WO2026040002A1

WO2026040002A1 - Composition and method for caring for the skin

Info

Publication number: WO2026040002A1
Application number: PCT/CN2024/113501
Authority: WO
Inventors: Nan Li
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2024-08-21
Filing date: 2024-08-21
Publication date: 2026-02-26
Anticipated expiration: 2027-02-21
Also published as: FR3165653A3

Abstract

A composition comprising: (i) at least one copper peptide; (ii) at least one C-glycoside; and (iii) laminaria digitata extract. The composition can be used to care for the skin non-therapeutically.

Description

COMPOSITION AND METHOD FOR CARING FOR THE SKIN

TECHNICAL FIELD

The present invention relates to a cosmetic composition. In particular, the present invention relates to a composition for caring for the skin. The present invention also relates to a non-therapeutic method for caring for the skin.

BACKGROUND ART

Human skin is constituted of three compartments, namely a superficial compartment, which is the epidermis, the dermis, and a deep compartment, which is the hypodermis.

The dermis is mainly constituted of fibroblasts and an extracellular matrix (ECM) . This extracellular matrix is constituted of various macromolecules responsible for the mechanical strength of the skin, its suppleness, its tonicity, and its elasticity, and also for physiologically important functions (hydration, thermoregulation and regulation of the permeability of the skin) . These macromolecules include, in particular, collagens, elastin and glycoconjugates (glycoproteins and proteoglycans) .

Collagens represent 70%of the proteins of the ECM. Naturally, collagens are constantly renewed, but this renewal decreases with age, which leads to thinning of the dermis.

A wide variety of cosmetic products have been used to care for the skin, for example, to resist the ageing of the skin by boosting of the production of collagens. However, some cosmetic products on the market are not satisfying on resisting skin ageing.

Thus, there is still a need to formulate a composition for caring for the skin, which can effectively resist skin ageing.

SUMMARY OF THE INVENTION

An object of the present invention is thus to develop a composition for caring for the skin, which can effectively resist skin ageing.

Another object of the present invention is to provide a cosmetic process for caring for the skin.

The inventors have now discovered that the composition in the present invention can effectively resist skin ageing.

Accordingly, in a first aspect, the present invention provides a composition, preferably for caring for the skin, comprising:

(i) at least one peptide copper complex;

(ii) at least one C-glycoside; and

(iii) laminaria digitata extract.

The inventors have found that the composition of the present invention can effectively resist skin ageing by boosting production of collagen I.

In a second aspect, the present invention provides a non-therapeutic method for caring for the skin, comprising applying the composition according to the first aspect of the present invention to the skin.

In a third aspect, the present invention provides a use of the composition according to the first aspect of the present invention for providing anti-aging effect on the skin.

Other subjects and characteristics, aspects and advantages of the present invention will be set forth in the description that follows, and in part, will be obvious from the description, or may be learned by practice of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art the present invention belongs to. When the definition of a term in the present description conflicts with the meaning as commonly understood by those skilled in the art the present invention belongs to, the definition described herein shall apply.

In that which follows and unless otherwise indicated, the limits of a range of values are included within this range, in particular, in the expressions "between . . . and ... " and "ranging from . . . to... " .

Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .

Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well optional, additional, unspecified ones. As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e., “consisting of” ) .

Unless otherwise specified, all numerical values expressing amount of ingredients and the like which are used in the description and claims are to be understood as being modified by the term "about" . Accordingly, unless indicated to the contrary, the numerical values and parameters described herein are approximate values which are capable of being changed according to the desired purpose as required.

For the purposes of the present invention, the term "skin" is intended to cover human skin, including facial skin and the lips. Facial skin is most particularly considered according to the present invention.

All percentages in the present invention refer to weight percentage, unless otherwise specified.

According to the first aspect, the composition of the present invention comprises:

(i) at least one peptide copper complex;

(ii) at least one C-glycoside; and

(iii) laminaria digitata extract.

Peptide copper complexes

According to the first aspect, the composition of the present invention comprises at least one peptide copper complex.

As used herein, the expression “peptide copper complex” generally refers to a coordination compound comprising a peptide molecule and a copper (II) ion non-covalently complexed therewith. As is well understood in the art, copper (II) designates a copper ion having a valence of 2 (i.e., Cu⁺²) . The peptide molecule serves as the complexing agent by donating electrons to the copper ion to yield the non-covalent complex. The peptide molecule is a chain of two or more amino acid units or amino acid derivative units covalently bonded together via amide linkages (for example, -CONH-) , the formation of such linkages being accompanied by the elimination of water.

Generally, an amino acid consists of an amino group, a carboxyl group, a hydrogen atom, and an amino acid side-chain moiety-all bonded, in the case of an alpha-amino acid, to a single carbon atom that is referred to as an alpha-carbon. The amino acid units may be provided by amino acids other than alpha-amino acids. For example, the amino acids may be beta-or gamma-amino acids, such as those shown below.

where X is the amino acid side-chain moiety bonded, along with the amino group and hydrogen, to an alpha-, beta-, or gamma-carbon atom.

As another example, the amino acids include, but are not limited to, naturally occurring alpha-amino acids. Naturally occurring amino acids are those from which the amino acid units of naturally occurring proteins are derived. Some of these amino acids, along with their respective amino acid side-chain moieties, are shown below in Table A. The naturally occurring amino acids shown are all in the L configuration, referring to the optical orientation of the alpha carbon or other carbon atom bearing the amino acid side-chain. A peptide molecule of the present invention may also comprise amino acids that are in the D optical configuration, or a mixture of D and L amino acids.

Table A

Other naturally occurring amino acids include hydroxyproline and gamma-carboxyglutamate.

Representative amino acid derivatives include those set forth in Table B below.

Table B

Histidine derivatives include compounds having the structure:

wherein n=1-20, and Y₁ and Y₂are independently selected from alkyl moieties containing from 1-12 carbon atoms or an aryl moiety containing from 6-12 carbon atoms. In certain embodiments, n is 1, Y₂is methyl, and Y₁ is H (i.e., 3-methyl histidyl) or Y₂is H and Y₁ is methyl (i.e., 5-methyl histidine) .

Similarly, arginine derivatives include compounds having the structure:

where n=1-20 (excluding n=3) .

As used herein, “alkyl” means a straight chain or branched, cyclic or noncyclic, substituted, or unsubstituted, saturated, or unsaturated aliphatic hydrocarbon containing from 1 to 18 carbon atoms. Representative saturated straight chain alkyls include methyl, ethyl, n-propyl and the like, while saturated branched alkyls include isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, and the like. Representative saturated cyclic alkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like; while unsaturated cyclic alkyls include cyclopentenyl, cyclohexenyl, and the like. Unsaturated alkyls contain at least one double or triple bond between adjacent carbon atoms (referred to as an “alkenyl” or “alkynyl, ” respectively) . Representative alkenyls include ethenyl, 1-butenyl, isobutenyl, 2-methyl-2-butenyl, and the like; while representative alkynyls include acetylenyl, 2-butynyl, 3-methyl-1-butynyl, and the like.

Also, as used herein, “aryl” means an aromatic carbocyclic moiety such as phenyl or naphthyl, and may be substituted or unsubstituted. “Arylalkyl, ” as used herein, means an alkyl having at least one alkyl hydrogen atom replaced with a substituted or unsubstituted aryl moiety, such as benzyl (i.e., -CH₂-phenyl, - (CH₂) ₂-phenyl, - (CH₂) ₃-phenyl, -CH (phenyl) ₂, and the like) .

A peptide copper complex of the present invention may have the formula [R₁-R₂-R₃] : copper (II) where R₃ is at least one amino acid or amino acid derivative, as defined above, bonded to R₂by a peptide bond (i.e., -C (═O) NH-) . Where R₃ is a single amino acid or amino acid derivative, then the peptide of the peptide copper complex is generally classified as a tripeptide. As another example of a peptide copper complex of the present invention having the formula [R₁-R₂-R₃] : copper (II) , R₃ is a chemical moiety bonded to the R₂ moiety by an amide bond. The expression “chemical moiety, ” as used herein and with reference to R₃, includes any chemical moiety having an amino group capable of forming an amide bond with the carboxyl terminus of R₂ (i.e., the carboxyl terminus of histidine, arginine, or derivatives thereof) .

As a more particular example, where R₃ is a chemical moiety bonded to the R₂ moiety by an amide bond, R₃ is-NH₂, an alkylamino moiety having from 1-20 carbon atoms, or an arylamino moiety having from 6-20 carbon atoms. As used herein, an “alkylamino moiety” encompasses alkyl moieties containing an amino moiety, wherein the alkyl moiety is as defined above, and includes, but is not limited to, octyl amine and propyl amine. Similarly, an “arylamino moiety” encompasses aryl moieties containing an amino moiety, wherein the aryl moiety is as defined above, and includes, but is not limited to, benzylamine and benzyl- (CH₂) _1-14-amine. Further examples of suitable chemical moieties having amino groups capable of forming an amide linkage with the carboxyl terminus of R₂ include polyamines such as spermine and spermidine.

It should be understood that R₃ may include more than one chemical moiety. For example, additional amino acids or amino acid derivatives may be bonded to the above-described peptide copper complexes comprising tripeptides to yield peptide copper complexes comprising peptides having four or more amino acids and/or amino acid derivatives. For purposes of illustration, Table C, shown below, presents various representative examples of peptide copper complexes used for or comprised in embodiments of the present invention.

Table C

Further examples of peptide copper complexes encompassed in embodiments of the present invention are disclosed in U.S. Pat. Nos. 4,665,054; 4,760,051; 4,767,753; 4,810,693; 4,877,770; 5,023,237; 5,059,588; 5,118,665; 5,120,831; 5,164,367; 5,177,061; 5,214,032; 5,538,945; 5,550,183; and 6,017,888, all of which are incorporated herein by reference in their entirety.

Examples of the peptide copper complex derivatives, encompassed in embodiments of the present invention, include, but are not limited to, those disclosed and described in the above-cited U.S. Patents that are directed to peptide copper complexes, as well as those disclosed and described in the published PCT application having the international publication number WO 94/03482, incorporated herein by reference in its entirety.

Preferably, the peptide in the peptide copper complex comprises at least two amino acid units, preferably three amino acid units, covalently bonded together via amide linkages, and the amino acid units are selected from glycine, alanine, valine, leucine, isoleucine, lysine, arginine, histidine, aspartic acid, glutamic acid, asparagine, glutamine, phenylalanine, tyrosine, tryptophan, cysteine, methionine, serine, threonine, proline, hydroxyproline and gamma-carboxyglutamate.

Preferably, the molar ratio of peptide to copper in the peptide copper complex ranges from about 1: 1 to about 3: 1.

Preferably, the peptide copper complex is selected from glycyl-histidyl-lysine: copper, glycyl-arginyl-lysine: copper, glycyl- (3-methyl) histidyl-lysine: copper, glycyl- (5-methyl) histidyl-lysine: copper, alanyl-histidyl-lysine: copper, alanyl-arginyl-lysine: copper, alanyl- (3-methyl) histidyl-lysine: copper, alanyl- (5-methyl) histidyl-lysine: copper, glycyl-histidyl-phenylalanine: copper, glycyl-arginyl-phenylalanine: copper, glycyl- (3-methyl) histidyl-phenylalanine: copper, glycyl- (5-methyl) histidyl-phenylalanine: copper, alanyl-histidyl-phenylalanine: copper, alanyl-arginyl-phenylalanine: copper, alanyl- (3-methyl) histidyl-phenylalanine: copper, alanyl- (5-methyl) histidyl-phenylalanine: copper, (N-methyl) glycyl-histidyl-lysine: copper, (N-methyl) glycyl-arginyl-lysine: copper, valyl-histidyl-lysine: copper, prolyl-histidyl-lysine: copper, Leucyl-histidyl-lysine: copper, glycyl-D-histidyl-L-lysine: copper, seryl-histidyl-lysine: copper, and combinations thereof.

More preferably, the peptide copper complex is selected from L-alanyl-L-histidyl-L-lysine: copper (II) ( “AHK-Cu” ) , L-valyl-L-histidyl-L-lysine: copper (II) ( “VHK-Cu” ) , glycyl-L-histidyl-L-lysine: copper (II) ( “GHK-Cu” ) , and combinations thereof.

Most preferably, the composition according to the present invention comprises copper tripeptide-1.

Advantageously, the peptide copper complex is present in the composition of the present invention in an amount ranging from 0.00001 wt. %to 10 wt. %, preferably from 0.0005 wt. %to 5 wt. %, more preferably from 0.001 wt. %to 1 wt. %, even more preferably from 0.001 wt. %to 0.5 wt. %, relative to the total weight of the composition.

C-glycosides

According to the first aspect, the composition of the present invention comprises at least one C-glycoside.

Preferably, the C-glycoside is chosen from compounds of formula (I) :

in which:

- R represents a saturated C₁ to C₁₀, in particular C₁ to C₄, alkyl radical 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,

- 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 the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and

- X represents a radical chosen from the–CO-, -CH (OH) -, -CH (NH₂) -, -CH (NHCH₂CH₂CH₂OH) -, -CH (NHPh) -and–CH (CH₃) -groups and in particular a–CO-, -CH (OH) -or–CH (NH₂) -radical and more particularly a–CH (OH) -radical,

the S-CH₂-X bond represents a bond of C-anomeric nature, which can beαorβ, and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers.

The C-glycoside of use for the implementation of the invention are in particular those for which R denotes a saturated linear C₁ to C₆, in particular C₁ to C₄, preferentially C₁ to C₂, alkyl radical and more preferably a methyl radical.

Mention may in particular be made, among the alkyl groups suitable for the implementation of the invention, of the methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl or cyclohexyl groups.

According to one embodiment of the invention, use may be made of a C-glycoside corresponding to the formula (I) for which S can represent a monosaccharide or a polysaccharide comprising up to 6 sugar units, in pyranose and/or furanose form and of L and/or D series, the said mono-or polysaccharide exhibiting at least one necessarily free hydroxyl functional group and/or optionally one or more necessarily protected amine functional groups, X and R otherwise retaining all of the definitions given above.

Advantageously, a monosaccharide of the invention can be chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose or L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine or 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 comprising up to 6 sugar units can 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 or N-acetyl-D-glucosamine, an oligosaccharide comprising at least one xylose which can 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 via a 1-4 bond.

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

Preferably, use is made of a C-glycoside of formula (I) for which:

- R denotes an unsubstituted linear C₁-C₄, in particular C₁-C₂, alkyl radical, especially a methyl radical;

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

- X represents a group chosen from-CO-, -CH (OH) -or-CH (NH₂) -and preferably a-CH (OH) -group.

The acceptable salts of the compounds described in the present invention comprise conventional non-toxic salts of the said compounds, such as those formed from organic or inorganic acids. Mention may be made, by way of example, of the salts of inorganic acids, such as sulfuric acid, hydrochloric acid. Mention may also be made of the salts of organic acids, which can comprise one or more carboxylic, sulfonic or phosphonic acid groups. Mention may in particular be made of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.

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

The solvates which are acceptable for the compounds described in the present invention comprise conventional solvates, such as those formed during the final stage of preparation of the said compounds due to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.

Of course, according to the invention, a C-glycoside corresponding to the formula (I) can be used alone or as a mixture with other C-glycoside and in any proportion.

A C-glycoside which is suitable for the invention can in particular be obtained by the synthetic method described in the document WO02/051828.

Mention may in particular be made, by way of non-limiting illustration of the C-glycoside compounds which are particularly suitable for the invention, of the following compounds:

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

-C-α-D-xylopyranoside-n-propan-2-one,

-C-β-D-xylopyranoside-2-hydroxypropane,

-C-α-D-xylopyranoside-2-hydroxypropane,

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

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

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

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

-1- (C-β-D-fucopyranoside) -2-hydroxypropane,

-1- (C-α-D-fucopyranoside) -2-hydroxypropane,

-1- (C-β-L-fucopyranoside) -2-hydroxypropane,

-1- (C-α-L-fucopyranoside) -2-hydroxypropane,

-1- (C-β-D-glucopyranosyl) -2-hydroxypropane,

-1- (C-α-D-glucopyranosyl) -2-hydroxypropane,

-1- (C-β-D-galactopyranosyl) -2-hydroxypropane,

-1- (C-α-D-galactopyranosyl) -2-hydroxypropane,

-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-propane-2-one,

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

-C-β-D-maltopyranoside-2-hydroxypropane,

-C-α-D-maltopyranoside-2-hydroxypropane, their isomers and their mixtures.

According to one embodiment, C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane and better still C-β-D-xylopyranoside-2-hydroxypropane can advantageously be used for the composition according to the invention.

Most preferably, the composition according to the present invention comprises C-β-D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) .

Advantageously, the C-glycoside is present in the composition according to the present invention in an amount ranging from 0.01 wt. %to 20 wt. %, preferably from 0.05 wt. %to 15 wt. %, more preferably from 0.1 wt. %to 10 wt. %, even more preferably from 0.2 wt. %to 5 wt. %, relative to the total weight of the composition.

Laminaria digitata extract

According to the first aspect, the composition of the present invention comprises laminaria digitata extract.

Laminaria digitate is a brown alga rich in iodine and sodium, dark brown in color and large in size. It is found in cold seas and oceans, particularly in the North Sea and the North Atlantic. It is found in abundance along the coasts of Great Britain and Ireland, Iceland and Russia and Brittany.

Laminaria digitata extract is preferably obtained by leaching with water, filtration, and concentration by reverse osmosis.

As an example of commercial products of laminaria digitata extract, mention can be made of that sold under the name of PHYCOJUVENINE DIG ALG147 by the company CODIF.

Advantageously, laminaria digitata extract is present in the composition of the present invention in an amount ranging from 0.00001 wt. %to 10 wt. %, preferably from 0.00005 wt. %to 5 wt. %, more preferably from 0.0001 wt. %to 2 wt. %, even more preferably from 0.0002 wt. %to 0.5 wt. %, relative to the total weight of the composition.

The inventors have found that the combination of (i) at least one peptide copper complex; (ii) at least one C-glycoside; and (iii) laminaria digitata extract can result in a synergetic effect on production of collagen I.

Advantageously, the weight ratio of peptide copper complex: C-glycoside: laminaria digitata extract is 1: 1-500: 0.01-1, preferably 1: 10-400: 0.02-0.5.

Aqueous phase

The composition of the present invention may comprise an aqueous phase.

Preferably, the aqueous phase comprises water.

Advantageously, water is present in the composition of the present invention in an amount ranging from 50 wt. %to 99.99 wt. %, preferably from 70 wt. %to 99.99 wt. %, more preferably from 80 wt. %to 99.60 wt. %, relative to the total weight of the composition.

Optionally, the aqueous phase comprises an organic solvent miscible with water (at room temperature 25℃) selected from monoalcohols, glycols and polyols having from 2 to 20 carbon atoms, such as octyldodecanol, glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and mixtures thereof.

Advantageously, the aqueous phase is present in the composition of the present invention in an amount ranging from 60 wt. %to 99.99 wt. %, preferably from 70 wt. %to 99.99 wt. %, more preferably from 80 wt. %to 99.60 wt. %, relative to the total weight of the composition.

Additional cosmetic active ingredients

The composition of the present invention may comprise an additional cosmetic active ingredient in addition to the cosmetic active ingredients as defined previously.

The skilled in the art can adjust the type and their amount of the additional cosmetic active ingredients based on the final use of the composition according to the present invention.

Additional adjuvants or additives

The composition of the present invention may comprise may also contain conventional cosmetic adjuvants or additives, for instance fragrances, chelating agents, preserving agents and bactericides, surfactants, thickeners, pH regulators, and mixtures thereof.

The skilled in the art can select the amount of the additional adjuvants or additive so as not to adversely impact the final use of the composition according to the present invention.

According to a preferred embodiment, the present invention provides a composition comprising, relative to the total weight of the composition:

(i) from 0.001 wt. %to 1 wt. %of copper tripeptide-1;

(ii) from 0.1 wt. %to 10 wt. %of hydroxypropyl tetrahydropyrantriol; and

(iii) from 0.0001 wt. %to 2 wt. %of laminaria digitata extract.

According to a particularly preferred embodiment, the present invention provides a composition comprising, relative to the total weight of the composition:

(i) from 0.001 wt. %to 0.5 wt. %of copper tripeptide-1;

(ii) from 0.2 wt. %to 5 wt. %of hydroxypropyl tetrahydropyrantriol; and

(iii) from 0.0002 wt. %to 0.5 wt. %of laminaria digitata extract.

Galenic form and method

The composition of the present invention is in the form of emulsion, cream, lotion, or hydrogel, and can be sued as toner, lotion, light cream, nourish cream, sleeping mask, or eye cream.

The composition of the present invention can be used for caring for the skin. In particular, the composition of the present invention can deliver anti-ageing effect to the skin.

According to the second aspect, the present invention provides a non-therapeutic method for caring for the skin, comprising applying the composition according to the first aspect of the present invention to the skin.

In some embodiments, the present invention provides a non-therapeutic method for anti-aging of the skin, comprising applying the composition according to the first aspect of the present invention to the skin.

EXAMPLES

The examples that follow are given as non-limiting illustrations of the present invention.

Main raw materials used, trade names and suppliers thereof are listed in Table 1.

Table 1

Invention Example 1 and Comparative Examples 1-2

Compositions of invention example (IE) 1 and comparative examples (CE) 1-2 were prepared based on the amounts of components given in Table 2. The amounts are given by weight percentage of each component relative to the total weight of the composition, wherein AM stands for active material.

Table 2

Composition of invention example 1 represents composition according to the present invention.

Composition of comparative example 1 does not comprise at least one C-glycoside and laminaria digitata extract.

Composition of comparative example 2 does not comprise at least one copper peptide.

Preparation process:

The compositions listed above were prepared as follows: adding copper tripeptide-1, hydroxypropyl tetrahydropyrantriol, and laminaria digitata extract according to corresponding amounts in Table 2 slowing into water with stirring under room temperature to obtain a homogeneous mixture.

Evaluation

The effect of compositions prepared above on production of collagen I was tested as follows.

1) cell inoculation:

Fibroblasts were revived, and when the laying rate reaches about 60%, the cells were seeded into 6-well plates and cultured overnight in an incubator with CO₂ (37 ℃, 5%CO₂) .

2) Solution preparation:

The working solutions were prepared according to the test groups listed in Table 3.

Table 3

3) Administration:

The groups were administered according to Table 3. Culture medium was added to each well for the blank control group and the negative control group. The same volume of culture medium containing TGF-β1 was added to each well for the positive control group. The same volume of culture solution containing corresponding concentration of active ingredients in the culture medium was added to each well for the testing sample groups.

4) UVA irradiation: all groups except for the blank control group were subjected to UVA irradiation. After irradiation, they were placed in an incubator with CO₂ (37 ℃, 5%CO₂) for further cultivation.

5) Immunofluorescence detection and gene expression detection were performed.

Enhancement rates were calculated according to the following equations:

Enhancement rate (%) = (the testing group-NC group) /NC group*100%

6) Result statistics and analysis: GraphPad Prism was used for plotting, and results were expressed as Mean±SD. Comparisons between groups were made using t-test statistical analysis. As compared with the BC group, significance is represented by#, p-value<0.05 is represented by#, p-value<0.01 is represented by##; as compared with the NC group, significance is represented by*, p-value<0.05 is represented by*, and p-value<0.01 is represented by**.

The PCR data of collagen I were summarized in Table 4.

Table 4

It can be seen from Table 4 that composition of invention example 1 shows better boost effect on production of collagen I as compared with compositions of comparative examples 1 and 2, the combination of at least one copper peptide, at least one C-glycoside, and laminaria digitata extract can result in a synergetic effect on production of collagen I.

Claims

A composition comprising:

(i) at least one peptide copper complex;

(ii) at least one C-glycoside; and

(iii) laminaria digitata extract.
The composition according to claim 1, wherein the peptide in the peptide copper complex comprises at least two amino acid units, preferably three amino acid units, covalently bonded together via amide linkages, and the amino acid units are selected from glycine, alanine, valine, leucine, isoleucine, lysine, arginine, histidine, aspartic acid, glutamic acid, asparagine, glutamine, phenylalanine, tyrosine, tryptophan, cysteine, methionine, serine, threonine, proline, hydroxyproline and gamma-carboxyglutamate, preferably the molar ratio of peptide to copper in the peptide copper complex ranges from 1: 1 to 3: 1.
The composition according to claim 1 or 2, wherein the peptide copper complex is selected from glycyl-histidyl-lysine: copper, glycyl-arginyl-lysine: copper, glycyl- (3-methyl) histidyl-lysine: copper, glycyl- (5-methyl) histidyl-lysine: copper, alanyl-histidyl-lysine: copper, alanyl-arginyl-lysine: copper, alanyl- (3-methyl) histidyl-lysine: copper, alanyl- (5-methyl) histidyl-lysine: copper, glycyl-histidyl-phenylalanine: copper, glycyl-arginyl-phenylalanine: copper, glycyl- (3-methyl) histidyl-phenylalanine: copper, glycyl- (5-methyl) histidyl-phenylalanine: copper, alanyl-histidyl-phenylalanine: copper, alanyl-arginyl-phenylalanine: copper, alanyl- (3-methyl) histidyl-phenylalanine: copper, alanyl- (5-methyl) histidyl-phenylalanine: copper, (N-methyl) glycyl-histidyl-lysine: copper, (N-methyl) glycyl-arginyl-lysine: copper, valyl-histidyl-lysine: copper, prolyl-histidyl-lysine: copper, Leucyl-histidyl-lysine: copper, glycyl-D-histidyl-L-lysine: copper, seryl-histidyl-lysine: copper, and combinations thereof, preferably selected from L-alanyl-L-histidyl-L-lysine: copper (II) , L-valyl-L-histidyl-L-lysine: copper (II) , glycyl-L-histidyl-L-lysine: copper (II) , and combinations thereof; more preferably the peptide copper complex is copper tripeptide-1.
The composition according to any of claims 1 to 3, wherein the peptide copper complex is present in an amount ranging from 0.00001 wt. %to 10 wt. %, preferably from 0.0005 wt. %to 5 wt. %, more preferably from 0.001 wt. %to 1 wt. %, even more preferably from 0.001 wt. %to 0.5 wt. %, relative to the total weight of the composition.
The composition according to any of claims 1 to 4, wherein the C-glycoside is chosen from compounds of formula (I) :

in which:

- R represents a saturated C₁ to C₁₀, in particular C₁ to C₄, alkyl radical 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,

- 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 the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and

- X represents a radical chosen from the–CO-, -CH (OH) -, -CH (NH₂) -, -CH (NHCH₂CH₂CH₂OH) -, -CH (NHPh) -and–CH (CH₃) -groups and in particular a–CO-, -CH (OH) -or–CH (NH₂) -radical and more particularly a–CH (OH) -radical,

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

and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers.
The composition according to any of claims 1 to 5, wherein 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-hydroxypropane,

- C-α-D-xylopyranoside-2-hydroxypropane,

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

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

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

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

- 1- (C-β-D-fucopyranoside) -2-hydroxypropane,

- 1- (C-α-D-fucopyranoside) -2-hydroxypropane,

- 1- (C-β-L-fucopyranoside) -2-hydroxypropane,

- 1- (C-α-L-fucopyranoside) -2-hydroxypropane,

- 1- (C-β-D-glucopyranosyl) -2-hydroxypropane,

- 1- (C-α-D-glucopyranosyl) -2-hydroxypropane,

- 1- (C-β-D-galactopyranosyl) -2-hydroxypropane,

- 1- (C-α-D-galactopyranosyl) -2-hydroxypropane,

- 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-propane-2-one,

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

- C-β-D-maltopyranoside-2-hydroxypropane,

- C-α-D-maltopyranoside-2-hydroxypropane,

their isomers and their mixtures.
The composition according to any of claims 1 to 6, wherein the C-glycoside is present in an amount ranging from 0.01 wt. %to 20 wt. %, preferably from 0.05 wt. %to 15 wt. %, more preferably from 0.1 wt. %to 10 wt. %, even more preferably from 0.2 wt. %to 5 wt. %, relative to the total weight of the composition.
The composition of any of claims 1 to 7, wherein laminaria digitata extract is present in an amount ranging from 0.00001 wt. %to 10 wt. %, preferably from 0.00005 wt. %to 5 wt. %, more preferably from 0.0001 wt. %to 2 wt. %, even more preferably from 0.0002 wt. %to 0.5 wt. %, relative to the total weight of the composition.
The composition according to claim 1, comprising, relative to the total weight of the composition:

(i) from 0.001 wt. %to 0.5 wt. %of copper tripeptide-1;

(ii) from 0.2 wt. %to 5 wt. %of hydroxypropyl tetrahydropyrantriol; and

(iii) from 0.0002 wt. %to 0.5 wt. %of laminaria digitata extract.
The composition according to any one of claims 1 to 9, further comprising water, preferably in an amount ranging from 50 wt. %to 99.99 wt. %, preferably from 70 wt. %to 99.99 wt. %, more preferably from 80 wt. %to 99.60 wt. %, relative to the total weight of the composition.
The composition according to any one of claims 1 to 10, wherein the weight ratio of peptide copper complex: C-glycoside: laminaria digitata extract is 1: 1-500: 0.01-1, preferably 1: 10-400: 0.02-0.5.
A non-therapeutic method for caring for the skin, comprising applying the composition according to any of claims 1 to 11 to the skin.
A use of the composition according to any of claims 1 to 11 for providing anti-aging effect on the skin.