CN116606273A - 具有美白作用的黄花夹竹桃黄酮的制备方法 - Google Patents
具有美白作用的黄花夹竹桃黄酮的制备方法 Download PDFInfo
- Publication number
- CN116606273A CN116606273A CN202310888561.9A CN202310888561A CN116606273A CN 116606273 A CN116606273 A CN 116606273A CN 202310888561 A CN202310888561 A CN 202310888561A CN 116606273 A CN116606273 A CN 116606273A
- Authority
- CN
- China
- Prior art keywords
- methanol
- oleander
- flavone
- dichloromethane
- silica gel
- 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
- 241000893864 Nerium Species 0.000 title claims abstract description 38
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 title claims abstract description 38
- 229930003944 flavone Natural products 0.000 title claims abstract description 38
- 150000002212 flavone derivatives Chemical class 0.000 title claims abstract description 38
- 235000011949 flavones Nutrition 0.000 title claims abstract description 38
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 230000002087 whitening effect Effects 0.000 title claims abstract description 23
- 235000004204 Foeniculum vulgare Nutrition 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000007670 refining Methods 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 22
- 239000012071 phase Substances 0.000 claims description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000741 silica gel Substances 0.000 claims description 18
- 229910002027 silica gel Inorganic materials 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003208 petroleum Substances 0.000 claims description 13
- 238000010898 silica gel chromatography Methods 0.000 claims description 11
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000000287 crude extract Substances 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 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 4
- 101710147108 Tyrosinase inhibitor Proteins 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 4
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 4
- 238000007873 sieving Methods 0.000 claims description 4
- 238000002791 soaking Methods 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 4
- 239000012267 brine Substances 0.000 claims description 3
- 238000013375 chromatographic separation Methods 0.000 claims description 3
- 238000002481 ethanol extraction Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 2
- 241000212314 Foeniculum Species 0.000 claims 4
- 102000003425 Tyrosinase Human genes 0.000 abstract description 26
- 108060008724 Tyrosinase Proteins 0.000 abstract description 26
- 230000005764 inhibitory process Effects 0.000 abstract description 24
- 240000006927 Foeniculum vulgare Species 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 14
- 239000002994 raw material Substances 0.000 abstract 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 16
- 239000003814 drug Substances 0.000 description 13
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 13
- 239000000523 sample Substances 0.000 description 10
- 229960004441 tyrosine Drugs 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229960000271 arbutin Drugs 0.000 description 9
- 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 8
- 239000002537 cosmetic Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 235000013399 edible fruits Nutrition 0.000 description 7
- 239000012085 test solution Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000490 cosmetic additive Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229930003935 flavonoid Natural products 0.000 description 3
- 235000017173 flavonoids Nutrition 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- -1 hydroxypropyl Chemical group 0.000 description 3
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 3
- 229960004705 kojic acid Drugs 0.000 description 3
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- AHMIDUVKSGCHAU-UHFFFAOYSA-N Dopaquinone Natural products OC(=O)C(N)CC1=CC(=O)C(=O)C=C1 AHMIDUVKSGCHAU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 102000006833 Multifunctional Enzymes Human genes 0.000 description 2
- 108010047290 Multifunctional Enzymes Proteins 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003796 beauty Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000001815 facial effect Effects 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229930015704 phenylpropanoid Natural products 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 235000019154 vitamin C Nutrition 0.000 description 2
- 239000011718 vitamin C Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000258957 Asteroidea Species 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 235000017159 Crataegus pinnatifida Nutrition 0.000 description 1
- 241000657480 Crataegus pinnatifida Species 0.000 description 1
- 235000002176 Foeniculum vulgare var vulgare Nutrition 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 206010059516 Skin toxicity Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229930182479 fructoside Natural products 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008099 melanin synthesis Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 150000002995 phenylpropanoid derivatives Chemical class 0.000 description 1
- 125000001474 phenylpropanoid group Chemical group 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000008591 skin barrier function Effects 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 231100000438 skin toxicity Toxicity 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
本发明公开了具有美白作用的黄花夹竹桃黄酮的制备方法:以小茴香为原料,经乙醇提取、萃取分离、分离精制得到黄花夹竹桃黄酮。本发明的方法制备得到的黄花夹竹桃黄酮具有酪氨酸酶抑制作用,可望开发成美白产品。
Description
技术领域
本发明属于生物医药技术领域,具体涉及具有美白作用的黄花夹竹桃黄酮的制备方法。
背景技术
经过紫外线的照射,人的皮肤会生成黑色素,黑色素的过度生成会导致皮肤出现色斑、暗沉、变黑、肤色不均等问题,影响了美观,给人们带来了困扰。美白肌肤,减少黑色素的产生是广大爱美人士的迫切需求。紫外线会激活酪氨酸酶,酪氨酸酶会参与L-酪氨酸氧化为多巴和多巴氧化为多巴醌两个过程,多巴醌经过一系列反应生成黑色素,抑制酪氨酸酶活性能抑制黑色素生成从而达到美白的效果。随着人们生活水平提高,对优质生活的要求也越来越高,在化妆品市场上,天然且安全的护肤品与化妆品深受消费人群追捧。传统具备美白效果的功效性化妆品添加剂主要包含维C及其衍生物、氢醌、熊果苷、曲酸以及果酸等成分,然而在这些添加剂中,维C稳定性较差且难以被皮肤吸收,熊果苷具有较好的抑制酪氨酸酶活性的效果,是市售美白功效性化妆品中常用的添加成分,但光照和紫外线都会对熊果苷的稳定性造成影响,提倡只在夜间使用。《化妆品安全技术规范》(2015年版)禁止化妆品中添加氢醌,因其长期使用会有致癌性、皮肤毒性等毒副作用。曲酸未列入我国《化妆品安全技术规范》中,但被世界卫生组织列为“3类致癌物质”,研究表明高浓度曲酸有一定的细胞毒性。果酸目前被广泛地用于痤疮的治疗,使用添加果酸的化妆品经长时间日照可能会导致皮肤癌,使用含量过高会破坏皮肤屏障。然而,植物来源的天然酪氨酸酶抑制剂,通过多途径、多***、多靶点发挥美白功效,具有更小的毒副作用。因此,使用添加天然草本植物精华的美容用品已经成为全球趋势,寻找新型植物美白成分的应用前景也非常广阔。
小茴香为伞形科植物茴香Foeniculum vulgareMill.的干燥成熟果实,其原名蘹香,其药用历史悠久,始载于《唐本草》,有一千多年药用历史。除药用外,小茴香还是常用的食品香料,故为药食两用之佳品。小茴香分布广泛,主要分布于地中海地区,我国主要分布于西北地区的山西、甘肃、内蒙古,以及东北地区的辽宁等地区,其资源丰富,以栽培为主,栽培面积广泛,其中以山西产量最大、内蒙古河套附近产品质优。
小茴香主要含有挥发油,以及黄酮、苯丙素、糖苷、脂肪油、酚酸等类型的化合物,目前研究开发主要集中于挥发油,且以成分分析为主,对化合物分离纯化及鉴定报道不多,其富含的非挥发性成分,如黄酮类缺乏深入研究开发,本发明发现,其中的部分黄酮具有良好的抑制酪氨酸酶作用,从而抑制制酪氨酸酶催化L-酪氨酸氧化为多巴和多巴氧化为多巴醌两个过程,提示小茴香中的某些黄酮可能具有较良好的美白作用。
发明内容
本发明的目的在于提供具有美白作用的黄花夹竹桃黄酮的制备方法。
黄花夹竹桃黄酮的结构式为,其制备方法为:
(1)乙醇提取:小茴香样品20 kg粉碎过10目筛,在10 L的体积浓度为75%乙醇中回流提取,每次10L,每次2小时,提取5次;合并得提取液,通过旋转蒸发仪减压除去溶剂得到粗提物A;
(2)萃取分离:将粗提物A加水混悬,使用石油醚、乙酸乙酯、正丁醇依次分别萃取五次,合并萃取液,减压浓缩得到石油醚相、乙酸乙酯相B、正丁醇相和水相;
(3)分离精制:乙酸乙酯相B经200-300目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为100:1-1:1,馏分经正向硅胶板以石油醚-乙酸乙酯1:1为展开剂展开,合并Rf值在0.3~0.8之间的馏分Fr.7,Fr.7经100-200目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为50:1-1:1,馏分经正向硅胶板以二氯甲烷-甲醇10:1为展开剂展开,合并Rf值在0.5~0.7之间的馏分Fr.7.9,Fr.7.9以100-200目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为30:1-1:1,馏分经正向硅胶板以二氯甲烷-甲醇8:1为展开剂展开,合并Rf值在0.5~0.8之间的馏分Fr.7.9.2,Fr.7.9.2经MCI 柱色谱以甲醇-水梯度洗脱,甲醇-水的体积比为20∶80~100∶0,馏分经正向硅胶板以二氯甲烷-甲醇8:1加2滴甲酸为展开剂展开,合并Rf值在0.7~0.8之间的馏分Fr.7.9.2.3,Fr.7.9.2.3再经Sephadex LH-20 色谱分离,色谱分离条件为甲醇,高度:1.5米,流速:4秒每滴;最后以半制备液相纯化,色谱条件为乙腈-水23∶77、体积流量3 ml/min、检测波长:254 nm,得到化合物黄花夹竹桃黄酮。
所述小茴香为盐炙小茴香。
盐炙小茴香的制备:取小茴香,每公斤小茴香加100ml盐水,密封,闷透30min,置炒制容器内,文火加热,温度为110-120℃,炒至微黄时,取出,放凉,备用。
所述盐水为饱和食盐水。
用该制备方法得到的黄花夹竹桃黄酮在制备酪氨酸酶抑制剂产品中的应用。
一种美白产品,包含由上述制备方法得到的黄花夹竹桃黄酮。
本发明优点:
本发明的优点和积极效果在于,开发了一种新的黄花夹竹桃黄酮的制备方法。
本发明的制备方法得到的黄花夹竹桃黄酮具有酪氨酸酶抑制作用,可用于美白产品。
附图说明
图1为黄花夹竹桃黄酮的化学结构。
图2为黄花夹竹桃黄酮的1H-NMR谱。
图3为黄花夹竹桃黄酮的13C-NMR(DEPT)谱。
图4为β-熊果苷对酪氨酸酶的浓度抑制曲线。
图5为黄花夹竹桃黄酮对酪氨酸酶的浓度抑制曲线。
具体实施方式
本发明提供了具有美白作用的黄花夹竹桃黄酮的制备方法。
具有美白作用的黄花夹竹桃黄酮的制备方法。
黄花夹竹桃黄酮的结构式为,其制备方法为:
(1)乙醇提取:小茴香样品20 kg粉碎过10目筛,在10 L的体积浓度为75%乙醇中回流提取,每次10 L,每次2小时,提取5次;合并得提取液,通过旋转蒸发仪减压除去溶剂得到粗提物A;
(2)萃取分离:将粗提物A加水混悬,使用石油醚、乙酸乙酯、正丁醇依次分别萃取五次,合并萃取液,减压浓缩得到石油醚相、乙酸乙酯相B、正丁醇相和水相;
(4)分离精制:乙酸乙酯相B经200-300目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为100:1-1:1,馏分经正向硅胶板以石油醚-乙酸乙酯1:1为展开剂展开,合并Rf值在0.3~0.8之间的馏分Fr.7,Fr.7经100-200目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为50:1-1:1,馏分经正向硅胶板以二氯甲烷-甲醇10:1为展开剂展开,合并Rf值在0.5~0.7之间的馏分Fr.7.9,Fr.7.9以100-200目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为30:1-1:1,馏分经正向硅胶板以二氯甲烷-甲醇8:1为展开剂展开,合并Rf值在0.5~0.8之间的馏分Fr.7.9.2,Fr.7.9.2经MCI 柱色谱以甲醇-水梯度洗脱,甲醇-水的体积比为20∶80~100∶0,馏分经正向硅胶板以二氯甲烷-甲醇8:1加2滴甲酸为展开剂展开,合并Rf值在0.7~0.8之间的馏分Fr.7.9.2.3,Fr.7.9.2.3再经Sephadex LH-20 色谱分离,色谱分离条件为甲醇,高度:1.5米,流速:4秒每滴;最后以半制备液相纯化,色谱条件为乙腈:水23∶77、体积流量3 ml/min、检测波长:254 nm,纯化得到化合物黄花夹竹桃黄酮。
小茴香为盐炙小茴香。
盐炙小茴香的制备:取小茴香,每公斤小茴香加100ml盐水,密封,闷透30min,置炒制容器内,文火加热,温度为110-120℃,炒至微黄时,取出,放凉,备用。
盐水为饱和食盐水。
用该制备方法得到的黄花夹竹桃黄酮在制备酪氨酸酶抑制剂产品中的应用。
一种美白产品,包含由上述制备方法得到的黄花夹竹桃黄酮。
下面对本发明作进一步的说明,但不以任何方式对本发明加以限制,基于本发明所作的任何变换,均属于本发明的保护范围。
实施例1
盐炙小茴香的制备
取食盐,加水,制成饱和溶液,即为盐水。
取小茴香20kg,加2000ml盐水,密封,闷透30min,置炒制容器内,文火加热,温度为110-120℃,炒至微黄时,取出,放凉,备用。
实施例2
黄花夹竹桃黄酮的制备方法
1.1 材料
色谱硅胶(100~200目,200~300目,青岛海洋化工厂);GF254薄层色谱硅胶(青岛海洋化工厂);LH-20羟丙基葡聚糖凝胶(美国Pharmacia公司);反相C18柱色谱材料(ODS,德国Merck公司);薄层色谱显色剂(10% 硫酸乙醇溶液);甲醇、乙醇、丙酮、正丁醇、乙酸乙酯、二氯甲烷、石油醚等试剂为重蒸的工业或化学纯溶剂;色谱乙腈(上海星可高纯溶剂有限公司)。
小茴香药材于2022年9月购自新螺蛳湾药材市场,由云南中医药大学李宏哲副教授鉴定为伞形科植物茴香Foeniculum vulgare Mill.的干燥成熟果实。
1.2 仪器
Bruker Avance III 400 MHz及Bruker DRX 500 MHz超导核磁共振仪,TMS为内标(德国Bruker公司);高效液相色谱仪Agilent 1200型(美国Agilent公司);离子井飞行时间质谱仪Esquire HCT型(德国Bruker公司);万分之一分析天平FA2004(上海舜宇恒平科学仪器有限公司);循环水式多用真空泵 SHB-Ⅲ(巩义市予华仪器有限公司);海道夫旋转蒸发仪Hei-VAP Core HL/G(德国heidolph)。
2 提取分离过程
盐炙小茴香样品20 kg粉碎过10目筛,在10 L的75%乙醇中回流提取,每次10L,每次2小时,提取5次。合并得提取液,通过旋转蒸发仪减压除去溶剂得到2.387 kg粗提物,粗提物加水混悬并使用石油醚、乙酸乙酯、正丁醇依次分别萃取五次,合并萃取液,减压浓缩得到石油醚相203.6g、乙酸乙酯相73.9 g、正丁醇相316.7 g和水相759.3 g。乙酸乙酯部位经200-300目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为100:1-1:1,馏分经正向硅胶板以石油醚-乙酸乙酯1:1为展开剂展开,合并Rf值在0.3~0.8之间的馏分Fr.7,Fr.7经100-200目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为50:1-1:1,馏分经正向硅胶板以二氯甲烷-甲醇10:1为展开剂展开,合并Rf值在0.5~0.7之间的馏分Fr.7.9,Fr.7.9以100-200目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为30:1-1:1,馏分经正向硅胶板以二氯甲烷-甲醇8:1为展开剂展开,合并Rf值在0.5~0.8之间的馏分Fr.7.9.2,Fr.7.9.2经MCI 柱色谱以甲醇-水梯度洗脱,甲醇-水的体积比为20∶80~100∶0,馏分经正向硅胶板以二氯甲烷-甲醇8:1加2滴甲酸为展开剂展开,合并Rf值在0.7~0.8之间的馏分Fr.7.9.2.3,Fr.7.9.2.3再经Sephadex LH-20 色谱分离,色谱条件为甲醇,高度:1.5米,流速:4秒每滴;最后以半制备液相纯化,色谱条件为乙腈:水23∶77、体积流量3 ml/min、检测波长:254 nm,纯化得到化合物黄花夹竹桃黄酮4.2 mg。该化合物的化学结构见图1,图2为黄花夹竹桃黄酮的1H-NMR谱。图3为黄花夹竹桃黄酮的13C-NMR(DEPT)谱。
黄花夹竹桃黄酮的理化常数及波谱数据
淡黄色粉末(甲醇),分子式:C16H12O5;1H-NMR(400MHz,CD3OD)δ H:7.45(2H,d,J= 8.5Hz,H-2′,6′),7.02(2H,d,J= 8.5 Hz,H-3′,5′),6.22(1H,d,J= 2.1 Hz,H-8),6.19(1H,d,J= 2.1 Hz,H-6),3.78(3H,s,5-OMe).13C-NMR(100MHz,CD3OD)δ C:175.9(s,C-4),162.1(s,C-7),160.5(s,C-4′),160.1(s,C-2),159.8(s,C-5),159.6(s,C-9),127.5(d,C-2′,6′),121.6(s,C-1′),115.9(d,C-3′,5′),106.9(d,C-3),106.7(s,C-10),96.7(d,C-6),96.0(d,C-8),57.6(q,4-OMe)。
实施例3
抗酪氨酸酶活性的作用研究
本方法为参考文献的基础上修改。(Li ZY, Zhao P, Song SJ, Huang XX.Chiral resolution of racemic phenylpropanoids with tyrosinaseinhibitoryactivities from the fruits of Crataegus pinnatifida Bge. J FoodBiochem. 2022 Oct;46(10):e14304.)
1 材料与仪器
1.1 材料
酪氨酸酶(Sigma-Aldrich公司);L-酪氨酸(上海麦克林生化科技有限公司)、β-熊果苷(上海源叶生物科技有限公司)。
1.2 仪器
Synergy2多功能酶标仪(美国BIOTEK)。
酪氨酸酶抑制活性测试
2.1溶液的配置
2.1.1磷酸盐缓冲液的配置
精密量取20 ml 10×PBS缓冲液,用超纯水稀释至200 ml,最后使用0.2mol/L氢氧化钠调节pH至规定范围(6.5~7.5)即得PBS缓冲液。
酪氨酸酶试液的配置
精密移取提前分装好的100 units/ml的酪氨酸酶(SLCN1560)9 ml,加入PBS缓冲液稀释至30 ml即得30 units/ml的酪氨酸酶试液,将试液放入-20 ℃冰箱待用。
酪氨酸溶液的配置
精密称取5 mg L-酪氨酸(批号:C14856769)粉末于100 ml EP管中加入50 ml PBS缓冲液,摇匀,即得0.1 mg/ml L-酪氨酸溶液,放置,待用。
样品溶液的配置
(1)、阳性药溶液的配置
精密称取β-熊果苷(批号:T17S6B1)粉末4 mg,加入30 ul DMSO使其完全溶解,再使用移液枪精密加入970 ul PBS即得4 mg/ml阳性药试液,再将阳性药依次梯度稀释浓度为2 mg/ml、1 mg/ml、0.5 mg/ml、0.25 mg/ml,待用。
(2)、待测样品溶液的配置
精密称取样品(黄花夹竹桃黄酮)适量,加入30 ul DMSO使其完全溶解,再精密加入PBS使其浓度依次为1 mg/ml、0.5 mg/ml、0.25 mg/ml、0.125 mg/ml、0.0625 mg/ml,待用。
酪氨酸酶活性抑制率的测定
用移液枪按表1的体积向96孔板依次加入PBS缓冲液、不同浓度梯度的化合物受试液、不同浓度梯度的熊果苷对照液和酪氨酸酶液,37 ℃下孵育10 min后,加入L-酪氨酸试液,同等条件下孵育30 min,孵育完成后立即放入多功能酶标仪在492 nm测定其吸光度,并记录数据,每个浓度实验做3个平行组,使用3组数据的平均值,按照以下公式计算测定化合物对酪氨酸酶的抑制率:
抑制率=[1-(AT-AB)/(AC-AN)]×100%
其中,T:为加样品且加酪氨酸的反应液组别;B:为加样品且未加酪氨酸的反应液组别;C:为未加样品且加酪氨酸的反应液组别;N:为未加样品且未加酪氨酸的反应液组别。AT:为T组反应液在492nm处测得的吸光度值;AB:为B组反应液在492nm处测得的吸光度值;AC:为C组反应液在492nm处测得的吸光度值;AN:为N组反应液在492nm处测得的吸光度值。
表1 反应液组成
样品/阳性药(ul) | PBS(ul) | 酪氨酸酶(ul) | 酪氨酸(ul) | 总量(ul) | |
T | 40 | 40 | 40 | 120 | |
B | 40 | 40 | 40 | 120 | |
C | 40 | 40 | 40 | 120 | |
N | 80 | 40 | 120 |
2.3酪氨酸酶抑制实验结果
阳性药β-熊果苷对酪氨酸酶活性的浓度抑制结果如图4所示,其抑制率由高到低依次为62.79%;50.24%;41.48%;33.19%;18.73%,其中阳性药对酪氨酸酶抑制率均随着受试液浓度提升而提升,浓度小于1 mg/ml时,阳性药的抑制率随浓度的升高增加得更快,当浓度大于1 mg/ml时,增长得较为缓慢,表现为浓度依赖性抑制,其IC50值为1.784 mg/ml。
化合物对酪氨酸酶活性的浓度抑制结果如图5所示,其抑制率由高到低依次为88.27%;85.01%;80.29%;60.78%;33.15%,其对酪氨酸酶抑制率同样随着受试液浓度提升而提升,化合物浓度在0.25 mg/ml以下时抑制率随浓度增加得较快,当浓度大于0.25 mg/ml时增长速率变得更加缓慢,表现为浓度依赖性抑制,其IC50值为0.092 mg/ml。
结果分析
抑制率实验结果显示,化合物浓度为1 mg/ml时对酪氨酸酶的抑制率为88.27%,而阳性药β-熊果苷的抑制率只有41.48%,同时化合物IC50值为0.092 mg/ml,为阳性药β-熊果苷(IC50值为1.784 mg/ml)的十九分之一,表明化合物抑制酪氨酸酶的活性远远大于β-熊果苷,具有更好的美白效果。以上结果均表明,化合物黄花夹竹桃黄酮具有比阳性药更好的美白活性。且该黄酮类化合物为首次从小茴香中分离得到,未来,将拥有广阔的发展前景。
实施例4
含有黄花夹竹桃黄酮美白面霜的制备
按重量份计包含以下组分:
称取黄花夹竹桃黄酮0.25g溶于水中,得到黄花夹竹桃黄酮水溶液,然后再依次加入玫瑰精油0.1g,珍珠粉1.3g, 甲基纤维素4 .5g, 尿素 12g, ***树胶 0 .7g,苯氧乙醇0 .05g, 维生素E 0 .05g,混合均匀后密封,得到美白面霜。
实施例5
一种美白面膜,在常规面膜基材基础上添加对丙烯基苯酚糖苷制成。
Claims (5)
1.一种黄花夹竹桃黄酮的制备方法,其特征在于,黄花夹竹桃黄酮的结构式为,其制备方法为:
(1)乙醇提取:小茴香样品20 kg粉碎过10目筛,在10 L的体积浓度为75%乙醇中回流提取,每次10L,每次2小时,提取5次;合并得提取液,通过旋转蒸发仪减压除去溶剂得到粗提物A;
(2)萃取分离:将粗提物A加水混悬,使用石油醚、乙酸乙酯、正丁醇依次分别萃取五次,合并萃取液,减压浓缩得到石油醚相、乙酸乙酯相B、正丁醇相和水相;
(3)分离精制:乙酸乙酯相B经200-300目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为100:1-1:1,馏分经正向硅胶板以石油醚-乙酸乙酯1:1为展开剂展开,合并Rf值在0.3~0.8之间的馏分Fr.7,Fr.7经100-200目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为50:1-1:1,馏分经正向硅胶板以二氯甲烷-甲醇10:1为展开剂展开,合并Rf值在0.5~0.7之间的馏分Fr.7.9,Fr.7.9以100-200目正向硅胶色谱,以二氯甲烷-甲醇梯度洗脱,二氯甲烷-甲醇的体积比为30:1-1:1,馏分经正向硅胶板以二氯甲烷-甲醇8:1为展开剂展开,合并Rf值在0.5~0.8之间的馏分Fr.7.9.2,Fr.7.9.2经MCI 柱色谱以甲醇-水梯度洗脱,甲醇-水的体积比为20∶80~100∶0,馏分经正向硅胶板以二氯甲烷-甲醇8:1加2滴甲酸为展开剂展开,合并Rf值在0.7~0.8之间的馏分Fr.7.9.2.3,Fr.7.9.2.3再经Sephadex LH-20 色谱分离,色谱分离条件为甲醇,高度:1.5米,流速:4秒每滴;最后以半制备液相纯化,色谱条件为乙腈-水23∶77;体积流量3 ml/min;检测波长:254 nm,得到化合物黄花夹竹桃黄酮。
2.根据权利要求1所述的制备方法,其特征在于,所述的小茴香为盐炙小茴香,制备方法为:取小茴香,每公斤小茴香加100ml盐水,密封,闷透30min,置炒制容器内,文火加热,温度为110-120℃,炒至微黄时,取出,放凉,备用。
3.根据权利要求2所述的制备方法,其特征在于,所述的盐水为饱和食盐水。
4.一种用权利要求1制备方法得到的黄花夹竹桃黄酮在制备酪氨酸酶抑制剂产品中的应用。
5.一种美白产品,其特征在于,包含由权利要求1的制备方法得到的黄花夹竹桃黄酮。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310888561.9A CN116606273B (zh) | 2023-07-19 | 2023-07-19 | 具有美白作用的黄花夹竹桃黄酮的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310888561.9A CN116606273B (zh) | 2023-07-19 | 2023-07-19 | 具有美白作用的黄花夹竹桃黄酮的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN116606273A true CN116606273A (zh) | 2023-08-18 |
CN116606273B CN116606273B (zh) | 2023-09-26 |
Family
ID=87683932
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310888561.9A Active CN116606273B (zh) | 2023-07-19 | 2023-07-19 | 具有美白作用的黄花夹竹桃黄酮的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN116606273B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117462539A (zh) * | 2023-12-26 | 2024-01-30 | 云南中医药大学 | 一种二氢黄酮醇型化合物的抗冠状病毒用途及制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102091104A (zh) * | 2009-12-15 | 2011-06-15 | 上海医药工业研究院 | 从刺山柑中获得精制提取物的方法及该提取物的应用 |
US20120128798A1 (en) * | 2010-11-22 | 2012-05-24 | Phoenix Biotechnology, Inc. | Method of Treating Neurological Conditions with Extract of Nerium Species or Thevetia Species |
CN108697646A (zh) * | 2016-02-04 | 2018-10-23 | 干细胞诊疗公司 | 用于抵抗化学疗法诱导的心脏毒性的药物组合物和方法 |
CN109265503A (zh) * | 2018-11-30 | 2019-01-25 | 云南民族大学 | 一种黄酮类化合物及其制备方法和应用 |
CN115856132A (zh) * | 2022-12-08 | 2023-03-28 | 杭州龙上科技有限公司 | 一种玫瑰花美白成分的筛选与分离纯化的方法 |
-
2023
- 2023-07-19 CN CN202310888561.9A patent/CN116606273B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102091104A (zh) * | 2009-12-15 | 2011-06-15 | 上海医药工业研究院 | 从刺山柑中获得精制提取物的方法及该提取物的应用 |
US20120128798A1 (en) * | 2010-11-22 | 2012-05-24 | Phoenix Biotechnology, Inc. | Method of Treating Neurological Conditions with Extract of Nerium Species or Thevetia Species |
CN108697646A (zh) * | 2016-02-04 | 2018-10-23 | 干细胞诊疗公司 | 用于抵抗化学疗法诱导的心脏毒性的药物组合物和方法 |
CN109265503A (zh) * | 2018-11-30 | 2019-01-25 | 云南民族大学 | 一种黄酮类化合物及其制备方法和应用 |
CN115856132A (zh) * | 2022-12-08 | 2023-03-28 | 杭州龙上科技有限公司 | 一种玫瑰花美白成分的筛选与分离纯化的方法 |
Non-Patent Citations (3)
Title |
---|
HASSAN RAKHSHANDEH, ET AL: ""Effects of Capparis Spinosa extract on the neuropathic pain induced by chronic constriction injury in rats"", 《METABOLIC BRAIN DISEASE》, pages 2839 * |
XI LEI,ET AL: ""Chemical constituent from the peel of Trichosanthes kirilowii Maxim and their NF-jB inhibitory activity"", 《NATURAL PRODUCT RESEARCH》, pages 1 - 5 * |
字成庭;杨柳等: "" 天然二苯乙基类化合物的结构、来源及药理活性研究进展"", 《广州化工》, vol. 48, no. 9, pages 40 - 49 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117462539A (zh) * | 2023-12-26 | 2024-01-30 | 云南中医药大学 | 一种二氢黄酮醇型化合物的抗冠状病毒用途及制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN116606273B (zh) | 2023-09-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Zheng et al. | Tyrosinase inhibition constituents from the roots of Morus australis | |
Zhang et al. | Separation, purification and identification of antioxidant compositions in black rice | |
CN103211732B (zh) | 一种具酪氨酸酶抑制活性的混合物的制备方法及其应用 | |
JP5439644B2 (ja) | ウーロン茶又は紅茶から抽出された血糖値上昇抑制剤及びミトコンドリア膜電位上昇剤 | |
Han et al. | In vitro evaluation of tectoridin, tectorigenin and tectorigenin sodium sulfonate on antioxidant properties | |
Yang et al. | Flavonoid C-glycosides from star fruit and their antioxidant activity | |
CN116606273B (zh) | 具有美白作用的黄花夹竹桃黄酮的制备方法 | |
Jia et al. | Non-flavonoid phenolics from Averrhoa carambola fresh fruit | |
CN108530500B (zh) | 一种合欢皮木脂素苷单体的制备方法及其应用 | |
CN109316416A (zh) | 一种艾叶提取物及其在化妆品中的应用 | |
Molčanová et al. | Antiproliferative and cytotoxic activities of C-Geranylated flavonoids from Paulownia tomentosa Steud. Fruit | |
CN104610054B (zh) | 一种咖啡酰对羟基苯酚酯及其制备方法和在制备酪氨酸酶抑制剂中的应用 | |
Dang et al. | Preparative separation of 1, 1-diphenyl-2-picrylhydrazyl inhibitors originating from Saxifraga sinomontana employing medium-pressure liquid chromatography in combination with reversed-phase liquid chromatography | |
CN108299368B (zh) | 黄酮类化合物及其制备方法与应用 | |
Shi et al. | A novel thiolysis‐high‐performance liquid chromatography method for the determination of proanthocyanidins in grape seeds | |
CN106565444B (zh) | 山药地上部分菲类化合物的提取方法及应用 | |
CN114146083B (zh) | 小槐花提取物和活性成分及其在制备治疗糖脂代谢综合紊乱的产品方面中的应用 | |
CN112194704B (zh) | 一种甾体皂苷类化合物及其制备方法和应用 | |
CN116589515B (zh) | 具有美白作用的对丙烯基苯酚糖苷的制备方法 | |
CN111548255B (zh) | 黄杉中二萜类化合物及其制备方法和在制药中的用途 | |
Niu et al. | Development of a method to screen and isolate xanthine oxidase inhibitors from black bean in a single step: Hyphenation of semipreparative liquid chromatography and stepwise flow rate countercurrent chromatography | |
CN111217790B (zh) | 一种酚类缩醛衍生物的制备及其用途 | |
CN109705074B (zh) | 一种具有抗氧化活性的地黄呋喃醛衍生物及其制备方法和应用 | |
CN114736251B (zh) | 金丝***的提取单体***素b及其提取方法和应用 | |
CN116675602B (zh) | 一种降海松烷型二萜及其制备方法和应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240103 Address after: Room 12, 2nd Floor, Building 3, No. 39 Jiatai Road, China (Shanghai) Pilot Free Trade Zone, Pudong New Area, Shanghai, 200000 Patentee after: Shanghai Haibeilizhi Cosmetics Co.,Ltd. Address before: No.1076, Yuhua Road, Chenggong District, Kunming, Yunnan 650500 Patentee before: Yunnan University of Traditional Chinese Medicine |