CN113121551A - Metabolite of streptomyces pyroxyli and application - Google Patents
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- 241000187747 Streptomyces Species 0.000 title claims abstract description 18
- 239000002207 metabolite Substances 0.000 title abstract description 3
- 229930013930 alkaloid Natural products 0.000 claims abstract description 23
- -1 alkaloid compound Chemical class 0.000 claims abstract description 17
- 238000000855 fermentation Methods 0.000 claims abstract description 12
- 230000004151 fermentation Effects 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- LUHDREMZHBQHFC-MLIBEQFHSA-N Izumiphenazine A, (rel)- Chemical compound C1C2=NC3=CC=CC(O)=C3N=C2[C@@H](O)[C@H]2[C@@H]1C1=C3N=C4C(O)=CC=CC4=NC3=C(C(O)=O)C=C1O2 LUHDREMZHBQHFC-MLIBEQFHSA-N 0.000 claims abstract description 6
- LUHDREMZHBQHFC-UHFFFAOYSA-N izumiphenazine A Natural products OC1C2Oc3cc(C(O)=O)c4nc5cccc(O)c5nc4c3C2Cc2nc3cccc(O)c3nc12 LUHDREMZHBQHFC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000003797 alkaloid derivatives Chemical class 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000001963 growth medium Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000287 crude extract Substances 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- 238000012258 culturing Methods 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 241000191967 Staphylococcus aureus Species 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 3
- 238000011081 inoculation Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 2
- 241001537924 Tetracoccus <angiosperm> Species 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 241000500334 Tetragenococcus Species 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 241000894006 Bacteria Species 0.000 abstract description 2
- 241000970859 Streptomyces showdoensis Species 0.000 abstract description 2
- 241000191940 Staphylococcus Species 0.000 abstract 1
- 230000000813 microbial effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 244000052616 bacterial pathogen Species 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 239000013641 positive control Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 206010059866 Drug resistance Diseases 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RDEIXVOBVLKYNT-VQBXQJRRSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;(2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(aminomethyl)oxan-2-yl]o Chemical compound OS(O)(=O)=O.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)C(C)N)N)[C@@H](N)C[C@H]1N.O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N RDEIXVOBVLKYNT-VQBXQJRRSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000009629 microbiological culture Methods 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 206010048723 Multiple-drug resistance Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000010485 coping Effects 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 229930001119 polyketide Natural products 0.000 description 1
- 150000003881 polyketide derivatives Chemical class 0.000 description 1
- 230000001374 post-anti-biotic effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention requests to protect a metabolite of Streptomyces pyrophyllus and application, belongs to the technical field of microbial engineering, and particularly relates to an alkaloid compound, namely izumiphenazine A extracted from a Streptomyces pyrophyllus (Streptomyces showdoensis) liquid fermentation product, and a preparation method and application thereof. Specifically, the invention discloses an alkaloid compound, which has a chemical structural formula as follows:
Description
Technical Field
The invention relates to the field of biotechnology, in particular to a compound izumiphenazine A extracted from Streptomyces showdoensis liquid fermentation product, a preparation method thereof and an antibacterial activity application thereof.
Background
Antibiotics are often used to treat infections caused by minute pathogens and the like, making a significant contribution to human health. With the discovery of penicillin, antibiotic has become one of the greatest discoveries in the 20 th century, and the use of penicillin prolongs the average life of human beings by more than 15 years. However, in recent years, the drug resistance of pathogenic bacteria to antibiotics is more and more serious, even multiple drug resistance and cross drug resistance appear in some pathogenic bacteria, and the number of pathogenic bacteria with drug resistance also shows a rapid growth trend. If this problem cannot be solved as quickly as possible, we will likely enter the "post-antibiotic era" where no drugs are available. In order to avoid the health threat of human beings, the search for drug source compounds with new structural characteristics or new action characteristics becomes a main method for coping with the rapid change of pathogenic bacteria. The insect symbiotic bacteria have special metabolic pathways in the long-term evolution process with the host, and are valuable resource libraries for the research and development of novel antibiotics. Therefore, the isolation of antibacterial active substances of novel structure from insect-associated actinomycetes is one of the current means for combating pathogenic bacteria resistance.
Disclosure of Invention
The invention aims to solve the technical problem of providing an alkaloid compound, a preparation method and application thereof, namely the alkaloid compound serving as an antibacterial agent.
In order to solve the technical problems, the invention provides an alkaloid compound izumiphenazine A of streptomyces atrophaeus, which has the structural formula:
the streptomyces harynovii can be specifically a strain of China general microbiological culture Collection center (CGMCC 4.1757).
The invention also provides a preparation method of the alkaloid compound, which comprises the following steps:
1) inoculating streptomyces pyroxylinus into a Gao's first culture medium, and culturing for 3d in a constant-temperature incubator at 28 +/-0.5 ℃;
2) then inoculating fresh hypha into 100mL of an autoclaved liquid Gaoshi I culture medium, and culturing for 3d on a shaking table at the temperature of 28 +/-0.5 ℃ and the rotating speed of 180rpm to obtain a seed solution;
3) transferring the seed liquid into a fermentation culture medium according to the inoculation amount of 10-15%, and performing fermentation culture for 7d according to the shaking table condition in the step 1;
4) filtering the fermentation liquor obtained in the step 3, extracting the filtrate with ethyl acetate, and performing vacuum concentration and drying to obtain a crude extract;
5) preparing a silica gel column by using the crude extract obtained in the step (4) and silica gel with the mass being 10 times that of the crude extract, eluting with pure dichloromethane at the beginning, and then sequentially eluting with dichloromethane and methanol with the ratio of 100:1, 100:2 and 100:4 to obtain different elution parts;
6) drying the elution part 100:1 in the step 5, and then separating by gel column chromatography, taking methanol as an eluent, and recrystallizing the obtained precipitate in methanol; obtaining the alkaloid compound.
The invention also provides the application of the alkaloid compound in the antibacterial agent, which comprises the following specific steps: is used for inhibiting the growth of pathogenic bacteria such as Staphylococcus aureus and Tetragenococcus.
The invention has the following beneficial effects:
1. the alkaloid compounds of the present invention can be used as antibacterial agents or their precursors.
2. The alkaloid compound can be produced by liquid fermentation by using microorganisms, and has the advantages of simple process, short period, low cost and guaranteed source.
3. The invention utilizes the biological method to synthesize the alkaloid compound, and has no pollution to the environment.
Detailed Description
The invention is further explained below with reference to specific embodiments.
Example 1 liquid fermentation of Streptomyces Clariticus
The Streptomyces pyroxyli strain (with the preservation number of CGMCC4.1757) is obtained from China general microbiological culture Collection center, inoculated into a Gao's No. I culture medium, and cultured in a constant temperature incubator at 28 +/-0.5 ℃ for 3 days; inoculating fresh hypha into 100mL of autoclaved liquid Gaoshi I culture medium, and culturing for 3d on a shaking table at the temperature of 28 +/-0.5 ℃ and the rotating speed of 180rpm to obtain seed liquid; transferring the seed liquid into a fermentation culture medium according to the inoculation amount of 10% -15%, and culturing for 7d on a shaking table with the temperature of 28 +/-0.5 ℃ and the rotating speed of 180 rpm.
Example 2 extraction and isolation of Alkaloids of Streptomyces Clarithrombus
Filtering 20L of fermentation liquor prepared in example 1 by using 3 layers of gauze to obtain filtrate, extracting the filtrate for several times by using a medium-polarity organic solvent ethyl acetate in a ratio of 1:1 until no extract is obtained in an organic phase, combining all extraction solutions, and concentrating the combined extraction solutions at high pressure by using a rotary evaporator to obtain 9.5g of a crude extract of a corresponding strain; uniformly mixing the crude extract with silica gel of equal mass of 100-200 meshes, drying the sample in a drying oven at 40 ℃, and further grinding the sample into powder for later use; silica gel column is prepared by using silica gel with 10 times mass of crude extract, and dichloromethane and methanol with different proportions are used as eluent to elute from low polarity to high polarity. Eluting with pure dichloromethane, sequentially eluting with dichloromethane-methanol ratio of 100:1, 100:2, and 100:4 (each eluent is about 10 times column volume), drying, separating by gel column chromatography, eluting with methanol, and recrystallizing to obtain polyketide 45 mg. The structural formula is as follows:
example 3 identification of alkaloid Compound Structure of Streptomyces Cladosporus
The structure of the alkaloid compounds of the streptomyces pyrophyllus is determined based on the analysis of the characteristics, mass spectrum and nuclear magnetic resonance spectrum data of the alkaloid compounds. The trait and spectroscopy data are as follows:
red amorphous powder, easily soluble in dimethyl sulfoxide. The nmr spectroscopic data for the compounds are as follows: 1H NMR (DMSO-d6) Δ:3.69(1H, dd,7.2Hz14.8Hz),4.19(1H, dd,6.5Hz14.8Hz),4.80(1H, m),5.34(1H, dd,3.3Hz 6.1Hz),5.59(1H, dd,6.1Hz10.4Hz),6.33(1H, d,3.3Hz),7.11(1H, d,7.9Hz),7.32(1H, d,7.7Hz),7.38(1H, d,7.9Hz),7.59(1H, t,7.9Hz),7.71(1H, d,7.7Hz),7.81(1H, t,7.7Hz),8.12(1H, s),10.30(1H, s),10.77(1H, s), 1H, 14.34H, 14 brs); 13CNMR (DMSO-d6) delta 33.3,39.1,39.2,39.4,39.5,39.6,39.8,39.9,71.5,88.6,111.6,111.7,118.0,118.3,130.5,131.2,137.3,138.7,142.2,149.7,153.1,153.4,153.5,158.7,165.7.
Example 3 inhibitory Effect of Alkaloids of Streptomyces Clarkensis on pathogenic bacteria
And (3) carrying out antibacterial activity test on the alkaloid compound of the streptomyces adonnans by adopting a filter paper method. Three kinds of pathogenic bacteria are inoculated in PDA liquid culture medium and cultured on a shaking table at 30 ℃ and 180r/min overnight. Then, the concentration of the bacterial liquid is adjusted to 0.5-1 McLee by using sterile water. Compounds and positive controls (gentamicin) were formulated with DMSO at a concentration of 6 mg/mL. Under the aseptic condition, a pipette is used for sucking 200 mu L of diluted bacterial suspension, the diluted bacterial suspension is sprayed on a PDA solid plate and is evenly coated, then a pipette is used for sucking 5 mu L of prepared compound and positive control solution, the compound and the positive control solution are respectively dripped on sterile filter paper sheets with the diameter of 5mm, after DMSO is volatilized to be dry, the filter paper sheets are placed in the center of the plate which is fully coated with pathogenic bacteria, the culture dish is placed in a constant temperature culture box in an inverted mode to be incubated for about 24 hours,
the growth inhibitory effect of alkaloids on pathogenic bacteria is shown in table 1 below. As can be seen from the data in the table, when the test concentration is 90 mug/filter paper, the diameter of the inhibition zone for staphylococcus aureus is 13 +/-1.2 mm, and the activity is slightly weaker than that of positive control gentamicin sulfate (19.2 +/-2.8 mm); the alkaloid compounds have weak activity on Escherichia coli and Tetragenococcus, and the diameters of inhibition zones are less than 12 mm.
TABLE 1 growth inhibition (mm) of pathogenic bacteria by alkaloid compounds of Streptomyces Cladosporus
Note: results are expressed as the standard for ± 3 parallel measurements of zone diameter; gentamicin sulfate is a positive control of pathogenic bacteria; the test concentration was 90. mu.g/filter paper sheet.
Finally, it is also noted that the above-mentioned lists merely illustrate a few specific embodiments of the invention. It is obvious that the invention is not limited to the above embodiments, but that many variations are possible. All modifications which can be derived or suggested by a person skilled in the art from the disclosure of the present invention are to be considered within the scope of the invention.
Claims (3)
1. An alkaloid compound izumiphenazine A of streptomyces pyrophyllus is characterized in that the structural formula is as follows:
2. the process for preparing the Streptomyces pyroxylensis compound izumiphenazine A according to claim 1, which comprises the steps of:
1) inoculating streptomyces pyroxylinus into a Gao's first culture medium, and culturing for 3d in a constant-temperature incubator at 28 +/-0.5 ℃;
2) then inoculating fresh hypha into 100mL of an autoclaved liquid Gaoshi I culture medium, and culturing for 3d on a shaking table at the temperature of 28 +/-0.5 ℃ and the rotating speed of 180rpm to obtain a seed solution;
3) transferring the seed liquid into a fermentation culture medium according to the inoculation amount of 10-15%, and performing fermentation culture for 7d according to the shaking table condition in the step 1;
4) filtering the fermentation liquor obtained in the step 3, extracting the filtrate with ethyl acetate, and performing vacuum concentration and drying to obtain a crude extract;
5) preparing a silica gel column by using the crude extract obtained in the step (4) and silica gel with the mass being 10 times that of the crude extract, eluting with pure dichloromethane at the beginning, and then sequentially eluting with dichloromethane and methanol with the ratio of 100:1, 100:2 and 100:4 to obtain different elution parts;
6) drying the elution part 100:1 in the step 5, and then separating by gel column chromatography, taking methanol as an eluent, and recrystallizing the obtained precipitate in methanol; obtaining the alkaloid compound.
3. Use of the novel compounds according to claim 1, characterized in that: has antagonistic activity against Staphylococcus aureus and Tetracoccus.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115287236A (en) * | 2022-08-15 | 2022-11-04 | 安徽农业大学 | Preparation method and application of alkaloid compound from insect symbiotic actinomycetes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011178734A (en) * | 2010-03-02 | 2011-09-15 | Chiba Univ | Izumiphenazine a |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011178734A (en) * | 2010-03-02 | 2011-09-15 | Chiba Univ | Izumiphenazine a |
Non-Patent Citations (1)
| Title |
|---|
| ABDELFATTAH, MOHAMED S.: "Izumiphenazines A-C: Isolation and structure elucidation of phenazine derivatives from Streptomyces sp. IFM 11204" * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115287236A (en) * | 2022-08-15 | 2022-11-04 | 安徽农业大学 | Preparation method and application of alkaloid compound from insect symbiotic actinomycetes |
| CN115287236B (en) * | 2022-08-15 | 2023-08-11 | 安徽农业大学 | Preparation method and application of alkaloid compounds derived from insect symbiotic actinomycetes |
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Application publication date: 20210716 |