WO2010053340A2 - Skin-whitening composition - Google Patents
Skin-whitening composition Download PDFInfo
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- WO2010053340A2 WO2010053340A2 PCT/KR2009/006597 KR2009006597W WO2010053340A2 WO 2010053340 A2 WO2010053340 A2 WO 2010053340A2 KR 2009006597 W KR2009006597 W KR 2009006597W WO 2010053340 A2 WO2010053340 A2 WO 2010053340A2
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- WO
- WIPO (PCT)
- Prior art keywords
- formula
- skin
- composition
- final concentration
- present
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 230000002087 whitening effect Effects 0.000 claims abstract description 20
- QRMPRVXWPCLVNI-YYFQZIEXSA-N Curcumol Chemical compound C1C(=C)[C@@H]2CC[C@H](C)[C@@]22C[C@@H](C(C)C)[C@]1(O)O2 QRMPRVXWPCLVNI-YYFQZIEXSA-N 0.000 claims abstract description 19
- VLGATXOTCNBWIT-UHFFFAOYSA-N rubimaillin Chemical compound O1C(C)(C)C=CC2=C1C1=CC=CC=C1C(O)=C2C(=O)OC VLGATXOTCNBWIT-UHFFFAOYSA-N 0.000 claims abstract description 19
- AKPYYGWMASCNAF-UHFFFAOYSA-N methyl 6-hydroxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate Chemical compound O1C(C)(C)CCC2=C1C1=CC=CC=C1C(O)=C2C(=O)OC AKPYYGWMASCNAF-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- RTZKSTLPRTWFEV-UHFFFAOYSA-N Isokadsuranin Natural products COC1=C2C=3C(OC)=C(OC)C(OC)=CC=3CC(C)C(C)CC2=CC2=C1OCO2 RTZKSTLPRTWFEV-UHFFFAOYSA-N 0.000 claims abstract description 11
- CUCUKLJLRRAKFN-UHFFFAOYSA-N 7-Hydroxy-(S)-usnate Chemical compound CC12C(=O)C(C(=O)C)C(=O)C=C1OC1=C2C(O)=C(C)C(O)=C1C(C)=O CUCUKLJLRRAKFN-UHFFFAOYSA-N 0.000 claims abstract description 10
- NYSZJNUIVUBQMM-BQYQJAHWSA-N Cardamonin Chemical compound COC1=CC(O)=CC(O)=C1C(=O)\C=C\C1=CC=CC=C1 NYSZJNUIVUBQMM-BQYQJAHWSA-N 0.000 claims abstract description 10
- RTZKSTLPRTWFEV-OLZOCXBDSA-N Deoxygomisin A Chemical compound COC1=C2C=3C(OC)=C(OC)C(OC)=CC=3C[C@@H](C)[C@@H](C)CC2=CC2=C1OCO2 RTZKSTLPRTWFEV-OLZOCXBDSA-N 0.000 claims abstract description 10
- GMNAPBAUIVITMI-ABNIRSKTSA-N cyclovirobuxine d Chemical compound CC(C)([C@@H](NC)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@H](C)NC)[C@H](O)C[C@@]3(C)[C@@H]1CC2 GMNAPBAUIVITMI-ABNIRSKTSA-N 0.000 claims abstract description 10
- XHCADAYNFIFUHF-TVKJYDDYSA-N esculin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)O)=CC2=C1OC(=O)C=C2 XHCADAYNFIFUHF-TVKJYDDYSA-N 0.000 claims abstract description 10
- SDHTXBWLVGWJFT-XKCURVIJSA-N oridonin Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12[C@@H](O)CCC(C)(C)[C@H]1[C@H](O)[C@@]3(O)OC2 SDHTXBWLVGWJFT-XKCURVIJSA-N 0.000 claims abstract description 10
- MBRLOUHOWLUMFF-UHFFFAOYSA-N osthole Chemical compound C1=CC(=O)OC2=C(CC=C(C)C)C(OC)=CC=C21 MBRLOUHOWLUMFF-UHFFFAOYSA-N 0.000 claims abstract description 10
- XLTFNNCXVBYBSX-UHFFFAOYSA-N wogonin Chemical compound COC1=C(O)C=C(O)C(C(C=2)=O)=C1OC=2C1=CC=CC=C1 XLTFNNCXVBYBSX-UHFFFAOYSA-N 0.000 claims abstract description 10
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 claims abstract description 9
- WNBCMONIPIJTSB-BGNCJLHMSA-N Cichoriin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1)c1c(O)cc2c(OC(=O)C=C2)c1 WNBCMONIPIJTSB-BGNCJLHMSA-N 0.000 claims abstract description 9
- QRMPRVXWPCLVNI-UHFFFAOYSA-N Curcumenol Natural products C1C(=C)C2CCC(C)C22CC(C(C)C)C1(O)O2 QRMPRVXWPCLVNI-UHFFFAOYSA-N 0.000 claims abstract description 9
- AXGWYABSYNCIMX-UHFFFAOYSA-N Cycloprotobuxin D Natural products C1CC(NC)C(C)(C)C2C31CC13CCC3(C)C(C(C)NC)CCC3(C)C1CC2 AXGWYABSYNCIMX-UHFFFAOYSA-N 0.000 claims abstract description 9
- GMNAPBAUIVITMI-UHFFFAOYSA-N Cyclovirobuxin D Natural products C1CC(NC)C(C)(C)C2C31CC13CCC3(C)C(C(C)NC)C(O)CC3(C)C1CC2 GMNAPBAUIVITMI-UHFFFAOYSA-N 0.000 claims abstract description 9
- HPUXDMUGCAWDFW-UHFFFAOYSA-N Osthole Natural products COc1ccc2CCC(=O)Oc2c1C=CC(=O)C HPUXDMUGCAWDFW-UHFFFAOYSA-N 0.000 claims abstract description 9
- HIMJIPRMECETLJ-UHFFFAOYSA-N Wogonin Natural products COc1cc(O)c(O)c2C(=O)C=C(Oc12)c3ccccc3 HIMJIPRMECETLJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- NYSZJNUIVUBQMM-UHFFFAOYSA-N alpinetin chalcone Natural products COC1=CC(O)=CC(O)=C1C(=O)C=CC1=CC=CC=C1 NYSZJNUIVUBQMM-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000009642 cyclovirobuxine D Substances 0.000 claims abstract description 9
- 229940093496 esculin Drugs 0.000 claims abstract description 9
- AWRMZKLXZLNBBK-UHFFFAOYSA-N esculin Natural products OC1OC(COc2cc3C=CC(=O)Oc3cc2O)C(O)C(O)C1O AWRMZKLXZLNBBK-UHFFFAOYSA-N 0.000 claims abstract description 9
- CAQAFLRZJHXSIS-UHFFFAOYSA-N oridonin Natural products CC1(C)C=CC(O)C23COC(O)(C(O)C12)C45C(O)C(CCC34)C(=C)C5=O CAQAFLRZJHXSIS-UHFFFAOYSA-N 0.000 claims abstract description 9
- YBZZAVZIVCBPDJ-UHFFFAOYSA-N schizandrin B Natural products COC1=C2C=3C(OC)=C(OC)C(OC)=CC=3CC(C)C(C)(O)CC2=CC2=C1OCO2 YBZZAVZIVCBPDJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229940004858 usnic acid Drugs 0.000 claims abstract description 9
- ICTZCAHDGHPRQR-UHFFFAOYSA-N usnic acid Natural products OC1=C(C)C(O)=C(C(C)=O)C2=C1C1(C)C(O)=C(C(=O)C)C(=O)C=C1O2 ICTZCAHDGHPRQR-UHFFFAOYSA-N 0.000 claims abstract description 9
- WEYVVCKOOFYHRW-UHFFFAOYSA-N usninic acid Natural products CC12C(=O)C(C(=O)C)=C(O)C=C1OC1=C2C(O)=C(C)C(O)=C1C(C)=O WEYVVCKOOFYHRW-UHFFFAOYSA-N 0.000 claims abstract description 9
- PNTWXEIQXBRCPS-NHCUHLMSSA-N Anomalin Natural products C1=CC(=O)OC2=C3[C@@H](OC(=O)C(C)=CC)[C@@H](OC(=O)C(C)=CC)C(C)(C)OC3=CC=C21 PNTWXEIQXBRCPS-NHCUHLMSSA-N 0.000 claims abstract description 7
- PNTWXEIQXBRCPS-UHFFFAOYSA-N Calipteryxin Natural products C1=CC(=O)OC2=C3C(OC(=O)C(C)=CC)C(OC(=O)C(C)=CC)C(C)(C)OC3=CC=C21 PNTWXEIQXBRCPS-UHFFFAOYSA-N 0.000 claims abstract description 7
- PNTWXEIQXBRCPS-IOWUNYDSSA-N [(9r,10r)-8,8-dimethyl-9-[(z)-2-methylbut-2-enoyl]oxy-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (z)-2-methylbut-2-enoate Chemical compound C1=CC(=O)OC2=C3[C@@H](OC(=O)C(\C)=C/C)[C@@H](OC(=O)C(\C)=C/C)C(C)(C)OC3=CC=C21 PNTWXEIQXBRCPS-IOWUNYDSSA-N 0.000 claims abstract description 7
- -1 foundation Substances 0.000 claims description 7
- 239000002674 ointment Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000007854 depigmenting agent Substances 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 1
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 abstract description 16
- 230000008099 melanin synthesis Effects 0.000 abstract description 12
- 206010014970 Ephelides Diseases 0.000 abstract description 7
- 208000003351 Melanosis Diseases 0.000 abstract description 7
- 239000002537 cosmetic Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000049 pigment Substances 0.000 abstract description 2
- 206010064127 Solar lentigo Diseases 0.000 abstract 1
- 230000008021 deposition Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 17
- 210000003491 skin Anatomy 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 208000012641 Pigmentation disease Diseases 0.000 description 5
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000019612 pigmentation Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000271 arbutin Drugs 0.000 description 3
- 210000002752 melanocyte Anatomy 0.000 description 3
- 201000001441 melanoma Diseases 0.000 description 3
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 3
- 108010024636 Glutathione Proteins 0.000 description 2
- 206010040829 Skin discolouration Diseases 0.000 description 2
- 206010040865 Skin hyperpigmentation Diseases 0.000 description 2
- 102000003425 Tyrosinase Human genes 0.000 description 2
- 108060008724 Tyrosinase Proteins 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 229960003180 glutathione Drugs 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000003061 melanogenesis Effects 0.000 description 2
- 231100000957 no side effect Toxicity 0.000 description 2
- DBGSRZSKGVSXRK-UHFFFAOYSA-N 1-[2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]acetyl]-3,6-dihydro-2H-pyridine-4-carboxylic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CCC(=CC1)C(=O)O DBGSRZSKGVSXRK-UHFFFAOYSA-N 0.000 description 1
- XYLOFRFPOPXJOQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperazine-1-carbonyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(Cn1cc(c(n1)C(=O)N1CCNCC1)-c1cnc(NC2Cc3ccccc3C2)nc1)N1CCc2n[nH]nc2C1 XYLOFRFPOPXJOQ-UHFFFAOYSA-N 0.000 description 1
- XYPHRTDTBOZCJF-UHFFFAOYSA-N Anomaline Natural products CCC12CCC3N(C(=O)C)c4c(O)c(OC)ccc4C35CCN(CCC1O)C25 XYPHRTDTBOZCJF-UHFFFAOYSA-N 0.000 description 1
- 241000521299 Deinocerites cancer Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- AHMIDUVKSGCHAU-UHFFFAOYSA-N Dopaquinone Natural products OC(=O)C(N)CC1=CC(=O)C(=O)C=C1 AHMIDUVKSGCHAU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 208000001382 Experimental Melanoma Diseases 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- AHMIDUVKSGCHAU-LURJTMIESA-N L-dopaquinone Chemical compound [O-]C(=O)[C@@H]([NH3+])CC1=CC(=O)C(=O)C=C1 AHMIDUVKSGCHAU-LURJTMIESA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000008260 defense mechanism Effects 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 208000031066 hyperpigmentation of the skin Diseases 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 1
- 229960004705 kojic acid Drugs 0.000 description 1
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- SFMJNHNUOVADRW-UHFFFAOYSA-N n-[5-[9-[4-(methanesulfonamido)phenyl]-2-oxobenzo[h][1,6]naphthyridin-1-yl]-2-methylphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(C)=CC=C1N1C(=O)C=CC2=C1C1=CC(C=3C=CC(NS(C)(=O)=O)=CC=3)=CC=C1N=C2 SFMJNHNUOVADRW-UHFFFAOYSA-N 0.000 description 1
- 230000024181 negative regulation of developmental pigmentation Effects 0.000 description 1
- 229940021584 osthol Drugs 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 231100001068 severe skin irritation Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000012588 trypsin Substances 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
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
Definitions
- the present invention relates to a cosmetic for skin whitening, and more particularly, cyclovirobuxine D, osthole, anomaline , Esculin, cardamonin, usnic acid, ordonin, oridonin, schizandrin B, curcumol, mollugin, wogo
- the present invention relates to a nin (wogonin), a dihydromollugin compound, and a composition for skin whitening containing the same, and more particularly, to an external skin composition having an excellent whitening effect.
- Melanogenesis is a defense mechanism against melanocyte melanocytes (melanocytes) that stimulate the production of melanin, which increases melanogenesis, which is transferred to keratinocytes and accumulated in the skin epidermis.
- melanin protects the skin
- hyperpigmentation of the skin causes blemishes, freckles, darkening of the skin after skin inflammation, and senile pigment spots. It may also result.
- the melanin production process is made by tyrosinase, an amino acid called tyrosinase, which is transformed into dopa and dopaquinone, followed by a non-enzymatic oxidation reaction. It is known that spots, blotch, etc. are produced.
- thiol-based compounds such as glutathione and cysteine not only have a characteristic unpleasant odor, but also have problems with transdermal absorption, and glycosides and derivatives thereof have high polarity, making it difficult to use as a cosmetic ingredient.
- the present invention has no side effects on the skin, and excellent in inhibiting melanin production to provide a composition for skin whitening excellent in inhibiting skin pigmentation.
- the present invention provides a melanin production inhibitor selected from the group consisting of compounds represented by the following formulas 1 to 12 excellent in melanin inhibitory effect and whitening effect.
- the present invention also provides a skin whitening agent selected from the group consisting of the compounds represented by Formulas 1 to 12 and a composition for skin whitening containing any one or more of these as an active ingredient.
- compositions such as cosmetics containing as a component can be used very effectively to improve skin hyperpigmentation, such as blemishes, freckles, aging spots and to realize skin whitening.
- the present invention is cyclovirobuxine D of Formula 1 (Cyvivirobuxine D, C 26 H 46 N 2 O, CAS No. 860-79-7), Osthol (Formula 2, C 15 H 16 O 3 , CAS) No. 484-12-8), anmalin of Formula 3 (C 24 H 26 O 7 , CAS No. 81740-07-0), esculin of Formula 4 (C 15 H 16 O 9 , CAS No. 531-75-9), cardamonin of Formula 5 (C 16 H 14 O 4 , CAS No. 18956-16-6), usnic acid of Formula 6 (C 18 H 16 O 7 , CAS No. 125-46-2), orridinin (C20H28O6, CAS No.
- the present inventors conducted a new whitening agent study on native plants and animals using B16 mouse melanoma cells capable of screening even substances that inhibit melanin synthesis induction.
- the compounds of compounds 1 to 5 have been found to have a very strong melanin production inhibitory effect and a whitening effect to complete the present invention.
- the compounds of Formulas 1 to 12 mentioned above may be easily purchased on the market, or each may be used alone or in combination of two or more kinds thereof, such as skin, lotion, cream, foundation, essence, gel, pack, foam cleansing, soap, etc.
- An effective amount may be added to various compositions such as ointments to exhibit skin lightening effects.
- the amount of the compound added is preferably 0.00001 to 10% by weight based on the total weight of the composition, more preferably 0.001 to 1.0% by weight.
- Table 1 sample Melanin production % Inhibition Control group (no addition) 0.044 ⁇ 0.004 - arbutin (final concentration 300 ⁇ g / ml) 0.028 ⁇ 0.004 36 cyclovirobuxine D (final concentration 5 ⁇ g / ml) 0.019 ⁇ 0.003 57 cyclovirobuxine D (final concentration 20 ⁇ g / ml) 0.012 ⁇ 0.002 73 osthole (final concentration 5 ⁇ g / ml) 0.038 ⁇ 0.001 14 osthole (final concentration 20 ⁇ g / ml) 0.028 ⁇ 0.003 36 anomalin (final concentration 5 ⁇ g / ml) 0.025 ⁇ 0.002 43 anomalin (final concentration 20 ⁇ g / ml) 0.018 ⁇ 0.002 59 esculin (final concentration 5 ⁇ g / ml) 0.036 ⁇ 0.002 18 esculin (final concentration 20 ⁇ g / m
- the compounds of Formulas 1 to 12 showed excellent melanin production inhibitory activity even at low concentrations against melanoma cells of cultured rats, compared with arbutin, a whitening substance known in the art, and cytotoxicity Did not appear. This indicates that the present invention can be very useful for improving blemishes and freckles and skin whitening.
- the external application ointment of Preparation Examples 1 to 12 showed a whitening effect on at least 12 of 20 subjects, and showed no side effects in the skin and was safe and improved freckles and freckles. It can be seen that the skin whitening agent has an excellent effect on.
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Abstract
The present invention relates to a skin-whitening cosmetic containing a compound having an activity which inhibits melanin production. A characterising feature of the skin-whitening cosmetic of the present invention is that it contains at least one active component selected from the group comprising cyclovirobuxine D, osthole, anomalin, esculin, cardamonin, usnic acid, oridonin, schizandrin B, curcumol, mollugin, wogonin, dihydromollugin and mixtures thereof. The compounds of the present invention inhibit the production of melanin and have an outstanding effect in hindering pigment deposition. Consequently, a composition such as a cosmetic containing one or more of these compounds as an active component can be used very effectively in skin whitening such as in improving liver spots and freckles.
Description
본 발명은 피부미백용 화장료에 관한 것으로서, 보다 상세하게는 피부에 대한 부작용없이 안전하게 사용될 수 있으며 멜라닌 생성 억제 활성을 갖는 사이클로비로북신 디(cyclovirobuxine D), 오스톨(osthole), 아노말린(anomalin), 에스쿨린(esculin), 카르다모닌(cardamonin), 우스닌산(usnic acid), 오리도닌(oridonin), 스키잔드린 비(schizandrin B), 쿠르쿠몰(curcumol), 몰루긴(mollugin), 우고닌(wogonin), 디히드로몰루긴(dihydromollugin) 화합물 및 이를 함유한 피부 미백용 조성물에 관한 것으로서, 보다 상세하게는 미백효과가 우수한 피부외용제 조성물에 관한 것이다.The present invention relates to a cosmetic for skin whitening, and more particularly, cyclovirobuxine D, osthole, anomaline , Esculin, cardamonin, usnic acid, ordonin, oridonin, schizandrin B, curcumol, mollugin, wogo The present invention relates to a nin (wogonin), a dihydromollugin compound, and a composition for skin whitening containing the same, and more particularly, to an external skin composition having an excellent whitening effect.
피부흑화(melanogenesis)는 멜라닌 색소생성세포(melanocyte)에서 자외선 등의 자극에 대한 방어기작으로 멜라닌 생성활동이 증가되고 이로 말미암아 만들어진 다량의 멜라닌이 각질형성세포(keratinocyte)로 전이되어 피부표피층에 축척된 결과이다. 비록 멜라닌이 피부보호작용을 하나 피부의 과색소침착은 기미, 주근깨, 피부염증 후의 피부흑화, 노인성 색소반점 등을 일으키며 이로 인해 당사자에게 미용상의 불편뿐만 아니라 정신적으로 부정적인 영향을 미쳐 사회활동에 불편을 초래하기도 한다. 멜라닌 생성 과정은 아미노산의 일종인 티로신(tyrosine)에 티로시나제(tyrosinase)라는 효소가 작용하여 도파(DOPA), 도파퀴논(dopaquinone)으로 바뀐 후 비효소적인 산화 반응을 거쳐 만들어 지며, 이것이 피부 내에 이상침착하여 기미, 검버섯 등이 생기는 것이라고 알려져 있다. 이와 같은 색소침착, 기미, 반점 등의 완화, 예방 및 치료에는 멜라닌 생성을 억제하는 물질, 예를 들면 하이드로퀴논(hydroquinone), 알부틴(arbutin), 아스콜빈산(ascorbic acid), 코지산(kojic acid), 글루타티온(glutathione) 등이 개발되어 이들을 화장료에 배합하므로써 피부미백을 실현하거나, 기미 및 주근깨 등의 피부 과색소 침착증을 개선하였다. 그러나, 하이드로퀴논은 일단 효과가 인정되고 있지만 피부 자극성이 심하여 일반적으로 사용이 제한되고 있다. 아스콜빈산은 쉽게 산화되어, 이를 배합한 화장료는 변색, 변취되는 등의 문제를 야기한다. 또한, 글루타티온, 시스테인 등의 티올계 화합물은 특유의 불쾌한 냄새를 가질 뿐만 아니라 경피흡수에도 문제점이 있고, 이들의 배당체 및 유도체들도 극성이 높으므로 화장료의 배합 성분으로 사용하기는 어렵다.Melanogenesis is a defense mechanism against melanocyte melanocytes (melanocytes) that stimulate the production of melanin, which increases melanogenesis, which is transferred to keratinocytes and accumulated in the skin epidermis. The result is. Although melanin protects the skin, hyperpigmentation of the skin causes blemishes, freckles, darkening of the skin after skin inflammation, and senile pigment spots. It may also result. The melanin production process is made by tyrosinase, an amino acid called tyrosinase, which is transformed into dopa and dopaquinone, followed by a non-enzymatic oxidation reaction. It is known that spots, blotch, etc. are produced. To alleviate, prevent and treat pigmentation, blemishes, and spots, substances that inhibit melanin production, such as hydroquinone, arbutin, ascorbic acid, and kojic acid ) And glutathione have been developed and blended with cosmetics to achieve skin whitening or improve skin hyperpigmentation such as blemishes and freckles. However, although hydroquinone is once recognized for its effectiveness, its use is generally limited due to severe skin irritation. Ascorbic acid is easily oxidized, and the cosmetics containing the same cause problems such as discoloration and deodorization. In addition, thiol-based compounds such as glutathione and cysteine not only have a characteristic unpleasant odor, but also have problems with transdermal absorption, and glycosides and derivatives thereof have high polarity, making it difficult to use as a cosmetic ingredient.
상기와 같은 문제점을 해결하기 위한 것으로서, 본 발명은 피부에 대한 부작용이 없으며, 멜라닌 생성 억제 효과가 우수하여 피부 색소침착 저해효과가 뛰어난 피부미백용 조성물을 제공하는 데 있다. In order to solve the above problems, the present invention has no side effects on the skin, and excellent in inhibiting melanin production to provide a composition for skin whitening excellent in inhibiting skin pigmentation.
상기와 같은 기술적 과제를 해결하기 위하여, 본 발명은 멜라닌 억제 효과 및 미백 효과가 뛰어난, 하기 화학식 1 내지 12로 표시되는 화합물로 이루어진 군으로부터 선택된 멜라닌 생성 저해제를 제공한다.In order to solve the above technical problem, the present invention provides a melanin production inhibitor selected from the group consisting of compounds represented by the following formulas 1 to 12 excellent in melanin inhibitory effect and whitening effect.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
[화학식3][Formula 3]
[화학식4][Formula 4]
[화학식5][Formula 5]
[화학식6][Formula 6]
[화학식7][Formula 7]
[화학식8][Formula 8]
[화학식9][Formula 9]
[화학식10][Formula 10]
[화학식11][Formula 11]
[화학식12][Formula 12]
또한, 본 발명은 상기 화학식 1 내지 12로 표시되는 화합물로 이루어진 군으로부터 선택된 피부미백제 및 이들 중 어느 하나 이상을 유효성분으로 함유하는 피부미백용 조성물을 제공한다.The present invention also provides a skin whitening agent selected from the group consisting of the compounds represented by Formulas 1 to 12 and a composition for skin whitening containing any one or more of these as an active ingredient.
이와 같이, 본 발명의 사이클로비로북신 디(cyclovirobuxine D), 오스톨(osthole), 아노말린(anomalin), 에스쿨린(esculin), 카르다모닌(cardamonin), 우스닌산(usnic acid), 오리도닌(oridonin), 스키잔드린 비(schizandrin B), 쿠르쿠몰(curcumol), 몰루긴(mollugin), 우고닌(wogonin) 및 디히드로몰루긴(dihydromollugin)은 멜라닌 세포의 멜라닌 생성을 저해하므로, 이들을 유효성분으로 함유하는 화장료 등의 조성물은 기미, 주근깨 개선, 노인성 반점 등의 피부 과색소 핌착증을 개선하고 피부미백을 실현하는데 매우 효과적으로 사용될 수 있다. Thus, cyclovirobuxine D, osthole, anomalin, esculin, cardamonin, usnic acid, oridonin of the present invention (oridonin), schizandrin B, curcumol, mollugin, wogonin and dihydromollugin inhibit melanin production in melanocytes Compositions, such as cosmetics containing as a component can be used very effectively to improve skin hyperpigmentation, such as blemishes, freckles, aging spots and to realize skin whitening.
이하 본 발명을 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 상기 화학식 1의 사이클로비로북신 디(cyclovirobuxine D, C26H46N2O, CAS No. 860-79-7), 상기화학식 2의 오스톨(osthole, C15H16O3, CAS No. 484-12-8), 상기 화학식 3의 아노말린(anomalin, C24H26O7, CAS No. 81740-07-0), 상기 화학식 4의 에스쿨린(esculin, C15H16O9, CAS No. 531-75-9), 상기 화학식 5의 카르다모닌(cardamonin, C16H14O4, CAS No. 18956-16-6), 상기 화학식 6의 우스닌산(usnic acid, C18H16O7, CAS No. 125-46-2), 상기 화학식 7의 오리도닌(oridonin, C20H28O6, CAS No. 28957-04-2), 상기 화학식 8의 스키잔드린 비(schizandrin B, C23H28O6, CAS No. 61281-37-6), 상기 화학식 9의 쿠르쿠몰(curcumol, C15H24O2, CAS No. 4871-97-0), 화학식 10의 몰루긴(mollugin, C17H16O4, CAS No. 55481-88-4, M.W. : 284.3), 상기 화학식 11의 우고닌(wogonin, C16H12O5, CAS No. 632-85-9, M.W. : 284.3) 및 상기 화학식 12의 디히드로몰루긴(dihydromollugin, C17H18O4, M.W. : 286.3) 중 어느 하나로 된 멜라닌 생성 저해제를 제공한다.The present invention is cyclovirobuxine D of Formula 1 (Cyvivirobuxine D, C 26 H 46 N 2 O, CAS No. 860-79-7), Osthol (Formula 2, C 15 H 16 O 3 , CAS) No. 484-12-8), anmalin of Formula 3 (C 24 H 26 O 7 , CAS No. 81740-07-0), esculin of Formula 4 (C 15 H 16 O 9 , CAS No. 531-75-9), cardamonin of Formula 5 (C 16 H 14 O 4 , CAS No. 18956-16-6), usnic acid of Formula 6 (C 18 H 16 O 7 , CAS No. 125-46-2), orridinin (C20H28O6, CAS No. 28957-04-2) of Formula 7, the skizandrin ratio of Scheme 8 (schizandrin B, C 23 H 28 O6, CAS No. 61281-37-6), curcumol of Formula 9 (C 15 H24O2, CAS No. 4871-97-0), mollugin (C17H16O4, CAS No. 10) 55481-88-4, MW: 284.3, wogonin of Formula 11 (C16H12O5, CAS No. 632-85-9, MW: 284.3) and dihydromollugin of Formula 12 (C 1) 7 H18O4, MW: 286.3).
본 발명자는 멜라닌 합성 유도 자체를 억제하는 물질까지 스크리닝(screening)할 수 있는 쥐의 멜라노마 세포(B16 mouse melanoma cell)를 이용하여 천연에서 자생하는 동식물들을 대상으로 신규 미백제 연구를 거듭한 결과, 상기 화합물 1 내지 5의 화합물들이 매우 강력한 멜라닌 생성 억제 효과와 미백 효과가 있음을 밝혀내어 본 발명을 완성하게 되었다.The present inventors conducted a new whitening agent study on native plants and animals using B16 mouse melanoma cells capable of screening even substances that inhibit melanin synthesis induction. The compounds of compounds 1 to 5 have been found to have a very strong melanin production inhibitory effect and a whitening effect to complete the present invention.
전술한 화학식 1 내지 12의 화합물들은 시중에서 용이하게 구입할 수 있는데, 각각 단독으로 또는 2종 이상을 혼합하여, 스킨, 로션, 크림, 파운데이션, 에센스, 젤, 팩, 폼 클렌징, 비누 등의 화장료나 연고와 같은 다양한 조성물에 유효량 첨가되어 피부 미백 효과를 나타낼 수 있다. 피부 미백 효과와 경제성을 고려할 때, 상기 화합물들의 첨가량은 조성물 총 중량을 기준으로 0.00001 내지 10 중량%인 것이 바람직한데, 더욱 바람직하게는 0.001 내지 1.0 중량%이다.The compounds of Formulas 1 to 12 mentioned above may be easily purchased on the market, or each may be used alone or in combination of two or more kinds thereof, such as skin, lotion, cream, foundation, essence, gel, pack, foam cleansing, soap, etc. An effective amount may be added to various compositions such as ointments to exhibit skin lightening effects. In consideration of the skin lightening effect and economical efficiency, the amount of the compound added is preferably 0.00001 to 10% by weight based on the total weight of the composition, more preferably 0.001 to 1.0% by weight.
이하, 본 발명을 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 발명에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되어서는 안된다. 본 발명의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해서 제공되는 것이다.Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present invention can be modified in many different forms, the scope of the present invention should not be construed as limited to the embodiments described below. The embodiments of the present invention are provided to more completely explain the present invention to those skilled in the art.
실험예 1. 세포 수준에서의 멜라닌 생성 저해 효과 시험Experimental Example 1. Test of melanin production inhibitory effect at the cellular level
시판되는 화학식 1 내지 12의 화합물을 구입하여 사용하였다. 각 화합물들을 쥐의 멜라노마 세포(B-16 mouse melanoma cell)의 배양액에 첨가하여 세포 수준에서의 미백 효과를 다음과 같이 실험하였다(Lotan R., Lotan D. Cancer Res. 40:3345-3350, 1980). 각 화합물들을 최종 농도가 5 ㎍/ml, 20㎍/m가 되도록 하여 B-16 멜라노마 세포의 배양시 배양액에 첨가하고, 3일간 배양한 후 세포들을 트립신(Trypsin)으로 처리하고, 배양 용기로부터 떼어내 원심 분리한 후, 멜라닌을 추출하였다. 추출된 멜라닌에 수산화 나트륨용액(1N 농도) 1 ml를 가하여 약 10 분 동안 끓여 멜라닌을 녹이고, 분광 광도계로 400 나노미터(nm)에서 흡광도를 측정하여 생성된 멜라닌의 양을 단위 세포 수당(106 cell)의 흡광도를 나타내는 방법으로 실험을 수행하였다. 이와 같은 실험을 3회 반복하고 그 평균값을 사용하여 대조군에 대한 상대적인 멜라닌 생성량을 저해율(%)로 계산하고, 그 결과를 하기 표 1에 나타내었다.Commercially available compounds of Formulas 1-12 were purchased and used. Each compound was added to the culture medium of B-16 mouse melanoma cells, and the whitening effect at the cellular level was tested as follows (Lotan R., Lotan D. Cancer Res. 40: 3345-3350, 1980). Each compound was added to the culture medium at the final concentration of 5 μg / ml, 20 μg / m, and cultured for B-16 melanoma cells, incubated for 3 days, and treated with trypsin, and then from the culture vessel. After stripping off and centrifugation, melanin was extracted. Sodium hydroxide solution to the extraction of melanin (1N concentration) 1 ml and the reaction mixture was dissolved melanin boiled for about 10 minutes, the amount of the produced melanin by measuring the absorbance at 400 nanometers (nm) with a spectrophotometer unit cell allowance (10 6 The experiment was carried out by a method showing the absorbance of the cell). The experiment was repeated three times and the average value was used to calculate the relative melanin production relative to the control group as inhibition rate (%), and the results are shown in Table 1 below.
표 1
Table 1
| 시료 | 멜라닌 생성양 | 저해율(%) |
| 대조군(무첨가) | 0.044 ± 0.004 | - |
| arbutin(최종농도 300 ㎍/ml) | 0.028 ± 0.004 | 36 |
| cyclovirobuxine D(최종농도 5 ㎍/ml) | 0.019 ± 0.003 | 57 |
| cyclovirobuxine D(최종농도 20 ㎍/ml) | 0.012 ± 0.002 | 73 |
| osthole(최종농도 5 ㎍/ml) | 0.038 ± 0.001 | 14 |
| osthole(최종농도 20 ㎍/ml) | 0.028 ± 0.003 | 36 |
| anomalin(최종농도 5 ㎍/ml) | 0.025 ± 0.002 | 43 |
| anomalin(최종농도 20 ㎍/ml) | 0.018 ± 0.002 | 59 |
| esculin(최종농도 5 ㎍/ml) | 0.036 ± 0.002 | 18 |
| esculin(최종농도 20 ㎍/ml) | 0.028 ± 0.003 | 36 |
| cardamonin(최종농도 5 ㎍/ml) | 0.032 ± 0.001 | 27 |
| cardamonin(최종농도 20 ㎍/ml) | 0.022 ± 0.003 | 50 |
| usnic acid(최종농도 5 ㎍/ml) | 0.034 ± 0.001 | 23 |
| usnic acid(최종농도 20 ㎍/ml) | 0.022 ± 0.002 | 50 |
| oridonin(최종농도 5 ㎍/ml) | 0.036 ± 0.001 | 18 |
| oridonin(최종농도 20 ㎍/ml) | 0.028 ± 0.003 | 36 |
| schizandrin B(최종농도 5 ㎍/ml) | 0.025 ± 0.002 | 43 |
| schizandrin B(최종농도 20 ㎍/ml) | 0.018 ± 0.002 | 59 |
| curcumol(최종농도 5 ㎍/ml) | 0.038 ± 0.002 | 16 |
| curcumol(최종농도 20 ㎍/ml) | 0.028 ± 0.003 | 36 |
| mollugin(최종농도 5 ㎍/ml) | 0.034 ± 0.001 | 23 |
| mollugin(최종농도 20 ㎍/ml) | 0.020 ± 0.003 | 55 |
| wogonin(최종농도 5 ㎍/ml) | 0.036 ± 0.002 | 18 |
| wogonin(최종농도 20 ㎍/ml) | 0.028 ± 0.002 | 36 |
| dihydromollugin(최종농도 5 ㎍/ml) | 0.030 ± 0.002 | 32 |
| dihydromollugin(최종농도 20 ㎍/ml) | 0.014 ± 0.003 | 68 |
| sample | Melanin production | % Inhibition |
| Control group (no addition) | 0.044 ± 0.004 | - |
| arbutin (final concentration 300 ㎍ / ml) | 0.028 ± 0.004 | 36 |
| cyclovirobuxine D (final concentration 5 ㎍ / ml) | 0.019 ± 0.003 | 57 |
| cyclovirobuxine D (final concentration 20 ㎍ / ml) | 0.012 ± 0.002 | 73 |
| osthole (final concentration 5 ㎍ / ml) | 0.038 ± 0.001 | 14 |
| osthole (final concentration 20 ㎍ / ml) | 0.028 ± 0.003 | 36 |
| anomalin (final concentration 5 ㎍ / ml) | 0.025 ± 0.002 | 43 |
| anomalin (final concentration 20 ㎍ / ml) | 0.018 ± 0.002 | 59 |
| esculin (final concentration 5 ㎍ / ml) | 0.036 ± 0.002 | 18 |
| esculin (final concentration 20 ㎍ / ml) | 0.028 ± 0.003 | 36 |
| cardamonin (final concentration 5 ㎍ / ml) | 0.032 ± 0.001 | 27 |
| cardamonin (final concentration 20 ㎍ / ml) | 0.022 ± 0.003 | 50 |
| usnic acid (final concentration 5 ㎍ / ml) | 0.034 ± 0.001 | 23 |
| usnic acid (final concentration 20 ㎍ / ml) | 0.022 ± 0.002 | 50 |
| oridonin (final concentration 5 ㎍ / ml) | 0.036 ± 0.001 | 18 |
| oridonin (final concentration 20 ㎍ / ml) | 0.028 ± 0.003 | 36 |
| schizandrin B (final concentration 5 ㎍ / ml) | 0.025 ± 0.002 | 43 |
| schizandrin B (final concentration 20 ㎍ / ml) | 0.018 ± 0.002 | 59 |
| curcumol (final concentration 5 ㎍ / ml) | 0.038 ± 0.002 | 16 |
| curcumol (final concentration 20 ㎍ / ml) | 0.028 ± 0.003 | 36 |
| mollugin (final concentration 5 ㎍ / ml) | 0.034 ± 0.001 | 23 |
| mollugin (final concentration 20 ㎍ / ml) | 0.020 ± 0.003 | 55 |
| wogonin (final concentration 5 ㎍ / ml) | 0.036 ± 0.002 | 18 |
| wogonin (final concentration 20 ㎍ / ml) | 0.028 ± 0.002 | 36 |
| dihydromollugin (final concentration 5 ㎍ / ml) | 0.030 ± 0.002 | 32 |
| dihydromollugin (final concentration 20 ㎍ / ml) | 0.014 ± 0.003 | 68 |
반복수 = 3 Iterations = 3
상기 표 1에서 보는 바와 같이, 화학식 1 내지 12의 화합물들은 종래에 알려진 미백 물질인 알부틴(arbutin)과 비교할 때, 배양된 쥐의 멜라노마 세포에 대하여 낮은 농도에서도 우수한 멜라닌 생성 억제능을 보였으며 세포독성은 나타나지 않았다. 이는 본 발명이 기미나 주근깨 개선 및 피부 미백에 매우 유용하게 사용될 수 있다는 것을 나타냈다.As shown in Table 1, the compounds of Formulas 1 to 12 showed excellent melanin production inhibitory activity even at low concentrations against melanoma cells of cultured rats, compared with arbutin, a whitening substance known in the art, and cytotoxicity Did not appear. This indicates that the present invention can be very useful for improving blemishes and freckles and skin whitening.
제조예 1 내지 12 및 비교예 1Preparation Examples 1 to 12 and Comparative Example 1
하기 표 2와 표 3에 나타낸 각각의 성분을 하기 표 2와 표 3에 나타난 비율과 같이 혼합하여 피부 외용 연고를 제조하였다. Each of the ingredients shown in Table 2 and Table 3 were mixed in the same ratio as shown in Tables 2 and 3 to prepare an external skin ointment.
[규칙 제91조에 의한 정정 10.12.2009]
[Revision 10.12.2009 by Rule 91]
*: 전체가 100 중량%가 되도록 하는 양 *: Amount to be 100% by weight in total
[규칙 제91조에 의한 정정 10.12.2009]
[Revision 10.12.2009 by Rule 91]
*: 전체가 100 중량%가 되도록 하는 양 *: Amount to be 100% by weight in total
전술한 조성으로 제조한 피부 외용 연구에 대한 피부미백효과를 검증하기 위하여, 다음과 같이 색소침착 저해 및 기미 개선 실험을 실시하였다. In order to verify the skin whitening effect on the skin external study prepared with the above-described composition, pigmentation inhibition and blemish improvement experiments were performed as follows.
실험예 2. 색소침착 저해효과 실험Experimental Example 2. Pigmentation Inhibition Effect Experiment
피시험자로 건강한 남녀 40명을 선정하여 양팔의 하박부에 직경 7 mm 크기의 구멍이 6 개씩 2 줄로 파인 알루미늄 호일을 덮은 후, 팔에서 10 cm 거리에서 일광 조사기(ORIEL Solar Simulator 1000W)로 60 mJ/㎠의 광량을 조사하였다. 조사하기 3일 전부터 조사 후 3주 째까지 1일 2회씩 제조예 1-12 및 비교예 1에 따라 제조된 기제를 한 쌍으로 같은 줄에 도포하였다. 각각에 대하여 제조예와 비교예의 색소 침착도를 육안으로 판정하고, 제조예가 비교예에 비해 색소침착을 억제한 정도를 효과있음, 차이없음의 2단계로 평가하였으며, 그 결과는 표 4과 같다.Forty healthy men and women were selected and covered with aluminum foil in two rows of six holes with a diameter of 7 mm in the lower part of both arms, and 60 mJ with a ORIEL Solar Simulator 1000W at a distance of 10 cm from the arm. The amount of light of / cm 2 was investigated. The bases prepared according to Preparation Examples 1-12 and Comparative Example 1 were applied twice a day twice a day from 3 days before irradiation to 3 weeks after irradiation. For each, the degree of pigmentation of the preparation example and the comparative example was visually determined, and the degree of inhibition of pigmentation in the preparation example compared to the comparative example was evaluated in two steps: effective and no difference.
표 4
Table 4
| 실험물질 | 효과 있음(명) | 차이없음(명) |
| 제조예 1 | 14 | 6 |
| 제조예 2 | 14 | 6 |
| 제조예 3 | 16 | 4 |
| 제조예 4 | 12 | 8 |
| 제조예 5 | 13 | 7 |
| 제조예 6 | 15 | 5 |
| 제조예 7 | 14 | 6 |
| 제조예 8 | 16 | 4 |
| 제조예 9 | 15 | 5 |
| 제조예 10 | 17 | 3 |
| 제조예 11 | 15 | 5 |
| 제조예 12 | 19 | 1 |
| Experimental substance | Effective (persons) | No difference (persons) |
| Preparation Example 1 | 14 | 6 |
| Preparation Example 2 | 14 | 6 |
| Preparation Example 3 | 16 | 4 |
| Preparation Example 4 | 12 | 8 |
| Preparation Example 5 | 13 | 7 |
| Preparation Example 6 | 15 | 5 |
| Preparation Example 7 | 14 | 6 |
| Preparation Example 8 | 16 | 4 |
| Preparation Example 9 | 15 | 5 |
| Preparation Example 10 | 17 | 3 |
| Preparation Example 11 | 15 | 5 |
| Preparation Example 12 | 19 | One |
상기 표 4의 결과에서 볼 수 있듯이, 제조예 1 내지 12의 피부 외용 연고는 피시험자 20명 중에서 최소 12명에 대하여 미백 효과를 나타내었으며, 피부 내에서 어떤 부작용도 나타나지 않아 안전하고 기미나 주근깨 개선에 우수한 효과가 있는 피부미백제임을 알 수 있다.As can be seen from the results of Table 4, the external application ointment of Preparation Examples 1 to 12 showed a whitening effect on at least 12 of 20 subjects, and showed no side effects in the skin and was safe and improved freckles and freckles. It can be seen that the skin whitening agent has an excellent effect on.
Claims (4)
- 하기 화학식 1 내지 12로 표시되는 화합물로 이루어진 군으로부터 선택된 피부미백제.A skin lightening agent selected from the group consisting of compounds represented by formulas (1) to (12).[화학식 1][Formula 1]cyclovirobuxine Dcyclovirobuxine D[화학식 2][Formula 2]ostholeosthole[화학식3][Formula 3]anomalinanomalin[화학식4][Formula 4]esculinesculin[화학식5][Formula 5]cardamonincardamonin[화학식6][Formula 6]usnic acidusnic acid[화학식7][Formula 7]oridoninoridonin[화학식8][Formula 8]schizandrin Bschizandrin B[화학식9][Formula 9]curcumolcurcumol[화학식10][Formula 10]molluginmollugin[화학식11][Formula 11]wogoninwogonin[화학식12][Formula 12]dihydromollugindihydromollugin
- 하기 화학식 1 내지 12로 표시되는 화합물로 이루어진 군으로부터 선택된 어느 하나 이상을 유효성분으로 함유하는 것을 특징으로 하는 피부미백용 조성물.A skin whitening composition comprising any one or more selected from the group consisting of compounds represented by Formulas 1 to 12 as an active ingredient.[화학식 1][Formula 1]cyclovirobuxine Dcyclovirobuxine D[화학식 2][Formula 2]ostholeosthole[화학식3][Formula 3]anomalinanomalin[화학식4][Formula 4]esculinesculin[화학식5][Formula 5]cardamonincardamonin[화학식6][Formula 6]usnic acidusnic acid[화학식7][Formula 7]oridoninoridonin[화학식8][Formula 8]schizandrin Bschizandrin B[화학식9][Formula 9]curcumolcurcumol[화학식10][Formula 10]molluginmollugin[화학식11][Formula 11]wogoninwogonin[화학식12][Formula 12]dihydromollugindihydromollugin
- 제 2항에 있어서, 상기 유효성분의 함량은 조성물 총 중량을 기준으로 0.00001 내지 10 중량%인 것을 특징으로하는 피부미백용 조성물.The composition for skin whitening according to claim 2, wherein the content of the active ingredient is 0.00001 to 10 wt% based on the total weight of the composition.
- 제 2항에 있어서, 상기 피부미백용 조성물은 스킨, 로션, 크림, 파운데이션, 에센스, 젤, 팩, 품 클렌징 및 연고로 이루어진 군으로부터 선택된 어느 하나의 제형으로 형성된 것을 특징으로 하는 피부미백용 조성물.The composition for skin whitening according to claim 2, wherein the composition for skin whitening is formed in any one formulation selected from the group consisting of skin, lotion, cream, foundation, essence, gel, pack, product cleansing and ointment.
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| Application Number | Priority Date | Filing Date | Title |
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| KR1020080110968A KR101462692B1 (en) | 2008-11-10 | 2008-11-10 | Skin whitening cosmetics |
| KR10-2008-0110968 | 2008-11-10 | ||
| KR1020080120364A KR20100061978A (en) | 2008-12-01 | 2008-12-01 | Skin whitening agent |
| KR10-2008-0120364 | 2008-12-01 | ||
| KR10-2009-0083426 | 2009-09-04 | ||
| KR1020090083426A KR20110025387A (en) | 2009-09-04 | 2009-09-04 | Skin Whitening Composition |
| KR10-2009-0108077 | 2009-11-10 | ||
| KR1020090108077A KR20110051476A (en) | 2009-11-10 | 2009-11-10 | Skin Whitening Composition |
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