FR3150440A1 - Composition comprising different extracts - Google Patents

Abstract

Composition comprising different extracts The present invention relates to a composition, preferably cosmetic, comprising, in a cosmetically acceptable medium: - at least one extract of Withania somnifera; - at least one extract of Terminalia ferdinandiana; and - at least one extract of Lactobacillus. It also relates to uses and methods using this composition. Figure for the abstract: none

Description

Composition comprising different extracts

The present invention relates to a composition, preferably cosmetic, comprising, in a cosmetically acceptable medium:

- at least one extract of Withania somnifera ;

- at least one extract of Terminalia ferdinandiana ; and

- at least one extract of Lactobacillus .

The skin is a tissue whose cells are joined together and attached to each other. The skin tissue forms an external covering including sebaceous or sweat glands and hair follicles. The skin, and in particular the scalp, are epithelia with continuous renewal. Renewal, or desquamation, is a coordinated and finely regulated process resulting in the elimination of superficial cells, in a way that is imperceptible and invisible.

Human skin is made up of two compartments, namely a superficial compartment, the epidermis, and a deep compartment, the dermis.

The epidermis is conventionally divided into a basal layer of keratinocytes constituting the germinal layer of the epidermis, a so-called spinous layer consisting of several layers of polyhedral cells arranged on the germinal layers, one to three so-called granular layers consisting of flattened cells containing distinct cytoplasmic inclusions, the keratohyalin grains and finally, a set of upper layers called horny layers (or stratum corneum ), consisting of keratinocytes in the terminal stage of their differentiation called corneocytes.

Corneocytes are anucleated cells mainly composed of a fibrous material containing cytokeratins, surrounded by a horny envelope. There is a constant production of new keratinocytes to compensate for the continuous loss of epidermal cells at the level of the horny layer according to a mechanism called desquamation.

However, an imbalance between the production of cells in the basal layer and the rate of desquamation can lead to the formation of scales on the surface of the skin. Similarly, a deficit in terminal differentiation of cells in the stratum corneum , for various reasons, can lead to the formation of large, thick, visible to the naked eye, clusters of cells called "scales", or in other situations, to a thinning of the stratum corneum . This can result in a fragility of the barrier properties of the epidermis, chronic dehydration of the stratum corneum and/or a loss of mechanical elasticity or skin firmness.

Examples of factors that promote this reduction in the quality of the skin's surface include stress, winter, excess sebum or a lack of hydration.

Thus, a fragility of the skin barrier can occur in the presence of external aggressions such as irritants (detergents, acids, bases, oxidants, reducers, concentrated solvents, harmful gases or fumes), thermal or climatic imbalances (cold, dryness, radiation), xenobiotics (undesirable microorganisms, allergens) or internal aggressions such as psychological stress.

Classically used moisturizing active ingredients, such as humectants, moisturizing polymers or fatty substances such as petroleum jelly, temporarily modify the surface properties of the skin. These active ingredients can lead to mechanical softening of the stratum corneum , an increase in its hydration state and/or an improvement in the microrelief of the skin by forming a film on the surface of the skin. Generally, these effects are not persistent over time and only last a few hours. In addition, after cleansing the skin, these active ingredients are eliminated and the mechanical softening effect of the skin, the improvement in the texture of the skin or its optical properties disappear.

Furthermore, during aging, the epidermis undergoes numerous changes which result with age in an alteration of the microrelief, the appearance of wrinkles and fine lines, and a reduction in the firmness of the skin.

In addition, the formulation of environmentally friendly cosmetic products, i.e. those whose design and development take environmental issues into account, is becoming a major concern to help meet global challenges.

It is therefore essential to offer more sustainable compositions and/or preparation processes and/or ingredients to meet these environmental challenges.

There is therefore a need for active ingredients that enable the skin to maintain its role as a barrier function.

There is also a need for active ingredients that improve the surface condition of the skin, which additionally improve firmness properties.

Maintaining or restoring a properly matured horny envelope is essential to preserve a good quality barrier function ensuring protection against external aggressions and lasting hydration of the skin, particularly the epidermis.

Furthermore, it is important to develop new cosmetic compositions with a better carbon footprint, in particular by promoting the use of renewable raw materials and/or with a good index of naturalness and/or of natural origin and more particularly of plant origin, while reducing the use of compounds of petrochemical origin.

The present invention makes it possible to meet these needs.

The invention relates to a composition, preferably cosmetic, comprising, in a cosmetically acceptable medium:

- at least one extract of Withania somnifera ;

- at least one extract of Terminalia ferdinandiana ; and

- at least one extract of Lactobacillus .

Preferably, the composition according to the invention also comprises at least one C-glycoside.

Preferably, the composition according to the invention also comprises ascorbic acid or one of its derivatives.

The invention also relates to a composition, preferably cosmetic, comprising, in a cosmetically acceptable medium:

- at least one extract of Withania somnifera ;

- at least one extract of Terminalia ferdinandiana ;

- at least one extract of Lactobacillus ; and

- at least one C-glycoside, in particular of formula (I), and/or ascorbic acid or one of its derivatives.

The present invention also relates to the use of such a composition for strengthening the barrier function and/or improving the hydration of the skin.

Typically, by strengthening the barrier function, the composition also improves the quality of the skin and/or the radiance of the complexion.

The present invention also relates to the use of such a composition for enhancing the firmness of the skin.

By “skin” is meant all of the skin of the body, and preferably the skin of the face, décolleté, neck, arms and forearms, or even more preferably, the skin of the face (in particular the forehead, nose, cheeks, chin), décolleté and neck.

The present invention also relates to a non-therapeutic cosmetic process for caring for keratin materials, such as the skin, comprising the topical application to these keratin materials of at least one composition according to the invention. More particularly, the invention relates to a cosmetic treatment process as defined above for improving and/or strengthening the barrier function of the skin, in particular for promoting the maintenance of skin having a good quality barrier function.

Withania somnifera extract

The composition according to the invention comprises at least one extract of Withania somnifera . The species Withania somnifera Dunal. was described by the Swedish naturalist Carl von Linné, then reclassified in 1852 by the French botanist Michel Félix Dunal. Its distribution area extends from the Mediterranean rim to China, via Africa, Australia, the Near East, India and Sri Lanka.

Massively cultivated in Indian territory, the species includes different cultivars and varieties selected and produced in different countries, such as South Africa or the United States.

Belonging to the Solanaceae family, Withania somnifera is a small shrub, with a height generally not exceeding 170 cm. The roots are stocky, fleshy with a pale brown bark; the stem is woody at the base, and abundantly branched. Its leaves are oval, subacute and hispid on their lower surface. The self-fertile flowers are grouped by 3 to 6 in small axillary glomeruli and 20 25 7 their calyxes, accrescent after flowering, persist around the fruit in the form of tabs. The fruit is a small, bright red pisiform berry.

Withania somnifera is considered an adaptogenic plant, that is, a plant that increases the body's ability to adapt to different stresses.

Used in traditional African medicine, the root of Withania somnifera has many uses. From Cape Verde to Madagascar, via Somalia or Ethiopia, the roots are used for different purposes.

In Indian Ayurvedic medicine, the alcoholic extract of the root called "Ashwagandha" has been used for centuries as an ingredient in remedies that improve the general physical and mental condition and increase the longevity and vitality of the body.

Beyond traditional medicine, pharmacochemical analyses of Withania somnifera have revealed the presence of a very large number of bioactive compounds called withanolides.

According to the invention, all or part of the plant Withania somnifera can be used as an extract. In practice, the part of the plant used as an extract is chosen from the group comprising the root, the fruit, the flower, the seed, the leaf, the stem.

Particularly preferably, the part of the plant used is the root. It may be fresh, frozen, dried, whole, cut and/or ground root. Advantageously, it is dried and ground root.

The extract of Withania somnifera can in particular be obtained by an extraction process comprising a solid/liquid extraction step of at least part of the plant, followed by a second solid/liquid separation step and finally a third step of recovery of the liquid phase, the solvent used by this process is a mixture of fructose, glycerin and optionally water.

The solvent may contain water, or be devoid of it. However, the presence of water in the solvent has the advantage of making the solvent more fluid, and thus facilitating extraction.

Advantageously, the solvent consists of a mixture of fructose, glycerin and water. Since plant extracts are often intended to be formulated in cosmetic compositions, it is important to avoid extraction solvents comprising salts or acids, of which at least traces will necessarily be found in the extract. Indeed, it is well known that the formulation, in gel or emulsion, of ingredients based on salts beyond a dose of 0.1% is particularly complex. In addition, acids, by lowering the pH of the extracts obtained, have the effect of making the formulation in gel or emulsion difficult. In particular, cosmetic products intended for cutaneous application must have a suitable pH, preferably close to that of the skin (approximately pH 6.5), or neutral. Under these conditions, the use of solvents containing acids therefore requires the addition of excipients, in particular pH regulators.

Furthermore, when the components of this solvent are present in certain molar ratios, the solvent has the properties of a eutectic solvent or NaDES. For the purposes of the invention, the term "eutectic solvent" or "Natural Deep Eutectic Solvent (NaDES)" means a mixture of compounds of natural origin capable of being used as a solvent and having a superstructure based on hydrogen interactions. Briefly, it is possible to determine that a given mixture actually has the superstructure of a NaDES by two-dimensional NMR spectroscopy, in particular by NOESY sequence (for Nuclear Overhauser Effect SpectroscopY). The presence of correlation spots (off-diagonal peaks) reflects a certain spatial proximity between the spins considered, and makes it possible to detect the superstructure of the NaDES. This superstructure and the methods for detecting it are well known to those skilled in the art, and have been precisely described in Dai et al., 2013 (Analytica Chimica Acta, vol. 766 p. 61-68), to which those skilled in the art may refer.

The solvent is in particular liquid at room temperature, which facilitates the implementation of the process leading to the extract of the invention.

In a particular embodiment, the solvent consists of a mixture of fructose, glycerin and water in molar proportions preferably of approximately 1:1:5.

In practice, the solvent used can be produced by mixing fructose and glycerin, or fructose, glycerin and water, in a stirred reactor, until a clear, colorless mixture is obtained. This mixing can be carried out at a temperature between 2°C and 100°C and for 30 minutes to 6 hours, preferably 40°C to 70°C for 1 hour to 2 hours.

The extract is likely to be obtained by a process involving a solid/liquid extraction step.

In particular, it is an extract of the root of Withania somnifera , advantageously dried and crushed.

The solid/liquid extraction can be carried out by different techniques well known to those skilled in the art, such as maceration, re-maceration, digestion, dynamic maceration, decoction, fluid bed extraction, microwave-assisted extraction, ultrasound-assisted extraction, counter-current extraction, percolation, re-percolation, leaching, extraction under reduced pressure, diacolation.

In practice, the plant/solvent mass ratio applied for the extraction step is between 1/99 and 50/50. The extraction step is preferably carried out at a temperature between 2°C and 100°C, more preferably between 20°C and 80°C. The extraction step can be maintained for a few minutes to several days.

In order to optimize the extraction of active compounds while protecting these compounds from oxidation by atmospheric oxygen, the solid/liquid extraction step is advantageously carried out with stirring and/or under a nitrogen atmosphere.

The solid/liquid extraction step is followed by a solid/liquid separation step, the objective being to recover the liquid phase, also called solid/liquid separation filtrate, containing the active material. This separation can be carried out by any technique known in the art, in particular draining, pressing, spinning, centrifugation or filtration. Optionally, the solid/liquid separation step can also be followed by a step of fractionation of the crude extract, which makes it possible to obtain a fraction enriched in one or more families of molecules extracted from the plant. In practice, the fractionation step can be carried out by techniques known in the art, in particular low pressure chromatography or tangential membrane filtration.

Optionally, the liquid/solid separation step or the fractionation step may be followed by a concentration step of the crude extract or fraction, which makes it possible to obtain a concentrate, in liquid or semi-solid form depending on the concentration factor. In practice, the concentration step may be carried out by evaporation under reduced pressure or reverse osmosis.

Preferably, the solid/liquid separation filtrate or concentrate further undergoes one or more clarification steps. To carry out this clarification step, any type of filtration known in the field concerned can be used.

Finally, for the purpose of packaging, the process for obtaining the extract according to the invention may comprise a sterilization step by sterilizing filtration or pasteurization for example. Sterilizing filtration is conventionally carried out by filtering the product through a filter comprising pores with a diameter of approximately 0.22 µm. Preferably, the sterilizing filtration step is the final step of the process. In addition, a microbiological preservative may be added to the extract prior to the sterilization step, preferably a mixture of citric acid and potassium sorbate.

Preferably, the Withania somnifera extract according to the invention is an extract of Withania somnifera root . It is notably marketed by Gattefosse under the name “EnergiNius”, and is in the form of a mixture of Withania somnifera root extract at 7% by weight relative to the total weight of the mixture, 46.7% by weight of fructose, 23% by weight of glycerin, 23% by weight of water, 0.2% by weight of potassium sorbate 0.2% and 0.1% by weight of citric acid.

Preferably, the extract of Withania somnifera is present in the composition according to the invention in a content of between 0.001% and 10% by weight relative to the total weight of the composition, preferably between 0.01% and 5% by weight, preferably between 0.05% and 3% by weight.

Extract from Terminalia ferdinandiana

The composition according to the invention comprises at least one extract of Terminalia ferdinandiana .

Terminalia ferdinandiana , also known as Kakadu plum, Gubinge or Murunga (or Billy Goat Plum or Kakadu plum in English), is a flowering plant in the family Combretaceae , native to Australia where it is widely distributed in woodlands.

Its fruit has the highest vitamin C content (fifty times higher than that of an orange) of all fruits. It is also very rich in phenolic acids (antioxidants).

It is a slender, small to medium-sized tree that can reach up to 14 m in height, with scaly bark mottled with cream, green, grey, orange, yellow and simple, opposite, lanceolate, grey-green leaves. The flowers are small, creamy white, fragrant and located in the axils of the leaves towards the end of the branches. Flowering occurs from September to December (austral spring and summer).

The fruit is green-yellow, about 2 centimeters long and 1 centimeter in diameter, about the size of an almond with a short point at the end, and contains a large seed. It ripens from March.

According to the invention, all or part of the Terminalia ferdinandiana plant can be used as an extract. In practice, the part of the plant used as an extract is chosen from the group comprising the root, the fruit, the flower, the seed, the leaf, the stem.

Particularly preferably, the part of the plant used is the fruit. It can be fresh, frozen, dried, whole, cut and/or crushed fruit. Preferably, the fruit is whole (i.e. with the seeds).

The Terminalia ferdinandiana extract can in particular be obtained by a cold extraction process of at least part of the plant, in particular under pressure. Then the process can comprise a sterilization step, for example by sterilizing filtration. Finally, the extract obtained can be mixed with a solvent. The solvent is preferably a glycol such as glycerin, propylene glycol or pentylene glycol. Preferably, the solvent is pentylene glycol.

Preferably, the Terminalia ferdinandiana extract according to the invention is a Terminalia ferdinandiana fruit extract . It is notably marketed by Biocosmethic under the name “Kalmethic”, and is in the form of a mixture of 97% by weight of Terminalia ferdinandiana fruit extract relative to the total weight of the mixture and 3% of pentylene glycol.

Preferably, the Terminalia ferdinandiana extract is present in the composition according to the invention in a content of between 0.01% and 3% by weight relative to the total weight of the composition, preferably between 0.02% and 1% by weight, preferably between 0.03% and 1% by weight.

Lactobacillus extract

The composition according to the invention comprises at least one Lactobacillus extract.

Preferably, the Lactobacillus extract is an extract of Lactobacillus plantarum ( L. plantarum ) . Preferably, the Lactobacillus extract is an extract of L. plantarum HEAL19 (DSM 15313). This extract is notably marketed by Probi AB.

L. plantarum HEAL19 (DSM 15313) is a lactic acid bacterial strain selected on the basis of its high tannase activity. This product is used as a probiotic.

Preferably, the Lactobacillus extract is formulated with a prebiotic, preferably a maltodextrin.

Preferably, the Lactobacillus extract is obtained by the following steps: fermentation of L. plantarum HEAL19 (DSM 15313); then centrifugation and recovery of the precipitate; passage of the precipitate in a granulator then addition of a cryoprotectant and lyophilization; mixing with a maltodextrin and water; pasteurization; then drying to remove the water and obtain a powder.

The Lactobacillus extract is marketed by Symrise under the name “Symreboot L19”, and is in the form of a mixture of 80% by weight of L. plantarum HEAL19 extract (DSM 15313) relative to the total weight of the mixture and 20% of maltodextrin.

Preferably, the Lactobacillus extract is present in the composition according to the invention in a content of between 0.001% and 1% by weight relative to the total weight of the composition, preferably between 0.01% and 0.8% by weight, preferably between 0.05% and 0.6% by weight.

C-glycoside

Preferably, the composition according to the invention also comprises at least one C-glycoside.

The C-glycoside (or C-glycoside derivative) according to the invention is preferably of the following general formula (I):

(I)

in which:

- R represents a linear alkyl radical, saturated in C1 to C10, in particular in C1 to C4, and which can optionally be substituted by at least one radical chosen from OH, COOH or COOR"2, with R"2 being a saturated C1-C4 alkyl radical;

- X represents a radical chosen from -CO-, -CH(OH)-, -CH(NH ₂ )-, -CH(NHCH2CH2CH2OH)-, -CH(NHPh)- and -CH(CH3)- and in particular a radical -CO-, -CH(OH)- or -CH(NH2)- and preferentially a group –CH(OH)-;

- S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of L and/or D series, said mono- or polysaccharide possibly being substituted by a hydroxyl group which is necessarily free, and optionally one or more amine function(s) which are optionally protected, and

- the S-CH2-X bond represents a C-anomeric bond, which can be α or β,

as well as their physiologically acceptable salts, their solvates such as hydrates and their optical and geometric isomers.

The C-glycosides of formula I useful for implementing the invention are in particular those for which R denotes a saturated linear alkyl radical in C1 to C6, in particular in C1 to C4, preferentially in C1 to C2 and more preferentially a methyl radical.

Among the alkyl groups suitable for implementing the invention, mention may in particular be made of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl and cyclohexyl groups.

It is also possible to use a C-glycoside derivative corresponding to formula (I) for which S can represent a monosaccharide or a polysaccharide containing up to 6 sugar units, in pyranose and/or furanose form and of series L and/or D, said mono- or polysaccharide having at least one hydroxyl function which must be free and/or optionally one or more amine functions which must be protected, X and R moreover retaining all of the definitions given above.

Advantageously, a monosaccharide of the invention may be chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose.

More particularly, a polysaccharide of the invention containing up to 6 sugar units may be chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid chosen from D-iduronic acid or D-glucuronic acid with a hexosamine chosen from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine, N-acetyl-D-glucosamine, an oligosaccharide containing at least one xylose which may advantageously be chosen from xylobiose, methyl-β-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose which is composed of two xylose molecules linked by a 1-4 bond.

More particularly, S may represent a monosaccharide chosen from D-glucose, D-xylose, L-fucose, D-galactose, D-maltose and in particular D-xylose.

Preferably, a C-glycoside derivative corresponding to formula (I) is used for which:

- R represents an unsubstituted linear alkyl radical in C1 to C4, in particular in C1 to C2, in particular methyl;

- S represents a monosaccharide as described above, preferably D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose;

- X represents a radical chosen from -CO-, -CH(OH)-, -CH(NH ₂ )-, and preferably a –CH(OH)- group.

Acceptable salts for non-therapeutic use of the compounds described in the present invention include conventional non-toxic salts of said compounds such as those formed from organic or inorganic acids. By way of example, mention may be made of salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, boric acid. Mention may also be made of salts of organic acids, which may comprise one or more carboxylic, sulfonic or phosphonic acid groups. These may be linear, branched or cyclic aliphatic acids or aromatic acids. These acids may further comprise one or more heteroatoms chosen from O and N, for example in the form of hydroxyl groups. Examples include propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.

When the compound of formula (I) comprises an acid group, the neutralization of the acid group(s) may be carried out by a mineral base, such as LiOH, NaOH, KOH, Ca(OH)2, NH4OH, Mg(OH)2 or Zn(OH)2; or by an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may therefore comprise, for example, one or more alcohol functions; mention may in particular be made of 2-amino-2-methyl-propanol, triethanolamine, 2-dimethylamino-propanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol. Mention may also be made of lysine or 3-(dimethylamino)propylamine.

Acceptable solvates for the compounds described in the present invention include conventional solvates such as those formed during the last step of preparation of said compounds due to the presence of solvents. As an example, solvates due to the presence of water or linear or branched alcohols such as ethanol or isopropanol may be mentioned.

Among the C-glycoside derivatives of formula (I), used according to the invention, the following are particularly considered:

1. C-β-D-xylopyranoside-n-propane-2-one;

2. C-α-D-xylopyranoside-n-propane-2-one;

3. 1-[2-(3-hydroxy-propylamino)-propyl]-C- β -D-xylopyranose;

4. 1-[2-(3-hydroxy-propylamino)-propyl]-C-α-D-xylopyranose;

5. C-β-D-xylopyranoside-2-hydroxy-propane;

6. C-α-D-xylopyranoside-2-hydroxy-propane;

7. C-β-D-xylopyranoside-2-amino-propane;

8. C-α-D-xylopyranoside-2-amino-propane;

9. C-β-D-xylopyranoside-2-phenylamino-propane;

10. C-α-D-xylopyranoside-2-phenylamino-propane;

11. 3-methyl-4-(C-β-D-xylopyranoside)-butyric acid ethyl ester;

12. 3-methyl-4-(C-α-D-xylopyranoside)-butyric acid ethyl ester;

13. 6-(C-β-D-xylopyranoside)-5-keto-hexanoic acid;

14. 6-(C-α-D-xylopyranoside)-5-keto-hexanoic acid;

15. 6-(C-β-D-xylopyranoside)-5-hydroxy-hexanoic acid;

16. 6-(C-α-D-xylopyranoside)-5-hydroxy-hexanoic acid;

17. 6-(C-β-D-xylopyranoside)-5-amino-hexanoic acid;

18. 6-(C-α-D-xylopyranoside)-5-amino-hexanoic acid;

19. 6-(C-β-D-xylopyranoside)-5-phenylamino-hexanoic acid;

20. 6-(C-α-D-xylopyranoside)-5-phenylamino-hexanoic acid;

21. 1-(C-β-D-xylopyranoside)-hexane-2,6-diol;

22. 1-(C-α-D-xylopyranoside)-hexane-2,6-diol;

23. 5-(C-β-D-xylopyranoside)-4-keto-pentanoic acid;

24. 5-(C-α-D-xylopyranoside)-4-keto-pentanoic acid;

25. 5-(C-β-D-xylopyranoside)-4-hydroxy-pentanoic acid;

26. 5-(C-α-D-xylopyranoside)-4-hydroxy-pentanoic acid;

27. 5-(C-β-D-xylopyranoside)-4-amino-pentanoic acid;

28. 5-(C-α-D-xylopyranoside)-4-amino-pentanoic acid;

29. 5-(C-β-D-xylopyranoside)-4-phenylamino-pentanoic acid;

30. 5-(C-α-D-xylopyranoside)-4-phenylamino-pentanoic acid;

31. 1-(C-β-D-xylopyranoside)-pentan-2,5-diol;

32. 1-(C-α-D-xylopyranoside)-pentan-2,5-diol;

33. 1-(C-β-D-fucopyranoside)-propane-2-one;

34. 1-(C-α-D-fucopyranoside)-propane-2-one;

35. 1-(C-β-L-fucopyranoside)-propane-2-one;

36. 1-(C-α-L-fucopyranoside)-propane-2-one;

37. 1-(C-β-D-fucopyranoside)-2-hydroxy-propane;

38. 1-(C-α-D-fucopyranoside)-2-hydroxy-propane;

39. 1-(C-β-L-fucopyranoside)-2-hydroxy-propane;

40. 1-(C-α-L-fucopyranoside)-2-hydroxy-propane;

41. 1-(C-β-D-fucopyranoside)-2-amino-propane;

42. 1-(C-α-D-fucopyranoside)-2-amino-propane;

43. 1-(C-β-L-fucopyranoside)-2-amino-propane;

44. 1-(C-α-L-fucopyranoside)-2-amino-propane;

45. 1-(C-β-D-fucopyranoside)-2-phenylamino-propane;

46. 1-(C-α-D-fucopyranoside)-2-phenylamino-propane;

47. 1-(C-β-L-fucopyranoside)-2-phenylamino-propane;

48. 1-(C-α-L-fucopyranoside)-2-phenylamino-propane;

49. 3-methyl-4-(C-β-D-fucopyranoside)-butyric acid ethyl ester;

50. 3-methyl-4-(C-α-D-fucopyranoside)-butyric acid ethyl ester;

51. 3-methyl-4-(C-β-L-fucopyranoside)-butyric acid ethyl ester;

52. 3-methyl-4-(C-α-L-fucopyranoside)-butyric acid ethyl ester;

53. 6-(C-β-D-fucopyranoside)-5-keto-hexanoic acid;

54. 6-(C-α-D-fucopyranoside)-5-keto-hexanoic acid;

55. 6-(C-β-L-fucopyranoside)-5-keto-hexanoic acid;

56. 6-(C-α-L-fucopyranoside)-5-keto-hexanoic acid;

57. 6-(C-β-D-fucopyranoside)-5-hydroxy-hexanoic acid;

58. 6-(C-α-D-fucopyranoside)-5-hydroxy-hexanoic acid;

59. 6-(C-β-L-fucopyranoside)-5-hydroxy-hexanoic acid;

60. 6-(C-α-L-fucopyranoside)-5-hydroxy-hexanoic acid;

61. 6-(C-β-D-fucopyranoside)-5-amino-hexanoic acid;

62. 6-(C-α-D-fucopyranoside)-5-amino-hexanoic acid;

63. 6-(C-β-L-fucopyranoside)-5-amino-hexanoic acid;

64. 6-(C-α-L-fucopyranoside)-5-amino-hexanoic acid;

65. 1-(C-β-D-fucopyranoside)-hexane-2,6-diol;

66. 1-(C-α-D-fucopyranoside)-hexane-2,6-diol;

67. 1-(C-β-L-fucopyranoside)-hexane-2,6-diol;

68. 1-(C-α-L-fucopyranoside)-hexane-2,6-diol;

69. 5-(C-β-D-fucopyranoside)-4-keto-pentanoic acid;

70. 5-(C-α-D-fucopyranoside)-4-keto-pentanoic acid;

71. 5-(C-β-L-fucopyranoside)-hexane-2,6-diol)-4-keto-pentanoic acid;

72. 5-(C-α-L-fucopyranoside)-hexane-2,6-diol)-4-keto-pentanoic acid;

73. 5-(C-β-D-fucopyranoside)-4-hydroxy-pentanoic acid;

74. 5-(C-α-D-fucopyranoside)-4-hydroxy-pentanoic acid;

75. 5-(C-β-L-fucopyranoside)-4-hydroxy-pentanoic acid;

76. 5-(C-α-L-fucopyranoside)-4-hydroxy-pentanoic acid;

77. 5-(C-β-D-fucopyranoside)-4-amino-pentanoic acid;

78. 5-(C-α-D-fucopyranoside)-4-amino-pentanoic acid

79. 5-(C-β-L-fucopyranoside)-4-amino-pentanoic acid;

80. 5-(C-α-L-fucopyranoside)-4-amino-pentanoic acid;

81. 1-(C-β-D-fucopyranoside)-pentane-2,5-diol;

82. 1-(C-α-D-fucopyranoside)-pentane-2,5-diol;

83. 1-(C-β-L-fucopyranoside)-pentane-2,5-diol;

84. 1-(C-α-L-fucopyranoside)-pentane-2,5-diol;

85. 1-(C-β-D-glucopyranosyl)-2-hydroxy-propane;

86. 1-(C-α-D-glucopyranosyl)-2-hydroxy-propane;

87. 1-(C-β-D-glucopyranosyl)-2-amino-propane;

88. 1-(C-α-D-glucopyranosyl)-2-amino-propane;

89. 1-(C-β-D-glucopyranosyl)-2-phenylamino-propane;

90. 1-(C-α-D-glucopyranosyl)-2-phenylamino-propane;

91. 3-methyl-4-(C-β-D-glucopyranosyl)-butyric acid ethyl ester;

92. 3-methyl-4-(C-α-D-glucopyranosyl)-butyric acid ethyl ester;

93. 6-(C-β-D-glucopyranosyl)-5-keto-hexanoic acid;

94. 6-(C-α-D-glucopyranosyl)-5-keto-hexanoic acid;

95. 6-(C-β-D-glucopyranosyl)-5-hydroxy-hexanoic acid;

96. 6-(C-α-D-glucopyranosyl)-5-hydroxy-hexanoic acid;

97. 6-(C-β-D-glucopyranosyl)-5-amino-hexanoic acid;

98. 6-(C-α-D-glucopyranosyl)-5-amino-hexanoic acid;

99. 6-(C-β-D-glucopyranosyl)-5-phenylamino-hexanoic acid;

100. 6-(C-α-D-glucopyranosyl)-5-phenylamino-hexanoic acid;

101. 1-(C-β-D-glucopyranosyl)-hexane-2,6-diol;

102. 1-(C-α-D-glucopyranosyl)-hexane-2,6-diol;

103. 6-(C-β-D-glucopyranosyl)-5-keto-pentanoic acid;

104. 6-(C-α-D-glucopyranosyl)-5-keto-pentanoic acid;

105. 6-(C-β-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

106. 6-(C-α-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

107. 6-(C-β-D-glucopyranosyl)-5-amino-pentanoic acid;

108. 6-(C-α-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

109. 6-(C-β-D-glucopyranosyl)-5-phenylamino-pentanoic acid;

110. 6-(C-α-D-glucopyranosyl)-5-phenylamino-pentanoic acid;

111. 1-(C-β-D-glucopyranosyl)-pentan-2,5-diol;

112. 1-(C-α-D-glucopyranosyl)-pentan-2,5-diol;

113. 1-(C-β-D-galactopyranosyl)-2-hydroxy-propane;

114. 1-(C-α−D-galactopyranosyl)-2-hydroxy-propane;

115. 1-(C-β-D-galactopyranosyl)-2-amino-propane;

116. 1-(C-α-D-galactopyranosyl)-2-amino-propane;

117. 1-(C-β-D-galactopyranosyl)-2-phenylamino-propane;

118. 1-(C-α-D-galactopyranosyl)-2-phenylamino-propane;

119. 3-methyl-4-(β-D-galactopyranosyl)-butyric acid ethyl ester;

120. 3-methyl-4-(α-D-galactopyranosyl)-butyric acid ethyl ester;

121. 6-(C-β-D-galactopyranosyl)-5-keto-hexanoic acid;

122. 6-(C-α-D-galactopyranosyl)-5-keto-hexanoic acid;

123. 6-(C-β-D-galactopyranosyl)-5-hydroxy-hexanoic acid;

124. 6-(C-α-D-galactopyranosyl)-5-hydroxy-hexanoic acid;

125. 6-(C-β-D-galactopyranosyl)-5-amino-hexanoic acid;

126. 6-(C-α-D-galactopyranosyl)-5-amino-hexanoic acid;

127. 6-(C-β-D-galactopyranosyl)5-phenylamino-hexanoic acid;

128. 6-(C-α-D-galactopyranosyl)5-phenylamino-hexanoic acid;

129. 1-(C-β-D-galactopyranosyl)-hexane-2,6-diol;

130. 1-(C-α-D-galactopyranosyl)-hexane-2,6-diol;

131. 6-(C-β-D-galactopyranosyl)-5-keto-pentanoic acid;

132. 6-(C-α-D-galactopyranosyl)-5-keto-pentanoic acid;

133. 6-(C-β-D-galactopyranosyl)-5-hydroxy-pentanoic acid;

134. 6-(C-α-D-galactopyranosyl)-5-hydroxy-pentanoic acid;

135. 6-(C-β-D-galactopyranosyl)-5-amino-pentanoic acid;

136. 6-(C-α-D-galactopyranosyl)-5-amino-pentanoic acid;

137. 6-(C-β-D-galactopyranosyl)-5-phenylamino-pentanoic acid;

138. 6-(C-α-D-galactopyranosyl)-5-phenylamino-pentanoic acid;

139. 1-(C-β-D-galactopyranosyl)-pentan-2,6-diol;

140. 1-(C-α-D-galactopyranosyl)-pentan-2,6-diol;

141. 1-(C-β-D-fucofuranosyl)-propane-2-one;

142. 1-(C-α-D-fucofuranosyl)-propane-2-one;

143. 1-(C-β-L-fucofuranosyl)-propane-2-one;

144. 1-(C-α-L-fucofuranosyl)-propane-2-one;

145. 3'-(acetamido-C-β-D-glucopyranosyl)-propan-2'-one;

146. 3'-(acetamido-C-α-D-glucopyranosyl)-propan-2'-one;

147. 1-(acetamido-C-β-D-glucopyranosyl)-2-hydroxyl-propane;

148. 1-(acetamido-C-β-D-glucopyranosyl)-2-amino-propane;

149. 1-(acetamido-C-β-D-glucopyranosyl)-2-phenylamino-propane;

150. 1-(acetamido-C-α-D-glucopyranosyl)-2-phenylamino-propane;

151. 3-methyl-4-(acetamido-C-β-D-glucopyranosyl)-ethyl ester

butyric;

152. 3-methyl-4-(acetamido-C-α-D-glucopyranosyl)-ethyl ester

butyric;

153. 6-(acetamido-C-β-D-glucopyranosyl)-5-keto-hexanoic acid;

154. 6-(acetamido-C-α-D-glucopyranosyl)-5-keto-hexanoic acid;

155. 6-(acetamido-C-β-D-glucopyranosyl)-5-hydroxy-hexanoic acid;

156. 6-(acetamido-C-α-D-glucopyranosyl)-5-hydroxy-hexanoic acid;

157. 6-(acetamido-C-β-D-glucopyranosyl)-5-amino-hexanoic acid;

158. 6-(acetamido-C-α-D-glucopyranosyl)-5-amino-hexanoic acid;

159. 6-(acetamido-C-β-D-glucopyranosyl)-5-phenylamino-hexanoic acid;

160. 6-(acetamido-C-α-D-glucopyranosyl)-5-phenylamino-hexanoic acid;

161. 1-(acetamido-C-β-D-glucopyranosyl)-hexane-2,6-diol;

162. 1-(acetamido-C-α-D-glucopyranosyl)-hexane-2,6-diol;

163. 6-(acetamido-C-β-D-glucopyranosyl)-5-keto-pentanoic acid;

164. 6-(acetamido-C-α-D-glucopyranosyl)-5-keto-pentanoic acid;

165. 6-(acetamido-C-β-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

166. 6-(acetamido-C-α-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

167. 6-(acetamido-C-β-D-glucopyranosyl)-5-amino-pentanoic acid;

168. 6-(acetamido-C-α-D-glucopyranosyl)-5-amino-pentanoic acid;

169. 6-(acetamido-C-β-D-glucopyranosyl)-5-phenylamino-pentanoic acid;

170. 6-(acetamido-C-α-D-glucopyranosyl)-5-phenylamino-pentanoic acid;

171. 1-(acetamido-C-β-D-glucopyranosyl)-pentane-2,5-diol;

172. 1-(acetamido-C-α-D-glucopyranosyl)-pentane-2,5-diol.

By way of illustration and non-limiting example of the C-glycoside derivatives which are more particularly suitable for the invention, the following derivatives may in particular be mentioned:

- C-β-D-xylopyranoside-n-propane-2-one,

- C-α-D-xylopyranoside-n-propan-2-one,

- C-β-D-xylopyranoside-2-hydroxy-propane,

- C-α-D-xylopyranoside-2-hydroxy-propane,

- 1-(C-β-D-fucopyranoside)-propane-2-one,

- 1-(C-α-D-fucopyranoside)-propane-2-one,

- 1-(C-β-L-fucopyranoside)-propane-2-one,

- 1-(C-α-L-fucopyranoside)-propan-2-one,

- 1-(C-β-D-fucopyranoside)-2-hydroxy-propane,

- 1-(C-α-D-fucopyranoside)-2-hydroxy-propane,

- 1-(C-β-L-fucopyranoside)-2-hydroxy-propane,

- 1-(C-α-L-fucopyranoside)-2-hydroxy-propane,

- 1-(C-β-D-Glucopyranosyl)-2-hydroxyl-propane,

- 1-(C-α-D-Glucopyranosyl)-2-hydroxyl-propane,

- 1-(C-β-D-galactopyranosyl)-2-hydroxyl-propane,

- 1-(C-α-D-galactopyranosyl)-2-hydroxyl-propane

- 1-(C-β-D-fucofuranosyl)-propan-2-one,

- 1-(C-α-D-fucofuranosyl)-propan-2-one

- 1-(C-β-L-fucofuranosyl)-propan-2-one,

- 1-(C-α-L-fucofuranosyl)-propan-2-one,

- C-β-D-maltopyranoside-n-propan-2-one,

- C-α-D-maltopyranoside-n-propan-2-one

- C-β-D-maltopyranoside-2-hydroxy-propane,

- C-α-D-maltopyranoside-2-hydroxy-propane, their isomers or their mixtures.

Preferably, C-beta-D-xylopyranoside-2-hydroxy-propane or C-alpha-D-xylopyranoside-2-hydroxy-propane is used, and more preferably C-beta-D-xylopyranoside-2-hydroxy-propane.

Preferably, a C-glycoside of formula (I) suitable for the invention may advantageously be C-beta-D-xylopyranoside-2-hydroxy-propane, the INCI name of which is HYDROXYPROPYL TETRAHYDROPYRANTRIOL. This active ingredient may be marketed in the form of a mixture comprising, for example, 30% by weight of active material of hydroxypropyl tetrahydropyrantriol relative to the total weight of the mixture in 60% by weight of water and 40% of propylene glycol.

Preferably, the composition according to the invention comprises at least one C-glycoside derivative in a content of 1% to 21% by weight of active material relative to the total weight of the composition, preferably from 2% to 9% by weight of active material, and more particularly from 3% to 7% by weight of active material.

Ascorbic acid and its derivatives

Preferably, the composition according to the invention also comprises ascorbic acid or one of its derivatives.

Ascorbic acid for the purposes of the invention preferably corresponds to L-ascorbic acid, or vitamin C. It has the structure of formula (II):

(II)

By “ascorbic acid derivative” is preferably meant a compound chosen from 5,6-di-O-dimethylsilylascorbate (notably sold by the company Exsymol under the reference PRO-AA), the potassium salt of DL-alpha-tocopheryl-DL-ascorbyl-phosphate also called Potassium Ascorbyl Tocopheryl Phosphate (sold by the company SEPPIC under the reference SEPIVITAL EPC), magnesium ascorbyl phosphate, sodium ascorbyl phosphate (sold by the company DSM under the reference Stay-C 50), disodium ascorbyl sulfate, sulfinyl-L-ascorbic acid, glucopyranosyl-L-ascorbic acid and ascorbyl glucoside.

Preferably, the ascorbic acid derivative is ascorbyl glucoside.

By "ascorbyl glucoside" is meant the condensation product of glucose, in D form, i.e. in the form of α or β glucopyranose or α or β furanose, or in L form, with ascorbic acid, preferably in L form. Preferably, the ascorbyl glucoside is 2-O-α-D-glucopyranoside of L-ascorbic acid, available in particular from the company HAYASHIBARA.

Preferably, the composition according to the invention comprises ascorbic acid, preferably L-ascorbic acid, or ascorbyl glucoside.

Preferably, the composition according to the invention comprises from 1% to 15% by weight of ascorbic acid or one of its derivatives relative to the total weight of the composition, preferably from 1% to 10% by weight of active material, and more particularly from 1.5% to 5% by weight of active material.

Cosmetically acceptable medium

The composition according to the invention comprises a cosmetically acceptable medium.

By “cosmetically acceptable medium” we mean a medium compatible with the skin, mucous membranes and/or appendages.

The compositions according to the invention may be in all the galenic forms conventionally used for topical application and in particular in the form of aqueous, hydroalcoholic solutions, oil-in-water (O/W) or water-in-oil (W/O) or multiple (triple: W/O/W or O/W/O) emulsions, aqueous gels, or dispersions of a fatty phase in an aqueous phase using spherules, these spherules possibly being lipid vesicles of ionic and/or non-ionic type (liposomes, niosomes, oleosomes). These compositions are prepared according to the usual methods.

The compositions according to the invention may also be in anhydrous form, such as for example in the form of an oil. The term "anhydrous composition" means a composition containing less than 1% by weight of water, or even less than 0.5% of water, and in particular free of water, the water not being added during the preparation of the composition but corresponding to the residual water provided by the mixed ingredients.

Advantageously, the compositions according to the invention are in the form of a gel, or emulsion, powder or paste.

In addition, the composition according to the invention may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a foaming gel, a treatment, a tonic or a mousse. It may optionally be applied to the skin in the form of an aerosol. It may also be in solid form, for example in the form of a stick.

When the composition used according to the invention comprises an oily phase, the latter preferably contains at least one oil. It may also contain other fatty substances.

As oils which can be used in the composition of the invention, we can cite for example:

- hydrocarbon oils of animal origin, such as perhydrosqualene;

- hydrocarbon oils of plant origin, such as liquid triglycerides of fatty acids containing 4 to 10 carbon atoms such as triglycerides of heptanoic or octanoic acids or, for example, sunflower, corn, soybean, pumpkin, grape seed, sesame, hazelnut, apricot, macadamia, arara, sunflower, castor, avocado oils, triglycerides of caprylic/capric acids such as those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company CREMER OLEO, jojoba oil, shea butter oil;

- synthetic esters and ethers, in particular of fatty acids, such as oils of formulae RCOOR2 and ROR2 in which R represents the residue of a fatty acid containing from 8 to 29 carbon atoms, and R2 represents a hydrocarbon chain, branched or not, containing from 3 to 30 carbon atoms, such as for example Purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate; hydroxyl esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, fatty alcohol heptanoates, octanoates, decanoates; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate;

- linear or branched hydrocarbons, of mineral or synthetic origin, such as paraffin oils, volatile or not, and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as parleam oil;

- fatty alcohols having 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol;

- partially hydrocarbon and/or silicone fluorinated oils such as those described in document JP-A-2-295912;

- silicone oils such as volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, pendant or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenylated silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyldimethicones, diphenylmethyldiphenyl trisiloxanes, 2-phenylethyltrimethylsiloxysilicates, and polymethylphenylsiloxanes;

- and their mixtures.

In the list of oils cited above, hydrocarbon oil means any oil containing mainly carbon and hydrogen atoms, and possibly ester, ether, fluorine, carboxylic acid and/or alcohol groups.

Other fatty substances that may be present in the oily phase are, for example, fatty acids containing 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, carnauba wax or candelilla wax, paraffin wax, lignite wax or microcrystalline wax, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes; silicone resins such as trifluoromethyl-C1-4-alkyldimethicone and trifluoropropyldimethicone; and silicone elastomers such as the products marketed under the names KSG by the company Shin-Etsu, under the names "Trefil", "BY29" or "EPSX" by the company Dow Corning or under the names "Gransil" by the company Grant Industries.

These fatty substances can be chosen in a variety of ways by those skilled in the art in order to prepare a composition having the desired properties, for example consistency or texture.

The composition may comprise at least one emulsifier, in particular chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are chosen appropriately according to the emulsion to be obtained (water-in-oil or oil-in-water). The emulsifier and the co-emulsifier are generally present in the composition, in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition.

The composition according to the invention may also contain ingredients usual in the cosmetic field, such as hydrophilic or lipophilic gelling agents, preservatives, perfumes, fillers, waxes, pasty fatty substances, sun protection filters or UV filters, odor absorbers, coloring materials, basic agents, acids, sequestering agents, polyols, nonionic, anionic or cationic surfactants.

The composition according to the invention may of course include other barrier effect active ingredients and/or other moisturizing active ingredients different from the extracts of the invention.

The quantities of these different ingredients are those conventionally used in the field considered, and for example from 0.01 to 20% of the total weight of the composition. These ingredients, depending on their nature, can be introduced into the fatty phase, into the aqueous phase and/or into the lipid vesicles.

The compositions according to the invention may additionally comprise at least one aqueous phase. The aqueous phase contains water, and optionally other organic solvents soluble or miscible in water. An aqueous phase suitable for the invention may comprise, for example, a water chosen from a natural spring water, such as La Roche-Posay water, Vittel water, or Vichy waters, or a floral water.

Of course, those skilled in the art will take care to choose the possible compound(s) to be added to the composition according to the invention and their quantities in such a way that the advantageous properties intrinsically attached to the composition in accordance with the invention are not, or not substantially, altered by the envisaged addition.

As previously indicated, the present invention also relates to the use of such a composition for strengthening the barrier function and/or improving the hydration of the skin.

Typically, by strengthening the barrier function, the composition also improves the quality of the skin and/or the radiance of the complexion.

The present invention also relates to the use of such a composition for enhancing the firmness of the skin.

The present invention also relates to a non-therapeutic cosmetic process for caring for keratin materials, such as the skin, comprising the topical application to these keratin materials of at least one composition according to the invention. More particularly, the invention relates to a cosmetic treatment process as defined above for improving and/or strengthening the barrier function of the skin, in particular for promoting the maintenance of skin having a good quality barrier function.

The method according to the invention may comprise a repeated application, for example 1 to 3 times daily over a day or several days, preferably 1 to 2 times per day, and particularly over a prolonged period of at least 4, or even 4 to 15 weeks, with, where appropriate, one or more periods of interruption. According to one embodiment, the cosmetic treatment method according to the invention may comprise a single application. Preferably, a method according to the invention will comprise the topical application of a composition according to the invention to the skin, in particular to the skin of the face.

Concrete, but in no way limiting, examples illustrating the invention will now be given.

Examples

I- Effects of a composition according to the invention on the barrier function

Example 1: Claudin 1

Claudins are major constituents of tight junction complexes that regulate epithelial permeability.

Materials & Methods:

Keratinocytes were seeded in 96-well plates and cultured in culture medium for 24 hours. The medium was then replaced with a test medium containing or not (control) the tested compounds, the combinations or the reference (1.5 mM CaCl2 for Claudin-1) and the cells were incubated for 72 hours. All experimental conditions were performed in n=3. At the end of the incubation, the cells were rinsed with PBS solution, fixed and permeabilized. The cells were then labeled using a specific primary antibody (Anti-claudin-1, Santa Cruz #SC-81796). The primary antibody was then revealed using an appropriate fluorescent secondary antibody (GAM-Alexa488, Invitrogen #A11001) and cell nuclei were stained using Hoechst 33258 solution (bisbenzimide, Sigma, #B1155) in parallel. Image acquisition was performed with a high-resolution imaging system, the INCell Analyzer™2200 automated microscope (GE Healthcare). For each well, 5 images were taken (x20 objective). Labeling was quantified by measuring the fluorescence intensity of each protein normalized to the total number of nuclei identified by Hoechst 33258 staining (Digital Data Integration with Developer Toolbox 1.5, GE Healthcare software).

Results :

The trio according to the invention tested at low concentration (i.e. “Trio” of 0.017% Symreboot L19, 0.0335% Energinius and 0.0135% Kalmethic), with 0.067% ascorbyl glucoside (Vit CG) and with 0.167% hydroxypropyl tetrahydropyrantriol (HT) diluted to 35%, significantly stimulated the expression of Claudin-1 while none of these ingredients showed a significant effect when tested alone. Furthermore, the effect of the combination was clearly greater than the sum of the individual effects, thus demonstrating a significantly greater effect between hydroxypropyl tetrahydropyrantriol, ascorbyl glucoside and the trio.

Claudin-1 %Control Control 100 1.5mM CaCl2 510 0.1670% HT (diluted to 35%, or 0.05845% active ingredient) 165 0.0670% Vit CG 57 0.0135% Terminalia ferdinandiana extract (Kalmethic from Biocosmethic, i.e. 0.0130% active extract matter) 86 0.0170% Lactobacillus extract (Symreboot L19 from Symrise, i.e. 0.0034% active extract matter) 189 0.0335% Extract of Withania somnifera (EnergiNius de Gattefosse, i.e. 0.00235% active extract matter) 98 Trio 111 Trio + Vit CG 78 Trio + Vit CG + HT 406

Example 2: ZO-1 Materials & Methods:

CaCl2 tested at 1.5 mM significantly stimulated the expression of all markers involved in keratinocyte differentiation (Involucrin, Loricrin, TGK and Filaggrin) and the expression of key markers involved in tight junctions (Claudin-1 and ZO-1). This prodifferentiating effect of CaCl2 was expected and validates the assays.

Results :

As shown in the tables below, the trio according to the invention stimulated ZO-1 expression while all compounds, even in combination two by two, did not do so.

ZO-1 %Control Significance Control 100 1.5mM CaCl2 121 * 0.0130% active matter Terminalia ferdinandiana extract (Kalmethic from Biocosmethic) 103 ns 0.0034% active matter Lactobacillus Extract (Symreboot L19 from Symrise) 106 ns 0.0023% active matter Extract of Withania somnifera (EnergiNius of Gattefosse) 94 ns Trio 111 *

ZO-1 %Control Significance Control 100 1.5mM CaCl2 121 * 0.0400% active matter Terminalia ferdinandiana extract (Kalmethic from Biocosmethic) 100 ns 0.01% active matter Lactobacillus Extract (Symreboot L19 from Symrise) 110 ns 0.0070% active matter Extract of Withania somnifera (EnergiNius of Gattefosse) 102 ns Trio 113 ***

Threshold for means statistical activity:

ns : > 0.05, not significant

* : 0.01 to 0.05, significant

** : 0.001 to 0.01, very significant t if

*** : < 0.001, extremely significant

So there is a significant link between tight junctions and barrier function.

Example 3: Result transepidermal water loss ( TEWL ) after s tripping with barrier function

Materials & Methods:

The efficacy of a formula F according to the invention, i.e. containing the combination of the trio ( Terminalia ferdinandiana extract at 0.4% active matter, Lactobacillus extract at 0.1% active matter and Withania somnifera extract at 0.07% active matter), ascorbyl glucoside (at 2% active matter) and hydroxypropyl tetrahydropyrantriol (at 6.3% active matter), in a medium comprising in particular water and glycerin, was proven using a TEWL test after stripping using:

24 women aged 18 to 63 (mean age: 47 ± 13 years):

- With a TEWL value ≥ 6 g,m-²,h-1 on the anterior surface of the forearms before stripping,

- With a TEWL value ≥ 20g,m-²,h-1 on the anterior surface of the forearm after stripping.

Results :

The results are in the table below.

Site Average p-value Average change since Average % Change since p-value p-value % Recovery ( ± SD) (average treated vs. untreated) Baseline _{after stripping} Baseline _{after stripping} (from Baseline _{after stripping} ) (mean change treated vs. untreated) ( ± SD) Baseline F 11.8 ± 2.0 S (p=0.0418) T00 before stripping Untreated 12.3 ± 2.4 T00 before stripping F 20.4 ± 0.4 NS (p=0.1181) T00 after stripping Untreated 20.7 ± 0.8 T00 after stripping 1h F 14.6 ± 1.7 -5.8 ± 1.8 -28.3% <0.0001 p<0.0001 -67.0% Untreated 17.5 ± 1.6 -3.2 ± 1.8 -15.4% <0.0001 -37.9% 2h F 13.9 ± 1.8 -6.5 ± 1.9 -31.9% <0.0001 p<0.0001 -75.5% Untreated 16.4± 1.5 -4.3 ± 1.5 -20.8% <0.0001 -51.0% 4h F 13.2 ± 2.0 -7.2 ± 1.1 -35.3% <0.0001 p<0.0001 -83.7% Untreated 15.5 ± 2.0 -5.2 ± 1.8 -25.2% <0.0001 -61.8% 6h F 12.4 ± 1.7 -8.0 ± 1.6 -39.1% <0.0001 p<0.0001 -92.6% Untreated 14.7 ± 1.8 -6.0 ± 1.8 -28.9% <0.0001 -70.9%

Single cutaneous application of the formula F according to the invention, under experimental conditions and on the skin of the forearm, led to a statistically significant decrease in transepidermal water loss (TEWL) approximately 6 hours later after stripping, showing a repair effect against water loss.

Formula F contains raw materials with a good index of naturalness and/or of natural origin and more particularly of plant origin.

II- Effects of a composition according to the invention on the skin firmness

Example 4: Sulfated GAGs Materials & Methods:

Normal human fibroblasts were seeded in 96-well plates and cultured for 24 hours in culture medium. The culture medium was then replaced with culture medium containing or not (control) the reference (TGF-β 10 ng/ml) or the tested compounds or combinations, and the cells were incubated for 72 hours. [35S]-sulfate was added to the culture medium during the last 24 hours of incubation. All experimental conditions were performed in n=3. At the end of the incubation, glycosaminoglycans were extracted from the cells using a chaotropic buffer. GAGs were then purified by ion exchange chromatography: adsorption of anionic molecules on Q-Sepharose beads and desorption of weakly and moderately anionic molecules using a specific buffer. The radioactivity incorporated into the molecules bound to the support was then measured by liquid scintillation.

Result :

As shown in the tables below, hydroxypropyl tetrahydropyrantriol diluted to 35%, tested at 0.1165% and 0.35%, dramatically stimulated the neosynthesis of sulfated GAGs by human fibroblasts. These results confirm the well-known effect of hydroxypropyl tetrahydropyrantriol on the enhancement of dermal GAGs.

Under the experimental conditions of this study, neither the trio according to the invention or its constituents tested alone, nor ascorbyl glucoside, nor the combination trio + ascorbyl glucoside, stimulated the neosynthesis of GAGs by human fibroblasts. However, surprisingly, the combination of the trio with ascorbyl glucoside and hydroxypropyl tetrahydropyrantriol dramatically increased the neosynthesis of GAGs by human fibroblasts. Since the results of the combination were superior to those of each active ingredient tested individually, or superior to the sum of the individual effects, these results clearly demonstrate a synergistic effect between the trio according to the invention, ascorbyl glucoside and hydroxypropyl tetrahydropyrantriol on the neosynthesis of GAGs.

Low concentration example %Control Control 100 10ng/mL TGF-β 205 0.1165% HT (diluted to 35%) 1210 0.1330% Vit CG 151 0.0262% Terminalia ferdinandiana extract (Kalmethic from Biocosmethic) 122 0.0067% Lactobacillus Extract (Symreboot L19 from Symrise) 124 0.0047% Extract of Withania somnifera (EnergiNius of Gattefosse) 100 Trio 113 Trio + Vit CG 182 Trio + HT 1266 Trio + Vit CG + HT 2006

High concentration example %Control Control 100 10ng/mL TGF-β 205 0.3500% HT (diluted to 35%) 1198 0.4000% Vit CG 203 0.0776% Terminalia ferdinandiana extract (Kalmethic from Biocosmethic) 113 0.02% Lactobacillus Extract (Symreboot L19 from Symrise) 130 0.0140% Extract of Withania somnifera (EnergiNius of Gattefosse) 100 Trio 117 Trio + Vit CG 207 Trio + HT 1291 Trio + Vit CG + HT 2443

The contents of the 3 extracts and HT in tables 5 and 6 are expressed in commercial product.

Example 5: Firmness – clinical assessment Materials & Methods:

Formula F according to the invention of Example 3 was used.

Subjects: 40 Asian women for clinical scoring by a dermatologist, aged 25–60 years, 50% sensitive skin (declarative), with signs of skin aging on the face and living in the city, with an inclusion grade ≥ 2 and ≤ 6 for the following parameters: Skin firmness (tactile).

Application: Twice a day (morning and evening) on the face, neck and upper chest.

The assessment is carried out using:

-Clinical rating: 10-point scale (0: none to 9: severe) at D0, D7, D28, D56 (N=40).

-Self-assessment questionnaire on D0, D1 (after the first awakening), D7, D14, D28, D56 (N=57).

-Spontaneous declarations of tolerance

Illustrations at D0, D28, D56 (N=40)

Results :

The effectiveness of the formula is proven by the clinical rating of firmness:

Time Average treatment Mean difference vs J0 % mean difference vs J0 p-value Significance J0 5.5 J28 4.8 -0.7 -12.89% <0.001 YES J56 4.00 -1.5 -27.56% <0.001 YES

Example 6: Self-assessment by consumers Materials and Methods:

Formula F according to the invention of Example 3 was used.

Subjects: See table below for gender and ethnicity, 25-60 years old, 50% sensitive skin (declarative), showing signs of skin aging on the face and living in the city, with an inclusion grade ≥ 2 and ≤ 6 for the following parameter: Skin firmness (tactile).

Application: Twice a day (morning and evening) on the face, neck and upper chest.

Formula effectiveness: consumer self-assessment.

Assessment method: Self-assessment questionnaires: 5-point scale / : Responses "Agree" and "Rather agree" in %, after 1 week, 2 weeks, 4 weeks and 8 weeks of application of people answering the questions: "My skin is firmer".

Results :

The results are as follows:

N subjects 1 week 2 weeks 4 weeks 8 weeks Caucasian men 101 38% 67% 86% 88% Caucasian women 57 81% Asian men 81 78% 92% 96% 98% Asian women 50 75% 81% 81% 83%

Consumers therefore rated Formula F as improving skin firmness.

Claims (17)

Composition, preferably cosmetic, comprising, in a cosmetically acceptable medium:
- at least one extract of Withania somnifera ;
- at least one extract of Terminalia ferdinandiana ; and
- at least one extract of Lactobacillus . Composition according to claim 1, in which the extract of Withania somnifera is an extract of a part of the plant selected from the group comprising the root, the fruit, the flower, the seed, the leaf, the stem, preferably the extract of Withania somnifera is an extract of root, advantageously dried and ground. Composition according to one of the preceding claims, in which the extract of Withania somnifera is obtained by an extraction process comprising a step of solid/liquid extraction of at least one part of the plant, followed by a second step of solid/liquid separation and finally a third step of recovery of the liquid phase, the solvent used by this process being a mixture of fructose, glycerin and optionally water. Composition according to one of the preceding claims, in which the extract of Withania somnifera is present in the composition according to the invention in a content of between 0.001% and 10% by weight relative to the total weight of the composition, preferably between 0.01% and 5% by weight, preferably between 0.05% and 3% by weight. Composition according to one of the preceding claims, in which the Terminalia ferdinandiana extract is an extract of a part of the plant chosen from the group comprising the root, the fruit, the flower, the seed, the leaf, the stem, preferably the Terminalia ferdinandiana extract is a fruit extract. Composition according to one of the preceding claims, in which the Terminalia ferdinandiana extract is obtained by a cold extraction process of at least one part of the plant, in particular under pressure. Composition according to one of the preceding claims, in which the Terminalia ferdinandiana extract is present in the composition according to the invention in a content of between 0.01% and 3% by weight relative to the total weight of the composition, preferably between 0.02% and 1% by weight, preferably between 0.03% and 1% by weight. Composition according to one of the preceding claims, wherein the Lactobacillus extract is an extract of Lactobacillus plantarum ( L. plantarum ), preferably the Lactobacillus extract is an extract of L. plantarum HEAL19 (DSM 15313), preferably the Lactobacillus extract is formulated with a prebiotic, preferably a maltodextrin. Composition according to one of the preceding claims, in which the Lactobacillus extract is present in the composition according to the invention in a content of between 0.001% and 1% by weight relative to the total weight of the composition, preferably between 0.01% and 0.8% by weight, preferably between 0.05% and 0.6% by weight. Composition according to one of the preceding claims, which also comprises at least one C-glycoside of the following general formula (I):
(I)
in which:
- R represents a linear alkyl radical, saturated in C1 to C10, in particular in C1 to C4, and which can optionally be substituted by at least one radical chosen from OH, COOH or COOR"2, with R"2 being a saturated C1-C4 alkyl radical;
- X represents a radical chosen from -CO-, -CH(OH)-, -CH(NH ₂ )-, -CH(NHCH2CH2CH2OH)-, -CH(NHPh)- and -CH(CH3)- and in particular a radical -CO-, -CH(OH)- or -CH(NH2)- and preferentially a group –CH(OH)-;
- S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of L and/or D series, said mono- or polysaccharide possibly being substituted by a hydroxyl group which is necessarily free, and optionally one or more amine function(s) which are optionally protected, and
- the S-CH2-X bond represents a C-anomeric bond, which can be α or β,
as well as their physiologically acceptable salts, their solvates such as hydrates and their optical and geometric isomers. Composition according to claim 10, in which the C-glycoside is chosen from:
- C-β-D-xylopyranoside-n-propane-2-one,
- C-α-D-xylopyranoside-n-propan-2-one,
- C-β-D-xylopyranoside-2-hydroxy-propane,
- C-α-D-xylopyranoside-2-hydroxy-propane,
- 1-(C-β-D-fucopyranoside)-propane-2-one,
- 1-(C-α-D-fucopyranoside)-propane-2-one,
- 1-(C-β-L-fucopyranoside)-propane-2-one,
- 1-(C-α-L-fucopyranoside)-propan-2-one,
- 1-(C-β-D-fucopyranoside)-2-hydroxy-propane,
- 1-(C-α-D-fucopyranoside)-2-hydroxy-propane,
- 1-(C-β-L-fucopyranoside)-2-hydroxy-propane,
- 1-(C-α-L-fucopyranoside)-2-hydroxy-propane,
- 1-(C-β-D-Glucopyranosyl)-2-hydroxyl-propane,
- 1-(C-α-D-Glucopyranosyl)-2-hydroxyl-propane,
- 1-(C-β-D-galactopyranosyl)-2-hydroxyl-propane,
- 1-(C-α-D-galactopyranosyl)-2-hydroxyl-propane
- 1-(C-β-D-fucofuranosyl)-propan-2-one,
- 1-(C-α-D-fucofuranosyl)-propan-2-one
- 1-(C-β-L-fucofuranosyl)-propan-2-one,
- 1-(C-α-L-fucofuranosyl)-propan-2-one,
- C-β-D-maltopyranoside-n-propan-2-one,
- C-α-D-maltopyranoside-n-propan-2-one
- C-β-D-maltopyranoside-2-hydroxy-propane,
- C-α-D-maltopyranoside-2-hydroxy-propane, their isomers or their mixtures,
preferably, the C-glycoside is selected from C-beta-D-xylopyranoside-2-hydroxy-propane and C-alpha-D-xylopyranoside-2-hydroxy-propane, preferably the C-glycoside is C-beta-D-xylopyranoside-2-hydroxy-propane. Composition according to claim 10 or 11, in which the C-glycoside is present in the composition in a content of 1% to 21% by weight of active material relative to the total weight of the composition, preferably from 2% to 9% by weight of active material, and more particularly from 3% to 7% by weight of active material. Composition according to one of the preceding claims, which also comprises ascorbic acid or one of its derivatives, preferably the ascorbic acid derivative is chosen from 5,6-di-O-dimethylsilylascorbate, the potassium salt of DL-alpha-tocopheryl-DL-ascorbyl-phosphate, magnesium ascorbyl phosphate, sodium ascorbyl phosphate, disodium ascorbyl sulfate, sulfinyl-L-ascorbic acid, glucopyranosyl-L-ascorbic acid and ascorbyl glucoside. Composition according to claim 13, in which the ascorbic acid or one of its derivatives is present in the composition in a content ranging from 1% to 15% by weight of ascorbic acid or one of its derivatives relative to the total weight of the composition, preferably from 1% to 10% by weight of active material, and more particularly from 1.5% to 5% by weight of active material. Use of a composition according to one of the preceding claims to strengthen the barrier function and/or improve the hydration of the skin. Use of a composition according to one of claims 1 to 14 for strengthening the firmness of the skin. Non-therapeutic cosmetic process for caring for keratin materials, such as the skin, comprising the topical application to these keratin materials of at least one composition according to one of claims 1 to 14.