WO2024221373A1 - Composition cosmétique et son utilisation - Google Patents
Composition cosmétique et son utilisation Download PDFInfo
- Publication number
- WO2024221373A1 WO2024221373A1 PCT/CN2023/091432 CN2023091432W WO2024221373A1 WO 2024221373 A1 WO2024221373 A1 WO 2024221373A1 CN 2023091432 W CN2023091432 W CN 2023091432W WO 2024221373 A1 WO2024221373 A1 WO 2024221373A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acetyl
- acid
- neuraminic acid
- glycolyl
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 124
- 239000002537 cosmetic Substances 0.000 title claims abstract description 17
- KBGAYAKRZNYFFG-BOHATCBPSA-N aceneuramic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](NC(=O)C)[C@@H](O)[C@H](O)[C@H](O)CO KBGAYAKRZNYFFG-BOHATCBPSA-N 0.000 claims abstract description 28
- 241001264174 Cordyceps militaris Species 0.000 claims abstract description 27
- 102000011782 Keratins Human genes 0.000 claims abstract description 16
- 108010076876 Keratins Proteins 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 16
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
- 229930182476 C-glycoside Natural products 0.000 claims description 18
- 150000000700 C-glycosides Chemical class 0.000 claims description 15
- 241000194036 Lactococcus Species 0.000 claims description 14
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims description 14
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims description 14
- SUHQNCLNRUAGOO-UHFFFAOYSA-N N-glycoloyl-neuraminic acid Natural products OCC(O)C(O)C(O)C(NC(=O)CO)C(O)CC(=O)C(O)=O SUHQNCLNRUAGOO-UHFFFAOYSA-N 0.000 claims description 12
- FDJKUWYYUZCUJX-UHFFFAOYSA-N N-glycolyl-beta-neuraminic acid Natural products OCC(O)C(O)C1OC(O)(C(O)=O)CC(O)C1NC(=O)CO FDJKUWYYUZCUJX-UHFFFAOYSA-N 0.000 claims description 12
- FDJKUWYYUZCUJX-KVNVFURPSA-N N-glycolylneuraminic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H]1O[C@](O)(C(O)=O)C[C@H](O)[C@H]1NC(=O)CO FDJKUWYYUZCUJX-KVNVFURPSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000002772 monosaccharides Chemical class 0.000 claims description 8
- 150000004676 glycans Chemical class 0.000 claims description 7
- 229920001282 polysaccharide Polymers 0.000 claims description 7
- 239000005017 polysaccharide Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000003712 anti-aging effect Effects 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- UJZYBTQCNFXSTG-MTESWFDDSA-N (4S,5R,6R)-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid Chemical compound CC(=O)OC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(O)(C(O)=O)C[C@H](O)[C@H]1NC(=O)CO UJZYBTQCNFXSTG-MTESWFDDSA-N 0.000 claims description 3
- XGWNWUZLPNFYOU-AKEWWUJNSA-N (4S,5R,6R)-4-acetyloxy-2-hydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid Chemical compound CC(=O)O[C@H]1CC(O)(C(O)=O)O[C@@H]([C@H](O)[C@H](O)CO)[C@@H]1NC(=O)CO XGWNWUZLPNFYOU-AKEWWUJNSA-N 0.000 claims description 3
- YCXFWJURAUFUBE-HGZSSABNSA-N (4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](OC(C)=O)[C@@H](COC(C)=O)OC(C)=O YCXFWJURAUFUBE-HGZSSABNSA-N 0.000 claims description 3
- LVBIMVQYUKOENY-OABCVWDLSA-N (4S,5R,6R)-5-acetamido-4-acetyloxy-2-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1[C@@H](OC(C)=O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO LVBIMVQYUKOENY-OABCVWDLSA-N 0.000 claims description 3
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- DUOKWMWKFGDUDQ-CHNADMEASA-N (4S,5R,6R)-5-acetamido-6-[(1R,2R)-1-acetyloxy-2,3-dihydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](OC(C)=O)[C@H](O)CO DUOKWMWKFGDUDQ-CHNADMEASA-N 0.000 claims description 3
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- PPOPOQUIFLBQOB-CHNADMEASA-N (4S,5R,6R)-5-acetamido-6-[(1S,2R)-2-acetyloxy-1,3-dihydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@@H](CO)OC(C)=O PPOPOQUIFLBQOB-CHNADMEASA-N 0.000 claims description 3
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- UYIAKSLBZCGVPJ-OXWSVYLXSA-N (4S,5R,6R)-6-[(1S,2R)-1,3-diacetyloxy-2-methoxypropyl]-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]oxane-2-carboxylic acid Chemical compound CC(=O)OC[C@@H](OC)[C@@H](OC(C)=O)[C@@H]1OC(O)(C(O)=O)C[C@H](O)[C@H]1NC(=O)CO UYIAKSLBZCGVPJ-OXWSVYLXSA-N 0.000 claims description 3
- OPLHZHKSIOUCED-RIZHGAQMSA-N (4S,5R,6R)-6-[(1S,2R)-1,3-dihydroxy-2-methoxypropyl]-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]oxane-2-carboxylic acid Chemical compound CO[C@H](CO)[C@@H](O)[C@@H]1OC(O)(C(O)=O)C[C@H](O)[C@H]1NC(=O)CO OPLHZHKSIOUCED-RIZHGAQMSA-N 0.000 claims description 3
- FIOUPKIHVYLEII-CIOHLJSHSA-N (4S,5R,6R)-6-[(1S,2R)-2,3-diacetyloxy-1-hydroxypropyl]-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]oxane-2-carboxylic acid Chemical compound CC(=O)OC[C@@H](OC(C)=O)[C@@H](O)[C@@H]1OC(O)(C(O)=O)C[C@H](O)[C@H]1NC(=O)CO FIOUPKIHVYLEII-CIOHLJSHSA-N 0.000 claims description 3
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- 125000003277 amino group Chemical group 0.000 claims description 3
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- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- NCMJSVDTRDLWJE-LUWBGTNYSA-N (1R,2R,3S,7R)-2-acetamido-7-[(1R)-1,2-dihydroxyethyl]-3-hydroxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylic acid Chemical compound O1C2(C(O)=O)C[C@H](O)[C@@H](NC(C)=O)[C@]1([H])[C@@H]([C@H](O)CO)O2 NCMJSVDTRDLWJE-LUWBGTNYSA-N 0.000 claims description 2
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- 235000020944 retinol Nutrition 0.000 description 1
- 239000011607 retinol Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 210000001626 skin fibroblast Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000009492 vitamin B5 Nutrition 0.000 description 1
- 239000011675 vitamin B5 Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- KPTPSLHFVHXOBZ-BIKCPUHGSA-N xylotetraose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)C(O)OC3)O)OC2)O)OC1 KPTPSLHFVHXOBZ-BIKCPUHGSA-N 0.000 description 1
- ABKNGTPZXRUSOI-UHFFFAOYSA-N xylotriose Natural products OCC(OC1OCC(OC2OCC(O)C(O)C2O)C(O)C1O)C(O)C(O)C=O ABKNGTPZXRUSOI-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9728—Fungi, e.g. yeasts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/85—Products or compounds obtained by fermentation, e.g. yoghurt, beer, wine
Definitions
- the present invention relates to a cosmetic composition.
- the present invention also relates to use of the cosmetic composition and a non-therapeutic method for caring for keratin materials.
- 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) .
- ECM extracellular matrix
- 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) .
- 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. The lose of collagen will cause skin wrinkles and lack of firmness.
- 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 products are not sufficiently effective.
- 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.
- compositions for caring for the skin which can effectively resist skin ageing.
- the present invention provides a cosmetic composition comprising:
- composition of the present invention can improve the content of collagen I and inhibit MMP-1 production, and effectively resist skin ageing.
- the present invention provides use of the composition of the present invention for anti-ageing of keratin materials.
- 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.
- keratin materials is intended to cover human skin, mucous membranes such as the lips. Facial skin is most particularly considered according to the present invention.
- acomposition of the present invention comprises:
- the composition of the present invention comprises at least one acetylneuraminic acid.
- the acetylneuraminic acid is selected from N-glycolylneuraminic acid (NGNA) , N-acetylneuraminic acid (NANA) , 5-N-Acetyl-4-O-acetyl-neuraminic acid, 5-N-Acetyl-7-O-acetyl-neuraminic acid, 5-N-Acetyl-8-O-acetyl-neuraminic acid, 5-N-Acetyl-9-O-acetyl-neuraminic acid, 5-N-Acetyl-4, 9-di-O-acetyl-neuraminic acid, 5-N-Acetyl-7, 9-di-O-acetyl-neuraminic acid, 5-N-Acetyl-8, 9-di-O-acetyl-neuraminic acid, 5-N-Acetyl-7, 8, 9-tri-O-acetyl-neuraminic acid, 5-N-Acetyl-7,
- acetylneuraminic acid is selected from N-glycolylneuraminic acid (NGNA) , N-acetylneuraminic acid (NANA) , 5-N-Acetyl-4-O-acetyl-neuraminic acid, 5-N-Acetyl-7-O-acetyl-neuraminic acid, 5-N-Acetyl-8-O-acetyl-neuraminic acid, 5-N-Acetyl-9-O-acetyl-neuraminic acid, 5-N-Acetyl-4, 9-di-O-acetyl-neuraminic acid, 5-N-Acetyl-7, 9-di-O-acetyl-neuraminic acid, 5-N-Acetyl-8, 9-di-O-acetyl-neuraminic acid, 5-N-Acetyl-7, 8, 9-tri-O-acetyl-neuraminic acid, 5-N-Acetyl
- the acetylneuraminic acid is selected from N-glycolylneuraminic acid (NGNA) , N-acetylneuraminic acid (NANA) , N- (O-acetyl) glycolylneuraminic acid, N- (O-Methyl) glycolylneuraminic acid, and combinations thereof.
- NGNA N-glycolylneuraminic acid
- NANA N-acetylneuraminic acid
- N- (O-acetyl) glycolylneuraminic acid N- (O-Methyl) glycolylneuraminic acid, and combinations thereof.
- composition of the present invention comprises N-acetylneuraminic acid (NANA) .
- NANA N-acetylneuraminic acid
- the acetylneuraminic acid is present in the composition of the present invention in an amount ranging from 0.001 wt. %to 1.0 wt. %, preferably from 0.005 wt. %to 0.5 wt. %, more preferably from 0.01 wt. %to 0.3 wt. %, relative to the total weight of the composition.
- the composition of the present invention comprises at least one cordyceps militaris ferment extract.
- the cordyceps militaris ferment extract is an extract of lactococcus ferment based on cordyceps militaris origin.
- Cordyceps militaris is the type species ofAscomycota, Hypocreas, Ergotaceae and Cordyceps.
- the Cordyceps militaris cultivated by living chrysalis is generally called Cordyceps militaris.
- the main active ingredients in Cordyceps militaris are cordycepin, cordycepic acid and cordyceps polysaccharide. Cordycepin, is also known as 3-deoxyadenosine.
- a fermentation extract of cordyceps militaris can be obtained as follows: lactobacillus are fermented and cultivated in a fermentation medium using cordyceps militaris as a nitrogen source.
- cordyceps militaris is the only nitrogen source.
- BIOYOUTH TM- As an example of commercial products of cordyceps militaris ferment extract, mention can be made of that sold under the name of BIOYOUTH TM- by the company BLOOMAGE BIOTECHNOLOGY.
- the cordyceps militaris ferment extract is present in the composition of the present invention in an amount of dry matter ranging from 0.001 wt. %to 1 wt. %, preferably from 0.005 wt. %to 0.5 wt. %, more preferably from 0.01 wt. %to 0.3 wt. %, relative to the total weight of the composition.
- the weight ratio of the at least one acetylneuraminic acid to the at least one cordyceps militaris ferment extract ranges from 1: 10 to 2: 1, preferably from 1: 5 to 1: 1.
- composition of the present invention comprises at least one C-glycoside compound.
- the C-glycoside is selected from compounds of formula (I) :
- R represents a saturated C 1 to C 10 , in particular C 1 to C 4 , alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR” 2 , with R” 2 being a saturated C 1 -C 4 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 selected from the–CO-, -CH (OH) -, -CH (NH 2 ) -, -CH (NHCH 2 CH 2 CH 2 OH) -, -CH (NHPh) -and–CH (CH 3 ) -groups and in particular a–CO-, -CH (OH) -or–CH (NH 2 ) -radical and more particularly a–CH (OH) -radical,
- the S-CH 2 -X bond represents a bond of C-anomeric nature, which can be ⁇ or ⁇ ,
- the C-glycoside of use for the implementation of the invention are in particular those for which R denotes a saturated linear C 1 to C 6 , in particular C 1 to C 4 , preferentially C 1 to C 2 , alkyl radical and more preferably a methyl radical.
- amonosaccharide of the invention can be selected 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.
- apolysaccharide of the invention comprising up to 6 sugar units can be selected from D-maltose, D-lactose, D-cellobiose, D-maltotriose, adisaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid with a hexosamine selected 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 selected from xylobiose, methyl- ⁇ -xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.
- S can represent a monosaccharide selected from D-glucose, D-xylose, L-fucose, D-galactose or D-maltose and in particular D-xylose.
- - R denotes an unsubstituted linear C 1 -C 4 , in particular C 1 -C 2 , 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 selected from-CO-, -CH (OH) -or-CH (NH 2 ) -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.
- neutralization of the acid group (s) can be carried out with an inorganic base, such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH, 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.
- an inorganic base such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH, Mg (OH) 2 or Zn (OH) 2
- 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.
- 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.
- 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 WO 02/051828.
- C- ⁇ -D-xylopyranoside-2-hydroxypropane or C- ⁇ -D-xylopyranoside-2-hydroxypropane and better still C- ⁇ -D-xylopyranoside-2-hydroxypropane can advantageously be used for the preparation of a composition according to the invention.
- the C-glycoside can be C- ⁇ -D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) provided in the form of a solution containing 35%by weight of active material in water and propylene glycol.
- the C-glycoside is present in the composition of the present invention in an amount ranging from 0.01 wt. %to 15 wt. %, preferably from 0.05 wt. %to 10 wt. %, more preferably from 0.1 wt. %to 8 wt. %, relative to the total weight of the composition.
- the ratio of the total weight of at least one acetylneuraminic acid and the at least one cordyceps militaris ferment extract to the weight of the C-glycoside ranges from 1: 3 to 1: 40, preferably from 1: 10 to 1: 35.
- composition of the present invention may comprise an aqueous phase.
- Said aqueous phase comprises water.
- the composition according to the invention comprises water.
- water is present in the composition of the present invention in an amount ranging from 30 wt. %to 98 wt. %, preferably from 40 wt. %to 90 wt. %, more preferably from 50 wt. %to 80 wt. %, relative to the total weight of the composition.
- the composition comprises an organic solvent miscible with water (at room temperature 25°C) 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, so as to provide a hydration effect.
- an organic solvent miscible with water 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, so as to provide a hydration effect.
- the organic solvent miscible with water selected from monoalcohols, glycols and polyols is present in the composition in an amount ranging from 0.5 wt. %to 30 wt. %, preferably from 5 wt. %to 20 wt. %, relative to the total weight of the composition.
- the composition of the present invention comprises water and glycerin.
- composition of the present invention may comprise an oily phase.
- the oily phase contains at least one oil. It may also contain other fatty substances.
- the composition comprises at least one oil.
- oil means a water-immiscible non-aqueous compound that is liquid at room temperature (20°C) and at atmospheric pressure (760 mmHg) .
- the oils may be volatile or non-volatile.
- non-volatile refers to an oil whose vapour pressure at room temperature and atmospheric pressure is non-zero and is less than 10-3 mmHg (0.13 Pa) .
- volatile oil means any oil that is capable of evaporating on contact with the skin in less than one hour, at room temperature and atmospheric pressure.
- the oily phase may comprise hydrocarbon-based oils, silicone oils, or mixtures thereof.
- They may be of animal, plant, mineral or synthetic origin.
- silicon oil means an oil comprising at least one silicon atom, and notably at least one Si-O group.
- hydrocarbon-based oil means an oil mainly containing hydrogen and carbon atoms.
- the oils may optionally comprise oxygen, nitrogen, sulfur and/or phosphorus atoms, for example in the form of hydroxyl or acid radicals.
- the oily phase is present in the composition of the present invention in an amount ranging from 0.1 wt. %to 40 wt. %, preferably from 10 wt. %to 25 wt. %, relative to the total weight of the composition of the present invention.
- composition of the present invention may comprise an additional cosmetic active ingredient in addition to the cosmetic active ingredients as defined previously.
- moisturizing agents examples include moisturizing agents; vitamins such as vitamin A (retinol) , vitamin E (tocopherol) , vitamin C (ascorbic acid) , vitamin B5 (panthenol) , and derivatives of said vitamins (in particular esters) and mixtures thereof; brightening agents; tightening agents; peeling agents; moisturizing and hydration agents (HA) , repairing and soothing agents; other anti-ageing agents; agents acting on the microcirculation; oil-control agents; anti-acne agents; UV filters; agents acting on pigmentations and mixtures thereof.
- moisturizing agents such as vitamin A (retinol) , vitamin E (tocopherol) , vitamin C (ascorbic acid) , vitamin B5 (panthenol) , and derivatives of said vitamins (in particular esters) and mixtures thereof
- brightening agents tightening agents; peeling agents; moisturizing and hydration agents (HA) , repairing and soothing agents
- composition of the present invention may comprise conventional cosmetic adjuvants or additives, for instance fragrances, chelating agents, preservatives, surfactants, thickeners, colorants/pigments, pH regulators, and mixtures thereof.
- fragrances for instance fragrances, chelating agents, preservatives, surfactants, thickeners, colorants/pigments, pH regulators, and mixtures thereof.
- the present invention provides a cosmetic composition comprising, relative to the total weight of the composition:
- acetylneuraminic acid selected from N-glycolylneuraminic acid (NGNA) , N-acetylneuraminic acid (NANA) , N- (O-acetyl) glycolylneuraminic acid, N- (O-Methyl) glycolylneuraminic acid, and combinations thereof; and
- composition of the present invention is in the form of emulsion, cream, lotion, mask, or hydrogel.
- composition of the present invention can be used for caring for keratin materials.
- the present invention provides use of the composition of the present invention for anti-ageing of keratin materials.
- the present invention provides use of the composition of the present invention for boosting collagen production and/or inhibiting MMP-1 production.
- 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.
- the present invention provides a non-therapeutic method for anti-ageing of keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
- the keratin material is the skin.
- compositions of invention formula 1 and comparative formulas 1-A and 1-B were prepared based on the amounts given in Table 2. The amounts are given in%by weight of active ingredient relative to the total weight of the composition.
- composition of invention formula 1 represents composition according to the present invention.
- Composition of comparative formula 1-A does not comprise LACTOCOCCUS FERMENT.
- Composition of comparative formula 1-B does not comprise ACETYLNEURAMINIC ACID.
- compositions listed above were prepared as follows: diluting each raw material in sterilized double distilled H 2 O in room temperature and dissolving them in water with stirring.
- Collagen type I ELISA assay was carried out as follows.
- Normal human fibroblast cells were seeded into 6-well plates with a cell density of 2X10 5 cells/well, under 5%CO 2 , 95%humidity, 37°C in a cell incubator (Thermo 150I) for overnight culture. When the cell density reached confluency of 40 ⁇ 60%, the cell culture medium was changed to fresh medium containing tested raw materials with different concentrations or combinations. The treated cells were put in a cell incubatorwith 5%CO 2 , 95%humidity, 37°C for 24 hours.
- test group had three replicate cells.
- Cell culture supernatants were collected for Collagen type I ELISA assay (Cusabio) .
- the group without any treatment was taken as blank control (BC) group, the group treated with 100 ng/ml TGF- ⁇ 1 (Peprotech) was taken as the positive control (PC) group.
- the other three groups were treated with fresh medium containing compositions of invention formula 1, comparative formulas 1-A and 1-B, respectively.
- Procedure of ELISA assay fully followed the standard protocol illustrated in the test kit.
- composition of invention formula 1 can significantly improve the collagen I content, as compared with compositions of comparative formulas 1-A and 1-B.
- compositions of invention formula 2 and comparative formulas 2-A and 2-B were prepared based on the amounts given in Table 4 following the protocol as described in Example 1. The amounts are given in%by weight of active ingredient relative to the total weight of the composition.
- composition of invention formula 2 represents composition according to the present invention.
- Composition of comparative formula 2-A does not comprise LACTOCOCCUS FERMENT.
- Composition of comparative formula 2-B does not comprise ACETYLNEURAMINIC ACID.
- Collagen type I ELISA assay was carried out according to the protocol as described in Example 1, the relative improvement of the collagen I content for each group was calculated and the results were summarized in Table 5.
- composition of invention formula 2 can significantly improve the collagen I content, as compared with compositions of comparative formulas 2-A and 2-B.
- compositions of invention formula 3 and comparative formulas 3-A and 3-B were prepared based on the amounts given in Table 6 following the protocol as described in Example 1. The amounts are given in%by weight of active ingredient relative to the total weight of the composition.
- composition of invention formula 3 represents composition according to the present invention.
- Composition of comparative formula 3-A does not comprise LACTOCOCCUS FERMENT.
- Composition of comparative formula 3-B does not comprise ACETYLNEURAMINIC ACID.
- Collagen type I ELISA assay was carried out according to the protocol as described in Example 1, the relative improvement of the collagen I content for each group was calculated and the results were summarized in Table 7.
- composition of invention formula 3 can significantly improve the collagen I content, as compared with compositions of comparative formulas 3-A and 3-B.
- compositions of invention formula 4 and comparative formulas 4-A and 4-B were prepared based on the amounts given in Table 8 following the protocol as described in Example 1. The amounts are given in%by weight of active ingredient relative to the total weight of the composition.
- composition of invention formula 4 represents composition according to the present invention.
- Composition of comparative formula 4-A does not comprise ACETYLNEURAMINIC ACID.
- Composition of comparative formula 4-B does not comprise LACTOCOCCUS FERMENT.
- Collagen type I ELISA assay was carried out according to the protocol as described in Example 1, the relative improvement of the collagen I content for each group was calculated and the results were summarized in Table 9.
- composition of invention formula 3 can significantly improve the collagen I content, as compared with compositions of comparative formulas 4-A and 4-B.
- compositions of invention formula 5 and comparative formulas 5-A and 5-B were prepared based on the amounts given in Table 10 following the protocol as described in Example 1. The amounts are given in%by weight of active ingredient relative to the total weight of the composition.
- composition of invention formula 5 represents composition according to the present invention.
- Composition of comparative formula 5-A does not comprise LACTOCOCCUS FERMENT.
- Composition of comparative formula 5-B does not comprise ACETYLNEURAMINICACID.
- MMP-1 ELISA assay was carried out as follows.
- Cell seeding human skin fibroblasts were grown to 80%confluency, digested and suspended, and the cell density was adjusted to 30000 cells/well using complete medium (DMEM with 10%FBS, Gibco, Lot: 2275120) . The cells were inoculated on a 24-well plate and incubated in a cell incubator (5%CO 2 , 95%humidity, 37 °C) for 24 hours.
- Subject exposure The original medium was removed and replaced with DMEM containing 1%FBS or 1%FBS DMEM containing different concentrations of samples, incubated in the incubator for 24 hours.
- the group treated with 0.1uM dexamethasone (DT) was taken as the positive control (PC) group.
- the group not treated with any composition was taken as the non-treatment (NT) group.
- the other three groups were treated with fresh medium containing compositions of invention formula 5, comparative formulas 5-A and 5-B, respectively.
- UVA modeling Before UVA irradiation, discarded the medium, added 200 ⁇ L/well of PBS. For the plates needed UVA irradiation, put them under ultraviolet lamp, adjusted the UVA irradiation intensity to 2.5mW/cm 2 , irradiated with 6J/cm2 UVA ( ⁇ 40min) . For no UVA control (blank control) plate, put the plate on area without UVA irradiation. After irradiation, PBS was removed and replaced with DMEM containing 1%FBS or 1%FBS DMEM containing different concentrations of raw materials, plates were put in the incubator for 48 hours. After incubation, the supernatant was collected into sterile Eppendorf tubes, centrifuged at 12,000 RPM for 5 min at low temperature, and stored at -80°C.
- composition of invention formula 5 can significantly inhibit the MMP-1 content, as compared with compositions of comparative formulas 5-A and 5-B.
- composition according to the present invention can improve the content of collagen I and inhibit MMP-1 production, therefore can effectively resist skin ageing.
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Abstract
L'invention concerne une composition cosmétique comprenant : (i) au moins un acide acétylneuraminique; et (ii) au moins un extrait de ferment de Cordyceps militaris. L'invention concerne également l'utilisation de la composition cosmétique et un procédé non thérapeutique pour le soin des matières kératiniques.
Priority Applications (3)
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PCT/CN2023/091432 WO2024221373A1 (fr) | 2023-04-28 | 2023-04-28 | Composition cosmétique et son utilisation |
CN202380039711.7A CN119255785A (zh) | 2023-04-28 | 2023-04-28 | 化妆品组合物及其用途 |
FR2306315A FR3148146B1 (fr) | 2023-04-28 | 2023-06-20 | Composition cosmétique et son utilisation |
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PCT/CN2023/091432 WO2024221373A1 (fr) | 2023-04-28 | 2023-04-28 | Composition cosmétique et son utilisation |
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PCT/CN2023/091432 WO2024221373A1 (fr) | 2023-04-28 | 2023-04-28 | Composition cosmétique et son utilisation |
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CN (1) | CN119255785A (fr) |
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Citations (6)
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WO2016197144A1 (fr) * | 2015-06-05 | 2016-12-08 | Nse Products, Inc. | Formulation topique de soin de la peau contenant du cordyceps |
CN107638316A (zh) * | 2017-09-08 | 2018-01-30 | 徐跃 | 虫草属真菌细胞代谢产物在制备护肤品中的用途及护肤品 |
CN111358702A (zh) * | 2020-05-21 | 2020-07-03 | 南通大学 | 一种长效抗皱皮肤营养液及其制备方法 |
CN111808901A (zh) * | 2020-07-07 | 2020-10-23 | 华熙生物科技股份有限公司 | 一种蛹虫草发酵提取液的制备方法及所得产品和应用 |
CN113876611A (zh) * | 2021-11-01 | 2022-01-04 | 武汉中科光谷绿色生物技术有限公司 | 唾液酸在制备促进胶原蛋白生成的制剂中的应用 |
CN115554309A (zh) * | 2022-11-04 | 2023-01-03 | 南京工业大学 | 一种药物组合物及其在制备防治精神性疾病和/或亚健康精神状态产品中的应用 |
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Publication number | Priority date | Publication date | Assignee | Title |
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FR2818547B1 (fr) | 2000-12-22 | 2006-11-17 | Oreal | Nouveaux derives c-glycosides et utilisation |
CN104083291A (zh) * | 2014-06-16 | 2014-10-08 | 武汉中科光谷绿色生物技术有限公司 | N-乙酰神经氨酸单体或其水合物在化妆品中的应用 |
CN114450026A (zh) * | 2019-07-26 | 2022-05-06 | 生命科学股份有限公司 | 用于治疗银屑病用途的唾液酸 |
CN113512108B (zh) * | 2021-03-23 | 2022-03-25 | 广州天启生物科技有限公司 | 海洋鱼皮胶原低聚肽及其制备方法和应用 |
-
2023
- 2023-04-28 WO PCT/CN2023/091432 patent/WO2024221373A1/fr unknown
- 2023-04-28 CN CN202380039711.7A patent/CN119255785A/zh active Pending
- 2023-06-20 FR FR2306315A patent/FR3148146B1/fr active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016197144A1 (fr) * | 2015-06-05 | 2016-12-08 | Nse Products, Inc. | Formulation topique de soin de la peau contenant du cordyceps |
CN107638316A (zh) * | 2017-09-08 | 2018-01-30 | 徐跃 | 虫草属真菌细胞代谢产物在制备护肤品中的用途及护肤品 |
CN111358702A (zh) * | 2020-05-21 | 2020-07-03 | 南通大学 | 一种长效抗皱皮肤营养液及其制备方法 |
CN111808901A (zh) * | 2020-07-07 | 2020-10-23 | 华熙生物科技股份有限公司 | 一种蛹虫草发酵提取液的制备方法及所得产品和应用 |
CN113876611A (zh) * | 2021-11-01 | 2022-01-04 | 武汉中科光谷绿色生物技术有限公司 | 唾液酸在制备促进胶原蛋白生成的制剂中的应用 |
CN115554309A (zh) * | 2022-11-04 | 2023-01-03 | 南京工业大学 | 一种药物组合物及其在制备防治精神性疾病和/或亚健康精神状态产品中的应用 |
Also Published As
Publication number | Publication date |
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CN119255785A (zh) | 2025-01-03 |
FR3148146B1 (fr) | 2025-05-02 |
FR3148146A1 (fr) | 2024-11-01 |
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