CN107721908B - Method for extracting chaetomium globosum A precursor compound from chaetomium globosum - Google Patents
Method for extracting chaetomium globosum A precursor compound from chaetomium globosum Download PDFInfo
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Abstract
The invention belongs to the technical field of biology, and particularly relates to a method for extracting a chaetomium globosum A precursor compound from chaetomium globosum. The chaetomium globosum A precursor compound extracted by the invention has high purity (99.5%), simple method, low cost and environmental protection, and provides a basis for promoting the biosynthesis of chaetomium globosum A and the wide development and utilization of the precursor compound in the field of biomedicine.
Description
Technical Field
The invention belongs to the technical field of biology, and particularly relates to a method for extracting a chaetomium globosum A precursor compound from chaetomium globosum.
Background
Chaetomium globosum (Chaetomium globosum) Belongs to the fungi of Ascomycota and Chaetomium. The fungus can produce secondary metabolites with various structures and remarkable biological activity, such as: the compounds such as chaetomium globosum, xanthenone, anthraquinone, chromone, dephenolic cyclic ether, terpenoid and steroid have the anti-tumor, anti-malaria, cytotoxicity, enzyme inhibition activity and antibacterial activity.
Studies have shown that procatooglobinases I, II and III belong to the precursor compounds of chaetomium globosum A (OikawaH, Murakami Y, Ichiaria A. Useful proproach to find the plant biochemical precursors of second microorganisms using P-450 inhibitors: postfollitroproteins intermediates of chaetomium globosin A [ J]Journal of the Chemical Society Perkintransformations, 1992, 1(21): 2949-2953), are relaxin-based compounds in which procoabolobosins I and II have potent cytotoxic activity against P388 mouse leukemia cell lines (IC)50=1.58-4.90 μ g/mL), and (b) for bacillus subtilisBacillus subtilis) Cladosporium resinatum (A. resinifer)Cladosporium resinae) And Trichophyton mentagrophytes (A), (B), (C)Trichophyton mentagrophytes) Also has good antibacterial activity.
The Chinese patent with the publication number of CN102925369B discloses chaetomium globosum with nematicidal activity, a metabolite thereof and application thereof, wherein the metabolite is chaetomium globosum A with nematicidal activity.
Disclosure of Invention
The invention provides a method for extracting a chaetomium globosum A precursor compound from chaetomium globosum, which has the advantages of simple extraction process, low production cost, environmental protection and high efficiency.
In order to achieve the above object, the present invention adopts a technical scheme that a method for extracting chaetomium globosum A precursor compounds from chaetomium globosum comprises chaetoglobosin I, chaetoglobosin II and chaetoglobosin III, and the structural formula is as follows:
characterized in that the method comprises the following steps:
(1) activating strains: inoculating chaetomium globosum to a plate culture medium, and culturing for 3-5 days under the condition of normal temperature to obtain an activated strain;
(2) primary culture: inoculating the activated strain obtained in the step (1) into an SD culture medium, and culturing for 3-5 days at 24-28 ℃ to obtain a seed solution;
(3) secondary culture: inoculating the seed solution prepared in the step (2) into an SD culture medium, adding 8-12 mu M of group protease inhibitor, wherein the volume of the seed solution is 1-5% of that of the SD culture medium, and culturing at 24-28 ℃ for 20-30 days to obtain a fermentation liquid;
(4) preparing a crude extract: carrying out suction filtration on the fermentation liquor obtained in the step (3) to obtain mycelia, drying the mycelia at a constant temperature of 38-42 ℃, and adding ethyl acetate to extract to obtain a crude extract;
(5) silica gel column chromatography: subjecting the crude extract prepared in the step (4) to silica gel column chromatography, detecting by using thin layer chromatography, and combining same fractions for later use;
(6) reversed-phase high-performance liquid phase purification: and (3) purifying the fractions prepared in the step (5) by using a reverse phase high performance liquid chromatography, and concentrating and drying under reduced pressure to obtain procaetologlobosin I, procaetologlobosin II and procaetologlobosin III.
Specifically, the formula of the plate culture medium is as follows: 10.0 g/L of peptone, 10.0 g/L of yeast extract powder, 40.0 g/L of glucose, 20.0 g/L of agar and pH of 6.0 +/-0.1; the formula of the SD culture medium is as follows: peptone 10.0 g/L, glucose 40.0 g/L, pH natural.
Specifically, in the step (3), the histone protease inhibitor is suberoyl dihydroxyhydroxamic acid.
Specifically, the conditions of the reversed-phase high performance liquid chromatography in the step (6) are as follows:
a chromatographic column: YMC 18, 5 μm, 250X 10 mm;
the mobile phase composition is acetonitrile and water which are 70: 30;
flow rate: 2 mL/min;
column temperature: 25 ℃;
detection wavelength: 220, 254 nm;
sample introduction amount: 25 mu L of the solution;
retention time:t R1=37.1 min、t R2=33.2 min、t R3=13.4 min。
the invention has the beneficial effects that:
compared with the prior art, the chaetoglobobosins A precursor compounds, namely the procaetoglobosins I, II and III, are extracted from chaetoglobobosins as raw materials, and are purified by silica gel column chromatography and reverse high performance liquid chromatography to obtain the chaetoglobulins A precursor compound with high purity (99.5%).
Drawings
FIG. 1 shows procaetolobosin I of example 11H-NMR chart;
FIG. 2 shows procaetolobosin I of example 113C-NMR chart;
FIG. 3 is a mass spectrum of procaetolobosin I in example 1;
FIG. 4 shows the results of procaetolobosin II in example 11H-NMR chart;
FIG. 5 shows the results of procaetolobosin II in example 113C-NMR chart;
FIG. 6 is a mass spectrum of procaetolobosin II in example 1;
FIG. 7 shows the results of procaetolobosin III in example 11H-NMR chart;
FIG. 8 shows the results of procaetolobosin III in example 113C-NMR chart;
FIG. 9 is a mass spectrum of procaetolobosin III in example 1.
Detailed Description
The invention will be further illustrated with reference to specific examples, without however restricting the scope of the invention thereto. Suberoyl bishydroxyhydroxamic acid used in the following examples is commercially available and Chaetomium globosum was obtained from North Noro Biotech, Inc. of Shanghai (Chaetomium globosum)Chaetomium globosumATCC 6205）。
Example 1
A method for extracting Chaetomium globosum A precursor compound from Chaetomium globosum; the method comprises the following steps:
(1) activating strains: inoculating Chaetomium globosum to a plate culture medium, and culturing for 3d under the condition of normal temperature to obtain an activated strain;
the formula of the plate culture medium is as follows: 10.0 g/L of peptone, 10.0 g/L of yeast extract powder, 40.0 g/L of glucose, 20.0 g/L of agar and pH of 6.0 +/-0.1;
(2) primary culture: inoculating the activated strain obtained in the step (1) into an SD culture medium, and performing shake cultivation for 3d at 25 ℃ at 120 r/min to obtain a seed solution; the formula of the SD culture medium is as follows: peptone 10.0 g/L, glucose 40.0 g/L, pH natural;
(3) secondary culture: inoculating the seed solution prepared in the step (2) into an SD culture medium, adding 10 mu M of histone inhibitor (suberoyl dihydroxyhydroxamic acid), wherein the volume of the seed solution is 1 percent of that of the SD culture medium, and performing shake culture for 21 d at the temperature of 25 ℃ at 120 r/min to obtain 5L of fermentation liquor;
(4) preparing a crude extract: carrying out suction filtration on the fermentation product prepared in the step (3) to obtain mycelia, drying the mycelia at a constant temperature of 40 ℃, soaking the mycelia in ethyl acetate for 10 h, carrying out ultrasonic treatment for 20 min to obtain a leaching solution, carrying out rotary evaporation on the leaching solution to obtain 5 g of a crude extract, and recovering ethyl acetate;
(5) silica gel column chromatography: mixing the crude extract prepared in the step (4) with silica gel, then loading the mixture into a column, firstly, using a silica gel column with a stationary phase of 80-100 meshes, mixing dichloromethane: gradient elution is carried out with methanol volume ratio of 100:1, 90:1, 80:1, 70:1, 60:1, 50:1, 40:1, 30:1, 20:1 and 10:1, a part of eluent (the volume ratio of dichloromethane to methanol is 20: 1) is taken, silica gel column with a stationary phase of 200-300 meshes is used, and the ratio of dichloromethane: methanol volume ratio =30:1 isocratic elution, detecting by Thin Layer Chromatography (TLC), and combining the same flow parts for later use;
(6) reversed-phase high-performance liquid phase purification: purifying the fractions prepared in the step (5) by using a reverse phase high performance liquid chromatography, wherein the conditions of the reverse phase high performance liquid chromatography are as follows:
a chromatographic column: YMC 18, 5 μm, 250X 10 mm;
the mobile phase composition is acetonitrile and water which are 70: 30;
flow rate: 2 mL/min;
column temperature: 25 ℃;
detection wavelength: 220, 254 nm;
sample introduction amount: 25 mu L of the solution;
retention time:t R1=37.1 min、t R2=33.2 min、t R3=13.4 min；
removing acetonitrile and water from the eluate, concentrating under reduced pressure, and drying to obtain pure products of procaetologlobosin I (9 mg), procaetologlobosin II (9.5 mg) and procaetologlobosin III (7.5 mg), with purity of 99.5%.
The structure of procaetolobosin I extracted by the method of this example was identified as follows:
[ PROPERTIES ] pale yellow crystals
[ IDENTIFICATION ] molecular formula: c32H38N2O2Molecular weight: 482
Instrument materials:1H，13the C NMR spectra were determined by Bruker am-400 MHz NMR spectrometer. TMS is an internal standard; LC-MS was determined by an Aglient model 1260 Infinity-6120 LC MS.
The experimental results are as follows: by using the ESI-MS, the method is characterized in that,1h NMR and13c NMR experiments, standard data as follows: ESI-MSm/z483[M+H]+;1H-NMR (CDCl3, 400 MHz): 5.63 (1H, brs, NH-2), 3.30 (1H, m, H-3),3.09 (1H, m,H-4), 2.48 (1H, m, H-5), 5.37 (1H, brs, H-7), 2.64 (1H, d,J=8.9, H-8), 3.00 (1H, d,J= 14.5Hz, Ha-10), 2.64 (1H, d,J= 9.8, Hz, Hb-10),1.32 (3H, d,J= 5.5 Hz, H-11), 1.74 (3H, s, H-12), 6.11 (1H, m, H-13), 5.12(1H, m, H-14), 2.21 (1H, m, Ha-15), 1.92 (1H, m, Hb-15), 2.44 (1H, m,H-16),4.94 (1H, m, H-17), 2.38-2.44 (1H, m,H-19a), 2.13-2.20 (1H, m,H-19b), 2.38-2.44 (2H, m,H-20), 6.79 (1H, m,H-21), 7.06 (1H, d,J= 16.7 Hz,H-22), 0.92(3H, m, Me-16), 1.51 (3H, s, Me-18), 8.15 (1H, s, NH-1´), 6.98 (1H, s, H-2´),7.52 (1H, m, H-4´), 7.13 (1H, m, H-5´), 7.19 (1H, d,J= 5.0 Hz, H-6´), 7.35(1H, m, H-7´);13C-NMR (CDCl3, 100 MHz): 174.2(C-1), 53.8 (C-3), 50.2 (C-4),36.1 (C-5), 139.7 (C-6), 126.8 (C-7), 47.2 (C-8), 66.1 (C-9), 35.0 (C-10),14.2 (C-11), 20.0 (C-12), 129.5 (C-13), 132.7 (C-14), 41.2 (C-15), 32.4 (C-16), 132.9 (C-17), 130.6 (C-18), 39.0 (C-19), 28.9 (C-20), 146.5 (C-21),128.2 (C-22), 197.5 (C-23), 21.5(16-Me), 16.5 (18-Me), 122.3 (C-2´), 111.3(C-3´), 127.0 (C-3´a), 118.5 (C-4´), 122.6 (C-5´), 119.7 (C-6´), 112.2 (C-7´), 136.5 (C-1´a)。
The structural identification of procaetolobosin II extracted by the method of this example is as follows:
[ PROPERTIES ] pale yellow crystals
[ IDENTIFICATION ] molecular formula: c32H36N2O3Molecular weight: 496
Instrument materials:1H，13the C NMR spectra were determined by Bruker am-400 MHz NMR spectrometer. TMS is an internal standard; LC-MS was determined by an Aglient model 1260 Infinity-6120 LC MS.
The experimental results are as follows: by using the ESI-MS, the method is characterized in that,1h NMR and13c NMR experiments, standard data as follows: ESI-MSm/z497[M+H]+;1H-NMR (CDCl3, 400 MHz): 5.52 (1H, brs, NH-2), 3.29 (1H, m, H-3),3.07 (1H, m,H-4), 2.46-2.55 (1H, m, H-5), 5.29 (1H, brs, H-7), 2.56 (1H, m,H-8), 3.13 (1H, m, Ha-10), 2.58 (1H, m, Hb-10), 1.41 (3H, m, H-11), 1.79 (3H,s, H-12), 5.90 (1H, m, H-13), 5.18 (1H, m, H-14), 2.25 (1H, m, Ha-15), 1.98(1H, m, Hb-15), 2.46-2.55 (1H, m,H-16), 5.37 (1H, m, H-17), 3.70 (1H, m,H-19a), 3.05 (1H, m,H-19b), 6.43 (1H, m,H-21), 8.18 (1H, d,J= 16.5 Hz,H-22),0.94 (3H, m, Me-16), 1.47 (3H, s, Me-18), 8.09 (1H, s, NH-1´), 6.97 (1H, m,H-2´), 7.49 (1H, m, H-4´), 7.13 (1H, m, H-5´), 7.19 (1H, d,J= 6.0 Hz, H-6´), 7.36 (1H, m, H-7´);13C-NMR (CDCl3, 100 MHz): 172.7(C-1), 53.9 (C-3),49.8 (C-4), 34.8 (C-5), 140.8 (C-6), 126.0 (C-7), 46.7 (C-8), 66.0 (C-9),34.6 (C-10), 14.9 (C-11), 20.3 (C-12), 130.8 (C-13), 132.0 (C-14), 41.9(C-15), 32.3 (C-16), 138.0 (C-17), 128.4 (C-18), 53.1 (C-19), 201.5 (C-20),136.8 (C-21), 134.4 (C-22), 198.6 (C-23), 21.1(16-Me), 15.4 (18-Me), 122.5(C-2´), 111.5 (C-3´), 126.9 (C-3´a), 118.5 (C-4´), 122.5 (C-5´), 119.9 (C-6´), 111.9 (C-7´), 136.5 (C-1´a)。
The structure of procaetolobosin iii extracted by the method of this example was identified as follows:
[ PROPERTIES ] pale yellow crystals
[ IDENTIFICATION ] molecular formula: c32H36N2O4Molecular weight: 512
Instrument materials:1H，13the C NMR spectra were determined by Bruker am-400 MHz NMR spectrometer. TMS is an internal standard; LC-MS by Aglient 1And (3) determination by a 260 Infinity-6120 liquid phase mass spectrometer.
The experimental results are as follows: by using the ESI-MS, the method is characterized in that,1h NMR and13c NMR experiments, standard data as follows: ESI-MSm/z513[M+H]+;1H-NMR (CD3OD, 400 MHz): 6.12 (1H, brs, NH-2), 3.86 (1H, m, H-3),2.89 (1H, m,H-4), 1.70 (1H, m, H-5), 2.76 (1H, d,J= 5.4 Hz, H-7), 1.95 (1H,m, H-8), 2.87 (1H, m, Ha-10), 2.80 (1H, m, Hb-10), 1.41 (3H, d,J= 7.28 Hz,H-11), 1.26 (3H, s, H-12), 5.90 (1H, m, H-13), 5.15 (1H, m, H-14), 2.25 (1H,m, Ha-15), 2.06 (1H, m, Hb-15), 2.41-2.48(1H, m,H-16), 5.20 (1H, m, H-17),3.51 (1H, m,H-19a), 2.88 (1H, m,H-19b), 6.03 (1H, m,H-21), 7.35 (1H, d,J=16.4 Hz,H-22), 0.94 (3H, m, Me-16), 1.47 (3H, s, Me-18), 6.94 (1H, m, H-2´),7.47 (1H, m, H-4´), 7.00 (1H, m, H-5´), 7.00 (1H, m, H-6´), 7.25 (1H, m, H-7´);13C-NMR (CD3OD, 100 MHz): 175.6 (C-1), 53.8 (C-3), 47.9 (C-4), 37.7 (C-5), 59.4 (C-6),63.8 (C-7), 50.2 (C-8), 63.8 (C-9), 33.8 (C-10), 13.2 (C-11),19.8 (C-12), 129.6 (C-13), 134.6 (C-14), 43.0 (C-15), 33.5 (C-16), 139.3 (C-17), 129.7 (C-18), 54.3 (C-19), 202.7 (C-20), 138.1 (C-21), 135.6 (C-22),199.3 (C-23), 21.5 (16-Me), 16.1 (18-Me), 120.1 (C-2´), 109.9 (C-3´), 129.0(C-3´a), 120.1 (C-4´), 125.6 (C-5´), 119.5 (C-6´), 112.6 (C-7´), 136.5 (C-1´a)。
As can be seen from FIGS. 1-9, the channels1H NMR、13C NMR analysis, alignment literature (Oikawa H, Murakami Y, Ichiahara A. Useful aproach to find the platinum biosyntheses primers of secondary polyamides using P-450 inhibitors: structured intermediates of molecular oligonucleotides A [ J]Journal of the Chemical Society Perkin Transactions,1992, 1(21): 2949-.
Example 2
The method of this example differs from example 1 in that: the culture temperature in the step (2) is 24 ℃; the dosage of the suberoyl dihydroxyhydroxamic acid for secondary culture in the step (3) is 8 mu M, the culture temperature is 24 ℃, and the culture time is 20 d; the mycelium drying temperature for the crude extract preparation in the step (4) is 38 ℃.
Example 3
The method of this example differs from example 1 in that: the activation culture time of the strains in the step (1) is 4 d; the rotation speed of shaking table culture in the step (2) is 135 r/min, and the culture time is 4 d; in the step (3), the adding proportion of the seed liquid is 3%, the rotating speed of shaking table culture is 135 r/min, and the culture time is 25 d; soaking the crude extract in the step (4) for 12 h, and carrying out ultrasonic treatment for 30 min.
Example 4
The method of this example differs from example 1 in that: the activation culture time of the strains in the step (1) is 5 d; the rotation speed of shaking table culture in the step (2) is 150 r/min, the temperature is 27 ℃, and the culture time is 5 d; in the step (3), the dosage of the suberoyl dihydroxyhydroxamic acid for secondary culture is 12 mu M, the adding proportion of the seed liquid is 5 percent, the shaking table culture rotating speed is 150 r/min, the culture temperature is 27 ℃, and the culture time is 30 d; and (4) when the crude extract is prepared in the step (4), the drying temperature of the mycelium is 42 ℃, the soaking time is 14 h, and the ultrasonic treatment is 40 min.
The methods of examples 2 to 4 described above have the same extraction effect as the method of example 1.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited by the above examples, and any other modifications without departing from the scope of the present invention should be replaced by equivalents, and all such modifications are included in the scope of the present invention.
Claims (5)
1. A method for extracting chaetomium globosum A precursor compound from chaetomium globosum, the chaetomium globosum A precursor compound is selected from procaetoyosin I, procaetoyosin II and procaetoyosin III, and the structural formula is as follows:
characterized in that the method comprises the following steps:
(1) activating strains: inoculating chaetomium globosum to a plate culture medium, and culturing for 3-5 days under the condition of normal temperature to obtain an activated strain;
(2) primary culture: inoculating the activated strain obtained in the step (1) into an SD culture medium, and culturing for 3-5 days at 24-28 ℃ to obtain a seed solution;
(3) secondary culture: inoculating the seed solution prepared in the step (2) into an SD culture medium, adding 8-12 mu M of group protease inhibitor, wherein the volume of the seed solution is 1-5% of that of the SD culture medium, and culturing at 24-28 ℃ for 20-30 days to obtain a fermentation liquid;
(4) preparing a crude extract: carrying out suction filtration on the fermentation liquor obtained in the step (3) to obtain mycelia, drying the mycelia at a constant temperature of 38-42 ℃, and adding ethyl acetate to extract to obtain a crude extract;
(5) silica gel column chromatography: subjecting the crude extract prepared in the step (4) to silica gel column chromatography, detecting by using thin layer chromatography, and combining same fractions for later use;
(6) reversed-phase high-performance liquid phase purification: purifying the fractions prepared in the step (5) by using a reverse phase high performance liquid chromatography, and concentrating and drying under reduced pressure to obtain procaetoglobosin I, procaetoglobosin II and procaetoglobosin III;
the histone protease inhibitor in the step (3) is suberoyl dihydroxyhydroxamic acid;
the conditions of the reversed-phase high performance liquid chromatography in the step (6) are as follows:
a chromatographic column: YMC 18, 5 μm, 250X 10 mm;
the mobile phase composition is acetonitrile and water which are 70: 30;
flow rate: 2 mL/min;
column temperature: 25 ℃;
detection wavelength: 220, 254 nm;
sample introduction amount: 25 mu L of the solution;
retention time:t R1=37.1 min、t R2=33.2 min、t R3=13.4 min。
2. the method for extracting Chaetomium globosum A precursor compound from Chaetomium globosum according to claim 1, wherein Chaetomium globosum ATCC 6205 is adopted as the strain in step (1).
3. The method of claim 1, wherein the formulation of the plating medium is: 10.0 g/L of peptone, 10.0 g/L of yeast extract powder, 40.0 g/L of glucose, 20.0 g/L of agar and pH of 6.0 +/-0.1; the formula of the SD culture medium is as follows: peptone 10.0 g/L, glucose 40.0 g/L, pH natural.
4. The method of extracting a chaetomium globosum A precursor compound from chaetomium globosum according to claim 1,
the mycelium leaching step in the step (4) is as follows: drying the mycelium at constant temperature of 40 deg.C, soaking in ethyl acetate for 10 hr, ultrasonic treating for 20 min to obtain leaching solution, and rotary steaming to obtain crude extract.
5. The method for extracting a chaetomium globosum A precursor compound from chaetomium globosum according to claim 1, wherein the silica gel column chromatography in the step (5) comprises the following steps: mixing the crude extract prepared in the step (4) with silica gel, then loading the mixture into a column, firstly, using a silica gel column with a stationary phase of 80-100 meshes, mixing dichloromethane: gradient elution is carried out with methanol volume ratio of 100:1, 90:1, 80:1, 70:1, 60:1, 50:1, 40:1, 30:1, 20:1 and 10:1, eluent with dichloromethane to methanol volume ratio of 20:1 is taken and then silica gel column with a stationary phase of 200-300 meshes is used, and the ratio of dichloromethane to methanol is determined by the following steps: methanol volume ratio =30:1 isocratic elution, detecting by thin layer chromatography, and combining same flow parts for standby.
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