD, GB, vol. 124, no. 1, 15 November 1994 (1994-11-15), pages 29 - 34, XP023971044, ISSN: 0378-1097, [retrieved on 19941115], DOI: 10.1111/J.1574-6968.1994.TB07257.X *

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FR2979541B1 (fr) 2013-10-04
WO2013034845A3 (fr) 2013-10-24
FR2979541A1 (fr) 2013-03-08
WO2013034845A2 (fr) 2013-03-14
US20140220069A1 (en) 2014-08-07

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