CN116283727A - Chaetoglobosin compound and preparation method and application thereof - Google Patents

Chaetoglobosin compound and preparation method and application thereof Download PDF

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CN116283727A
CN116283727A CN202310234239.4A CN202310234239A CN116283727A CN 116283727 A CN116283727 A CN 116283727A CN 202310234239 A CN202310234239 A CN 202310234239A CN 116283727 A CN116283727 A CN 116283727A
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chaetoglobosin
methanol
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ethyl acetate
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王斌贵
董昱良
李晓明
孟令红
王逸然
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Abstract

The invention relates to a microbial fermentation product and an application technology thereof in the field of medicine research, in particular to a preparation method and application of a chaetoglobosin compound produced by microbial fermentation. The chemical structure of the chaetoglobosin compound is shown as a formula I, and the chaetomium globosum is prepared by fermenting and culturing chaetomium globosum Chaetomium globosum. The in vitro anti-tumor activity test shows that the compound has remarkable anti-tumor activity, and in addition, the antibacterial activity test shows that the compound has stronger inhibitory activity on vibrio alginolyticus and is expected to be a medicament for treating cancer or vibrio alginolyticus infection. The chaetoglobosin compound prepared by the invention is produced by fermentation culture by utilizing microorganisms, and has the advantages of simple operation and production cycleShort period, low cost, etc.

Description

Chaetoglobosin compound and preparation method and application thereof
Technical Field
The invention relates to the technical field of microbial medicines, in particular to a chaetoglobosin compound obtained from a fermentation product of chaetomium globosum (Chaetomium globosum), and a preparation method and application thereof.
Background
The marine microorganism is in an extreme living environment for a long time, so that a unique metabolic pathway and physiological function are formed, and secondary metabolites with novel structures and obvious activities can be produced by metabolism. The chaetoglobosin compounds are cytochalasin compounds, have wide biological activities, such as anti-tumor, antibacterial, antiparasitic, anti-inflammatory, antiviral and other activities, and have wide application prospects.
Chaetomium globosum (Chaetomium globosum) is a saprophytic ascomycete widely distributed in a terrestrial, marine environment, the morphological characteristics and biological effects of which are well known in the art. The fungus can be isolated from a variety of sources, such as from the offshore Ulva pertusa (Cui C M et al, journal of Natural Products,2010,73 (4), 729-733), and from the Hypericum sampsonii (Huan Lijun, etc., chinese herbal medicine, 2020, 51 (3), 576-580); however, chaetomium globosum is often used as a biocontrol bacterium and plays an important role in preventing and controlling plant diseases.
Disclosure of Invention
The invention aims to provide a chaetoglobosin compound obtained from a fermentation product of chaetomium globosum (Chaetomium globosum), and a preparation method and application thereof.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a chaetoglobosin compound has a molecular structure shown in a formula I:
Figure BDA0004121444030000011
a preparation method of chaetoglobosin compounds,
1) Fermenting and culturing the activated mycelium of chaetomium globosum in a solid culture medium, repeatedly extracting a fermentation product with ethyl acetate, and combining the extracting solutions for concentrating to obtain a fermentation crude extract;
the chaetomium globosum (Chaetomium globosum) is reported in a plurality of documents, and a person skilled in the art can conveniently isolate the chaetomium globosum from the offshore ulva pertusa according to the method reported in the published documents (Cui C M et al Journal of Natural Products,2010,73 (4), 729-733), and can also isolate the chaetomium globosum from plants such as Hypericum sampsonii (Huan Lijun and the like, chinese herbal medicines 2020, 51 (3), 576-580); it is also available in flow-through manner at various collections, such as China center for type culture collection (China Center for Type Culture Collection, CCTCC, collection number CCTCC AF 2015035), american center for type culture collection (American Type Culture Collection, ATCC, collection numbers ATCC 16790 and ATCC 58917), german center for collection of microorganisms (Deutsche Sammlung von Mikroorganismen und Zellkulturen, DSMZ, collection numbers DSM 1962 and DSM 2142), and the like. In addition, registration information of the strain ITS in the gene library, such as NCBI (OP 848144.1), NCBI (OP 810867.1), etc., can also be conveniently obtained.
2) Subjecting the crude fermentation extract of step 1) to column chromatography on silica gel under reduced pressure, eluting with petroleum ether-ethyl acetate with a gradient of 20:1 to 1:1 (v/v) and dichloromethane-methanol with a gradient of 20:1 to 1:1 (v/v).
3) Petroleum ether-ethyl acetate 1 in step 2): the fractions eluted with a gradient of 1 (v/v) were purified by reverse phase column chromatography using methanol-water (10:90 to 100:0, v/v) as eluent;
4) Collecting methanol-water 70 in step 3): 30 (v/v) eluting the resulting fraction, separating by gel column chromatography, and then subjecting the fraction to semi-preparative liquid phase (78% CH) 3 CN/H 2 O,2.5 mL/min) and separating and purifying to obtain the compound shown in the formula I.
The method comprises the following steps:
1) Culturing the chaetomium globosum (Chaetomium globosum) on a PDA (potato sucrose agar) culture medium at 28 ℃ for 7 days, inoculating mycelium of the chaetomium globosum into a solid culture medium, standing and fermenting at room temperature for 39 days, extracting and removing small-polarity metabolites from a fermentation product by petroleum ether, fully soaking by ethyl acetate, repeatedly extracting for 4 times, and combining extract solutions for concentration to obtain a crude extract.
2) Subjecting the crude extract to reduced pressure silica gel column chromatography, and sequentially performing gradient elution by using petroleum ether-ethyl acetate and a dichloromethane-methanol elution system with the gradient of 20:1 to 1:1 (v/v, the same applies hereinafter) respectively.
3) Collecting the petroleum ether-ethyl acetate 1 in the step 2): 1, concentrating the eluted component, performing gradient elution through reversed phase silica gel column chromatography after concentrating, and performing gradient elution by using a methanol-water elution system with the gradient of 10:90 to 100:0;
4) Collecting the components of 70:30 of methanol-water in the step 3), separating by Sephadex LH-20 methanol gel column chromatography, and separating and purifying by semi-preparative liquid phase separation to obtain the chaetoglobosin compound shown in the formula I.
The application of the chaetoglobosin compound in the formula I in preparing human brain tumor medicaments, esophagus cancer medicaments, colon cancer medicaments, kidney cancer medicaments, bladder cancer medicaments and related lead compounds.
An application of chaetoglobosin compounds in preparing medicines for inhibiting vibrio alginolyticus infection is disclosed.
The invention has the advantages that:
1. the chaetoglobosin compound prepared by the invention is derived from fermentation products of chaetomium globosum (Chaetomium globosum), and the compound is prepared by adopting a microbial fermentation method, and has the characteristics of high efficiency and environmental protection.
2. Through in vitro anti-tumor activity test, the compound has the activity of obviously resisting SF126 human brain tumor cells, TE-1 human esophagus cancer cells, HCT116 human colon cancer cells, 786-O human kidney clear cell adenocarcinoma cells and 5637 human bladder cancer cells, and half inhibition concentration (IC 50 ) 7.17, 7.54, 7.19, 7.02 and 4.52 μm, respectively. In addition, the antibacterial activity test shows that the compound has strong inhibitory activity on vibrio alginolyticus, and the Minimum Inhibitory Concentration (MIC) is 0.5 mug/mL. The compound is a novel compound which has not been reported yet, can further explore the action mechanism of the compound, and can be used for developing a medicament or a lead compound for treating the diseases caused by the cancers and the vibrio alginolyticus infection.
Detailed Description
The invention will be further illustrated with reference to a few non-limiting examples of embodiments.
EXAMPLE 1 molecular Structure of Compounds
The structure of the chaetoglobosin compound separated from the chaetomium globosum (Chaetomium globosum) fermentation product is shown as a formula (I) (Arabic numerals in the formula represent carbon atom positions in the chemical structure):
Figure BDA0004121444030000031
EXAMPLE 2 preparation of Compounds of formula I
1) Fermentation culture
The chaetomium globosum (Chaetomium globosum) is inoculated with a proper amount of strain on a PDA plate, mycelium is white on a PDA (potato sucrose agar) culture medium, white spores are produced in the later stage, and the culture is carried out for 7 days at 28 ℃ for later use.
Inoculating the mycelium of the PDA plate into a sterile solid culture medium, standing and culturing at room temperature for 39 days, removing small polar metabolites from fermentation products by petroleum ether extraction, soaking and extracting for 4 times by using ethyl acetate, merging and concentrating to obtain a fermentation crude extract.
The formula of the solid culture medium is as follows: each 100 ml of seawater contains 70 g of rice, 0.1 g of corn steep liquor, 0.3 g of peptone and 0.05 g of methionine.
2) Crude extract separation and purification
The crude extract is subjected to column chromatography segmentation by a reduced pressure silica gel (100-200 meshes), and gradient elution is sequentially carried out by using petroleum ether-ethyl acetate with a gradient of 20:1 to 1:1 (20:1, 10:1, 5:1, 2:1, 1:1, v/v, and the same applies below) and dichloromethane-methanol with a gradient of 20:1 to 1:1 (20:1, 10:1, 5:1, 1:1) as eluting solvents; the fractions eluted from petroleum ether-ethyl acetate 1:1 were collected.
Subjecting the collected components to reverse phase silica gel column chromatography, and sequentially performing gradient elution with methanol-water of 10:90 to 100:0.
Collecting the components of 70:30 of methanol-water in the steps, separating by Sephadex LH-20 methanol gel column chromatography, separating and purifying by semi-prepared liquid phase, using 78% acetonitrile-water as a mobile phase, the flow rate is 2.5mL/min, and collecting an absorption peak with the retention time of 28min at 254nm wavelength to obtain a chaetoglobosin compound shown in a formula I;
compound 1 has the following physicochemical and spectral characteristics:
compound 1: pale yellow unshaped solid, chemical formula C 31 H 34 N 2 O 3 Specific optical rotation [ alpha ]]25D–75(c 0.04,MeOH)；UV(MeOH)λ max (logε)221(2.76),283(1.94)nm；ECD(1.24mM,MeOH)λ max (Δε)201(–3.12),236(+0.40),268(–0.54)；HR-ESI-MS m/z483.2647[M+H] + (calcd for C 31 H 35 N 2 O 3 ,483.2642)。 13 C-NMR 1 H-NMR is shown in Table 1.
TABLE 1 Compounds 1 13 C-NMR (125 MHz) and 1 H-NMR (500 MHz) data (test solvent: CDCl) 3 )
Figure BDA0004121444030000041
Figure BDA0004121444030000051
EXAMPLE 3 anti-tumor Activity assay
The following 5 test cell lines were selected: human brain tumor cells (SF 126), human esophageal cancer cells (TE-1), human colon cancer cells (HCT 116), human renal clear cell adenocarcinoma cells (786-O) and human bladder cancer cells (5637) were tested for anti-tumor activity; the cell lines used were all obtained by the normal route.
1) Test cell line and culture thereof
The test cell line adopted by the invention is human brain tumor cells (SF 126), human esophagus cancer cells (TE-1), human colon cancer cells (HCT 116), human kidney clear cell adenocarcinoma cells (786-O) and human bladder cancer cells (5637), and the cells are cultured in a culture solution containing 10% fetal bovine serum. All experiments used the same batch of cell lines between passage 2 and passage 10.
2) Preparation of the sample to be tested
The test sample is the pure compound shown in the formula I obtained in the above example, a proper amount of sample is accurately weighed, and cell-grade dimethyl sulfoxide (DMSO) is added for dissolving and mixing uniformly, and the concentration of the mother solution is 10mM. The cell culture medium was diluted to 10-fold the concentration to be tested for activity. The positive control cisplatin formulation was as above.
3) Cytotoxicity (CCK-8 method) assay:
the invention adopts the CCK-8 method to test the growth inhibition activity of tumor cells so as to evaluate the action effect of the compound.
The principle of the test method is as follows: the CCK-8 reagent contains 2- (2-Methoxy-4-nitrobenzene) -3- (4-nitrobenzene) -5- (2, 4-disulfophenyl) -2H-tetrazolium monosodium salt (WST-8), and is reduced into yellow Formazan product (Formazan) with high water solubility by dehydrogenase in cell mitochondria under the action of electron carrier 1-Methoxy-5-methylphenazine dimethyl sulfate (1-Methoxy PMS). The quantity of formazan generated is proportional to the quantity of living cells, dimethyl sulfoxide (DMSO) can dissolve the formazan deposited in the cells and has a maximum absorption peak at 450 nanometers, so that the absorption value of the formazan can be indirectly reflected by using an enzyme-labeled instrument at the wavelength of 450 nanometers, and the influence of a drug on cell proliferation can be evaluated.
The testing process comprises the following steps:
inoculating cells: cells were prepared as single cell suspensions with 10% fetal bovine serum in culture medium and 90 μl of 5×10 cells were inoculated per well in 96 well plates 4 Wall-attached cells/mL and 9X 10 4 Suspension cells in 5% CO/mL 2 Pre-culturing for 24 hours at 37 ℃.
Adding a sample solution to be tested: adding 10 mu L of sample solution into each hole, setting 1 concentration of each sample by an active primary screen, and setting 3 compound holes; IC (integrated circuit) 50 8 concentrations (containing 0 concentration) were measured, each concentration being provided with 3 multiplex wells; culturing in incubator for 48 hr. Experiment set-up Blank (Blank), control and Drug group (Drug))。
Color development: the adherent cells aspirate the old medium and drug solution (suspension cells were directly added to 10. Mu. LCCK-8 stock solution), 100. Mu.L CCK-8 solution diluted ten times per well was added at 37℃with 5% CO 2 Culturing was continued for 1-4 hours (operation in the dark, real-time observation).
And (3) detection: the absorbance at 450nm was measured with an enzyme-labeled instrument and the original data results were recorded.
Value added inhibition (IR%) calculation: OD values are averaged in three wells, excel software is applied to perform primary data standardization treatment, and a cell proliferation inhibition rate is calculated by the OD value of each well through preliminary screening (formula= (OD) Control -OD Drug )/(OD Control -OD Blank ) X 100%) and the inhibition rate was counted. IC (integrated circuit) 50 Calculated by GraphPad Prism 8 (version 8.0.2,GraphPad Software Inc), experimental results are expressed as ± SD.
IC 50 Value: the inhibition (IR%) was 50% of the corresponding sample solution concentration.
The experimental results are shown in Table 2.
TABLE 2 anti-tumor Activity of the examples obtained Compounds (IC 50 ,μM)
Figure BDA0004121444030000061
Experimental results show that the compound has stronger inhibitory activity on human brain tumor cells (SF 126), human esophageal cancer cells (TE-1), human colon cancer cells (HCT 116), human renal clear cell adenocarcinoma cells (786-O) and human bladder cancer cells (5637), and IC 50 The values are all less than 10 mu M, wherein the inhibition effect on human brain tumor cells (SF 126) is superior to the activity of positive control cisplatin.
EXAMPLE 4 antibacterial Activity
The activity of the compound shown in the formula I against vibrio alginolyticus (Vibro alginolyticus) is detected by adopting a Minimum Inhibitory Concentration (MIC) method.
The experimental procedure was as follows: sample solutions of different concentrations after dilution of the double ratio were added to sterile 96-well polystyrene plates, respectively, with 5 μl of sample solution per well for wells 1 to 8, and alternatively 1 column without sample as a growth control, using aseptic manipulation.
After diluting an indicator bacterium suspension corresponding to a turbidity of 0.5 McO by 1000 times with LB liquid medium (peptone 10g, yeast extract 5g, sodium chloride 10g, distilled water 1000 mL), 95. Mu.L was sequentially added to a 96-well plate so that the final concentrations of the samples from 1 st to 8 th wells were 64, 32, 16, 8, 4, 2, 1, 0.5. Mu.g/mL in this order. After gentle shaking and mixing, 96-well plates were sealed in a 37℃incubator and incubated for 24 hours.
The absorbance of each well was measured at a wavelength of 600nm using a microplate reader to completely inhibit the growth of the indicator bacteria in the wells at the minimum drug concentration MIC. The test is only meaningful when the indicator bacteria grow significantly in the negative control wells.
The experimental result shows that the compound has stronger inhibitory activity on vibrio alginolyticus, and the MIC is 0.5 mug/mL.
The experimental result proves that the compound has strong inhibition activity on a plurality of tumor cells and vibrio alginolyticus, can be used as an anti-tumor preparation or an antibacterial agent, and is expected to be applied to preparing related medicines in the form of any acceptable salt or clinically acceptable auxiliary materials or carriers such as excipient and diluent.

Claims (5)

1. A chaetoglobosin compound, characterized in that: the molecular structure of the compound is shown in formula I, and the molecular formula is C 31 H 34 N 2 O 3 ；
Figure FDA0004121444020000011
2. A method for preparing a chaetoglobosin compound according to claim 1, which is characterized in that:
1) Fermenting and culturing the activated mycelium of chaetomium globosum in a solid culture medium, repeatedly extracting a fermentation product with ethyl acetate, and combining the extracting solutions for concentrating to obtain a fermentation crude extract;
2) Subjecting the crude fermentation extract from step 1) to column chromatography on silica gel under reduced pressure, eluting sequentially with petroleum ether-ethyl acetate with a gradient of 20:1 to 1:1 (v/v) and dichloromethane-methanol with a gradient of 20:1 to 1:1 (v/v);
3) Petroleum ether-ethyl acetate 1 in step 2): the fractions eluted with a gradient of 1 (v/v) were purified by reverse phase column chromatography using methanol-water (10:90 to 100:0, v/v) as eluent;
4) Collecting methanol-water 70 in step 3): 30 (v/v) eluting the resulting fractions, separating them by gel column chromatography, and then subjecting them to semi-preparative liquid phase (78% CH) 3 CN/H 2 O,2.5 mL/min) and separating and purifying to obtain the compound shown in the formula I.
3. The method for preparing chaetoglobosin compounds according to claim 2, which is characterized in that:
1) Culturing the chaetomium globosum Chaetomium globosum on a PDA (potato sucrose agar) culture medium at 28 ℃ for 7 days, inoculating mycelia thereof into a rice solid culture medium, standing and fermenting at room temperature for 39 days, extracting a fermentation product by petroleum ether to remove small polar metabolites, fully soaking by ethyl acetate for repeated extraction, and concentrating the combined extract to obtain a crude extract;
2) Subjecting the crude extract to reduced pressure silica gel column chromatography, and sequentially performing gradient elution by using petroleum ether-ethyl acetate and a dichloromethane-methanol elution system with the gradient of 20:1 to 1:1 (v/v, the same applies below) respectively;
3) Collecting the petroleum ether-ethyl acetate 1 in the step 2): 1, concentrating the eluted component, performing gradient elution through reversed phase silica gel column chromatography after concentrating, and performing gradient elution by using a methanol-water elution system with the gradient of 10:90 to 100:0;
4) Collecting the components of 70:30 of methanol-water in the step 3), separating by Sephadex LH-20 methanol gel column chromatography, and separating and purifying by semi-preparative liquid phase separation to obtain the chaetoglobosin compound shown in the formula I.
4. Use of a chaetoglobosin class of compounds according to claim 1, characterized in that: the chaetoglobosin compound of the formula I is applied to medicaments for resisting human brain tumor, esophageal cancer, colon cancer, renal cancer and bladder cancer and related lead compounds.
5. Use of a chaetoglobosin class of compounds according to claim 1, characterized in that: the chaetoglobosin compound in the formula I is applied to the preparation of medicines for inhibiting vibrio alginolyticus infection.
CN202310234239.4A 2023-03-13 2023-03-13 Chaetoglobosin compound and preparation method and application thereof Pending CN116283727A (en)

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