CN108864004A - The purposes of the rich volt lactone of hydroxyl dihydro and its derivative in purslane - Google Patents
The purposes of the rich volt lactone of hydroxyl dihydro and its derivative in purslane Download PDFInfo
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- CN108864004A CN108864004A CN201811177961.4A CN201811177961A CN108864004A CN 108864004 A CN108864004 A CN 108864004A CN 201811177961 A CN201811177961 A CN 201811177961A CN 108864004 A CN108864004 A CN 108864004A
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- lactone
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- purslane
- hydroxyl
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 46
- 150000002596 lactones Chemical class 0.000 title claims abstract description 43
- 235000001855 Portulaca oleracea Nutrition 0.000 title claims abstract description 28
- 241000219304 Portulacaceae Species 0.000 title claims abstract description 28
- 239000003814 drug Substances 0.000 claims abstract description 14
- 229940079593 drug Drugs 0.000 claims abstract description 10
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 9
- 230000004112 neuroprotection Effects 0.000 claims abstract description 8
- 230000036541 health Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 12
- -1 gamma lactone class compound Chemical class 0.000 abstract description 12
- 238000000605 extraction Methods 0.000 abstract description 10
- 238000000926 separation method Methods 0.000 abstract description 10
- 238000011160 research Methods 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 4
- VJZWZDQDXPADSE-UHFFFAOYSA-N 5-hydroxy-3,4-dimethyl-5-pentylfuran-2-one Chemical compound CCCCCC1(O)OC(=O)C(C)=C1C VJZWZDQDXPADSE-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002547 new drug Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000009509 drug development Methods 0.000 abstract description 2
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- 238000000034 method Methods 0.000 description 24
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- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 5
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000003698 anagen phase Effects 0.000 description 3
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- 239000002024 ethyl acetate extract Substances 0.000 description 3
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- 238000005259 measurement Methods 0.000 description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000007781 pre-processing Methods 0.000 description 3
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- 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
- 241000196324 Embryophyta Species 0.000 description 2
- 235000002710 Ilex cornuta Nutrition 0.000 description 2
- 241001310146 Ilex cornuta Species 0.000 description 2
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- 229920005654 Sephadex Polymers 0.000 description 2
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- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000001026 1H--1H correlation spectroscopy Methods 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 206010003399 Arthropod bite Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010007247 Carbuncle Diseases 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 201000000297 Erysipelas Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 206010017553 Furuncle Diseases 0.000 description 1
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
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- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- 230000036772 blood pressure Effects 0.000 description 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
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- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000002072 distortionless enhancement with polarization transfer spectrum Methods 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 238000001425 electrospray ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 208000003512 furunculosis Diseases 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 208000035861 hematochezia Diseases 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 1
- 238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- 229930014626 natural product Natural products 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical group CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
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- 230000035755 proliferation Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 150000003431 steroids Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Polymers & Plastics (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Botany (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Neurology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to the purposes of the rich volt lactone of hydroxyl dihydro in traditional Chinese medicine extraction, separation field more particularly to purslane and its derivative.The rich volt lactone of the hydroxyl dihydro, molecular formula C11H18O3, it is named as 5- hydroxyl -3,4- dimethyl -5- pentyl -2(5H)Furanone.It is extracted from purslane and isolates alpha-beta-unsaturation gamma lactone class compound:The rich volt lactone of hydroxyl dihydro; it has anti-inflammatory and neuroprotection; the rich volt lactone of hydroxyl dihydro of the present invention and its derivative can be used as the raw material of other compound synthesis primers and new drug development and pharmacology activity research, be used to prepare anti-inflammatory and drug or health care product of neuroprotection.
Description
Technical field
The present invention relates to the rich volt lactone of hydroxyl dihydro in traditional Chinese medicine extraction, separation field more particularly to purslane and its derivatives
The purposes of object.
Background technique
Purslane(Portulaca oleraceaL.)Also known as long life dish, horse three-coloured amaranth, it is portulacaceous plant.Purslane
Drought-enduring waterlogging and fast light shade tolerant, widely distributed, resourceful, the wild plant as dual-purpose of drug and food is concerned, and 2015 editions
《Pharmacopoeia of People's Republic of China》In record the dry aerial parts of purslane and be used as medicine, there is clearing heat and detoxicating, cooling blood and hemostasis, stop dysentery
And other effects, for toxic-heat and blood stasis, carbuncle swells furunculosis, eczema, erysipelas, snakebite and bugbite, hematochezia, hemorrhoid blood, metrostaxis etc..
Purslane modern pharmacology research shows it with anti-inflammatory analgesic, anti-bacteria and anti-virus, lowering blood pressure and blood fat, antioxygen
Change, anticancer, relaxation skeletal muscle and smooth muscle adjust the effects of immune function.Research shows that the numerous chemical components of purslane are it
The pharmacological action of multiplicity provides material base, and purslane main chemical compositions include flavonoids, cumarin, terpene, steroid, life
Alkaloids, amino acid, various pigments and minerals class etc..In recent years, many scholars, which concentrate on, contains purslane chemical component
It is fixed to measure, the research such as pharmacodynamics and pharmacokinetics, however, from having no alpha-beta-unsaturation gamma lactone class chemical combination in purslane
The separation of object and inside and outside analysis and research report.
Summary of the invention
In view of the above-mentioned problems, the present invention provides a kind of rich volt lactone of the hydroxyl dihydro extracted from purslane, sent out through research
Now the unsaturated lactone compound has the function of anti-inflammatory and protection nerve;A kind of extraction for the compound point is provided simultaneously
From method, this method is easy, compound purity quickly, environmentally friendly and isolated is high.
To achieve the above object, the present invention the rich volt lactone of hydroxyl dihydro in purslane is provided and its derivative be used to prepare it is anti-
Scorching or neuroprotection drug or health care product.
The rich volt lactone of the hydroxyl dihydro extracted in purslane(hydroxydihydrobovolide), molecular formula is
C11H18O3, chemical structural formula is.
To achieve the above object, the present invention also provides a kind of extraction separation sides of the rich volt lactone of hydroxyl dihydro in purslane
Method, the specific steps are.
Step 1 takes the dry medicinal material of purslane, is extracted using 50% alcohol reflux, ethyl alcohol is recovered under reduced pressure, is cooled to room temperature, obtains
To medical fluid.
Step 2, by step 1 herb liquid, using the method for Static Adsorption by AB-8 type macroreticular resin, successively using water,
50% ethyl alcohol and 70% ethanol gradient elution, after 70% alcohol elution is concentrated under reduced pressure, concentrate ethyl acetate extracts repeatedly
It takes, ethyl acetate is recovered under reduced pressure to medicinal extract, obtains acetic acid ethyl ester extract.
Step 3 separates acetic acid ethyl ester extract in step 2 through polyamide column, using alcohol-water gradient elution, 70% second
Alcohol part upper silicagel column after being evaporated, successively uses acetate-methanol gradient elution, obtains 100 fractions, fraction 70-100 is taken to subtract
Pressure concentration, obtains concentrate.
Step 4, by step 3 gained concentrate, pretreated ODS column(Octadecylsilyl, octadecylsilane
Bonded silica gel filler)Chromatography obtains 10 parts with methanol-water isocratic elution.
Step 5, by step 4 gained part in 6 and 7 sample segments, pretreated Sephadex LH-20(Hydroxypropyl
Sephadex)Processing, is eluted with methanol, and the hydroxyl dihydro finally obtained from purslane wins volt lactone.
The volumetric usage of 50% ethyl alcohol is 10 times of medicinal material in the step 1.
The number that ethyl acetate extracts repeatedly in the step 2 is 3 times, the volumetric usage of each ethyl acetate and concentrate
Ratio be 1:1.
Isocratic elution in the step 4 is that methanol-water volume ratio is 70:30 isocratic elution.
The preprocessing process of the ODS and Sephadex LH-20 gel is that methanol impregnated 24 hours, and upper prop uses methanol
It is washed till to instill in water and balance each other without muddiness, then with initial flow.
Beneficial effects of the present invention.
In the present invention, purslane alcohol extract is separated, is purified, and isolated 5- hydroxyl -3,4- diformazan for the first time
Base -5- pentyl -2(5H)The rich volt lactone of furanone, i.e. hydroxyl dihydro, the separation of the rich volt lactone of the purslane hydroxyl dihydro
It is not reported by existing paper periodical with pharmacology activity research;The present invention provides the rich volt lactone of hydroxyl dihydro from purslane
And a kind of extraction separation method for noval chemical compound of the present invention, it is successively extracted using 50% alcohol reflux, macroporous absorbent resin layer
Analysis, ethyl acetate extraction, polyamide column chromatography, silica gel column chromatography, Sephadex LH-20 is purified, compression leg isolates and purifies in ODS,
Successful extract isolates the rich volt lactone of hydroxyl dihydro, and this method operating procedure is only five steps, and operating method is easy and quick;It extracts
Separation process mainly uses the extraction of 50% ethyl alcohol and ethyl acetate extraction, process environmental protection;And the change isolated through this method
Close that object purity is higher is all larger than 90%;Since the rich volt lactone of hydroxyl dihydro belongs to alpha-beta-unsaturation gamma lactone class compound and has
Significant anti-tumor activity and HIV-resistant activity, therefore, research shows that the compound has anti-inflammatory and neuroprotection, the present invention
The rich volt lactone of hydroxyl dihydro and its derivative can be used as other compound synthesis primers and new drug development and pharmacology is living
The raw material of Journal of Sex Research also can be used for preparing anti-inflammatory and neuroprotection drug.
Detailed description of the invention.
Fig. 1 is the high resolution mass spectrum figure of the rich volt lactone of hydroxyl dihydro of the present invention.
Fig. 2 is the rich volt lactone of hydroxyl dihydro of the present invention1H-NMR spectrogram.
Fig. 3 is the rich volt lactone of hydroxyl dihydro of the present invention13C-NMR spectrogram.
Fig. 4 is the carbon-13 nmr spectra of the rich volt lactone of hydroxyl dihydro of the present invention(DEPT)Spectrogram.
Fig. 5 is the nuclear magnetic resonance of the rich volt lactone of hydroxyl dihydro of the present invention1H-1H COSY spectrogram.
Fig. 6 is the nuclear magnetic resonance HMBC spectrogram of the rich volt lactone of hydroxyl dihydro of the present invention.
Fig. 7 is the nuclear magnetic resonance HSQC spectrogram of the rich volt lactone of hydroxyl dihydro of the present invention.
Fig. 8 is the nuclear magnetic resonance NOESY spectrogram of the rich volt lactone of hydroxyl dihydro of the present invention.
Specific embodiment
Embodiment 1.
The present embodiment provides a kind of rich volt lactone of hydroxyl dihydro, molecular formula C11H18O3, chemical structural formula is.
The rich volt lactone of the hydroxyl dihydro is named as 5- hydroxyl -3,4- dimethyl -5- pentyl -2 according to structure(5H)Furans
Ketone, table 1. are the nuclear magnetic data of the unsaturated lactone compound:1H-NMR with13C-NMR is in CDCl3In.
Compound:Light yellow oil;HR-ESI-TOF-MS provides m/z: 199.1321 [M+H]+Quasi-molecular ion
Peak(See Fig. 1), molecular weight 198.1404;In conjunction with1H-NMR,13C-NMR and DEPT data(See Fig. 2-4), thus it is speculated that the chemical combination
The possible molecular formula of object is C11H18O3, degree of unsaturation 3;Spectroscopic data is as follows,1H-NMR(500MHz, CDCl3)δ:1.96
(1H, br, H-6a), 1.93(3H, d, J=0.75Hz, H-11), 1.81(3H, d, J=0.85 Hz, H-12), 1.77(1H, br, H-
6b), 1.29(2H, m, H-8, -9), 1.27(2H, m, H-7), 1.17(1H, br, OH), 0.88(3H, t, J=6.3 Hz, H-
10).13C-NMR(100 MHz, CDCl3)δ:172.18(C-2), 157.80(C-4), 125.28(C-3), 107.02(C-5),
35.99(C-6), 31.55(C-7), 22.59(C-8), 22.42(C-9), 13.91(C-10), 10.69(C-11), 8.42(C-
12);1H-NMR,13C-NMR and DEPT spectrum shows a total of 11 carbon signals, including 3 methyl(C-10, -11, -12), four
Mesomethylene carbon(C-6, -7, -8, -9)With 4 quaternary carbons.Wherein according to chemical shift, 4 quaternary carbons can be speculated as 1 ester carbonyl group respectively
Carbon(C-2), 2 alkenyl quaternary carbons(C-3, -4)Replace quaternary carbon with a double heteroatoms(C-5).Further combined with two-dimentional H-HCOSY,
HMQC, HMBC and NOESY spectrum analysis can carry out full ownership to the hydrocarbon signal of compound(See Fig. 5-8).HMBC spectrum display is following several
Group data:H-11 and C-3, C-4, C-5, C-12;H-12 and C-2, C-3, C-4, C-11;H-10 and C-8, C-9;H-8, H-9, H-
10 and C-7;H-8, H-9 and C-10;H-8 and C-9, H-9 and C-8;The coupling of wherein H-11 and C-4, H-12 and C-3 are strong
Illustrate that two methyl are connected directly with C-4, C-3 respectively.According to H-H Correlated Spectroscopy it is found that δ 1.29 and δ 0.87 in four methylene
Adjacent, δ 1.27 is adjacent with δ 1.29, and δ 1.93 is adjacent with δ 1.81.Above data combination degree of unsaturation shows depositing for furan ring structure
There is adjacent methyl substitution on, C-3, the position C-4, and C-5 is connect with pentyl carbochain.C-5(107.02)Chemical shift
It is mobile to low field, prompt hydroxyl and pentyl on its position to replace simultaneously.NOE correlation includes following groups data:H-6a with
H-6b;H-8, H-9 and H-10;H-11 and H-12;H-7 is related to the active hydrogen in H-10 and hydroxyl.Above data and document report
Road is almost the same, therefore compound is determined as 5- hydroxyl -3,4- dimethyl -5- pentyl -2(5H)Furanone(The rich volt of hydroxyl dihydro
Lactone).
The present embodiment also provides the extraction separation method of above compound, the specific steps are.
Step 1:The dry medicinal material 80kg of purslane is weighed, is extracted using 50% alcohol reflux, 50% ethanol consumption is medicinal material
10 times, twice, ethyl alcohol is recovered under reduced pressure in each 2h to refluxing extraction, cools to room temperature, obtains medical fluid, spare.
Step 2:Gained medical fluid in step 1 is successively used using the method for Static Adsorption by AB-8 type macroreticular resin
Water, 50% ethyl alcohol, 70% ethanol gradient elution, after 70% alcohol elution is concentrated under reduced pressure, concentrate ethyl acetate extracts repeatedly
It takes 3 times, 40 DEG C or less are recovered under reduced pressure ethyl acetate to medicinal extract, obtain acetic acid ethyl ester extract.
Step 3:Acetic acid ethyl ester extract in step 2 is separated through polyamide column, using alcohol-water(0/100,30/70,
50/50,70/30,90/10, v/v)Gradient elution, 70% ethanolic moiety separate after being evaporated through silica gel column chromatography, and wherein silica gel is
200-300 mesh, successively uses acetate-methanol(10:1,5:1,1:1, v:v)Gradient elution is obtained 100 fractions, takes stream
Part 70-100 is concentrated under reduced pressure, and obtains medicinal extract 7g.
Step 4:Will in step 3 concentration gained 70% methanol of medicinal extract dissolve, and with 15000r centrifugal treating 5min after, take
Supernatant, pretreated ODS medium pressure column chromatography separation, wherein filler particle size is 20-40 μm, uses methanol-water(70:30, v/v)
Isocratic elution(Pressurization, makes flow velocity 1mL/min, temperature is room temperature), obtain 10 parts(Elute to obtain 10 bottles, every bottle
50mL).
Step 5:10 parts of gained are set to examine under ultraviolet lamp (365nm) and be known through thin-layer chromatography in step 4,6,7 two positions
There is obvious identical fluorescence spot, by 6,7 parts pretreated Sephadex LH-20 again(Hydroxypropyl sephadex)Place
Reason, is eluted with methanol, is received respectively with several bottles, and the light yellow oil chemical combination for deriving from purslane is finally obtained
Object (16mg).
The preprocessing process of the Sephadex LH-20 gel is that methanol impregnated for 24 hours, and upper prop is washed till instillation with methanol
Without muddiness in water, then balanced each other with initial flow.Through ultra performance liquid chromatography, normalization method measures purity 90-99%.The ODS's
Preprocessing process is that methanol impregnated for 24 hours, upper prop, is washed till to instill in water with methanol and be balanced each other without muddiness, then with initial flow.
One, the anti-inflammatory effect of the rich volt lactone of hydroxyl dihydro.
1, main material.
1.1, drug and reagent:It tests the rich volt lactone of hydroxyl dihydro used to be prepared by the above method, purity 90-99%, essence
It is close to weigh, solution needed for being diluted to following each dosage groups with DMSO.DMEM high glucose medium, fetal calf serum(U.S. Hyclone is public
Department);Penicillin, streptomysin(Hangzhou Chinese holly company);LPS(Sigma Co., USA);IL-6,TNF-α,PGE2ELISA examination
Agent box(Cayman company of the U.S.);Cell pyrolysis liquid, Griess reagent(Green skies Bioisystech Co., Ltd)
1.2 cell strain:RAW264.7 macrophage(U.S.'s ATCC cell bank).
1.3 grouping:It is divided into control group, LPS group and experimental group, each one group.
2 experimental methods.
The fetal calf serum of l0%, l% antibiotic are added in DMEM high glucose medium for 2.1 RAW264.7 macrophage cultures
(100U/mL penicillin and 100 μ g/mL streptomysins), are placed in 37 DEG C, 5% CO2It is cultivated in incubator.
2.2 MTT colorimetric method for determining cell viabilities, above-mentioned three groups respectively logarithmic growth phase RAW264.7 macrophage connect
For kind in 96 well culture plates, cell density is 1 × 104A/mL, every 100 μ L of hole, 37 DEG C of temperature, 5%CO2Under the conditions of overnight incubation
Afterwards, the rich volt lactone of the present embodiment hydroxyl dihydro of various concentration is added in experimental group(1-100μM), after being incubated for 1h, to LPS group and reality
The LPS that group is separately added into final concentration of 1 μ g/mL is tested, zeroing group is separately set(The culture solution of the solvent containing DMSO), every group sets 3 multiple holes,
Investigate the influence being added after drug to cell.After above-mentioned group of cells culture for 24 hours, 5 mg/mL MTT are added in each hole cell
20 μ L, 37 DEG C of temperature, 5%CO2Under the conditions of, continue after being incubated for 4h, terminate culture, inhale and abandon liquid in hole, 100 μ L bis- are added in every hole
Methyl sulfoxide(DMSO), 10min is vibrated, makes to crystallize sufficiently dissolution into the cell, each hole extinction of measurement at microplate reader 570nm wavelength
Value.
2.3 utilize Ge Lisi(Griess)Method measures the content of NO, investigates the present embodiment new alkaloids compound to LPS
The inhibiting effect of the NO yield of the mouse macrophage RAW264.7 of induction.After mouse macrophage RAW264.7 passage,
It is cultivated in the sugared cell culture medium DMEM of height containing 10% fetal calf serum, the present embodiment hydroxyl dihydro of various concentration is added in experimental group
Rich volt lactone(1-20μM), at 37 DEG C, 5%CO2Under the conditions of be incubated for 1h after, use LPS(Final concentration of 1 μ g/mL)Induce inflammation anti-
It answers, collects supernatant afterwards for 24 hours, every group of processing repeats 3 holes.Griess method measures the content of NO in cell supernatant, according to difference
Influence of the rich volt lactone of concentration the present embodiment hydroxyl dihydro to the LPS RAW264.7 cell release NO induced, to reflect NO water
It is flat.
2.4 ELISA methods measure inflammatory factor IL-6, TNF-α and inflammatory mediator PGE2:By logarithmic growth phase RAW264.7
Macrophage is inoculated in 24 well culture plates, and cell density is 1 × 105A/mL, every hole 1mL, 37 DEG C of temperature, 5% CO2Under the conditions of
The rich volt lactone of hydroxyl dihydro of the present invention is added in overnight incubation, experimental group(1-20μM), after cultivating 1h, LPS is added in every hole(It is dense eventually
Degree is 1 μ g/mL), it is incubated for altogether for 24 hours, every group of processing repeats 3 holes.ELISA method measures purslane source hydroxyl dihydro and wins Fu Neizhichu
IL-6, TNF-α and the PGE of RAW264.7 macrophages secrete after reason2Content.
3 experimental results
The experimental results showed that the rich volt lactone of the present embodiment hydroxyl dihydro is to the proliferation of the LPS macrophage RAW264.7 induced without shadow
It rings, it is safe and non-toxic;And can be effectively suppressed LPS induction macrophage RAW264.7 produced by excess inflammatory cytokine IL-6,
TNF-α and inflammatory mediator NO, PGE2, and be in concentration dependant.
Comparative survival rate of cells experimental result is as shown in table 2..
Note:*P<0.05 compared with the control group(High concentration group has significant difference),
Utilize Ge Lisi(Griess)The content experimental result of method measurement NO is shown in Table 3..
Note:*P<0.05 compared with the control group,#P<0.05 compared with LPS group.
ELISA method measures inflammatory factor IL-6, TNF-α and inflammatory mediator PGE2As a result as shown in table 4..
Note:*P<0.05 compared with the control group,#P<0.05 compared with LPS group.
Two, the neuroprotection of the rich volt lactone of hydroxyl dihydro.
1 main material.
1.1 drugs and reagent:It tests the rich volt lactone of hydroxyl dihydro used to be prepared by the above method, purity 90-99%, essence
It is close to weigh, solution needed for being diluted to following each dosage groups with DMSO.DMEM high glucose medium, fetal calf serum(U.S. Hyclone is public
Department);Penicillin, streptomysin(Hangzhou Chinese holly company), phosphate buffer(PBS),(Wuhan doctor's moral Co., Ltd), ROS
Detection kit(The green skies Reagent Company in Haimen)
1.2 cell strain:Human neuroblastoma cells' strain(SH-SY5Y,IMR-32)(Chinese Academy of Sciences's Shanghai cell
1.3 grouping:It is divided into control group, H2O2Damage model group and experimental group.
2 experimental methods.
The fetal calf serum of l0%, l% antibiotic are added in DMEM high glucose medium for 2.1 people's neuroblast cultures
(100U/mL penicillin and 100 μ g/mL streptomysins), are placed in 37 DEG C, 5%CO2It is cultivated in incubator.
2.2 MTT colorimetric method for determining cell viabilities, above-mentioned three groups of difference logarithmic growth phase SH-SY5Y cell and IMR-32
For cell inoculation in 96 well culture plates, cell density is 1 × 104A/mL, every 100 μ L of hole, 37 DEG C of temperature, 5%CO2Under the conditions of train
After supporting overnight, the rich volt lactone of hydroxyl dihydro of the present invention of various concentration is added in experimental group(5-40μM), it is incubated for after 1h to H2O2Group and
Experimental group is separately added into the H of final concentration of 800 μM/L2O2, separately set zeroing group(The culture solution of the solvent containing DMSO), every group sets 3 again
The influence being added after drug to cell is investigated in hole.After above-mentioned group of cells culture for 24 hours, 5 mg/mL are added in each hole cell
MTT 20 μ L, 37 DEG C of temperature, 5%CO2Under the conditions of continue after being incubated for 4h, terminate culture, inhale and abandon liquid in hole, 100 μ L are added in every hole
Dimethyl sulfoxide(DMSO), 10min is vibrated, makes to crystallize sufficiently dissolution into the cell, each hole of measurement is inhaled at 450 nm wavelength of microplate reader
Light value(A)Value, calculating cell survival rate, cell survival rate=(AH2O2Damage-ABlank)/(AControl-ABlank).
2.3 DCFH-DA methods detect SH-SY5Y cell and the intracellular ROS of IMR-32, after group of cells gives respective substance
It is incubated for for 24 hours, incubation terminates preceding 30min, and each hole is added DCFH-DA, makes final concentration of 10 μm of ol/L, continue to be incubated in 37 DEG C
30min collects cell, and PBS is washed 2 times, and the cell suspension of same concentrations is made in group of cells by cell count.Take 100 μ L cells
Suspension fluorescence intensity, excitation wavelength 485nm, launch wavelength 538nm.With control group fluorescence intensity for 100%, remaining each group
Compared with control group fluorescence intensity, ROS variation intracellular is calculated.
2.4 INT chromogenic reaction methods measure the burst size of LDH, remove above-mentioned control group, H2O2Damage model group and experimental group
Outside, blank control group is separately set up(Blank control group not inoculating cell), group of cells be added respective substance culture for 24 hours, take each hole
For 120 μ L of supernatant into 96 new orifice plates, the LDH detection working solution for adding 60 μ L to prepare is protected from light incubation at room temperature 30min, at 490nm
It is measured with multi-function microplate readerAValue calculates the LDH burst size percentage relative to control tube.LDH release rate=(AAdministration-A
Blank)/(AControl-ABlank).
3 experimental results.
Comparative survival rate of cells experimental result is as shown in table 5..
Note:*P<0.05 and H2O2Damage model group compares.
SH-SY5Y cell and the intracellular ROS amount testing result of IMR-32 are as shown in table 6..
Note:*P<0.05 compared with the control group,#P<0.05 and H2O2Damage model group compares.
SH-SY5Y cell and the influence result of the intracellular LDH release of IMR-32 are as shown in table 7..
Note:*P<0.05 compared with the control group,#P<0.05 and H2O2Damage model group compares.
In conclusion the present invention provides the rich volt lactone of hydroxyl dihydro and its extraction separation method, successively returned using 50% ethyl alcohol
Flow extractions, macroporous adsorption resin chromatography, ethyl acetate extraction, polyamide column chromatography, silica gel column chromatography, in ODS compression leg separate,
Sephadex LH-20 purifying, successfully isolated hydroxyl dihydro is rich for the first time from purslane lies prostrate lactone, and this method is easy, fastly
Speed, environmental protection, and it is higher through the isolated compound purity of this method, it extracts, has from conventional Chinese medicine purslane
Anti-inflammatory, neuroprotection, therefore the rich volt lactone of hydroxyl dihydro of the present invention and its derivative can be used as in natural products exploitation
Medicine new drug, has broad prospects.
Claims (1)
1. the rich volt lactone of hydroxyl dihydro and its derivative in purslane are used to prepare anti-inflammatory and neuroprotection drug or health care
Product.
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CN115716790B (en) * | 2022-12-13 | 2023-06-02 | 辽宁中医药大学 | Extraction and separation method of amide ester alkaloid in purslane and application of extraction and separation method |
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