CN117224418B - Anti-aging composition and product application thereof - Google Patents
Anti-aging composition and product application thereof Download PDFInfo
- Publication number
- CN117224418B CN117224418B CN202311502272.7A CN202311502272A CN117224418B CN 117224418 B CN117224418 B CN 117224418B CN 202311502272 A CN202311502272 A CN 202311502272A CN 117224418 B CN117224418 B CN 117224418B
- Authority
- CN
- China
- Prior art keywords
- galactose
- aging composition
- derivative
- water
- ratio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 85
- 230000003712 anti-aging effect Effects 0.000 title claims abstract description 67
- 238000010521 absorption reaction Methods 0.000 claims abstract description 32
- 239000003623 enhancer Substances 0.000 claims abstract description 21
- 150000008195 galaktosides Chemical class 0.000 claims abstract description 14
- 229930182470 glycoside Natural products 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 229940124532 absorption promoter Drugs 0.000 claims abstract description 7
- -1 galactose glycoside Chemical class 0.000 claims abstract description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002338 glycosides Chemical class 0.000 claims abstract description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004185 ester group Chemical group 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 claims description 64
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 52
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 229930003427 Vitamin E Natural products 0.000 claims description 26
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 26
- 235000019165 vitamin E Nutrition 0.000 claims description 26
- 229940046009 vitamin E Drugs 0.000 claims description 26
- 239000011709 vitamin E Substances 0.000 claims description 26
- QKVWBAMZPUHCMO-UHFFFAOYSA-N 2-pyrazin-2-ylethanethiol Chemical compound SCCC1=CN=CC=N1 QKVWBAMZPUHCMO-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- QRYRORQUOLYVBU-VBKZILBWSA-N Carnosic acid Natural products CC([C@@H]1CC2)(C)CCC[C@]1(C(O)=O)C1=C2C=C(C(C)C)C(O)=C1O QRYRORQUOLYVBU-VBKZILBWSA-N 0.000 claims description 14
- 108010087806 Carnosine Proteins 0.000 claims description 14
- CQOVPNPJLQNMDC-UHFFFAOYSA-N N-beta-alanyl-L-histidine Natural products NCCC(=O)NC(C(O)=O)CC1=CN=CN1 CQOVPNPJLQNMDC-UHFFFAOYSA-N 0.000 claims description 14
- CQOVPNPJLQNMDC-ZETCQYMHSA-N carnosine Chemical compound [NH3+]CCC(=O)N[C@H](C([O-])=O)CC1=CNC=N1 CQOVPNPJLQNMDC-ZETCQYMHSA-N 0.000 claims description 14
- 229940044199 carnosine Drugs 0.000 claims description 14
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- 239000003998 snake venom Substances 0.000 claims description 14
- 101000761020 Dinoponera quadriceps Poneritoxin Proteins 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 12
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- LODWEXDBRZBADB-XEVVZDEMSA-N (2s)-6-amino-2-[[(2s)-2-[[(2s)-6-amino-2-(hexadecanoylamino)hexanoyl]amino]-3-methylbutanoyl]amino]hexanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(O)=O LODWEXDBRZBADB-XEVVZDEMSA-N 0.000 claims description 9
- AJLNZWYOJAWBCR-OOPVGHQCSA-N (4s)-4-acetamido-5-[[(2s)-1-[[(2s)-1-[[(2s)-5-amino-1-[[(2s)-1-[[(2s)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-car Chemical compound OC(=O)CC[C@H](NC(C)=O)C(=C)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCN=C(N)N)C(N)=O AJLNZWYOJAWBCR-OOPVGHQCSA-N 0.000 claims description 9
- 229940095094 acetyl hexapeptide-8 Drugs 0.000 claims description 9
- 108010006338 acetyl-glutamyl-glutamyl-methionyl-glutaminyl-arginyl-argininamide Proteins 0.000 claims description 9
- 229940094912 palmitoyl tripeptide-5 Drugs 0.000 claims description 9
- WSGCRSMLXFHGRM-DEVHWETNSA-N (2s)-2-[[(2s)-6-amino-2-[[(2s,3r)-2-[[(2s,3r)-2-[[(2s)-6-amino-2-(hexadecanoylamino)hexanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(O)=O WSGCRSMLXFHGRM-DEVHWETNSA-N 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims description 4
- GZCGUPFRVQAUEE-KCDKBNATSA-N aldehydo-D-galactose Chemical class OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 48
- 210000001626 skin fibroblast Anatomy 0.000 abstract description 17
- 230000028327 secretion Effects 0.000 abstract description 12
- 230000037303 wrinkles Effects 0.000 abstract description 12
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 11
- 102000008186 Collagen Human genes 0.000 abstract description 10
- 108010035532 Collagen Proteins 0.000 abstract description 10
- 229920001436 collagen Polymers 0.000 abstract description 10
- 230000035755 proliferation Effects 0.000 abstract description 9
- 229930182830 galactose Natural products 0.000 abstract description 8
- 229920001184 polypeptide Polymers 0.000 abstract description 8
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 8
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical class OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 56
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 34
- 150000002256 galaktoses Chemical class 0.000 description 31
- 238000012360 testing method Methods 0.000 description 22
- 210000003491 skin Anatomy 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 17
- 229940074360 caffeic acid Drugs 0.000 description 17
- 235000004883 caffeic acid Nutrition 0.000 description 17
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 17
- 229940015975 1,2-hexanediol Drugs 0.000 description 16
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 239000003755 preservative agent Substances 0.000 description 14
- 230000002335 preservative effect Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 206010040954 Skin wrinkling Diseases 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 102000001187 Collagen Type III Human genes 0.000 description 9
- 108010069502 Collagen Type III Proteins 0.000 description 9
- 230000001737 promoting effect Effects 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 230000012010 growth Effects 0.000 description 7
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 7
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 7
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 7
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 102000000503 Collagen Type II Human genes 0.000 description 5
- 108010041390 Collagen Type II Proteins 0.000 description 5
- 239000013011 aqueous formulation Substances 0.000 description 5
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000007385 chemical modification Methods 0.000 description 4
- 238000012258 culturing Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007405 data analysis Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000002858 neurotransmitter agent Substances 0.000 description 3
- 230000001603 reducing effect Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 230000037394 skin elasticity Effects 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- RJZNPROJTJSYLC-LLINQDLYSA-N (4s)-4-acetamido-5-[[(2s)-1-[[(2s)-1-[[(2s)-5-amino-1-[[(2s)-1-[[(2s)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-car Chemical compound OC(=O)CC[C@H](NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O RJZNPROJTJSYLC-LLINQDLYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 102000012422 Collagen Type I Human genes 0.000 description 2
- 108010022452 Collagen Type I Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 2
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000003187 abdominal effect Effects 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- JZNHNILSWLPPKO-UHFFFAOYSA-N n'-[(4-methoxyphenyl)methyl]-n,n-dimethyl-n'-pyridin-2-ylethane-1,2-diamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JZNHNILSWLPPKO-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- ITIMHIATVYROGF-XWUOBKMESA-N (3S)-3-[[(2S)-2-acetamido-6-aminohexanoyl]amino]-4-[[(2S)-1-[[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-oxobutanoic acid Chemical compound CC(C)[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCCN)NC(C)=O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(O)=O ITIMHIATVYROGF-XWUOBKMESA-N 0.000 description 1
- 102000016942 Elastin Human genes 0.000 description 1
- 108010014258 Elastin Proteins 0.000 description 1
- 108010049140 Endorphins Proteins 0.000 description 1
- 102000009025 Endorphins Human genes 0.000 description 1
- 108010092674 Enkephalins Proteins 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 102000016359 Fibronectins Human genes 0.000 description 1
- 108010067306 Fibronectins Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical class C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 108010050808 Procollagen Proteins 0.000 description 1
- 206010040925 Skin striae Diseases 0.000 description 1
- 102000004183 Synaptosomal-Associated Protein 25 Human genes 0.000 description 1
- 108010057722 Synaptosomal-Associated Protein 25 Proteins 0.000 description 1
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 1
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 1
- 102000009618 Transforming Growth Factors Human genes 0.000 description 1
- 108010009583 Transforming Growth Factors Proteins 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- 229940014843 acetyl dipeptide-1 cetyl ester Drugs 0.000 description 1
- 108010074988 acetyltyrosyl-arginine cetyl ester Proteins 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000011382 collagen catabolic process Effects 0.000 description 1
- 230000037319 collagen production Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 210000004177 elastic tissue Anatomy 0.000 description 1
- 229920002549 elastin Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- JFHZXDZUXGBFAQ-KYJUHHDHSA-N hexadecyl (2s)-2-[[(2s)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](NC(C)=O)CC1=CC=C(O)C=C1 JFHZXDZUXGBFAQ-KYJUHHDHSA-N 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000000258 photobiological effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000033458 reproduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 230000037393 skin firmness Effects 0.000 description 1
- VSIVTUIKYVGDCX-UHFFFAOYSA-M sodium;4-[2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)tetrazol-2-ium-5-yl]benzene-1,3-disulfonate Chemical compound [Na+].COC1=CC([N+]([O-])=O)=CC=C1[N+]1=NC(C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)=NN1C1=CC=C([N+]([O-])=O)C=C1 VSIVTUIKYVGDCX-UHFFFAOYSA-M 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses an anti-aging composition and application of a product thereof, and relates to the technical field of polypeptide cosmetics. The anti-aging composition comprises a transdermal absorption enhancer; the percutaneous absorption promoter comprises glycoside derivatives; the glycoside derivative comprises a galactose glycoside derivative, wherein the structure of the galactose glycoside derivative comprises alkyl, ester group and pyrazine; the structure of the galactoside derivative also contains sulfur. The anti-aging composition provided by the invention has an extremely remarkable effect of removing wrinkles, remarkably promotes proliferation of human skin fibroblasts, promotes secretion of I, III type collagen, and has remarkable difference compared with the independent use of various functional components.
Description
Technical Field
The invention belongs to the technical field of polypeptide cosmetics, and particularly relates to an anti-aging composition and a product application thereof.
Background
The problem that everyone faces is that aging comes from two aspects, endogenous and exogenous. Endogenous, i.e., human metabolism in the human body with age, can lead to collagen degradation and loss, which is irreversible; exogenous substances, namely substances polluted in life are more and more, oxidized substances are more and more, and generated free radicals can break links of collagen so as to break and lose elasticity.
Polypeptides have a wide variety of biological roles, the most prominent of which is a signaling molecule in a variety of physiological processes including defense, immunity, stress, growth, homeostasis and reproduction. These aspects have been used in the dermatological and cosmetic fields to promote extracellular matrix synthesis, avoid pigmentation, treat innate immunity and inflammation. However, polypeptide actives are sought after by the market due to their remarkable and specific efficacy, without side effects, but also due to their specificity, achieving efficacy against practical complex problems is not as expected.
Although the existing polypeptide composition for resisting aging on the market focuses on exogenous and exogenous aging, the active exogenous and exogenous targets are relatively single, and no clear mechanism and data support exists for the combined synergy. The multiple polypeptide compositions of the invention can achieve the optimal anti-aging effect on the endogenous and exogenous skin by the accurate combination of multiple targets, and meet the demands of consumers.
Disclosure of Invention
The invention aims to provide an anti-aging composition and a product application thereof, wherein the anti-aging composition has an extremely remarkable effect of removing wrinkles, remarkably promotes proliferation of human skin fibroblasts, promotes secretion of I, III type collagen, and has remarkable difference compared with single use of various functional components.
The technical scheme adopted by the invention for achieving the purpose is as follows:
a compound for transdermal absorption comprising a glycoside derivative; the glycoside derivative comprises a galactose glycoside derivative, wherein the structure of the galactose glycoside derivative comprises alkyl, ester group and pyrazine;
the structure of the galactoside derivative also contains sulfur. The invention adopts pyrazinyl ethanethiol to chemically modify D-galactose to prepare galactose derivatives, and the galactose derivatives are used by being compounded with water-soluble vitamin E, so that the galactose derivatives have more excellent transdermal absorption promoting capability; the anti-aging composition is used in the preparation process of the anti-aging composition, can effectively improve the action effect of the composition, obviously enhance the action of the composition on promoting the growth of human skin fibroblasts and promote the secretion of type I and type III collagen; further enhancing the effect of the composition on the skin, obviously improving the effect of lightening lines and elasticity, and further improving the compactness and fineness of the skin. The reason for this may be that galactose derivatives are compounded with water-soluble vitamin E, natural chemical groups in the structure of the galactose derivatives can better enter the dermis layer, and chemically modified parts can better open pores, so that substances can be promoted to be absorbed by a human body through the epidermis layer, and the action effect of the composition is enhanced.
Specifically, the galactoside derivative comprises acetic anhydride and pyrazinyl ethanethiol chemically modified D-galactose products.
The preparation method of the galactose derivative comprises the following steps:
mixing D-galactose, acetic anhydride, glacial acetic acid and perchloric acid, and adding acetyl bromide and methanol for reaction to obtain an intermediate O;
mixing pyrazinyl ethanethiol, potassium carbonate, 1, 4-dioxane and water, and adding a1, 4-dioxane solution of an intermediate O to react to obtain a galactoside derivative.
Further specifically, the preparation method of the galactoside derivative comprises the following steps:
mixing D-galactose, acetic anhydride, glacial acetic acid and perchloric acid, stirring for 0.5-1.5 h at normal temperature, then adding acetyl bromide and methanol, stirring for 1-3 h, pouring into ice water, extracting with dichloromethane, washing an organic phase with saturated sodium bicarbonate solution and saturated sodium chloride solution in sequence, drying with anhydrous sodium sulfate, and concentrating to obtain an intermediate O;
mixing pyrazinyl ethanethiol, potassium carbonate, 1, 4-dioxane and water, stirring at normal temperature for 0.5-1.5 h, then adding a1, 4-dioxane solution of an intermediate O, heating to 50-60 ℃ for reaction, monitoring until the reaction is finished by adopting thin layer chromatography, concentrating, extracting by adopting ethyl acetate, drying by adopting anhydrous magnesium sulfate, concentrating, and recrystallizing by adopting a methanol/dichloromethane mixed solution to obtain the galactoside derivative.
Specifically, the molar ratio of D-galactose to acetic anhydride is 1:5-7; the solid-to-liquid ratio of D-galactose to glacial acetic acid was 1g: 8-12 mL; the solid-liquid ratio of D-galactose and perchloric acid is 75-85 g:1mL; the mol ratio of acetyl bromide to D-galactose is 2.5-3:1; the volume ratio of the methanol to the acetyl bromide is 0.6-0.7:1.
Specifically, the molar ratio of pyrazinyl ethanethiol to potassium carbonate is 1:1.3-1.8; the solid-to-liquid ratio of pyrazinyl ethanethiol to 1, 4-dioxane is 0.08-0.1 g:1mL; the volume ratio of water to 1, 4-dioxane is 0.2-0.4:1; the mol ratio of the intermediate O to pyrazinyl ethanethiol is 1.3-1.8:1; the concentration of the 1, 4-dioxane solution of the intermediate O is 1-2 mmol/mL.
A percutaneous absorption enhancer comprising the above compound for percutaneous absorption.
In particular, the transdermal absorption enhancer further comprises water-soluble vitamin E.
Specifically, the mass ratio of the water-soluble vitamin E to the galactoside derivative is 1:5-20.
An anti-aging composition comprises the above percutaneous absorption enhancer.
Specifically, the anti-aging composition comprises any 3-5 of acetyl hexapeptide-8, snake venom peptide, palmitoyl pentapeptide-4, palmitoyl tripeptide-5 and carnosine. The anti-aging composition provided by the invention has an extremely remarkable effect of removing wrinkles, remarkably promotes proliferation of human skin fibroblasts, promotes secretion of I, III type collagen, has remarkable difference compared with the independent use of various functional components, and achieves unexpected technical effects.
Wherein, acetyl hexapeptide-8, neurotransmitter inhibitory polypeptide mimics the N-terminal structure of neurotransmitter SNAP-25 protein, thereby reducing the release of acetylcholine (Ach). A snake venom peptide, a neurotransmitter-inhibiting polypeptide that mimics the activity of the snake venom Waglein I, binds to the epsilon subunit of nmAChR to block acetylcholine binding to receptors and to block neuronal excitation transmission. Carnosine blocks free radical reactions and glycosylation reactions, prevents the production of oxidative stress products and glycosylated end (AGE) products, promotes collagen production, and eliminates glycosylated dark yellow proteins. Palmitoyl tripeptide-5, activating transforming growth factor TGF-beta, inhibiting the activity of MMP (matrix metalloproteinase); palmitoyl pentapeptide-4, a hydrolysis product of the procollagen alpha 1 chain-MATRIKINES (messenger peptide) is a precisely mimetic active peptide. Can promote the generation of I and III type collagen and fibronectin. The acetyl tetrapeptide-2 has a certain promotion effect on the collagen COL17A1 formed by DEJ semi-bridged granules, can effectively promote the collagen level and elastic fiber, promote the combination of cells and ECM, and resist adverse effects of skin firmness and adhesion loss. Acetyl dipeptide-1 cetyl ester increases the natural synthesis of endorphins and enkephalins, promptly relieves the red-hot stinging of the skin, is anti-inflammatory and pleasant, and is effective in stimulating the regeneration of elastin.
Specifically, the anti-aging composition is in a dosage form comprising an aqueous solution.
Specifically, the anti-aging composition also comprises an anti-corrosion system, wherein the mass concentration is 0.8-1.2%; the anti-corrosion system comprises p-hydroxyacetophenone and 1,2 hexanediol, wherein the mass ratio of the p-hydroxyacetophenone to the 1,2 hexanediol is 1:0.8-1.2.
Specifically, the mass concentration of the acetyl hexapeptide-8, the snake venom peptide, the palmitoyl pentapeptide-4, the palmitoyl tripeptide-5 or the carnosine in the anti-aging composition is 0.01-0.1%.
Specifically, the mass concentration of the transdermal absorption accelerator in the anti-aging composition is 1.5-4%.
Preferably, the anti-aging composition comprises acetyl hexapeptide-8, a snake venom peptide, palmitoyl pentapeptide-4, and carnosine.
Preferably, the anti-aging composition comprises acetyl hexapeptide-8, a snake venom peptide, palmitoyl tripeptide-5, and carnosine.
Preferably, the anti-aging composition comprises acetyl hexapeptide-8, a snake venom peptide, palmitoyl pentapeptide-4, palmitoyl tripeptide-5, and carnosine.
Further preferably, caffeic acid derivatives are also added into the anti-aging composition, and the mass concentration is 0.05-0.2%; the caffeic acid derivative comprises a product of chemically modified caffeic acid of pyridoxine hydrochloride. The invention adopts the chemical modification of caffeic acid by the pioglitamine hydrochloride to obtain caffeic acid derivatives, and the caffeic acid derivatives show excellent bioactivity. The anti-aging composition can be applied to an anti-aging composition, further enhance the wrinkle removing and wrinkle reducing effects of the composition, remarkably promote proliferation of human skin fibroblasts and promote secretion of I, III type collagen.
Specifically, the preparation method of the caffeic acid derivative comprises the following steps: and mixing caffeic acid with pyridoxine hydrochloride, and carrying out amidation reaction under the condition of a catalytic system to obtain the caffeic acid derivative.
Further specifically, the preparation method of the caffeic acid derivative comprises the following steps:
mixing caffeic acid, triethylamine and tetrahydrofuran, adding pyridoxine hydrochloride at 0-4 ℃, adding DMAP, adding DCC after the reaction liquid is clarified, reacting for 24-26 hours at normal temperature, concentrating under reduced pressure, adding ethyl acetate for extraction, shaking uniformly, placing in a refrigerator overnight, concentrating under reduced pressure, extracting 2-4 times by using ethyl acetate, washing an organic phase by adopting 4-6% sodium bicarbonate concentration and 0.8-1.2 mmol/L hydrochloric acid solution, drying by using anhydrous sodium sulfate, concentrating under reduced pressure, and purifying by column chromatography to obtain caffeic acid derivatives.
Specifically, the solid-to-liquid ratio of caffeic acid to tetrahydrofuran is 0.05-0.08 g:1mL; the molar ratio of the pyrilamine hydrochloride to the caffeic acid is 1-1.5:1; the mol ratio of the triethylamine to the caffeic acid is 1.1-1.3:1; the molar ratio of DMAP to caffeic acid is 0.1-0.2:1; the molar ratio of DCC to caffeic acid is 1.2-1.3:1.
The invention also discloses application of the compound for transdermal absorption in preparing cosmetics or skin care products or medicaments.
The invention also discloses application of the anti-aging composition in preparing cosmetics or skin care products or medicaments.
The invention also discloses application of the caffeic acid derivative in preparing anti-aging cosmetics or skin care products or medicaments.
The invention also discloses application of the galactose derivative in preparing a transdermal absorption promoter.
The invention also discloses application of the galactose derivative in preparing cosmetics or skin care products or medicaments.
Compared with the prior art, the invention has the following beneficial effects:
the composition provided by the invention is used for obtaining one or more peptide skin anti-aging compositions by screening combination collocations and single components in different proportions, and combining researches aiming at application characteristics of respective raw materials, for example, the unprecedented effects of single substances are invented through a composition form, so that innovative application of new effects of combining new targets is obtained. The invention adopts pyrazinyl ethanethiol to chemically modify D-galactose to prepare galactose derivatives, and the galactose derivatives are used by being compounded with water-soluble vitamin E, so that better transdermal absorption promoting capability is shown; the anti-aging composition is used in the preparation process of the anti-aging composition, can effectively improve the action effect of the composition, obviously enhance the action of the composition on promoting the growth of human skin fibroblasts and promote the secretion of type I and type III collagen; further enhances the effect of the composition on the skin, obviously improves the effect of improving the wrinkle and elasticity, and obviously improves the compactness and fineness of the skin. Meanwhile, the caffeic acid derivative is obtained by adopting the chemical modification of the pisiform hydrochloride, and is applied to an anti-aging composition, so that the wrinkle removing and wrinkle reducing effects of the composition can be further enhanced, the proliferation of human skin fibroblasts is obviously promoted, and the secretion of I, III type collagen is promoted.
Therefore, the invention provides an anti-aging composition and the application of the product thereof, wherein the anti-aging composition has very remarkable effect of removing wrinkles, remarkably promotes proliferation of human skin fibroblasts, promotes secretion of I, III type collagen, and has remarkable difference compared with the independent use of various functional components.
Drawings
FIG. 1 is an infrared test result of galactose derivatives in the examples of the present invention;
FIG. 2 shows the results of an infrared test of caffeic acid derivatives in an example of the invention.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the following describes in detail various embodiments of the present invention with reference to the embodiments. However, those of ordinary skill in the art will understand that in various embodiments of the present invention, numerous technical details have been set forth in order to provide a better understanding of the present application. However, the technical solutions claimed in the present application can be implemented without these technical details and with various changes and modifications based on the following embodiments.
Example 1:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, acetyl hexapeptide-8,0.05% in a mass concentration of snake venom peptide in a mass concentration of 0.05%, palmitoyl pentapeptide-4,0.05% in a mass concentration of palmitoyl tripeptide-5 in a mass concentration of 0.05% and carnosine in a mass concentration of 0.05%.
Example 2:
an anti-aging composition in the form of an aqueous formulation, which differs from example 1 in that: the raw material components comprise a preservative system with the mass concentration of 1% (comprising p-hydroxyacetophenone and 1, 2-hexanediol, the mass ratio of the p-hydroxyacetophenone to the 1:1), a transdermal absorption enhancer with the mass concentration of 2.5% (comprising water-soluble vitamin E and D-galactose, the mass ratio of the water-soluble vitamin E to the D-galactose being 1:12), acetyl hexapeptide with the mass concentration of 0.05-8,0.05% snake venom peptide with the mass concentration, palmitoyl pentapeptide with the mass concentration of 0.05-4,0.05% carnosine.
Example 3:
an anti-aging composition in the form of an aqueous formulation, which differs from example 1 in that: the raw material components comprise a preservative system (comprising p-hydroxyacetophenone and 1, 2-hexanediol in a mass ratio of 1:1) with a mass concentration of 1%, a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) with a mass concentration of 2.5%, acetyl hexapeptide with a mass concentration of 0.05-8,0.05% of snake venom peptide and palmitoyl tripeptide with a mass concentration of 0.05-5,0.05% of carnosine.
Example 4:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and galactose derivatives in a mass ratio of 1:12) in a mass concentration of 2.5%, acetyl hexapeptide-8,0.05% of snake venom peptide in a mass concentration of 0.05%, palmitoyl pentapeptide-4,0.05% of palmitoyl tripeptide-5,0.05% of carnosine in a mass concentration of 0.05%.
Preparation of galactose derivatives:
mixing D-galactose, acetic anhydride, glacial acetic acid and perchloric acid, stirring for 1h at normal temperature, then adding acetyl bromide and methanol, stirring for 2h, then pouring into ice water, extracting with dichloromethane, washing an organic phase with saturated sodium bicarbonate solution and saturated sodium chloride solution in sequence, drying with anhydrous sodium sulfate, and concentrating to obtain an intermediate O; in the preparation process, the molar ratio of D-galactose to acetic anhydride is 1:6.2; the solid-to-liquid ratio of D-galactose to glacial acetic acid was 1g:10mL; the solid-to-liquid ratio of D-galactose to perchloric acid was 81g:1mL; the molar ratio of acetyl bromide to D-galactose is 2.8:1; the volume ratio of the methanol to the acetyl bromide is 0.66:1;
mixing pyrazinyl ethanethiol, potassium carbonate, 1, 4-dioxane and water, stirring for 1h at normal temperature, then adding a1, 4-dioxane solution of an intermediate O, heating to 50 ℃ for reaction, monitoring until the reaction is finished by adopting thin layer chromatography, concentrating, extracting by adopting ethyl acetate, drying by using anhydrous magnesium sulfate, concentrating, and recrystallizing by using a methanol/dichloromethane mixed solution to obtain a galactose derivative; in the preparation process, the molar ratio of pyrazinyl ethanethiol to potassium carbonate is 1:1.5; the solid-to-liquid ratio of pyrazinyl ethanethiol to 1, 4-dioxane was 0.09g:1mL; the molar ratio of the intermediate O to the pyrazinyl ethanethiol is 1.5:1; the concentration of the 1, 4-dioxane solution of intermediate O was 1.6mmol/mL.
Example 5:
an anti-aging composition in the form of an aqueous formulation, which differs from example 4 in that: the raw material component also comprises caffeic acid derivative with the mass concentration of 0.1 percent.
Preparation of caffeic acid derivatives:
mixing caffeic acid, triethylamine and tetrahydrofuran, adding pyridoxine hydrochloride at 0 ℃, adding DMAP, adding DCC after the reaction liquid is clarified, reacting for 24 hours at normal temperature, concentrating under reduced pressure, adding ethyl acetate for extraction, shaking uniformly, placing in a refrigerator overnight, concentrating under reduced pressure, extracting with ethyl acetate for 3 times, washing the organic phase sequentially with 5% sodium bicarbonate concentration and 1mmol/L hydrochloric acid solution, drying with anhydrous sodium sulfate, concentrating under reduced pressure, and purifying by column chromatography to obtain caffeic acid derivatives; in the specific preparation process, the solid-to-liquid ratio of the caffeic acid to the tetrahydrofuran is 0.065g:1mL; the molar ratio of the pyrilamine hydrochloride to the caffeic acid is 1.3:1; the molar ratio of triethylamine to caffeic acid is 1.2:1; the molar ratio of DMAP to caffeic acid is 0.15:1; the molar ratio of DCC to caffeic acid was 1.25:1.
Example 6:
an anti-aging composition in the form of an aqueous formulation, which differs from example 1 in that: the raw material components also comprise caffeic acid derivatives with mass concentration of 0.05-0.2%.
The caffeic acid derivative was prepared in the same manner as in example 5.
Example 7:
an anti-aging composition in the form of an aqueous formulation, which differs from example 1 in that: the galactose derivatives in the raw material components were prepared in this example.
The galactose derivatives are prepared differently from example 4 in that: an equimolar amount of 2,2' - (1, 2-ethanediylbisoxo) diethyl mercaptan was used in place of pyrazinyl ethanethiol.
Comparative example 1:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1) with a mass concentration of 1%, a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) with a mass concentration of 2.5%, and acetyl hexapeptide-8 with a mass concentration of 0.35%.
Comparative example 2:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and a snake venom peptide in a mass concentration of 0.35%.
Comparative example 3:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1) with a mass concentration of 1%, a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) with a mass concentration of 2.5%, and palmitoyl pentapeptide-4 with a mass concentration of 0.35%.
Comparative example 4:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and palmitoyl tripeptide-5 in a mass concentration of 0.35%.
Comparative example 5:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and carnosine in a mass concentration of 0.35%.
Comparative example 6:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and acetyl hexapeptide-8 in a mass concentration of 0.3%.
Comparative example 7:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and a snake venom peptide in a mass concentration of 0.3%.
Comparative example 8:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and palmitoyl pentapeptide-4 in a mass concentration of 0.3%.
Comparative example 9:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and palmitoyl tripeptide-5 in a mass concentration of 0.3%.
Comparative example 10:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and carnosine in a mass concentration of 0.3%.
Test example 1:
infrared sign
The testing is carried out by adopting a Fourier infrared spectrometer, and the testing range is 500-4000 cm -1 。
The galactose derivatives prepared in example 4 were subjected to the above-described test, and the results are shown in fig. 1. From the analysis of the figure, 1758cm of infrared spectrum -1 Characteristic absorption peak of acetyl C=O on sugar ring appears nearby and is 1600-1400 cm -1 The characteristic absorption peaks of the pyrazine ring exist within the range, and the above results indicate that galactose derivatives in example 4 were successfully prepared.
The caffeic acid derivative prepared in example 5 was subjected to the above test, and the results are shown in fig. 2. From the figureAs can be seen from the analysis in the middle, 1670cm of the infrared spectrum -1 、1545cm -1 The characteristic absorption peaks of the amide groups occurring nearby indicate successful preparation of the caffeic acid derivative in example 5.
Test example 2:
determination of transdermal absorption Property
3 diffusion cells are simultaneously arranged in a transdermal diffusion tester, and the area of each cell opening is 3cm 2 The volume is 8mL, the receiving solution is 0.9% physiological saline, the penetrating skin is the abdominal skin of the mice, and the specific preparation method comprises the following steps: taking 3 mice of the same kind with close weight, scraping abdominal hair, feeding for 24 hours, removing peeled fat, removing foreign hair, cleaning with normal saline, respectively smearing the same amount of anti-aging composition test samples, smearing for 20 minutes, and transferring to a diffusion cell for transmittance detection.
The anti-aging compositions prepared in example 1, example 4, and example 7 were subjected to the above test, and the results are shown in table 1:
TABLE 1 results of percutaneous absorption test
From the data analysis in table 1, the carnosine transmittance of the anti-aging composition prepared in example 4 is obviously higher than that of examples 1 and 7, and the effect of example 7 is better than that of example 1, which shows that the prepared galactose derivative of the invention is compounded with water-soluble vitamin E to obtain a transdermal absorption enhancer which shows better transdermal promoting effect; and the galactose derivative is obtained by adopting pyrazinyl ethanethiol to chemically modify galactose, and the galactose derivative is compounded with other components, so that the transdermal absorption promoting effect of the transdermal absorption promoter can be further enhanced.
Test example 3:
investigation of proliferation effect of human skin fibroblast
Human skin fibroblasts were inoculated into MEM medium containing 5% fetal bovine serum by volume fraction, as 5% CO 2 Culturing in incubator at 37deg.C, changing liquid 1 time every 3d, culturing for 7d, and sucking out originalThe cells were washed 3 times with PBS buffer, 0.5mL of 0.25% Trypsin-1mM EDTA 4Na solution was added, followed by 10mL of MEM medium, the cells were suspended by suction, transferred to a centrifuge tube, centrifuged at 2000rpm for 5min, the supernatant removed, and an appropriate amount of MEM medium containing 5% fetal bovine serum by volume was added, and the cells were suspended by suction. Taking a 96-well plate, adding 100 [ mu ] L of cell suspension (containing 1000 cells) into each well, adding 20 [ mu ] L of a test sample, setting an equal volume of PBS buffer solution as a blank control group, culturing in an incubator for 72 hours, taking out, adding 15 [ mu ] L of WST-8 solution into each well, incubating in the incubator for 4 hours, taking out, and measuring an OD value at 450 nm.
The anti-aging compositions prepared in examples 1 to 7 and comparative examples 1 to 10 were subjected to the above test, and the results are shown in Table 2:
TABLE 2 results of human skin fibroblast proliferation effect test
From the analysis of the data in Table 2, it is clear that the OD values of the anti-aging compositions prepared using example 1 of the present invention are significantly better than those of comparative examples 1 to 5, and the effects are better than those of examples 2 and 3; meanwhile, the effects of the embodiment 2 and the embodiment 3 are obviously better than those of the comparative examples 6-10, and the composition provided by the invention has a synergistic effect when being compounded, and the combined use of 4 or 5 functional components has the effect of obviously promoting the growth of human skin fibroblasts, and has the effect of obviously promoting the growth of human skin fibroblasts compared with the independent use of the components. Example 4 has better effect than example 1 and example 7, and example 7 has better effect than example 1, which shows that the galactose derivative prepared by the invention is compounded with water-soluble vitamin E, and can be used as a transdermal absorption promoter in an anti-aging composition to further enhance the growth effect of the composition on human skin fibroblasts; and the pyrazinyl ethanethiol is adopted to chemically modify galactose to obtain galactose derivatives, and the galactose derivatives are compounded with other components, so that the enhancement effect is further improved. Example 5 is better than example 4 and example 6 is better than example 1, indicating that the caffeic acid derivative obtained by chemically modifying caffeic acid with pyridoxine hydrochloride can effectively promote the growth of human skin fibroblasts when applied in anti-aging compositions.
Type I and type III collagen secretion influence test
Adding 1000 human skin fibroblasts into each hole in a 96-hole plate, keeping the liquid change for 3 days, adding 20 mu L of test sample into each hole, and setting an equal volume of PBS buffer solution as a blank comparison group; then culturing for 7d, then measuring the content of the type I collagen and the type III collagen by adopting an ELASA method, and calculating the content improvement rate (unifying treatment is carried out on the basis of a blank control group).
The anti-aging compositions prepared in examples 1 to 7 and comparative examples 1 to 10 were subjected to the above test, and the results are shown in Table 3:
TABLE 3 results of human skin fibroblast proliferation effect test
From the data analysis in Table 3, it is clear that the anti-aging composition prepared in example 1 of the present invention has a significantly better type I and type III collagen content than comparative examples 1 to 5 and a significantly better effect than examples 2 and 3; meanwhile, the effects of the embodiment 2 and the embodiment 3 are obviously better than those of the comparative examples 6-10, which shows that the composition provided by the invention has a synergistic enhancement effect when being compounded, and the combination of 4 or 5 functional components has the effect of obviously promoting the secretion of the type I collagen and the type III collagen. Example 4 has better effect than example 1 and example 7, and example 7 has better effect than example 1, which shows that the galactose derivative prepared by the invention is compounded with water-soluble vitamin E, and can be used as a transdermal absorption promoter in an anti-aging composition to further enhance the secretion promotion effect of the composition on type I and type III collagen; and the pyrazinyl ethanethiol is adopted to chemically modify galactose to obtain galactose derivatives, and the galactose derivatives are compounded with other components, so that the enhancement effect is further improved. Example 5 is better than example 4 and example 6 is better than example 1, indicating that chemical modification of caffeic acid with pyridoxine hydrochloride to obtain caffeic acid derivatives can effectively promote the secretion of type I and type III collagen.
Test example 4:
human trial evaluation
Randomly extracting 140 healthy volunteers (the ages of 25-55 years old, women, skin photo-biological types are II-IV skin, and the facial skin has the problems of fine wrinkles, poor elasticity, darkness and the like), wherein each 10 persons are one group, the inner face of the tested person is used for 2 times within 1 day, 1mL each time is uniformly coated on the face, and the skin is cleaned by clear water after 10 minutes and continuously used for 4 weeks; can maintain the regularity of life and avoid solar ultraviolet irradiation during the study. Wherein skin elasticity is measured using a skin elasticity tester MPA580 from CK, germany, and using a Revisclometer RV600 probe; the wrinkles, the tightness and the fineness are all measured by a skin detector, and a Visia skin detector is specifically adopted.
The anti-aging compositions prepared in examples 1 to 7 and comparative examples 1 to 5 were subjected to the above test, and the results are shown in Table 4:
TABLE 4 results of human body test
From the data analysis in table 4, it is known that the skin striae-lightening rate, elasticity-improving rate, firmness-improving rate and fineness-improving rate of the subject are significantly better than those of comparative examples 1 to 5 and are better than those of examples 2 and 3 after the anti-aging composition prepared in example 1 is used; meanwhile, the effects of the embodiment 2 and the embodiment 3 are obviously better than those of the comparative examples 8-14, which shows that the composition provided by the invention has a synergistic enhancement effect when being compounded, and the combination of 4 or 5 functional components shows better action effects, especially in the aspects of improving skin elasticity, improving wrinkles and the like. The effect of example 4 is better than that of examples 1 and 7, and the effect of example 7 is better than that of example 1, which shows that the galactose derivative prepared by the invention is compounded with water-soluble vitamin E, and the galactose derivative is used as a transdermal absorption promoter in an anti-aging composition, so that the effect of the composition on skin can be further enhanced, the effect of improving the light lines and the elasticity is obviously improved, and the compactness and the fineness of the skin are further improved; and the pyrazinyl ethanethiol is adopted to chemically modify galactose to obtain galactose derivatives, and the galactose derivatives are compounded with other components, so that the enhancement effect is further improved. Example 5 is better than example 4 and example 6 is better than example 1, indicating that chemical modification of caffeic acid with pyridoxine hydrochloride to obtain caffeic acid derivatives, applied in anti-aging compositions, can effectively improve the skin wrinkling and elasticity effects of the composition.
The conventional technology in the above embodiments is known to those skilled in the art, and thus is not described in detail herein.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (5)
1. A percutaneous absorption promoter comprises glycoside derivatives and water-soluble vitamin E; the glycoside derivative comprises a galactoside derivative, wherein the structure of the galactoside derivative comprises alkyl, ester group and pyrazine; the structure of the galactoside derivative also comprises sulfur; the galactoside derivative comprises acetic anhydride and pyrazinyl ethanethiol chemically modified D-galactose products;
in the preparation of the galactoside derivative, D-galactose, acetic anhydride, glacial acetic acid and perchloric acid are taken and mixed, acetyl bromide and methanol are added for reaction to obtain an intermediate O, and the molar ratio of the D-galactose to the acetic anhydride is 1:5-7; the solid-to-liquid ratio of D-galactose to glacial acetic acid was 1g: 8-12 mL; the solid-liquid ratio of D-galactose and perchloric acid is 75-85 g:1mL; the mol ratio of acetyl bromide to D-galactose is 2.5-3:1; the volume ratio of the methanol to the acetyl bromide is 0.6-0.7:1;
mixing pyrazinyl ethanethiol, potassium carbonate, 1, 4-dioxane and water, and adding a1, 4-dioxane solution of an intermediate O to react to obtain a galactoside derivative; the molar ratio of pyrazinyl ethanethiol to potassium carbonate is 1:1.3-1.8; the solid-to-liquid ratio of pyrazinyl ethanethiol to 1, 4-dioxane is 0.08-0.1 g:1mL; the volume ratio of water to 1, 4-dioxane is 0.2-0.4:1; the mol ratio of the intermediate O to pyrazinyl ethanethiol is 1.3-1.8:1; the concentration of the 1, 4-dioxane solution of the intermediate O is 1-2 mmol/mL.
2. The percutaneous absorption enhancer according to claim 1, wherein: the mass ratio of the water-soluble vitamin E to the galactoside derivative is 1:5-20.
3. An anti-aging composition comprising the transdermal absorption enhancer of claim 1.
4. An anti-aging composition according to claim 3, wherein: the anti-aging composition comprises any 3-5 of acetyl hexapeptide-8, snake venom peptide, palmitoyl pentapeptide-4, palmitoyl tripeptide-5 and carnosine.
5. Use of the anti-aging composition of claim 3 in the preparation of a cosmetic or skin care product or medicament.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202311502272.7A CN117224418B (en) | 2023-11-13 | 2023-11-13 | Anti-aging composition and product application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202311502272.7A CN117224418B (en) | 2023-11-13 | 2023-11-13 | Anti-aging composition and product application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN117224418A CN117224418A (en) | 2023-12-15 |
CN117224418B true CN117224418B (en) | 2024-03-19 |
Family
ID=89084572
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202311502272.7A Active CN117224418B (en) | 2023-11-13 | 2023-11-13 | Anti-aging composition and product application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN117224418B (en) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101199476A (en) * | 2005-07-22 | 2008-06-18 | 云南白药集团股份有限公司 | Pennogenyl Saponins percutaneous-absorping preparation |
CN102387787A (en) * | 2009-03-19 | 2012-03-21 | 泡沫&超越有限公司 | Preparation for external application |
CN106267224A (en) * | 2015-06-01 | 2017-01-04 | 湖南师范大学 | The preparation method of galactose derivative cationic-liposome nano-particle |
CN110151593A (en) * | 2019-05-27 | 2019-08-23 | 广州瑞诗生物科技有限公司 | A kind of hyaluronic acid skin care compositions |
JP2019189548A (en) * | 2018-04-24 | 2019-10-31 | ヘンケルジャパン株式会社 | Non-oxidative hair dye and hair dying method |
CN113559006A (en) * | 2021-06-17 | 2021-10-29 | 河南农业大学 | A cosmetic composition for scavenging free radicals and resisting aging |
CN116322616A (en) * | 2020-08-26 | 2023-06-23 | 欧莱雅 | Hair lightening compositions providing damage protection and sensory benefits and methods of use |
CN117043156A (en) * | 2020-12-28 | 2023-11-10 | 格莱克特生物技术公司 | Novel galectin inhibitors of galectins |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023221797A1 (en) * | 2022-05-18 | 2023-11-23 | 四川科伦博泰生物医药股份有限公司 | Heterocyclic compound, preparation method therefor and application thereof |
-
2023
- 2023-11-13 CN CN202311502272.7A patent/CN117224418B/en active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101199476A (en) * | 2005-07-22 | 2008-06-18 | 云南白药集团股份有限公司 | Pennogenyl Saponins percutaneous-absorping preparation |
CN102387787A (en) * | 2009-03-19 | 2012-03-21 | 泡沫&超越有限公司 | Preparation for external application |
CN106267224A (en) * | 2015-06-01 | 2017-01-04 | 湖南师范大学 | The preparation method of galactose derivative cationic-liposome nano-particle |
JP2019189548A (en) * | 2018-04-24 | 2019-10-31 | ヘンケルジャパン株式会社 | Non-oxidative hair dye and hair dying method |
CN110151593A (en) * | 2019-05-27 | 2019-08-23 | 广州瑞诗生物科技有限公司 | A kind of hyaluronic acid skin care compositions |
CN116322616A (en) * | 2020-08-26 | 2023-06-23 | 欧莱雅 | Hair lightening compositions providing damage protection and sensory benefits and methods of use |
CN117043156A (en) * | 2020-12-28 | 2023-11-10 | 格莱克特生物技术公司 | Novel galectin inhibitors of galectins |
CN113559006A (en) * | 2021-06-17 | 2021-10-29 | 河南农业大学 | A cosmetic composition for scavenging free radicals and resisting aging |
Non-Patent Citations (1)
Title |
---|
侯学会 ; 李爱勤 ; 张京玉 ; .1-溴-2,3,6-三-O-乙酰基-4-氯-α-D-半乳糖的合成.河北师范大学学报(自然科学版).2012,(04),第391-394页. * |
Also Published As
Publication number | Publication date |
---|---|
CN117224418A (en) | 2023-12-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6521669B1 (en) | Hydroxystilbene compounds for reducing/inhibiting protein glycation | |
EP1021161B1 (en) | Use of ellagic acid and its derivatives in cosmetics and dermatology | |
CN102762189B (en) | Cosmetic and/or pharmaceutical composition comprising an extract of carob as active agent for activating aquaporin expression | |
KR20110099730A (en) | Peptide for inhibiting skin aging | |
JP2001048776A (en) | Extract of algae, its preparation and cosmetic or pharmaceutical composition comprising the same | |
WO2002064131A2 (en) | Inflammation-inhibiting compounds | |
CN111534455A (en) | Preparation of lactobacillus sporolysis product and application of lactobacillus sporolysis product in cosmetics | |
KR100273389B1 (en) | Use of Oligosaccharides for the Prevention and Treatment of Tissue Aging | |
CN112870102A (en) | Cosmetic composition containing glycerol glucoside and preparation method and application thereof | |
CN102459309B (en) | Bleaching peptide hydrolysate proteasome activator and compositions containing same | |
CN117224418B (en) | Anti-aging composition and product application thereof | |
CN110585053B (en) | Composition for removing freckles, fine lines, black eyes and under-eye bags and preparation method thereof | |
CN113318005A (en) | Anti-aging and anti-wrinkle composition and application thereof | |
CN114057830B (en) | Oligopeptide-1 derivatives, preparation method and application thereof | |
CN115537428A (en) | Heat shock protein-ectoin composition and preparation method and application thereof | |
CN114504545A (en) | Polypeptide and plant extraction composition for removing wrinkles and application | |
CN110876698B (en) | Active composition for regulating microenvironment of skin cells as well as preparation method and application thereof | |
JP6918002B2 (en) | Peptides used in the prophylactic and curative treatment of alopecia | |
Sakuraoka et al. | Biochemical analyses of macromolecular matrix components in patients with pseudoxanthoma elasticum | |
CN115944710A (en) | Blue copper peptide composition and application thereof | |
CN113476362B (en) | Facial skin cutin renewal promoter and application thereof | |
CN109400679B (en) | Blood fat reducing hexapeptide derived from spotted maigre swimming bladder and application thereof | |
CN117357421A (en) | External skin composition containing ergothioneine and dipeptide-1 or its derivative and application thereof | |
CN117137822B (en) | Anti-aging composition and application thereof | |
CN118206637A (en) | Transdermal polytype recombinant collagen, recombinant collagen liquid, preparation methods and applications thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |