CN116589515A - Preparation method of p-propenyl phenol glycoside with whitening effect - Google Patents
Preparation method of p-propenyl phenol glycoside with whitening effect Download PDFInfo
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- CN116589515A CN116589515A CN202310888639.7A CN202310888639A CN116589515A CN 116589515 A CN116589515 A CN 116589515A CN 202310888639 A CN202310888639 A CN 202310888639A CN 116589515 A CN116589515 A CN 116589515A
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- methanol
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- silica gel
- fennel
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- 229930182470 glycoside Natural products 0.000 title claims abstract description 35
- -1 p-propenyl phenol glycoside Chemical class 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 230000002087 whitening effect Effects 0.000 title claims abstract description 15
- 241000212314 Foeniculum Species 0.000 claims abstract description 21
- 235000004204 Foeniculum vulgare Nutrition 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 4
- 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 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000012071 phase Substances 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 19
- 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
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 16
- 239000003208 petroleum Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- 230000002829 reductive effect Effects 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
- 238000002156 mixing 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
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 4
- 238000004587 chromatography analysis Methods 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
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 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
- 238000010992 reflux Methods 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 238000010898 silica gel chromatography 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
- 101710147108 Tyrosinase inhibitor Proteins 0.000 claims description 3
- 239000012267 brine Substances 0.000 claims description 3
- 238000002481 ethanol extraction Methods 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 238000007873 sieving Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- 230000002441 reversible effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 102000003425 Tyrosinase Human genes 0.000 abstract description 28
- 108060008724 Tyrosinase Proteins 0.000 abstract description 28
- 230000005764 inhibitory process Effects 0.000 abstract description 25
- 230000000694 effects Effects 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 16
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 14
- 239000003814 drug Substances 0.000 description 11
- 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 9
- 229960004441 tyrosine Drugs 0.000 description 9
- 239000000523 sample Substances 0.000 description 8
- 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 description 7
- 229960000271 arbutin Drugs 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000012085 test solution 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
- 238000002835 absorbance Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 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 4
- 229930015704 phenylpropanoid Natural products 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 150000008505 β-D-glucopyranosides Chemical class 0.000 description 3
- LSMSSYSRCUNIFX-ONEGZZNKSA-N 1-methyl-4-[(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=C(C)C=C1 LSMSSYSRCUNIFX-ONEGZZNKSA-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
- 241000196324 Embryophyta Species 0.000 description 2
- 102000006833 Multifunctional Enzymes Human genes 0.000 description 2
- 108010047290 Multifunctional Enzymes Proteins 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000008099 melanin synthesis Effects 0.000 description 2
- 210000002752 melanocyte Anatomy 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 210000000434 stratum corneum Anatomy 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 208000020154 Acnes Diseases 0.000 description 1
- 241000258957 Asteroidea Species 0.000 description 1
- 235000017159 Crataegus pinnatifida Nutrition 0.000 description 1
- 241000657480 Crataegus pinnatifida Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 240000006927 Foeniculum vulgare Species 0.000 description 1
- 235000002176 Foeniculum vulgare var vulgare Nutrition 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 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 description 1
- 230000032683 aging Effects 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 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
- 210000001339 epidermal cell Anatomy 0.000 description 1
- ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 150000002995 phenylpropanoid derivatives Chemical class 0.000 description 1
- 125000001474 phenylpropanoid group Chemical group 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- 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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
The invention discloses a preparation method of p-propenyl phenol glycoside with whitening effect, which comprises the following steps: the p-propenyl phenol glycoside is obtained by taking fennel as a raw material and extracting, separating and refining the fennel with ethanol. The p-propenyl phenol glycoside prepared by the method has tyrosinase inhibition effect and is expected to be developed into a whitening product.
Description
Technical Field
The invention belongs to the technical field of biological medicines, and particularly relates to a preparation method of p-propenyl phenol glycoside with a whitening effect.
Background
Skin is the largest organ of human body, and people usually use skin care products to create a good local environment for the skin so as to be beneficial to the survival and growth of the skin, thereby achieving the effects of resisting aging, resisting wrinkles, preserving moisture and removing acnes. The degree of skin whitening has a great relationship with melanin, which is transferred to keratinocytes, epidermal cells and the stratum corneum after being produced by melanocytes and finally excreted with the exfoliation of the stratum corneum, thereby affecting the color of the skin or forming color spots. Tyrosinase (TYR) is a rate-limiting enzyme for regulating and controlling melanin generation by a human body, tyrosinase is only produced by melanocytes, the melanin synthesis amount is related to the activity of tyrosinase, and the generation of melanin can be effectively regulated and controlled by regulating and controlling the expression amount of tyrosinase in the cells, so that the skin whitening effect is achieved, therefore, a melanin biosynthesis inhibitor based on inhibiting the activity of tyrosinase becomes a hot spot in the research field, and the development of a compound inhibitor through combination with a tyrosinase active center is a category with higher attention.
The fructus Foeniculi is Foeniculi of UmbelliferaeFoeniculum vulgareThe dry mature fruits of Mill, their original name being Fengxiang, have a long history of medicinal use, and were originally carried in Tang Ben Cao for a thousand years. Besides medicinal use, fennel is also a common food flavor, so the fennel is a good product for both medicine and food. The fennel is widely distributed in the Mediterranean region, the Chinese is mainly distributed in the Shanxi, gansu and inner Mongolia regions of northwest region, liaoning regions of northeast region and the like, the resources are rich, the cultivation is mainly carried out, the cultivation area is wide, and the Shanxi yield is maximum and the product near the inner Mongolia river is excellent.
The fennel mainly contains volatile oil and compounds of the types of phenylpropanoid, flavone, glycoside, fatty oil, phenolic acid and the like, research and development are mainly focused on the volatile oil at present, and component analysis is mainly used, and few reports are made on separation, purification and identification of the compounds, and the compounds are rich in non-volatile components, such as the lack of deep research and development of phenylpropanoid glycosides.
Disclosure of Invention
The invention aims to provide a preparation method of p-propenyl phenol glycoside with whitening effect.
The purpose of the invention is realized in the following way:
the structural formula of the p-propenyl phenol glycoside isThe preparation method comprises the following steps:
(1) Ethanol extraction: crushing a fennel sample 20kg, sieving with a 10-mesh sieve, and extracting with 10L ethanol with volume concentration of 75% under reflux for 5 times, wherein each time is 10L and each time is 2 hours; combining to obtain an extract, and removing the solvent under reduced pressure by a rotary evaporator to obtain a 2.387 kg crude extract A;
(2) And (3) extraction and separation: suspending the crude extract A in water, sequentially extracting with petroleum ether, ethyl acetate and n-butanol for five times, mixing the extractive solutions, and concentrating under reduced pressure to obtain petroleum ether phase, ethyl acetate phase B n-butanol phase and water phase;
(3) And (3) separating and refining: ethyl acetate phase B is subjected to forward silica gel chromatography with 200-300 meshes, and is eluted by a dichloromethane-methanol gradient, wherein the volume ratio of dichloromethane to methanol is 100:1-1:1, fractions were purified by forward silica gel plate with petroleum ether-ethyl acetate 1:1 is developed by developing agent, and R is combined f The fraction Fr.7 with the value of 0.3-0.8 is subjected to forward silica gel chromatography with 100-200 meshes, and is eluted by methylene dichloride-methanol gradient, wherein the volume ratio of the methylene dichloride to the methanol is 50:1-1:1, fractions were run on a forward silica gel plate with dichloromethane-methanol 10:1 is developed by developing agent, and R is combined f The fraction Fr.7.6 and Fr.7.6 with the value of 0.1-0.6 are eluted by reverse phase ODS column chromatography with the methanol-water gradient, the volume ratio of the methanol to the water is 20:80-100:0, and the fraction is eluted by a forward silica gel plate with dichloromethane-methanol 10:1 and 2 drops of formic acid are used as developing agents to develop, and R is combined f The fractions Fr.7.6.2 and Fr.7.6.2 with the values of 0.3-0.4 are separated by Sephadex LH-20 chromatography, and the chromatographic conditions are as follows: methanol, height: 1.5 meters, flow rate: 4 seconds per drop; purifying with semi-prepared liquid phase under the chromatographic condition of acetonitrile-water 15:85; volume flow 3 ml/min; detection wavelength: 365 Purifying at nm to obtain compound 4- (1)E) -1-propen-1-ylphenylβ-DGlucopyranoside [ trans-4- (1-propenyl) -phenol ]β-D-glucopyranoside]Namely, p-propenylphenol glycoside.
The fructus Foeniculi is salt-roasted fructus Foeniculi.
The preparation method of the salt roasted fennel comprises the following steps: adding 100ml of saline into each kilogram of fennel, sealing, soaking for 30min, placing into a stir-frying container, heating with slow fire at 110-120deg.C, stir-frying to slight yellow, taking out, and cooling for use.
The brine is saturated saline.
The application of the p-propenyl phenol glycoside obtained by the preparation method in the preparation of tyrosinase inhibitor products.
A whitening product comprises the p-propenyl phenol glycoside obtained by the preparation method.
The invention has the advantages that:
the invention has the advantage and positive effect of developing a novel preparation method of the p-propenyl phenol glucoside.
The p-propenyl phenol glycoside obtained by the preparation method has tyrosinase inhibition effect and can be used for whitening products.
Drawings
FIG. 1 shows the chemical structure of p-propenylphenol glycoside.
FIG. 2 is a drawing of a para-propenylphenol glycoside 1 H-NMR spectrum.
FIG. 3 is a drawing of a para-propenylphenol glycoside 13 C-NMR (DEPT) spectra.
FIG. 4 is a diagram ofβ-concentration inhibition profile of arbutin against tyrosinase.
FIG. 5 is a graph showing the concentration inhibition of tyrosinase by p-propenylphenol glycoside.
Detailed Description
The invention provides a preparation method of p-propenyl phenol glycoside with whitening effect.
The structural formula of the p-propenyl phenol glycoside isThe preparation method comprises the following steps:
(1) Ethanol extraction: crushing a salt roasted fennel sample 20kg, sieving with a 10-mesh sieve, and extracting under reflux in ethanol with the volume concentration of 75% of 10L for 5 times in 10L each time and 2 hours each time; combining to obtain an extract, and removing the solvent under reduced pressure by a rotary evaporator to obtain a 2.387 kg crude extract A;
(2) And (3) extraction and separation: suspending the crude extract A in water, sequentially extracting with petroleum ether, ethyl acetate and n-butanol for five times, mixing the extractive solutions, and concentrating under reduced pressure to obtain petroleum ether phase, ethyl acetate phase B n-butanol phase and water phase;
(3) And (3) separating and refining: ethyl acetate phase B was chromatographed on 200-300 mesh forward silica gel, eluting with a dichloromethane-methanol (100:1-1:1) gradient, and fractions were purified on a forward silica gel plate on petroleum ether-ethyl acetate 1:1 is developed by developing agent, and R is combined f Fractions fr.7 with a value of 0.3-0.8, fr.7 were chromatographed on 100-200 mesh forward silica gel, eluted with a gradient of dichloromethane-methanol (50:1-1:1), fractions were purified on a forward silica gel plate with dichloromethane-methanol 10:1 is developed by developing agent, and R is combined f The fraction Fr.7.6 and Fr.7.6 with the value of 0.1-0.6 are eluted by the gradient of methanol-water (20:80-100:0) through reversed phase ODS column chromatography, and the fraction is eluted by methylene dichloride-methanol 10 through a forward silica gel plate: 1 and 2 drops of formic acid are used as developing agents to develop, and R is combined f The fractions Fr.7.6.2 and Fr.7.6.2 with the values of 0.3-0.4 are separated by Sephadex LH-20 chromatography, and the chromatographic conditions are as follows: methanol, height: 1.5 meters, flow rate: 4 seconds per drop; purifying with semi-prepared liquid phase under the chromatographic condition of acetonitrile-water 15:85; volume flow 3 ml/min; detection wavelength: 365 Purifying at nm to obtain compound 4- (1)E) -1-propen-1-ylphenylβ-DGlucopyranoside [ trans-4- (1-propenyl) -phenol ]β-D-glucopyranoside]Namely, p-propenylphenol glycoside.
The fructus Foeniculi is salt-roasted fructus Foeniculi.
Preparation of salt-roasted fennel: adding 100ml of saline into each kilogram of fennel, sealing, soaking for 30min, placing into a stir-frying container, heating with slow fire at 110-120deg.C, stir-frying to slight yellow, taking out, and cooling for use.
The brine is saturated saline.
The application of the p-propenyl phenol glycoside obtained by the preparation method in the preparation of tyrosinase inhibitor products.
A whitening product comprises p-propenyl phenol glycoside obtained by the above preparation method.
The invention is further described below without limiting it in any way, and any modifications based on the invention fall within the scope of protection of the invention.
Example 1
Preparation of salt-roasted fennel
Taking salt, adding water, and preparing into saturated solution, namely salt water.
Taking 20kg of common fennel, adding 2000ml of saline, sealing, soaking for 30min, placing into a stir-frying container, heating with slow fire (110-120 ℃) until the color is slightly yellow, taking out, and cooling for standby.
Example 2
Preparation method of p-propenyl phenol glycoside
1.1 materials
Chromatographic silica gel (100-200 mesh, 200-300 mesh, qingdao ocean chemical plant); GF254 thin layer chromatography silica gel (peninsula ocean chemical plant); LH-20 hydroxypropyl dextran gel (Pharmacia, USA); reversed phase C18 column chromatography material (ODS, merck company, germany); thin layer chromatography developer (10% sulfuric acid ethanol solution); methanol, ethanol, acetone, n-butanol, ethyl acetate, methylene dichloride, petroleum ether and other reagents are industrial or chemical pure solvents for heavy evaporation; chromatographic acetonitrile (Shanghai Starfish high purity solvent Co., ltd.).
Fennel medicinal materials are purchased from the new snail bay medicinal material market in 9 months of 2022 and identified as Umbelliferae fennel by Li Hongzhe professor of Yunnan traditional Chinese medicine universityFoeniculum vulgareMill.
1.2 instruments
Bruker Avance III 400 MHz and Bruker DRX 500 MHz superconducting nuclear magnetic resonance apparatus, TMS is an internal standard (Bruker company, germany); high performance liquid chromatograph Agilent model 1200 (Agilent company, usa); ion well time-of-flight mass spectrometer Esquire HCT type (Bruker, germany); analytical balance FA2004 per million (the hun-yu-heng-ping scientific instruments limited); circulating water type multipurpose vacuum pump SHB-III (incorporated by reference, instrument Co., ltd.); sea-time rotary evaporator Hei-VAP Core HL/G (Heidolph, germany).
2. Extraction and separation process
The salt roasted fennel sample 20kg is crushed and sieved by a 10-mesh sieve, and is extracted by reflux in 75% ethanol of 10L for 5 times in 10L each time for 2 hours each time. Mixing the extractive solutions, removing solvent under reduced pressure by rotary evaporator to obtain 2.387 kg crude extract, suspending the crude extract with water, sequentially extracting with petroleum ether, ethyl acetate and n-butanol for five times, mixing the extractive solutions, and concentrating under reduced pressure to obtain petroleum ether phase 203.6g, ethyl acetate phase 73.9 g, n-butanol phase 316.7 g and water phase 759.3 g. The ethyl acetate fraction was chromatographed on forward silica gel (200-300 mesh) with a gradient of dichloromethane-methanol (100:1-1:1), and the fraction was purified on forward silica gel plates with petroleum ether-ethyl acetate 1:1 is developed by developing agent, and R is combined f Fractions fr.7, fr.7 with values between 0.3 and 0.8 were chromatographed on forward silica gel (100-200 mesh) with a gradient of dichloromethane-methanol (50:1-1:1), fractions were eluted on forward silica gel plate with dichloromethane-methanol 10:1 is developed by developing agent, and R is combined f The fraction Fr.7.6 and Fr.7.6 with the value of 0.1-0.6 are eluted by the gradient of methanol-water (20:80-100:0) through reversed phase ODS column chromatography, and the fraction is eluted by methylene dichloride-methanol 10 through a forward silica gel plate: 1 and 2 drops of formic acid are used as developing agents to develop, and R is combined f Separating the fraction Fr.7.6.2 with a value of 0.3-0.4, fr.7.6.2 by Sephadex LH-20 chromatography (methanol, height: 1.5 m, flow rate: 4 seconds per drop), purifying with semi-preparative liquid phase (acetonitrile-water 15:85; volume flow rate: 3 ml/min; detection wavelength: 365 nm), purifying to obtain compound 4- (1)E) -1-propen-1-ylphenylβ-DGlucopyranoside [ trans-4- (1-propenyl) -phenol ]β-D-glucopyranoside（9.9 mg）]Namely, the p-propenyl phenol glycoside, the chemical structure of the compound is shown in figure 1, and figure 2 is a 1H-NMR spectrum of the p-propenyl phenol glycoside. FIG. 3 is a 13C-NMR (DEPT) spectrum of p-propenylphenol glycoside.
Physical and chemical constants and spectrum data of p-propenyl phenol glucoside
White powdery crystals (methanol); the molecular formula: c (C) 15 H 20 O 6 HR-ESI-MS，m/z 319.1152 [M+Na] + (calculated: 319.1152). 1 H-NMR（400MHz，CD 3 OD）δ H ：6.36（1H，d，J= 15.8Hz，H-7），6.15（1H，dq，J= 15.8，6.5Hz，H-8），3.80（6H，m，H-2′，3′，4′，5′，6′），1.85（3H，d，J= 6.6Hz，H-9）. 13 C-NMR（100MHz，CD 3 OD）δ C ：158.1（s，C-4），133.8（s，C-1），131.6（d，C-7），127.8（d，C-2，6），124.8（d，C-8），117.8（d，C-3，5），102.4（d，C-1′），78.1（d，C-3′），77.9（d，C-5′），74.9（d，C-2′），71.4（d，C-4′），62.5（t，C-6′），18.5（q，C-9）。
Example 3
Studies of the effects of anti-tyrosinase Activity
The method is modified on the basis of the reference. (Li ZY, zhao P, song SJ, huang XX. Chiral resolution of racemic phenylpropanoids with tyrosinase inhibitoryactivities from the fruits of Crataegus pinnatifida Bge J Food biochem. 2022 Oct;46 (10): e 14304.).
1. Materials and instruments
1.1 Material
Tyrosinase (Sigma-Aldrich Co.); l-tyrosine (Shanghai Miclin Biochemical technology Co., ltd.)βArbutin (Shanghai Yuan leaf Biotechnology Co., ltd.).
1.2 Instrument for measuring and controlling the intensity of light
Synergy2 multifunctional enzyme labeling instrument (BIOTEK, usa).
Tyrosinase inhibition activity assay
2.1 preparation of solutions
2.1.1 preparation of phosphate buffer
Precisely measuring 20 ml of 10 XPBS buffer solution, diluting to 200 ml by ultrapure water, and finally adjusting the pH to a specified range (6.5-7.5) by using 0.2 mol/L sodium hydroxide to obtain the PBS buffer solution.
Preparation of tyrosinase test solution
Precisely transferring 100 units/ml tyrosinase (SLCN 1560) 9 ml packaged in advance, adding PBS buffer solution, diluting to 30 ml to obtain 30 units/ml tyrosinase test solution, and placing the test solution into a refrigerator at-20deg.C for use.
Preparation of tyrosine solution
Precisely weighing 5 mg L-tyrosine (batch number: C14856769) powder, adding 50 ml PBS buffer into 100ml EP tube, shaking to obtain 0.1 mg/ml L-tyrosine solution, and standing for use.
Sample solution configuration
(1) Preparation of Positive drug solution
Precise weighingβ-arbutin (batch number: T17S6B 1) powder 4 mg, adding 30 ul DMSO to dissolve completely, precisely adding 970 ul PBS by using a pipette to obtain 4 mg/ml positive reagent solution, and sequentially carrying out gradient dilution on the positive reagent to obtain 2 mg/ml positive reagent, 1mg/ml positive reagent, 0.5 mg/ml positive reagent and 0.25 mg/ml positive reagent for later use.
(2) Configuration of sample solution to be tested
Accurately weighing a proper amount of the p-propenyl phenol glycoside prepared in the example 2, adding 30 ul of DMSO to completely dissolve the p-propenyl phenol glycoside, and accurately adding PBS to sequentially obtain the concentrations of 1mg/ml, 0.5 mg/ml, 0.25 mg/ml, 0.125 mg/ml and 0.0625 mg/ml for later use.
Determination of inhibition ratio of tyrosinase Activity
Sequentially adding PBS buffer solution, compound test solutions with different concentration gradients, arbutin control solution with different concentration gradients and tyrosinase solution into a 96-well plate by using a pipetting gun according to the volume of a table 1, incubating for 10 min at 37 ℃, adding an L-tyrosine test solution, incubating for 30min under the same condition, immediately placing a multifunctional enzyme-labeled instrument into 492nm to measure the absorbance of the solution after incubation is finished, recording data, making 3 parallel groups for each concentration experiment, and calculating the inhibition rate of the compound to tyrosinase by using the average value of the 3 groups of data according to the following formula:
inhibition ratio = [1- (A) T -A B ）/（A C -A N ）]×100%
Wherein T is the reaction liquid group added with the sample and tyrosine; b, the reaction liquid group which is added with a sample and is not added with tyrosine; c, the reaction liquid group which is not added with a sample and is added with tyrosine; and N is the reaction liquid group without adding the sample and without adding tyrosine. A is that T The absorbance value of the T group reaction solution measured at 492 nm; a is that B The absorbance value of the group B reaction solution measured at 492 nm; a is that C The absorbance value of the group C reaction solution measured at 492 nm; a is that N The absorbance values of N groups of reaction solutions were measured at 492 nm.
TABLE 1 composition of reaction solution
| Sample (ul) | PBS（ul） | Tyrosinase (ul) | Tyrosine (ul) | Total amount (ul) | |
| T | 40 | 40 | 40 | 120 | |
| B | 40 | 40 | 40 | 120 | |
| C | 40 | 40 | 40 | 120 | |
| N | 80 | 40 | 120 |
2.3 results of tyrosinase inhibition experiments
Positive drugβThe result of the concentration inhibition of the arbutin on the tyrosinase activity is shown in figure 4, and the inhibition rate is 62.79% from high to low; 50.24%;41.48%;33.19%;18.73%, wherein the inhibition rate of the positive medicine to tyrosinase is improved along with the increase of the concentration of the test solution, the inhibition rate of the positive medicine is increased more rapidly along with the increase of the concentration when the concentration is less than 1mg/ml, and the inhibition rate of the positive medicine is increased more slowly along with the increase of the concentration when the concentration is more than 1mg/ml, which is expressed as concentration-dependent inhibition, and the IC thereof 50 The value was 1.784 mg/ml.
The concentration inhibition result of the compound on tyrosinase activity is shown in FIG. 5, and the inhibition rate is from high to lowThe secondary is 54.58%;48.83%;42.05%;35.24%;28.24%, the inhibition rate of tyrosinase is also improved along with the increase of the concentration of the tested liquid, the inhibition rate is faster along with the increase of the concentration when the concentration of the compound is below 0.5 mg/ml, the growth rate is slower when the concentration is more than 0.5 mg/ml, the inhibition is shown as concentration-dependent inhibition, and the IC is shown as the inhibition of the concentration 50 The value was 0.575 mg/ml.
Analysis of results
The inhibition rate experiment result shows that the inhibition rate of tyrosinase is 54.58% when the concentration of the compound is 1mg/ml, and the positive medicineβThe inhibition rate of arbutin is only 41.48%, and the compound IC 50 The value is 0.575 mg/ml, and is a positive medicineβ-arbutin (IC) 50 A value of 1.784 mg/ml) indicates that the compound inhibits tyrosinase activity far more thanβ-arbutin with better whitening effect. The results show that the compound has better whitening activity on propenyl phenol glycoside than the positive medicine. The phenylpropanoid compound is separated from fennel for the first time, and has a good research prospect.
Claims (5)
1. A preparation method of p-propenyl phenol glycoside is characterized in that the structural formula of the p-propenyl phenol glycoside is as followsThe preparation method comprises the following steps:
(1) Ethanol extraction: crushing a fennel sample 20kg, sieving with a 10-mesh sieve, and extracting with 10L ethanol with volume concentration of 75% under reflux for 5 times, wherein each time is 10L and each time is 2 hours; combining to obtain an extract, and removing the solvent under reduced pressure by a rotary evaporator to obtain a 2.387 kg crude extract A;
(2) And (3) extraction and separation: suspending the crude extract A with water, sequentially extracting with petroleum ether, ethyl acetate and n-butanol for five times, mixing the extractive solutions, and concentrating under reduced pressure to obtain petroleum ether phase, ethyl acetate phase B, n-butanol phase and water phase;
(3) And (3) separating and refining: subjecting ethyl acetate phase B to 200-300 mesh forward silica gel chromatography, eluting with dichloromethane-methanol gradient, and collecting the volume of dichloromethane-methanolThe ratio is 100:1-1:1, fractions were purified by forward silica gel plate with petroleum ether-ethyl acetate 1:1 is developed by developing agent, and R is combined f The fraction Fr.7 with the value of 0.3-0.8 is subjected to forward silica gel chromatography with 100-200 meshes, and is eluted by methylene dichloride-methanol gradient, wherein the volume ratio of the methylene dichloride to the methanol is 50:1-1:1, fractions were run on a forward silica gel plate with dichloromethane-methanol 10:1 is developed by developing agent, and R is combined f The fraction Fr.7.6 and Fr.7.6 with the value of 0.1-0.6 are eluted by reverse phase ODS column chromatography with the methanol-water gradient, the volume ratio of the methanol to the water is 20:80-100:0, and the fraction is eluted by a forward silica gel plate with dichloromethane-methanol 10:1 and 2 drops of formic acid are used as developing agents to develop, and R is combined f The fractions Fr.7.6.2 and Fr.7.6.2 with the values of 0.3-0.4 are separated by Sephadex LH-20 chromatography, and the chromatographic conditions are as follows: methanol, height: 1.5 meters, flow rate: 4 seconds per drop; and then semi-prepared liquid phase purification is carried out, wherein the chromatographic conditions are acetonitrile-water 15:85, volume flow rate is 3 ml/min, and detection wavelength is as follows: 365 nm, purifying to obtain the compound p-propenyl phenol glycoside.
2. The preparation method of claim 1, wherein the fennel is a salt-roasted fennel, and the preparation method comprises: adding 100ml of saline into each kilogram of fennel, sealing, soaking for 30min, placing into a stir-frying container, heating with slow fire at 110-120deg.C, stir-frying to slight yellow, taking out, and cooling for use.
3. The method according to claim 2, wherein the brine is saturated brine.
4. Use of the p-propenylphenol glycoside obtained by the process of claim 1 in the preparation of tyrosinase inhibitor products.
5. A whitening product characterized by comprising the p-propenylphenol glycoside obtained by the production process of claim 1.
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