CN1305466C - Application of Cytospora bacterin B in preparation of antineoplastic medicine - Google Patents
Application of Cytospora bacterin B in preparation of antineoplastic medicine Download PDFInfo
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- CN1305466C CN1305466C CNB2005100856747A CN200510085674A CN1305466C CN 1305466 C CN1305466 C CN 1305466C CN B2005100856747 A CNB2005100856747 A CN B2005100856747A CN 200510085674 A CN200510085674 A CN 200510085674A CN 1305466 C CN1305466 C CN 1305466C
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 241000235819 Cytospora Species 0.000 title description 11
- 230000000118 anti-neoplastic effect Effects 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 7
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 6
- 240000002044 Rhizophora apiculata Species 0.000 abstract description 13
- 241000233866 Fungi Species 0.000 abstract description 10
- 230000000259 anti-tumor effect Effects 0.000 abstract description 4
- 210000004881 tumor cell Anatomy 0.000 abstract description 4
- 241000120622 Rhizophoraceae Species 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000000855 fermentation Methods 0.000 description 8
- 230000004151 fermentation Effects 0.000 description 8
- UVVWQQKSNZLUQA-UHFFFAOYSA-N 2-[3,5-dihydroxy-2-(1-oxooctyl)phenyl]acetic acid ethyl ester Chemical compound CCCCCCCC(=O)C1=C(O)C=C(O)C=C1CC(=O)OCC UVVWQQKSNZLUQA-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 235000012015 potatoes Nutrition 0.000 description 4
- 239000013535 sea water Substances 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 241001602478 Dothiorella sp. Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000006143 cell culture medium Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012549 training Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 244000307888 Acanthus ebracteatus Species 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000001154 Dermoid Cyst Diseases 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 208000019065 cervical carcinoma Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 201000008968 osteosarcoma Diseases 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 238000011218 seed culture Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- QGZCUOLOTMJILH-UHFFFAOYSA-N 2h-tetrazol-2-ium;bromide Chemical compound [Br-].C1=N[NH+]=NN1 QGZCUOLOTMJILH-UHFFFAOYSA-N 0.000 description 1
- 210000003771 C cell Anatomy 0.000 description 1
- 241000862508 Ceriops Species 0.000 description 1
- 241000862497 Ceriops tagal Species 0.000 description 1
- 208000010445 Chilblains Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 241001674359 Didymosphaeria enalia Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GLXFCNFYBPZEIR-UHFFFAOYSA-N OC(CC(C)C(=O)C(CC(CC(C)O)O)C)CC(C)O Chemical compound OC(CC(C)C(=O)C(CC(CC(C)O)O)C)CC(C)O GLXFCNFYBPZEIR-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000130764 Tinea Species 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 230000001139 anti-pruritic effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000003908 antipruritic agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 230000020411 cell activation Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000006750 hematuria Diseases 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012982 microporous membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
涉及一种来源于红树植物内生真菌-小穴壳菌HTF3的壳囊孢菌素B化合物在制备抗肿瘤中的应用。一类来源于红树林内生真菌的壳囊孢菌素B化合物对多种人体肿瘤细胞均表现出较好的抑制作用，可用于制备抗肿瘤药物。The invention relates to the application of an ascosporine B compound derived from the mangrove plant endophytic fungus-Aculetosporum HTF 3 in the preparation of anti-tumor. A class of ascosporine B compounds derived from endophytic fungi of mangroves have good inhibitory effects on various human tumor cells, and can be used to prepare antitumor drugs.
Description
The application is that application number is 200310114048.7, and the applying date is 2003.11.08, and the application people is an Xiamen University, and invention and created name is divided an application for " Cytospora bacterin B method for making and the application in preparation antitumor and antifungal drug ".
Technical field
The present invention relates to a kind of mangrove endogeny eumycete-Dothiorella ribis HTF that derives from
3(Dothiorella sp.HTF
3) the Cytospora bacterin B chemical compound in the application of preparation in the antitumor.
Background technology
Rhizophora apiculata Blume is to be grown in the woody plant community, xylium that the geographic mud flat in estuary is coated, and it is special to play a part in balance of nature as the extra large Lu Bianyuan ecosystem of uniqueness.Mangrove plant is not only important economic plants, also is medicinal plants commonly used among the people, can be used to control hematuria as the bark extractive of mangrove acanthus (Acanthus ilicifolius); The bark of Ceriop tagl (perr), c. B. Rob (Ceriops tagal) is smashed to pieces can hemostasis, relieving constipation and treatment malignant boil, and the seed oil expression can antipruritic and treatment tinea, also can treat chilblain etc.
Exist abundant endogenetic fungus in the mangrove, there is report to think that the medicinal ingredient of mangrove is all produced by its endogenetic fungus, few document (1, Brady, S., Wagenaar, M.W., Singh, M., et al.The cytosporonesisolated from an endophytic fungus.Org.Lett.2000,2 (25): 4043-4046; 2, Bandaranayake, W.M..Traditional and medicinal uses of mangroves.Mangroves and Salt Marshes, 1998,2:133-148; 3, Bandaranayake, W.M..Bioactivities, bioactive compounds and chemicalconstituents of mangrove plants.Wetland Ecology and Management, 2002,10:421-452; 4, Lin Y., Wu X., Deng z., et al.The metabolites of the mangrove fungus Verruculina enalia No.2606 from a salt lake in the Bahamas.Phytochemistry, 2002,59:469-471) the report endogenetic fungus that also proved mangrove can produce the chemical compound with new construction and strong physiologically active really.But domestic and international at present work in this respect just just begins, and its research has high theoretical value and actual application value for this reason.
Summary of the invention
The object of the present invention is to provide a kind of application of chemical compound in the preparation antitumor drug that derives from mangrove endogeny eumycete (cytosporone B).
Mangrove endogeny eumycete-Dothiorella ribis HTF3 (Dothiorella sp.HTF that the present invention is used
3) being preserved in Chinese typical culture collection center (CCTCC, Chinese Wuhan University are in the school), preserving number is CCTCC NO:M203067, preservation date is on August 29th, 2003.
The structural formula of the said Cytospora bacterin B of the present invention (cytosporone B) chemical compound is:
(3,5-dihydroxy-methyln-hexyl ketone base)-ethyl phenylacetate
Said Cytospora bacterin B chemical compound can adopt following preparation method:
1) endogenetic fungus (Dothiorella sp.HTF
3) seed culture:
Peeling potatoes, chopping 20g, decocting in water adds glucose 1～3g in filtrate filtered, agar 1.5～2.0g, sea water is settled to 100ml, and the test tube slant is made in sterilization, and the picking strain inserts the inclined-plane, cultivates under the room temperature 5～15 days;
2) fermentation culture of endogenetic fungus:
Peeling potatoes, chopping 20g, decocting in water adds glucose 1～3g in filtrate filtered, and sea water is settled to 100ml, and sterilization chooses cultured bacterial strain on the inclined-plane into fermentation medium, cultivates under the room temperature 5～15 days;
3) after being removed by filter fermentation liquid, above-mentioned fermentation culture obtains thalline;
4) thalline oven dry, soak repeatedly with ethyl acetate, combined ethyl acetate, concentrating under reduced pressure, the paste of gained separates with silica gel column chromatography, and gradient elution is carried out to 0/100 in petrol ether/ethyl acetate=100/0, collects the two ratio and be 1/1 o'clock eluent, concentrating under reduced pressure promptly obtains this chemical compound, and content is the 9mg/g dry cell weight.
The experimental data of this chemical compound of gained is:
Colorless oil; EMS:m/z (rel.int.): 323.3[M+H]
+(100), 345.3[M+Na]
+(11.4), 361.2[M+K]
+(4.2);
1H NMR and
13C NMR (400MHz, CDCl
3, ppm) see Table 1.
The Cytospora bacterin B chemical compound that the said class of the present invention derives from mangrove endophytic fungus all shows good inhibitory effect to multiple human body tumour cell, can be used for preparing antitumor drug.
The NMR data of table 1. Cytospora bacterin B
| Position | 1H-NMR | Position | 13C-NMR |
| 2 | 3.70(s) | 1 | 171.0 |
| 4 | 6.25(s) | 2 | 41.8 |
| 6 | 6.25(s) | 3 | 136.0 |
| 9 | 4 | 112.0 | |
| 10 | 2.75(t) | 5 | 163.1 |
| 11 | 1.6 | 6 | 103.2 |
| 12 | 1.22 | 7 | 161.0 |
| 13 | 1.19 | 8 | 116.0 |
| 14 | 1.20 | 9 | 207 |
| 15 | 1.20 | 10 | 43.7 |
| 16 | 0.8 | 11 | 25.0 |
| 17 | 4.2(q，7) | 12 | 29.4 |
| 18 | 1.20(t，7) | 13 | 29.2 |
| OH-5 | 14 | 31.8 | |
| OH-7 | 15 | 22.8 | |
| 16 | 14.2 | ||
| 17 | 61.0 | ||
| 18 | 14.1 |
The specific embodiment
Following examples provide the preparation method of said Cytospora bacterin B chemical compound.
1) seed culture of endogenetic fungus:
With 20g peeling potatoes, chopping, decocting in water 30min adds glucose 1g in filtrate filtered, agar 1.6g, and 50% sea water is settled to 100ml, and the test tube slant is made in sterilization, and the picking strain inserts the inclined-plane, cultivates 10 days down for 25 ℃;
2) fermentation culture of endogenetic fungus:
With 20g peeling potatoes, chopping, decocting in water 30min adds glucose 1.5g in filtrate filtered, and 50% sea water is settled to 100ml, and sterilization chooses cultured bacterial strain on the inclined-plane into fermentation medium, cultivates 8 days down for 26 ℃;
3) after being removed by filter fermentation liquid, above-mentioned fermentation culture obtains thalline;
4) thalline oven dry, soak repeatedly with ethyl acetate, combined ethyl acetate, concentrating under reduced pressure, the paste of gained separates with silica gel column chromatography, and gradient elution is carried out to 0/100 in petrol ether/ethyl acetate=100/0, collects the two ratio and be 1/1 o'clock eluent, concentrating under reduced pressure promptly obtains this chemical compound, and content is the 9mg/g dry cell weight.
The said Cytospora bacterin B chemical compound of the present invention can be used for preparing antitumor drug, and its anti-tumor activity test experience is as follows:
1) tumor cell line
People B Lymphoma Raji Cells, human mouth dermoid cancer KB cell, people's osteogenic sarcoma MG-63 cell, people's lung cancer A549 cell, human cervical carcinoma hela cell etc.
2) material
A MTT (tetrazolium bromide):
Phosphate buffer (PBS) dissolving MTT (Thiazoyl blue) with 0.01mol/L arrives final concentration 5mg/ml, and 0.22 μ m filtering with microporous membrane degerming is kept in Dark Place in 4 ℃ after the packing;
B SDS lysate:
100g dodecyl sodium sulfate (SDS), 1N HCL10ml, heating for dissolving, distilled water is settled to 1000ml.
C cell culture medium (full training):
One bag of 10g dry powder RMPI 1640 (Gibco Co.Ltd.) cell culture medium is dissolved in the 1L distilled water; Add 2gNaHCO
3Seal after stirring evenly dissolving, place 4 ℃ to spend the night, remove impurity with natural sedimentation; Add next day 10%-15% deactivation (56 ℃, calf serum 30min) and 1% multi-resistance mother solution; Behind the mixing with the membrane filtration degerming in 0.22 μ m aperture.
3) configuration of compound c ytosporone B
Get a certain amount of Cytospora bacterin B, with dissolve with methanol and to adjust concentration be 5mg/ml, the membrane filtration degerming in 0.22 μ m aperture, 4 ℃ of preservations are standby.
4) cultivation of tumor cell
The a cell activation:
Get a clean beaker, the clean warm water of packing into, water temperature transfers to 37～40 ℃; Frozen pipe is taken out the rapid warm water that drops into thaw from liquid nitrogen, and the freeze-stored cell access is equipped with in the culture bottle of cell culture medium in advance, at 37 ℃, 5%CO
2, 100% humidity condition under cultivate, the observation of cell growing state is in time changed culture fluid, is divided bottle.
The b cell counting:
Select logarithm to generate the phase cell, trypsinization moves in the centrifuge tube, adds full the training to 10ml, gets one after another drop ofly to go in the counting chamber one side groove, and inverted microscope is counting down.Adjust cell number to 1 * 10
5/ ml.
C is active to be detected:
1. 96 orifice plates shine 1h under the ultraviolet light in superclean bench;
2. in each hole, add cell suspension 80 μ l, 37 ℃, 5% CO
2, 100% humidity condition under cultivate 24h;
3. add 20 μ l with training the solution that gradient dilution becomes a series of concentration entirely, continue to cultivate 48h;
4. every hole adds MTT solution 10 μ l, jolts gently to make the granule dissolving, places 3h for 37 ℃;
5. take out culture plate, every hole adds 10%SDS solution 100 μ l, and 37 ℃ of dissolvings are spent the night;
6. measure each hole light absorption value (reference wavelength is 655nm) with integrated enzyme reaction instrument 570nm, calculate suppression ratio by following formula:
Suppression ratio=(matched group OD value-experimental group OD value)/matched group OD value * 100%
7. be vertical coordinate with the suppression ratio, the logarithm of given the test agent concentration is abscissa mapping, and the concentration of obtaining suppression ratio and be at 50% o'clock is IC
50
The d result of the test:
Cytosporone B is to the IC of people B Lymphoma Raji Cells, human mouth dermoid cancer KB cell, people's osteogenic sarcoma MG-63 cell, people's lung cancer A549 cell, human cervical carcinoma hela cell
50Be respectively 62.5ng/ml, 4 μ g/ml, 1 μ g/ml, 4 μ g/ml and 1 μ g/ml.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100856747A CN1305466C (en) | 2003-11-08 | 2003-11-08 | Application of Cytospora bacterin B in preparation of antineoplastic medicine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100856747A CN1305466C (en) | 2003-11-08 | 2003-11-08 | Application of Cytospora bacterin B in preparation of antineoplastic medicine |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200310114048 Division CN1243100C (en) | 2003-11-08 | 2003-11-08 | Preparation method of ascosporine B and its application in the preparation of antitumor and antifungal drugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1720910A CN1720910A (en) | 2006-01-18 |
| CN1305466C true CN1305466C (en) | 2007-03-21 |
Family
ID=35911749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100856747A Expired - Fee Related CN1305466C (en) | 2003-11-08 | 2003-11-08 | Application of Cytospora bacterin B in preparation of antineoplastic medicine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1305466C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101538537B (en) * | 2009-02-13 | 2011-02-09 | 中国科学院微生物研究所 | Pestalotiopsis fici, and discovery and application of Pestalotiopsis fici generated anti-tumor active compounds thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6541515B2 (en) * | 2000-08-09 | 2003-04-01 | Merck & Co., Inc. | HIV integrase inhibitors |
-
2003
- 2003-11-08 CN CNB2005100856747A patent/CN1305466C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6541515B2 (en) * | 2000-08-09 | 2003-04-01 | Merck & Co., Inc. | HIV integrase inhibitors |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101538537B (en) * | 2009-02-13 | 2011-02-09 | 中国科学院微生物研究所 | Pestalotiopsis fici, and discovery and application of Pestalotiopsis fici generated anti-tumor active compounds thereof |
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| Publication number | Publication date |
|---|---|
| CN1720910A (en) | 2006-01-18 |
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