N-acyl-L-homoserine lactones and their uses in cosmetics

Abstract

N-acyl-L-homoserine lactones and their uses in cosmetics The present invention relates to the cosmetic use of a compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, for skin care, preferably for improving the cutaneous signs of aging. The present invention relates to the cosmetic use of at least one compound of formula (I) or one of its salts, and / or one of its solvates and / or one of its isomers as an anti-aging active agent. Figure for abstract: none

Description

Title of the invention: N-acyl-L-homoserine lactones and their uses in cosmetics

[0001] The present invention relates to the cosmetic use of a compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, for skin care, preferably for improving the cutaneous signs of aging.

[0002] The present invention relates to the cosmetic use of at least one compound of formula (I) or one of its salts, and / or one of its solvates and / or one of its isomers as an anti-aging active agent.

[0003] The outer layer of the skin, the epidermis, is stratified and composed mainly of three types of cells which are keratinocytes, which are the vast majority, melanocytes and Langerhans cells. Each of these cell types contributes through its own functions to the essential role played in the body by the skin, in particular the role of protecting the body against external aggressions (climate, ultraviolet rays, tobacco, pollution, etc.).

[0004] The alterations associated with skin aging can manifest themselves in different ways, among which we can cite: - a microrelief characterized in particular by the appearance of fine wrinkles or fine lines, or by the presence of visible pores in high density, by roughness altering the surface appearance of the skin - loss of radiance, which leads to uneven skin tone; - loss of elasticity, suppleness, firmness, density, tone of the skin, sagging and / or wilting of the skin; - a slowdown in epidermal renewal leading to thinning of the horny layer of the skin and a papery appearance of the skin; - and skin dryness resulting from a reduction in the barrier function of the skin's stratum corneum.

[0005] Among the anti-aging active ingredients available, retinol is unanimously known to be effective on the signs of skin aging, and thus, used to treat a wide range of skin problems, including wrinkles and fine lines, and more generally to improve radiance.

[0006] However, the use of retinol can be limited by its instability, its sensitivity to oxidation, light, heat, but also its spontaneous degradation over time. The instability of retinol thus requires special precautions for good formulation and good use.

[0007] There is therefore a need to provide new active ingredients that are effective against the signs of skin aging, stable and easier to formulate.

[0008] The present invention meets this need. Indeed, as demonstrated in particular in examples, the Applicant has identified a family of N-acyl-L-homoserine lactone compounds, effective in stimulating cell proliferation and epidermal cell renewal. Summary of the invention

[0009] The present invention thus relates to the cosmetic use of at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, for skin care.

[0010] The present invention relates in particular to the cosmetic use of at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, for improving the cutaneous signs of aging.

[0011] The present invention also relates to the cosmetic use of at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, as an anti-aging active agent.

[0012] The present invention also relates to a cosmetic composition comprising, in a physiologically acceptable medium:

[0013] (i) at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, and

[0014] (ii) at least one additive chosen from hydrophilic or lipophilic gelling agents, fatty substances such as oils, emulsifiers, perfumes, fillers, sunscreens, coloring matters, anti-aging active agents other than the compounds of formula (I) and (II), desquamating active agents, moisturizing active agents, emollients, preservatives and mixtures thereof.

[0015] The present invention also relates to a cosmetic treatment process for the care of keratin materials, preferably the skin, comprising the application to the keratin materials, preferably the skin, more preferably the skin showing signs of cutaneous aging, of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound chosen from the compounds of formula (I), the compounds of formula (II), or one of their salts, and / or solvates, and / or isomers. Definitions

[0016] “Keratin materials” means the skin of the body or face, the lips, the mucous membranes, the eyelashes, the nails, and the hair of a human being.

[0017] By "skin" is meant the entire skin of the body and the scalp of a being human and preferably, the skin of the face, décolleté, neck, arms and forearms, hands or even more preferably, the skin of the face (in particular the forehead, nose, cheeks, lips, chin), décolleté and neck.

[0018] By "solvated" is meant the mixture of a compound of formula (I) with one or more molecules of water or organic solvent.

[0019] By "isomer" is meant in particular the optical isomers or any positional isomer, or any geometric isomer of a compound of formula (I), (I'), (II), (II').

[0020] By "unsaturated" is meant the presence of one to three double bonds, preferably one or two ethylenic double bonds.

[0021] The term “salt” of a compound of formula (I), (I'), (II), (II') according to the invention means a salt formed by an inorganic or organic acid.

[0022] Examples of acid salts include sulfate, citrate, acetate, oxalate, chloride, bromide, iodide, nitrate, bisulfate, phosphate, isonicotinate, lactate, salicylate, citrate, tartrate, oleate, tannate, pantothenate, bitartrate, ascorbate, succinate, maleate, gentisinate, fumarate, gluconate, glucuronate, saccharate, formate, benzoate, glutamate, methanesulfonate, ethanesulfonate, benzenesulfonate, p-toluenesulfonate and pamoate (i.e. 1,1'-methylene-bis-(2-hydroxy-3-naphthoate).

[0023] Examples of basic salts include alkali metal hydroxides such as sodium, potassium and lithium; alkaline earth metal hydroxides such as calcium and magnesium; other metal hydroxides such as aluminum and zinc; ammonia and organic amines such as unsubstituted or hydroxy-substituted mono-, di- or tri-alkylamines; dicyclohexylamines; tributyl amines; pyridine; N-methyl-N-ethylamine; diethylamine; triethylamine; mono-, bis- or tris-(2-hydroxy-alkylamines) such as mono-, bis- or tris-(2-hydroxyethyl)amine, 2-hydroxy-tert-butylamine, tris-(hydroxymethyl)methylamine, N,N-di-alkyl-N-(hydroxyalkyl)-amines, such as N,N-dimethyl-N-(2-hydroxyethyl)amine or tri-(2-hydroxyethyl)amine; N-methyl-D-glucamine; and amino acids such as arginine and lysine, preferably a basic salt, and in particular a sodium or potassium salt. Detailed description

[0024] The present invention thus relates to the cosmetic use of at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, for skin care.

[0025] The present invention relates in particular to the cosmetic use of at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, for improving the cutaneous signs of aging.

[0026] The present invention also relates to the cosmetic use of at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, as an anti-aging active agent.

[0027] The compounds of formula (I) are as follows:

[0028] [Chem.l]

[0029] Where:

[0030] - R is a linear or branched, saturated or unsaturated hydrocarbon chain, of preferably saturated linear, comprising from 1 to 29 carbon atoms, preferably from 3 to 29 carbon atoms, preferably from 5 to 19 carbon atoms, preferably from 6 to 17 carbon atoms, preferably from 6 to 11 carbon atoms, and said chain being optionally substituted by one or more -OH group(s) and / or interrupted by one or more carbonyl(s) (C=O); and

[0031] - R2 is chosen from a hydrogen atom, a linear (Cl-C4)alkyl group or branched, preferably linear, substituted or unsubstituted, preferably unsubstituted such as methyl or ethyl, preferably R2 represents a hydrogen atom.

[0032] The compounds of formula (II) are as follows:

[0033] [Chem.2] (II)

[0034] Where:

[0035] - R has the same definition as for formula (I), i.e. R is a hydrocarbon chain linear or branched, saturated or unsaturated, preferably linear saturated, comprising from 1 to 29 carbon atoms, preferably from 3 to 29 carbon atoms, preferably from 5 to 19 carbon atoms, preferably from 6 to 17 carbon atoms, preferably from 6 to 11 carbon atoms, and said chain being optionally substituted by one or more -OH group(s) and / or interrupted by one or more carbonyl(s) (C=O). ;

[0036] - R2 has the same definition as for formula (I) ie R2 is chosen from an atom of hydrogen, a linear or branched (Cl-C4)alkyl group, preferably linear, substituted or unsubstituted, preferably unsubstituted such as methyl or ethyl, preferably R2 represents a hydrogen atom.

[0037] and

[0038] - X is chosen from OR1 or NR2R3: • RI representing a hydrogen or a linear or branched (Cl-C4)alkyl, preferably linear, substituted, in particular by one or more hydroxy or unsubstituted, preferably RI represents a hydrogen; and • NR2R3 represents a primary, secondary or tertiary amine, R2 and R3 identical or different, preferably identical, representing a hydrogen atom, a linear or branched (Cl-C4)alkyl group, preferably linear, substituted, in particular by one or more hydroxyl groups, or unsubstituted, preferably unsubstituted such as methyl or ethyl; preferably R2=R3=H; or R2 and R3 carried by the same nitrogen atom together form a preferably monocyclic heterocycle comprising from 5 to 7 members, preferably 5 to 6 members, saturated or unsaturated, substituted or unsubstituted, and optionally comprising one or more heteroatoms identical or different from that of the nitrogen atom, preferably the heterocycle is chosen from the morpholino, piperazino, pi-peridino, pyrrolidino groups.

[0039] Preferably, R is neither substituted by a -OH nor interrupted by a carbonyl.

[0040] The salts of the compounds of formula (I) or (II) are chosen from all cosmetically acceptable salts. By "cosmetically acceptable salt" is meant a salt compatible with the skin, mucous membranes and / or superficial body appendages.

[0041] Preferably, the compounds of formula (I) are the compounds of formula (I'):

[0042] [Chem.3] (D

[0043] where R is as defined previously.

[0044] Preferably, the compounds of formula (II) are the compounds of formula (II”):

[0045] [Chem.4] (II')

[0046] where R is as defined previously.

[0047] Even more preferably, the compounds of formula (I) are the compounds of formula (I”):

[0048] [Chem.5] O 'NH R (D

[0049] where R is as defined previously.

[0050] Even more preferably, the compounds of formula (II) are the compounds of formula (II”):

[0051] [Chem.6] (II')

[0052] where R is as defined previously.

[0053] Preferably, for formulas (I) and (II) (and (I') and (II')), R is a saturated linear hydrocarbon chain comprising from 1 to 29 carbon atoms, preferably from 3 to 29 carbon atoms, preferably from 5 to 19 carbon atoms, preferably from 6 to 17 carbon atoms, preferably from 6 to 11 carbon atoms. Preferably, R is neither substituted by a -OH nor interrupted by a carbonyl.

[0054] Preferably, the compound(s) are chosen from the compounds of formula (I), their salts, their solvates and / or their isomers, preferably from the compounds of formula (I').

[0055] Preferably, the compound(s) are chosen from the following compounds, their salts and / or their solvates and their isomers:

[0056] [Tables 1]

[0057] Preferably, the compound is chosen from the following compounds and their salts:

[0058] [Tables 2] o A bso I u te s te r» chsmi st ry s ho wn Absolute te storeochemistry shown Rotet<»n (+} Absoute .stereoc hemistry shown Double bond geometry shown Absolute stereochemistry shown o ITS Absolute stereochemistry shown Absolute stereochemistry shown Rotation <+ i Absolut© stereochemistry shown Absolut© stereochemistry shown Ab soi u te ste reoch emi stry sh own Abso 1 u te s te reochem is tr y sho wn Rotation <+•> Absolute stenÿoc hemsstry shown o Ab 50i ute ste reoc hemi stry shown

[0059] According to one embodiment, the compounds according to the invention are chosen from the following compounds, their salts and / or their solvates and their isomers:

[0060] [Tableaux3] O • MH _ o' yy \—-—JOO . / ..,. .........

[0061] According to one embodiment, the compounds according to the invention are chosen from the following compounds, their salts and / or their solvates and their isomers:

[0062] [Tables4]

[0063] According to one embodiment, the compounds according to the invention are chosen from the following compounds, their salts and / or their solvates and their isomers:

[0065]

[0066]

[0064] According to one embodiment, the compounds according to the invention are chosen from the following compounds, their salts and / or their solvates and their isomers:

[0067]

[0068]

[0069] Preferably the compound of formula (I) (and (!)) is a compound as mentioned in the context of the present invention, in which R is a linear or branched, saturated, preferably linear saturated hydrocarbon chain, comprising from 6 to 11 carbon atoms, preferably a linear saturated chain of 7 carbon atoms. Preferably, the compound of formula (I) and (!') is as described below: [Chem. 7]

[0070] Even more preferably, the compound of formula (I) and (!')) is chosen from:

[0071]

[0072] In particular, it is N-octanoyl-L-homoserine lactone (CAS 147852-84-4, or N-[(3S)-2-oxooxolan-3-yl]octanamide):

[0073] [Chem. 8] o

[0074] The cosmetic use of at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers according to the invention is aimed at skin care.

[0075] In particular, the cosmetic use of at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers according to the invention aims to improve the cutaneous signs of aging. Preferably, the compound(s) chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers according to the invention, are used as an anti-aging active agent.

[0076] All uses according to the invention are cosmetic, i.e. non-therapeutic.

[0077] More particularly, the present invention aims to improve the cutaneous signs of aging.

[0078] By “improving the skin signs of aging” is meant in particular preventing and / or reducing the skin signs of aging.

[0079] By "skin signs of aging" is meant all changes in the external appearance of the skin due to aging.

[0080] The cutaneous signs of aging targeted by the invention can be chosen from an appearance of a microrelief of the skin, a formation and / or a presence of fine wrinkles or fine lines, the appearance of roughness, an alteration in the surface appearance of the skin, an alteration in the radiance of the skin tone, unevenness of the skin tone, a loss of elasticity, a loss of suppleness, a loss of firmness, a loss of density, or a loss of skin tone, sagging and / or wilting of the skin, thinning of the horny layer of the skin and a papery appearance of the skin, dry skin.

[0081] Preferably, the cutaneous signs of aging targeted by the invention are chosen from the appearance of a microrelief of the skin, the formation and / or the presence of fine wrinkles or fine lines, the appearance of roughness, the alteration of the surface appearance of the skin, the thinning of the horny layer of the skin and the papery appearance of the skin, cutaneous dryness

[0082] More preferably, the cutaneous signs of aging targeted by the invention are chosen from the appearance of a microrelief of the skin, the formation and / or the presence of fine wrinkles and / or fine lines, the appearance of roughness, the alteration of the surface appearance of the skin, the thinning of the horny layer of the skin, skin dryness.

[0083] The skin is in particular the skin of a mammal, preferably human. Preferably, the skin is aged. By "aged skin" is meant a general aesthetic condition of the skin resulting from aging.

[0084] Preferably, the compound(s) chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers according to the invention, are used in an amount of between 0.001 and 15%, preferably between 0.01 and 12%, even more preferably between 0.01 and 10%.

[0085] The present invention also relates to a cosmetic treatment process for the care of keratin materials, preferably the skin, comprising the application to the keratin materials, preferably the skin, more preferably the skin showing signs of cutaneous aging, of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound chosen from the compounds of formula (I), the compounds of formula (II), or one of their salts, and / or solvates, and / or isomers.

[0086] The present invention also relates to a cosmetic composition comprising, in a physiologically acceptable medium:

[0087] (i) at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, and

[0088] (ii) at least one additive chosen from hydrophilic or lipophilic gelling agents, fatty substances such as oils, emulsifiers, perfumes, fillers, sunscreens, coloring matters, anti-aging active agents other than the compounds of formula (I) and (II), desquamating active agents, moisturizing active agents, emollients, preservatives and their mixtures.

[0089] Preferably, the cosmetic composition has a pH of between 6 and 8, preferably between 6.5 and 7.5, preferably around 7.

[0090] Preferably, the composition according to the invention comprises at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, in an amount of between 0.001 and 15%, preferably between 0.01 and 12%, even more preferably between 0.01 and 10%.

[0091] The quantities of these different additives (ii) are those conventionally used in the fields considered, and for example range from 0.01 to 80% of the total weight of the composition. These additives, depending on their nature, can be introduced into the fatty phase or into the aqueous phase. These additives, as well as their concentrations, must be such that they do not harm the advantageous properties of the compound of formula (I), of formula (II) or its salt, or its solvate and / or its isomer according to the invention.

[0092] Said physiologically acceptable medium may for example consist of water or a mixture of water and at least one physiologically acceptable organic solvent.

[0093] According to a preferred embodiment, the compositions of the invention comprise at least 20% by weight of water, in particular at least 40% by weight of water relative to the total weight of said composition.

[0094] Preferably, the composition according to the invention has a water content ranging from 20% to 95% by weight, even better from 40% to 90% by weight relative to the total weight of the composition.

[0095] As organic solvents which can be used in the composition of the invention, mention may be made of organic solvents miscible in water.

[0096] By "water-miscible solvent" according to the present invention is meant a compound which is liquid at room temperature and miscible with water, in particular having a miscibility in water greater than 50% by weight at 25°C and atmospheric pressure.

[0097] The water-miscible organic solvents may be chosen from lower monoalcohols having from 2 to 5 carbon atoms such as ethanol and isopropanol, glycols having from 2 to 8 carbon atoms such as ethylene glycol, hexylene glycol, propylene glycol, 1,3-butylene glycol, pentylene glycol, dipropylene glycol and glycerin.

[0098] The water-miscible organic solvent(s) may be present in a concentration of 0.01% to 30% by weight, preferably 0.1% to 20% by weight and more preferably 1% to 10% by weight, relative to the total weight of the composition.

[0099] As oils which can be used in the composition of the invention, we can cite for example:

[0100] - hydrocarbon oils of animal origin;

[0101] - hydrocarbon oils of vegetable origin;

[0102] - synthetic esters and ethers, in particular of fatty acids, such as oils of formulas R1COOR2 and R1OR2 in which RI 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;

[0103] - linear or branched hydrocarbons, of mineral or synthetic origin;

[0104] - fatty alcohols having from 8 to 26 carbon atoms;

[0105] - partially hydrocarbon and / or silicone fluorinated oils;

[0106] - silicone oils;

[0107] - their mixtures.

[0108] Oil is understood to mean any fatty substance in liquid form at room temperature (20-25°C) and atmospheric pressure. These oils can be of vegetable, mineral or synthetic origin.

[0109] In the list of oils cited above, the term hydrocarbon oil means any oil comprising mainly carbon and hydrogen atoms, and possibly ester, ether, fluorine, carboxylic acid and / or alcohol groups.

[0110] Other fatty substances which may be present in the oily phase are, for example, fatty acids containing 8 to 30 carbon atoms; waxes; silicone resins; and silicone elastomers.

[0111] 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.

[0112] According to a particular embodiment of the invention, the composition used in the context of the invention is a water-in-oil (W / O) or oil-in-water (O / W) emulsion. The proportion of the oily phase of the emulsion can range from 5 to 90% by weight, and preferably from 5 to 60% by weight relative to the total weight of the composition.

[0113] The composition may comprise at least one emulsifier. The emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or non-ionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are chosen appropriately according to the emulsion to be obtained (W / O or O / W). 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.

[0114] As coloring matter, we can cite pigments and / or nacres.

[0115] A composition used according to the invention comprises in particular at least one compound of formula (I), (I'), (II), (II') described above and can be presented in all the galenic forms normally used in the cosmetic field.

[0116] It may be in particular in the form of an anhydrous composition, an aqueous, hydroalcoholic, optionally gelled solution, a dispersion of the lotion type, optionally two-phase, an oil-in-water or water-in-oil or multiple emulsion, an aqueous gel, a dispersion of oils in an aqueous phase, in particular using spherules, these spherules being able to be polymeric particles or better, lipid vesicles of ionic and / or non-ionic type, or even in the form of a powder, a serum, a paste or a flexible stick or even a stick. It may be of solid, pasty, or more or less fluid liquid consistency. It may be optionally applied to the skin in the form of an aerosol. It may also be in solid form, and for example in the form of a stick.

[0117] Thus, the composition may comprise all the constituents usually employed in the application and topical administration envisaged.

[0118] A composition according to the invention may advantageously be in the form of an emulsion, in particular obtained by dispersing an aqueous phase in a fatty phase (W / O) or a fatty phase in an aqueous phase (O / W), of liquid or semi-liquid consistency of the milk type, or of soft, semi-solid or solid consistency of the cream or gel type, or even of multiple emulsion (W / O / W or O / W / O). These compositions are prepared according to the usual methods.

[0119] Said compound(s) of formula (I), (I'), (II), (II'), or said composition containing them are implemented, within the framework of a use or a method according to the invention, by topical route.

[0120] The compositions according to the invention may be applied directly to the skin or, alternatively, to cosmetic supports of the occlusive or non-occlusive type, intended to be applied locally to the skin. As non-limiting examples of cosmetic supports, mention may in particular be made of a patch, a wipe, a roll-on and a pen.

[0121] The composition may or may not be rinsed off after being applied to the skin.

[0122] The invention is now illustrated by the following examples. Examples Example 1: Epidermal proliferation test Principle:

[0123] The aim of this study is to evaluate the potential of N-octanoyl-L-homoserine lactone to modulate the expression of a gene involved in the physiology of normal human epidermal keratinocytes (notably epidermal renewal, such as epidermal proliferation) by quantitative RT-PCR.

[0124] N-octanoyl-L-homoserine lactone is estimated at 1 g / L in DMSO.

[0125] N-octanoyl-L-homoserine lactone is compared to retinoic acid at 107 M (i.e. 3.105 g / L) in DMSO.

[0126] The most significant marker studied is the epidermal renewal gene HBEGF (Heparin-binding EGF-like growth factor, Gene ID No. 1839). HBEGF is a growth factor that binds to the EGF receptor and stimulates the growth of epithelial cells. It has been shown that the effects of retinoic acid on hyperplasia (in vitro and in vivo) are mediated by an increase in the expression of this factor (Retinoid-Induced Epidermal Hyperplasia Is Mediated by Epidermal Growth Factor Receptor Activation Via Specific Induction of its Ligands Heparin-Binding EGF and Amphiregulin in Human Skin In Vivo. Rittié L. et al. 2006. Journal of Investigative Dermatology, Vol 126, Issue 4, 732-739). The housekeeping gene GAPDH serves as a gene for normalizing the results. Protocols (experimental conditions): Cytotoxicity

[0127] Normal human keratinocytes were seeded into 96-well plates and cultured for 24 hours in medium dosage. The culture medium was then replaced with culture medium containing or not (control) the test compounds. After 72 hours of incubation, cell viability was measured according to a standard measure of mitochondrial activity using MTT.

[0128] Expression of transcripts in human keratinocytes

[0129] Human epidermal keratinocytes were seeded in a 24-well culture plate and cultured for 72 hours at 37°C and 5% CO2 in culture medium with renewal of the culture medium after the first 24 hours. At the end of the incubation, the culture medium was replaced with assay medium (supplemented with 1.5 mM CaCl2) containing or not (control) the starting material or reference (retinoic acid) and the cells were incubated for another 24 hours.

[0130] All experimental conditions were performed in n=2. At the end of treatment, cells were washed twice in PBS (without CaCl2, without MgCl2) and RNA extraction was performed using TriPure Isolation Reagent® according to the manufacturer's recommendations. The relative expression of the selected markers was measured by two-step RT-qPCR.

[0131] First, reverse transcription was performed using Transcriptor Reverse Transcriptase (ROCHE) according to the manufacturer's recommendation. Then, PCR experiments were performed using a LightCycler® 480 real-time PCR system by a SYBR®Green incorporation measurement system (Roche). Results and conclusions:

[0132] The results are expressed as modulation factor (Fc, fold change) compared to the untreated control after normalization of the relative expressions compared to the expression of a housekeeping gene (GAPDH). The Fc value of the housekeeping gene GAPDH is therefore equal to 1. The expression of a gene is considered to be stimulated when it is multiplied by at least 1.5.

[0133] Effects of N-octanoyl-L-homoserine lactone on the expression of a gene involved in the physiology of normal human epidermal keratinocytes. The housekeeping gene GAPDH serves as a normalizing gene.

[0134] [Tables4] HTS Laboratory Retinoic acid N-octanoyl-L-homoserine lactone (ref 44558 Sigma-Aldrich, CAS 147852-84-4) Gene l,00E-07 1 M g / L GENE_CLUSTER GENE_SYMB OL DMSO DMSO Epidermal Renewal HBEGF 2.64 31.78 Housekeeping Genes GAPDH 1.01 1.00

[0135] Retinoic acid, tested at 10 7 M (i.e. 3.10-5 g / L), significantly increases (Fc = 2.64) the expression of the HBEGF marker involved in epidermal renewal (Rittié et al. 2006). This result was expected and validates the assay.

[0136] N-octanoyl-L-homoserine lactone, tested at 1 g / L, also significantly increases (Fc = 31.78) the expression of the HBEGF marker involved in epidermal renewal.

[0137] This result shows that N-octanoyl-L-homoserine lactone is effective in improving epidermal renewal.

[0138] Example 2: Functional test of epidermal renewal in reconstructed model Principle:

[0139] The aim of this study is to evaluate the efficacy of N-octanoyl-L-homoserine lactone, under systemic conditions, in stimulating epidermal renewal by modulating the thickness and / or histological quality of a reconstructed 3D model of epidermal tissue between 10 and 14, or 10 and 17 days of maturation.

[0140] N-octanoyl-L-homoserine lactone is estimated at 10 pg / mL (i.e. 0.01 g / L) in DMSO.

[0141] N-octanoyl-L-homoserine lactone is compared to retinol at 3 pM (i.e. 8.6.10 4 g / L) in DMSO. Protocols (experimental conditions):

[0142] The epidermal thickness evaluation test is carried out to evaluate the effectiveness of the raw materials, in systemic application, on the reconstruction of the epidermis in the 3D in vitro SkinEthic RHE® model for 4 or 7 days. The effects of the active ingredients are determined by an evaluation of the quality of the reconstructed epidermis based on its thickness and morphology. Materials

[0143] - Standard equipment for biological tests (pipette, tubes, etc.)

[0144] - 6-well plates

[0145] - Optical coherence tomography equipment with Newtone® software (acquisition EPISKIN and EpiSkin RHEV2 treatment)

[0146] - Classic material for histological study (fixing samples, etc.)

[0147] - 96-well 2 mL Depp plates (for analytical biochemistry analyses) Reagents

[0148] - RHE culture medium (SGM)

[0149] - Retinol

[0150] - DMSO

[0151] - Formaldehyde

[0152] - Coloring reagent for HE Biological model

[0153] The experiments are carried out on the SkinEthic RHE® reconstructed epidermis model.

[0154] Tissues are received on medium on Day 10 and stored at 37°C (95% humidity and 5% carbon dioxide) until the end of treatment on D14 or D17. RH3E TEST METHOD Solubilization

[0155] For compounds solubilized in DMSO, 1000X solutions are first vortexed for 1 min and stored at room temperature.

[0156] For compounds solubilized in water, 10X solutions are prepared in the same manner in the medium.

[0157] The appearance of solubility is assessed visually.

[0158] The solutions are then diluted in the medium to obtain the final solution IX and stored at 4°C. Treatment

[0159] Systemic treatments are carried out on D10, D12 and harvest on D14 (short-term protocol).

[0160] Tissues are cultured with 2 mL of treatment solution (raw material in SGM medium) in 6-well plates and stored at 37°C (95% humidity and 5% carbon dioxide) between treatments.

[0161] For all conditions, the MP (Raw Materials) are tested in three replicates (n = 3).

[0162] For MPs of interest, if no toxicity and good histological quality are observed at D14, it is possible to treat the tissues at D14 with 3 mL of treatment solution and harvest them at D17 as part of a long-term protocol. Viability

[0163] No specific viability study is performed in this test. Cell viability is monitored during the first treatment by histological analysis to verify the tissue's ability to generate good quality epidermis. OCT acquisition and analysis

[0164] OCT (Optical Coherence Tomography) is a non-invasive imaging technique, based on the analysis of infrared light reflected by tissues and the creation of an interference signal.

[0165] OCT allows visualization of surface aspects, the 2D structures of the RHE® model are followed during epidermal reconstruction. This also allows to determine, thanks to acquisition and segmentation with Newtone® algorithms, the epidermal thickness of the tissue after reconstruction. Image acquisition and analysis are carried out at D10, D12, and D14 in all tested conditions. A variation in thickness with the first day of treatment is carried out in order to observe the evolution of the thickness for all tissues. In a second step, the thickness variations are rationalized according to the vehicle (untreated control or DMSO). Histology

[0166] A histological analysis is performed on all tested conditions and tissues in order to evaluate the impact of the treatment on the quality of the reconstruction. The histology process and hematoxylin and eosin staining are performed in accordance with the Episkin histology platform protocol.

[0167] Analysis of treatment cytotoxicity and histological qualities is performed and compared to untreated conditions or vehicle conditions.

[0168] INTERPRETATION CRITERIA References

[0169] The test includes 3 references to guarantee the good quality of the batch of tissues and the good response of the treatments:

[0170] - The untreated control, as a negative reference,

[0171] - DMSO, as a vehicle without effect,

[0172] - Retinol, a positive reference for tissue quality with an increase in pro cell liferation (epidermal thickness) and a reduction in differentiation (histological quality).

[0173] The expected results for these references are as follows:

[0174] - Untreated witness: good and homogeneous overall quality with a thickness of epidermis up to 80 pm on D10 (or on the first day of treatment),

[0175] - DMSO: good overall quality close to the untreated control without negative impact on the thickness of the epidermis on the day of harvest,

[0176] - Retinol: a decrease in differentiation compared to the vehicle with a better stratification and epidermal thickness up to 15% compared to DMSO from variation D10 to D14. Molecules tested

[0177] For each molecule tested, the interpretation criteria are based on:

[0178] - the thickness of the epidermis,

[0179] - the histological quality at the end of treatment.

[0180] Each condition is compared to the vehicle (untreated control or DMSO control). Raw data (OCT measurements)

[0181] E10 (pm): Thickness of the epidermis at D10

[0182] E14 (pm): Thickness of the epidermis at D14 Calculations

[0183] VAR (%): Variation in epidermal thickness between D10 and D14

[0184] With VAR (in %) = [(E14 / E10) x 100] - 100

[0185] VAR_normalized (%): Variation in epidermal thickness between D10 and D14, normalized:

[0186] - relative to solvent (DMSO) for retinol and N-octanoyl-L-homoserine lactone,

[0187] - and with respect to the untreated fabric for the untreated fabrics and the solvent,

[0188] With normalized VAR (%) = VAR (%) - (average of the VARs of the 3 biological replicates (%))

[0189] Considering:

[0190] - biological replicates of DMSO for retinol and N-octanoyl-L-homoserine lactone,

[0191] - biological replicates of the untreated Tissue for the untreated Tissues and for the Solvent (DMSO).

[0192] Average_VAR_normalized (%): Average of the Variations in the Thickness of the epidermis between D10 and D14, standardized for the 3 biological replicates,

[0193] With Average_VAR_normalized (%) = (VAR_normalized replicate 1 + VAR_normalized replicate 2 + VAR_normalized replicate 3) / 3

[0194] EC_ VAR_normalized (%): Standard deviation of the Variations in the Thickness of the epidermis between D10 and D14, normalized for the 3 biological replicates

[0195] With EC_ VAR_normalized (%) = [ (VAR_normalized (%) - Average_VAR_normalized (%))2 / 3 ]. Results and conclusions:

[0196] The results of the untreated tissues and DMSO are expressed as the average variation in the thickness of the epidermis of the reconstructed model tissue, between D10 and D14, normalized compared to the untreated tissues.

[0197] The results for retinol and N-octanoyl-L-homoserine lactone are expressed as the mean variation in the thickness of the epidermis of the reconstructed model tissue, between D10 and D14, normalized to the solvent (DMSO).

[0198] These standardized average variations are expressed as a percentage and are considered significant when they are greater than or equal to 10%.

[0199] Variation in thickness (in pm) of the reconstructed epidermal model between D10 and D14. Calculations of the percentages of variation compared to the vehicle). TNT: Untreated tissues

[0200] [Tables5] MP Concentration Biological Replicate E10 (pm) (1) E14 (pm) (2) VA R (%) (3) VAR_normalized (%) (4) Mean _VAR_normalized (%) (5) EC_ VAR_normalized (%) (6) TNT na 1 84.0 4 114.6 3 36.4 0 3.84 0.00 3.38 2 91.0 8 118.4 6 30.0 6 -2.50 3 89.8 5 117.9 0 31.2 2 -1.34 DMSO 0.1% 1 90.1 9 117.1 6 29.9 0 -2.66 -3.55 0.78 2 90.0 6 115.7 0 28.4 8 -4.08 3 87.7 7 112.9 1 28.6 4 -3.92 Retinol in DMSO 3 pM 1 76.8 1 127.2 4 65.6 6 36.66 37.13 2.68 2 76.0 8 128.6 0 69.0 3 40.02 3 77.0 9 126.2 3 63.7 3 34.72 N-octanoyl-L-homo serine lactone in DMSO 10 pg / mL 1 79.2 7 110.8 4 39.8 3 10.83 11.98 1.01 2 78.1 4 110.4 8 41.4 0 12.39 3 76.6 7 108.6 6 41.7 2 12.71

[0201] (1) Thickness OCT J10

[0202] (2) Thickness OCT J14

[0203] (3) Thickness variation between J10_J14

[0204] (4) Thickness variation between J10_J14, normalized

[0205] (5) Average for the 3 biological replicates of the thickness variations between J10_J14, normalized

[0206] (6) Standard deviation for the 3 biological replicates of the thickness variations between J10_J14, normalized

[0207] Retinol, tested at 3 pM (i.e. 8.6.10 4 g / L), significantly increases epidermal thickness with a variation greater than 30%. This result was expected and validates the dosage.

[0208] N-octanoyl-L-homoserine lactone, tested at 10 pg / mL (i.e. 0.01 g / L), shows a significant positive effect on epidermal renewal compared to retinol (with 12% more variation compared to the solvent) under the conditions of this test.

Claims

Claims

1. Cosmetic use of a compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers, for skin care, in which formula (I) is as follows: [Chem.l] (I) Or : - R is a linear or branched, saturated or unsaturated, preferably linear saturated, hydrocarbon chain comprising from 1 to 29 carbon atoms, preferably from 3 to 29 carbon atoms, preferably from 5 to 19 carbon atoms, preferably from 6 to 17 carbon atoms, preferably from 6 to 11 carbon atoms, and said chain being optionally substituted by one or more -OH group(s) and / or interrupted by one or more carbonyl(s) (C=O); and - R2 is chosen from a hydrogen atom, a linear or branched (Cl-C4)alkyl group, preferably linear, substituted or unsubstituted, preferably unsubstituted such as methyl or ethyl, preferably R2 represents a hydrogen atom, and formula (II) is as follows: [Chem. 2] HO-—\ (II) Where: - R has the same definition as for formula (I), ie R is a linear or branched, saturated or unsaturated, preferably linear saturated, hydrocarbon chain comprising from 1 to 29 carbon atoms, preferably from 3 to 29 carbon atoms, preferably from 5 to 19 carbon atoms, preferably from 6 to 17 carbon atoms, preferably from 6 to 11 carbon atoms, and said chain being optionally substituted by one or more -OH group(s) and / or interrupted by one or more carbonyl(s) (C=O). ; - R2 has the same definition as for formula (I) ie R2 is chosen from a hydrogen atom, a linear or branched (Cl-C4)alkyl group, preferably linear, substituted or unsubstituted, preferably unsubstituted such as methyl or ethyl, preferably R2 represents a hydrogen atom. And - X is chosen from OR1 or NR2R3: • RI representing a hydrogen or a linear or branched (Cl-C4)alkyl, preferably linear, substituted, in particular by one or more hydroxy or unsubstituted, preferably RI represents a hydrogen; and • NR2R3 represents a primary, secondary, or tertiary amine, R2 and R3 identical or different, preferably identical, representing a hydrogen atom, a linear or branched (Cl-C4)alkyl group, preferably linear, substituted, in particular by one or more hydroxyl, or unsubstituted, preferably unsubstituted such as methyl or ethyl; preferably R2=R3=H; or R2 and R3 carried by the same nitrogen atom together form a preferably monocyclic heterocycle comprising from 5 to 7 members, preferably 5 to 6 members, saturated or unsaturated, substituted or unsubstituted, and optionally comprising one or more heteroatom(s) identical or different from that of the nitrogen atom, preferably the heterocycle is chosen from the morpholino, piperazino, piperidino, pyrrolidino groups.

2.

3.

4. Use according to claim 1, for improving the cutaneous signs of aging. Use according to claim 1 or 2, as an anti-aging active ingredient. Use according to one of the preceding claims, in which the compound is of formula (!): [Chem. 3] (!), and in particular of formula (I”) [Chem. 5]

5. where R is as defined in claim 1. Use according to one of claims 1 to 3, in which the compound is of formula (II'): [Chem. 4] (II'), and in particular of formula (II”) [Chem. 6]

6. where R is as defined in claim 1. Use according to one of claims 1 to 3, in which the compound is chosen from the following compounds, their salts, their solvates and / or their isomers:

7. Use according to one of claims 1 to 3 or 6, in which the compound is chosen from the following compounds and their salts: Absobite stereochemistry shown Ab§o!ute stereochemistry shown O Absolute stereochemistry shown Absolute stereochemistry shown Absoute stgreochsmistry shown Absolut® stereochemlstry shown Absoute stsreQchsmjstry shown Double bond geenietry shown Abs o! u te .ste reoch© ms si ry show n Absoh-ite stengtochemstry $hown Rotation (•+•) Absolut© stereochemistry shown Absolut© stereochemlstry shown Absolut© stereochemistry shown Absoiute stereochemistry shown Absente stereochemistry shown Absoute stereochemistry shown Absoute stereochem istry shown Àbsol yte ster-eochemistry shown A b so I u te ste reo c he m i stry s h ow n Rotation ( •+■ ) Ab sol u te ste reo c h e m i st ry show n Absolu te stereochem ïstry s ho wn Absoiute steroochemistry shown Rotation: (-¼} Absolu te .stereocbemîstry shown Rotation (■) Absoiute stereochemistry shown Rotation (4 ) [Revendication 8] Use according to one of the preceding claims, in which R is a linear or branched, saturated, preferably linear saturated, hydrocarbon chain comprising from 6 to 11 carbon atoms, preferably a saturated linear chain of 7 carbon atoms.

9. Use according to one of claims 1 to 3 or 6 to 8, in which the compound is: [Chem. 7] / ""'3 HV" \ / / H

10. 0 Use according to one of claims 1 to 4 or 6 to 9, in which the compound is N-octanoyl-L-homoserine lactone: [Chem. 8] < 1 1 . II *

11. Use according to one of the preceding claims, for preventing and / or reducing at least one cutaneous sign of aging chosen from an appearance of a microrelief of the skin, a formation and / or a presence of fine wrinkles or fine lines, an appearance of roughness, an alteration of the surface appearance of the skin, an alteration of the radiance of the skin complexion, a heterogeneity of the complexion, a loss of elasticity, a loss of suppleness, a loss of firmness, a loss of density, or a loss of tone of the skin, sagging and / or withering of the skin, a thinning of the horny layer of the skin and a papery appearance of the skin, skin dryness.

12. Use according to one of the preceding claims, in which the compound chosen from the compounds of formula (I), the compounds of formula (II), their salts, their solvates and / or their isomers according to the invention, is used in an amount of between 0.001 and 15%, preferably between 0.01 and 12%, even more preferably between 0.01 and 10%.

13. Cosmetic composition comprising, in a physiologically acceptable medium: (i) at least one compound chosen from the compounds of formula (I), the compounds of formula (II), their salts and their stereoisomers, and (ii) at least one additive chosen from organic solvents, hydrophilic or lipophilic gelling agents, fatty substances such as oils, emulsifiers, perfumes, fillers, sunscreens, coloring matters, anti-aging active ingredients, preservatives and mixtures thereof, in which formula (I) is as follows: [Chem.l] (I) Or : - R is a linear or branched, saturated or unsaturated, preferably linear saturated, hydrocarbon chain comprising from 1 to 29 carbon atoms, preferably from 3 to 29 carbon atoms, preferably from 5 to 19 carbon atoms, preferably from 6 to 17 carbon atoms, preferably from 6 to 11 carbon atoms, and said chain being optionally substituted by one or more -OH group(s) and / or interrupted by one or more carbonyl(s) (C=O); and - R2 is chosen from a hydrogen atom, a linear or branched (Cl-C4)alkyl group, preferably linear, substituted or unsubstituted, preferably unsubstituted such as methyl or ethyl, preferably R2 represents a hydrogen atom, and formula (II) is as follows: [Chem. 2] HO (II) Where: - R has the same definition as for formula (I), ie R is a linear or branched, saturated or unsaturated, preferably linear saturated, hydrocarbon chain comprising from 1 to 29 carbon atoms, preferably from 3 to 29 carbon atoms, preferably from 5 to 19 carbon atoms, preferably from 6 to 17 carbon atoms, preferably from 6 to 11 carbon atoms, and said chain being optionally substituted by one or more -OH group(s) and / or interrupted by one or more carbonyl(s) (C=O). ; - R2 has the same definition as for formula (I) ie R2 is chosen from a hydrogen atom, a linear or branched (Cl-C4)alkyl group, preferably linear, substituted or unsubstituted, preferably unsubstituted such as methyl or ethyl, preferably R2 represents a hydrogen atom. and - X is chosen from OR1 or NR2R3: • RI representing a hydrogen or a linear or branched (Cl-C4)alkyl, preferably linear, substituted, in particular by one or more hydroxy or unsubstituted, preferably RI represents a hydrogen; and • NR2R3 represents a primary, secondary or tertiary amine, R2 and R3 identical or different, preferably identical, representing a hydrogen atom, a linear or branched (Cl-C4)alkyl group, preferably linear, substituted, in particular by one or more hydroxy, or unsubstituted, preferably unsubstituted such as methyl or ethyl; preferably R2=R3=H;or R2 and R3 carried by the same nitrogen atom together form a preferably monocyclic heterocycle comprising from 5 to 7 members, preferably 5 to 6 members, saturated or unsaturated, substituted or unsubstituted, and optionally comprising one or more heteroatom(s) identical to or different from that of the nitrogen atom, preferably the heterocycle is chosen from the morpholino, piperazino, piperidino, pyrrolidino groups.;

14. Composition according to claim 13, which has a pH between 6 and 8, preferably between 6.5 and 7.5, preferably around 7

15. / . Cosmetic treatment process for the care of keratin materials, preferably the skin, comprising the application to the keratin materials, preferably the skin, more preferably the skin showing signs of cutaneous aging, of a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound chosen from the compounds of formula (I), the compounds of formula (II), or one of their salts, and / or solvates, and / or isomers.