JPH057372B2 - - Google Patents
Info
- Publication number
- JPH057372B2 JPH057372B2 JP60168309A JP16830985A JPH057372B2 JP H057372 B2 JPH057372 B2 JP H057372B2 JP 60168309 A JP60168309 A JP 60168309A JP 16830985 A JP16830985 A JP 16830985A JP H057372 B2 JPH057372 B2 JP H057372B2
- Authority
- JP
- Japan
- Prior art keywords
- licorice
- quality deterioration
- organic solvent
- extract
- food quality
- 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.)
- Expired - Lifetime
Links
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 claims description 54
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 claims description 50
- 244000303040 Glycyrrhiza glabra Species 0.000 claims description 50
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 claims description 50
- 229940010454 licorice Drugs 0.000 claims description 50
- 230000006866 deterioration Effects 0.000 claims description 49
- 239000003112 inhibitor Substances 0.000 claims description 47
- 235000013305 food Nutrition 0.000 claims description 42
- 239000003960 organic solvent Substances 0.000 claims description 30
- 239000000284 extract Substances 0.000 claims description 26
- 239000004378 Glycyrrhizin Substances 0.000 claims 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 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 description 23
- 229960004949 glycyrrhizic acid Drugs 0.000 claims description 23
- 235000019410 glycyrrhizin Nutrition 0.000 claims 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 description 23
- 238000000605 extraction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 210000002615 epidermis Anatomy 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 235000017443 Hedysarum boreale Nutrition 0.000 claims description 4
- 235000007858 Hedysarum occidentale Nutrition 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 230000003449 preventive effect Effects 0.000 claims description 2
- 241000202807 Glycyrrhiza Species 0.000 claims 4
- 235000019439 ethyl acetate Nutrition 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 102000003425 Tyrosinase Human genes 0.000 description 23
- 108060008724 Tyrosinase Proteins 0.000 description 23
- 230000000694 effects Effects 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 230000002401 inhibitory effect Effects 0.000 description 19
- 239000000523 sample Substances 0.000 description 18
- 238000002845 discoloration Methods 0.000 description 16
- 102000004190 Enzymes Human genes 0.000 description 14
- 108090000790 Enzymes Proteins 0.000 description 14
- 229940088598 enzyme Drugs 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 102000003820 Lipoxygenases Human genes 0.000 description 10
- 108090000128 Lipoxygenases Proteins 0.000 description 10
- 239000002027 dichloromethane extract Substances 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 102000030523 Catechol oxidase Human genes 0.000 description 8
- 108010031396 Catechol oxidase Proteins 0.000 description 8
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 8
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- 240000008790 Musa x paradisiaca Species 0.000 description 7
- 108091005804 Peptidases Proteins 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000002904 solvent Substances 0.000 description 6
- 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 5
- 102000003992 Peroxidases Human genes 0.000 description 5
- 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 5
- 239000004365 Protease Substances 0.000 description 5
- 229960002433 cysteine Drugs 0.000 description 5
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 5
- 235000018417 cysteine Nutrition 0.000 description 5
- 239000000469 ethanolic extract Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000009246 food effect Effects 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 108040007629 peroxidase activity proteins Proteins 0.000 description 5
- 235000002949 phytic acid Nutrition 0.000 description 5
- 229940068041 phytic acid Drugs 0.000 description 5
- 239000000467 phytic acid Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 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
- 241000238557 Decapoda Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 102000035195 Peptidases Human genes 0.000 description 4
- 244000195452 Wasabia japonica Species 0.000 description 4
- 235000000760 Wasabia japonica Nutrition 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
- 235000013399 edible fruits Nutrition 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
- 238000000926 separation method Methods 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 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 3
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 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
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000021016 apples Nutrition 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 229960001305 cysteine hydrochloride Drugs 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- 108091005508 Acid proteases Proteins 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- 241000234295 Musa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 101710147108 Tyrosinase inhibitor Proteins 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 235000015197 apple juice Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004649 discoloration prevention Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- -1 hexane and n-pentane Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052751 metal Chemical class 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- 229930014626 natural product Natural products 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
- 150000002989 phenols Chemical class 0.000 description 2
- 235000004252 protein component Nutrition 0.000 description 2
- 235000019633 pungent taste Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 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
- 244000168667 Pholiota nameko Species 0.000 description 1
- 235000014528 Pholiota nameko Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- 230000008901 benefit Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- FODTZLFLDFKIQH-FSVGXZBPSA-N gamma-Oryzanol (TN) Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)O[C@@H]2C([C@@H]3CC[C@H]4[C@]5(C)CC[C@@H]([C@@]5(C)CC[C@@]54C[C@@]53CC2)[C@H](C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-FSVGXZBPSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 229940069445 licorice extract Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 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
- 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
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017291 sinigrin Nutrition 0.000 description 1
- 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
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000003809 water extraction Methods 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 JPS6229528A (ja) | 1987-02-07 |
| JPH057372B2 true JPH057372B2 (no) | 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 (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999064025A1 (en) * | 1998-06-08 | 1999-12-16 | Fytokem Products Inc. | Tyrosinase inhibitors from plants |
| CN104277048B (zh) * | 2013-07-10 | 2016-09-21 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6229528A (ja) | 1987-02-07 |
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