CN110776518A - Azaphilone spiro compounds and preparation method and application thereof - Google Patents
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Abstract
The invention discloses Azaphilone spiro compounds and a preparation method and application thereof, belonging to the technical field of microorganisms. The Azaphilone spiro-compound has the structural formula
Description
Technical Field
The invention relates to an Azaphilone spiro compound and a preparation method and application thereof, belonging to the technical field of microorganisms.
Background
The plant endophytic fungi have strong biosynthesis capacity and are an important source of medicine lead compounds, but under pure culture conditions, a plurality of gene clusters are in a silent state and are not expressed to produce corresponding products. Recent researches show that the chemical epigenetic modification method can inhibit enzymes influencing epigenetic inheritance in fungi through small molecular chemical substances, activate silent biosynthesis genes, induce the fungi to generate new active compounds and increase the structural diversity of secondary metabolites of strains.
The phomopsis is a common group in endophytic fungi of plants, the secondary metabolites of the phomopsis are various in structure type and have various biological activities, and the phomopsis has higher research value for finding a medicinal lead compound from a microorganism source. To date, no research report on the application of a chemical epigenetic modification method to secondary metabolites of phomopsis fungi is available.
Disclosure of Invention
Aiming at the problem that a chemical epigenetic modification method is used for secondary metabolites of phomopsis fungi in the prior art, the invention provides an Azaphilone spiro-compound and a preparation method and application thereof.
The Azaphilone spiro-compound has a structural formula shown in a formula (I),
the invention utilizes a chemical epigenetic modifier nicotinamide to modify a phomopsis strain YE3250, and extracts an Azaphilone spiro-compound from a fermentation product of the phomopsis strain YE 3250.
The Phomopsis strain YE3250 is derived from a Paeonia yunnanensis (Paeonia delavayi Franch) plant, and a endophytic fungus Phomopsis sp.YE3250 strain which is preserved in China center for type culture Collection in 2012, 9 and 19, and has a preservation number of CCTCC No. M2012364 and is disclosed in a patent with an application number of 201210415385.9.
The preparation method of the Azaphilone spiro-compound comprises the following specific steps:
(1) inoculating Phomopsis sp.YE3250 strain into PDB culture medium, and shake culturing at 28 + -2 deg.C for 3-5 d to obtain fungus seed liquid;
(2) dissolving a chemical epigenetic modifier nicotinamide in sterile water, and filtering by a microporous filter membrane to obtain a nicotinamide solution;
(3) adding the nicotinamide solution obtained in the step (2) into a PDB fermentation culture medium to obtain a PDB fermentation culture medium containing a chemical epigenetic modifier, inoculating a fungus seed solution into the PDB fermentation culture medium, and performing shake culture at the temperature of 28 +/-2 ℃ for 7-9 days to obtain a fermentation mixture;
(4) and (3) filtering the fermentation mixture obtained in the step (3) to obtain fermentation liquor and mycelium, extracting the fermentation liquor by using ethyl acetate to obtain ethyl acetate extract, extracting the mycelium by using ethanol to obtain ethanol extract, combining the ethyl acetate extract and the ethanol extract, concentrating under reduced pressure to obtain a fermentation crude extract, and separating and purifying the fermentation crude extract by using column chromatography to obtain the Azaphilone spiro-compound.
Further, the PDB culture medium in the step (1) comprises potatoes, glucose and distilled water, wherein the concentration of the potatoes in the PDB culture medium is 0.2-0.4 g/mL, and the concentration of the glucose in the PDB culture medium is 0.02-0.05 g/mL.
Further, the concentration of nicotinamide in the nicotinamide solution in the step (2) is 400-600 mM.
Further, the PDB fermentation medium is the same as the PDB medium in the step (1).
Furthermore, the concentration of nicotinamide in the PDB fermentation medium containing the chemical epigenetic modifier is 200-300 mu M.
Further, the inoculation amount of the fungus seed liquid in the step (3) is 5-10%.
The Azaphilone spiro compound is applied to preparation of medicines for preventing and treating diabetes or antifungal agricultural antibiotics.
The plant endophytes are planted and operated in plant tissues, form a reciprocal symbiotic relationship with plants, have no harm to the plant bodies and even are beneficial to the survival of the plants; therefore, bioactive molecules from plant endophytes are equivalent to the bioactive molecules screened by plants, and have the characteristic of low toxicity; the Azaphilone spiro compound is obtained from medicinal plant endophytes, and has low toxicity in the aspect of preparing medicines.
The invention has the beneficial effects that:
the invention utilizes a chemical epigenetic modifier nicotinamide to modify a phomopsis strain YE3250, and extracts an Azaphilone spiro-compound from a fermentation product of the phomopsis strain YE 3250; the Azaphilone spiro compound can be used for preparing medicines for preventing and treating diabetes or antifungal agricultural antibiotics.
Drawings
FIG. 1 is a high resolution mass spectrum of the Azaphilone spiro compound of example 1;
FIG. 2 shows the NMR spectrum of the Azaphilone spiro compound of example 1;
FIG. 3 shows the NMR carbon spectrum of the Azaphilone spiro-compound of example 1.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments, but the scope of the present invention is not limited to the description.
Example 1: the Azaphilone spiro-compound has a structural formula shown in a formula (I),
the preparation method of the Azaphilone spiro-compound comprises the following specific steps:
(1) preparing a PDB culture medium: peeling potato, cutting into small pieces, adding distilled water, boiling, filtering with warp cloth to obtain potato filtrate, adding glucose, sterilizing at 121 deg.C for 30min to obtain PDB culture medium with potato concentration of 0.2g/mL and glucose concentration of 0.02 g/mL;
inoculating Phomopsis sp.YE3250 strain of Phomopsis into PDB culture medium, and shake culturing at 28 + -2 deg.C and 200r/min for 4d to obtain fungus seed solution;
(2) dissolving a chemical epigenetic modifier nicotinamide in sterile water, and filtering by a microporous filter membrane with the aperture of 0.22 mu m to obtain a nicotinamide solution; wherein the concentration of nicotinamide in the nicotinamide solution is 400 mM;
(3) adding the nicotinamide solution obtained in the step (2) into a PDB fermentation culture medium to obtain a PDB fermentation culture medium containing a chemical epigenetic modifier, inoculating a fungus seed solution into the PDB fermentation culture medium, and performing shake culture at the temperature of 28 +/-2 ℃ and the rotating speed of 200r/min for 7-9 days to obtain a fermentation mixture; wherein the PDB fermentation culture medium is the same as the PDB culture medium in the step (1), the concentration of nicotinamide in the PDB fermentation culture medium containing the chemical epigenetic modifier is 200 mu M, and the inoculation amount of the fungus seed liquid is 10 percent;
(4) filtering the fermentation mixture obtained in the step (3) to obtain fermentation liquor and mycelia, extracting the fermentation liquor with ethyl acetate to obtain ethyl acetate extract, extracting the mycelia with ethanol to obtain ethanol extract, mixing the ethyl acetate extract and the ethanol extract, concentrating under reduced pressure to obtain fermentation crude extract, separating and purifying the fermentation crude extract by column chromatography (silica gel column 200-300 meshes) to obtain Azaphilone spiro compounds, performing gradient elution with a chloroform-methanol solvent system from 1:0 to 0:1, collecting the elution components of chloroform-methanol 9:1 to 85:15, concentrating under reduced pressure, performing silica gel column chromatography on the concentrated solution, performing gradient elution with petroleum ether-ethyl acetate, collecting the elution components of petroleum ether-ethyl acetate 8:2 to 7:3, performing RP-18 reverse phase silica gel column chromatography, performing gradient elution with a methanol-water solvent system from 4:6 to 7:3, collecting the eluted components of methanol-water 6:4, and preparing the Azaphilone spiro compound by decompression and concentration;
the Azaphilone spiro compound is white powder, is dissolved in organic solvent such as chloroform, acetone, methanol, etc., is insoluble in petroleum ether and water, and has high resolution mass spectrum as shown in FIG. 1, and molecular ion peak is HRESIMS M/z427.1374[ M + Na ]]
+(calcd forC
21H
24O
8Na,427.1369), molecular formula is C
21H
24O
8；
The NMR spectrum of the Azaphilone spiro compound is shown in figure 2, the NMR spectrum of the Azaphilone spiro compound is shown in figure 3, and the NMR data tested by the structural analysis of the compound are as follows:
1H NMR(500MHz,CD
3OD)δ6.15(1H,s,H-5'),6.13(1H,s,H-3'),5.58(1H,d,J＝2.8Hz,H-6),4.45(1H,brd,J＝15.9Hz,H-1β),4.22(1H,brd,J＝15.9Hz,H-1α),3.95(2H,m,H-12),2.97(1H,brd,J＝18.8Hz,H-5β),2.69(1H,brd,J＝17.5Hz,H-4β),2.65(1H,brd,J＝18.8Hz,H-5α),2.26(1H,brd,J＝17.5Hz,H-4α),2.24(3H,s,H-7'),2.09(1H,m,H-10a),1.96(2H,m,H-11),1.83(1H,m,H-10b),1.44(3H,s,H-9)；
13C NMR(125MHz,CD
3OD)δ198.7(s,C-8),172.0(s,C-8'),166.2(s,C-4'),163.9(s,C-2'),149.2(s,C-4a),144.8(s,C-6'),128.6(s,C-8a),112.5(d,C-5'),105.6(s,C-3),105.3(s,C-1'),101.6(d,C-3'),78.1(d,C-6),75.5(s,C-7),68.9(t,C-12),59.0(t,C-1),38.3(t,C-4),37.5(t,C-10),35.2(t,C-5),24.5(t,C-11),24.3(q,C-7'),23.3(q,C-9)。
EXAMPLE 2 determination of the inhibitory Activity of Azaphilone type Spirocyclic Compounds on α -glucosidase
The inhibitory activity of the Azaphilone spiro compound on α -glucosidase was determined in a 96-well plate using a microplate reader:
dissolving Azaphilone spiro compounds to be detected in phosphate buffer solution (PBS, pH6.8) at three concentrations, adding 20 μ L of 0.01M phosphate buffer solution and 20 μ L of 2.5mM phosphate buffer solution of substrate 4-nitrophenol- α -D glucopyranoside (PNPG) into a 96-well plate in advance, adding 10 μ L of sample solutions with different concentrations, culturing at 37 ℃ for 5min in an enzyme-labeling instrument, adding 10 μ L of 0.2U/mL α -glucosidase solution prepared by 0.01M phosphate buffer solution (pH 6.8) to start reaction, and adding 0.2M Na after reacting for 15min
2CO
3Stopping reaction at 80 μ L, measuring absorbance OD at 405nm, using acarbose as positive control, replacing α -glucosidase with PBS in blank group, and using 20 μ L PBS +20 μ L PNPG +20 μ L α -glucosidase solution as negative control, and obtaining inhibition ratio (%) 1- (OD) according to formula
Test sample-OD
Blank space)/OD
Negative control) X 100%, calculating inhibition rate; repeating three times, calculating average value, and half inhibiting concentration IC
50Values represent the sample concentration at which the inhibition rate is 50%;
experimental result shows that the median inhibitory concentration IC of the Azaphilone spiro compound to α -glucosidase
50A value of 2.65mM, with acarbose (IC)
502.37mM) and can be used for preparing a novel medicament for preventing and treating diabetes.
Example 3: inhibitory Activity of Azaphilone Spirocyclic Compounds against phytopathogenic fungi
Detecting the inhibitory activity of the Azaphilone spiro compound on plant pathogenic fungi by adopting a microdilution method:
(1) pathogenic indicator bacteria include Pyricularia oryzae (Pyricularia oryzae), Alternaria alternata (Alternariaaltnata), Gibberella sautinii (Gibberella sautinii), Anthragma pomorum (Colletotrichum gloeosporioides), Curvularia zeae (Curvularia lunata);
(2) the detection method comprises the following steps: respectively adding 1ml of sterile water into slant culture media of 5 indicator bacteria, shaking to prepare bacterial suspension for a moment, dissolving an Azaphilone spiro compound to be detected in dimethyl sulfoxide to prepare a sample solution with the concentration of 512 mu g/ml, adding the sample solution into a 96-well plate, diluting the sample to the final concentration of 1 mu g/ml by adopting a multiple ratio dilution method, sequentially adding the bacterial suspension into each well, putting the wells into a thermostat, culturing for 48 hours at the temperature of 25 ℃, and observing to take the minimum sample concentration without bacterial growth as the Minimum Inhibitory Concentration (MIC); the negative control that the sample to be tested only contains the indicator bacteria is not added; medium alone is a blank control; carbendazim for positive control;
experimental results show that the Azaphilone spiro-compound has obvious growth inhibition activity on 5 plant pathogenic fungi, has minimum inhibition concentrations of 32 mu g/ml, 8 mu g/ml, 4 mu g/ml, 16 mu g/ml and 16 mu g/ml on pyricularia oryzae, alternaria tabacum, gibberella graminis, colletotrichum gloeosporioides and curvularia zeae, and can be used for preparing novel antifungal agricultural antibiotics.
Claims (9)
- Azaphilone spiro compounds characterized by: the structural formula is shown as a formula (I),
- 2. the process for preparing a spiro Azaphilone compound according to claim 1, characterized in that: modification of phomopsis strain YE3250 by using a chemical epigenetic modifier nicotinamide, and extracting Azaphilone spiro-compound from a fermentation product of the phomopsis strain YE 3250.
- 3. The method for preparing Azaphilone spiro-compound according to claim 2, which comprises the following steps:(1) inoculating Phomopsis sp.YE3250 strain into PDB culture medium, and shake culturing at 28 + -2 deg.C for 3-5 d to obtain fungus seed liquid;(2) dissolving a chemical epigenetic modifier nicotinamide in sterile water, and filtering by a microporous filter membrane to obtain a nicotinamide solution;(3) adding the nicotinamide solution obtained in the step (2) into a PDB fermentation culture medium to obtain a PDB fermentation culture medium containing a chemical epigenetic modifier, inoculating a fungus seed solution into the PDB fermentation culture medium, and performing shake culture at the temperature of 28 +/-2 ℃ for 7-9 days to obtain a fermentation mixture;(4) and (3) filtering the fermentation mixture obtained in the step (3) to obtain fermentation liquor and mycelium, extracting the fermentation liquor by using ethyl acetate to obtain ethyl acetate extract, extracting the mycelium by using ethanol to obtain ethanol extract, combining the ethyl acetate extract and the ethanol extract, concentrating under reduced pressure to obtain a fermentation crude extract, and separating and purifying the fermentation crude extract by using column chromatography to obtain the Azaphilone spiro-compound.
- 4. The process for preparing a spiro compound of Azaphilone type according to claim 3, characterized in that: the PDB culture medium in the step (1) comprises potatoes, glucose and distilled water, wherein the concentration of the potatoes in the PDB culture medium is 0.2-0.4 g/mL, and the concentration of the glucose in the PDB culture medium is 0.02-0.05 g/mL.
- 5. The process for preparing a spiro compound of Azaphilone type according to claim 3, characterized in that: the concentration of nicotinamide in the nicotinamide solution in the step (2) is 400-600 mM.
- 6. The process for preparing a spiro compound of Azaphilone type according to claim 3, characterized in that: the PDB fermentation medium is the same as the PDB medium in the step (1).
- 7. The process for preparing a spiro compound of Azaphilone type according to claim 6, characterized in that: the concentration of nicotinamide in the PDB fermentation medium containing the chemical epigenetic modifier is 200-300 mu M.
- 8. The process for preparing a spiro compound of Azaphilone type according to claim 3, characterized in that: and (4) inoculating the fungus seed liquid in the step (3) in an amount of 5-10%.
- 9. The use of the Azaphilone spiro compound according to claim 1 in the preparation of a medicament for the prevention or treatment of diabetes or an antifungal agricultural antibiotic.
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Cited By (3)
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| CN112961783A (en) * | 2021-02-04 | 2021-06-15 | 云南大学 | Plant endophytic fungus and application thereof in preparation of spironolactone derivative |
| CN113481105A (en) * | 2021-07-22 | 2021-10-08 | 云南大学 | Novel phomopsis fungus strain, preparation method and application |
| CN114774480A (en) * | 2022-03-28 | 2022-07-22 | 江西师范大学 | Method for producing 6-methyl salicylic acid by using endophytic fungi through epigenetic modification |
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Cited By (3)
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|---|---|---|---|---|
| CN112961783A (en) * | 2021-02-04 | 2021-06-15 | 云南大学 | Plant endophytic fungus and application thereof in preparation of spironolactone derivative |
| CN113481105A (en) * | 2021-07-22 | 2021-10-08 | 云南大学 | Novel phomopsis fungus strain, preparation method and application |
| CN114774480A (en) * | 2022-03-28 | 2022-07-22 | 江西师范大学 | Method for producing 6-methyl salicylic acid by using endophytic fungi through epigenetic modification |
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