CN102872055B - Application of gypensapogenin B in anti-tubercle bacillus drugs - Google Patents
Application of gypensapogenin B in anti-tubercle bacillus drugs Download PDFInfo
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- CN102872055B CN102872055B CN201210418608.7A CN201210418608A CN102872055B CN 102872055 B CN102872055 B CN 102872055B CN 201210418608 A CN201210418608 A CN 201210418608A CN 102872055 B CN102872055 B CN 102872055B
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- gypensapogenin
- tubercle bacillus
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- tuberculosis
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- NNUMQZNZQGQGCN-AGHUFMIKSA-N gypensapogenin b Chemical compound O=C1C(=C(C)C)CC([C@@H]2[C@@H]3[C@@]([C@@]4(CCC5=C([C@H]6CC[C@H](O6)C5(C)C)[C@H]4CC3)C)(C)CC2)=C1 NNUMQZNZQGQGCN-AGHUFMIKSA-N 0.000 title claims abstract description 73
- 241000193830 Bacillus <bacterium> Species 0.000 title claims abstract description 25
- 239000003814 drug Substances 0.000 title claims abstract description 14
- 229940079593 drug Drugs 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 10
- 241000187479 Mycobacterium tuberculosis Species 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- 230000001629 suppression Effects 0.000 abstract 2
- 206010060976 Bacillus infection Diseases 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 201000008827 tuberculosis Diseases 0.000 description 12
- 239000001963 growth medium Substances 0.000 description 11
- 239000002609 medium Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229960000190 bacillus calmette–guérin vaccine Drugs 0.000 description 9
- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 6
- 206010059866 Drug resistance Diseases 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 230000002365 anti-tubercular Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 240000006509 Gynostemma pentaphyllum Species 0.000 description 3
- 235000002956 Gynostemma pentaphyllum Nutrition 0.000 description 3
- 241001467552 Mycobacterium bovis BCG Species 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 230000010355 oscillation Effects 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 229930182490 saponin Natural products 0.000 description 3
- 150000007949 saponins Chemical class 0.000 description 3
- 235000017709 saponins Nutrition 0.000 description 3
- 238000007790 scraping Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 150000003648 triterpenes Chemical class 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 235000003143 Panax notoginseng Nutrition 0.000 description 1
- 241000180649 Panax notoginseng Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000036981 active tuberculosis Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- OORMXZNMRWBSTK-UHFFFAOYSA-N dammaran Natural products C1CCC(C)(C)C2CCC3(C)C4(C)CCC(C(C)CCCC(C)C)C4CCC3C21C OORMXZNMRWBSTK-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960000285 ethambutol Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229960003350 isoniazid Drugs 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Abstract
The invention discloses application of gypensapogenin B to preparation of anti-tubercle bacillus drugs. According to the high tubercle bacillus morbidity and the emergence of mycobacterium tuberculosis multiple-resistant strain, the tubercle bacillus morbidity and mortality are one the rise; and gypensapogenin B has remarkable tubercle bacillus suppression activity and good application prospect. The application of gypensapogenin B to the preparation of the anti-tubercle bacillus drugs is firstly publicized, the skeleton type is brand-new, the tubercle bacillus suppression activity is unexpectedly strong and the possibility of giving any revelation by other compounds does not exist, so that prominent substantive features are provided and a remarkable progress in the prevention and treatment of the tubercle bacillus infection is made at the same time.
Description
Technical field
The present invention relates to medical compounds application, be specifically related to Gypensapogenin B in the application of preparing in anti-tubercle bacillus drugs.
Background technology
Global morbidity lungy is in recent years increases trend, according to the World Health Organization (WHO), estimate, the population that the whole world is infected by mycobacterium tuberculosis (Mycobacterium tuberculosis, MTB) at present accounts for 1/3rd of world population, and wherein the infected of 5 ~ 10% becomes tuberculosis patient.There are every year active tuberculosis patient 1,300,000 examples in China, wherein infectiousness pulmonary tuberculosis approximately 600,000 examples, and wherein infectiousness pulmonary tuberculosis approximately 600,000 examples, are one of the high burden of global tuberculosis countries.
From antituberculotics, come out one after another, make treatment lungy play epoch-making variation.But due to still standard very not of the treatment management of tuberculosis patient, irregular chemotherapy, abuse antituberculotics, makes drug resistance of tuberculosis situation day by day serious, and the variation of drug resistance more trends towards multi-medicament drug resistance simultaneously, and this causes very big difficulty to preventing and controlling lungy.Therefore find new antituberculotics, the antituberculotics of especially anti-multidrug resistance is to protection people's health, significant.
Summary of the invention
The compound Gypensapogenin B the present invention relates to is one and within 2012, delivers (Li, N. et al., 2012. Triterpenes possessing an unprecedented skeleton isolated from hydrolyzate of total saponins from Gynostemma pentaphyllum. European Journal of Medicinal Chemistry 50, 173 – 178.) New skeleton compound, this compound has brand-new framework types, current purposes only relates to the cytotoxic activity (Li of human tumor cell line, N. et al., 2012. Triterpenes possessing an unprecedented skeleton isolated from hydrolyzate of total saponins from Gynostemma pentaphyllum. European Journal of Medicinal Chemistry 50, 173 – 178.), purposes for the Gypensapogenin B the present invention relates in preparation treatment anti-tubercle bacillus drugs belongs to open first, because framework types belongs to brand-new framework types, and it suppresses active unexpectedly strong for tulase, there is not the possibility that is provided any enlightenment by other compounds, possesses outstanding substantive distinguishing features, for the control of tubercle bacillus affection, obviously there is significant progress simultaneously.
Summary of the invention
The object of the invention is to, according to not finding that it has the present situation of the report of tuberculosis activity in existing Gypensapogenin B research, provides Gypensapogenin B in the application of preparing in anti-tubercle bacillus drugs.
Described compound Gypensapogenin B structure is as shown in formula I:
The object of the invention is achieved by the following technical programs:
Inventor first does examination bacterial strain with bacillus calmette-guerin vaccine, adopt disk diffusion method to carry out preliminary test to the anti-tubercle bacillus activity of Gypensapogenin B, according to the result of preliminary test, the present invention use again solid medium By Dilution this compound to bacillus calmette-guerin vaccine, the minimal inhibitory concentration of three kinds of tulases of the H37Rv strain of mycobacterium tuberculosis type strain and substance of medicines-resistant branched tubercle bacillus (MDR MTB), experimental result confirms that Gypensapogenin B has very strong anti-tubercle bacillus and anti-drug resistance tulase activity, can be used as the lead compound for the treatment of tubercle bacillus affection disease, also can be used for preparation treatment tuberculosis medicine.
Compared with prior art, the present invention has following beneficial effect:
1. the invention provides a kind of Gypensapogenin B that can be used for the sick treatment of tuberculosis, thereby expanded the kind of anti-tubercle bacillus drugs;
2. the appearance of, tubercule bacillus multiple antibiotic resistant strain high for current incidence of tuberculosis and HIV (human immunodeficiency virus) double infection, make incidence of tuberculosis and mortality rate present situation in rising trend, the present invention finds that Gypensapogenin B has the feature of anti-tubercle bacillus and drug resistance tulase activity, can be used for the preparation of antituberculotics, there is boundless application prospect;
3. the purposes of the Gypensapogenin B the present invention relates in preparation treatment anti-tubercle bacillus drugs belongs to open first, because framework types belongs to brand-new framework types, and it suppresses active unexpectedly strong for tulase, there is not the possibility that is provided any enlightenment by other compounds, possess outstanding substantive distinguishing features, for the control of tubercle bacillus affection, obviously there is significant progress simultaneously.
The specific embodiment
The preparation method of compound Gypensapogenin B involved in the present invention is referring to document (Li, N. et al., 2012. Triterpenes possessing an unprecedented skeleton isolated from hydrolyzate of total saponins from Gynostemma pentaphyllum. European Journal of Medicinal Chemistry 50, 173 – 178. and Wei, J.X. et al., 1982. Two new dammaran sapogenins from leaves of Panax notoginseng. Planta Medica, 45 (3): 167-171.).
The present invention is further detailed explanation by the following examples, but protection scope of the present invention is not subject to any restriction of specific embodiment, but be limited by claim.
Embodiment 1: the preparation of compound Gypensapogenin B tablet involved in the present invention:
Get 20 and digest compound Gypensapogenin B, add 180 grams of conventional adjuvants preparing tablet, mix, conventional tablet machine is made 1000.
Embodiment 2: the preparation of compound Gypensapogenin B capsule involved in the present invention:
Get 20 and digest compound Gypensapogenin B, add the conventional adjuvant of preparing capsule as 180 grams of starch, mix, encapsulatedly make 1000.
Below by pharmacodynamic experiment, further illustrate its pharmaceutically active.
The experimental example 1 anti-bacillus calmette-guerin vaccine of solid medium By Dilution Gypensapogenin B (BCG) absolute concentration
Scraping bacillus calmette-guerin vaccine culture from inclined-plane, join in 3ml Middlebrook7H9 broth bouillon, add a small amount of bead, screw test tube cap, on vortex oscillation device, high vibration grinds, than turbid, be made into bacillus calmette-guerin vaccine (BCG) bacteria suspension of 1mg/ml with standard Maxwell opacity tube (MacFarland No.1).
Gypensapogenin B is made into the stock solution of high concentration with DMSO, with containing the aseptic ultra-pure water dilution of 5% tween 80 stock solution to desired concn, the Gypensapogenin B having diluted is joined to 4ml Middlebrook7H11 agar culture medium (121 ℃ of high pressure steam sterilizations 15 minutes of this culture medium by required dosage, be cooled to 50 ~ 55 ℃), mix, make containing Gypensapogenin B, concentration is respectively 6.0 ug/ml, 4.0 ug/ml, 3.0 ug/ml, 2.0 ug/ml, 1.5 ug/ml, 1.0 ug/ml, 0.75 ug/ml, the isocyatic slant medium of 0.5 ug/ml.
Bacillus calmette-guerin vaccine (BCG) the bacteria suspension inoculating loop that is 1 mg/ml by concentration dips ring of numbers, be inoculated in respectively in the culture medium and blank medium slant containing Gypensapogenin B series concentration, be placed in 37 ℃ and cultivate 4 ~ 8 weeks, observation experiment result, result is as shown in table 1.
In the present embodiment Middlebrook7H9 broth bouillon used and Middlebrook7H11 agar culture medium be those skilled in the art carry out tulase cultivate time conventional culture medium, its formula adopt conventional formulation.
Experimental example 2 solid medium By Dilution Gypensapogenin B Killing Mycobacterium Tuberculosis type strain H37Rv strain absolute concentrations
Scraping mycobacterium tuberculosis type strain H37Rv strain culture from inclined-plane, join in 3 ml Middlebrook7H9 broth bouillons, add a small amount of bead, screw test tube cap, on vortex oscillation device, high vibration grinds, than turbid, be made into the H37Rv strain bacteria suspension of 1 mg/ml with standard Maxwell opacity tube (MacFarland No.1).
Gypensapogenin B is made into respectively to the stock solution of high concentration with DMSO, with containing the aseptic ultra-pure water dilution of 5% tween 80 stock solution to desired concn, the Gypensapogenin B having diluted is joined to 4ml Middlebrook7H11 agar culture medium (121 ℃ of high pressure steam sterilizations 15 minutes of this culture medium by required dosage, be cooled to 50 ~ 55 ℃), mix, make containing Gypensapogenin B, concentration is respectively 6.0 ug/ml, 4.0 ug/ml, 3.0 ug/ml, 2.0 ug/ml, 1.5 ug/ml, 1.0 ug/ml, 0.75 ug/ml, the isocyatic slant medium of 0.5 ug/ml.
The H37Rv strain bacteria suspension that is 1mg/ml by concentration dips ring of numbers with inoculating loop, is inoculated in respectively in the culture medium and blank medium slant containing Gypensapogenin B series concentration, and be placed in 37 ℃ and cultivate 4 ~ 8 weeks, observation experiment result, result is as shown in table 1.
The clinical separation of the experimental example 3 solid medium By Dilution Gypensapogenin B tuberculosis mycobacterium MTB of resistance to ISRE strain absolute concentration
The clinical separation of the scraping mycobacterium tuberculosis MTB of resistance to ISRE strain (resistance to isoniazid, streptomycin, rifampicin, the clinical detached dowel of ethambutol mycobacterium tuberculosis) culture from inclined-plane, join in 3ml Middlebrook7H9 broth bouillon, add a small amount of bead, screw test tube cap, on vortex oscillation device, high vibration grinds, than turbid, be made into the bacteria suspension of 1mg/ml with standard Maxwell opacity tube (MacFarland No.1).
Gypensapogenin B is made into respectively to the stock solution of high concentration with DMSO, with containing the aseptic ultra-pure water dilution of 5% tween 80 stock solution to desired concn, the Gypensapogenin B having diluted is joined to 4ml Middlebrook7H11 agar culture medium (121 ℃ of high pressure steam sterilizations 15 minutes of this culture medium by required dosage, be cooled to 50 ~ 55 ℃), mix, make containing Gypensapogenin B, concentration is respectively 6.0 ug/ml, 4.0 ug/ml, 3.0 ug/ml, 2.0 ug/ml, 1.5 ug/ml, 1.0 ug/ml, 0.75 ug/ml, the isocyatic slant medium of 0.5 ug/ml.
The clinical separation of the mycobacterium tuberculosis MTB of the resistance to ISRE strain bacteria suspension that is 1mg/ml by concentration dips ring of numbers with inoculating loop, be inoculated in respectively in the culture medium and blank medium slant containing Gypensapogenin B series concentration, being placed in 37 ℃ cultivates 4 ~ 8 weeks, observation experiment result, result is as shown in table 1.
Table 1 solid medium By Dilution Gypensapogenin B anti-tubercle bacillus absolute concentration result
Conclusion: Gypensapogenin B has very strong anti-tubercle bacillus and anti-drug resistance tulase activity, can be used as the lead compound for the treatment of tubercle bacillus affection disease, also can be used for preparation treatment tuberculosis medicine.
Claims (1)
1.Gypensapogenin B is in the application of preparing in anti-tubercle bacillus drugs, described compound Gypensapogenin B structure as
formula Ishown in:
formula I.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210418608.7A CN102872055B (en) | 2012-10-26 | 2012-10-26 | Application of gypensapogenin B in anti-tubercle bacillus drugs |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210418608.7A CN102872055B (en) | 2012-10-26 | 2012-10-26 | Application of gypensapogenin B in anti-tubercle bacillus drugs |
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| Publication Number | Publication Date |
|---|---|
| CN102872055A CN102872055A (en) | 2013-01-16 |
| CN102872055B true CN102872055B (en) | 2014-04-16 |
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| CN201210418608.7A Active CN102872055B (en) | 2012-10-26 | 2012-10-26 | Application of gypensapogenin B in anti-tubercle bacillus drugs |
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| Country | Link |
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| CN (1) | CN102872055B (en) |
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2012
- 2012-10-26 CN CN201210418608.7A patent/CN102872055B/en active Active
Non-Patent Citations (2)
| Title |
|---|
| Ning Li,et al.Triterpenes possessing an unprecedented skeleton isolated from hydrolyzate of total saponins from Gynostemma pentaphyllum.《European Journal of Medicinal Chemistry》.2012,(第50期), |
| Triterpenes possessing an unprecedented skeleton isolated from hydrolyzate of total saponins from Gynostemma pentaphyllum;Ning Li,et al;《European Journal of Medicinal Chemistry》;20120203(第50期);173－178 * |
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| CN102872055A (en) | 2013-01-16 |
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