FR2700953A1 - Use of certain microorganism strains as a new source of ceramides and of sphingolipids for cosmetic use - Google Patents

Use of certain microorganism strains as a new source of ceramides and of sphingolipids for cosmetic use Download PDF

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FR2700953A1
FR2700953A1 FR9301074A FR9301074A FR2700953A1 FR 2700953 A1 FR2700953 A1 FR 2700953A1 FR 9301074 A FR9301074 A FR 9301074A FR 9301074 A FR9301074 A FR 9301074A FR 2700953 A1 FR2700953 A1 FR 2700953A1
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cosmetic compositions
compositions according
lipids
biomass
extracted
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FR2700953B1 (en
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Greff Daniel
Lindet Brigitte
Delepine Sylviane
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Sederma SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • 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
    • A61K8/99—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from microorganisms other than algae or fungi, e.g. protozoa or bacteria
    • 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
    • A61Q5/00—Preparations for care of the hair

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

The patent describes how complex lipids, ceramides, sphingolipids and sterols can be obtained from certain strains of microorganisms, in particular strains of Flavobacterium species, Acetobacter species and Aspergillus species. The process comprises the extraction of the dry biomass by organic solvents, the purification and the enrichment of the sphingolipids thus extracted and their use in cosmetics.

Description

Les sphingolipides constituent une classe de lipides complexes très recherchée pour l'utilisation cosmétique du fait que la peau, en particulier la couche cornée qui constitue le domaine d'application privilégié de la cosmétique, en contient une large proportion.Sphingolipids constitute a class of complex lipids which is highly sought after for cosmetic use because the skin, in particular the stratum corneum which constitutes the preferred field of application of cosmetics, contains a large proportion thereof.

Les sources de sphingolipides naturels, en particulier des céramides, sont pourtant rares: on peut extraire ces lipides à partir des peaux de mammifères, également à partir du tissu nerveux bovin ou porcin (cerveau, moelle). L'apparition de la maladie de l'encéphalite spongiforme bovine en Europe a provoqué un rejet des produits d'extraction animale pour toute utilisation cosmétique.The sources of natural sphingolipids, in particular ceramides, are however rare: these lipids can be extracted from mammalian skins, also from bovine or porcine nervous tissue (brain, marrow). The appearance of bovine spongiform encephalitis disease in Europe has caused rejection of animal extraction products for any cosmetic use.

Les plantes et les céréales contiennent des sphingolipides, mais à de très faibles concentrations, telles que l'extraction ne s'avère pas économiquement valable.Plants and cereals contain sphingolipids, but at very low concentrations, such as extraction is not economically viable.

La synthèse chimique des céramides ab inifio, à partir de molécules également synthétiques (pour la distinguer de l'hémisynthèse qui utiliserait des fragments sphingolipidiques obtenus par extraction), est très difficile à l'échelle industrielle.The chemical synthesis of ab inifio ceramides, from also synthetic molecules (to distinguish it from hemisynthesis which would use sphingolipid fragments obtained by extraction), is very difficult on an industrial scale.

L'objet de notre brevet est la découverte que certaines souches de microorganismes, en particulier des champignons de la famille Aspergillus sadd. et des bactéries de Flavobacterium spp. ainsi que d' Acetobacter spp. contiennent des céramides et/ou des sphingolipides en quantité suffisante pour une extraction rentable. The subject of our patent is the discovery that certain strains of microorganisms, in particular fungi of the Aspergillus sadd family. and bacteria of Flavobacterium spp. as well as Acetobacter spp. contain sufficient ceramides and / or sphingolipids for cost-effective extraction.

La littérature scientifique décrit en effet un certain nombre de souches microbiennes qui renferment des sphingolipides en faible quantité.Scientific literature indeed describes a certain number of microbial strains which contain sphingolipids in small quantities.

Un screening extensif a permis de trouver d'autres souches particulières pour lesquelles le rendement lipidique en extraction est élevé, le contenu en sphingolipides etlou céramides est également élevé, et la composition globale des lipides présente un intérêt cosmétique. En outre, ces souches sont facilement cultivables en fermenteur, la biomasse constitue donc une source intéressante pour l'obtention des sphingolipides et/ou céramides destinés à l'application cosmétique.Extensive screening has made it possible to find other particular strains for which the lipid yield in extraction is high, the content of sphingolipids and / or ceramides is also high, and the overall composition of the lipids is of cosmetic interest. In addition, these strains are easily cultivated in a fermenter, biomass therefore constitutes an interesting source for obtaining sphingolipids and / or ceramides intended for cosmetic application.

Des exemples vont illustrer le champ d'application du brevet.Examples will illustrate the scope of the patent.

Une souche sauvage d'Aspergillus orizae est cultivée sur un milieu riche composé de 759/1 de polysaccharides et de 209/1 de peptone de soja pendant une durée de 24 heures. La fermentation procède par étapes: inoculum de 11, croissance jusqu'à une densité microbienne de 13 g/l, la biomasse est ensuite transférée dans un fermenteur de 20 1, cultivée dans des conditions équivalentes, transférée dans un fermenteur de 5001 pour finalement être fermentée dans un volume de 10 m3.A wild strain of Aspergillus orizae is cultivated on a rich medium composed of 759/1 of polysaccharides and 209/1 of soy peptone for a period of 24 hours. Fermentation proceeds in stages: inoculum of 11, growth to a microbial density of 13 g / l, the biomass is then transferred to a fermenter of 20 l, cultivated under equivalent conditions, transferred to a fermenter of 5001 to finally be fermented in a volume of 10 m3.

A l'arrêt de la fermentation après 48 heures, on recolte la biomasse par filtration, on la sèche par chauffage à l'air chaud et on procède à l'extraction par chloroforme (3% de matière sèche) en deux étapes de 5 heures chacune. Après filtration et décoloration sur charbon, on évapore le chloroforme. When the fermentation stops after 48 hours, the biomass is harvested by filtration, it is dried by heating with hot air and extraction is carried out with chloroform (3% dry matter) in two 5-hour stages each. After filtration and bleaching on charcoal, the chloroform is evaporated.

Le résidu lipidique ainsi obtenu (rendement sur matière sèche: 3-5% environ) contient entre 5 et 15% de céramides, de sphingolipides et de cérébrosides, entre 50 et 75% de lipides saponifiables et entre 5 à 20% de stérols et autres lipides insaponifiables.The lipid residue thus obtained (yield on dry matter: around 3-5%) contains between 5 and 15% of ceramides, sphingolipids and cerebrosides, between 50 and 75% of saponifiable lipids and between 5 and 20% of sterols and other unsaponifiable lipids.

Cette procédure n'est en aucun cas limitative. Les conditions de fermentation, de milieu, de durée, d'échelle peuvent varier dans de larges proportions connues par l'homme du métier.This procedure is in no way limiting. The fermentation, medium, duration, and scale conditions can vary within wide proportions known to those skilled in the art.

Pour l'utilisation cosmétique, on peut procéder à une étape supplémentaire: après saponification par un milieu alcalin (lessive de soude ou de potasse), on recolte la fraction d'insaponifiable maintenant enrichie à environ 30% en céramides et sphingolipides. La mise en évidence de la présence des céramides en particulier est effectuée par différents dosages:
Une méthode de détection et de quantification des groupes NH2 a été mise au point. Quand on l'applique aux lipides recoltés par l'extraction au chloroforme, on ne détecte que très peu d'amines libres ( < 0.5%). Après hydrolyse acide des lipides, on trouve une quantité de lipides avec un groupe NH2, correspondant aux molécules de sphingosine libérées par l'hydrolyse, équivalent à 15-20% de céramides, cérébrosides et sphingolipides initiaux.For cosmetic use, an additional step can be carried out: after saponification with an alkaline medium (sodium hydroxide or potassium hydroxide solution), the unsaponifiable fraction is harvested now enriched with approximately 30% in ceramides and sphingolipids. The detection of the presence of ceramides in particular is carried out by different dosages:
A method for detecting and quantifying NH2 groups has been developed. When applied to lipids harvested by chloroform extraction, only very few free amines (<0.5%) are detected. After acid hydrolysis of the lipids, there is an amount of lipids with an NH2 group, corresponding to the sphingosine molecules released by the hydrolysis, equivalent to 15-20% of ceramides, cerebrosides and initial sphingolipids.

Un dosage HPLC des lipides insaponifiables après saponification de cette fraction confirme la présence des céramides en pourcentage élevé (2030%). An HPLC assay of the unsaponifiable lipids after saponification of this fraction confirms the presence of the ceramides in a high percentage (2030%).

Des étapes supplémentaires de purification par chromatographie liquide ou supercritique permettent d'atteindre des concentrations en céramides et/ou sphingolipides encore supérieures ( > 80%). Selon le procédé d'extraction et de purification, les extraits contiennent en outre 0 à 50% de stérols et O à 99% de lipides saponifiables.Additional purification steps by liquid or supercritical chromatography make it possible to reach even higher concentrations of ceramides and / or sphingolipids (> 80%). Depending on the extraction and purification process, the extracts also contain 0 to 50% sterols and 0 to 99% saponifiable lipids.

D'autres espèces d'Aspergillus, tel l'Aspergillus niger. l'Aspergillus fumigatus peuvent être utilisées. Les conditions de fermentation et la composition ainsi que le rendement sont légèrement différents d'un germe à l'autre.Other Aspergillus species, such as Aspergillus niger. Aspergillus fumigatus can be used. The fermentation conditions and the composition as well as the yield are slightly different from one germ to another.

Une autre voie d'obtention des sphingolipides et des céramides à partir de microorganismes consiste en la culture de Flavobacterium devorans sur un milieu composé de 15g/l de peptone de gélatine et des sels minéraux.Another way of obtaining sphingolipids and ceramides from microorganisms consists in the culture of Flavobacterium devorans on a medium composed of 15 g / l of gelatin peptone and mineral salts.

Les procédés d'extraction, de purification et d'enrichissement sont semblables à l'exemple précédent et sont bien connus de l'homme du métier.The extraction, purification and enrichment methods are similar to the previous example and are well known to those skilled in the art.

De même, une extraction de la biomasse d'Acetobacter pasteurianus permet d'obtenir des céramides. Néanmoins, la composition de l'extrait lipidique est moins faborable, puisque le pourcentage de céramides est plus faible, on trouve une quantité plus importante d'amines libres dans l'extrait; en outre, I'obtention de la biomasse en grande quantité est plus difficile. Similarly, an extraction of the biomass of Acetobacter pasteurianus makes it possible to obtain ceramides. However, the composition of the lipid extract is less fabulous, since the percentage of ceramides is lower, there is a greater amount of free amines in the extract; moreover, obtaining biomass in large quantities is more difficult.

Certaines levures (Candida utilis) peuvent également être utilisées. Les conditions de fermentation (milieu riche en sucres, mélasse) sont pourtant moins économiquement valables.Certain yeasts (Candida utilis) can also be used. The fermentation conditions (medium rich in sugars, molasses) are however less economically valid.

II est évident que la sélection de la souche et les conditions de fermentation ont une influence sur le rendement et la composition des lipides extraits par ce procédé. L'avantage de notre découverte est entre autre que les souches d'Aspergillus niger, d'Aspergillus orizae et d'Acetobacter sont fermentées à grande échelle industrielle et que l'accès à la biomasse (déchet industriel) est d'autant plus facile et économique. It is obvious that the selection of the strain and the fermentation conditions have an influence on the yield and the composition of the lipids extracted by this process. The advantage of our discovery is, among other things, that the strains of Aspergillus niger, Aspergillus orizae and Acetobacter are fermented on a large industrial scale and that access to biomass (industrial waste) is all the easier and economic.

Les extraits lipidiques obtenus par ces procédés et à partir des microorganismes mentionnés ci-dessus peuvent être utilisés dans les applications cosmétiques les plus diverses: pour tous les soins de la peau, pour l'hydratation et l'effet de lissage, pour le regraissage après aggression chimique, pour la réparation de la barrière cutanée, pour l'effet émollient et adoucissant. Les extraits enrichis en particulier après saponification peuvent être utilisés également dans des rouge-à-lèvres, dans les fonds de teint et des produits de maquillage. Grâce à la présence des stérols à côté des céramides, on obtient des effets antirougeurs et anti-irritants, cicatrisants et réparateurs, également utiles dans le traitement du cuir chevelu et de la peau acnéique. The lipid extracts obtained by these processes and from the microorganisms mentioned above can be used in the most diverse cosmetic applications: for all skin care, for hydration and smoothing effect, for regreasing after chemical aggression, for repairing the skin barrier, for the emollient and softening effect. The enriched extracts, in particular after saponification, can also be used in lipsticks, in foundations and in make-up products. Thanks to the presence of sterols next to the ceramides, anti-redness and anti-irritant, healing and repairing effects are obtained, also useful in the treatment of scalp and acne skin.

Les extraits lipidiques, objet du présent brevet, peuvent être utilisés dans toute forme galénique employée en cosmétique: émulsions H/E et E/H, laits, lotions, gels, pommades, huiles corporelles, lotions capillaires, shampooings, savons, sticks et crayons, sprays, sans que cette liste soit limitative.The lipid extracts which are the subject of this patent can be used in any galenical form used in cosmetics: O / W and W / O emulsions, milks, lotions, gels, ointments, body oils, hair lotions, shampoos, soaps, sticks and pencils , sprays, without this list being exhaustive.

II est possible d'incorporer les extraits lipidiques décrits dans des vecteurs cosmétiques comme les liposomes, les chylomicrons, les macro-, microet nanoparticules ainsi que les macro-, micro- et nanocapsules, de les absorber sur des polymères organiques poudreux, les talcs, bentonites et autres supports minéraux. It is possible to incorporate the lipid extracts described in cosmetic vectors such as liposomes, chylomicrons, macro-, micro and nanoparticles as well as macro-, micro- and nanocapsules, to absorb them on powdery organic polymers, talcs, bentonites and other mineral supports.

La concentration d'utilisation de ces extraits dépend de leur composition et de la quantité de céramides qu'ils renferment. Pour un effet cosmétique appréciable il est recommandé d'utiliser l'extrait entre 0.01 et 50%, préférentiellement entre 0.1 et 10%, voire 0.5 et 3%.The concentration of use of these extracts depends on their composition and the amount of ceramides they contain. For an appreciable cosmetic effect it is recommended to use the extract between 0.01 and 50%, preferably between 0.1 and 10%, even 0.5 and 3%.

Les extraits lipidiques peuvent être combinés dans les compositions cosmétiques avec tout autre ingrédient habituellement utilisé en cosmétique: lipides d'extraction eVou de synthèse, polymères gélifiants et viscosants, tensioactifs et émulsifiants, principes actifs hydro- ou liposolubles, extraits de plantes, extraits tissulaires, extraits marins. Lipid extracts can be combined in cosmetic compositions with any other ingredient usually used in cosmetics: synthetic eVou extraction lipids, gelling and viscous polymers, surfactants and emulsifiers, water- or liposoluble active principles, plant extracts, tissue extracts, marine extracts.

Claims (17)

REVENDICATIONS 1) Compositions cosmétiques contenant des lipides complexes extraits1) Cosmetic compositions containing complex lipids extracted à partir de la biomasse de microorganismes (levures, champignons, from the biomass of microorganisms (yeasts, fungi, bactéries). bacteria). 2) Compositions cosmétiques selon la revendication 1 caractérisées2) Cosmetic compositions according to claim 1 characterized en ce que les lipides contiennent des sphingolipides et/ou des in that the lipids contain sphingolipids and / or céramides. ceramides. 3) Compositions cosmétiques selon les revendications 1 et 23) Cosmetic compositions according to claims 1 and 2 caractérisées en ce que les lipides sont extraits à partir de la characterized in that the lipids are extracted from the biomasse des champignons de la famille des Aspergillus spp biomass of fungi from the Aspergillus spp. family 4) Compositions cosmétiques selon les revendications 1 et 24) Cosmetic compositions according to claims 1 and 2 caractérisées en ce que les lipides sont extraits à partir de la characterized in that the lipids are extracted from the biomasse des bactéries de la famille de Flavobacterium spp. biomass of bacteria of the family of Flavobacterium spp. 5) Compositions cosmétiques selon les revendications 1 et 25) Cosmetic compositions according to claims 1 and 2 caractérisées en ce que les lipides sont extraits à partir de la characterized in that the lipids are extracted from the biomasse des bactéries de la famille de Acetobacter spp.  biomass of bacteria of the family Acetobacter spp. 6) Compositions cosmétiques selon les revendications 1 et 26) Cosmetic compositions according to claims 1 and 2 caractérisées en ce que les lipides sont extraits à partir de la characterized in that the lipids are extracted from the biomasse des levures de la famille de Candida spp. yeast biomass of the Candida spp. 7) Compositions cosmétiques selon les revendications 1 et 27) Cosmetic compositions according to claims 1 and 2 caractérisées en ce que les lipides sont extraits à partir de la characterized in that the lipids are extracted from the biomasse d'Aspergillus orizae Aspergillus orizae biomass 8) Compositions cosmétiques selon les revendications 1 et 28) Cosmetic compositions according to claims 1 and 2 caractérisées en ce que les lipides sont extraits à partir de la characterized in that the lipids are extracted from the biomasse de Flavobacterium devorans biomass of Flavobacterium devorans 9) Compositions cosmétiques selon les revendications 1 et 29) Cosmetic compositions according to claims 1 and 2 caractérisées en ce que les lipides sont extraits à partir de la characterized in that the lipids are extracted from the biomasse d'Acetobacter pastorianus biomass of Acetobacter pastorianus 10) Compositions cosmétiques selon les revendications 1 et 210) Cosmetic compositions according to claims 1 and 2 caractérisées en ce que les lipides sont extraits à partir de la characterized in that the lipids are extracted from the biomasse de Candida utilis Candida biomass used 11) Compositions cosmétiques selon les revendications 1 à 1011) Cosmetic compositions according to claims 1 to 10 caractérisées en ce que la biomasse est obtenue par une étape de characterized in that the biomass is obtained by a step of fermentation industrielle des souches citées, suivie d'une séparation industrial fermentation of the strains mentioned, followed by separation par filtration ou centrifugation et d'un séchage. by filtration or centrifugation and drying. 12) Compositions cosmétiques selon l'une quelconque des12) Cosmetic compositions according to any one of revendications 1 à 11 caractérisées en ce que l'extrait lipidique est Claims 1 to 11, characterized in that the lipid extract is obtenu par extraction aux solvants organiques, suivie d'une obtained by extraction with organic solvents, followed by éventuelle décoloration, d'une purification et d'une concentration par possible discoloration, purification and concentration by saponification et séparation. saponification and separation. 13) Compositions cosmétiques selon l'une quelconque des13) Cosmetic compositions according to any one of revendications I à 12 caractérisées en ce que l'extrait lipidique Claims I to 12, characterized in that the lipid extract contient entre 5 et 80% de sphingolipides et/ou céramides, entre contains between 5 and 80% of sphingolipids and / or ceramides, between 0 et 50% de stérols et entre 0 et 99% de lipides saponifiables. 0 and 50% sterols and between 0 and 99% saponifiable lipids. 14) Compositions cosmétiques selon l'une quelconque des14) Cosmetic compositions according to any one of revendications 1 à 13 caractérisées en ce que l'extrait lipidique est Claims 1 to 13, characterized in that the lipid extract is utilisé à des concentrations situées entre 0.01 et 50%, used at concentrations between 0.01 and 50%, préférentiellement entre 0.1 et 10%, encore plus préférentiellement preferably between 0.1 and 10%, even more preferably entre 0.5 et 3%.  between 0.5 and 3%. 15) Compositions cosmétiques selon l'une quelconque des15) Cosmetic compositions according to any one of revendications 1 à 14 caractérisées en ce que l'extrait lipidique Claims 1 to 14, characterized in that the lipid extract est utilisé dans toute forme galénique employée en cosmétique: is used in any dosage form used in cosmetics: émulsions H/E et E/H, laits, lotions, gels, pommades, huiles O / W and W / O emulsions, milks, lotions, gels, ointments, oils corporelles, lotions capillaires, shampooings, savons, sticks et body, hair lotions, shampoos, soaps, sticks and crayons, sprays. pencils, sprays. 16) Compositions cosmétiques selon l'une quelconque des16) Cosmetic compositions according to any one of revendications 1 à 13 caractérisées en ce que l'extrait lipidique Claims 1 to 13, characterized in that the lipid extract est incorporé dans des vecteurs cosmétiques comme les is incorporated into cosmetic carriers such as liposomes, les chylomicrons, les macro-, micro- et nanoparticules liposomes, chylomicrons, macro-, micro- and nanoparticles ainsi que les macro-, micro- et nanocapsules, ou absorbé sur des as well as macro-, micro- and nanocapsules, or absorbed on polymères organiques poudreux, les talcs, bentonites et autres powdery organic polymers, talcs, bentonites and others supports minéraux. mineral supports. 17) Compositions cosmétiques selon l'une quelconque des17) Cosmetic compositions according to any one of revendications 1 à 14 caractérisées en ce que I' extrait lipidique Claims 1 to 14, characterized in that the lipid extract est combiné dans ces compositions cosmétiques avec un ou is combined in these cosmetic compositions with one or plusieurs autres ingrédients habituellement utilisés en cosmétique: several other ingredients usually used in cosmetics: lipides d'extraction et/ou de synthèse, polymères gélifiants et extraction and / or synthetic lipids, gelling polymers and viscosants, tensioactifs et émulsifiants, principes actifs hydro- ou viscosants, surfactants and emulsifiers, hydro- or active ingredients liposolubles, extraits de plantes, extraits tissulaires, extraits marins.  fat-soluble, plant extracts, tissue extracts, marine extracts.
FR9301074A 1993-01-29 1993-01-29 Use of certain strains of microorganisms as a new source of ceramides and sphingolipids for cosmetic use. Expired - Fee Related FR2700953B1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2728792A1 (en) * 1995-01-04 1996-07-05 Oreal COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING AT LEAST ONE CERAMID 6
EP0730032A2 (en) * 1995-02-28 1996-09-04 Yakurigaku Chuo Kenkyusho Process for preparing sphingomyelin and ceramide from erythrocyte as a starting material and a curing agent or cosmetic formulated with ceramide
JP2008056695A (en) * 2007-11-02 2008-03-13 Mitsukan Group Honsha:Kk Composition for ameliorating skin function, containing ceramide from acetobacter

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JPS61275208A (en) * 1985-05-30 1986-12-05 Agency Of Ind Science & Technol Cosmetic
EP0263684A2 (en) * 1986-10-06 1988-04-13 The University of Calgary Lipid based radiation protection
JPS63234513A (en) * 1987-03-24 1988-09-29 Canon Inc Deposition film formation
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Cited By (6)

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FR2728792A1 (en) * 1995-01-04 1996-07-05 Oreal COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING AT LEAST ONE CERAMID 6
EP0720847A1 (en) * 1995-01-04 1996-07-10 L'oreal Cosmetic or dermatological composition containing at least one ceramide 6
EP0730032A2 (en) * 1995-02-28 1996-09-04 Yakurigaku Chuo Kenkyusho Process for preparing sphingomyelin and ceramide from erythrocyte as a starting material and a curing agent or cosmetic formulated with ceramide
EP0730032A3 (en) * 1995-02-28 1998-03-04 Yakurigaku Chuo Kenkyusho Process for preparing sphingomyelin and ceramide from erythrocyte as a starting material and a curing agent or cosmetic formulated with ceramide
US5912152A (en) * 1995-02-28 1999-06-15 Yakurigaku Chuo Kenkyusho Process for preparing sphingomyelin and ceramide from erythrocyte as a starting material and a curing agent or cosmetic formulated with ceramide
JP2008056695A (en) * 2007-11-02 2008-03-13 Mitsukan Group Honsha:Kk Composition for ameliorating skin function, containing ceramide from acetobacter

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