EP0755242A1 - Use of galactosylglycerides and of naturally occurring extracts containing such products in cosmetics, pharmaceutics and particularly dermatology - Google Patents

Use of galactosylglycerides and of naturally occurring extracts containing such products in cosmetics, pharmaceutics and particularly dermatology

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Publication number
EP0755242A1
EP0755242A1 EP96904147A EP96904147A EP0755242A1 EP 0755242 A1 EP0755242 A1 EP 0755242A1 EP 96904147 A EP96904147 A EP 96904147A EP 96904147 A EP96904147 A EP 96904147A EP 0755242 A1 EP0755242 A1 EP 0755242A1
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EP
European Patent Office
Prior art keywords
formula
acyl group
galactopyranosyl
use according
group
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.)
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Application number
EP96904147A
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German (de)
French (fr)
Inventor
Jocelyne Franchi
Françoise PELLICIER
Valérie KRZYCH
Gérard Redziniak
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.)
Parfums Christian Dior SA
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Parfums Christian Dior SA
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Publication date
Application filed by Parfums Christian Dior SA filed Critical Parfums Christian Dior SA
Publication of EP0755242A1 publication Critical patent/EP0755242A1/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention relates to a new use of galactosylglycerides, very particularly digalactosyldiglycerides, and extracts of natural origin containing these products, in the cosmetic, pharmaceutical and in particular dermatological fields.
  • the invention relates to a new use of galactosylglycerides as agents intended to intensify the production of extracellular fibronectin.
  • This new use finds its application in particular in cosmetics or dermatology, in particular for the preparation of compositions intended for firming the skin, accelerating healing, preventing or treating wrinkles, and, in general, preventing or treat the effects of skin aging.
  • fibronectin exists in two forms: a soluble form found in plasma and other body fluids, and an insoluble matrix form distributed in loose connective tissue and various basement membranes. Fibronectins are high molecular weight glycoproteins (450,000) formed from two similar subunits. DNA séquen ⁇ age c studies have shown that plasma fibronectin and cell came from a single gene by alternative splicing of the first transcribed.
  • the carbohydrate part of the molecule varies according to the fibronectins - the constituent oses are sialic acid, hexoses, hexosamines - the oligossacharidic chains are asymmetrically distributed on the molecule with highly glycosylated domains and others devoid of carbohydrates.
  • Fibronectins have common immunological characteristics vis-à-vis polyclonal antibodies. In addition, they interact with collagens, fibrin, proteoglycans, certain elements of the cytoskeleton, bacteria, cell surfaces (fibronectin and its role in cell-matrix interactions. J. LABAT-Robert, review biology society 1986, 180, p. 142-150).
  • Fibronectin has a complex molecular structure consisting of multiple specific binding sites and it appears that the complex biological phenomena in which "fibronectins" are involved are related to their structures (fibronectins: multifunctional modular glycoproteins, Richard O hynes and Kenneth M. Yamada - The Journal of Cell Biology 1982, 95: 369-377) for example, morphology, cytoskeleton organization, oncogenic transformation, phagocytosis. In the central area of the "fibronectin” molecule is the binding site with cell surfaces.
  • fibronectin As the prototype of the protein responsible for the adhesion of cells to their substrate, but the expression of fibronectin and its receptors regulate several cellular properties: polarity, capacity to migrate, the state of differentiation (fibronectin and its receptors E.Ruoslahti, Ann. Rev. Biochem. 1988, 57: 375-413).
  • the fibronectin subunits have sites of interactions with receptors of the cell membrane, the integrins which recognize the RGD peptide.
  • the integrins which recognize the RGD peptide.
  • galactolipids are among the essential constituents of living things, both animals and plants. In higher beings, they are present throughout the body, mainly as constituents of cell membranes. In plants, they are in particular localized in the chloroplastic envelope. Many publications are devoted to them, such as the following publications:
  • the galactolipids include in particular the galactosylglycerides.
  • the latter are well known, and can be extracted from plants, for example from cereals.
  • DGDG digalactosyldiglycerides
  • JP-A2-0503750 which describes the use of the same products to improve the quality of products made from wheat flour
  • the invention relates to the use of galactosylglycerides, very particularly digalactosyldiglycerides, and in particular plant extracts containing these products, for all cosmetic or pharmaceutical, in particular dermatological, applications where it is sought to obtain a densification of the network. extracellular fibronectin.
  • the main object of the present invention is therefore to solve the technical problem of providing a cosmetic or pharmaceutical composition, in particular a dermatological composition, having excellent efficacy in preventing or treating the effects of skin aging, in particular the appearance of wrinkles. and on skin firming.
  • the invention relates to the use of at least one galactosyl-diglyceride or of an extract of natural origin containing it as a cosmetic agent promoting the formation of extracellular fibronectin by fibroblasts, thus making it possible to improve cutaneous healing, to strengthen the biomechanical properties of the dermis or connective tissues, to improve the appearance of the surface of the skin, and making it possible, in particular, to prevent or treat the effects of skin aging, such as wrinkles or sagging tissues skin support.
  • the invention therefore relates, according to one of its essential characteristics, to the use of at least one galactosylglyceride or of an original extract natural containing it as a cosmetic agent making it possible to improve skin healing, to strengthen the biomechanical properties of the dermis, to improve the appearance of the skin surface, or to prevent or treat the effects of skin aging, such as wrinkles or sagging skin support tissue.
  • improvement of the biomechanical properties of the dermis is meant any improvement of biological origin of the structural quality of the dermis.
  • the intensification of the extracellular fibronectin network makes it possible to improve the adhesion of cells to intercellular macromolecules, such as collagen.
  • the use according to the invention more particularly makes it possible to obtain skin firming, prevention of the appearance of wrinkles or attenuation of their depth.
  • the above-mentioned extract of natural origin is a plant extract, in particular a cereal extract such as wheat or oats, or an extract of leaves or nuts of Ginkgo Biloba.
  • the galactosylglycerides which are useful according to the invention are very particularly the monogalactosylmonoglycerides (MGMG), the monogalactosyldiglycerides (MGDG), the digalactosylmonoglyc ⁇ rides (DGMG) and the digalactosyldiglycerides (DGDG).
  • MGMG monogalactosylmonoglycerides
  • MGDG monogalactosyldiglycerides
  • DGMG digalactosylmonoglyc ⁇ rides
  • DGDG digalactosyldiglycerides
  • the mono- or digalactosyldiglycerides will be chosen.
  • the galactosylglyceride will correspond to formula (I):
  • Gai represents a galactopyranosyl group, preferably beta-D-galactopyranosyl,
  • - Ri represents an acyl group of formula
  • R represents an aliphatic hydrocarbon chain, saturated or not, preferably linear, and comprising from 9 to 29 carbon atoms
  • - R2 represents a hydrogen atom or an acyl group, identical or different from R ⁇ , of formula
  • a chain consisting of a chain of several sugars, preferably two or three sugars, chosen from the group consisting of alpha- and beta-D- galactopyranosyle, alpha-D-glucopyranosyle, alpha- D- and alpha-L- manopyranosyle.
  • the galactosyl ⁇ glycerides are chosen from mono- and digalactosyldiglycerides (respectively MGDG and DGDG) of formula (I) above, in which
  • Rj and R2 correspond to the definition given above, except that R2 necessarily represents an acyl group
  • - A represents a single bond or an alpha- or beta-D- galactopyranosyl group.
  • the galactosyldiglyceride above is chosen from digalactosyldiglycerides (DGDG), that is to say from products in which A represents an alpha- or beta-D-galactopyranosyl group.
  • DGDG digalactosyldiglycerides
  • galactosylglycerides will be chosen for each of the preceding variants for which: - R ⁇ represents an acyl group of formula
  • R represents a linear aliphatic hydrocarbon chain containing 15, 17 or 19 carbon atoms, saturated or comprising from 1 to 5 double bonds, in position 7, 10 and / or 13 for an acyl group of 16 carbon atoms, in position 9, 12 and / or 15 for an acyl group of 18 carbon atoms, and in positions 5, 8, 10, 14 and / or 17 for an acyl group of 20 carbon atoms.
  • - R2 represents a hydrogen atom or an acyl group, identical or different from R ⁇ , of formula
  • the invention also relates to a cosmetic treatment process intended in particular to reinforce the biomechanical properties of the dermis by an intensification of the formation of extracellular fibronectin by fibroblasts, to obtain a skin tightening or the improvement of the surface of the skin or to prevent or treat the effects of skin aging such as the appearance of wrinkles, consisting in applying locally to the areas of the skin to be treated a composition containing at least one galactosylglyceride or a plant extract containing it.
  • the galactosylglyceride will advantageously be chosen from the galactosylglycerides of formula (I) described above, the preferred products constituting the same subclasses as those defined above.
  • the extracts of natural origin containing the galactosylglycerides which can be used for the implementation of the invention, can be obtained by extraction methods well known to those skilled in the art.
  • the extraction solvent used will preferably be a polar solvent, such as an alcohol, an ether or a halogenated hydrocarbon. We will choose for example methanol, ethanol, isopropanol, ethyl ether or chloroform.
  • the same galactosylglycerides and very particularly the digalactosyldiglycerides, and the natural extracts containing them can be used as active agent of pharmaceutical compositions, in particular dermatological compositions, intended to intensify the synthesis of extracellular fibronectin.
  • the invention relates to the use, as active principle, of at least one galactosylglyceride or of an extract of natural origin containing it, for the preparation of a pharmaceutical composition, in particular dermatological, intended to prevent or treat various pathologies accompanied by a deficiency in the intensity of the extracellular fibronectin network in the connective tissues, in particular in the dermis, in improving the biomechanical properties of the skin, in preventing or treating the effects of aging, in particular of skin aging, to promote healing or to obtain skin firming.
  • the invention relates very particularly to the use, as active principle, of at least one galactosylglyceride, as described above, in particular a digalactosyldiglyceride, for the preparation of compositions for the abovementioned indications.
  • the galactosylglycerides are advantageously chosen for this application from family I defined above and the sub-families of preferred products are the same as those defined above.
  • the abovementioned active principle is an extract of natural, animal or plant origin, as previously defined.
  • it will be a plant extract, in particular a cereal extract, such as wheat or oats, or an extract of Gingko Biloba leaves or nuts.
  • compositions according to the invention are therefore very particularly intended for firming the skin, accelerating or improving the healing process, preventing the appearance of wrinkles or their treatment, and a generally for the prevention or treatment of the effects of skin aging.
  • the compositions of the invention can therefore, in particular, be advantageously used to reduce the depth of wrinkles, in particular those of the face and the neck.
  • the galactosylglyceride concentrations of between 0.001 and 10% by weight relative to the total weight of the composition containing it will preferably be used. This concentration will preferably be between 0.01 and 5% by weight relative to the total weight of said composition.
  • Plant extracts containing at least one galactosylglyceride in particular cereal extracts such as wheat or oats, will be used in a particularly advantageous manner.
  • Such products exist commercially.
  • commercial products mention may be made of commercial products containing DGDG and MGDG available from SIGMA Chemical Company (Saint-Louis, Mo, USA).
  • the administration of galactosylglycerides is carried out according to conventional methods, allowing stimulation of the production of extracellular fibronectin.
  • the simplest route of administration is the topical route, in particular when one seeks to restore or reinforce the biomechanical properties of the cutaneous support tissues to firm the skin, or to prevent or attenuate the appearance of wrinkles, especially those of the face or neck.
  • compositions according to the invention will be formulated, in accordance with techniques well known to those skilled in the art, suitably for topical administration, for example in the form of a cream, milk, lotion, gelled or not. , or ointment.
  • the galactosylglyceride or the extract containing it is incorporated into an excipient, vehicle or carrier cosmetically or pharmaceutically, in particular dermatologically acceptable.
  • Such supports are well known to those skilled in the art and also result from examples of cosmetic compositions or pharmaceutical compositions, in particular dermatological compositions described below which are general in scope.
  • FIGS. 1 to 4 which are an integral part of Example 1, are copies of photographs obtained during observation under a fluorescent microscope of the extracellular network of fibronectin secreted respectively by:
  • the immunolocalization of fibronectin is based on the general principle of the specific binding of an antibody to its antigen.
  • the technique is performed by indirect immunostaining. First, an anti-fibronectin antibody prepared in rabbits is brought into contact with the cell layer.
  • the complex formed by the binding of the specific antibody to its antigen is revealed by the addition of a globulin directed against rabbit Ig G coupled to a fluorochrome, here, R phycoerythrin.
  • the antibodies used are:
  • Goat antibody F (ab ') 2 rabbit anti-immunoglobulin (G + L) labeled with phycoerythrin (TAGO Ref. 4920).
  • the cells used are fibroblasts from mammary or abdominal surgical plasties from healthy adult donors.
  • the cells are inoculated on glass slides, and 24 h after inoculation, the medium is renewed in the presence or not of DGDG.
  • the initial culture medium is MEM + 10% fetal calf serum (SVF).
  • the medium consists of MEM medium + 2.5% fetal calf serum.
  • the DGDG is dissolved in DMSO and used on the cultures at the final concentration of 750 ⁇ g / ml. Cultivation operations take place as follows:
  • the cells After rinsing the coverslips with PBS buffer, the cells are fixed for 20 min with paraformaldehyde (3.7% in PBS) at 4 ° C.
  • the anti-fibronectin antibody (diluted to 1 / 250th in PAB) is brought into contact with the cells. for 60 min at 4 * C.
  • This operation is followed by passing through a buffer solution (PAB) and then 2 baths of 15 min in the same buffer.
  • PAB buffer solution
  • the second part of the reaction is carried out by adding the fluorescent conjugate (diluted to 1 / 500th in PAB) for 45 min at room temperature. The cells are then again rinsed with PBS.
  • Each strip is then dried and mounted on a slide (mounting medium: 33% glycerol in PBS).
  • the orientation of the fibers is clear.
  • the condensation of the fibers present in certain cells contrasts with the presence of fine fibers interspersed and isolated.
  • the fibers are associated with each other, intertwined. They mark a kind of swirls, the outline of the cells is not discernible
  • the fibers appear to be nested in a net with relatively tight stitches, of the "lace” or "skein” type.
  • DGDG causes a considerable increase in the formation of extracellular fibronectin by fibroblasts, regardless of the age of the subjects.
  • Example 2 Demonstration of the activity of digalactosyldiglyceride increasing the adhesion capacity of fibroblasts.
  • the purpose of this experiment is to verify the stimulation of the adhesion capacity of normal human fibroblasts treated with DGDG. For this, we will observe the speed of adhesion to a plastic support of these cells in culture.
  • a culture of normal human fibroblasts is obtained in a 75 ml flask, obtained as indicated above in Example 1. These cells are cultured in a conventional manner in MEM medium supplemented with 10% fetal calf serum, to which is added DGDG (SIGMA) at the concentration of 750 ⁇ g / ml. The culture is carried out for one week, with two replenishments of the culture medium in the week, always with the same concentration of DGDG.
  • SIGMA DGDG
  • the cells are peeled off, leaving a 2 mM solution of EDTA (ethylenediaminetetraacetic acid) to act for 30 minutes.
  • EDTA ethylenediaminetetraacetic acid
  • the cells After centrifugation, the cells are resuspended in a conventional culture medium (MEM supplemented with 10% fetal calf serum).
  • MEM fetal calf serum
  • a stable dispersion is prepared containing 1% by weight of DGDG and 2% of collagen.
  • the dispersion is gelled by adding 0.2% by weight of Carbopol 940 and a preservative is added.
  • Example 4 Product with Anti-Wrinkle Effect A stable emulsion is prepared containing:
  • 80% water + classic preservatives as follows: The DGDG is dissolved in the oil and the whole is brought to 75 ° C. The water with the preservatives is heated separately to 75 # C. Part of the water is then incorporated into the fatty phase, then the whole is introduced into the remaining part of the aqueous phase, at 75 ° C. with magnetic stirring. The emulsion is brought to 80 ° C. still under magnetic stirring, then homogenized for 5 min at 11,000 rpm, using Ultra - Turax. It is then immersed in an ice bath in order to obtain rapid cooling, freezing the structure.

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Abstract

Use of at least one galactosylglyceride, more particularly digalactosyldiglycerides, or a naturally occurring extract containing such products, as an active ingredient, as a cosmetic agent or a medicine stimulating the formation of extracellular fibronectin by amplifying its network and particularly for preparing a composition for preventing or alleviating the effects of skin ageing. The use of the above composition as an anti-wrinkle, firming or wound healing product is particularly described.

Description

Utilisation des galactosvlelvcérides et des extraits d'origine naturelle contenant ces produits, dans les domaines cosmétique, pharmaceutique et notamment dermatologique.Use of galactosvlelvcérides and extracts of natural origin containing these products, in the cosmetic, pharmaceutical and in particular dermatological fields.
La présente invention concerne une nouvelle utilisation des galactosylglycérides, tout particulièrement des digalactosyldiglycérides, et des extraits d'origine naturelle contenant ces produits, dans les domaines cosmétique, pharmaceutique et notamment dermatologique.The present invention relates to a new use of galactosylglycerides, very particularly digalactosyldiglycerides, and extracts of natural origin containing these products, in the cosmetic, pharmaceutical and in particular dermatological fields.
Plus précisément, l'invention concerne une nouvelle utilisation des galactosylglycérides comme agents destinés à intensifier la production de la fibronectine extracellulaire. Cette nouvelle utilisation trouve son application en particulier en cosmétique ou en dermatologie, notamment pour la préparation de compositions destinées au raffermissement de la peau, à accélérer la cicatrisation, à prévenir ou traiter les rides, et, d'une façon générale, à prévenir ou traiter les effets du vieillissement cutané.More specifically, the invention relates to a new use of galactosylglycerides as agents intended to intensify the production of extracellular fibronectin. This new use finds its application in particular in cosmetics or dermatology, in particular for the preparation of compositions intended for firming the skin, accelerating healing, preventing or treating wrinkles, and, in general, preventing or treat the effects of skin aging.
In vivo, la fibronectine existe sous deux formes : une forme soluble présente dans le plasma et d'autres liquides biologiques, et une forme insoluble matricielle distribuée dans les tissus conjonctife lâches et diverses membranes basales. Les fibronectines sont des glycoprotéincs de haut poids moléculaire (450000) formées de deux sous-unités similaires. Des études de séquenςage d'ADNc ont prouvé que fibronectines plasmatique et cellulaire provenaient d'un seul gène par épissage alternatif du premier transcrit.In vivo, fibronectin exists in two forms: a soluble form found in plasma and other body fluids, and an insoluble matrix form distributed in loose connective tissue and various basement membranes. Fibronectins are high molecular weight glycoproteins (450,000) formed from two similar subunits. DNA séquenςage c studies have shown that plasma fibronectin and cell came from a single gene by alternative splicing of the first transcribed.
La partie glucidique de la molécule varie selon les fibronectines - les oses constitutifs sont l'acide sialique, des hexoses, des hexosamines - les chaînes oligossacharidiques sont distribuées asymέtriquement sur la molécule avec des domaines hautement glycosylés et d'autres dépourvus de glucides. Les fibronectines présentent des caractères immunologiques communs vis-à-vis des anticorps polyclonaux. Par ailleurs, elles interagissent avec les collagènes, la fibrine, des protéoglycanes, certains éléments du cytosquelette, des bactéries, les surfaces cellulaires (la fibronectine et son rôle dans les interactions cellules- matrices. J.LABAT-Robert, compte rendu société de biologie 1986, 180, p. 142- 150).The carbohydrate part of the molecule varies according to the fibronectins - the constituent oses are sialic acid, hexoses, hexosamines - the oligossacharidic chains are asymmetrically distributed on the molecule with highly glycosylated domains and others devoid of carbohydrates. Fibronectins have common immunological characteristics vis-à-vis polyclonal antibodies. In addition, they interact with collagens, fibrin, proteoglycans, certain elements of the cytoskeleton, bacteria, cell surfaces (fibronectin and its role in cell-matrix interactions. J. LABAT-Robert, review biology society 1986, 180, p. 142-150).
La fibronectine possède une structure moléculaire complexe consistant en de multiples sites de liaisons spécifiques et il semble que les phénomènes biologiques complexes dans lesquels sont impliquées "les fibronectines" sont liés à leurs structures (fibronectins : multifunctional modular glycoproteins, Richard O hynes and Kenneth M.Yamada - The Journal of Cell Biology 1982, 95 : 369- 377) par exemple, la morphologie, l'organisation du cytosquelette, la transformation oncogénique, la phagocytose. Dans la zone centrale de la molécule "fibronectine" se trouve le site de liaison avec les surfaces cellulaires. Des recherches intensives in vitro comme in vivo ont désigné la fibronectine comme étant le prototype de la protéine responsable de l'adhésion des cellules à leur substrat mais l'expression de la fibronectine et de ses récepteurs régulent plusieurs propriétés cellulaires : la polarité, la capacité à migrer, l'état de différenciation (fibronectin and its receptors E.Ruoslahti, Ann. Rev. Biochem. 1988, 57 : 375-413).Fibronectin has a complex molecular structure consisting of multiple specific binding sites and it appears that the complex biological phenomena in which "fibronectins" are involved are related to their structures (fibronectins: multifunctional modular glycoproteins, Richard O hynes and Kenneth M. Yamada - The Journal of Cell Biology 1982, 95: 369-377) for example, morphology, cytoskeleton organization, oncogenic transformation, phagocytosis. In the central area of the "fibronectin" molecule is the binding site with cell surfaces. Intensive research in vitro and in vivo has designated fibronectin as the prototype of the protein responsible for the adhesion of cells to their substrate, but the expression of fibronectin and its receptors regulate several cellular properties: polarity, capacity to migrate, the state of differentiation (fibronectin and its receptors E.Ruoslahti, Ann. Rev. Biochem. 1988, 57: 375-413).
On sait que la capacité de fixation cellulaire peut être attribuée à un tripeptide : le L-arginyl-glycyl-L-aspartyl (RGD) dont chacun des aminoacides contribue à la liaison (New Perspectives in Cell Adhésion RGD and integrins, E.Ruoslahti ; M.Pierschbacher, Science 1987, Vol.238, p.491-497).We know that the cell binding capacity can be attributed to a tripeptide: L-arginyl-glycyl-L-aspartyl (RGD), each of which amino acids contributes to binding (New Perspectives in Cell Adhesion RGD and integrins, E.Ruoslahti; M.Pierschbacher, Science 1987, Vol. 238, p.491-497).
Les sous-unités de la fibronectine possèdent des sites d'interactions avec des récepteurs de la membrane cellulaire, les intégrines qui reconnaissent le peptide RGD. (Integrins in human cells and tumors, I.Virtanen, M.Korhonen, A.L.Kariniemi, V.E.Gould, L.Laitinen, J.Ylânne, Cell Differentiation and Development, 1990, 32, 215-228).The fibronectin subunits have sites of interactions with receptors of the cell membrane, the integrins which recognize the RGD peptide. (Integrins in human cells and tumors, I. Virtanen, M.Korhonen, A.L. Kariniemi, V.E.Gould, L.Laitinen, J.Ylânne, Cell Differentiation and Development, 1990, 32, 215-228).
Toutes les cellules dans les tissus sont en contact avec une matrice extracellulaire. Celle-ci est constituée de trois protéines majeures sous forme de fibres : le collagène, l'élastine et les glycoprotéines de structures comme la fibronectine qui sont imbriquées dans un gel hydraté de glycosaminoglycanes. Toutes ces macromolécules sont sécrétées localement par les cellules. Les macromolécules de la matrice extracellulaire ont des effets remarquables sur le comportement des cellules influençant leur forme, mouvement, métabolisme et différenciation.All cells in the tissue are in contact with an extracellular matrix. This consists of three major proteins in the form of fibers: collagen, elastin and glycoproteins of structures like fibronectin which are embedded in a hydrated gel of glycosaminoglycans. All these macromolecules are secreted locally by the cells. The macromolecules of the extracellular matrix have remarkable effects on the behavior of cells, influencing their shape, movement, metabolism and differentiation.
Ces interactions cellules-matrice peuvent être modifiées par des altérations de la structure et des fonctions de ces molécules au cours du vieillisse¬ ment et de divers états pathologiques. Elles peuvent être perturbées par la présence de fragments possédant une activité protéolytique : c'est le cas de la fibronectine qui est scindée en plusieurs fragments au cours de processus inflammatoires. Ces fragments possèdent donc une activité protéolytique propre absente de la molécule intacte (Potential proteolytic activity of fibronectin : fibronectin laminase and its substrate specificity, I.Emod, P.Lafaye, T.Planchenault, S.Lambert-Vidman, J.M.Imhoff and V.Keil-Dlouha, Biol. Chem. Hoppe-Seyler 1990, 371, 129-135). On sait que la composition de la matrice extracellulaire de tous les tissus et les organes change continuellement en fonction de l'âge. La composition d'un tissu dépend de la vitesse relative de synthèse de ses constituants suivie de leur dégradation. Les interactions cellules-matrice peuvent être d'une grande importance au cours du vieillissement des tissus conjonctifs et les glycoprotéines de structure jouent un rôle clef dans ces phénomènes. Au niveau de la peau, le vieillissement dermique correspond à une perte de cohésion entre fibroblastes et collagène. Au cours du vieillissement, les modifications dans l'architecture ne s'accompagnent pas de variations qualitative et/ou quantitative des collagènes I et m. Par contre, in vitro, la fibronectine fibrillaire extracellulaire se raréfie avec l'âge. (Vieillissement dermique - Etude en immunofluorescence des collagènes I et m et de la fibronectine M.TH.Pieraggi, MJulian, H.Bouissou, S.Stocker, JA.Grimaud - Ann. Pathol. 1984, 4 n^, 185-194).These cell-matrix interactions can be modified by alterations in the structure and functions of these molecules during aging and various pathological states. They can be disturbed by the presence of fragments with proteolytic activity: this is the case with fibronectin which is split into several fragments during inflammatory processes. These fragments therefore have their own proteolytic activity absent from the intact molecule (Potential proteolytic activity of fibronectin: fibronectin laminase and its substrate specificity, I.Emod, P.Lafaye, T.Planchenault, S.Lambert-Vidman, JMImhoff and V.Keil-Dlouha, Biol. Chem. Hoppe-Seyler 1990, 371, 129-135). We know that the composition of the extracellular matrix of all tissues and organs changes continuously with age. The composition of a tissue depends on the relative speed of synthesis of its constituents followed by their degradation. Cell-matrix interactions can be of great importance during the aging of connective tissues and structural glycoproteins play a key role in these phenomena. In the skin, dermal aging corresponds to a loss of cohesion between fibroblasts and collagen. During aging, the changes in architecture are not accompanied by qualitative and / or quantitative variations in the collagens I and m. On the other hand, in vitro, extracellular fibrillar fibronectin becomes scarce with age. (Dermal aging - Immunofluorescence study of collagens I and m and of fibronectin M.TH.Pieraggi, MJulian, H.Bouissou, S.Stocker, JA.Grimaud - Ann. Pathol. 1984, 4 n ^, 185-194) .
Bien que certains auteurs aient observé une augmentation de la biosynthèse de la fibronectine avec l'âge (Ladislas Robert, "Le vieillissement. De l'homme à la cellule", 1994, Belin, Paris, p.126), il ressort clairement de nombreuses autres publications, en particulier de celle de Bernard Djian ("Comblement des rides", Manuels de Pratiques de Médecine Esthétique, 1992, Ed. Arnette S.A., Paris, p. 4O-41), que la fibronectine extracellulaire se raréfie lors du vieillissement cutané. Or cette glycoprotéine, particulièrement abondante dans le derme, surtout chez les sujets jeunes, joue un rôle essentiel dans la cohésion des cellules entre elles et dans l'adhésivité entre les cellules et le collagène. D'où il ressort que la présence d'un réseau de fibronectine extracellulaire en bon état est bénéfique.Although some authors have observed an increase in the biosynthesis of fibronectin with age (Ladislas Robert, "Aging. From man to cell", 1994, Belin, Paris, p.126), it is clear from numerous other publications, in particular that of Bernard Djian ("Filling wrinkles", Manuals of Practices of Aesthetic Medicine, 1992, Ed. Arnette SA, Paris, p. 4O-41), that extracellular fibronectin becomes rare during aging skin. However, this glycoprotein, particularly abundant in the dermis, especially in young people, plays an essential role in the cohesion of cells between them and in the adhesiveness between cells and collagen. From which it appears that the presence of a network of extracellular fibronectin in good condition is beneficial.
Par ailleurs, les galactolipides comptent parmi les constituants essentiels des êtres vivants, aussi bien animaux que végétaux. Chez les êtres supérieurs, ils sont présents dans l'ensemble de l'organisme, principalement en tant que constituants des membranes cellulaires. Chez les plantes, ils sont en particulier localisés dans l'enveloppe chloroplastique. De très nombreuses publications leur sont consacrées, comme par exemple, les publications suivantes :In addition, galactolipids are among the essential constituents of living things, both animals and plants. In higher beings, they are present throughout the body, mainly as constituents of cell membranes. In plants, they are in particular localized in the chloroplastic envelope. Many publications are devoted to them, such as the following publications:
- "Comparative study of the immunological properties of galactosylipid and galactosylceramide included within natural membranes", DUPOUEY P. al., Immunochemistry (1976) , p. 289-294 - "Plant galactolipids" DOUCE R. et JOYARD J., dans "The biochemistry of plants", Stumpf P. K. (Editor), Académie Press, New York-USA (1980) volume 4, p. 321-362- "Comparative study of the immunological properties of galactosylipid and galactosylceramide included within natural membranes", DUPOUEY P. al., Immunochemistry (1976), p. 289-294 - "Plant galactolipids" DOUCE R. and JOYARD J., in "The biochemistry of plants", Stumpf PK (Editor), Académie Press, New York-USA (1980) volume 4, p. 321-362
- "Localization of galactolipid : galactolipid galactosyltransferase and acyltransferase in outer envelope membrane of spinach chloroplasts",- "Localization of galactolipid: galactolipid galactosyltransferase and acyltransferase in outer envelope membrane of spinach chloroplasts",
HEEMSKERK J. W.M., et al. Biochimica et biophysica acta, (1986) £ZZ (2) p.281-289HEEMSKERK J. W.M., et al. Biochimica et biophysica acta, (1986) £ ZZ (2) p.281-289
- "Iipids : structure and function", Stumpf P.K. (Editor), (1987) vol. 9, ISBN 0-12-675409.8, "The biochemistry of plants". Les galactolipides comprennent en particulier les galactosylglycérides.- "Iipids: structure and function", Stumpf P.K. (Editor), (1987) vol. 9, ISBN 0-12-675409.8, "The biochemistry of plants". The galactolipids include in particular the galactosylglycerides.
Ces derniers sont bien connus, et peuvent être extraits de plantes, par exemple de céréales.The latter are well known, and can be extracted from plants, for example from cereals.
Ainsi, l'article de J.A. Prieto, A. Ebri et C. Collar, "OptimizedThus, the article by J.A. Prieto, A. Ebri and C. Collar, "Optimized
Séparation of Nonpolar and Polar Lipid Classes from Wheat Flour by Solid-Phase Extraction" (J. Amer. Org. Chem. Soc., (1992) ≤9_, No.4, 387-391), décrit une technique de séparation par chromatographie des différents galactosylglycérides contenus dans la farine de blé.Separation of Nonpolar and Polar Lipid Classes from Wheat Flour by Solid-Phase Extraction "(J. Amer. Org. Chem. Soc., (1992) ≤9_, No.4, 387-391), describes a separation technique by chromatography different galactosylglycerides contained in wheat flour.
Par ailleurs, un autre article des mêmes auteurs "Composition and Distribution of Individuel Molecular Spccies of Major Glycolipids in Wheat Flour" (J. Amer. Org. Chem. Soc., (1992) £ , No. 10, 1019-1022), décrit la composition et la distribution des principaux glycolipides contenus dans la farine de blé.Furthermore, another article by the same authors "Composition and Distribution of Individuel Molecular Spccies of Major Glycolipids in Wheat Flour" (J. Amer. Org. Chem. Soc., (1992) £, No. 10, 1019-1022), describes the composition and distribution of the main glycolipids contained in wheat flour.
Ces produits, en particulier les digalactosyldiglycérides (DGDG), ont fait l'objet d'utilisations dans des domaines variés. On citera en particulier :These products, in particular digalactosyldiglycerides (DGDG), have been used in various fields. We will quote in particular:
- la demande PCT WO 88.08253 qui décrit l'utilisation des DGDG pour réduire la viscosité du chocolat,- PCT application WO 88.08253 which describes the use of DGDGs to reduce the viscosity of chocolate,
- la demande de brevet JP-A2-0503750 qui décrit l'utilisation des mêmes produits pour améliorer la qualité des produits issus de la farine de blé,- patent application JP-A2-0503750 which describes the use of the same products to improve the quality of products made from wheat flour,
- la demande de brevet JP-A2-03251506 qui décrit, quant à elle, une utilisation des mêmes produits comme agent désinfectant, - la demande de brevet EP-A-0249561 qui décrit des liposomes contenant des agents anti-inflammatoires et des glycolipides, en particulier des galactolipides dont le digalactosyldiglycéride,- patent application JP-A2-03251506 which describes, for its part, the use of the same products as a disinfecting agent, - patent application EP-A-0249561 which describes liposomes containing anti-inflammatory agents and glycolipids, in particular galactolipids including digalactosyldiglyceride,
- la demande de brevet EP-A-0009842 qui décrit, quant à elle, des liposomes contenant des digalactosyldiglycérides et des lécithines et leur utilisation pour la libération contrôlée des médicaments. La demanderesse a maintenant découvert que les galactosylglycérides et les extraits d'origine naturelle en contenant, notamment les extraits végétaux en contenant, agissent de façon très efficace sur la production extracellulaire de fibronectine par les fibroblastes humains, et amplifient ainsi le réseau extracellulaire de fibronectine.- Patent application EP-A-0009842 which describes, for its part, liposomes containing digalactosyldiglycerides and lecithins and their use for the controlled release of drugs. The Applicants have now discovered that galactosylglycerides and extracts of natural origin containing them, in particular plant extracts containing them, act very effectively on the extracellular production of fibronectin by human fibroblasts, and thus amplify the extracellular network of fibronectin.
La conséquence de cette découverte a conduit la demanderesse à tester et vérifier l'efficacité des compositions contenant des galactosyldiglycέrides et en particulier du DGDG, pour différentes applications tendant à renforcer les propriétés biomécaniques du derme ou des tissus conjonctifs, par exemple pour prévenir et/ou traiter les effets du vieillissement cutané.The consequence of this discovery led the applicant to test and verify the effectiveness of the compositions containing galactosyldiglycέrides and in particular of DGDG, for various applications tending to reinforce the biomechanical properties of the dermis or connective tissues, for example to prevent and / or treat the effects of skin aging.
Ainsi, l'invention concerne l'utilisation des galactosylglycérides, tout particulièrement des digalactosyldiglycérides, et des extraits notamment végétaux contenant ces produits, pour toutes les applications cosmétiques ou pharmaceu¬ tiques, notamment dermatologiques, où l'on cherche à obtenir une densification du réseau extracellulaire de fibronectine.Thus, the invention relates to the use of galactosylglycerides, very particularly digalactosyldiglycerides, and in particular plant extracts containing these products, for all cosmetic or pharmaceutical, in particular dermatological, applications where it is sought to obtain a densification of the network. extracellular fibronectin.
Un tel résultat permet, en particulier, de lutter contre les effets du vieillissement du derme et en particulier contre l'apparition des rides ou le relâchement cutané. En effet, il est bien connu que les modifications de l'apparence et surtout des propriétés mécaniques de la peau sont dues essentiellement à des modifications des composants du derme dont fait partie la fibronectine puisqu'elle assure, entre autres, le lien entre la cellule et le collagène.Such a result makes it possible, in particular, to combat the effects of aging of the dermis and in particular against the appearance of wrinkles or sagging skin. Indeed, it is well known that changes in the appearance and especially in the mechanical properties of the skin are due essentially to changes in the components of the dermis of which fibronectin is a part, since it ensures, among other things, the link between the cell and collagen.
La présente invention a donc pour objet principal de résoudre le problème technique consistant à fournir une composition cosmétique ou pharma¬ ceutique, notamment dermatologique, présentant une excellente efficacité sur la prévention ou le traitement des effets du vieillissement cutané, en particulier l'apparition des rides et sur le raffermissement cutané.The main object of the present invention is therefore to solve the technical problem of providing a cosmetic or pharmaceutical composition, in particular a dermatological composition, having excellent efficacy in preventing or treating the effects of skin aging, in particular the appearance of wrinkles. and on skin firming.
Ainsi, l'invention concerne l'utilisation d'au moins un galactosyl- diglycéride ou d'un extrait d'origine naturelle en contenant comme agent cosmétique favorisant la formation de fibronectine extracellulaire par les fibroblastes, permettant ainsi d'améliorer la cicatrisation cutanée, de renforcer les propriétés biomécaniques du derme ou des tissus conjonctifs, d'améliorer l'aspect de la surface de la peau, et permettant, en particulier, de prévenir ou traiter les effets du vieillissement cutané, tels que les rides ou le relâchement des tissus de soutien cutané. L'invention concerne donc, selon une de ses caractéristiques essentielles, l'utilisation d'au moins un galactosylglyceride ou d'un extrait d'origine naturelle en contenant comme agent cosmétique permettant d'améliorer la cicatrisation cutanée, de renforcer les propriétés biomécaniques du derme, d'améliorer l'aspect de la surface de la peau, ou de prévenir ou traiter les effets du vieillissement cutané, tels que les rides ou le relâchement des tissus de soutien cutané.Thus, the invention relates to the use of at least one galactosyl-diglyceride or of an extract of natural origin containing it as a cosmetic agent promoting the formation of extracellular fibronectin by fibroblasts, thus making it possible to improve cutaneous healing, to strengthen the biomechanical properties of the dermis or connective tissues, to improve the appearance of the surface of the skin, and making it possible, in particular, to prevent or treat the effects of skin aging, such as wrinkles or sagging tissues skin support. The invention therefore relates, according to one of its essential characteristics, to the use of at least one galactosylglyceride or of an original extract natural containing it as a cosmetic agent making it possible to improve skin healing, to strengthen the biomechanical properties of the dermis, to improve the appearance of the skin surface, or to prevent or treat the effects of skin aging, such as wrinkles or sagging skin support tissue.
Par amélioration des propriétés biomécaniques du derme, on entend toute amélioration d'origine biologique de la qualité structurelle du derme.By improvement of the biomechanical properties of the dermis, is meant any improvement of biological origin of the structural quality of the dermis.
En effet, l'intensification du réseau de la fibronectine extracellulaire permet d'améliorer l'adhésion des cellules aux macromolécules intercellulaires, telles que le collagène.In fact, the intensification of the extracellular fibronectin network makes it possible to improve the adhesion of cells to intercellular macromolecules, such as collagen.
Ainsi, l'utilisation selon l'invention permet plus particulièrement d'obtenir un raffermissement cutané, une prévention de l'apparition des rides ou une atténuation de leur profondeur.Thus, the use according to the invention more particularly makes it possible to obtain skin firming, prevention of the appearance of wrinkles or attenuation of their depth.
Suivant une première variante avantageuse, l'extrait d'origine naturelle précité est un extrait végétal, en particulier un extrait de céréale telle que le blé ou l'avoine, ou un extrait de feuilles ou de noix de Ginkgo Biloba.According to a first advantageous variant, the above-mentioned extract of natural origin is a plant extract, in particular a cereal extract such as wheat or oats, or an extract of leaves or nuts of Ginkgo Biloba.
Les galactosylglycérides utiles selon l'invention sont tout particulièrement les monogalactosylmonoglycérides (MGMG), les monogalactosyldiglycérides (MGDG), les digalactosylmonoglycέrides (DGMG) et les digalactosyldiglycérides (DGDG). On choisira avantageusement les mono- ou les digalactosyldiglycérides.The galactosylglycerides which are useful according to the invention are very particularly the monogalactosylmonoglycerides (MGMG), the monogalactosyldiglycerides (MGDG), the digalactosylmonoglycέrides (DGMG) and the digalactosyldiglycerides (DGDG). Advantageously, the mono- or digalactosyldiglycerides will be chosen.
Selon une variante particulièrement avantageuse de l'invention, le galactosylglyceride répondra à la formule (I) :According to a particularly advantageous variant of the invention, the galactosylglyceride will correspond to formula (I):
ÇH2- -C | H CH 2, — 0— A— GaiÇH 2 - -C | H CH 2, - 0— A— Gay
0 | 0 |0 | 0 |
R. - R 2 - ( I ) dans laquelle R. - R 2 - (I) in which
- Gai représente un groupement galactopyranosyle, de préférence bêta-D- galactopyranosyle,Gai represents a galactopyranosyl group, preferably beta-D-galactopyranosyl,
- Ri représente un groupement acyle de formule- Ri represents an acyl group of formula
C-RC-R
IIII
O dans laquelle R représente une chaîne aliphatique hydrocarbonée, saturée ou non, de préférence linéaire, et comprenant de 9 à 29 atomes de carbone, - R2 représente un atome d'hydrogène ou un groupement acyle, identique ou différent de R}, de formuleO in which R represents an aliphatic hydrocarbon chain, saturated or not, preferably linear, and comprising from 9 to 29 carbon atoms, - R2 represents a hydrogen atom or an acyl group, identical or different from R}, of formula
— C-R- C-R
1111
O dans laquelle R répond à la définition donnée ci-dessus,O in which R meets the definition given above,
- A représente :- A represents:
- une simple liaison, ou- a single link, or
- un groupement alpha- ou bêta-D-galactopyranosyle, ou- an alpha- or beta-D-galactopyranosyl group, or
- une chaîne constituée d'un enchaînement de plusieurs sucres, de préférence de deux ou trois sucres, choisis dans le groupe constitué par l'alpha- et le bêta-D- galactopyranosyle, l'alpha-D-glucopyranosyle, l'alpha-D- et l'alpha-L- manopyranosyle.- A chain consisting of a chain of several sugars, preferably two or three sugars, chosen from the group consisting of alpha- and beta-D- galactopyranosyle, alpha-D-glucopyranosyle, alpha- D- and alpha-L- manopyranosyle.
Selon une autre variante préférée de l'invention, les galactosyl¬ glycérides sont choisis parmi les mono- et les digalactosyldiglycérides (respectivement MGDG et DGDG) de formule (I) précitée, dans laquelleAccording to another preferred variant of the invention, the galactosyl¬ glycerides are chosen from mono- and digalactosyldiglycerides (respectively MGDG and DGDG) of formula (I) above, in which
- Gai, Rj et R2 répondent à la définition donnée précédemment, si ce n'est que R2 représente nécessairement un groupement acyle- Gai, Rj and R2 correspond to the definition given above, except that R2 necessarily represents an acyl group
- A représente une simple liaison ou un groupement alpha- ou bêta-D- galactopyranosyle. De préférence, le galactosyldiglycéride ci-dessus est choisi parmi les digalactosyldiglycérides (DGDG), c'est-à-dire parmi les produits dans lesquels A représente un groupement alpha- ou bêta-D-galactopyranosyle.- A represents a single bond or an alpha- or beta-D- galactopyranosyl group. Preferably, the galactosyldiglyceride above is chosen from digalactosyldiglycerides (DGDG), that is to say from products in which A represents an alpha- or beta-D-galactopyranosyl group.
De façon avantageuse, on choisira pour chacune des variantes précédentes des galactosylglycérides pour lesquels : - R\ représente un groupement acyle de formuleAdvantageously, galactosylglycerides will be chosen for each of the preceding variants for which: - R \ represents an acyl group of formula
—C-R—C-R
1111
OO
dans laquelle R représente une chaîne aliphatique hydrocarbonée linéaire contenant 15, 17 ou 19 atomes de carbone, saturée ou comprenant de 1 à 5 doubles liaisons, en position 7, 10 et/ou 13 pour un groupement acyle de 16 atomes de carbone, en position 9, 12 et/ou 15 pour un groupement acyle de 18 atomes de carbone, et en position 5, 8, 10, 14 et/ou 17 pour un groupement acyle de 20 atomes de carbone. - R2 représente un atome d'hydrogène ou un groupement acyle, identique ou différent de R}, de formulein which R represents a linear aliphatic hydrocarbon chain containing 15, 17 or 19 carbon atoms, saturated or comprising from 1 to 5 double bonds, in position 7, 10 and / or 13 for an acyl group of 16 carbon atoms, in position 9, 12 and / or 15 for an acyl group of 18 carbon atoms, and in positions 5, 8, 10, 14 and / or 17 for an acyl group of 20 carbon atoms. - R2 represents a hydrogen atom or an acyl group, identical or different from R}, of formula
—C-R—C-R
1111
OO
dans laquelle R répond à la définition donnée ci-dessus.in which R meets the definition given above.
Selon un autre de ses aspects, l'invention concerne également un procédé de traitement cosmétique destiné notamment à renforcer les propriétés biomécaniques du derme par une intensification de la formation de fibronectine extracellulaire par les fibroblastes, à obtenir un raffermissement cutané ou l'amélioration de la surface de la peau ou à prévenir ou à traiter les effets du vieillissement cutané tels que l'apparition des rides, consistant à appliquer localement sur les zones de la peau à traiter une composition contenant au moins un galactosylglyceride ou un extrait végétal en contenant. Pour la mise en oeuvre de ce procédé cosmétique, on choisira avantageusement le galactosylglyceride parmi les galactosylglycérides de formule (I) décrits ci-dessus, les produits préférés constitutant les mêmes sous- classes que celles définies précédemment.According to another of its aspects, the invention also relates to a cosmetic treatment process intended in particular to reinforce the biomechanical properties of the dermis by an intensification of the formation of extracellular fibronectin by fibroblasts, to obtain a skin tightening or the improvement of the surface of the skin or to prevent or treat the effects of skin aging such as the appearance of wrinkles, consisting in applying locally to the areas of the skin to be treated a composition containing at least one galactosylglyceride or a plant extract containing it. For the implementation of this cosmetic process, the galactosylglyceride will advantageously be chosen from the galactosylglycerides of formula (I) described above, the preferred products constituting the same subclasses as those defined above.
On choisira de façon particulièrement préférée les digalactosyldiglycérides.Particular preference will be given to choosing digalactosyldiglycerides.
Ces digalactosyldiglycérides ont été décrits dans diverses publications, en particulier dans le brevet US-4,377,567 ou dans la publication de D.V. Myhre dans Canadian Journal of Chemistry (1968) 4.6, 3071-3077, incorporée ici par référence. Les galactosylglycérides, peuvent être obtenus par synthèse, ou bien par extraction à partir de tissus animaux, en particulier cerveau, moelle épinière ou à partir de plantes, en particulier de céréales, selon des méthodes d'extraction largement décrites dans la littérature.These digalactosyldiglycerides have been described in various publications, in particular in US Pat. No. 4,377,567 or in the publication by D.V. Myhre in Canadian Journal of Chemistry (1968) 4.6, 3071-3077, incorporated herein by reference. The galactosylglycerides can be obtained by synthesis, or else by extraction from animal tissues, in particular brain, spinal cord or from plants, in particular from cereals, according to extraction methods widely described in the literature.
Pour cela, on se reportera par exemple à la publication de D.V. Myhre (1968) citée ci-dessus, ainsi qu'à celles de J.A. Prieto et al. (J. Amer. Org. Chem. Soc. (1992) 62 (4) 387-391), de G.G. Shipley et al. (Biochimica et biophysica acta (1973) 3J1 531-544), de P. Dupouey et al. (Immunochemistry (1976) . 289- 294), ou de Haru Kameyama et al. (J. Amer. Oil Chem. Soc. (1979) 56 549-51) ces publications étant incorporées ici par référence. Par ailleurs, certains galactosylglycérides, notamment le MGDG ou le DGDG sont disponibles dans le commerce, en particulier chez SIGMA. Chem. Co. (Saint-Louis ; Mo, USA).For this, see for example the publication by DV Myhre (1968) cited above, as well as those by JA Prieto et al. (J. Amer. Org. Chem. Soc. (1992) 62 (4) 387-391), of GG Shipley et al. (Biochimica et biophysica acta (1973) 3J1 531-544), by P. Dupouey et al. (Immunochemistry (1976). 289-294), or Haru Kameyama et al. (J. Amer. Oil Chem. Soc. (1979) 56 549-51) these publications being incorporated here by reference. In addition, some galactosylglycerides, in particular MGDG or DGDG are commercially available, in particular from SIGMA. Chem. Co. (Saint-Louis; Mo, USA).
Les extraits d'origine naturelle contenant les galactosylglycérides, utilisables pour la mise en oeuvre de l'invention, peuvent être obtenus par des procédés d'extraction bien connus de l'homme de l'art. Le solvant d'extraction utilisé sera de préférence un solvant polaire, tel qu'un alcool, un éther ou un hydrocarbure halogène. On choisira par exemple le méthanol, l'éthanol, l'isopropanol, l'éther έthylique ou le chloroforme.The extracts of natural origin containing the galactosylglycerides, which can be used for the implementation of the invention, can be obtained by extraction methods well known to those skilled in the art. The extraction solvent used will preferably be a polar solvent, such as an alcohol, an ether or a halogenated hydrocarbon. We will choose for example methanol, ethanol, isopropanol, ethyl ether or chloroform.
Selon un autre aspect de l'invention, les mêmes galactosylglycérides et tout particulièrement les digalactosyldiglycérides, et les extraits naturels en contenant, pourront être utilisés comme agent actif de compositions pharmaceutiques, en particulier dermatologiques, destinées à intensifier la synthèse de la fibronectine extracellulaire.According to another aspect of the invention, the same galactosylglycerides and very particularly the digalactosyldiglycerides, and the natural extracts containing them, can be used as active agent of pharmaceutical compositions, in particular dermatological compositions, intended to intensify the synthesis of extracellular fibronectin.
Ainsi selon cet autre aspect, l'invention concerne l'utilisation, à titre de principe actif, d'au moins un galactosylglyceride ou d'un extrait d'origine naturelle en contenant, pour la préparation d'une composition pharmaceutique, notamment dermatologique, destinée à prévenir ou traiter les diverses pathologies accompagnées d'une déficience en intensité du réseau de fibronectine extracellulaire dans les tissus conjonctifs, en particulier dans le derme, à améliorer les propriétés biomécaniques de la peau, à prévenir ou traiter les effets du vieillissement, en particulier du vieillissement cutané, à favoriser la cicatrisation ou à obtenir un raffermissement cutané.Thus according to this other aspect, the invention relates to the use, as active principle, of at least one galactosylglyceride or of an extract of natural origin containing it, for the preparation of a pharmaceutical composition, in particular dermatological, intended to prevent or treat various pathologies accompanied by a deficiency in the intensity of the extracellular fibronectin network in the connective tissues, in particular in the dermis, in improving the biomechanical properties of the skin, in preventing or treating the effects of aging, in particular of skin aging, to promote healing or to obtain skin firming.
L'invention concerne tout particulièrement l'utilisation, à titre de principe actif, d'au moins un galactosylglyceride, tel que décrit précédemment, notamment un digalactosyldiglycéride, pour la préparation de compositions pour les indications précitées.The invention relates very particularly to the use, as active principle, of at least one galactosylglyceride, as described above, in particular a digalactosyldiglyceride, for the preparation of compositions for the abovementioned indications.
Les galactosylglycérides sont avantageusement choisis pour cette application dans la famille I définie précédemment et les sous-familles de produits préférés sont les mêmes que celles définies précédemment. Selon une autre variante, le principe actif précité est un extrait d'origine naturelle, animale ou végétale, tel que précédement défini. Avantageusement, il s'agira d'un extrait végétal en particulier un extrait de céréale, telle que le blé ou l'avoine, ou un extrait de feuilles ou de noix de Gingko Biloba.The galactosylglycerides are advantageously chosen for this application from family I defined above and the sub-families of preferred products are the same as those defined above. According to another variant, the abovementioned active principle is an extract of natural, animal or plant origin, as previously defined. Advantageously, it will be a plant extract, in particular a cereal extract, such as wheat or oats, or an extract of Gingko Biloba leaves or nuts.
Les essais réalisés par la demanderesse ont clairement mis en évidence l'effet des galactosylglycérides, en particulier du digalactosyldiglycéride sur la formation de fibronectine extracellulaire, dont ces produits permettent d'amplifier le réseau. Cette constatation a conduit la demanderesse à utiliser les compositions selon l'invention pour toutes les applications où l'on cherche à favoriser une augmentation de la densité du réseau de fibronectine extracellulaire dans les tissus conjonctifs, en particulier dans les tissus de soutien cutané. Ainsi, les compositions selon l'invention sont donc tout particulièrement destinées au raffermissement de la peau, à l'accélération ou l'amélioration du processus de cicatrisation, à la prévention de l'apparition des rides ou à leur traitement, et d'une façon générale à la prévention ou au traitement des effets du vieillissement cutané. Les compositions de l'invention peuvent donc, en particulier, être avantageusement utilisées pour atténuer la profondeur des rides, notamment celles du visage et du cou.The tests carried out by the applicant have clearly demonstrated the effect of galactosylglycerides, in particular digalactosyldiglyceride on the formation of extracellular fibronectin, of which these products make it possible to amplify the network. This observation has led the applicant to use the compositions according to the invention for all applications where it is sought to promote an increase in the density of the extracellular fibronectin network in the connective tissues, in particular in the cutaneous support tissues. Thus, the compositions according to the invention are therefore very particularly intended for firming the skin, accelerating or improving the healing process, preventing the appearance of wrinkles or their treatment, and a generally for the prevention or treatment of the effects of skin aging. The compositions of the invention can therefore, in particular, be advantageously used to reduce the depth of wrinkles, in particular those of the face and the neck.
Elles permettent, également, d'améliorer les propriétés biomécaniques de la peau et ainsi de prévenir ou traiter les effets du vieillissement, en particulier du vieillissement cutané, de favoriser la cicatrisation ou d'obtenir un raffermissement cutané.They also make it possible to improve the biomechanical properties of the skin and thus to prevent or treat the effects of aging, in particular skin aging, to promote healing or to obtain skin firming.
Dans chacun des aspects précédemment décrits, on utilisera de préférence les concentrations en galactosylglyceride comprises entre 0,001 et 10 % en poids par rapport au poids total de la composition le contenant. Cette concentration sera de préférence comprise entre 0,01 et 5 % en poids par rapport au poids total de ladite composition.In each of the previously described aspects, the galactosylglyceride concentrations of between 0.001 and 10% by weight relative to the total weight of the composition containing it will preferably be used. This concentration will preferably be between 0.01 and 5% by weight relative to the total weight of said composition.
On utilisera de façon particulièrement avantageuse des extraits végétaux contenant au moins un galactosylglyceride, en particulier des extraits de céréales telles que le blé ou l'avoine. De tels produits existent commercialement. A titre d'exemple de produits commerciaux, on citera des produits commerciaux contenant du DGDG et du MGDG disponible chez SIGMA Chemical Company (Saint-Louis, Mo, USA).Plant extracts containing at least one galactosylglyceride, in particular cereal extracts such as wheat or oats, will be used in a particularly advantageous manner. Such products exist commercially. By way of example of commercial products, mention may be made of commercial products containing DGDG and MGDG available from SIGMA Chemical Company (Saint-Louis, Mo, USA).
Dans le cadre de l'invention, selon chacun des aspects précédents, l'administration des galactosylglycérides, en particulier des mono- ou digalactosyldiglycérides ou des extraits végétaux contenant ces différents produits, est réalisée selon les méthodes classiques, permettant la stimulation de la production de fibronectine extracellulaire. Habituellement, la voie la plus simple d'administration est la voie topique, en particulier lorsque l'on cherche à restaurer ou renforcer les propriétés biomécaniques des tissus de soutien cutané pour raffermir la peau, ou à prévenir ou atténuer l'apparition des rides, notamment celles du visage ou du cou. Ainsi, les compositions selon l'invention seront formulées, conformément aux techniques bien connues de l'homme de l'art, de manière appropriée pour l'administration topique, par exemple sous forme de crème, de lait, de lotion, gélifiée ou non, ou de pommade. Selon une variante avantageuse de l'invention, le galactosylglyceride ou l'extrait en contenant, est incorporé dans un excipient, véhicule ou support cosmétiquement ou pharmaceutiquement, notamment dermatologiquement acceptable. De tels supports sont bien connus de l'homme de l'art et résultent également des exemples de compositions cosmétiques ou de compositions pharmaceutiques, notamment dermatologiques décrites plus loin qui ont une portée générale.In the context of the invention, according to each of the preceding aspects, the administration of galactosylglycerides, in particular mono- or digalactosyldiglycerides or plant extracts containing these different products, is carried out according to conventional methods, allowing stimulation of the production of extracellular fibronectin. Usually, the simplest route of administration is the topical route, in particular when one seeks to restore or reinforce the biomechanical properties of the cutaneous support tissues to firm the skin, or to prevent or attenuate the appearance of wrinkles, especially those of the face or neck. Thus, the compositions according to the invention will be formulated, in accordance with techniques well known to those skilled in the art, suitably for topical administration, for example in the form of a cream, milk, lotion, gelled or not. , or ointment. According to an advantageous variant of the invention, the galactosylglyceride or the extract containing it, is incorporated into an excipient, vehicle or carrier cosmetically or pharmaceutically, in particular dermatologically acceptable. Such supports are well known to those skilled in the art and also result from examples of cosmetic compositions or pharmaceutical compositions, in particular dermatological compositions described below which are general in scope.
D'autres buts, caractéristiques et avantages de l'invention apparaîtront clairement à la lecture de la description explicative qui va suivre faite en référence à plusieurs exemples donnés uniquement à titre d'illustration et qui ne sauraient par conséquent en aucun cas limiter la portée de l'invention.Other objects, characteristics and advantages of the invention will appear clearly on reading the explanatory description which will follow made with reference to several examples given solely by way of illustration and which therefore cannot in any way limit the scope of the invention.
Les figures 1 à 4, qui font partie intégrante de l'exemple 1, sont des copies de photographies obtenues lors de l'observation au microscope à fluorescence du réseau extracellulaire de fibronectine sécrétée respectivement par :FIGS. 1 to 4, which are an integral part of Example 1, are copies of photographs obtained during observation under a fluorescent microscope of the extracellular network of fibronectin secreted respectively by:
- figure 1 : des cellules-témoin prélevées chez un donneur de 20 ans ; - figure 2 : les mêmes cellules que pour la figure 1 mais traitées par du- Figure 1: control cells taken from a 20-year-old donor; - Figure 2: the same cells as for Figure 1 but treated with
DGDG ;DGDG;
- figure 3 : des cellules-témoin prélevées chez un donneur de 46 ans ;- Figure 3: control cells taken from a 46-year-old donor;
- figure 4 : les mêmes cellules que la figure 3 mais traitées par du DGDG. Dans ces exemples, les pourcentages sont exprimés en poids, sauf indication contraire. Dans le cas des extraits, les quantités de ceux-ci sont exprimées en poids sec. - Figure 4: the same cells as Figure 3 but treated with DGDG. In these examples, the percentages are expressed by weight, unless otherwise indicated. In the case of extracts, the quantities thereof are expressed in dry weight.
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EXEMPLESEXAMPLES
Exemple 1 : Mise en évidence de l'augmentation de la formation de fibronectine extracellulaire en présence de DGDGEXAMPLE 1 Demonstration of the Increase in the Formation of Extracellular Fibronectin in the Presence of DGDG
A - Principe de la méthodeA - Principle of the method
L'immunolocalisation de la fibronectine repose sur le principe général de la liaison spécifique d'un anticorps à son antigène. La technique est réalisée par immuno-marquage indirect. Dans un premier temps, un anticorps antifibronectine préparé chez le lapin est mis en contact avec la couche cellulaire.The immunolocalization of fibronectin is based on the general principle of the specific binding of an antibody to its antigen. The technique is performed by indirect immunostaining. First, an anti-fibronectin antibody prepared in rabbits is brought into contact with the cell layer.
Dans un deuxième temps, le complexe formé par la liaison de l'anticorps spécifique à son antigène est révélé par l'addition d'une globuline dirigée contre les Ig G de lapin couplé à un fluorochrome, ici, la R phycoérythrine.In a second step, the complex formed by the binding of the specific antibody to its antigen is revealed by the addition of a globulin directed against rabbit Ig G coupled to a fluorochrome, here, R phycoerythrin.
B - ProtocoleB - Protocol
Les anticorps utilisés sont :The antibodies used are:
1. Anticorps de lapin anti-fibronectine humaine (BTI Réf. BT 551 P)1. Rabbit anti-human fibronectin antibody (BTI Ref. BT 551 P)
2. Anticorps de chèvre F(ab')2 anti-immunoglobuline de lapin (G + L) marqués à la phycoérythrine (TAGO Réf. 4920).2. Goat antibody F (ab ') 2 rabbit anti-immunoglobulin (G + L) labeled with phycoerythrin (TAGO Ref. 4920).
. Culture. Culture
Les cellules utilisées sont des fibroblastes issus de plasties chirurgicales mammaires ou abdominales de donneurs adultes sains. Les cellules sont ensemencées sur des lamelles de verre, et 24 h après l'ensemencement, le milieu est renouvelé en présence ou non de DGDG. Le milieu de culture initial est du MEM + 10 % de sérum de veau foetal (SVF). Pendant la phase de traitement, le milieu est constitué de milieu MEM + 2,5 % sérum de veau foetal. Le DGDG est mis en solution dans du DMSO et utilisé sur les cultures à la concentration finale de 750 μg/ml. Les opérations de culture se déroulent de la manière suivante :The cells used are fibroblasts from mammary or abdominal surgical plasties from healthy adult donors. The cells are inoculated on glass slides, and 24 h after inoculation, the medium is renewed in the presence or not of DGDG. The initial culture medium is MEM + 10% fetal calf serum (SVF). During the treatment phase, the medium consists of MEM medium + 2.5% fetal calf serum. The DGDG is dissolved in DMSO and used on the cultures at the final concentration of 750 μg / ml. Cultivation operations take place as follows:
Au jour J=0 : Ensemencement avec du milieu MEM + 10 % SVFOn day D = 0: Inoculation with MEM medium + 10% SVF
Au jour J+2 : Traitement DGDG (750 g/ml) avec milieu MEM + 2,5 % SVFOn day D + 2: DGDG treatment (750 g / ml) with MEM medium + 2.5% FCS
Au jour J+4 : Traitement identiqueOn day D + 4: Identical treatment
Au jour J+6 : Traitement identiqueOn day D + 6: Identical treatment
Au jour J+8 : Fixation des cellulesOn day D + 8: Fixation of cells
. Fixation. Fixation
Après rinçage des lamelles avec le tampon PBS, les cellules sont fixées 20 min au paraformaldéhyde (3,7 % dans PBS) à 4'C.After rinsing the coverslips with PBS buffer, the cells are fixed for 20 min with paraformaldehyde (3.7% in PBS) at 4 ° C.
. Réaction immunologique. Immunological reaction
Après 2 lavages des lamelles en tampon phosphate PBS puis en tampon PAB (PBS additionné de 0,2 % de sérum albumine bovine (BSA)), l'anticorps antifibronectine (dilué au l/250ème dans PAB) est mis en contact avec les cellules pendant 60 min à 4*C.After 2 washes of the coverslips in PBS phosphate buffer and then in PAB buffer (PBS added with 0.2% bovine serum albumin (BSA)), the anti-fibronectin antibody (diluted to 1 / 250th in PAB) is brought into contact with the cells. for 60 min at 4 * C.
Cette opération est suivie d'un passage en solution tampon (PAB) puis de 2 bains de 15 min dans le même tampon.This operation is followed by passing through a buffer solution (PAB) and then 2 baths of 15 min in the same buffer.
La deuxième partie de la réaction est réalisée par l'addition du conjugué fluorescent (dilué au l/500ème dans PAB) pendant 45 min à température ambiante. Les cellules sont alors de nouveau rincées avec du PBS.The second part of the reaction is carried out by adding the fluorescent conjugate (diluted to 1 / 500th in PAB) for 45 min at room temperature. The cells are then again rinsed with PBS.
. Observation. Observation
Chaque lamelle est ensuite séchée et montée sur lame (milieu de montage : glycérol 33 % dans PBS).Each strip is then dried and mounted on a slide (mounting medium: 33% glycerol in PBS).
L'observation est réalisée au microscope à fluorescence (OLYMPUS BH2). . RésultatsThe observation is carried out under a fluorescence microscope (OLYMPUS BH2). . Results
Cette méthode a été appliquée à des fibroblastes de donneurs d'âges différents (17, 20, 46 et 47 ans) et ayant un nombre de repiquage croissants (de 3 à 8 passages). L'observation des figures 1, 2, 3 et 4 correspondant au donneur deThis method was applied to fibroblasts of donors of different ages (17, 20, 46 and 47) and having an increasing number of subcultures (from 3 to 8 passages). The observation of Figures 1, 2, 3 and 4 corresponding to the donor
20 ans pour les deux premières et à celui de 46 ans pour les deux secondes, montre que l'aspect du réseau extracellulaire de fibronectine change radicalement en présence de DGDG : il s'étoffe en présence de la substance, la distribution des fibres et leur organisation sont différentes. - La détection de la fibronectine extracellulaire par immunofluorescence dans les cellules témoins (figures 1 et 3) révèle la présence d'un ensemble de filaments rassemblés à certains endroits mais orientés dans l'axe longitudinal des cellules, parallèles entre eux.20 years for the first two and that of 46 years for the second two, shows that the appearance of the extracellular network of fibronectin changes radically in the presence of DGDG: it expands in the presence of the substance, the distribution of fibers and their organization are different. - The detection of extracellular fibronectin by immunofluorescence in the control cells (Figures 1 and 3) reveals the presence of a set of filaments gathered in certain places but oriented in the longitudinal axis of the cells, parallel to each other.
L'orientation des fibres est nette. La condensation des fibres présente au niveau de certaines cellules contraste avec la présence de fines fibres entrecoupées et isolées.The orientation of the fibers is clear. The condensation of the fibers present in certain cells contrasts with the presence of fine fibers interspersed and isolated.
- Le traitement par le DGDG (figures 2, 4) fait apparaître une densité de filaments beaucoup plus importante.- Treatment with DGDG (Figures 2, 4) reveals a much higher density of filaments.
Les fibres sont associées entre elles, entrelacées. Elles marquent une sorte de tourbillons, le contour des cellules n'est pas discernableThe fibers are associated with each other, intertwined. They mark a kind of swirls, the outline of the cells is not discernible
Les fibres apparaissent imbriquées dans un filet aux mailles relativement serrées, de type "dentelle" ou "écheveau".The fibers appear to be nested in a net with relatively tight stitches, of the "lace" or "skein" type.
La fibronectine dans les cultures provenant de sujets jeunes (17- 20 ans) apparaît sous forme de fibres plus abondantes que chez les sujets "âgés" (46-47 ans).Fibronectin in cultures from young subjects (17-20 years) appears as more abundant fibers than in "older" subjects (46-47 years).
Il ressort de l'étude que le DGDG provoque une augmentation considérable de la formation de fibronectine extracellulaire par les fibroblastes et ce, quelque soit l'âge des sujets.The study shows that DGDG causes a considerable increase in the formation of extracellular fibronectin by fibroblasts, regardless of the age of the subjects.
Le phénomène paraît être plus important chez les sujets de 46 ans (voir photos) étant donné que le réseau de base est moindre.The phenomenon appears to be more significant in subjects aged 46 (see photos) since the basic network is less.
Si les cellules ont été cultivées très tôt en présence de DGDG (avant l'ensemencement sur des lamelles), le résultat ne diffère pas, la concentration des filaments paraît être la même qu'après 3 traitements successifs. Exemple 2 : Mise en évidence de l'activité du digalactosyldiglycéride augmentant la capacité d'adhésion des fibroblastes.If the cells were cultivated very early in the presence of DGDG (before seeding on coverslips), the result does not differ, the concentration of the filaments appears to be the same as after 3 successive treatments. Example 2: Demonstration of the activity of digalactosyldiglyceride increasing the adhesion capacity of fibroblasts.
La présente expérience a pour but de vérifier la stimulation de la capacité d'adhésion de fibroblastes humains normaux traités par du DGDG. Pour cela, on observera la rapidité d'adhésion à un support plastique de ces cellules en culture.The purpose of this experiment is to verify the stimulation of the adhesion capacity of normal human fibroblasts treated with DGDG. For this, we will observe the speed of adhesion to a plastic support of these cells in culture.
On réalise dans un flacon de 75 ml une culture de fibroblastes humains normaux, obtenus comme indiqué précédemment à l'exemple 1. Ces cellules sont cultivées de manière classique dans du milieu MEM additionné de 10 % de sérum de veau foetal, auquel on ajoute du DGDG (SIGMA) à la concentration de 750μg/ml. La culture est conduite pendant une semaine, avec deux renouvellements du milieu de culture dans la semaine, toujours avec la même concentration en DGDG.A culture of normal human fibroblasts is obtained in a 75 ml flask, obtained as indicated above in Example 1. These cells are cultured in a conventional manner in MEM medium supplemented with 10% fetal calf serum, to which is added DGDG (SIGMA) at the concentration of 750μg / ml. The culture is carried out for one week, with two replenishments of the culture medium in the week, always with the same concentration of DGDG.
Ensuite, après rinçage de la monocouche de cellules par un tampon phosphate PBS, on décolle les cellules en laissant agir pendant 30 minutes une solution 2 mM d'EDTA (acide éthylènediaminetétraacétique).Then, after rinsing the monolayer of cells with a PBS phosphate buffer, the cells are peeled off, leaving a 2 mM solution of EDTA (ethylenediaminetetraacetic acid) to act for 30 minutes.
Après centrifugation, les cellules sont remises en suspension dans un milieu de culture classique (MEM additionné de 10 % de sérum de veau foetal).After centrifugation, the cells are resuspended in a conventional culture medium (MEM supplemented with 10% fetal calf serum).
Pour évaluer la capacité d'adhésion des fibroblastes, on introduit dans les boîtes de culture en matière plastique de 60 mm de diamètre 3.10^ cellules en suspension dans le milieu (environ 3 ml). Après un temps déterminé après cette introduction dans les boîtes, à 15, 20 et 35 minutes, on prélève la totalité du surnageant et on compte les cellules restées en suspension, au moyen d'un compteur de cellules, ZM, COULTRONICS, pour en déduire le nombre de cellules restées attachées aux parois des boîtes formant support. Chaque essai est fait en trois exemplaires. On compare les résultats ainsi obtenus avec ceux correspondant à des fibroblastes témoins, de même origine, ayant été cultivés dans les mêmes conditions pendant une semaine, si ce n'est que le milieu de culture ne contenait pas de DGDG. On calcule alors le pourcentage des cellules adhérant aux parois par rapport aux essais témoin, en fonction du temps. Les résultats obtenus figurent au tableau I ci-après. TABLEAU ITo evaluate the adhesion capacity of the fibroblasts, 3.10 cells suspended in the medium (approximately 3 ml) are introduced into the 60 mm diameter plastic culture dishes. After a determined time after this introduction into the dishes, at 15, 20 and 35 minutes, the entire supernatant is removed and the cells remaining in suspension are counted, using a cell counter, ZM, COULTRONICS, to deduce therefrom. the number of cells remaining attached to the walls of the support boxes. Each test is done in triplicate. The results thus obtained are compared with those corresponding to control fibroblasts, of the same origin, having been cultured under the same conditions for one week, except that the culture medium did not contain DGDG. The percentage of cells adhering to the walls is then calculated relative to the control tests, as a function of time. The results obtained are shown in Table I below. TABLE I
Temps Pourcentage de cellules adhérant au (minutes) support, par rapport au témoinTime Percentage of cells adhering to the support (minutes), compared to the control
15 22 ± 2 %15 22 ± 2%
20 64 ± 6 %20 64 ± 6%
35 64 ± 6 %35 64 ± 6%
Il ressort très clairement de ces résultats, que le DGDG joue un rôle positif très important dans le mécanisme d'adhésion des fibroblastes. Ceci constitue une observation qui va dans le même sens que celle de l'exemple 1 sur l'augmentation du réseau extracellulaire de fibronectine, sachant qu'il était connu que la fibronectine intervient dans l'adhésion des cellules du derme entre elles et des cellules avec des protéines telles que le collagène.It is very clear from these results that the DGDG plays a very important positive role in the adhesion mechanism of fibroblasts. This constitutes an observation which goes in the same direction as that of Example 1 on the increase in the extracellular network of fibronectin, knowing that it was known that fibronectin intervenes in the adhesion of the cells of the dermis between them and of the cells. with proteins such as collagen.
Exem le 3 ; Produit à effet cicatrisantExample 3; Healing effect
On prépare une dispersion stable contenant 1 % en poids de DGDG et 2 % de collagène.A stable dispersion is prepared containing 1% by weight of DGDG and 2% of collagen.
Après homogénéisation, on observe une dispersion de liposomes de dimensions inférieures ou égales à 20 nm.After homogenization, a dispersion of liposomes with dimensions less than or equal to 20 nm is observed.
On gélifie la dispersion par addition de 0,2 % en poids de Carbopol 940 et on ajoute un conservateur.The dispersion is gelled by adding 0.2% by weight of Carbopol 940 and a preservative is added.
Exemple 4 : Produit à effet antirides On prépare une émulsion stable contenant :Example 4 Product with Anti-Wrinkle Effect A stable emulsion is prepared containing:
.2 % en poids de DGDG.2% by weight of DGDG
. 18 % en poids d'un triglycéride caprique - caprilique (Miglyol 812). 18% by weight of a caprilic - caprilic triglyceride (Miglyol 812)
. 80 % eau + conservateurs classiques de la façon suivante : Le DGDG est dissous dans l'huile et l'ensemble est amené à 75*C. L'eau avec les conservateurs est chauffée séparément à 75#C. Une partie de l'eau est alors incorporée dans la phase grasse, puis l'ensemble est introduit dans la partie restante de phase aqueuse, à 75*C sous agitation magnétique. L'émulsion est amenée à 80*C toujours sous agitation magnétique, puis homogénéisée 5 min à 11 000 tr/min, à l'aide de l'Ultra - Turax. Elle est ensuite plongée dans un bain de glace afin d'obtenir un refroidissement rapide figeant la structure. . 80% water + classic preservatives as follows: The DGDG is dissolved in the oil and the whole is brought to 75 ° C. The water with the preservatives is heated separately to 75 # C. Part of the water is then incorporated into the fatty phase, then the whole is introduced into the remaining part of the aqueous phase, at 75 ° C. with magnetic stirring. The emulsion is brought to 80 ° C. still under magnetic stirring, then homogenized for 5 min at 11,000 rpm, using Ultra - Turax. It is then immersed in an ice bath in order to obtain rapid cooling, freezing the structure.

Claims

REVENDICATIONS
1. Utilisation d'au moins un galactosylglyceride ou d'un extrait d'origine naturelle en contenant comme agent cosmétique permettant d'améliorer la cicatrisation cutanée, de renforcer les propriétés biomécaniques du derme, d'améliorer l'aspect de la surface de la peau, ou de prévenir ou traiter les effets du vieillissement cutané, tels que les rides ou le relâchement des tissus de soutien cutané.1. Use of at least one galactosylglyceride or an extract of natural origin containing it as a cosmetic agent making it possible to improve skin healing, to reinforce the biomechanical properties of the dermis, to improve the appearance of the surface of the skin, or to prevent or treat the effects of skin aging, such as wrinkles or sagging skin support tissues.
2. Utilisation selon la revendication 1, caractérisée en ce que ledit agent cosmétique est destiné à obtenir un raffermissement cutané, une prévention de l'apparition des rides, ou une atténuation de leur profondeur.2. Use according to claim 1, characterized in that said cosmetic agent is intended to obtain a skin tightening, prevention of the appearance of wrinkles, or attenuation of their depth.
3. Utilisation selon la revendication 1 ou 2, caractérisée en ce que ledit extrait d'origine naturelle est un extrait végétal, en particulier un extrait de céréale telle que le blé ou l'avoine, ou un extrait de feuilles ou de noix de Ginkgo Biloba. 3. Use according to claim 1 or 2, characterized in that said extract of natural origin is a plant extract, in particular a cereal extract such as wheat or oats, or an extract of leaves or Ginkgo nuts Biloba.
4. Utilisation selon la revendication 3, caractérisée en ce que l'extrait végétal est obtenu par extraction au moyen d'un solvant polaire.4. Use according to claim 3, characterized in that the plant extract is obtained by extraction using a polar solvent.
5. Utilisation selon la revendication 4, caractérisée en ce que le solvant polaire précité est un alcool, en particulier le méthanol, l'éthanol ou l'isopropanol, un éther, en particulier l'éther éthylique, ou un hydrocarbure halogène, en particulier le chloroforme.5. Use according to claim 4, characterized in that the aforementioned polar solvent is an alcohol, in particular methanol, ethanol or isopropanol, an ether, in particular ethyl ether, or a halogenated hydrocarbon, in particular chloroform.
6. Utilisation selon l'une des revendications 1 à 6, caractérisée en ce que ledit galactosylglyceride répondant à la formule (I) :6. Use according to one of claims 1 to 6, characterized in that said galactosylglyceride corresponding to formula (I):
CH: — CH CH,— O— A— Gai i 2 i 2 CH: - CH CH, - O— A— Gai i 2 i 2
O O k (I) OO k (I)
dans laquellein which
- Gai représente un groupement galactopyranosyle, de préférence bêta-D- galactopyranosyle,Gai represents a galactopyranosyl group, preferably beta-D-galactopyranosyl,
- R\ représente un groupement acyle de formule- R \ represents an acyl group of formula
—C-R—C-R
IIII
O dans laquelle R représente une chaîne aliphatique hydrocarbonée, saturée ou non, de préférence linéaire, et comprenant de 9 à 29 atomes de carbone, - R2 représente un atome d'hydrogène ou un groupement acyle, identique ou différent de Rj, de formuleO in which R represents an aliphatic hydrocarbon chain, saturated or not, preferably linear, and comprising from 9 to 29 carbon atoms, - R2 represents a hydrogen atom or an acyl group, identical or different from Rj, of formula
—C-R—C-R
1111
OO
dans laquelle R répond à la définition donnée ci-dessus,in which R meets the definition given above,
- A représente :- A represents:
- une simple liaison, ou- a single link, or
- un groupement alpha- ou bêta-D-galactopyranosyle, ou - une chaîne constituée d'un enchaînement de plusieurs sucres, de préférence de deux ou trois sucres, choisis dans le groupe constitué par l'alpha- et le bêta-D- galactopyranosyle, l'alpha-D-glucopyranosyle, l'alpha-D- et l'alpha-L- manopyranosyle.- an alpha- or beta-D-galactopyranosyl group, or - a chain consisting of a chain of several sugars, preferably two or three sugars, chosen from the group consisting of alpha- and beta-D- galactopyranosyle , alpha-D-glucopyranosyl, alpha-D- and alpha-L-manopyranosyl.
7. Utilisation selon la revendication 6, caractérisée en ce que ledit galactosylglyceride est un monogalactosyldiglycéride (MGDG) ou un digalactosyldiglycéride (DGDG) répondant à la formule (I) dans laquelle7. Use according to claim 6, characterized in that said galactosylglyceride is a monogalactosyldiglyceride (MGDG) or a digalactosyldiglyceride (DGDG) corresponding to formula (I) in which
- Gai représente un groupement galactopyranosyle, de préférence bêta-D- galactopyranosyle, - i représente un groupement acyle de formule- Gai represents a galactopyranosyl group, preferably beta-D- galactopyranosyl, - i represents an acyl group of formula
—C-R—C-R
1111
O dans laquelle R représente une chaîne aliphatique hydrocarbonée, saturée ou non, de préférence linéaire, et comprenant de 9 à 29 atomes de carbone, - R2 représente un groupement acyle, identique ou différent de Rj, de formuleO in which R represents an aliphatic hydrocarbon chain, saturated or not, preferably linear, and comprising from 9 to 29 carbon atoms, - R2 represents an acyl group, identical or different from Rj, of formula
—C-R—C-R
1111
OO
dans laquelle R répond à la définition donnée ci-dessus, - A représente :in which R meets the definition given above, - A represents:
- une simple liaison, ou- a single link, or
- un groupement alpha- ou bêta-D-galactopyranosyle. - an alpha- or beta-D-galactopyranosyl group.
8. Utilisation selon la revendication 7, caractérisée en ce que le digalactosylglycéride est un digalactosyldiglycéride (DGDG) répondant à la formule (I) : dans laquelle - Gai représente un groupement galactopyranosylc, de préférence bêta-D- galactopyranosyle,8. Use according to claim 7, characterized in that the digalactosylglyceride is a digalactosyldiglyceride (DGDG) corresponding to formula (I): in which - Gai represents a galactopyranosyl group, preferably beta-D-galactopyranosyl,
- R représente un groupement acyle de formule- R represents an acyl group of formula
—C-R—C-R
IIII
O dans laquelle R représente une chaîne aliphatique hydrocarbonée, saturée ou non, de préférence linéaire, et comprenant de 9 à 29 atomes de carbone,O in which R represents an aliphatic hydrocarbon chain, saturated or not, preferably linear, and comprising from 9 to 29 carbon atoms,
- R2 représente un groupement acyle, identique ou différent de R , de formule- R2 represents an acyl group, identical or different from R, of formula
—C-R—C-R
IIII
OO
dans laquelle R répond à la définition donnée ci-dessus,in which R meets the definition given above,
- A représente un groupement alpha- ou bêta-D-galactopyranosyle.- A represents an alpha- or beta-D-galactopyranosyl group.
9. Utilisation selon l'une des revendications 6 à 8, caractérisée en ce que le galactosylglyceride répond à la formule (I) telle que définie à la revendication 7 dans laquelle9. Use according to one of claims 6 to 8, characterized in that the galactosylglyceride corresponds to formula (I) as defined in claim 7 in which
- Ri représente un groupement acyle de formule- Ri represents an acyl group of formula
—C-R—C-R
IIII
O dans laquelle R représente une chaîne aliphatique hydrocarbonée linéaire contenant 15, 17 ou 19 atomes de carbone, saturée ou comprenant de 1 à 5 doubles liaisons, en position 7, 10 et/ou 13 pour un groupement acyle de 16 atomes de carbone, en position 9, 12 et/ou 15 pour un groupement acyle de 18 atomes de carbone, et en position 5, 8, 10, 14 et/ou 17 pour un groupement acyle de 20 atomes de carbone. - R2 représente un atome d'hydrogène ou un groupement acyle, identique ou différent de Ri de formuleO in which R represents a linear aliphatic hydrocarbon chain containing 15, 17 or 19 carbon atoms, saturated or comprising from 1 to 5 double bonds, in position 7, 10 and / or 13 for an acyl group of 16 carbon atoms, in position 9, 12 and / or 15 for an acyl group of 18 carbon atoms, and in position 5, 8, 10, 14 and / or 17 for an acyl group of 20 carbon atoms. - R2 represents a hydrogen atom or an acyl group, identical or different from Ri of formula
—C-R—C-R
1111
OO
dans laquelle R répond à la définition donnée ci-dessus.in which R meets the definition given above.
10. Utilisation selon l'une des revendications 1 à 9, caractérisée en ce que le galactosylglyceride ou l'extrait d'origine naturelle en contenant est présent dans une composition à une concentration comprise entre 0,001 et 10 %, de préférence entre 0,01 et 5 %, en poids par rapport au poids total de ladite composition10. Use according to one of claims 1 to 9, characterized in that the galactosylglyceride or the extract of natural origin containing it is present in a composition at a concentration of between 0.001 and 10%, preferably between 0.01 and 5%, by weight relative to the total weight of said composition
11. Utilisation, à titre de principe actif, d'au moins un galactosyl¬ glyceride ou d'un extrait d'origine naturelle en contenant pour la préparation d'une composition pharmaceutique, notamment dermatologique, destinée à prévenir ou traiter les diverses pathologies accompagnées d'une déficience en intensité du réseau de fibronectine extracellulaire dans les tissus conjonctifs, en particulier dans le derme, à améliorer les propriétés biomécaniques de la peau, à prévenir ou traiter les effets du vieillissement, en particulier du vieillissement cutané, à favoriser la cicatrisation ou à obtenir un raffermissement cutané. 11. Use, as active principle, of at least one galactosyl¬ glyceride or of an extract of natural origin containing it for the preparation of a pharmaceutical composition, in particular dermatological, intended to prevent or treat the various pathologies accompanied a deficiency in the intensity of the extracellular fibronectin network in the connective tissues, in particular in the dermis, in improving the biomechanical properties of the skin, in preventing or treating the effects of aging, in particular in skin aging, in promoting healing or to get a skin firming.
12. Utilisation selon la revendication 11, caractérisée en ce que ledit extrait d'origine naturelle est un extrait végétal, en particulier un extrait de céréale telle que le blé ou l'avoine, ou un extrait de feuilles ou de noix de Ginkgo Biloba.12. Use according to claim 11, characterized in that said extract of natural origin is a plant extract, in particular a cereal extract such as wheat or oats, or an extract of leaves or nuts of Ginkgo Biloba.
13. Utilisation selon la revendication 12, caractérisée en ce que l'extrait végétal est obtenu par extraction au moyen d'un solvant polaire. 13. Use according to claim 12, characterized in that the plant extract is obtained by extraction using a polar solvent.
14. Utilisation selon la revendication 13, caractérisée en ce que le solvant polaire précité est un alcool, en particulier le méthanol, l'éthanol ou l'isopropanol, un éther, en particulier l'éther éthylique, ou un hydrocarbure halogène, en particulier le chloroforme.14. Use according to claim 13, characterized in that the aforementioned polar solvent is an alcohol, in particular methanol, ethanol or isopropanol, an ether, in particular ethyl ether, or a halogenated hydrocarbon, in particular chloroform.
15. Utilisation selon l'une des revendications 11 à 14, caractérisée en ce que ledit galactosylglyceride est un galactosyldiglycéride répondant à la formule (I) :15. Use according to one of claims 11 to 14, characterized in that said galactosylglyceride is a galactosyldiglyceride corresponding to formula (I):
C I H 2: C , H CH, 2 — O" A— GaiC I H 2: C, H CH, 2 - O "A— Gai
O 0O 0
1 l1 l
R. R. ( I ) dans laquelleRR (I) in which
- Gai représente un groupement galactopyranosyle, de préférence bêta-D- galactopyranosyle,Gai represents a galactopyranosyl group, preferably beta-D-galactopyranosyl,
- Ri représente un groupement acyle de formule- Ri represents an acyl group of formula
—C-R—C-R
IIII
O dans laquelle R représente une chaîne aliphatique hydrocarbonée, saturée ou non, de préférence linéaire, et comprenant de 9 à 29 atomes de carbone,O in which R represents an aliphatic hydrocarbon chain, saturated or not, preferably linear, and comprising from 9 to 29 carbon atoms,
- R2 représente un atome d'hydrogène ou un groupement acyle, identique ou différent de Rj_, de formule- R2 represents a hydrogen atom or an acyl group, identical or different from R j _, of formula
—C-R—C-R
IIII
O dans laquelle R répond à la définition donnée ci-dessus,O in which R meets the definition given above,
- A représente : - une simple liaison, ou- A represents: - a single bond, or
- un groupement alpha- ou bêta-D-galactopyranosyle, ou- an alpha- or beta-D-galactopyranosyl group, or
- une chaîne constituée d'un enchaînement de plusieurs sucres, de préférence de deux ou trois sucres, choisis dans le groupe constitué par l'alpha- et le bêta-D- galactopyranosyle, l'alpha-D-glucopyranosyle, l'alpha-D- et l'alpha-L- manopyranosyle.- A chain consisting of a chain of several sugars, preferably two or three sugars, chosen from the group consisting of alpha- and beta-D- galactopyranosyle, alpha-D-glucopyranosyle, alpha- D- and alpha-L- manopyranosyle.
16. Utilisation selon la revendication 15, caractérisée en ce que ledit galactosylglyceride est un monogalactosyldiglycéride (MGDG) ou un digalactosyldiglycéride (DGDG) répondant à la formule (I) dans laquelle - Gai représente un groupement galactopyranosyle, de préférence bêta-D- galactopyranosyle,16. Use according to claim 15, characterized in that said galactosylglyceride is a monogalactosyldiglyceride (MGDG) or a digalactosyldiglyceride (DGDG) corresponding to formula (I) in which - Gai represents a galactopyranosyl group, preferably beta-D-galactopyranosyl,
- Ri représente un groupement acyle de formule- Ri represents an acyl group of formula
—C-R—C-R
IIII
O dans laquelle R représente une chaîne aliphatique hydrocarbonée, saturée ou non, de préférence linéaire, et comprenant de 9 à 29 atomes de carbone,O in which R represents an aliphatic hydrocarbon chain, saturated or not, preferably linear, and comprising from 9 to 29 carbon atoms,
- R2 représente un groupement acyle, identique ou différent de Ri, de formule- R2 represents an acyl group, identical or different from Ri, of formula
—C-R—C-R
1111
O dans laquelle R répond à la définition donnée ci-dessus,O in which R meets the definition given above,
- A représente :- A represents:
- une simple liaison, ou- a single link, or
- un groupement alpha- ou bêta-D-galactopyranosyle. - an alpha- or beta-D-galactopyranosyl group.
17. Utilisation selon la revendication 16, caractérisée en ce que le digalactosylglycéride est un digalactosyldiglycéride (DGDG) répondant à la formule (I) dans laquelle17. Use according to claim 16, characterized in that the digalactosylglyceride is a digalactosyldiglyceride (DGDG) corresponding to formula (I) in which
- Gai représente un groupement galactopyranosyle, de préférence bêta-D- galactopyranosyle,Gai represents a galactopyranosyl group, preferably beta-D-galactopyranosyl,
- R représente un groupement acyle de formule- R represents an acyl group of formula
—C-R—C-R
IIII
O dans laquelle R représente une chaîne aliphatique hydrocarbonée, saturée ou non, de préférence linéaire, et comprenant de 9 à 29 atomes de carbone,O in which R represents an aliphatic hydrocarbon chain, saturated or not, preferably linear, and comprising from 9 to 29 carbon atoms,
- R2 représente un groupement acyle, identique ou différent de Ri, de formule- R2 represents an acyl group, identical or different from Ri, of formula
—C-R—C-R
IIII
OO
dans laquelle R répond à la définition donnée ci-dessus,in which R meets the definition given above,
- A représente un groupement alpha- ou bêta-D-galactopyranosyle.- A represents an alpha- or beta-D-galactopyranosyl group.
18. Utilisation selon l'une des revendications 15 à 18, caractérisée en ce que le galactosylglyceride répond à la formule (I) telle que définie à la revendication 7 dans laquelle - Ri représente un groupement acyle de formule18. Use according to one of claims 15 to 18, characterized in that the galactosylglyceride corresponds to formula (I) as defined in claim 7 in which - Ri represents an acyl group of formula
— C-R- C-R
IIII
OO
dans laquelle R représente une chaîne aliphatique hydrocarbonée linéaire contenant 15, 17 ou 19 atomes de carbone, saturée ou comprenant de 1 à 5 doubles liaisons, en position 7, 10 et/ou 13 pour un groupement acyle de 16 atomes de carbone, en position 9, 12 et/ou 15 pour un groupement acyle de 18 atomes de carbone, et en position 5, 8, 10, 14 et/ou 17 pour un groupement acyle de 20 atomes de carbone. - R2 représente un atome d'hydrogène ou un groupement acyle, identique ou différent de Ri de formulein which R represents a linear aliphatic hydrocarbon chain containing 15, 17 or 19 carbon atoms, saturated or comprising from 1 to 5 double bonds, in position 7, 10 and / or 13 for an acyl group of 16 carbon atoms, in position 9, 12 and / or 15 for an acyl group of 18 carbon atoms, and in positions 5, 8, 10, 14 and / or 17 for an acyl group of 20 carbon atoms. - R2 represents a hydrogen atom or an acyl group, identical or different from Ri of formula
—C-R—C-R
1111
O dans laquelle R répond à la définition donnée ci-dessus.O in which R meets the definition given above.
19. Utilisation selon l'une des revendications 11 à 18, caractérisée en ce que la concentration en galactolipide dans la composition précitée est comprise entre 0,001 et 10 %, de préférence entre 0,01 et 5 %, en poids par rapport au poids total de ladite composition. 19. Use according to one of claims 11 to 18, characterized in that the concentration of galactolipid in the abovementioned composition is between 0.001 and 10%, preferably between 0.01 and 5%, by weight relative to the total weight of said composition.
20. Utilisation selon l'une des revendications 11 à 19, caractérisée en ce que ladite composition est formulée de manière appropriée pour une administration topique, en particulier sous forme de crème, de lait, de lotion, gélifiée ou non, ou de pommade, en présence d'un excipient, véhicule ou support cosmétiquement ou pharmaceutiquement acceptable. 20. Use according to one of claims 11 to 19, characterized in that said composition is formulated in an appropriate manner for topical administration, in particular in the form of cream, milk, lotion, gelled or not, or ointment, in the presence of a cosmetically or pharmaceutically acceptable excipient, vehicle or support.
EP96904147A 1995-02-15 1996-02-15 Use of galactosylglycerides and of naturally occurring extracts containing such products in cosmetics, pharmaceutics and particularly dermatology Withdrawn EP0755242A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9501714 1995-02-15
FR9501714A FR2730409B1 (en) 1995-02-15 1995-02-15 USE OF GALACTOLIPIDS, IN PARTICULAR GALACTOSYLGLYCERIDES, AND NATURALLY EXTRACTS CONTAINING THESE PRODUCTS, IN THE COSMETIC, PHARMACEUTICAL AND PARTICULARLY DERMATOLOGICAL AREAS
PCT/FR1996/000250 WO1996025142A1 (en) 1995-02-15 1996-02-15 Use of galactosylglycerides and of naturally occurring extracts containing such products in cosmetics, pharmaceutics and particularly dermatology

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EP0828501B1 (en) * 1995-06-01 2004-09-29 Montana Limited Extract from the leaves of ginkgo biloba
DE19540749A1 (en) * 1995-11-02 1997-05-07 Beiersdorf Ag Cosmetic preparations with an effective content of glycosylglycerides
DE19634020A1 (en) * 1996-08-23 1998-02-26 Beiersdorf Ag Production of glycoglycerolipids, their use as surfactants and cosmetic or dermatological preparations containing such glycoglycerolipids
FR2762783B1 (en) * 1997-05-02 2002-09-13 Roc Sa USE OF OLIGOSACCHARIDES FOR THE TREATMENT OF CONNECTIVE TISSUE AND METHOD OF COSMETIC TREATMENT USING SUCH OLIGOSACCHARIDES
JP2000026228A (en) * 1998-07-10 2000-01-25 Nippon Flour Mills Co Ltd Collagenase inhibitor, moisturizer, and cosmetic or food containing the same
EP1043016B1 (en) 1999-03-30 2014-08-20 Sodic Sa A plant extract based on glycerides,phospholipids and phytosphingolipids, a method for the preparation of this extract and a cosmetic composition containing the same
FR2814071A1 (en) * 2000-09-21 2002-03-22 Oreal GLYCOGLYCERIDE-BASED COMPOSITION AND USES, IN PARTICULAR COSMETIC USE
FR2839447B1 (en) 2002-05-07 2007-05-04 Seppic Sa NOVEL COMPOSITIONS FOR CUTANE USE BASED ON POLYOLS-GLYCOSIDES
JP2005053798A (en) * 2003-08-04 2005-03-03 Nonogawa Shoji Kk Fibronectin production promoter
JP4604556B2 (en) * 2004-05-31 2011-01-05 日油株式会社 Fibronectin production promoter
EP1951762B1 (en) * 2005-10-03 2018-02-07 PINSKY, Mark A. Compositions and methods for improved skin care
KR101531415B1 (en) * 2006-10-17 2015-06-24 바스프 뷰티 케어 솔루션즈 프랑스 에스에이에스 Use of substances to protect fgf-2 or fgf-beta growth factor
DE102006055044A1 (en) * 2006-11-17 2008-05-21 Beiersdorf Ag Cosmetic formulation with glucosylglycerides and urea
WO2008084253A1 (en) * 2007-01-12 2008-07-17 Lipopeptide Ab Use of a galactolipid for wound and ulcer healing
KR102298803B1 (en) * 2014-12-04 2021-09-07 (주)아모레퍼시픽 Composition for moisturizing the skin containing (2S)-1-O-linolenoyl-2-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol
KR102298804B1 (en) * 2014-12-04 2021-09-07 (주)아모레퍼시픽 Composition for moisturizing the skin containing (2S)-1-O-linoleoyl-2-O-linoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol
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