CN114369078B - Method for extracting chromone and naphthol compounds from fungi of photoodontobromium - Google Patents
Method for extracting chromone and naphthol compounds from fungi of photoodontobromium Download PDFInfo
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Abstract
The invention belongs to the technical field of biology, and particularly relates to a method for extracting chromone and naphthol compounds from Verticillium tabacum, which comprises the steps of strain activation and culture, crude extract acquisition, silica gel column chromatography and gel column chromatography, wherein the obtained compounds are identified as (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one, 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one, (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -one and the like through nuclear magnetic detection and literature comparison. The method is beneficial to conveniently and quickly obtaining a large amount of the compounds, provides a new obtaining way for the compounds, and is beneficial to development and utilization of fungal resources; the method has the advantages of simplicity, convenience, rapidness, environmental protection, high yield and purity, recyclable solvent and the like, and is suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of fungus fermentation and extraction, and particularly relates to a method for extracting chromone and naphthol compounds (such as (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one, 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one, (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -one and the like) from photorhabdus fungi.
Background
Bacteria of Tachypodium Chaetoceros (C.), (Daldinia eschscholtzii) Belongs to the fungus of Ascomycota. The fungus can produce various compounds such as naphthol, chromone, alkaloid, flavonoid, and terpenoid, and has pharmacological activities of resisting tumor, resisting inflammation, inhibiting bacteria, lowering blood sugar, and resisting HPV virus.
The natural compound (2R) 5-hydroxy-8-methoxyl-2-methyl-4H-1-benzopyran-4-ketone and 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-ketone related by the invention are extracted and separated from the fungi of the genus Photostonia of the ascomycetaceae for the first time, and belong to chromone compounds. At present, the compounds are mostly synthesized manually, and have the defects of complicated synthesis steps, easy generation of toxic and harmful wastes in the synthesis process and the like. The chromone compound has the activities of inhibiting alpha-glucosaccharase and resisting inflammation and has wide application prospect, the (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -ketone related by the invention is one of naphthol compounds, and the naphthol compound is reported to have the biological activities of reducing blood sugar, inhibiting bacteria, resisting inflammation, enhancing immunity and the like according to documents. Research shows that (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -ketone has pharmacological effects of resisting cell proliferation, resisting inflammation, resisting oxidation, reducing blood sugar, resisting tumor, etc.
However, there have been no reports on the isolation of chromones and naphthols such as (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one, 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one, (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -one by fermentation from a fungus belonging to the genus Photochezia.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a method for extracting chromone and naphthol compounds from actinoverticillium fungi. The extraction process is simple, the solvent can be recycled, the extraction rate is high, and the method is suitable for industrial production.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for extracting chromone and naphthol compounds from actinoverticillium fungi comprises the following steps:
1) And (3) fungus culture: inoculating fungus on rice culture medium, and culturing at room temperature for 30 + -2 days;
2) Preparing a crude extract: soaking and extracting the product obtained in the step 1) in methanol at room temperature, and concentrating under reduced pressure to recover the solvent to obtain a crude extract;
3) Preparing an ethyl acetate part extract: dissolving the crude extract in water, extracting with ethyl acetate (preferably for 3 times), and concentrating under reduced pressure to recover solvent to obtain ethyl acetate extract;
4) Silica gel column chromatography: after dissolving the extract at the ethyl acetate part, mixing the extract with a silica gel column, performing gradient elution by using petroleum ether-ethyl acetate with the volume concentration of 0%,10%,20%,30%,40%,50%,60%,70% and 80% in sequence, and respectively collecting a 10% petroleum ether-ethyl acetate elution part and a 20% petroleum ether-ethyl acetate elution part;
5) And mixing the 10% petroleum ether-ethyl acetate eluted part with silica gel, and then performing column packing, wherein the volume ratio of the mixture is 20: 1. 14: eluting with petroleum ether-ethyl acetate of 1, detecting by thin-layer chromatography, combining the same components, and recovering solvent under reduced pressure to obtain crude (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one 1 and crude (2R) 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one 2;
6) And mixing the 20% petroleum ether-ethyl acetate eluted part with silica gel, and then performing column packing, wherein the volume ratio of the mixture is 4.5: eluting with petroleum ether-ethyl acetate of 1, detecting by thin layer chromatography, mixing to obtain 3 components, and sequentially labeling the components as 1-3 according to polarity from small to large; the component 1 is (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -ketone crude product.
Specifically, in the step 1), the rice culture medium is prepared by mixing 80g of rice and 50-80ml of saline water with the mass concentration of 0.3%.
Specifically, in the step 2), the product obtained in the step 1) is soaked and extracted in methanol at room temperature for 2-4 times, and each time lasts for 2-4 days; preferably, the soaking and extraction are performed 3 times, each for 3 days. The volume concentration of the methanol used is 95-98%.
In the step 5), the 10% petroleum ether-ethyl acetate elution part is preferably prepared by using 300-400 mesh silica gel according to the weight ratio of 1: mixing samples from 29 to 31, and filling into a column.
Further, in the step 5), the crude product 1 of (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-ketone is purified by a Sephadex LH-20 gel chromatographic column, and the volume ratio of the purified product is 1:1, eluting by dichloromethane-methanol, detecting by thin-layer chromatography, combining the same components, and decompressing and recovering the solvent; then, after the sample is mixed by silica gel, the mixture is packed, and the volume ratio is 15: eluting with petroleum ether-ethyl acetate of 1, detecting by thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain pure (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one.
Further, in the step 5), 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-ketone crude product 2 is purified by a Sephadex LH-20 gel chromatographic column, and the volume ratio is 1:1, eluting with dichloromethane-methanol, detecting by thin-layer chromatography, combining the same components, and recovering the solvent under reduced pressure; then, after the sample is mixed by silica gel, the mixture is packed, and the volume ratio of the mixture is 12: eluting with petroleum ether-ethyl acetate of 1, detecting by thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one pure product.
Further, in the step 6), the crude product of (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -ketone is subjected to Sephadex LH-20 gel column chromatography, and the volume ratio of the crude product to the crude product is 1:1, eluting with methanol-dichloromethane, detecting by thin-layer chromatography, combining the same components, and recovering the solvent under reduced pressure; then performing silica gel column chromatography, eluting with dichloromethane-methanol with a volume ratio of 20; thus obtaining the pure product of (4S) 4,5-dyhydroxyl-3,4-dihydro-1 (2H) -ketone.
Further, in the step 1), the fungus is activated and primarily cultured in advance; the activation is specifically as follows: bacteria of Verticillium tabacum (C.), (Daldinia eschscholtzii) Inoculating to PDA culture medium, and culturing at room temperature for 3-5 days to obtain activated strain; the PDA culture medium used consists of: 3.0g/L of potato extract powder, 20.0g/L of glucose, 14.0g/L of agar and 5.6 +/-0.2 of pH value;
the primary culture is specifically as follows: inoculating the activated strain to a PDB culture medium, and performing shake culture at 25 to 30 ℃ for 4 to 6 days to obtain a seed solution; the PDB medium used consisted of: 5g/L of potato extract powder, 10g/L of peptone, 15g/L of glucose, 5g/L of sodium chloride and pH value of 5.6 +/-0.2.
In the invention, the chromone compound (2R) 5-Hydroxy-8-methoxyl-2-methyl-4H-1-benzopyran-4-ketone obtained by extraction and separation has the chemical name of (2R) 5-Hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one and the molecular formula: c 11 H 12 O 4 (ii) a Compound 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one, chemical name: 5,8-dihydroxy-2-methyl-4H-chromen-4-one;
the molecular formula is as follows: c 10 H 8 O 4 (ii) a The structural formulas are respectively as follows:
in the invention, the compound is (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -ketone, and the structural formula is shown as follows:
compared with the prior art, the invention has the following beneficial effects:
1) So far, the invention extracts chromone and naphthol compounds such as (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one, 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one, (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -one and the like from the fermentation product of the fungi of the phototympanophyta for the first time, thereby being beneficial to conveniently and quickly obtaining a large amount of the compounds, providing a new obtaining way for the compounds and being beneficial to the development and utilization of fungal resources;
2) The extraction process has the advantages of simplicity, convenience, rapidness, environmental protection, higher yield and purity, recyclable solvent and the like, and is suitable for industrial production;
3) The chromone and naphthol compounds have wide biological activity and rich raw material sources; the extraction method of the invention is convenient for deep research on the extract and provides a foundation for promoting the wide development of the extract in the pharmaceutical industry.
Drawings
FIG. 1 is a scheme showing that compound (2R) is 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one 1 H NMR Spectroscopy (400 MHZ, CDCL) 3 )；
FIG. 2 is a diagram of the synthesis of the compound (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one 13 C NMR Spectroscopy (400 MHZ, CDCL) 3 )；
FIG. 3 is a drawing of the compound 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one 1 H NMR Spectrum (400 MHZ, CDCL) 3 )；
FIG. 4 is a schematic representation of the compound (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -one 1 H NMR Spectroscopy (500 MHZ, CDCL) 3 )。
Detailed Description
In order to make the technical purpose, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention are further described with reference to specific examples, which are intended to explain the present invention and are not to be construed as limiting the present invention, and those who do not specify a specific technique or condition in the examples follow the techniques or conditions described in the literature in the art or follow the product specification.
In the present invention, room temperature means 25. + -. 5 ℃. Fungi of the genus Photobacterium (C.), (Daldinia eschscholtzii) The photofrin fungi used in the examples were purchased from Ningbo Ming boat Biotech, inc., product number BCRC34046, a common commercial product. The rice is northeast rice. The concentrations of the petroleum ether, the methanol and the ethyl acetate are volume concentrations unless otherwise specified.
In the examples, the purchased fungi of the genus Photostonia were previously subjected to activation and primary culture; the activation is specifically as follows: bringing Verticillium tabacum (C.) (Daldinia eschscholtzii) Inoculating to PDA culture medium, and culturing at room temperature for 4 days to obtain activated strain; the PDA culture medium used consists of: 3.0g/L of potato extract powder, 20.0g/L of glucose, 14.0g/L of agar and 5.6 +/-0.2 of pH value;
the primary culture is specifically as follows: inoculating the activated strain to PDB culture medium, and culturing at 28 deg.C in shaking table (140 r/min) for 5 days to obtain about 4L fungus seed solution; the PDB (potato dextrose broth) medium used consisted of: 5g/L of potato extract powder, 10g/L of peptone, 15g/L of glucose, 5g/L of sodium chloride and 5.6 +/-0.2 of pH value.
Example 1
A method for extracting chromone and naphthol compounds from fungi of the genus Photocolatopsis comprises the following steps:
1) And (3) fungus culture: inoculating about 5ml of fungus seed liquid into 800 × 1000 Erlenmeyer flask containing rice culture medium, and culturing at room temperature for 30 days; the rice culture medium is formed by mixing 80g of rice and 70ml of saline water with the mass concentration of 0.3%;
2) Preparing a crude extract: soaking and extracting the product obtained in the step 1) in methanol at room temperature for 3 times (the addition amount of the methanol is 25L in each leaching process), combining leaching solutions for 3 days each time, and concentrating under reduced pressure to recover the solvent to obtain about 246.6g of crude extract; the volume concentration of the methanol used was 97%;
3) Preparing an ethyl acetate part extract: dissolving the crude extract in water, extracting with ethyl acetate for 3 times (the addition of ethyl acetate is 3L), and concentrating under reduced pressure to recover solvent to obtain ethyl acetate extract (about 64.6 g);
4) Silica gel column chromatography: dissolving the extract at the ethyl acetate part, stirring the sample by using a silica gel column (stirring the sample by using 200-400-mesh silica gel according to a weight ratio of 1 to 30, and then carrying out column packing), carrying out gradient elution by using petroleum ether-ethyl acetate with volume concentration of 0%,10%,20%,30%,40%,50%,60%,70% and 80%, and respectively collecting a 10% petroleum ether-ethyl acetate elution part and a 20% petroleum ether-ethyl acetate elution part;
5) And (3) mixing the 10% petroleum ether-ethyl acetate elution part with silica gel, and then filling the mixture into a column (300-400-mesh silica gel, wherein the weight ratio of the silica gel to the silica gel is 1: column packing after 30 samples are mixed), and respectively mixing the samples by using a volume ratio of 20: 1. 14: eluting with petroleum ether-ethyl acetate of 1, detecting by thin-layer chromatography, combining the same components, and recovering solvent under reduced pressure to obtain crude (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one 1 and crude (2R) 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one 2;
and (2R) purifying the crude product 1 of the 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-ketone by a Sephadex LH-20 gel chromatographic column by using a solvent with a volume ratio of 1:1, eluting with dichloromethane-methanol, detecting by thin-layer chromatography, combining the same components, and recovering the solvent under reduced pressure; then, after the sample is mixed by silica gel, the mixture is packed, and the volume ratio is 15: eluting with petroleum ether-ethyl acetate of 1, detecting by thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain pure product 1 of (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one;
5363 and purifying the 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-ketone crude product 2 by Sephadex LH-20 gel chromatographic column, and purifying by using a solvent with a volume ratio of 1:1, eluting by dichloromethane-methanol, detecting by thin-layer chromatography, combining the same components, and decompressing and recovering the solvent; then, after the sample is mixed by silica gel, the mixture is packed, and the volume ratio of the mixture is 12: eluting with petroleum ether-ethyl acetate, detecting with thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain 5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one pure product 2;
6) And (3) mixing the 20% petroleum ether-ethyl acetate elution part with silica gel, and then filling the mixture into a column (300-400-mesh silica gel, wherein the weight ratio of the silica gel to the silica gel is 1: column packing after 30 samples are mixed), and mixing the mixture by using a volume ratio of 4.5: eluting with petroleum ether-ethyl acetate of 1, detecting by thin layer chromatography, mixing to obtain 3 components, and sequentially labeling the components as 1-3 according to polarity from small to large; the component 1 is (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -ketone crude product. (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -ketone crude product is subjected to Sephadex LH-20 gel column chromatography, and the volume ratio is 1:1, eluting with methanol-dichloromethane, detecting by thin-layer chromatography, combining the same components, and recovering the solvent under reduced pressure; then performing silica gel column chromatography, eluting with dichloromethane-methanol with a volume ratio of 20; thus obtaining the pure product of (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -ketone.
The purified product of (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one prepared in the above way: the character is yellow solid, the yield is 0.0015%, and the purity is 99.1%;5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-ketone pure product is orange yellow solid, the yield is 0.0012%, and the purity is 98.8%. The structure was identified using a variety of spectroscopic techniques, as follows:
instrument materials: ultraviolet measurement is carried out on a UV-210A ultraviolet spectrum determinator; 1 H， 13 the C NMR spectra were determined by Bruker am-400 MHz NMR spectrometer. TMS is an internal standard. The maps are shown in figures 1-3, and the experimental results are as follows:
pure product 1: (2R) 5-hydroxy-8-methoxy-2-methyl-4H-1-benzopyran-4-one:
1 H NMR (CDCl 3 , 400 MHz)δ: 12.06 (1H, s, OH-5), 7.33 (1H, d, J = 9.0 Hz, H-7), 6.67 (1H, d, J = 8.8 Hz, H-6), 6.23 (1H, s, H-3), 3.91 (3H, s, OCH 3 -8), 2.46 (3H, s, CH 3 -2); 13 C-NMR (CDCl 3 , 400 MHz) δ: 198.6 (C-1), 44.0(C-2), 74.6(C-3), 155.47 (C-4a), 107.7(C-4b),150.9(C-5), 122.9 (C-6), 108.6(C-7),155.5 (C-8),21.0(C-9), 57.5 (C-10),
pure product 2:5,8-hydroxy-2 methyl-4H-1-benzopyran ring-4-one:
1 H NMR (CDCl 3 , 400 MHz)δ: 6.70(1H,d, J =8.86 Hz,H-2), 7.17 (1H, d, J = 8.86Hz, H-6), 6.83(1H,s, H-7), 2.39 (3H, s, H-3)。
pure (4S) 4,5-dihydroxy-3,4-dihydro-1 (2H) -one prepared as described above: the product was yellow amorphous powder, and the yield and purity were 0.0005% and 98.9%, respectively. And (3) identification: the molecular formula is as follows: c 10 H 10 O 3 Molecular weight: 178.18, which is red in color by TLC vanillin, and has fluorescence at 254 nm; instrument materials: 1 the H spectra were determined by Bruker am-500 MHz NMR (see FIG. 4). TMS is an internal standard;
1 H-NMR (CDCl3, 500 MHz) d: 2.21 (1H, m, H-3), 2.52 (1H, m, H-3), 2.58 (1H, ddd, J17.5, 13.6, 4.6 Hz, H-2), 2.83 (1H, dt, J17.5, 4.6 Hz, H-2), 5.35 (1H, dd, J10.0, 4.8 Hz, H-4), 7.11 (1H, brd, J7.9 Hz, H-6), 7.31 (1H, t, J7.9 Hz, H-7), 7.60 (1H, br d, J7.9 Hz, H-8)。
Claims (6)
1. a method for extracting chromone and naphthol compounds from fungi of the genus Photocolatorium is characterized by comprising the following steps:
1) And (3) fungus culture: inoculating photo-carbon bacteria on rice culture medium, and culturing at room temperature for 30 + -2 days;
2) Preparing a crude extract: soaking and extracting the product obtained in the step 1) in methanol at room temperature, and concentrating under reduced pressure to obtain a crude extract;
3) Preparing an ethyl acetate part extract: dissolving the crude extract in water, extracting with ethyl acetate, and concentrating under reduced pressure to obtain ethyl acetate extract;
4) Silica gel column chromatography: mixing the ethyl acetate part extract with silica gel column, performing gradient elution with petroleum ether-ethyl acetate with volume concentration of 0%,10%,20%,30%,40%,50%,60%,70%,80%, respectively, and collecting 10% petroleum ether-ethyl acetate eluate and 20% petroleum ether-ethyl acetate eluate;
5) And mixing the 10% petroleum ether-ethyl acetate elution part with silica gel, and then performing column packing, wherein the volume ratio of the mixture is 20: 1. 14: eluting with petroleum ether-ethyl acetate of 1, detecting by thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain 5,8-dihydroxy-2 methyl-4H-1-benzopyran ring-4-ketone crude product 2;
6) The 20% petroleum ether-ethyl acetate eluted part is mixed with silica gel and loaded on a column, and the mixture is subjected to column packing by using a volume ratio of 4.5: eluting with petroleum ether-ethyl acetate of 1, detecting by thin layer chromatography, mixing to obtain 3 components, and sequentially labeling the components as 1-3 according to polarity from small to large; the component 1 is a crude product of (4S) -4,5-dihydroxy-3,4-dihydro-1 (2H) -naphthalenone;
5,8-dihydroxy-2 methyl-4H-1-benzopyran ring-4-one, (4S) -4,5-dihydroxy-3,4-dihydro-1 (2H) -naphthalenone have the following structural formulas, respectively:
2. the method for extracting chromone and naphthol compounds from alternaria photorhabdus fungus according to claim 1, wherein in step 1), the rice culture medium is composed of 80g of rice mixed with 50-80ml of 0.3% by mass saline water.
3. The method for extracting chromone and naphthol compounds from actinoverticillium fungi of claim 1, wherein in step 2), the product obtained in step 1) is soaked in methanol at room temperature for 2-4 times each for 2-4 days.
4. The method for extracting chromone and naphthol compounds from the actinoverticillium fungi as claimed in claim 1, wherein in the step 5), 5,8-dihydroxy-2 methyl-4H-1-benzopyran ring-4-one crude product 2 is purified by Sephadex LH-20 gel chromatography column, and the volume ratio is 1:1, eluting with dichloromethane-methanol, detecting by thin-layer chromatography, combining the same components, and recovering the solvent under reduced pressure; and then, after sample mixing by silica gel, loading the mixture into a column, and mixing the mixture by using a volume ratio of 12: eluting with petroleum ether-ethyl acetate of 1, detecting by thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain 5,8-dihydroxy-2 methyl-4H-1-benzopyran ring-4-one pure product.
5. The method for extracting chromone and naphthol compounds from the alternaria photorhabdus fungus as claimed in claim 1, wherein in the step 6), the crude product of (4S) -4,5-dihydroxy-3,4-dihydro-1 (2H) -naphthalenone is subjected to Sephadex LH-20 gel column chromatography, and the volume ratio is 1:1, eluting with methanol-dichloromethane, detecting by thin-layer chromatography, mixing the same components, and recovering the solvent under reduced pressure; then performing silica gel column chromatography, eluting with dichloromethane-methanol with a volume ratio of 20; thus obtaining the pure product of (4S) -4,5-dihydroxy-3,4-dihydro-1 (2H) -naphthalenone.
6. The method for extracting chromone and naphthol compounds from a fungus belonging to the genus Photorotaria as claimed in claim 2, wherein in the step 1), the fungus is previously subjected to activation and primary culture;
the activation is specifically as follows: inoculating the photo-carbon bacteria to a PDA culture medium, and culturing at room temperature for 3-5 days to obtain activated strains;
the primary culture is specifically as follows: inoculating the activated strain to a PDB culture medium, and performing shake culture at 25-30 ℃ for 4-6 days to obtain a seed solution.
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| CA2999782A1 (en) * | 2015-09-24 | 2017-03-30 | Agriculture Victoria Services Pty Ltd | Bioactive fungi |
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| BE643305A (en) * | 1963-07-17 | 1964-05-29 | ||
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