Composition and method for caring for keratin materials
A composition of C-glycosides, aminosugars, and Inonotus obliquus extract addresses skin ageing by enhancing LGI3 expression, offering improved skin care and anti-ageing benefits through enhanced keratinocyte function.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- LOREAL SA
- Filing Date
- 2024-10-25
- Publication Date
- 2026-04-30
AI Technical Summary
Existing cosmetic products are inadequate in effectively resisting skin ageing due to deficiencies in keratinocyte differentiation and protein matrix, increased metalloproteinases, and decreased glycosaminoglycan synthesis, necessitating a composition that enhances Leucine-Rich Glioma Inactivated 3 (LGI3) expression for improved skin protection.
A composition comprising C-glycosides, aminosugars, and Inonotus obliquus extract is formulated to enhance LGI3 expression in keratinocytes, promoting skin care and anti-ageing benefits.
The composition synergistically enhances LGI3 gene expression, providing effective resistance against skin ageing by improving keratinocyte function and skin health.
Smart Images

Figure PCTCN2024127210-FTAPPB-I100001 
Figure PCTCN2024127210-FTAPPB-I100002 
Figure PCTCN2024127210-FTAPPB-I100003
Abstract
Description
COMPOSITION AND METHOD FOR CARING FOR KERATIN MATERIALSTECHNICAL FIELD
[0001] The present invention relates to a composition. In particular, the present invention relates to a composition for caring for keratin materials. The present invention also relates to a non-therapeutic method for caring for keratin materials.BACKGROUND ART
[0002] The skin is the protective barrier for the human body. It protects the interior of the body from physical injury (such as trauma) and biological injury (such as bacteria, viruses, or fungi) . The epidermis is a keratinized stratified pavimentous epithelium. Its mean thickness ranges from 60 to 100μm and may reach 600 to 700μm on the sole of the feet and the palm of the hands. It consists mainly of keratinocytes, but also other cells, and rests on a basal membrane that separates it from the dermis.
[0003] The main changes concerning the dermis are a decrease in the collagen content and in the thickness of the dermis.
[0004] The main changes concerning the epidermis are a decrease in keratinocyte differentiation, resulting in a deficit in the proteins matrix of the cornified cell, an increase in metalloproteinases, which are proteases that degrade the extracellular matrix and that participate in ageing of the skin, and also a decrease in the synthesis of various glycosaminoglycans.
[0005] Based on the recent research progress published in scientific literatures, Leucine-Rich Glioma Inactivated 3 (LGI3) emerged as a rather novel yet promising target with potential skin barrier differentiation benefits. Studies have demonstrated that enhancing the expression of LGI3 can help the skin protection against UV radiation as well.
[0006] A wide variety of cosmetic products have been used to care for the skin, for example, to resist the ageing of the skin. However, some cosmetic products for resisting skin ageing on the market are not satisfying on their efficacy.
[0007] 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
[0008] An object of the present invention is thus to develop a composition for caring for the skin, which can effectively resist skin ageing.
[0009] Another object of the present invention is to provide a cosmetic process for caring for keratin materials.
[0010] Accordingly, in a first aspect, the present invention provides a composition, comprising:
[0011] (i) at least one C-glycoside;
[0012] (ii) at least one aminosugar; and
[0013] (iii) at least one Inonotus obliquus extract.
[0014] The inventors have found that the composition of the present invention can enhance LGI3 expression in keratinocytes production and thus can be used to resist ageing of keratin materials.
[0015] In a second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
[0016] 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
[0017] 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.
[0018] 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... " .
[0019] Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .
[0020] 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” ) .
[0021] 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.
[0022] For the purposes of the present invention, the term "keratin materials" is intended to cover human skin, including facial skin and the lips. Facial skin is most particularly considered according to the present invention.
[0023] All percentages in the present invention refer to weight percentage, unless otherwise specified.
[0024] According to the first aspect, the composition of the present invention comprises:
[0025] (i) at least one C-glycoside;
[0026] (ii) at least one aminosugar; and
[0027] (iii) at least one Inonotus obliquus extract.
[0028] C-glycosides
[0029] According to the first aspect, the composition of the present invention comprises at least one C-glycoside.
[0030] Preferably, the C-glycoside is chosen from compounds of formula (I) :
[0031] in which:
[0032] - 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,
[0033] - 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
[0034] - 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,
[0035] 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.
[0036] 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.
[0037] 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.
[0038] 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.
[0039] 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.
[0040] 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.
[0041] 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.
[0042] Preferably, use is made of a C-glycoside of formula (I) for which:
[0043] - R denotes an unsubstituted linear C1-C4, in particular C1-C2, alkyl radical, especially a methyl radical;
[0044] - 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;
[0045] - X represents a group chosen from-CO-, -CH (OH) -or-CH (NH2) -and preferably a-CH (OH) -group.
[0046] 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.
[0047] 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 of2-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.
[0048] 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.
[0049] 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.
[0050] A C-glycoside which is suitable for the invention can in particular be obtained by the synthetic method described in the document WO02 / 051828.
[0051] 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:
[0052] - C-β-D-xylopyranoside-n-propane-2-one,
[0053] - C-α-D-xylopyranoside-n-propan-2-one,
[0054] - C-β-D-xylopyranoside-2-hydroxypropane,
[0055] - C-α-D-xylopyranoside-2-hydroxypropane,
[0056] - 1- (C-β-D-fucopyranoside) propan-2-one,
[0057] - 1- (C-α-D-fucopyranoside) propan-2-one,
[0058] - 1- (C-β-L-fucopyranoside) propan-2-one,
[0059] - 1- (C-α-L-fucopyranoside) propan-2-one,
[0060] - 1- (C-β-D-fucopyranoside) -2-hydroxypropane,
[0061] - 1- (C-α-D-fucopyranoside) -2-hydroxypropane,
[0062] - 1- (C-β-L-fucopyranoside) -2-hydroxypropane,
[0063] - 1- (C-α-L-fucopyranoside) -2-hydroxypropane,
[0064] - 1- (C-β-D-glucopyranosyl) -2-hydroxypropane,
[0065] - 1- (C-α-D-glucopyranosyl) -2-hydroxypropane,
[0066] - 1- (C-β-D-galactopyranosyl) -2-hydroxypropane,
[0067] - 1- (C-α-D-galactopyranosyl) -2-hydroxypropane,
[0068] - 1- (C-β-D-fucofuranosyl) propan-2-one,
[0069] - 1- (C-α-D-fucofuranosyl) propan-2-one,
[0070] - 1- (C-β-L-fucofuranosyl) propan-2-one,
[0071] - 1- (C-α-L-fucofuranosyl) propan-2-one,
[0072] - C-β-D-maltopyranoside-n-propane-2-one,
[0073] - C-α-D-maltopyranoside-n-propan-2-one,
[0074] - C-β-D-maltopyranoside-2-hydroxypropane,
[0075] - C-α-D-maltopyranoside-2-hydroxypropane, their isomers and their mixtures.
[0076] 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.
[0077] Most preferably, the composition according to the present invention comprises C-β-D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) .
[0078] Advantageously, the C-glycoside is present in the composition according to the present invention in an amount ranging from 0.0001 wt. %to 20 wt. %, preferably from 0.001 wt. %to 15 wt. %, more preferably from 0.01 wt. %to 10 wt. %, even more preferably from 0.02 wt. %to 5 wt. %, relative to the total weight of the composition.
[0079] Aminosugars
[0080] According to the first aspect, the composition according to the present invention comprises at least one aminosugar.
[0081] As used herein, the term aminosugar means a sugar derivative formed by replacing a hydroxyl group with an amino group in a monosaccharide molecule.
[0082] The aminosugar useful in the composition according to the present invention can be a natural aminosugar or a synthetic or semisynthetic aminosugar.
[0083] The term aminosugar is also used herein to encompass aminosugars that may have been chemically modified yet retain their function. Such chemical modifications include but are not limited to esterification, sulfation, polysulfation, acetylation, and methylation. Preferably, the chemical modifications are carried out on the amino group.
[0084] Preferably, the aminosugar is selected from glucosamine, D-glucosamine, GDP-glucosamine, mannosamine, UDP-glucosamine, N-cbz-D-glucosamine, galactosamine, D-glucosamine hydrochloride, glucosamine sulfate, glucosamine phosphate, D-Glucosamine-oxime HCI, 6-desoxy-D-glucosamine, N-methyl-D-glucosamine, N-propyl-D-glucosamine, N-octyl-D-glucosamine, N-butyryl-D-glucosamine, N-boc-D-glucosamine, N-hexanoyl-D-glucosamine, N-acetyl-D-glucosaminic acid, N-acetyl-D-glucosamine, N-acetyl galactosamine, N-alloc glucosamine, N-benzoyl-D-glucosamine, N-butanoyl-D-glucosamine, N-propanoyl-D-glucosamine, pentaacetyl-D-glucosamine, N-Valeryl-D-glucosamine, N-octanoyl-D-glucosamine, and combinations thereof.
[0085] More preferably, the aminosugar is selected from N-boc-D-glucosamine, N-hexanoyl-D-glucosamine, N-acetyl-D-glucosaminic acid, N-acetyl-D-glucosamine, N-acetyl galactosamine, N-alloc glucosamine, N-benzoyl-D-glucosamine, N-butanoyl-D-glucosamine, N-propanoyl-D-glucosamine, pentaacetyl-D-glucosamine, N-Valeryl-D-glucosamine, N-octanoyl-D-glucosamine, and combinations thereof.
[0086] Even more preferably, the aminosugar is selected from N-boc-D-glucosamine, N-hexanoyl-D-glucosamine, N-acetyl-D-glucosamine, N-alloc glucosamine, N-benzoyl-D-glucosamine, N-butanoyl-D-glucosamine, N-propanoyl-D-glucosamine, N-Valeryl-D-glucosamine, N-octanoyl-D-glucosamine, and combinations thereof.
[0087] Even more preferably, the composition according to the present invention comprises N-acetyl-D-glucosamine.
[0088] Advantageously, the aminosugar is present in the composition according to the present invention in an amount ranging from 0.00001 wt. %to 10 wt. %, preferably from 0.0001 wt. %to 5 wt. %, more preferably from 0.0002 wt. %to 3 wt. %, even more preferably from 0.0003 wt. %to 2 wt. %, relative to the total weight of the composition.
[0089] Inonotus obliquus extracts
[0090] According to the first aspect, the composition according to the present invention comprises at least one Inonotus obliquus extract.
[0091] The fungus Inonotus obliquus is a basidiomycete fungus of the Hymenochaetaceae family known under the name chaga or clinker polypore. It is found on birch bark, in several regions worldwide, notably in Russia, Canada and Eastern Europe.
[0092] The Inonotus obliquus extract may be extracted from the whole fungus or from one or more parts of the fungus.
[0093] The Inonotus obliquus extract may be obtained via any extraction method known to those skilled in the art, chosen from hot decoction, milling including ultrasonic milling, using a mixer, maceration, extraction in water under subcritical conditions or extraction using a solvent.
[0094] The extraction pressure will be between 10 MPa (100 bar) and 25 MPa (250 bar) , preferably between 15 and 22.1 MPa (between 150 and 221 bar) .
[0095] The extraction may be performed using dry or fresh matter, advantageously dry matter, in an amount of from 0.1 wt. %to 20 wt. %, preferably from 1 wt. %to 10 wt. %, very preferably from 5 wt. %to 10 wt. %, relative to the total weight of the matter and of the extraction solvent.
[0096] The extraction may be performed at a temperature ranging from 4℃ to 300℃, including room temperature, that is to say a temperature of20℃.
[0097] The extraction may be performed for a period of from a few seconds to 24 hours, preferably from 1 minute to 12 hours, more preferably for a period of from 5 minutes to 5 hours, and more preferably for a period of from 15 minutes to 2 hours.
[0098] The solvent may be chosen from water, or a solvent mixture, preferably a polar protic solvent, and preferably in water, an alcohol, a glycol, a polyol, a water / alcohol, water / glycol or water / polyol mixture (such as water mixed with ethanol, glycerol and / or butylene glycol and / or other glycols such as xylitol and / or propanediol, etc. ) , from 99 / 1 to 1 / 99 (w / w) , preferably in water as sole solvent.
[0099] Preferably, the Inonotus obliquus extract is an extract obtained by aqueous extraction. For the purposes of the present invention, the expression “extract obtained by aqueous extraction” means any extract obtained by extraction with an aqueous solution containing more than 60 wt. %, preferably at least 70 wt. %, more preferably at least 80 wt. %, still more preferably at least 90 wt. %, even more preferably at least 95 wt. %, of water relative to the total weight of the aqueous solution, even more preferably not containing glycol, still more preferably only containing water.
[0100] Preferably, the extraction may be performed in the presence of a nonionic surfactant, preferably chosen from lauryl glucoside sold under the name 1200UP by BASF or else caprylyl / capryl glucoside ( 810 UP) . The weight concentration of the nonionic surfactant may be between 0.5 wt. %and 5 wt. %, preferably between 0.5 wt.%and 1 wt. %; more preferably, it will be 1wt. %, relative to the total weight of the extract.
[0101] Preferably, the extraction will be performed in water under subcritical conditions.
[0102] The term extraction under “subcritical conditions” means extraction in the presence of water, under temperature conditions of greater than 100℃ and pressure conditions of less than 22.1 MPa (221 bar) , such that the water remains in the liquid state but has a viscosity and a surface tension lower than that of water at room temperature, increasing its dielectric constant.
[0103] Preferably, the composition comprises an extract from the whole fungus.
[0104] Advantageously, the Inonotus obliquus extract is present in the composition according to the present invention in an amount ranging from 0.00001 wt. %to 10 wt. %, preferably from 0.0001 wt. %to 5 wt. %, more preferably from 0.0002 wt. %to 3 wt. %, even more preferably from 0.0003 wt. %to 2 wt. %, relative to the total weight of the composition.
[0105] Advantageously, the weight ratio of the Inonotus obliquus extract to the C-glycoside is from 1: 50 to 1: 1, preferably from 1: 40 to 1: 2, more preferably from 1: 35 to 1: 3.
[0106] Advantageously, the weight ratio of the Inonotus obliquus extract to the aminosugar is from 1: 10 to 10: 1, preferably from 1: 5 to 5: 1, more preferably from 1: 2 to 2: 1.
[0107] Aqueous phase
[0108] The composition of the present invention may comprise an aqueous phase.
[0109] Preferably, the aqueous phase comprises water.
[0110] 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 99.99 wt. %, relative to the total weight of the composition.
[0111] 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.
[0112] 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 99.99 wt. %, relative to the total weight of the composition.
[0113] Additional cosmetic active ingredients
[0114] The composition of the present invention may comprise an additional cosmetic active ingredient in addition to the cosmetic active ingredients as defined previously.
[0115] 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.
[0116] Additional adjuvants or additives
[0117] 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, thickeners, surfactants, pH regulators, and combinations thereof.
[0118] 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.
[0119] According to a particularly preferred embodiment, the present invention provides a composition comprising, relative to the total weight of the composition:
[0120] (i) from 0.02 wt. %to 5 wt. %of hydroxypropyl tetrahydropyrantriol;
[0121] (ii) from 0.0003 wt. %to 2 wt. %of at least one aminosugar selected from N-boc-D-glucosamine, N-hexanoyl-D-glucosamine, N-acetyl-D-glucosamine, N-alloc glucosamine, N-benzoyl-D-glucosamine, N-butanoyl-D-glucosamine, N-propanoyl-D-glucosamine, N-Valeryl-D-glucosamine, N-octanoyl-D-glucosamine, and combinations thereof; and
[0122] (iii) from 0.0003 wt. %to 2 wt. %of at least one Inonotus obliquus extract.
[0123] Galenic form and method
[0124] The composition of the present invention can be 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.
[0125] The composition of the present invention can be used for caring for keratin materials. In particular, the composition of the present invention can deliver an anti-ageing effect on the skin.
[0126] According to the second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
[0127] In particular, the keratin material is the skin.
[0128] In some embodiments, the present invention provides a non-therapeutic method for resisting ageing of the skin, comprising applying the composition according to the first aspect of the present invention to the skin.
[0129] EXAMPLES
[0130] The examples that follow are given as non-limiting illustrations of the present invention.
[0131] Main raw materials used, trade names and suppliers thereof are listed in Table 1.
[0132] Table 1
[0133] Invention Example 1 and Comparative Examples 1-4
[0134] Compositions of invention example (IE) 1 and comparative examples (CE) 1-4 were prepared based on the amounts of components given in Table 2. The amounts are given by weight in ppm or percentage of each component relative to the total weight of the composition, wherein AM stands for active material.
[0135] Table 2
[0136] Composition of invention example 1 represents composition according to the present invention.
[0137] Composition of comparative example 1 does not comprise at least one aminosugar and at least one Inonotus obliquus extract.
[0138] Composition of comparative example 2 does not comprise at least one C-glycoside and at least one Inonotus obliquus extract.
[0139] Composition of comparative example 3 does not comprise at least one C-glycoside and at least one at least one aminosugar.
[0140] Composition of comparative example 4 does not comprise at least one Inonotus obliquus extract.
[0141] Preparation process:
[0142] The compositions listed above were prepared as follows: adding hydroxypropyl tetrahydropyrantriol (if any) , acetyl glucosamine (if any) , and Inonotus obliquus extract (if any) according to corresponding amounts in Table 2 slowing into water with stirring under room temperature to obtain a homogeneous mixture.
[0143] Evaluation:
[0144] The anti-ageing effect of compositions prepared above was evaluated by detecting the LGI3 gene expression level.
[0145] The cells used in the test is human primary keratinocytes isolated from foreskin (Episkin) .
[0146] The cell culture medium used in the test is EpiLife medium with low calcium (60μM) and S7 animal-free supplement from Life Technologies.
[0147] In particular, the test was carried out as follows.
[0148] 1) cell inoculation
[0149] Keratinocytes were cultured in the culture medium under 37℃ and 5%CO2.
[0150] 2) Solution preparation
[0151] The working solutions were prepared by dispersing hydroxypropyl tetrahydropyrantriol, acetyl glucosamine, and Inonotus obliquus extract in the culture medium according to the test groups listed in Table 3.
[0152] Table 3
[0153] 3) Administration
[0154] Upon reaching 80%confluence, the culture medium was refreshed with working solutions described in Table 3. Fresh medium was added to control treatment cells. The cells were then incubated with the treatment for 24 hours, before harvested af ter 3 times of wash with Dulbecco’s phosphate buffer saline (DPBS, Thermo Fisher) .
[0155] 4) Cell tolerance to the treatments
[0156] Preliminary experiments were conducted to ensure the testing dosage was not toxic to the cells, which was validated by adding MTT reagent (Sigma-Aldrich) to the cells at 1.0 mg / mL concentration in fresh medium to quantify cell viability with colorimetric readings of isopropanol extracted formazan formed.
[0157] 5) Cellular mRNA extraction
[0158] The harvested cells were processed with TRIzol reagent (Invitrogen) to extract mRNA according to the manufacturer’s protocol. The extracted RNA was subsequently measured by Bioanalyzer to ensure quality and quantity. Then the extracted RNA was purified using RNeasy kits (Qiagen) with the quality verified by a Bioanalyzer 2100 (Agilent) .
[0159] 6) RNA sequencing for transcriptomic analyses
[0160] The mRNA samples obtained above was then subjected to standard Illumina stranded mRNA library preparation, followed by sequencing using a Hiseq platform (Illumina) .
[0161] Raw data was then processed with StringTie to match transcripts with LGI3 gene, with the quantitative transcript count indicated as FPKM (Fragments Per Kilobase of transcript per Million fragments mapped) , which indicates thousand base pairs per 1 million mapped fragments.
[0162] The FPKM values for different treatments were compared with each other using analysis of variances (ANOVA) . P-values for comparisons with the control group was used to judge the significance of difference for each treatment.
[0163] The LGI3 gene expression level and p-values compared with the control group were summarized in Table 4.
[0164] Table 4
[0165] It can be seen from Table 4 that composition of invention example 1 shows better boost effect on the LGI3 gene expression level as compared with compositions of comparative examples 1-4, the combination of at least one C-glycoside, at least one aminosugar and at least one Inonotus obliquus extract can result in a synergetic effect on the LGI3 gene expression level, and therefore on anti-ageing of keratin materials, in particular the skin.
Claims
1.A composition comprising:(i) at least one C-glycoside;(ii) at least one aminosugar; and(iii) at least one Inonotus obliquus extract.2.The composition according to claim 1, 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.3.The composition according to claim 1, 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.4.The composition according to any of claims 1 to 3, wherein the C-glycoside is present in an amount ranging from 0.0001 wt. %to 20 wt. %, preferably from 0.001 wt. %to 15 wt. %, more preferably from 0.01 wt. %to 10 wt. %, even more preferably from 0.02 wt. %to 5 wt. %, relative to the total weight of the composition.5.The composition according to any of claims 1 to 4, wherein the aminosugar is selected from glucosamine, D-glucosamine, GDP-glucosamine, mannosamine, UDP-glucosamine, N-cbz-D-glucosamine, galactosamine, D-glucosamine hydrochloride, glucosamine sulfate, glucosamine phosphate, D-Glucosamine-oxime HCI, 6-desoxy-D-glucosamine, N-methyl-D-glucosamine, N-propyl-D-glucosamine, N-octyl-D-glucosamine, N-butyryl-D-glucosamine, N-boc-D-glucosamine, N-hexanoyl-D-glucosamine, N-acetyl-D-glucosaminic acid, N-acetyl-D-glucosamine, N-acetyl galactosamine, N-alloc glucosamine, N-benzoyl-D-glucosamine, N-butanoyl-D-glucosamine, N-propanoyl-D-glucosamine, pentaacetyl-D-glucosamine, N-Valeryl-D-glucosamine, N-octanoyl-D-glucosamine, and combinations thereof, preferably the composition comprises N-acetyl-D-glucosamine.6.The composition according to any of claims 1 to 5, wherein the aminosugar is present in an amount ranging from 0.00001 wt. %to 10 wt. %, preferably from 0.0001 wt. %to 5 wt. %, more preferably from 0.0002 wt. %to 3 wt. %, even more preferably from 0.0003 wt. %to 2 wt. %, relative to the total weight of the composition.7.The composition according to any of claims 1 to 6, wherein the Inonotus obliquus extract is extracted from the whole fungus, one or more parts of the fungus, and combinations thereof, preferably, the composition comprises an extract of the whole fungus.8.The composition according to any of claims 1 to 7, wherein the Inonotus obliquus extract is present in an amount ranging from 0.00001 wt. %to 10 wt. %, preferably from 0.0001 wt. %to 5 wt. %, more preferably from 0.0002 wt. %to 3 wt. %, even more preferably from 0.0003 wt. %to 2 wt. %, relative to the total weight of the composition.9.The composition according to claim 1, comprising, relative to the total weight of the composition:(i) from 0.02 wt. %to 5 wt. %of hydroxypropyl tetrahydropyrantriol;(ii) from 0.0003 wt. %to 2 wt. %of at least one aminosugar selected from N-boc-D-glucosamine, N-hexanoyl-D-glucosamine, N-acetyl-D-glucosamine, N-alloc glucosamine, N-benzoyl-D-glucosamine, N-butanoyl-D-glucosamine, N-propanoyl-D-glucosamine, N-Valeryl-D-glucosamine, N-octanoyl-D-glucosamine, and combinations thereof; and(iii) from 0.0003 wt. %to 2 wt. %of at least one Inonotus obliquus extract.10.The composition according to any of claims 1 to 9, wherein the weight ratio of the Inonotus obliquus extract to the C-glycoside is from 1: 50 to 1: 1, preferably from 1: 40 to 1: 2, more preferably from 1: 35 to 1: 3.11.The composition according to any of claims 1 to 10, wherein the weight ratio of the Inonotus obliquus extract to the aminosugar is from 1: 10 to 10: 1, preferably from 1: 5 to 5: 1, more preferably from 1: 2 to 2: 1.12.The composition according to any of claims 1 to 11, 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 99.99 wt. %, relative to the total weight of the composition.13.A non-therapeutic method for caring for keratin materials, comprising applying the composition according to any of claims 1 to 12 to the keratin materials.14.The method according to claim 13, wherein the keratin material is the skin.
Citation Information
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FR2946254A1