CN103284992A - Application of Phomopsone C for preparing antiviral medicine - Google Patents
Application of Phomopsone C for preparing antiviral medicine Download PDFInfo
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- CN103284992A CN103284992A CN 201210044406 CN201210044406A CN103284992A CN 103284992 A CN103284992 A CN 103284992A CN 201210044406 CN201210044406 CN 201210044406 CN 201210044406 A CN201210044406 A CN 201210044406A CN 103284992 A CN103284992 A CN 103284992A
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- phomopsone
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- 230000000840 anti-viral effect Effects 0.000 title abstract description 3
- 239000003814 drug Substances 0.000 title abstract description 3
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 6
- 239000003443 antiviral agent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 241000700605 Viruses Species 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 5
- 229960003804 efavirenz Drugs 0.000 description 5
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000209094 Oryza Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241001480007 Phomopsis Species 0.000 description 4
- 241001557902 Phomopsis sp. Species 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000013612 plasmid Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 0 CCCCOC(C(*1)(C1([C@@]1(C)O)C2=IOC(*)=CC2=CC1=O)C(C(*)CC)=O)=O Chemical compound CCCCOC(C(*1)(C1([C@@]1(C)O)C2=IOC(*)=CC2=CC1=O)C(C(*)CC)=O)=O 0.000 description 1
- 101710091045 Envelope protein Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102100034349 Integrase Human genes 0.000 description 1
- 108060001084 Luciferase Proteins 0.000 description 1
- 239000005089 Luciferase Substances 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 101710188315 Protein X Proteins 0.000 description 1
- 108700008625 Reporter Genes Proteins 0.000 description 1
- 241000711975 Vesicular stomatitis virus Species 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a novel application of a Phomopsone C compound for preparing an antiviral medicine. Thus, the novel application of Phomopsone C is developed.
Description
Technical field
The present invention relates to the new purposes of known compound, specifically, is about the application of Phomopsone C for the preparation of antiviral drugs.
Background technology
The present inventor discloses in application number is 201110403130.6 Chinese invention patent application and separated a kind of noval chemical compound that has obtained from the metabolite of Phomopsis (Phomopsis sp.) bacterial strain CGMCC No.5416; identify through structure; determine the chemistry Chinese 7-hydroxyl-3 by name of this chemical compound; 7-dimethyl-3 '-(2-methylbutyryl base)-6-oxo-6; 7-dihydro volution [heterochromatic former alkene 8; 2 '-oxirane]-3 '-carboxylate; English 7-butyl 7-hydroxy-3 by name; 7-dimethyl-3 '-(2-methylbutanoyl)-6-oxo-6; 7-dihydrospiro[isochromene-8; 2 '-oxirane]-3 '-carboxylate, have following structural formula (I):
According to the report of this patent application, this chemical compound can suppress the growth of pulmonary carcinoma, breast carcinoma and pancreatic tumour cell, has anti-tumor activity.
Summary of the invention
The present inventor finds that this chemical compound has the anti HIV-1 virus activity in the further research of the chemical compound (called after Phomopsone C) of the formula (I) that separation from the metabolite of Phomopsis (Phomopsis sp.) bacterial strain CGMCC No.5416 is obtained.
Therefore, the object of the present invention is to provide the application of Phomopsone C.
Compound P homopsone C of the present invention; chemistry Chinese 7-hydroxyl-3 by name; 7-dimethyl-3 '-(2-methylbutyryl base)-6-oxo-6; 7-dihydro volution [heterochromatic former alkene 8,2 '-oxirane]-3 '-carboxylate, English 7-butyl 7-hydroxy-3 by name; 7-dimethyl-3 '-(2-methylbutanoyl)-6-oxo-6; 7-dihydrospiro[isochromene-8,2 '-oxirane]-3 '-carboxylate, have following structural formula:
Can be used for preparing antiviral drugs.
According to a preferred embodiment of the present invention, described virus is HIV virus.
The present invention has found that first Phomopsone C has the anti HIV-1 virus activity, can be used for preparing antiviral drugs, for Phomopsone C has developed a kind of new application.
Description of drawings
Fig. 1 is the mass spectrum of the chemical compound of the present invention's acquisition.
Fig. 2 is the hydrogen spectrogram of the chemical compound of the present invention's acquisition.
Fig. 3 is the carbon spectrogram of the chemical compound of the present invention's acquisition.
The specific embodiment
Below by specific embodiment, the present invention is described in further details.Should be understood that following examples are only for explanation the present invention but not for limiting scope of the present invention.
The used strain of the present invention is Phomopsis (Phomopsis sp.) HCCB03519, be preserved in China Committee for Culture Collection of Microorganisms common micro-organisms center (CGMCC) on October 28th, 2011, the preservation address is No. 3, Yard 1, BeiChen xi Road, Chaoyang District, Beijing City, preserving number CGMCCNo.5416.
Employed efavirenz (Efavirenz) is a kind of non-nucleoside reverse transcriptase inhibitor in following examples, it also is the specific medicament that is used for the treatment of and prevents at present the HIV viral infection clinically, had commercially available by U.S. food Drug Administration (FDA) approval in 1998.
The prescription of employed rice medium is in following examples: rice 800g, pure water 1000ml, pH nature; 115 ℃ of sterilization 20min.
The preparation of embodiment 1, chemical compound
1.1, the fermentation
Adopt rice medium solid fermentation Phomopsis (Phomopsis sp.) bacterial strain HCCB03519, fermentation temperature is 27～30 ℃, and the time is 28～35 days.
1.2, separation and purification
1.1 rice fermented products that obtain are carried out post with decompression silica gel after with ethyl acetate extraction separate, adopt the petrol ether/ethyl acetate mixed solvent to carry out eluting, wherein, the volume ratio of petroleum ether and ethyl acetate is 75: 25, concentrated study.
Then, (3.4 * 52cm) separate, and adopt the methylene chloride mixed solvent to carry out eluting, and wherein, the volume ratio of dichloromethane and methanol is 20: 1, obtains study with Sephadex LH20 post.
The study that obtains is further used half preparative liquid chromatography, and (semi-preparative column is Agilent ZORBAX SB-C18,5 μ m, 9.4mm * separate 250mm) that (0～25min is with 58% acetonitrile isocratic elution, 25～40min is with 58%～100% acetonitrile gradient eluting, flow velocity 2ml/min), the intercepting retention time is the material of 28.5min, finally obtains the pure product of chemical compound, is used for following structure and identifies.
Embodiment2, the structure of chemical compound is identified
Through the positive ion electrospray Mass Spectrometer Method of spraying, collection of illustrative plates shows that its quasi-molecular ion peak is: be m/z 405.1896[M+H as shown in Figure 1 with the chemical compound that obtains among the embodiment 1]
+, corresponding molecular formula is C
22H
29O
7, adopt Bruker Avance II-400 type NMR spectrometer with superconducting magnet to measure hydrogen spectrum (Fig. 2), the carbon spectrum (Fig. 3) of sample.Nuclear magnetic data is as shown in table 1.
The NMR data of table 1, chemical compound
By resolving, determined the ownership of all carbon atoms of this chemical compound and hydrogen atom, the structure that has obtained this chemical compound is as follows:
This compound molecule formula is C
22H
28O
7Molecular weight is 404; chemistry Chinese 7-hydroxyl-3 by name, 7-dimethyl-3 '-(2-methylbutyryl base)-6-oxo-6,7-dihydro volution [heterochromatic former alkene 8; 2 '-oxirane]-3 '-carboxylate; English 7-butyl 7-hydroxy-3 by name, 7-dimethyl-3 '-(2-methylbutanoyl)-and 6-oxo-6,7-dihydrospiro[isochromene-8; 2 '-oxirane]-3 '-carboxylate, called after Phomopsone C.
The anti HIV-1 virus of embodiment 3, chemical compound is active to be detected
The chemical compound that obtains among the embodiment 1 is carried out the active detection of anti HIV-1 virus, and concrete grammar is as follows:
Plasmid pNL4.3.Env-.Luc (NIH AIDS Research ﹠amp; Reference Reagent Program, Catalog Number 3418) can express and have the reporter gene luciferase but the HIV-1 virus of envelope protein disappearance, plasmid pHCMV-G (Yee, J.et al, (1994) Proc.Natl.Acad.Sci.USA 91:9564-9568.) can express vesicular stomatitis virus shell glycoprotein (VSVG).(American Type Culture Collection CRL-11268), produces the false type HIV-1 of VSVG Strain with pNL4.3.Env-.Luc and pHCMV-G cotransfection 293T cell.
With SupT1 cell (American Type Culture Collection, CRL-1942) inoculation 96 well culture plates, every hole 1 * 10
4Individual cell, with the false type HIV-1 of the above-mentioned VSVG of MOI (infection multiplicity)=1 inoculation virus, adding final concentration is the chemical compound that obtains among the embodiment 1 of 10 μ g/ml, puts 5%CO
2, cultivate 48h for 37 ℃, measure uciferase activity in the infection cell, the suppression ratio of calculation sample.Be the positive contrast of efavirenz (Efavirenz) of 10 μ g/ml with final concentration; Each experiment repeats calculating mean value 3 times.Chemical compound is as shown in table 2 to the suppression ratio result of HIV virus.
Table 2, chemical compound are to the suppression ratio (%) of HIV virus
As shown in Table 2, Compound P homopsone C of the present invention is, and HIV virus has good antiviral activity, suitable with existing anti HIV-1 virus pharmaceutical efavirenz effect, thereby can be for the preparation of antiviral drugs, this is apparent for a person skilled in the art.
Claims (2)
1. the application of a Phomopsone C is characterized in that, for the preparation of antiviral drugs.
2. application as claimed in claim 1 is characterized in that, described virus is HIV virus.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210044406 CN103284992A (en) | 2012-02-24 | 2012-02-24 | Application of Phomopsone C for preparing antiviral medicine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210044406 CN103284992A (en) | 2012-02-24 | 2012-02-24 | Application of Phomopsone C for preparing antiviral medicine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103284992A true CN103284992A (en) | 2013-09-11 |
Family
ID=49086885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201210044406 Pending CN103284992A (en) | 2012-02-24 | 2012-02-24 | Application of Phomopsone C for preparing antiviral medicine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103284992A (en) |
-
2012
- 2012-02-24 CN CN 201210044406 patent/CN103284992A/en active Pending
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Application publication date: 20130911 |