CN114517214A - Method for improving yield of endophytic fungi fermentation product 4-hydroxyphenylethanol through epigenetic transformation - Google Patents

Method for improving yield of endophytic fungi fermentation product 4-hydroxyphenylethanol through epigenetic transformation Download PDF

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CN114517214A
CN114517214A CN202210157876.1A CN202210157876A CN114517214A CN 114517214 A CN114517214 A CN 114517214A CN 202210157876 A CN202210157876 A CN 202210157876A CN 114517214 A CN114517214 A CN 114517214A
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hydroxyphenylethanol
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谢光园
李香妹
曾慧婷
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Hunan Environment Biological Polytechnic
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Abstract

The invention relates to the field of biological fermentation, in particular to a method for improving the yield of an endophytic fungi fermentation product 4-hydroxyphenylethanol through epigenetic modification.

Description

Method for improving yield of endophytic fungi fermentation product 4-hydroxyphenylethanol through epigenetic transformation
Technical Field
The invention relates to the field of biological fermentation, in particular to a method for improving the yield of an endophytic fungi fermentation product 4-hydroxyphenylethanol through epigenetic modification.
Background
4-hydroxybenzene ethanol is an alcohol derivative, is an important medical intermediate raw material, and can be used for synthesizing drug molecules such as beta-paclitaxel, metoprolol, salidroside, maltol and the like. Has good biological activity, and can be widely used in the fields of medicine, perfume, cosmetics, etc.
The 4-hydroxyphenylethanol is obtained mainly by chemical synthesis. 4-hydroxyphenylethanol can be synthesized from various raw materials at present. For example: (1) the method comprises the following steps of (1) taking phenylethylamine as a raw material, performing diazotization reaction to obtain p-nitroacetophenone, performing reduction reaction to obtain p-aminophenylethanol, and performing diazotization and hydrolysis reaction once to obtain a target product; (2) using p-hydroxyacetophenone as a raw material, firstly using nitrite to oxidize to obtain an acetal derivative, then hydrolyzing to obtain (p-hydroxyphenyl) glyoxal, and reducing the acetal derivative to obtain a target product; (3) p-hydroxyphenylacetic acid is taken as a raw material, and is directly reduced by using lithium aluminum hydride to obtain a target product; (4) the method comprises the steps of taking phenethyl alcohol as a raw material, firstly carrying out esterification reaction and nitration reaction to obtain 4-nitro phenethyl alcohol ester, then carrying out hydrolysis reaction and catalytic hydrogenation reaction to generate aminophenyl alcohol, and carrying out diazotization and hydrolysis reaction once to obtain a target product. Despite the many synthetic routes, there are many problems to varying degrees: expensive reaction raw materials, long reaction steps, difficult separation of byproducts, low yield and environment-friendliness.
Although 4-hydroxyphenylethanol is separated from a plurality of plants, the growth of the plants is greatly influenced by time, space and climate, and the target product is separated from the plants, so the cost is high and the efficiency is low. Endophytes grow rapidly and are amenable to large scale culture, and plant endophytes have evolved into cell factories for drug molecules. Zhang Yong in 2012 reported 5.1mg of 4-hydroxyphenylethanol isolated from 43g of the metabolite of actinomycetes YIM65408, and Lima huangyu et al in 2017 reported 16mg of 4-hydroxyphenylethanol isolated from 125g of the metabolite of Aspergillus petraki. The invention utilizes the epigenetic modifier sodium pyruvate to change the metabolic pathway of the microorganism, and is expected to obtain some new findings.
Disclosure of Invention
The invention aims to solve the defects in the background art and provides a method for improving the yield of an endophytic fungi fermentation product, namely 4-hydroxyphenylethanol through epigenetic modification.
In order to achieve the above purposes, the technical scheme adopted by the invention is as follows: a method for improving the yield of 4-hydroxyphenylethanol of an endophytic fungus fermentation product by epigenetic modification comprises the following operation steps:
s1, preparing seed liquid: adding the activated strain into PDB culture medium containing sodium pyruvate, and culturing for 2-7 days to obtain seed liquid;
s2, large-scale fermentation: inoculating the seed solution into a PDB culture medium containing sodium pyruvate according to a certain proportion, and culturing for 7-10 days at the temperature of 25-30 ℃ and the speed of 120-180 rpm/min;
s3, extracting and separating; extracting the fermentation liquor with ethyl acetate for 3 times, combining ethyl acetate extract, spin-drying, and separating with silica gel column to obtain the target product.
Preferably, the strain of step S1 is arthrium arundinis.
Preferably, the culture condition in step S1 is 25-30 ℃ and the rotation speed is 120-180 rpm/min.
Preferably, the epigenetic modifier used in the PDB medium in step S1 is sodium pyruvate, the content of the sodium pyruvate is 50-500. mu.M, and the pH value of the medium is 5-8.
Preferably, the inoculation ratio in step S2: 5 to 15 percent.
Preferably, the culture conditions in step S2 are 28 ℃, 170rpm/min, and the culture is performed for 7 days.
Preferably, the extraction solvent in step S3 is ethyl acetate, and the target product is obtained by separation and purification with silica gel column.
Compared with the prior art, the invention has the following beneficial effects:
(1) compared with the common endophytic fungus fermentation product, the yield of the 4-hydroxyphenylethanol is greatly improved, reaches up to 122mg/L, the operation is simple, and the industrial large-scale production can be carried out.
(2) The invention uses sodium pyruvate as the epigenetic modifier, the raw materials are easy to obtain, and the economic cost is low.
(3) The separation and purification process is simple to operate, and the production cost can be effectively reduced.
Drawings
FIG. 1 is a 1HNMR spectrum of a fermentation product 4-hydroxyphenylethanol according to example 1 of the present invention;
FIG. 2 is a 13CNMR spectrum of the fermentation product 4-hydroxyphenylethanol of example 1 according to the invention.
Detailed Description
The following description is presented to disclose the invention so as to enable any person skilled in the art to practice the invention. The preferred embodiments in the following description are given by way of example only, and other obvious variations will occur to those skilled in the art.
Example 1
Preparing a culture medium: 35g of PDB culture medium dry powder, 200 mu M of sodium pyruvate and 1L of distilled water, adjusting the pH value to 6.5, and carrying out autoclaving at 121 ℃ for 20 min.
Preparing a seed solution: adding 100mL of culture medium into a 500mL triangular flask, adding activated strain, culturing at 28 deg.C and 180rpm/min for 3 days to obtain seed solution.
Mass fermentation: a total of 10 flasks were fermented using a 500mL Erlenmeyer flask, 150mL per flask of the medium, and the seed solution was inoculated into a PDB medium containing sodium pyruvate at an inoculum size of 10% and cultured at 28 ℃ at 180rpm/min for 7 days.
Extracting and separating; and combining 3 bottles of fermentation liquor, extracting the fermentation liquor for 3 times by using ethyl acetate, combining ethyl acetate extracting solutions, performing spin-drying to obtain a crude extract 630mg, separating by using a silica gel column to obtain a target product 183mg, and identifying the target product to be 4-hydroxyphenylethanol by using nuclear magnetic resonance analysis.
The product of this example has a hydrogen nuclear magnetic resonance carbon spectrum represented by 1H NMR (400MHz, CD) in FIGS. 1 and 23OD-d 4. delta.7.03 (2H, d, J. is 8.3Hz, H-3, H-5),6.71(2H, d, J. is 8.3Hz, H-2, H-6),3.69(2H, t, J. is 7.2Hz, H-8),2.71(2H, t, J. is 7.2Hz, H-7).13C NMR (400MHz, CD3OD-d 4). delta.155.3 (C-1),129.5(C-3, C-5),114.8(C-2, C-6),63.2(C-8),38.0(C-7). The above results were compared with Luyulin et al [ Huangyulin, Marilui, Rong, Lixiong, Liu, Liudeb, and Persper, J. secondary mold metabolite [ J. ] research ]Chinese patent medicine 2017,39(07):1415-1419]The reported literature control confirmed that the substance was 4-hydroxyphenylethanol.
Example 2
Preparing a culture medium: 35g of PDB culture medium dry powder, 100 mu M of sodium pyruvate and 1L of distilled water, adjusting the pH value to 7.0, and carrying out autoclaving at 121 ℃ for 20 min.
Preparing a seed solution: adding 100mL of culture medium into a 500mL triangular flask, adding activated strain, culturing at 26 deg.C and 150rpm/min for 5 days to obtain seed solution.
Mass fermentation: a total of 10 flasks were fermented using a 500mL Erlenmeyer flask, 150mL per flask of the medium, and the seed solution was inoculated into a PDB medium containing sodium pyruvate at an inoculum size of 10% and cultured at 26 ℃ at 150rpm/min for 7 days.
Extracting and separating; and combining 3 bottles of fermentation liquor, extracting the fermentation liquor for 3 times by using ethyl acetate, combining ethyl acetate extracting solutions, performing spin-drying to obtain 603mg of crude extract, and separating by using a silica gel column to obtain 149mg of a target product. The target product was identified as 4-hydroxyphenylethanol using nuclear magnetic resonance analysis.
Example 3
Preparing a culture medium: 35g of PDB culture medium dry powder, 500 mu M of sodium pyruvate and 1L of distilled water, adjusting the pH value to 7.5, and carrying out autoclaving at 121 ℃ for 20 min.
Preparing a seed solution: adding 100mL of culture medium into a 500mL triangular flask, adding activated strain, culturing at 30 deg.C and 170rpm/min for 2 days to obtain seed solution.
Mass fermentation: a total of 10 flasks were fermented using a 500mL Erlenmeyer flask, 150mL per flask of the medium, and the seed solution was inoculated into a PDB medium containing sodium pyruvate at an inoculum size of 15% and cultured at 30 ℃ at 170rpm/min for 7 days.
Extracting and separating; and combining 3 bottles of fermentation liquor, extracting the fermentation liquor for 3 times by using ethyl acetate, combining ethyl acetate extracting solutions, performing spin-drying to obtain 579mg of crude extract, and separating by using a silica gel column to obtain 140mg of a target product. The target product was identified as 4-hydroxyphenylethanol using nuclear magnetic resonance analysis.
Example 4
Preparing a culture medium: 35g of PDB culture medium dry powder, 50 mu M of sodium pyruvate and 1L of distilled water, adjusting the pH value to 7.0, and carrying out autoclaving at 121 ℃ for 20 min.
Preparing a seed solution: adding 100mL of culture medium into a 500mL triangular flask, adding activated strain, culturing at 28 deg.C and 180rpm/min for 3 days to obtain seed solution.
Mass fermentation: a total of 10 flasks were fermented using a 500mL Erlenmeyer flask, 150mL per flask of the medium, and the seed solution was inoculated into a PDB medium containing sodium pyruvate at an inoculum size of 5% and cultured at 28 ℃ at 180rpm/min for 7 days.
Extracting and separating; and combining 3 bottles of fermentation liquor, extracting the fermentation liquor for 3 times by using ethyl acetate, combining ethyl acetate extracting solutions, performing spin-drying to obtain 401mg of crude extract, and separating by using a silica gel column to obtain 83mg of a target product. The target product was identified as 4-hydroxyphenylethanol using nuclear magnetic resonance analysis.
Example 5
Preparing a culture medium: 35g of PDB culture medium dry powder, 300 mu M of sodium pyruvate, 1L of distilled water, pH value adjustment of 8.0 and autoclaving at 121 ℃ for 20 min.
Preparing a seed solution: adding 100mL of culture medium into a 500mL triangular flask, adding activated strain, culturing at 28 deg.C and 170rpm/min for 3 days to obtain seed solution.
Mass fermentation: a total of 10 flasks were fermented using a 500mL Erlenmeyer flask, 150mL per flask of the medium, and the seed solution was inoculated into a PDB medium containing sodium pyruvate at an inoculum size of 10% and cultured at 28 ℃ at 170rpm/min for 7 days.
Extracting and separating; and combining 3 bottles of fermentation liquor, extracting the fermentation liquor for 3 times by using ethyl acetate, combining ethyl acetate extracting solutions, performing spin-drying to obtain 598mg of crude extract, and separating by using a silica gel column to obtain 139mg of a target product. The target product was identified as 4-hydroxyphenylethanol using nuclear magnetic resonance analysis.
Example 6
Preparing a culture medium: 35g of PDB culture medium dry powder, 250 mu M of sodium pyruvate and 1L of distilled water, adjusting the pH value to 5.0, and carrying out autoclaving at 121 ℃ for 20 min.
Preparing a seed solution: adding 100mL culture medium into 500mL triangular flask, adding activated strain, culturing at 28 deg.C and 170rpm/min for 5 days to obtain seed solution.
Mass fermentation: a total of 10 flasks were fermented using a 500mL Erlenmeyer flask, 150mL per flask of the medium, and the seed solution was inoculated into a PDB medium containing sodium pyruvate at an inoculum size of 15% and cultured at 28 ℃ at 150rpm/min for 10 days.
Extracting and separating; and combining 3 bottles of fermentation liquor, extracting the fermentation liquor for 3 times by using ethyl acetate, combining ethyl acetate extracting solution, performing spin-drying to obtain 570mg of crude extract, and separating by using a silica gel column to obtain 111mg of a target product. The target product was identified as 4-hydroxyphenylethanol using nuclear magnetic resonance analysis.
Example 7
Preparing a culture medium: 35g of PDB culture medium dry powder and 1L of distilled water, adjusting the pH value to 7.0, and carrying out autoclaving at 121 ℃ for 20 min.
Preparing a seed solution: adding 100mL of culture medium into a 500mL triangular flask, adding activated strain, culturing at 28 deg.C and 170rpm/min for 3 days to obtain seed solution.
Mass fermentation: a total of 10 flasks were fermented in a 500mL Erlenmeyer flask, 150mL of the medium was placed in each flask, and the seed solution was inoculated into the PDB medium at an inoculum size of 10% and cultured at 28 ℃ at 150rpm/min for 7 days.
Extracting and separating; and combining 3 bottles of fermentation liquor, extracting the fermentation liquor for 3 times by using ethyl acetate, combining ethyl acetate extracting solutions, performing spin-drying to obtain a crude extract 730mg, and separating by using a silica gel column to obtain a target product 18 mg. The target product was identified as 4-hydroxyphenylethanol using nuclear magnetic resonance analysis.
Compared with the common endophytic fungi fermentation product, the 4-hydroxyphenylethanol prepared by the method has the advantages that the yield is greatly improved, the yield is up to 122mg/L, the operation is simple, and the industrial large-scale production can be carried out; in the technical scheme, sodium pyruvate is used as an epigenetic modifier, so that the raw materials are easy to obtain, and the economic cost is low; the method is simple to operate in the separation and purification process, and can effectively reduce the production cost.
The foregoing shows and describes the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are merely illustrative of the principles of the invention, but that various changes and modifications may be made without departing from the spirit and scope of the invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (7)

1. A method for improving the yield of 4-hydroxyphenylethanol of a fermentation product of endophytic fungi by epigenetics transformation is characterized in that: the method comprises the following operation steps:
s1, preparing seed liquid: adding the activated strain into PDB culture medium containing sodium pyruvate, and culturing for 2-7 days to obtain seed liquid;
s2, large-scale fermentation: inoculating the seed solution into a PDB culture medium containing sodium pyruvate according to a certain proportion, and culturing for 7-10 days at the temperature of 25-30 ℃ and the speed of 120-180 rpm/min;
s3, extracting and separating; extracting the fermentation liquor with ethyl acetate for 3 times, combining ethyl acetate extract, spin-drying, and separating with silica gel column to obtain the target product.
2. The method for improving the yield of 4-hydroxyphenylethanol which is a fermentation product of an endophytic fungus by epigenetic transformation according to claim 1, wherein: in step S1, the bacterial species is Arthrinium arendinis.
3. The method for improving the yield of 4-hydroxyphenylethanol which is a fermentation product of an endophytic fungus by epigenetic transformation according to claim 1, wherein: in step S1, the culture condition is 25-30 ℃ and the rotation speed is 120-180 rpm/min.
4. The method for improving the yield of 4-hydroxyphenylethanol, a fermentation product of an endophytic fungus, according to claim 1, by epigenetic modification, wherein: the epigenetic modifier used in the PDB culture medium in the step S1 is sodium pyruvate, the content of the sodium pyruvate is 50-500 mu M, and the pH value of the culture medium is 5-8.
5. The method for improving the yield of 4-hydroxyphenylethanol, a fermentation product of an endophytic fungus, according to claim 1, by epigenetic modification, wherein: inoculation ratio in step S2: 5 to 15 percent.
6. The method for improving the yield of 4-hydroxyphenylethanol, a fermentation product of an endophytic fungus, according to claim 1, by epigenetic modification, wherein: the culture conditions in step S2 were 28 ℃ and 170rpm/min, and the culture was carried out for 7 days.
7. The method for improving the yield of 4-hydroxyphenylethanol which is a fermentation product of an endophytic fungus by epigenetic transformation according to claim 1, wherein: and step S3, wherein the extraction solvent is ethyl acetate, and the target product is obtained by separating and purifying through a silica gel column.
CN202210157876.1A 2022-02-21 2022-02-21 Method for improving yield of endophytic fungi fermentation product 4-hydroxyphenylethanol through epigenetic transformation Pending CN114517214A (en)

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CN109971651A (en) * 2017-12-27 2019-07-05 中国农业科学院烟草研究所 A kind of tobacco endogenetic fungus and its preparing the application in 5,8 peroxide of ergosterol
CN112940950A (en) * 2021-04-29 2021-06-11 广西壮族自治区农业科学院 Arthropodium fungus strain and application thereof
CN113265339A (en) * 2021-06-30 2021-08-17 广西壮族自治区农业科学院 Strain LX911 capable of secreting melezin and application thereof

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