CN106397169A - Filicinic acid compounds, and pharmaceutical compositions and application thereof - Google Patents
Filicinic acid compounds, and pharmaceutical compositions and application thereof Download PDFInfo
- Publication number
- CN106397169A CN106397169A CN201610255364.3A CN201610255364A CN106397169A CN 106397169 A CN106397169 A CN 106397169A CN 201610255364 A CN201610255364 A CN 201610255364A CN 106397169 A CN106397169 A CN 106397169A
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- China
- Prior art keywords
- acid
- rxj
- filicinic
- skin
- class compound
- Prior art date
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- ZITLVRQXJUFZOO-UHFFFAOYSA-N filicinic acid Chemical class CC1(C)C(O)=CC(=O)C=C1O ZITLVRQXJUFZOO-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- -1 Rxj-33 (1) Chemical class 0.000 claims abstract description 12
- 239000003937 drug carrier Substances 0.000 claims abstract description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 28
- 239000002537 cosmetic Substances 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 13
- 241000894006 Bacteria Species 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 244000219416 Hypericum japonicum Species 0.000 claims description 9
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 9
- 238000010898 silica gel chromatography Methods 0.000 claims description 9
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 8
- 241000191967 Staphylococcus aureus Species 0.000 claims description 8
- 208000037386 Typhoid Diseases 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 238000010828 elution Methods 0.000 claims description 8
- 239000000284 extract Substances 0.000 claims description 8
- 201000008297 typhoid fever Diseases 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 claims description 6
- 241000588724 Escherichia coli Species 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 208000034801 Enterobacteriaceae Infections Diseases 0.000 claims description 4
- 206010015150 Erythema Diseases 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 206010027146 Melanoderma Diseases 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- 230000037307 sensitive skin Effects 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 230000037303 wrinkles Effects 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 238000002791 soaking Methods 0.000 claims description 3
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 229960000250 adipic acid Drugs 0.000 claims description 2
- 239000000783 alginic acid Substances 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 229960001126 alginic acid Drugs 0.000 claims description 2
- 150000004781 alginic acids Chemical class 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- 230000000721 bacterilogical effect Effects 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- AWUCVROLDVIAJX-UHFFFAOYSA-N glycerol 1-phosphate Chemical compound OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 229960000448 lactic acid Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229940098895 maleic acid Drugs 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 229920003175 pectinic acid Polymers 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229960005137 succinic acid Drugs 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 2
- KWMLJOLKUYYJFJ-UHFFFAOYSA-N 2,3,4,5,6,7-Hexahydroxyheptanoic acid Chemical compound OCC(O)C(O)C(O)C(O)C(O)C(O)=O KWMLJOLKUYYJFJ-UHFFFAOYSA-N 0.000 claims 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims 1
- 235000005979 Citrus limon Nutrition 0.000 claims 1
- 244000248349 Citrus limon Species 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 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 claims 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 claims 1
- OASRDXXKKGHDJZ-UHFFFAOYSA-N octadec-17-en-9,11-diynoic acid Chemical compound OC(=O)CCCCCCCC#CC#CCCCCC=C OASRDXXKKGHDJZ-UHFFFAOYSA-N 0.000 claims 1
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- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical class OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 abstract description 2
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 abstract 1
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- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 206010023126 Jaundice Diseases 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
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-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
- 239000004909 Moisturizer Substances 0.000 description 1
- 241000287127 Passeridae Species 0.000 description 1
- 208000009675 Perioral Dermatitis Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 0.000 description 1
- 206010061926 Purulence Diseases 0.000 description 1
- 241001303601 Rosacea Species 0.000 description 1
- DLHDQCUNWHXCBT-UHFFFAOYSA-N Sarothralin A Natural products CC(C)C(=O)C1=C(O)C(C)(C)C(=C(Cc2c(O)c(CC=C(/C)CCC=C(C)C)c(O)c(C(=O)C(C)C)c2O)C1=O)O DLHDQCUNWHXCBT-UHFFFAOYSA-N 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- 206010039796 Seborrhoeic keratosis Diseases 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 206010041955 Stasis dermatitis Diseases 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 1
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 1
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000004500 asepsis Methods 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012930 cell culture fluid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 1
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 208000004000 erythrasma Diseases 0.000 description 1
- 208000004526 exfoliative dermatitis Diseases 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 208000001786 gonorrhea Diseases 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000000990 heteronuclear single quantum coherence spectrum Methods 0.000 description 1
- 230000001524 infective effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 201000003385 seborrheic keratosis Diseases 0.000 description 1
- 231100000075 skin burn Toxicity 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- 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
- A61Q19/005—Preparations for sensitive skin
-
- 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
- A61Q19/007—Preparations for dry skin
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
The invention provides filicinic acid compounds of Rxj-33 (1), Rxj-43 (2), Rxj-18 (3) and Rxj-19 (4) or pharmaceutical salts thereof, pharmaceutical compositions composed of the filicinic acid compounds as effective components and at least one pharmaceutically-acceptable carrier, a preparation method for the filicinic acid compounds, and applications of the filicinic acid compounds in preparation of antibacterial drugs. The compounds namely Rxj-33 (1), Rxj-43 (2), Rxj-18 (3) and Rxj-19 (4) are novel filicinic acid (dimeric phloroglucinol derivative) compounds, and have significant activity on in-vitro inhibition of bacterial growth, novel chemical structure and a plurality of advantages as the antimicrobial drugs.
Description
Technical field：
The invention belongs to technical field of pharmaceuticals, specifically, it is related to the filicinic acid class compound with bacteriostatic activity
Rxj-33 (1), Rxj-43 (2), Rxj-18 (3), Rxj-19 (4) and preparation method thereof, the food with this compound as active component
Product, cosmetics, pharmaceutical composition, and it is in the cosmetics preparing the skin problem that prevention and treatment bacterium infection leads to and medicine
Application in thing.
Background technology：
Hypericum (Hypericum) is a big genus of Guttiferae (Guttiferae), and about 400 kinds of the whole world, except south
Northern two polar regions or desert ground and the outer world of most of torrid zone low land blazon.China there are about 55 kind of 8 subspecies, several originate in all parts of the country,
But it is concentrated mainly on southwest.Except being used for viewing and admiring, hypericum has antidepression, antiviral, antibacterial and antitumor
Etc. multiple pharmacologically actives.
Hypericum japonicum (Hypericum japonicum Thunb.)：《Dictionary of medicinal plant》Record kind, another name hypericum japonicum, sparrow
Tongue grass.Annual herb, originates in the ground such as Jiangsu, Zhejiang, Sichuan, Yunnan.There is the effects such as clearing heat and promoting diuresis, subdhing swelling and detoxicating, be used for
Jaundice heat gonorrhea, pyogenic infections, venomous snake bite.The chemical composition of this plant of document report has flavones, xanthone etc..In prior art not
See there is separating obtained filicinic acid class compound from hypericum japonicum involved in the present invention, and their pharmaceutically active function
Report.
Content of the invention：
Present invention aim at provide separating, from hypericum japonicum (H.japonicum), the filicinic acid class compound obtaining,
Food with it as active component, cosmetics or pharmaceutical composition, its preparation method, and its in preparation prevention and treatment bacterium sense
Application in the medicine of dye disease, and the application in the cosmetics of the skin problem that preparation prevention bacterium infection leads to, energy
For preventing microgroove and/wrinkle, skin erythema, dryness, sensitive skin, pruitus, colour of skin inequality or skin blackspot, skin is sent out
Scorching and other skin uncomfortable diseases related to this.
In order to realize the above-mentioned purpose of the present invention, the invention provides following technical scheme：
Filicinic acid class compound R xj-33 (1) shown in following structural formula, Rxj-43 (2), Rxj-18 (3), Rxj-19
(4) or its pharmaceutical salts,
Filicinic acid class compound R xj-33 (1), Rxj-43 (2), Rxj-18 (3), Rxj-19 (4) or its medicine as mentioned
With salt, described pharmaceutical salts are to refer to pharmaceutically acceptable salt, are the salt being formed with organic acid, and described organic acid is winestone
Acid, formic acid, acetic acid, ethanedioic acid, butyric acid, maleic acid, butanedioic acid, adipic acid, alginic acid, citric acid, aspartic acid, benzene sulfonic acid, camphor tree
Olic acid, camphorsulfonic acid, didextrose acid, pentamethylene propionic acid, dodecyl sulphate, ethyl sulfonic acid, glucoheptonic acid, phosphoglycerol, enanthic acid,
Caproic acid, fumaric acid, 2 ethylenehydrinsulfonic acids, lactic acid, methanesulfonic acid, nicotinic acid, 2 naphthalene sulfonic acids, flutter acid, pectinic acid, 3 phenyl third
Acid, neopentanoic acid, propionic acid, p-methyl benzenesulfonic acid and hendecanoic acid.
Cosmetics, by described filicinic acid class compound 1-4 any one or appoint several mixtures and cosmetics to commonly use
Carrier forms.
Filicinic acid class compound 1-4 containing therapeutically effective amount any one or appoint several mixtures or its pharmaceutical salts and
The pharmaceutical composition of pharmaceutically acceptable carrier.
Described filicinic acid class compound 1-4 any one or appoint several mixtures in preparing cosmetics or food
Application.
Described filicinic acid class compound 1-4 any one or appoint several mixtures preparing pre- bacteriological protection large intestine bar
Application in the cosmetics of skin uncomfortable diseases that bacterium, typhoid bacillus, staphylococcus aureus, excrement Enterobacteriaceae infections lead to.
Described filicinic acid class compound 1-4 any one or appoint several mixtures in preparation prevention skin uncomfortable diseases
Application in cosmetics, described skin uncomfortable diseases are microgroove and/wrinkle, skin erythema, dryness, sensitive skin, pruitus,
Colour of skin inequality or skin blackspot, chafing.
Described filicinic acid class compound 1-4 any one or appoint several mixtures or its pharmaceutical salts in preparation prevention or
Treat the application in the medicine of disease being led to by bacterium infection, described disease is by Escherichia coli, typhoid bacillus, golden yellow
The disease that staphylococcus, excrement Enterobacteriaceae infections are led to.
The method of the filicinic acid class compound 1-4 described in preparation claim 1, takes hypericum japonicum that herb is dried, and pulverizes, and uses
Cold soaking 2 times under methyl alcohol room temperature, 24 hours every time, merge extract, vacuum distillation concentrates, and obtains medicinal extract, medicinal extract 100-200 mesh silicon
Glue mixes sample, silica gel column chromatography, affords chloroform section with chloroform, and sample mixed by the chloroform section polyamide of 1.5 times amount, crosses MCI post, with
7:3-10:0 MeOH-H2O carries out gradient elution, obtains 5 big sections A-E, B section through silica gel column chromatography, with 1:0-0:1 oil
Ether-acetone carries out gradient elution, obtains 4 segment B1-B4, wherein B3 section through preparing HPLC, methanol-water, 95:5 isolate and purify
After obtain Rxj-33；Equally, B4 part through prepare HPLC, methanol-water, 95:5 isolate and purify after obtain Rxj-18 and Rxj-19；C
Section 100-200 mesh silica gel mixed sample, silica gel column chromatography, with 1:0-0:1 petroleum ether-acetone carries out gradient elution, obtains 5 portions
Point C1-C5, wherein C2 part through preparing HPLC, methanol-water, 95:5 isolate and purify after obtain Rxj-43.
The compound 1-4 of the present invention is new filicinic acid class (dimerization phloroglucin analog derivative) compound, chemistry knot
Structure is novel, has more advantage as antibacterials.Compound 1-4 has the activity of significantly external bacteria growing inhibiting, to big
Enterobacteria, typhoid bacillus, staphylococcus aureus, excrement enterobacteria have significant inhibitory action.Especially compound 1-4 is to wound
Cold bacillus inhibition concentration is less than positive control CTX (cefotaxime), and compound 1 and 3 pairs of staphylococcus aureuses
Inhibition concentration also below positive control.These compounds can be used for preparation as active component and prevent dermopathic cosmetics,
Or as antibacterial medicine preparation, there is preferable medical value.
In the present invention, the composition containing compound and cosmetics common carrier can be used for topical skin care or hair care
Product.These compositions can make emulsifying agent (such as oil-in-water, Water-In-Oil, silicon Water-In-Oil, water bag silicone oil, W/O/W,
Water-In-Oil bag oil, Water-In-Oil bag silicone oil etc.), creme, shin moisturizer, liquid (such as aqua or water-alcohol solution), anhydrous substrate (example
As lipstick or pulvis etc.), curry, ointment, milk, ointment, spray, solid formulation, eye cream etc..These compositions of local application can
Treatment Dry, sensitive skin or skin itching or the outward appearance reducing colour of skin inequality.Skin disease includes Dry, skin is scratched
Itch, chafing, erythema, allergic, pruritus, Aranea blood vessel, freckle, senile plaque expelling, senile purpura, seborrheic keratosis, blackspot
Disease, pimple, microgroove or wrinkle, tubercle, skin sun-damaged, dermatitis are (seborrhea, nummular dermatitis, contact dermatitis, different
Position property dermatitis, exfoliative dermatitis, Perioral Dermatitis and stasis dermatitis etc.), psoriasis, folliculitis, rosacea, acne, purulence born of the same parents
Disease, erysipelas, erythrasma, eczema, sun burn, skin burn, open wound, infective factors etc..Skin disease also can be by sudden and violent
Dew under ultraviolet light, the age, radiate, be chronically exposed under the sun, environmental pollution, air pollution, wind, hot and cold, chemicals, disease
Reason, smoking or shortage nutrition etc. cause.
Brief description：
Fig. 1 is the compounds of this invention Rxj-33 (1), Rxj-43 (2), Rxj-18 (3), the configuration diagram of Rxj-19 (4).
Specific embodiment：
Below in conjunction with the accompanying drawings, further illustrate the essentiality content of the present invention with embodiments of the invention, but not with
This is limiting the present invention.
Embodiment 1：
Compound R xj-33 (1), Rxj-43 (2), Rxj-18 (3), the preparation of Rxj-19 (4)：
Take hypericum japonicum that herb (14kg) is dried, pulverize, with cold soaking 2 times under methyl alcohol room temperature, 24 hours every time, merge and extract
Liquid, vacuum distillation concentrates, and obtains medicinal extract 2.5kg.Crude extract 100-200 mesh silica gel mixed sample, silica gel column chromatography, eluted with chloroform
To chloroform section (164.2g).Sample mixed by the chloroform section polyamide of 1.5 times amount, crosses MCI post, with MeOH-H2O(7:3-10:0) carry out
Gradient elution, obtains 5 big sections (A-E).B section (25.5g) through silica gel column chromatography, with petroleum ether-acetone (1:0-0:1) carry out ladder
Degree wash-out, obtains 4 segments (B1-B4).Wherein B3 section (3.0g) through preparation HPLC (methanol-water, 95:After 5) isolating and purifying
To Rxj-33 (180mg)；Equally, B4 part (6.4g) through preparation HPLC (methanol-water, 95:5) obtain Rxj-18 after isolating and purifying
(310mg) with Rxj-19 (230mg).C section (25.5g) 100-200 mesh silica gel mixed sample, silica gel column chromatography, with petroleum ether-acetone
(1:0-0:1) carry out gradient elution, obtain 5 parts (C1-C5), wherein C2 part (3.2g) final through preparation HPLC (methyl alcohol-
Water, 95:5) obtain Rxj-43 (850mg) after isolating and purifying.
The structure elucidation of compound 1-4：
Compound 1 (Rxj-33), colorless gum.It is m/z 547 [M-H] that ESI-MS spectrum provides quasi-molecular ion peak-, knot
Close high-resolution anion HRESI-MS (m/z [M-H]-547.2337, calcd for 547.2332) and13C and DEPT H NMR spectroscopy
The information that figure provides, determines that its molecular formula is C32H36O8, calculating degree of unsaturation is 15.UV spectrum is 206 (4.39), 241
(4.11), there is absorption at 331 (3.89) nm, illustrate in molecule, there is longer conjugated system.Analysis1H and13C H NMR spectroscopy, then tie
Close hsqc spectrum and show to contain 32 carbon signals in compound 1, including 6 methyl, 3 methylene, 8 methines (include 7 alkene
Carbon), 15 quaternary carbons (wherein 1 saturation quaternary carbon).Carefully analyze these as shown by datas 1 be filicinic acid class compound, and with
Know that compound sarothralin is much like.Finally lead in detail analysis HMBC and1H-1H COSY spectrum is it is determined that compound
Isopropyl in sarothralin is replaced by the sec-butyl in 1.So far, the structure of compound 1 is determined.
Similarly, compound 2 is confirmed as the derivative of sarothralen A, C-7 position isopropyl in sarothralen A
Base is replaced by the sec-butyl in 2.Compound 3 is the 15' oxidation product of compound 2, and along with 16', the formation of 17' double bond.
Compound 4 and 3 difference are that carry on the carbonyl of C-7 position is a sec-butyl.Compound 1-4's1H and13C H NMR spectroscopy
Data is as shown in Tables 1 and 2.
The NMR of table 1. compound 1-413C modal data (acetone)
The NMR of table 2. compound 1-41H modal data (acetone)
The structural formula of compound 1-4 is as follows：
Embodiment 2
Measure the bacteriostatic activity of compound 1-4 using metered dilution method：
1 culture medium configuration：Meat soup albumen powder is configured to cultured solution of broth and the meat soup solid culture that concentration is 20g/L
Base, after sterilized process, stand-by.
2 actication of culture：Escherichia coli, typhoid bacillus, staphylococcus aureus, excrement enterobacteria are used successively meat soup solid train
Support inoculation, 37 DEG C of culture 24h.The bacterium of activation is inoculated in meat soup solid medium with asepsis ring, is placed on shaking table, with
220r/min, 37 DEG C of culture 18h, are centrifuged off after nutrient solution again with 0.9% salt solution centrifugal treating 3 times, in order to Accurate Determining
The absorbance of bacterial suspension., in the range of 0.10-600nm, suspension related to this is thin for the absorbance adjusting suspension
Bacteria concentration is 108CFU/mL (when absorbance is 0.1)；Dilute 100 times of bacterial suspension concentration using front with cultured solution of broth extremely
106CFU/mL, stand-by.
3 testing sample configurations：Monomeric compound to be measured is dissolved in DMSO solution, concentration is configured to 4 μ g/mL；Sun
Property comparison：With CTX (cefotaxime) as positive reference substance, with the method according to diluting at double for the meat soup fluid nutrient medium
Test compound sample concentration is adjusted to 1.56 μ g/mL, 0.78 μ g/mL, 0.39 μ g/mL, 0.19 μ g/mL；Blank：Contain
The meat soup Liquid Culture based sols of DMSO 5% volume ratio.
4 antibacterial activity tests：Draw testing sample (4 μ g/mL) 100 μ L with liquid-transfering gun and go in 96 orifice plates, wherein DMSO
Content need to be less than 5% volume ratio；The inoculum continuously adding 100 μ L to each aperture, using the side diluting at double
Test compound sample concentration is adjusted to 2 μ g/mL, 1 μ g/mL, 0.5 μ g/mL, 0.25 μ g/mL, 0.125 μ g/mL, 0.06 μ by method
G/mL, 0.03 μ g/mL, eight concentration gradients of 0.015 μ g/mL.It is 10 that every hole adds the concentration that need to test6The bacterium of CFU/mL
Suspension, after putting culture 24h in insulating box (37 DEG C), is measured with ELIASA.Each monomeric compound is all using above-mentioned side
Method carries out the mensure of minimal inhibitory concentration (MIC value) to each bacterial classification, and testing result is as shown in table 3.
The minimal inhibitory concentration (MIC value) to 4 kinds of bacteriums for the table 3. compound 1-4
From table 3：Compound 1-4 has aobvious to Escherichia coli, typhoid bacillus, staphylococcus aureus, excrement enterobacteria
The inhibitory action writing.Especially compound 1-4 is less than positive control CTX to typhoid bacillus inhibition concentration
(cefotaxime), and compound 1 and 3 pairs of staphylococcus aureuses inhibition concentration also below positive control.These chemical combination
Thing can be used for preparing antibacterial medicine preparation as active component, has preferable medical value.
Embodiment 3
Compound 1-4 antioxidation activity in vitro is tested：
By medicine to be measured and DPPH (final concentration of 100 μM) hybrid reaction, set 3 repeating holes, not pastille is set simultaneously
The blank of thing and Trolox positive control, 30 DEG C, 1h, ELIASA measures OD value, and Detection wavelength is 515nm.It is calculated
Antioxygen rate.
Table 4 sample antioxidation activity in vitro result
Embodiment 4
Tyrosinase inhibitory activity is tested：
Medicine to be measured is mixed with L-Dopa (final concentration 1.25mM), adds tyrosinase (final concentration 25U/mL) to start anti-
Should, set 3 repeating holes, the not blank of drug containing and KojicAcid positive control, room temperature, 5min, enzyme mark are set simultaneously
Instrument measures OD value, and Detection wavelength is 490nm.It is calculated inhibitory activity against tyrosinase.
The inhibitory action activity to tyrosinase for table 5 sample
Embodiment 5
B16 cell melanin generates inhibitory activity experiment：
In 96 porocyte culture plates, B16 cell is mixed with the drug solution to be measured of variable concentrations, sets 8 repeating holes,
The not blank photo of drug containing and KojicAcid positive control are set simultaneously.37 DEG C, 5%CO2Culture 5 days, ELIASA measures OD
Value, Detection wavelength is 405nm, adds MTS, using the OD value of MTS colorimetric determination 490nm.It is calculated B16 cell melanin
Generate inhibiting rate.
The inhibitory action result that table 6 sample generates to B16 cell melanin
Embodiment 6
Promote collagen secretion activity experiment：
In 12 porocyte culture plates, HDFa cell is mixed with the drug solution to be measured of variable concentrations, setting not drug containing
Blank photo and TGF-β positive control.37 DEG C, 5%CO2Culture 3 days, collects cells and supernatant, is stored in -80 DEG C；Add
MTS, using the OD value of MTS colorimetric determination 490nm；By the method detection collagen egg providing in collagen E LISA kit
White secretion, ELIASA measures OD value, and Detection wavelength is 450nm.It is calculated collagen secretion increment rate.
The facilitation result to HDFa cell collagen PE for table 7 sample
Embodiment 7
TNF-α secretion inhibitory activity is tested：
In 12 porocyte culture plates, add PMA (final concentration of 0.01 μ g/mL) in HEKa cell culture fluid, then will
The drug solution to be measured of variable concentrations is mixed with above-mentioned cell solution, arranges the not blank photo of drug containing and PMA comparison simultaneously.37
DEG C, 5%CO2Culture 4-6h, collects cells and supernatant, is stored in -80 DEG C；Add MTS, using MTS colorimetric determination 490nm's
OD value；Detect the secretion of TNF-α by the method providing in TNF-α ELISA kit, ELIASA measures OD value, Detection wavelength is
450nm, tuning wavelength is 540nm.It is calculated TNF-α secretion inhibiting rate.
The inhibitory action result to HEKa cell TNF-α secretion for table 8 sample
Embodiment 8：
Skin whitener formula (W%) that is arbitrary containing compound 1-4 or combining：
The method routinely making cosmetics is obtained the cosmetics of the above-mentioned formula of the present invention.
Embodiment 9：
Emulsion formulations (W%) that are arbitrary containing compound 1-4 or combining：
The method routinely making cosmetics is obtained the cosmetics of the above-mentioned formula of the present invention.
Embodiment 10：
Compound 1-4 is obtained by embodiment 1, by compound 1-4 any one or appoint several mixing compare 1 with excipient weight:1
Or 1:2 ratio adds excipient, pelletizing press sheet.
Embodiment 11：
Compound 1-4 is obtained by embodiment 1, routinely capsule preparations method makes capsule.
Embodiment 12：
First compound 1-4 is obtained by embodiment 1, then makes tablet as follows
Preparation method：By compound 1-4 any one or appoint several mixing mix with auxiliary agent, sieve, in suitable container
Uniformly mix, the granulating mixture compressing tablet obtaining.
Embodiment 13：
Capsule：Compound 1-4 any one or appoint several mixing 100mg
Appropriate starch
Magnesium Stearate proper quantity
Preparation method：By compound 1-4 any one or appoint several mixing mix with auxiliary agent, sieve, in suitable container
Uniformly mix, the mixture obtaining is loaded hard gelatin capsule.
Embodiment 14：
Tablet：Embodiment 1 gained compound 1-4 any one or appoint several mixing 10mg, lactose 180mg, starch 55mg, firmly
Fatty acid magnesium 5mg；
Preparation method：By compound 1-4 any one or appoint several mixing, the mixing of newborn sugar and starch, uniformly moistened with water,
Mixture after moistening sieves and is dried, and after sieve, adds magnesium stearate, then by mixture compressing tablet, every weight 250mg, changes
Compound content is 10mg.
Embodiment 15：
Ampulla：Embodiment 1 gained compound 1-4 any one or appoint several mixing 2mg, sodium chloride 10mg；
Preparation method：By compound 1-4 any one or appoint several mixing and sodium chloride be dissolved in appropriate water for injection,
Filter resulting solution, aseptically load in ampoule bottle.
Embodiment 16：
Capsule：Embodiment 1 gained compound 1-4 any one or appoint several mixing 10mg, lactose 187mg, magnesium stearate
3mg；
Preparation method：By compound 1-4 any one or appoint several mixing mix with auxiliary agent, sieve, uniform mixing, obtaining
Mixture load hard gelatin capsule, each capsule weight 200mg, active component content be 10mg.
Claims (9)
1. filicinic acid class compound R xj-33 (1) shown in following structural formula, Rxj-43 (2), Rxj-18 (3), Rxj-19 (4)
Or its pharmaceutical salts,
2. filicinic acid class compound R xj-33 (1) as claimed in claim 1, Rxj-43 (2), Rxj-18 (3), Rxj-19
(4) or its pharmaceutical salts is it is characterised in that described pharmaceutical salts are to refer to pharmaceutically acceptable salt, it is and organic acid is formed
Salt, described organic acid is tartaric acid, formic acid, acetic acid, ethanedioic acid, butyric acid, maleic acid, butanedioic acid, adipic acid, alginic acid, lemon
Acid, aspartic acid, benzene sulfonic acid, camphoric acid, camphorsulfonic acid, didextrose acid, pentamethylene propionic acid, dodecyl sulphate, ethyl sulfonic acid, Portugal
Heptonic acid, phosphoglycerol, enanthic acid, caproic acid, fumaric acid, 2 ethylenehydrinsulfonic acids, lactic acid, methanesulfonic acid, nicotinic acid, 2 naphthalene sulfonic acids, flutter
Acid, pectinic acid, 3 phenylpropionic acids, neopentanoic acid, propionic acid, p-methyl benzenesulfonic acid and hendecanoic acid.
3. cosmetics, by the filicinic acid class compound 1-4 described in claim 1 any one or appoint several mixtures and cosmetic
Product common carrier forms.
4. the filicinic acid class compound 1-4 described in the claim 1 containing therapeutically effective amount any one or appoint several mixing
Thing or the pharmaceutical composition of its pharmaceutical salts and pharmaceutically acceptable carrier.
5. the filicinic acid class compound 1-4 described in claim 1 any one or appoint several mixtures prepare cosmetics or
Application in food.
6. the filicinic acid class compound 1-4 described in claim 1 any one or appoint several mixtures preparing pre- bacteriological protection
Answering in the cosmetics of skin uncomfortable diseases that Escherichia coli, typhoid bacillus, staphylococcus aureus, excrement Enterobacteriaceae infections lead to
With.
7. the filicinic acid class compound 1-4 described in claim 1 any one or appoint several mixtures in preparation prevention skin
Application in the cosmetics of uncomfortable diseases, described skin uncomfortable diseases are microgroove and/wrinkle, skin erythema, dryness, sensitive skin,
Pruitus, colour of skin inequality or skin blackspot, chafing.
8. the filicinic acid class compound 1-4 described in claim 1 any one or appoint several mixtures or its pharmaceutical salts in system
Application in the medicine of disease being led to by bacterium infection for prevention or treatment, described disease is by Escherichia coli, typhoid fever bar
The disease that bacterium, staphylococcus aureus, excrement Enterobacteriaceae infections are led to.
9. the method for the filicinic acid class compound 1-4 described in preparation claim 1, takes hypericum japonicum that herb is dried, and pulverizes, uses first
Cold soaking 2 times under alcohol room temperature, 24 hours every time, merge extract, vacuum distillation concentrates, and obtains medicinal extract, medicinal extract 100-200 mesh silica gel
Mix sample, silica gel column chromatography, afford chloroform section with chloroform, sample mixed by the chloroform section polyamide of 1.5 times amount, cross MCI post, with 7:
3-10:0 MeOH-H2O carries out gradient elution, obtains 5 big sections A-E, B section through silica gel column chromatography, with 1:0-0:1 oil
Ether-acetone carries out gradient elution, obtains 4 segment B1-B4, wherein B3 section through preparing HPLC, methanol-water, 95:5 isolate and purify
After obtain Rxj-33；Equally, B4 part through prepare HPLC, methanol-water, 95:5 isolate and purify after obtain Rxj-18 and Rxj-19；C
Section 100-200 mesh silica gel mixed sample, silica gel column chromatography, with 1:0-0:1 petroleum ether-acetone carries out gradient elution, obtains 5 portions
Point C1-C5, wherein C2 part through preparing HPLC, methanol-water, 95:5 isolate and purify after obtain Rxj-43.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104547064A (en) * | 2013-10-18 | 2015-04-29 | 王恩瀚 | Pharmaceutical composition for treating facial telangiectasis and preparation method and use thereof |
| CN105233257A (en) * | 2015-11-18 | 2016-01-13 | 桂林华诺威基因药业有限公司 | Repairing and whitening composition |
| CN105906500A (en) * | 2016-04-22 | 2016-08-31 | 中国科学院昆明植物研究所 | Filicinic acid compounds with lipase inhibition effect, and application thereof |
-
2016
- 2016-04-22 CN CN201610255364.3A patent/CN106397169A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104547064A (en) * | 2013-10-18 | 2015-04-29 | 王恩瀚 | Pharmaceutical composition for treating facial telangiectasis and preparation method and use thereof |
| CN105233257A (en) * | 2015-11-18 | 2016-01-13 | 桂林华诺威基因药业有限公司 | Repairing and whitening composition |
| CN105906500A (en) * | 2016-04-22 | 2016-08-31 | 中国科学院昆明植物研究所 | Filicinic acid compounds with lipase inhibition effect, and application thereof |
Non-Patent Citations (7)
| Title |
|---|
| 《J . CHEM. SOC., CHEM. COMMUN.》 * |
| 《PLANTA MEDICA》 * |
| 《中国博士学位论文全文数据库 医药卫生科技辑》 * |
| 《中草药》 * |
| 《中药材》 * |
| 《国外医药 植物药分册》 * |
| 《福建中医药》 * |
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