JPS6229528A - 酵素阻害剤およびその製造方法 - Google Patents
酵素阻害剤およびその製造方法Info
- Publication number
- JPS6229528A JPS6229528A JP60168309A JP16830985A JPS6229528A JP S6229528 A JPS6229528 A JP S6229528A JP 60168309 A JP60168309 A JP 60168309A JP 16830985 A JP16830985 A JP 16830985A JP S6229528 A JPS6229528 A JP S6229528A
- Authority
- JP
- Japan
- Prior art keywords
- licorice
- extracting
- glycyrrhizin
- organic solvent
- inhibitor
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 claims abstract description 43
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 claims abstract description 41
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 claims abstract description 41
- 229940010454 licorice Drugs 0.000 claims abstract description 41
- 239000004378 Glycyrrhizin Substances 0.000 claims abstract description 23
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims abstract description 23
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229960004949 glycyrrhizic acid Drugs 0.000 claims abstract description 23
- 235000019410 glycyrrhizin Nutrition 0.000 claims abstract description 23
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 22
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 8
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract description 4
- 150000002576 ketones Chemical class 0.000 claims abstract description 4
- 241000202807 Glycyrrhiza Species 0.000 claims abstract 8
- 244000303040 Glycyrrhiza glabra Species 0.000 claims description 35
- 239000002532 enzyme inhibitor Substances 0.000 claims description 17
- 229940125532 enzyme inhibitor Drugs 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 11
- 210000002615 epidermis Anatomy 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 235000017443 Hedysarum boreale Nutrition 0.000 claims description 2
- 235000007858 Hedysarum occidentale Nutrition 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- -1 acetate ethers Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 31
- 230000000694 effects Effects 0.000 abstract description 21
- 238000000605 extraction Methods 0.000 abstract description 20
- 238000002845 discoloration Methods 0.000 abstract description 15
- 102000003425 Tyrosinase Human genes 0.000 abstract description 12
- 108060008724 Tyrosinase Proteins 0.000 abstract description 12
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- 108090000790 Enzymes Proteins 0.000 abstract description 11
- 102000003820 Lipoxygenases Human genes 0.000 abstract description 9
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- 102000003992 Peroxidases Human genes 0.000 abstract description 6
- 108040007629 peroxidase activity proteins Proteins 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 235000013305 food Nutrition 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004365 Protease Substances 0.000 abstract description 4
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 abstract description 3
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- 238000006731 degradation reaction Methods 0.000 abstract 1
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- 239000002904 solvent Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
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- 239000000126 substance Substances 0.000 description 7
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- 238000006243 chemical reaction Methods 0.000 description 6
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- 238000000034 method Methods 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 4
- 108091005508 Acid proteases Proteins 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 102000030523 Catechol oxidase Human genes 0.000 description 4
- 108010031396 Catechol oxidase Proteins 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 108091000117 Tyrosine 3-Monooxygenase Proteins 0.000 description 4
- 102000048218 Tyrosine 3-monooxygenases Human genes 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- 229960002433 cysteine Drugs 0.000 description 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 4
- 235000018417 cysteine Nutrition 0.000 description 4
- 229960001305 cysteine hydrochloride Drugs 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical class OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
- 241000220225 Malus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 102000035195 Peptidases Human genes 0.000 description 3
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 3
- 244000195452 Wasabia japonica Species 0.000 description 3
- 235000000760 Wasabia japonica Nutrition 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
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- 150000002978 peroxides Chemical class 0.000 description 3
- 235000002949 phytic acid Nutrition 0.000 description 3
- 229940068041 phytic acid Drugs 0.000 description 3
- 239000000467 phytic acid Substances 0.000 description 3
- 241000143060 Americamysis bahia Species 0.000 description 2
- 241000238557 Decapoda Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- 241000234295 Musa Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 235000015197 apple juice Nutrition 0.000 description 2
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- 238000004649 discoloration prevention Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000006959 non-competitive inhibition Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 2
- 235000019633 pungent taste Nutrition 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- PHZOWSSBXJXFOR-UHFFFAOYSA-N 2-Propenyl glucosinolate Natural products OCC1OC(SC(CC=C)=NOS(O)(=O)=O)C(O)C(O)C1O PHZOWSSBXJXFOR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 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
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- 244000168667 Pholiota nameko Species 0.000 description 1
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- PHZOWSSBXJXFOR-MYMDCHNCSA-N Sinigrin Natural products S(=O)(=O)(O/N=C(\S[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O1)/CC=C)O PHZOWSSBXJXFOR-MYMDCHNCSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 101710147108 Tyrosinase inhibitor Proteins 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940082991 antihypertensives tyrosine hydroxylase inhibitors Drugs 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
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- MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 description 1
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- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- QKFAFSGJTMHRRY-OCFLFPRFSA-M potassium;[(e)-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylbut-3-enylideneamino] sulfate Chemical group [K+].OC[C@H]1O[C@@H](S\C(CC=C)=N\OS([O-])(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O QKFAFSGJTMHRRY-OCFLFPRFSA-M 0.000 description 1
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- 210000003491 skin Anatomy 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229940001482 sodium sulfite Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60168309A JPS6229528A (ja) | 1985-07-30 | 1985-07-30 | 酵素阻害剤およびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60168309A JPS6229528A (ja) | 1985-07-30 | 1985-07-30 | 酵素阻害剤およびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6229528A true JPS6229528A (ja) | 1987-02-07 |
| JPH057372B2 JPH057372B2 (enrdf_load_stackoverflow) | 1993-01-28 |
Family
ID=15865634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60168309A Granted JPS6229528A (ja) | 1985-07-30 | 1985-07-30 | 酵素阻害剤およびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6229528A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999064025A1 (en) * | 1998-06-08 | 1999-12-16 | Fytokem Products Inc. | Tyrosinase inhibitors from plants |
| CN104277048A (zh) * | 2013-07-10 | 2015-01-14 | 岳普湖天瑞生物工程有限公司 | 一种光果甘草总黄酮的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60214721A (ja) * | 1984-04-06 | 1985-10-28 | Inahata Koryo Kk | シミ防止化粧料組成物 |
| JPS61122209A (ja) * | 1984-11-16 | 1986-06-10 | Osaka Chem Lab | シミ防止化粧料組成物 |
-
1985
- 1985-07-30 JP JP60168309A patent/JPS6229528A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60214721A (ja) * | 1984-04-06 | 1985-10-28 | Inahata Koryo Kk | シミ防止化粧料組成物 |
| JPS61122209A (ja) * | 1984-11-16 | 1986-06-10 | Osaka Chem Lab | シミ防止化粧料組成物 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999064025A1 (en) * | 1998-06-08 | 1999-12-16 | Fytokem Products Inc. | Tyrosinase inhibitors from plants |
| US6521267B1 (en) | 1998-06-08 | 2003-02-18 | Fytokem Prtoducts, Inc. | Tyrosinase inhibitors from plants |
| CN104277048A (zh) * | 2013-07-10 | 2015-01-14 | 岳普湖天瑞生物工程有限公司 | 一种光果甘草总黄酮的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH057372B2 (enrdf_load_stackoverflow) | 1993-01-28 |
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