JP2014105169A - ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 - Google Patents
ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 Download PDFInfo
- Publication number
- JP2014105169A JP2014105169A JP2012257995A JP2012257995A JP2014105169A JP 2014105169 A JP2014105169 A JP 2014105169A JP 2012257995 A JP2012257995 A JP 2012257995A JP 2012257995 A JP2012257995 A JP 2012257995A JP 2014105169 A JP2014105169 A JP 2014105169A
- Authority
- JP
- Japan
- Prior art keywords
- stevia
- diterpene compound
- yeast
- compound
- solvent
- 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
- -1 Diterpene compound Chemical class 0.000 title claims abstract description 49
- 229930004069 diterpene Natural products 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title abstract description 8
- 239000007854 depigmenting agent Substances 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 claims description 38
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 34
- 230000002087 whitening effect Effects 0.000 claims description 25
- 241000544066 Stevia Species 0.000 claims description 20
- 239000000419 plant extract Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 abstract description 12
- 206010040829 Skin discolouration Diseases 0.000 abstract 1
- 244000228451 Stevia rebaudiana Species 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- 230000008099 melanin synthesis Effects 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 18
- 238000000855 fermentation Methods 0.000 description 17
- 230000004151 fermentation Effects 0.000 description 17
- 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 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 235000019202 steviosides Nutrition 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 239000004383 Steviol glycoside Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 235000019411 steviol glycoside Nutrition 0.000 description 7
- 229930182488 steviol glycoside Natural products 0.000 description 7
- 150000008144 steviol glycosides Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 102000003425 Tyrosinase Human genes 0.000 description 6
- 108060008724 Tyrosinase Proteins 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 239000000469 ethanolic extract Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 239000012156 elution solvent Substances 0.000 description 5
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 5
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 5
- 229960004705 kojic acid Drugs 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XRYVAQQLDYTHCL-IQMFZBJNSA-N Sophoraflavanone G Natural products C1([C@H]2CC(=O)C=3C(O)=CC(O)=C(C=3O2)C[C@@H](CC=C(C)C)C(C)=C)=CC=C(O)C=C1O XRYVAQQLDYTHCL-IQMFZBJNSA-N 0.000 description 3
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- BZXULYMZYPRZOG-UHFFFAOYSA-N centaureidin Chemical compound C1=C(O)C(OC)=CC=C1C1=C(OC)C(=O)C2=C(O)C(OC)=C(O)C=C2O1 BZXULYMZYPRZOG-UHFFFAOYSA-N 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XRYVAQQLDYTHCL-CMJOXMDJSA-N sophoraflavanone G Chemical compound C1([C@@H]2CC(=O)C=3C(O)=CC(O)=C(C=3O2)C[C@@H](CC=C(C)C)C(C)=C)=CC=C(O)C=C1O XRYVAQQLDYTHCL-CMJOXMDJSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 description 2
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 description 2
- 229920002079 Ellagic acid Polymers 0.000 description 2
- 239000001512 FEMA 4601 Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 description 2
- 241000235070 Saccharomyces Species 0.000 description 2
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000004132 ellagic acid Nutrition 0.000 description 2
- 229960002852 ellagic acid Drugs 0.000 description 2
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 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 2
- 229930182470 glycoside Natural products 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000019203 rebaudioside A Nutrition 0.000 description 2
- QSRAJVGDWKFOGU-WBXIDTKBSA-N rebaudioside c Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 description 2
- 229940013618 stevioside Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- OSJPPGNTCRNQQC-UHFFFAOYSA-N 3-phosphoglyceric acid Chemical compound OC(=O)C(O)COP(O)(O)=O OSJPPGNTCRNQQC-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000007754 Achillea millefolium Nutrition 0.000 description 1
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000005956 Cosmos caudatus Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 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
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 206010014970 Ephelides Diseases 0.000 description 1
- 208000001382 Experimental Melanoma Diseases 0.000 description 1
- 239000001776 FEMA 4720 Substances 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- DHCLVCXQIBBOPH-UHFFFAOYSA-N Glycerol 2-phosphate Chemical compound OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-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
- 150000000996 L-ascorbic acids Chemical class 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
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 244000294411 Mirabilis expansa Species 0.000 description 1
- 235000015429 Mirabilis expansa Nutrition 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 description 1
- 229940099408 Oxidizing agent Drugs 0.000 description 1
- 208000012641 Pigmentation disease Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 244000134540 Polymnia sonchifolia Species 0.000 description 1
- 235000003406 Polymnia sonchifolia Nutrition 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VJNCICVKUHKIIV-UHFFFAOYSA-N dopachrome Chemical compound O=C1C(=O)C=C2NC(C(=O)O)CC2=C1 VJNCICVKUHKIIV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000021107 fermented food Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- CCCXGQLQJHWTLZ-UHFFFAOYSA-N geranyl linalool Natural products CC(=CCCC(=CCCCC(C)(O)CCC=C(C)C)C)C CCCXGQLQJHWTLZ-UHFFFAOYSA-N 0.000 description 1
- IQDXAJNQKSIPGB-HQSZAHFGSA-N geranyllinalool Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)(O)C=C IQDXAJNQKSIPGB-HQSZAHFGSA-N 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- IGGVVGHJSQSLFO-UHFFFAOYSA-N indole-5,6-quinone Chemical compound O=C1C(=O)C=C2C=CNC2=C1 IGGVVGHJSQSLFO-UHFFFAOYSA-N 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000021109 kimchi Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 210000002752 melanocyte Anatomy 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000013536 miso Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000019992 sake Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- DGPIGKCOQYBCJH-UHFFFAOYSA-M sodium;acetic acid;hydroxide Chemical compound O.[Na+].CC([O-])=O DGPIGKCOQYBCJH-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Images
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyrane Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
当該ジテルペン化合物の抽出溶剤としては、極性溶剤、非極性溶剤のいずれを使用することもでき、これらを混合して使用することもできる。抽出溶剤としては、水のほか、メタノール、エタノール、プロパノール、ブタノールなどの炭素数1〜12の分岐を有していても良いアルコール類、エチレングリコール、プロピレングリコール、ブチレングリコールなどの多価アルコール類、アセトン、メチルエチルケトンなどのケトン類、酢酸メチル、酢酸エチルなどのエステル類、テトラヒドロフラン、ジエチルエーテルなどのエーテル類、ポリエチレングリコールなどのポリエーテル類、ジクロロメタン、クロロホルム、四塩化炭素などのハロゲン化炭素類、ヘキサン、シクロヘキサン、石油エーテルなどの炭化水素類、ベンゼン、トルエンなどの芳香族炭化水素類、ピリジン類、超臨界二酸化炭素、油脂、ワックスその他のオイル類がある。これらは単独でも組み合わせて用いてもよい。
本発明では、アルコールを使用することが好ましい。アルコールとしては、炭素数1〜5の一価アルコールが好適である。この中でも、特に好ましくはエタノールである。アルコールは、水を含む含水アルコールであってもよい。含水アルコールを使用する場合のアルコール濃度は、30〜99(v/v)%であることが好ましく、より好ましくは50〜90(v/v)%である。アルコールまたは含水アルコールによる抽出は、上記ステビア酵母発酵物1質量部(乾燥重量)に対して0.1〜100質量部、好ましくは1〜50質量部の溶剤を添加し、温度5〜35℃で3〜30日間の浸漬が好適である。
(実施例1)
日本国北海道産のステビア植物(学名:Stevia rebaudiana)の茎と葉とを乾燥させた乾燥ステビア植物を約1cm以下に粉砕した。粉砕ステビア植物2,000gに酵母菌(Saccharomyces)45g、水4,500gを加えて温度25〜35℃の条件下に撹拌すると、発酵が開始した。これを温度25〜35℃にて14日間静置、発酵させた。発酵物から甘味が消失しており、これを発酵終期とした。上記の発酵物を温度25〜35℃にて10日間乾燥させ、酵母発酵を停止した。
10質量倍量の28.5(v/v)%エタノールに前記乾燥発酵物の全量を加え、穏やかに攪拌しながら数日、常温にて浸潤させた。浸潤後、140メッシュ程度の大きさでろ過した。得られたろ液を60℃ほどで減圧濃縮(60mmHg)し、ダイヤイオンHP20カラムに吸着させた後に85.5%含水エタノール液で溶出し、これを含水エタノール抽出液とした。
上記含水エタノール抽出液の溶媒を留去した抽出物(60g)にクロロホルム1000mLを加え、温度23〜28℃(室温)で抽出した。残渣をろ過により除き、クロロホルム層を分取し、溶媒を留去したものをクロロホルム抽出液(28.8g)とした。
上記(3)で得たクロロホルム抽出液(28.8g)を、下記分離条件(1)に示すシリカゲルカラムクロマトグラフィーより7つの画分に分離した。
分離条件(1):
カラム: 内径7cm、高さ22cm
充填物: シリカゲル(KANTO CHEMICAL社製、Silica Gel 60N(球状,中性)、粒子径63〜210μm)、320g、
溶出溶媒: クロロホルム:メタノール=100:1→50:1→30:1→15:1→7:1→5:1→0:1の混合溶液を溶離液とし、順次カラムに各溶媒1000mLずつ流し、200mLずつ分取した。
分取物: 上記溶出溶媒毎にa〜gの7つの画分に分画した。各画分の収量を図1に示す。
分離条件(2):
カラム: 内径5.2cm、高さ20cm
充填物: シリカゲル(KANTO CHEMICAL社製、Silica Gel 60N(球状,中性)、粒子径63〜210μm)、160g、
溶出溶媒: クロロホルム:メタノール=100:1→50:1→20:1→10:1→5:1→2:1→0:1の混合溶液を溶離液とし、順次カラムに各溶媒700mLずつ流し、150mLずつ分取した。
分取物: 上記溶出溶媒毎にd−1〜d−8の8つの画分に分画した。各画分の収量を図1に示す。
分離条件(3):
カラム: 内径4.2cm、高さ20cm
充填物: シリカゲル(KANTO CHEMICAL社製、Silica Gel 60N(球状,中性)、粒子径63〜210μm)、90g、
溶出溶媒: n−ヘキサン:アセトン=7:1→3:1→1:1→1:2→0:1の混合溶液を溶離液とし、順次カラムに各溶媒700mLずつ流し、70mLずつ分取した。
分取物: 各画分の収量を図1に示す。各画分についてTLC(MERCK Silica Gel 60 F254)を行った。n−ヘキサン:アセトン=1:1の溶媒で展開後、50%硫酸を噴霧し、110℃で加熱して検出した。d−4−7画分が、シングルスポットとして検出された。この画分の溶媒を除去すると白色粉末が得られた。この化合物を化合物VIIIとした。
前記白色粉末について、1H−NMRおよび13C−NMRを測定した。結果を表1に示す。1H−NMRおよび13C−NMRのシグナルパターンより、炭素数20であり、すでにステビアより単離報告のあるステレビンAとA環、B環は同じ構造を有すると推定されるが、C環以降の構造が異なっていると推定された。そこで、HMQCとHMBCの相関を詳細に検討したところ、表1に示すHMBC相関が認められ、最終的に、下記式(VIII)に示されるジテルペン化合物と決定した。表1の下部に当該化合物の基本骨格と位置番号とを示す。
実施例1で得た化合物について、下記測定方法に従って、細胞数当たりのメラニン産生量および対照に対するメラニン産生率の算出方法に従って、B16メラノーマ細胞生存数を計測し、溶液当たりのメラニン産生量を測定し、これにより生細胞当たりのメラニン産生量(ng/104cells)を算出した。また、対照の生細胞当たりのメラニン産生量(ng/104cells)に対する式(VIII)の化合物によるメラニン濃度を算出した。結果を表2に示す。なお、化合物の濃度は100μMとし、比較のため1000μMのコウジ酸も同様に処理した。
細胞数当たりのメラニン産生量および対照に対するメラニン産生率の算出方法は、以下に従った。
6ウェルプレートで一晩培養を行ったB16マウスメラノーマ細胞の培地を除去し、各ウェルにテオフィリン(最終濃度として10mM)、目的濃度のサンプルを加えた10%−FBS−DMEM培地(サンプル溶解のためのDMSOの最終濃度は0.1%)を2mLずつ加えた。
37℃、5%CO2存在下で72時間培養した後、培地を除去し、pH7.4等張リン酸緩衝液(PBS)で細胞を2回リンスした。各ウェルに0.25%トリプシン−EDTA溶液を200μlずつ加えてトリプシン処理をし、培地を1mlずつ添加して全量を15ml遠沈管に回収した。細胞液を1000rpm、5分間遠心分離し、上清を除去した細胞にPBSを2ml加えて再懸濁させ、このうち200μlをマイクロチューブに移し、セルカウンター(ミリポアコーポレーション製、Sceptor(登録商標))を用いて細胞数を計測した。残りの細胞液を再び同条件で遠心分離し上清を取り除き、1MのNaOHを1ml添加して80℃の水浴で1時間処理した。細胞融解液の濃度の吸光度をImmuno Mini NJ−2300(コスモバイオコーポレーション製)を用いて波長475nmにて測定し、細胞数あたりのメラニン産生量を算出した。検量線には1M NaOHに融解した合成メラニン(シグマアルドリッチコーポレーション製)を用いた。データは対照(1mMテオフィリン添加培地適用)群の値を100%とした細胞数あたりのメラニン産生率及び生細胞数率で表し、それぞれn=3の平均値±標準偏差にて表した。また、統計学的解析には分散分析(ANOVA)及び多重比較検定(Dunnet法)を用いた。
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012257995A JP5933419B2 (ja) | 2012-11-26 | 2012-11-26 | ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012257995A JP5933419B2 (ja) | 2012-11-26 | 2012-11-26 | ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014105169A true JP2014105169A (ja) | 2014-06-09 |
JP5933419B2 JP5933419B2 (ja) | 2016-06-08 |
Family
ID=51026965
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012257995A Active JP5933419B2 (ja) | 2012-11-26 | 2012-11-26 | ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5933419B2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014105170A (ja) * | 2012-11-26 | 2014-06-09 | Shalom:Kk | 新規化合物、美白剤および前記化合物の製造方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61180782A (ja) * | 1985-01-26 | 1986-08-13 | ヘキスト・アクチエンゲゼルシヤフト | フオースクリン、その類似体および誘導体 |
JPH0672855A (ja) * | 1992-07-08 | 1994-03-15 | Pola Chem Ind Inc | メラニン産生抑制剤及び皮膚外用剤 |
JP2005263775A (ja) * | 2004-02-19 | 2005-09-29 | Soda Aromatic Co Ltd | メラニン生成抑制剤 |
JP2006137705A (ja) * | 2004-11-12 | 2006-06-01 | Pola Chem Ind Inc | メラニン産生抑制剤及び皮膚外用剤 |
JP2007254393A (ja) * | 2006-03-23 | 2007-10-04 | Showa Denko Kk | 皮膚外用剤 |
WO2014080666A1 (ja) * | 2012-11-26 | 2014-05-30 | 株式会社シャローム | ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 |
JP2014105170A (ja) * | 2012-11-26 | 2014-06-09 | Shalom:Kk | 新規化合物、美白剤および前記化合物の製造方法 |
-
2012
- 2012-11-26 JP JP2012257995A patent/JP5933419B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61180782A (ja) * | 1985-01-26 | 1986-08-13 | ヘキスト・アクチエンゲゼルシヤフト | フオースクリン、その類似体および誘導体 |
JPH0672855A (ja) * | 1992-07-08 | 1994-03-15 | Pola Chem Ind Inc | メラニン産生抑制剤及び皮膚外用剤 |
JP2005263775A (ja) * | 2004-02-19 | 2005-09-29 | Soda Aromatic Co Ltd | メラニン生成抑制剤 |
JP2006137705A (ja) * | 2004-11-12 | 2006-06-01 | Pola Chem Ind Inc | メラニン産生抑制剤及び皮膚外用剤 |
JP2007254393A (ja) * | 2006-03-23 | 2007-10-04 | Showa Denko Kk | 皮膚外用剤 |
WO2014080666A1 (ja) * | 2012-11-26 | 2014-05-30 | 株式会社シャローム | ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 |
JP2014105170A (ja) * | 2012-11-26 | 2014-06-09 | Shalom:Kk | 新規化合物、美白剤および前記化合物の製造方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014105170A (ja) * | 2012-11-26 | 2014-06-09 | Shalom:Kk | 新規化合物、美白剤および前記化合物の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
JP5933419B2 (ja) | 2016-06-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101916977B1 (ko) | 칼콘 또는 디히드로칼콘의 모노테르펜 유도체 및 미백제제로서의 용도 | |
JP5933748B2 (ja) | ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 | |
KR102239784B1 (ko) | 엉겅퀴 및 모링가의 온천수 발효 추출물의 혼합물을 포함하는 화장료 조성물 | |
KR101283849B1 (ko) | 신규한 미백용 및 항산화 화장료 조성물 | |
KR20200048158A (ko) | 들깨박 추출물을 유효성분으로 포함하는 항산화 또는 피부 주름 개선용 조성물 | |
KR101289813B1 (ko) | 회화나무꽃 추출물을 유효성분으로 포함하는 피부 주름 개선용 조성물 | |
JP5933419B2 (ja) | ジテルペン化合物、美白剤およびジテルペン化合物の製造方法 | |
JP5149548B2 (ja) | Thymelaea属植物からの抽出物を有効成分とするメラニン産生抑制剤、及びこれを含有する美白用の医薬品組成物、並びに化粧料組成物 | |
KR102077069B1 (ko) | 갯끈풀 추출물을 유효성분으로 함유하는 항산화 또는 피부 미백 개선용 조성물 | |
JP5154835B2 (ja) | 美白化粧料 | |
KR101050484B1 (ko) | 락톤계 화합물을 유효성분으로 함유하는 피부 미백용 조성물 | |
JP5275075B2 (ja) | (2z,8z)―メトリカリア酸メチルエステルを有効成分として含む皮膚美白用組成物 | |
JP5943833B2 (ja) | 新規化合物、美白剤および前記化合物の製造方法 | |
JP5933420B2 (ja) | 新規化合物、美白剤および前記化合物の製造方法 | |
JP6013180B2 (ja) | 美白剤 | |
KR20080060380A (ko) | 브로콜리 추출물을 유효성분으로 함유하는 피부노화 방지용화장료 조성물 | |
KR101069906B1 (ko) | 비짜루국화 추출물을 함유하는 피부 상태개선용 조성물 | |
JP2020045355A (ja) | ムレスズメ根抽出物を含有する美白用化粧料組成物 | |
KR101068808B1 (ko) | 봉황목 추출물을 유효성분으로 함유하는 미백용 조성물 | |
KR101221711B1 (ko) | 비쭈기나무 추출물을 유효성분으로 함유하는 화장료 조성물 | |
KR102014646B1 (ko) | 골담초 유래 화합물 및 이를 함유하는 피부 미백용 조성물 | |
KR20100043717A (ko) | 익소라 콕시니아 추출물을 유효성분으로 함유하는 미백용 조성물 | |
KR20140121627A (ko) | 헤스페레틴을 이용한 피부 미백용 조성물 | |
KR20220153349A (ko) | 갈대 뿌리의 황국균 발효 추출물 제조방법 | |
KR20140121626A (ko) | 온주 밀감 꽃 추출물을 이용한 피부 미백용 조성물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150908 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160412 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160414 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160502 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5933419 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |