CN110128562A - A kind of antitumor Psoralen lipopolysaccharides and its extraction separation method and the application in terms of preparing anti-tumor drug - Google Patents
A kind of antitumor Psoralen lipopolysaccharides and its extraction separation method and the application in terms of preparing anti-tumor drug Download PDFInfo
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- CN110128562A CN110128562A CN201910456385.5A CN201910456385A CN110128562A CN 110128562 A CN110128562 A CN 110128562A CN 201910456385 A CN201910456385 A CN 201910456385A CN 110128562 A CN110128562 A CN 110128562A
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- Prior art keywords
- psoralen
- lipopolysaccharides
- psoralea corylifolia
- pcp
- antitumor
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- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 title claims abstract description 54
- VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000002158 endotoxin Substances 0.000 title claims abstract description 26
- 229920006008 lipopolysaccharide Polymers 0.000 title claims abstract description 26
- 230000000259 anti-tumor effect Effects 0.000 title claims abstract description 22
- 238000000605 extraction Methods 0.000 title claims description 16
- 239000002246 antineoplastic agent Substances 0.000 title claims description 9
- 229940041181 antineoplastic drug Drugs 0.000 title claims description 9
- 238000000926 separation method Methods 0.000 title description 5
- 244000226566 Psoralea corylifolia Species 0.000 claims abstract description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 150000004676 glycans Chemical class 0.000 claims abstract description 32
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 30
- 239000005017 polysaccharide Substances 0.000 claims abstract description 30
- 235000009508 confectionery Nutrition 0.000 claims abstract description 29
- 101100135798 Caenorhabditis elegans pcp-1 gene Proteins 0.000 claims abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000010828 elution Methods 0.000 claims abstract description 19
- 229910021642 ultra pure water Inorganic materials 0.000 claims abstract description 19
- 239000012498 ultrapure water Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 16
- 235000019441 ethanol Nutrition 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 13
- 239000003208 petroleum Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229920005654 Sephadex Polymers 0.000 claims abstract description 8
- 239000011780 sodium chloride Substances 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000006228 supernatant Substances 0.000 claims abstract description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 5
- 239000012507 Sephadex™ Substances 0.000 claims abstract description 5
- 239000012153 distilled water Substances 0.000 claims abstract description 5
- 201000005202 lung cancer Diseases 0.000 claims abstract description 5
- 208000020816 lung neoplasm Diseases 0.000 claims abstract description 5
- 238000004440 column chromatography Methods 0.000 claims abstract description 4
- 239000002244 precipitate Substances 0.000 claims abstract description 3
- 238000002835 absorbance Methods 0.000 claims description 12
- 229960004756 ethanol Drugs 0.000 claims description 9
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 7
- 238000000502 dialysis Methods 0.000 claims description 7
- 238000004108 freeze drying Methods 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 5
- 238000005238 degreasing Methods 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000001117 sulphuric acid Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- JGEVJQBAHWCNEN-UHFFFAOYSA-N C1(=CC=CC=C1)O.S(=O)(=O)(O)O.C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)O.S(=O)(=O)(O)O.C1=CC=CC=C1 JGEVJQBAHWCNEN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000019634 flavors Nutrition 0.000 claims description 2
- 150000004804 polysaccharides Polymers 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 7
- 229920002678 cellulose Polymers 0.000 abstract description 3
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- 238000004587 chromatography analysis Methods 0.000 abstract description 3
- 238000001556 precipitation Methods 0.000 abstract 2
- 238000002474 experimental method Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000002772 monosaccharides Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 108010009736 Protein Hydrolysates Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- PYMYPHUHKUWMLA-VPENINKCSA-N aldehydo-D-xylose Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-VPENINKCSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002270 exclusion chromatography Methods 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
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 235000001497 healthy food Nutrition 0.000 description 1
- 238000000703 high-speed centrifugation Methods 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 150000002771 monosaccharide derivatives Chemical class 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
Classifications
-
- 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
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
-
- 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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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Epidemiology (AREA)
- Sustainable Development (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The present invention relates to a kind of preparation method of antitumor Psoralen lipopolysaccharides, specifically: 1) psoralea corylifolia crush, and is successively extracted with petroleum ether, 70 ± 5% ethyl alcohol room temperatures, ultrapure water heating extracting, concentrating filter liquor, alcohol precipitation obtain psoralea corylifolia Thick many candies；2) psoralea corylifolia Thick many candies are taken off into albumen using Sevag method, obtained supernatant is concentrated under reduced pressure, alcohol precipitation, taking precipitate is dry to get Deproteinated psoralea corylifolia Thick many candies；3) Deproteinated psoralea corylifolia Thick many candies are taken, with DEAE-52 cellulose chromatography column purification, gradient elution successively is carried out with ultrapure water, 0.05,0.1,0.2,0.3mol/L NaCl solution, the eluting peak of distilled water is component PC-1, and the eluting peak of 0.2 mol/L NaCl solution is component PC-4；4) polysaccharide component that component PC-1, PC-4 is purified through Sephadex G-100 dextran gel column chromatography respectively is named as PCp-1, PCp-4；PCp-1 and/or PCp-4 is antitumor Psoralen lipopolysaccharides.It is found through experiment that: the Psoralen lipopolysaccharides can effectively inhibit the activity of A549 cell, can be used for preparing antitumor especially anti-lung-cancer medicament.
Description
Technical field
The invention belongs to technical field of extraction of Chinese traditional medicine, and in particular to a kind of anti-tumor activity Psoralen lipopolysaccharides extracts separation
Method and the application in terms of preparing anti-tumor drug.
Background technique
As aging of population aggravation, ecological environment wreck, unhealthy life style and food-safety problem etc. are convex
Existing, tumor incidence and the death rate persistently rise, and bring serious harm to people's life, health and society.Common tumour medicine
Although object and radiotherapy, chemotherapy etc. have certain therapeutic effect, side effect is larger.Chinese medicine is the medical treasure-house in China, Chinese medicine
Often have the characteristics that multiple target point, hypotoxicity, persistent, Chinese medicine is individually or auxiliary western medicine tumour is improving immunity of organism
Power, extension life cycle, reduction recurrence and metastatic rate and mitigation side effect etc. have positive meaning.Therefore it is with traditional Chinese medicine
New type natural anti-tumor drug is researched and developed in source, is an emphasis direction of anti-tumor drug research.
Psoralea corylifolia is legumes psoraleaePsoralea corylifoliaL. dry mature fruit, in tradition
Medicine.According to being held in " notice of the Ministry of Public Health about further specification healthy food material management " (defend method prison hair [2002] No. 51)
Row, psoralea corylifolia is the article that can be used for health food.Modern research shows that psoralea corylifolia contains Coumarins, flavonoids, monoterpenes
Equal Multiple components, show the multiple efficacies such as anti-inflammatory, antibacterial, anti-oxidant, hypoglycemic.About the research of Psoralen lipopolysaccharides, at present
Only domestic several scholars have carried out Primary Study to the content and its immunocompetence of psoralea corylifolia Thick many candies, have no slightly more to psoralea corylifolia
Further isolating and purifying for sugar, obtains single polysaccharide component, carries out structural analysis and antitumor activity to it.
Summary of the invention
Present invention aims to overcome that prior art defect, provide it is a kind of extracted from psoralea corylifolia it is isolated, have it is anti-
The Psoralen lipopolysaccharides of tumor promotion.
The present invention also provides the extraction separation method of above-mentioned Psoralen lipopolysaccharides and answering in terms of preparing anti-tumor drug
With.
To achieve the above object, the present invention adopts the following technical scheme:
A kind of preparation method of antitumor Psoralen lipopolysaccharides comprising following steps:
1) prepare Thick many candies: psoralea corylifolia crushes, and first extracts degreasing with petroleum ether room temperature, and residue volatilizes petroleum ether, then with 70 ± 5%
For the extraction of ethyl alcohol room temperature to remove depigmentaton and small molecule ingredient, residue evaporates into no ethanol flavor, is then added with ultrapure water in 85 ± 5 DEG C
Thermal extraction is filtered with Buchner funnel while hot after extraction, and filtrate concentration obtains concentrate, is then added into concentrate anhydrous
Ethyl alcohol makes final concentration of 70-75%, stands, and collects precipitating, and successively dehydrated alcohol, acetone washing precipitating, volatilize solvent up to Psoralen
Rouge Thick many candies；
2) Deproteinated psoralea corylifolia Thick many candies are prepared: psoralea corylifolia Thick many candies being completely dissolved with ultrapure water and obtain psoralea corylifolia Thick many candies
Solution takes off albumen using Sevag method, will obtained supernatant be concentrated under reduced pressure after dehydrated alcohol is added to final concentration of 75 ± 2%,
It stands, centrifugation, taking precipitate, it is dry to get Deproteinated psoralea corylifolia Thick many candies；
3) Deproteinated psoralea corylifolia Thick many candies are taken, ultrapure water dissolution is centrifuged off insoluble matter, is then loaded to DEAE-52 fiber
Plain chromatographic column, successively carries out gradient elution with ultrapure water, 0.05,0.1,0.2,0.3mol/L NaCl solution, and eluent uses benzene
Phenol-sulfuric acid method is detected, and the absorbance at 490 nm is measured, and to elute pipe number as abscissa, absorbance is ordinate, is drawn
Polysaccharide elution curve merges polysaccharide sample, the concentration of same eluting peak, dialysis, freeze-drying；Wherein, the eluting peak of distilled water
For component PC-1, the eluting peak of 0.2 mol/L NaCl solution is component PC-4；
4) component PC-1 is dissolved with ultrapure water, is loaded to Sephadex G-100 dextran gel column chromatography, with ultrapure water elution,
It is detected using phend-sulphuric acid, measures the absorbance at 490 nm, to elute pipe number as abscissa, absorbance is vertical sits
Mark draws polysaccharide elution curve, merges the polysaccharide sample of same eluting peak, the polysaccharide group obtained after concentration, dialysis, freeze-drying
Divide and is named as PCp-1；
Component PC-4 is eluted using method identical with component PC-1, merges the polysaccharide sample of same eluting peak, is concentrated, thoroughly
The polysaccharide component obtained after analysis, freeze-drying is named as PCp-4；
PCp-1 and/or PCp-4 is antitumor Psoralen lipopolysaccharides.
Specifically, being extracted degreasing 3-5 times with petroleum ether room temperature, each 2-4d in step 1)；It is soaked with 70 ± 5% ethyl alcohol room temperatures
It mentions 3-5 times, each 2-4 d；Ultrapure water heating extracting 2-4 times, each 3-5 h.
Specifically, when Sevag method takes off albumen, Sevag reagent used is by the chloroform that volume ratio is 4:1 and just in step 2
Butanol composition；Sevag reagent additive amount is 1/4 to 1/2, preferably the 1/3 of psoralea corylifolia Thick many candies liquor capacity.
The present invention also provides the antitumor Psoralen lipopolysaccharides being prepared using the above method.
The present invention also provides above-mentioned Psoralen lipopolysaccharides to prepare the application in anti-tumor drug or food.
Further, preferably above-mentioned Psoralen lipopolysaccharides is preparing the application in anti-lung-cancer medicament or food.
Compared to the prior art, beneficial effects of the present invention:
The present invention uses special extraction separation method isolated polysaccharide component PCp-1 and PCp-4 from psoralea corylifolia, and with non-
The antitumor action of the polysaccharide component is investigated for Small Cell Lung Cancer A549 cell, test result shows: the psoralea corylifolia
Polysaccharide can effectively inhibit the activity of A549 cell, illustrate that it, with good antitumor action, can be used for preparing anti-tumor drug,
It is particularly useful for preparing anti-lung-cancer medicament or food.
Detailed description of the invention
Fig. 1 psoralea corylifolia Thick many candies DEAE-52 cellulose chromatography column elution curve；
Fig. 2 component PC-1 and PC-4 is through SephadexG-100 gel column chromatography elution curve；
The GC chromatogram of Fig. 3 standard mixture of monosaccharides；
The hydrolysate GC chromatogram of Fig. 4 PCp-1；
The hydrolysate GC chromatogram of Fig. 5 PCp-4.
Specific embodiment
Technical solution of the present invention is further discussed in detail with reference to embodiments, but protection scope of the present invention
It is not limited thereto.
Embodiment 1
1, a kind of preparation method of antitumor Psoralen lipopolysaccharides, specifically comprises the following steps:
1) prepare Thick many candies: psoralea corylifolia (4.4 kg) crushes, and is extracted 3 times with petroleum ether room temperature, 3 d, carries out ungrease treatment every time.
Residue after extraction volatilizes petroleum ether, then is extracted 4 times with 70% ethyl alcohol room temperature, and 3 d, the residue after extraction evaporate into no second every time
Alcohol taste (petroleum ether, 70% ethyl alcohol additive amount are advisable with submerging psoralea corylifolia).Then with ultrapure water in 85 DEG C of heating extractions, 2 (heating
Solid-liquid ratio is about 1g:20 mL when extraction), 5 h every time；It is filtered while hot with Buchner funnel after extraction, merging filtrate, filtrate
Rotary evaporation is concentrated into 1/4 of original volume or so, obtains concentrate.Dehydrated alcohol is added into concentrate makes final concentration of 70%
(percent by volume, similarly hereinafter) is stored at room temperature 12 h, and centrifugation discards supernatant liquid, collects precipitating, successively dehydrated alcohol, acetone washing
Precipitating, volatilizes solvent up to psoralea corylifolia Thick many candies.
2) the psoralea corylifolia Thick many candies of above-mentioned preparation are completely dissolved with ultrapure water and obtain psoralea corylifolia Thick many candies solution, are used
Sevag method takes off albumen, specifically: Sevag reagent, magnetic agitation concussion is added according to the 1/3 of psoralea corylifolia Thick many candies liquor capacity
30 min, 4000 r/min are centrifuged 5 min, remove intermediate denatured protein and lower layer's organic solvent, supernatant is continued to repeat
Aforesaid operations, up to no albuminate layer occurs；Sevag reagent is made of the chloroform that volume ratio is 4:1 and n-butanol.It will be final
Dehydrated alcohol to final concentration of alcohol is added in obtained supernatant after being concentrated under reduced pressure be 70%, is stored at room temperature 12 h, is centrifuged, it is heavy to take
Starch, it is dry to get Deproteinated psoralea corylifolia Thick many candies.
3) psoralea corylifolia Thick many candies 1.0g after above-mentioned de- albumen is taken, is dissolved with 10 mL ultrapure waters, high speed centrifugation removes insoluble
Then object is loaded to DEAE-52 cellulose chromatography column, successively use distilled water, 0.05,0.1,0.2,0.3mol/L NaCl solution
Gradient elution is carried out, elutes 400,800,800,800,700 mL respectively, flow control is collected in 1.0 mL/min, every 5 min
One pipe, eluent are detected using phend-sulphuric acid, are measured the absorbance at 490 nm with microplate reader, are to elute pipe number
Abscissa, absorbance are ordinate, are drawn polysaccharide elution curve (elution curve is as shown in Figure 1).Merge the more of same eluting peak
Sugar juice, 50 DEG C of reduced pressures, (room temperature, molecular cut off 8000-14000 just start to change a water every 3h, altogether for dialysis
Meter three times, then changes a water every 12h, it is total twice), be freeze-dried in freeze drier, wherein the eluting peak of distilled water
For component PC-1, the eluting peak of 0.2mol/L NaCl solution is component PC-4.
4) 200 mg component PC-1 are taken, is dissolved with 2 mL ultrapure waters, is loaded to Sephadex G-100 sephadex color
Spectrum column (1.5 × 100 cm) further isolates and purifies, and with ultrapure water elution, flow control is collected in 0.8 mL/min, every 5 min
One pipe, is detected using phend-sulphuric acid, measures the absorbance at 490 nm, to elute pipe number as abscissa, absorbance is
Ordinate is drawn polysaccharide elution curve (elution curve is as shown in Figure 2), merges the polysaccharide sample of same eluting peak, is concentrated under reduced pressure
(50 DEG C), (room temperature, molecular cut off 8000-14000 just start to change a water every 3h, amount to three times, then every for dialysis
A water is changed every 12h, is amounted to twice), the polysaccharide component obtained after being freeze-dried in freeze drier is named as PCp-1；
Component PC-4 is eluted (elution curve is as shown in Figure 2) using method identical with component PC-1, merges same elution
The polysaccharide sample at peak, the polysaccharide component obtained after concentration, dialysis, freeze-drying are named as PCp-4；
PCp-1 and/or PCp-4 is antitumor Psoralen lipopolysaccharides.
The measurement of psoralea corylifolia polysaccharide molecular weight:
Specific preparation process is as follows: taking polysaccharide component PCp-1 and PCp-4 to send to Beijing Physichemistry Analysis & Measurment Centre and analyzes inspection
It surveys, measures its molecular weight according to the molecular exclusion chromatography that " Chinese Pharmacopoeia " (version in 2015) is included.The results show that PCp-1 and
The molecular weight of PCp-4 is respectively 2.721 × 104With 2.850 × 104G/mol, see Table 1 for details.
The molecular weight of table 1 PCp-1 and PCp-4
。
, Psoralen lipopolysaccharides monosaccharide constituent measurement.
The hydrolysis of 3.1 polysaccharide
Each 10 mg of polysaccharide PCp-1 and PCp-4 is accurately weighed, is added in 5 mL ampoule bottles, the trifluoro of 3 mL, 4 mol/L is added
Acetic acid, nitrogen tube sealing.3 h are hydrolyzed at 110 DEG C, rotary evaporation removes trifluoroacetic acid solution, and it is residual that a small amount of methanol dissolution is added
Slag, rotary evaporated to dryness is dry, is so repeated 3 times, and obtains hydrolysate, spare.
The derivatization of 3.2 monosaccharide
10 mg of hydroxylamine hydrochloride is added into hydrolysate, 0.5 mL of pyridine is added, oscillation mixes, is put into 90 DEG C of water-baths and heats
React 30 min.Taking-up is cooled to room temperature, and 0.5 mL of acetic anhydride is added, and the reaction was continued at 90 DEG C 30 min are to carry out acetyl
Change, reaction product is injected gas-chromatography after 0.22 μm of membrane filtration and analyzed；Standard monosaccharide is handled with same procedure, and
Standard monosaccharide derivatives mixed liquor is made.
3.3 GC conditions
Chromatographic column: HP(30 m × 0.35 mm, 0.25 μm)；Injector temperature: 250 DEG C；Detector temperature: 280 DEG C；Chromatographic column liter
Warm program: then 100 DEG C of initial temperature 1 min of holding rise to 240 DEG C by 100 DEG C with the speed of 4 DEG C/min, keep 10
min；Carrier gas: high pure nitrogen, 2 mL/min of flow velocity；Sample volume is 2 μ L.
3.4 monosaccharide composition analysis results
The GC chromatogram of standard mixture of monosaccharides is shown in Fig. 3 (1. L- rhamnoses；2. 3. D- xylose of L-arabinose；4. D- is sweet
Dew sugar；5.D- glucose；6.D- galactolipin), Fig. 4 and Fig. 5 are respectively the monosaccharide GC chromatogram of PCp-1 and PCp-4 after hydrolysis,
It can determine that the monosaccharide of sample is constituted by the comparison with retention time in standard monosaccharide map, the results are shown in Table 2.
The monosaccharide of table 2 PCp-1 and PCp-4 forms
As can be seen from Table 2: PCp-1 and PCp-4 is heteroglycan, at least by rhamnose, arabinose, xylose, mannose, Portugal
Grape sugar and galactolipin composition, and molar ratio is different；PCp-1 contains higher galactolipin and arabinose, and PCP-4 is mainly by sandlwood
Sugar, xylose and galactolipin composition.
The activity analysis of antitumor Psoralen lipopolysaccharides PCp-1 and PCp-4
The Non-small Cell Lung Cancer A 549 of logarithmic growth phase is laid on 96 microwell plates (2 × 104), after culture for 24 hours at dosing
Reason is separately added into the PCp-1 and PCp-4 and positive control cis-platinum of various concentration, acts on 48h, then detects cell using mtt assay
Survival condition.Numerical statistic compares its conspicuousness using SPSS19.0 software one-way analysis of variance method (One-Way ANOVA)
Difference.Measurement result is shown in Table 3 and table 4.
3 various concentration PCp-1 of table handles cell survival rate after A549 cell 48h
4 various concentration PCp-4 of table handles cell survival rate after A549 cell 48h
With the increase of PCp-1 and PCp-4 concentration in culture medium it can be seen from table 3 and table 4, the survival rate of A549 cell is in
Downward trend, and the anti-tumor activity of both polysaccharide has certain difference, this may be with monosaccharide in two kinds of polysaccharide components
It forms related with content.When PCp-1 and PCp-4 concentration reaches 100 μM, mean percent cell survival is successively only 48.77%,
51.87%, illustrate that PCp-1 and PCp-4 have apparent inhibiting effect (IC to the survival of A549 cell50=64.84 and 126.3 μM),
Comparatively, activity is lower than positive control cis-platinum (IC50=11 μM).
Above-mentioned test result shows: Psoralen lipopolysaccharides of the present invention can effectively inhibit the activity of A549 cell, illustrate that it has
Good antitumor action can be used for preparing anti-tumor drug, be particularly useful for preparing anti-lung-cancer medicament or food.
Claims (6)
1. a kind of preparation method of antitumor Psoralen lipopolysaccharides, which comprises the steps of:
1) prepare Thick many candies: psoralea corylifolia crushes, and first extracts degreasing with petroleum ether room temperature, and residue volatilizes petroleum ether, then with 70 ± 5%
The extraction of ethyl alcohol room temperature, residue evaporate into no ethanol flavor, then with ultrapure water in 85 ± 5 DEG C of heating extractions, after extraction while hot
It filters, filtrate concentration obtains concentrate, and dehydrated alcohol is then added into concentrate makes final concentration of 70-75%, stands, and collects
Precipitating is to get psoralea corylifolia Thick many candies；
2) Deproteinated psoralea corylifolia Thick many candies are prepared: psoralea corylifolia Thick many candies being completely dissolved with ultrapure water and obtain psoralea corylifolia Thick many candies
Solution takes off albumen using Sevag method, will obtained supernatant be concentrated under reduced pressure after dehydrated alcohol is added to final concentration of 75 ± 2%,
It stands, centrifugation, taking precipitate, it is dry to get Deproteinated psoralea corylifolia Thick many candies；
3) Deproteinated psoralea corylifolia Thick many candies are taken, ultrapure water dissolution is centrifuged off insoluble matter, is then loaded to DEAE-52 fiber
Plain chromatographic column, successively carries out gradient elution with ultrapure water, 0.05,0.1,0.2,0.3mol/L NaCl solution, and eluent uses benzene
Phenol-sulfuric acid method is detected, and the absorbance at 490 nm is measured, and to elute pipe number as abscissa, absorbance is ordinate, is drawn
Polysaccharide elution curve merges polysaccharide sample, the concentration of same eluting peak, dialysis, freeze-drying；Wherein, the eluting peak of distilled water
For component PC-1, the eluting peak of 0.2 mol/L NaCl solution is component PC-4；
4) component PC-1 is dissolved with ultrapure water, is loaded to Sephadex G-100 dextran gel column chromatography, with ultrapure water elution,
It is detected using phend-sulphuric acid, measures the absorbance at 490 nm, to elute pipe number as abscissa, absorbance is vertical sits
Mark draws polysaccharide elution curve, merges the polysaccharide sample of same eluting peak, the polysaccharide group obtained after concentration, dialysis, freeze-drying
Divide and is named as PCp-1；
Component PC-4 is eluted using method identical with component PC-1, merges the polysaccharide sample of same eluting peak, is concentrated, thoroughly
The polysaccharide component obtained after analysis, freeze-drying is named as PCp-4；
PCp-1 and/or PCp-4 is antitumor Psoralen lipopolysaccharides.
2. the preparation method of antitumor Psoralen lipopolysaccharides as described in claim 1, which is characterized in that in step 1), use petroleum ether
Room temperature extracts degreasing 3-5 times, each 2-4d；It is extracted 3-5 times with 70 ± 5% ethyl alcohol room temperatures, each 2-4 d；Ultrapure water heating extracting
2-4 times, each 3-5 h.
3. the preparation method of antitumor Psoralen lipopolysaccharides as described in claim 1, which is characterized in that in step 2, Sevag method is de-
When albumen, Sevag reagent used is made of the chloroform that volume ratio is 4:1 and n-butanol；Sevag reagent additive amount is that psoralea corylifolia is thick
1/4 to the 1/2 of polysaccharide solution volume.
4. the antitumor Psoralen lipopolysaccharides being prepared using any the method for claims 1 to 3.
5. Psoralen lipopolysaccharides application in preparation of anti-tumor drugs as claimed in claim 4.
6. Psoralen lipopolysaccharides as claimed in claim 4 is preparing the application in anti-lung-cancer medicament.
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