CN116676231A - Weissella antrum producing trans-2-decenoic acid and application thereof - Google Patents

Weissella antrum producing trans-2-decenoic acid and application thereof Download PDF

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CN116676231A
CN116676231A CN202310684058.1A CN202310684058A CN116676231A CN 116676231 A CN116676231 A CN 116676231A CN 202310684058 A CN202310684058 A CN 202310684058A CN 116676231 A CN116676231 A CN 116676231A
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decenoic acid
weissella
trans
antrum
fermentation
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赵秋伟
李寅
于惠
郑蕾
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Institute of Microbiology of CAS
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Institute of Microbiology of CAS
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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Abstract

The invention belongs to the field of biology, and particularly relates to a Weissella food for producing trans-2-decenoic acid. The antral weissella accession number: CGMCC No.25147, which is screened from Daqu of strong aromatic Chinese liquor. In one experiment, the Weissella antrum of the present invention produced trans-2-decenoic acid in an amount of up to 2.382mg/L after 2 days of continuous fermentation, and thus was useful for providing a precursor for the synthesis of 10-hydroxy-2-decenoic acid, and for studying metabolic pathways, and for advancing the biosynthesis process of trans-2-decenoic acid.

Description

Weissella antrum producing trans-2-decenoic acid and application thereof
Technical Field
The invention belongs to the field of biology, and particularly relates to a antral Weissella (Weissella cibaria antral Weissella) strain for producing trans-2-decenoic acid and application thereof.
Background
The molecular formula of the trans-2-decenoic acid is one of medium chain alpha, beta-unsaturated fatty acid, can be used as an intermediate of important products such as nerve drugs, spices, health-care products and the like, and has very wide application value.
Studies have shown that trans-2-decenoic acid and its derivatives have particular therapeutic effects in the treatment of neurological diseases, and can be used in drug development, for example, as an important active factor for the synthesis of royal jelly, 10-hydroxy-2-decenoic acid. 10-hydroxy-2-decenoic acid has important activities of bacteriostasis, anticancer, immunoregulation and the like, and in natural environment, 10-hydroxy-2-decenoic acid only exists in the maxillary gland of a worker bee, so that the biosynthesis of trans-2-decenoic acid lays a foundation for the future biosynthesis pathway of 10-hydroxy-2-decenoic acid. In addition to medical uses, trans-2-decenoic acid has great utility in materials, such as the synthesis of high quality nanorod materials using 2-decenoic acid as a lead ligand.
Currently, trans-2-decenoic acid is produced chemically and is expensive to about 3 tens of thousands/kg. Therefore, the further research on the efficient and green synthesis mode of the trans-2-decenoic acid has important significance for the further development and exploration of the application value of the trans-2-decenoic acid.
Disclosure of Invention
The antral Weissella producing trans-2-decenoic acid is obtained by screening from the strong aromatic white spirit Daqu, and can be used for providing precursor substances for the synthesis of 10-hydroxy-2-decenoic acid, researching metabolic pathways and promoting the biosynthesis process of trans-2-decenoic acid.
Therefore, the invention provides a strain of antral Weissella producing trans-2-decenoic acid, which is preserved in China general microbiological culture Collection center (CGMCC) for 6-month 21 of 2022, with the preservation number: CGMCC No.25147, the classification name is Weissella antrum (Weissella cibaria Weissella antrum).
The invention also provides an application of the Weissella antrum in producing trans-2-decenoic acid.
Specifically, the antral weissella is in a fermentation medium to produce trans-2-decenoic acid.
Preferably, the fermentation culture condition is static culture at 35-38deg.C for 1-4 days, and pH value is 7.0.
More preferably, the inoculation amount of Weissella food is 1.5-2.5% (the concentration of the strain in the selected inoculated bacterial liquid is up toTo 10 7 cfu/mL)。
In one embodiment, the composition of the fermentation medium is: the medium contained 16g glucose, 10g tryptone, 2.5g yeast powder, 5g beef extract, 3.85g beef brain, 4.9g beef heart, 0.5g tween 80,1g ammonium citrate, 2.5g sodium chloride, 2.5g anhydrous sodium acetate, 0.05g magnesium sulfate, 0.025g manganese sulfate, 1.25g disodium hydrogen phosphate, 1g dipotassium hydrogen phosphate per liter.
In addition, a step of further extracting trans-2-decenoic acid is included. Preferably, a headspace solid-phase microextraction method is adopted, supernatant obtained by centrifuging fermentation liquor is taken, added into a headspace bottle, saturated NaCl solution is added, the prepared sample is subjected to heat preservation and balance for 4-6min at 50-70 ℃, and then the prepared sample is extracted for 40-60min at 50-70 ℃ by using a 50/30 mu mDVB/CAR/PDMS extraction head.
The present invention also provides a method of preparing trans-2-decenoic acid by fermenting the antral weissella in a fermentation medium to produce trans-2-decenoic acid, and a step of extracting trans-2-decenoic acid.
Preferably, the fermentation culture is carried out at 35-38deg.C for 1-4 days at pH 7.0.
The Weissella antrum provided by the invention has the capability of producing trans-2-decenoic acid by fermentation, is derived from Daqu of strong aromatic white spirit, can stably express trans-2-decenoic acid, has simple culture conditions, and can be used for providing precursor substances for synthesizing 10-hydroxy-2-decenoic acid, researching metabolic pathways and promoting the biosynthesis process of trans-2-decenoic acid.
Drawings
FIG. 1 is a mass spectrum of GC-MS molecular fragments of trans-2-decenoic acid produced by the strain of example 2.
FIG. 2 is a GC-MS molecular fragment mass spectrum of the trans-2-decenoic acid standard of example 2.
Strain preservation information:
the Weissella antrum of the invention is preserved in China general microbiological culture Collection center, CGMCC for short, in 2022, 6 and 21 days, and the preservation unit address is North Chen Xili No. 1 and 3 in the Korea of Beijing city of China. The preservation number of the strain is CGMCC NO.25147, and the strain is classified and named as Weissella food Weissella cibaria.
Detailed Description
The invention will be further illustrated by the following specific examples in order to provide a better understanding of the invention, but without limiting the invention thereto.
The medium formulation referred to in the examples:
MRS liquid medium: glucose 20g/L, peptone 10g/L, yeast powder 4g/L, beef extract powder 5g/L, tween 80 1g/L, triammonium citrate 2g/L, sodium acetate 5g/L, magnesium sulfate 0.2g/L, manganese sulfate 0.05g/L, dipotassium hydrogen phosphate 1g/L, pH6.0, and high pressure steam sterilization at 115 ℃ for 20 minutes.
MRS solid medium: 15g/L agar was added to the MRS broth and autoclaved at 115℃for 20 minutes.
Fermentation medium: 16g/L glucose, 10g/L tryptone, 2.5g/L yeast powder, 5g/L beef extract, 3.85g/L beef brain, 4.9g/L beef heart, 0.5g/L Tween 80, 1g/L ammonium citrate, 2.5g/L sodium chloride, 2.5g/L anhydrous sodium acetate, 0.05g/L magnesium sulfate, 0.025g/L manganese sulfate, 1.25g/L disodium hydrogen phosphate, 1g/L dipotassium hydrogen phosphate, pH6.0 and high pressure steam sterilization at 115 ℃ for 20 minutes.
Example 1: isolation and purification of strains
1) The separation method comprises the following steps: taking 20g of Luzhou Laojiao Luzhou flavor liquor Daqu sample, putting the sample into a conical flask filled with 180mL of sterile distilled water, oscillating for 10min by a constant-temperature shaking table, and fully scattering and uniformly mixing the sample. Taking 1mL of sample suspension, diluting to 10 by adopting a double ratio dilution method -2 ～10 -7 100 mu L of each gradient of diluent is sucked and uniformly coated on an MRS solid culture medium plate, two plates are prepared in parallel, inverted, placed under anaerobic condition at 37 ℃ for culture for 36-48h, and observed in time.
2) And (3) scribing and purifying: and taking out the plate with the colonies, picking single colonies with different colony morphologies, and carrying out secondary streaking until all the single colonies are purified.
3) And (3) strain preservation: and (3) picking single colonies of each strain after purification into a 5mLMRS liquid culture medium, standing and culturing at 37 ℃ under anaerobic condition for 20-24 hours, sucking 1mL of bacterial liquid into a bacteria-preserving tube, adding 0.5mL of 60% sterile glycerol solution, re-suspending, and preserving at-80 ℃.
Example 2: trans-2-decenoic acid production ability assay
(1) Preparing a bacterial liquid to be tested:
after the glycerol preservation tube of the strain obtained by screening is dissolved, the glycerol preservation tube is respectively inoculated into MRS liquid culture medium, and the strain is subjected to stationary culture for 20 hours at 37 ℃ to obtain bacterial liquid to be detected.
(2) GC-MS method for detecting trans-2-decenoic acid:
adopts a headspace solid-phase microextraction method: taking supernatant, adding the supernatant into a headspace bottle, adding saturated NaCl solution, keeping the temperature of the prepared sample at 60 ℃ for 5min, extracting the sample by using a 50/30 mu mDVB/CAR/PDMS extraction head at 60 ℃ for 50min, and desorbing the sample at 250 ℃ for 5min at a GC sample inlet after the extraction is finished. And (5) matching the compound search result with an NIST standard spectrum library, and confirming that the similarity reaches more than 80% as a target compound.
GC-MS detection chromatographic conditions:
gas chromatography conditions: HP-INNOWAX column (60 m. Times.0.25 mm. Times.0.25 μm); heating program: the initial temperature is 40 ℃, kept for 5min, and is increased to 100 ℃ at 4 ℃/min, and is increased to 230 ℃ at 6 ℃/min,
maintaining for 10min, wherein the carrier gas is high-purity helium (1.0 mL/min); the temperature of the sample inlet is 250 ℃, and the flow is not split.
Mass spectrometry conditions: electron ionization source with electron energy of 70eV; electron multiplier voltage 350V; the ion source temperature is 230 ℃; the temperature of the transmission line is 250 ℃; the mass range is 40-450 m/z.
The screening is carried out by the detection method so as to obtain a strain with the capability of producing trans-2-decenoic acid, and the strain is selected for further research.
Example 3: molecular characterization
And (3) amplifying and culturing the target strain, taking fresh bacterial liquid in the logarithmic growth phase, centrifugally collecting bacterial cells, and extracting genome DNA by using a bacterial genome extraction kit. The bacillus universal primer 27F/1541R is adopted to amplify the full-length sequence of the 16S rDNA, and the method is concretely as follows:
27F(5′-AGAGTTTGATCCTGGCTCAG-3′)
1541R(5′-AAGGAGGTGATCCAGCC-3′)
(1) reaction system (50 μl)
(2) Reaction procedure
The PCR products were checked by electrophoresis on a 1.0% agarose gel at a voltage of about 11V/cm for 20min.
The purification of PCR products was performed as described in the Shanghai Biotechnology Co small amount of gel recovery PCR product purification kit, and sequencing was performed by Shanghai Biotechnology Co. Wherein, the 16S rDNA sequence is shown as SEQ ID NO. 1: TGCAGTCGAACGCTTTGTGGTTCAACTGATTTGAAGAGCTTGCTCAGATATGACGATGGACATTGCAAAGAGTGGCGAACGGGTGAGTAACACGTGGGAAACCTACCTCTTAGCAGGGGATAACATTTGGAAACAGATGCTAATACCGTATAACAATAGCAACCGCATGGTTGCTACTTAAAAGATGGTTCTGCTATCACTAAGAGATGGTCCCGCGGTGCATTAGTTAGTTGGTGAGGTAATGGCTCACCAAGACGATGATGCATAGCCGAGTTGAGAGACTGATCGGCCACAATGGGACTGAGACACGGCCCATACTCCTACGGGAGGCAGCAGTAGGGAATCTTCCACAATGGGCGAAAGCCTGATGGAGCAACGCCGCGTGTGTGATGAAGGGTTTCGGCTCGTAAAACACTGTTGTAAGAGAAGAATGACATTGAGAGTAACTGTTCAATGTGTGACGGTATCTTACCAGAAAGGAACGGCTAAATACGTGCCAGCAGCCGCGGTAATACGTATGTTCCAAGCGTTATCCGGATTTATTGGGCGTAAAGCGAGCGCAGACGGTTATTTAAGTCTGAAGTGAAAGCCCTCAGCTCAACTGAGGAATTGCTTTGGAAACTGGATGACTTGAGTGCAGTAGAGGAAAGTGGAACTCCATGTGTAGCGGTGAAATGCGTAGATATATGGAAGAACACCAGTGGCGAAGGCGGCTTTCTGGACTGTAACTGACGTTGAGGCTCGAAAGTGTGGGTAGCAAACAGGATTAGATACCCTGGTAGTCCACACCGTAAACGATGAGTGCTAGGTGTTTGAGGGTTTCCGCCCTTAAGTGCCGCAGCTAACGCATTAAGCACTCCGCCTGGGGAGTACGACCGCAAGGTTGAAACTCAAAGGAATTGACGGGGACCCGCACAAGCGGTGGAGCATGTGGTTTAATTCGAAGCAACGCGAAGAACCTTACCAGGTCTTGACATCCCTTGACAACTCCAGAGATGGAGCGTTCCCTTCGGGGACAAGGTGACAGGTGGTGCATGGTTGTCGTCAGCTCGTGTCGTGAGATGTTGGGTTAAGTCCCGCAACGAGCGCAACCCTTATTACTAGTTGCCAGCATTTAGTTGGGCACTCTAGTGAGACTGCCGGTGACAAACCGGAGGAAGGTGGGGATGACGTCAAATCATCATGCCCCTTATGACCTGGGCTACACACGTGCTACAATGGCGTATACAACGAGTTGCCAACCCGCGAGGGTGAGCTAATCTCTTAAAGTACGTCTCAGTTCGGATTGTAGGCTGCAACTCGCCTACATGAAGTCGGAATCGCTAGTAATCGCGGATCAGCACGCCGCGGTGAATACGTTCCCGGGTCTTGTACACACCGCCCGTCACACCATGAGAGTTTGTAACACCCAAAGCCGGTGGGGTAACCTTCGGGAGCCAGCCGTCTAAGGTGGGACAGATGATTAGGGGAAGTCGAACAAGAGCC.
Sequencing the gene sequences of the obtained 16S rDNA fragments were aligned by BLAST from NCBI, strain species information was determined, identified as Weissella antrum (Weissella cibaria), and designated Weissella antrum zqw (Weissella cibaria).
Example 4: morphological and physicochemical characteristics of Weissella food zqw76
1. Experiments show that the Pediococcus pentosaceus zqw has culture characteristics: the optimal growth temperature is 37 ℃, the pH value is 7, and the growth can be realized under the conditions of facultative anaerobism, aerobics, anaerobic or micro-aerobics. In terms of temperature resistance: the strain has good growth condition at 37 ℃ and can normally grow at 42 ℃ and can not grow at 45 ℃ and 48 ℃.
2. The strain is cultured for 48 hours under the anaerobic condition at 37 ℃, and is identified by an API50CH kit, and L-arabinose, D-ribose, D-galactose, D-glucose, D-fructose, D-mannose, D-cellobiose, D-maltose, D-trehalose and D-tagatose can be respectively utilized; d-xylose, N-acetylglucosamine, amygdalin, arbutin, salicin, D-sucrose, D-gentiobiose; glycerol, mannitol, methyl-alpha D-mannopyranoside, esculin ferric citrate, D-lactose, D-melibiose, potassium gluconate, potassium 2 ketogluconate; erythritol, D-arabinose, methyl-alpha D-glucopyranoside and the like. Its utility capability is from strong to weak: l-arabinose, D-ribose, D-galactose, D-glucose, D-fructose, D-mannose, D-cellobiose, D-maltose, D-trehalose, D-tagatose; d-xylose, N-acetylglucosamine, amygdalin, arbutin, salicin, D-sucrose, D-gentiobiose; glycerol, mannitol, methyl-alpha D-mannopyranoside, esculin ferric citrate, D-lactose, D-melibiose, potassium gluconate, potassium 2 ketogluconate; erythritol, D-arabinose, methyl-. Alpha.D-glucopyranoside.
3. The bacterium is subjected to static culture for 48 hours by utilizing an MRS liquid culture medium under the microaerophilic condition at 37 ℃, and the non-volatile metabolites of the bacterium are detected by HPLC high performance liquid chromatography, so that the bacterium can be used for metabolizing and producing 8.8g/L of lactic acid, 0.14g/L of acetic acid and 3.36g/L of ethanol.
Example 5: fermentation experiment of Weissella food zqw76
After the obtained Weissella antrum zqw glycerol storage tube was dissolved, the obtained solution was inoculated into 10mL of a liquid-filled MRS medium at an inoculum size of 5%, and after standing culture at 37℃for 24 hours, the obtained solution was inoculated into a fermentation medium at an inoculum size of 2%, and continuous culture was carried out for 2 days, and the content of each component was calculated using the measurement method in example 2 and 0.822mg/mL of 2-octanol as an internal standard and a culture solution without bacterial fermentation as a blank. After the Weissella antrum zqw is fermented for 2 days, the yield of the produced trans-2-decenoic acid can reach 2.382mg/L.
Example 6: experiment for producing other volatile metabolites by fermentation of Weissella antrum zqw76
The fermentation and detection method was the same as in example 5. The detection result shows that after the Weissella antrum zqw is fermented and cultured for 2 days, 2.382mg/L of trans-2-decenoic acid can be produced, and other 23 volatile metabolites can be produced, which are respectively: 0.530mg/L of ethanol, 0.828mg/L of isoamyl alcohol, 1.296mg/L of n-heptanol, 0.076mg/L of n-octanol, 0.336mg/L of 1-nonanol, 1.540mg/L of phenethyl alcohol and 0.967mg/L of geraniol; 15.308mg/L acetic acid, 0.359mg/L isovaleric acid, 1.594mg/L caproic acid, 1.846mg/L caprylic acid, 0.404mg/L isooctanoic acid, 0.469mg/L pelargonic acid and 0.156mg/L n-capric acid; 1.451mg/L of sec-octanone; 0.618mg/L of phenylacetaldehyde and 1.497mg/L of 2, 3-dihydro-2, 6-trimethylbenzaldehyde; 2-octyl acetate 0.090mg/L,2, 4-trimethyl-1, 3-pentanediol diisobutyrate 0.366mg/L, lauryl acetate 0.424mg/L, ethyl 9-oxononanoate 0.321mg/L; phenol 0.024mg/L, methoxybenzene oxime 1.442mg/L.

Claims (10)

1. Weissella deliciosa producing trans-2-decenoic acidWeissella cibaria) It is ensured thatThe collection number is CGMCC No.25147.
2. Use of weissella antrum as claimed in claim 1 for the production of trans-2-decenoic acid.
3. The use of claim 2, wherein said antral weissella is fermented in a fermentation medium to produce trans-2-decenoic acid.
4. The use according to claim 3, wherein the fermentation culture is carried out at 35-38℃for a period of 1-4 days and at a pH of 7.0.
5. The use according to any one of claims 3 to 4, wherein the inoculation amount of Weissella food is 1.5-2.5% and the concentration of the strain in the selected inoculated bacterial liquid is up to 10 7 cfu/mL。
6. The use according to claim 5, wherein the composition of the fermentation medium is: the medium contained 16g glucose, 10g tryptone, 2.5g yeast powder, 5g beef extract, 3.85g beef brain, 4.9g beef heart, 0.5g tween 80,1g ammonium citrate, 2.5g sodium chloride, 2.5g anhydrous sodium acetate, 0.05g magnesium sulfate, 0.025g manganese sulfate, 1.25g disodium hydrogen phosphate, 1g dipotassium hydrogen phosphate per liter.
7. The use according to any one of claims 3 to 6, further comprising the step of further extracting trans-2-decenoic acid.
8. The method according to claim 7, wherein the supernatant obtained by centrifuging the fermentation broth is obtained by a headspace solid-phase microextraction method, the supernatant is added into a headspace bottle, a saturated NaCl solution is added, the prepared sample is subjected to heat preservation and balance for 4-6min at 50-70 ℃, and then the prepared sample is extracted by a 50/30 mu mDVB/CAR/PDMS extraction head at 50-70 ℃ for 40-60 min.
9. A process for preparing trans-2-decenoic acid, characterized by the steps of fermenting the antral weissella according to claim 1 in a fermentation medium to produce trans-2-decenoic acid, and extracting the trans-2-decenoic acid.
10. The method of claim 9, wherein the fermentation culture is conducted at 35-38 ℃ for a period of 1-4 days at a pH of 7.0.
CN202310684058.1A 2023-06-11 2023-06-11 Weissella antrum producing trans-2-decenoic acid and application thereof Pending CN116676231A (en)

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