CN108611278B - Method for preparing phenazocine through microbial fermentation and bacterial strain thereof - Google Patents
Method for preparing phenazocine through microbial fermentation and bacterial strain thereof Download PDFInfo
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Abstract
The invention discloses a method for preparing phenazocine by microbial fermentation and a strain thereof. The invention provides an application of pseudomorphas pannorum BJZ13 in preparation of phenazocine; the preservation registration number of the pseudogenomics pannoum BJZ13 in the common microorganism center of China Committee for culture Collection of microorganisms is CGMCC No. 15389. The finazocine can be obtained after the pseudozymococcus panorum BJZ13 is fermented and cultured, the operation is simple, the cost is low, the production period is short, and the application potential of industrial scale production is realized. The invention provides a new way for the resource development of finazocine medicines.
Description
Technical Field
The invention relates to the field of biochemistry, and particularly relates to a method for preparing phenazocine through microbial fermentation and a strain thereof.
Background
Finazocine is an opioid analgesic, and has a similar effect to pentazocine. Finafloxacin has an analgesic effect 4 times as potent as morphine, does not cause sphincter spasm of Oddi, and is a more suitable drug for treating biliary or pancreatic pain than morphine.
Finazocine is currently produced mainly by chemical synthesis. The method for producing the phenazocine by using the microorganism can obtain the phenazocine monomer with higher purity, thereby avoiding the residue of a chemical synthesis by-product, and the microorganism is a living body as a synthesis place, and the waste of resources and the damage to the environment can be avoided by using the self resources of the organism to produce the phenazocine medicine. The microorganism is easy to propagate and culture in a large amount, has simple operation, low cost and short production period, has application potential of industrial scale production, and is an ideal way for producing the phenazocine medicament.
Disclosure of Invention
The invention aims to provide a method for preparing phenazocine by microbial fermentation.
In a first aspect, the present invention claims the use of pseudomorphas panorum BJZ13 for the preparation of phenazocine.
Wherein, the pseudogenomics pannorum BJZ13 has been preserved in China general microbiological culture Collection center (CGMCC for short, the address is No. 3 of West Lu No.1 of Beijing Korean district, institute of microbiology of China academy of sciences) in 2018, 3.8.8.s..
In a second aspect, the invention claims a process for preparing phenazocine.
The method for preparing the phenazocine provided by the invention can comprise the following steps: fermenting and culturing the pseudogenomonas pannorum BJZ13 to obtain phenazocine.
Further, the solvent of the culture medium for fermentation culture is water, and the solutes and the concentrations are as follows: soluble starch 20g/L, FeCl3 0.00065g/L，MgSO4 0.5g/L，KH2PO4 0.5g/L，(NH4)2SO40.65g/L, 1 mul/ml ampicillin; the pH is 7.2-7.4.
Further, the conditions of the fermentation culture may specifically be: shaking and culturing at 28 deg.C and 120r/min for 34 days.
Further, the method also comprises a step of separating a bacterial liquid from a fermentation system obtained by the fermentation culture. Specifically, filter paper can be used to separate bacterial liquid from the fermentation system obtained by fermentation culture. The filter paper can be specifically as follows: the qualitative filter paper (102) is medium speed.
Further, the method also comprises the step of extracting the bacterial liquid by using an organic solvent. The organic solvent may be ethyl acetate and dichloromethane.
Further, the extraction of the bacterial solution with ethyl acetate and dichloromethane can be performed according to a method comprising the following steps: extracting the bacterial liquid by using ethyl acetate; distilling the obtained ethyl acetate phase under reduced pressure to obtain extract; and extracting the obtained extract by using dichloromethane, and distilling under reduced pressure to obtain a dichloromethane phase extract.
Wherein, the step of extracting the bacterial liquid by using ethyl acetate can be a step of extracting the bacterial liquid for multiple times (for example, three times) by using ethyl acetate; the extracted matter of the latter extraction is the water phase obtained in the former extraction.
More specifically, the extraction of the bacterial liquid with ethyl acetate and dichloromethane can be performed according to a method comprising the following steps:
(1) extracting the bacterial liquid with equal volume of ethyl acetate (selecting a separating funnel with proper volume, sequentially adding equal volume of bacterial liquid and ethyl acetate, fully oscillating), standing at room temperature until an ethyl acetate phase and a water phase are separated, and respectively collecting the water phase and the ethyl acetate phase;
(2) taking the water phase obtained in the step (1), adding ethyl acetate with the same volume for extraction (full oscillation), then standing at room temperature until an ethyl acetate phase and the water phase are separated, and respectively collecting the water phase and the ethyl acetate phase;
(3) taking the water phase obtained in the step (2), adding ethyl acetate with the same volume for extraction (full oscillation), then standing at room temperature until an ethyl acetate phase and the water phase are separated, and respectively collecting the water phase and the ethyl acetate phase;
(4) combining the ethyl acetate phase obtained in the step (1), the ethyl acetate phase obtained in the step (2) and the ethyl acetate phase obtained in the step (3), and distilling under reduced pressure to obtain an extract;
(5) and (3) extracting the extract obtained in the step (4) by using dichloromethane (specifically, standing for 1 hour at room temperature after the dichloromethane fully permeates the extract), and distilling under reduced pressure to obtain a dichloromethane phase extract (also called as crude extract).
Further, the method also comprises a step of obtaining the phenazocine from the dichloromethane phase extract (crude extract).
Further, the finazocine can be obtained from the dichloromethane phase extract by the following steps: and dissolving the dichloromethane phase extract (crude extract) by dichloromethane, filtering by a 0.45-micron microporous filter membrane, collecting filtrate, carrying out gas chromatography-mass spectrometry detection, and collecting a peak with retention time of 25.222min to obtain the finazocine.
Wherein, the gas chromatography conditions adopted during the gas chromatography-mass spectrometry combined detection can be as follows: bruker 320 triple quadrupole gas chromatography-mass spectrometer, DB-5MS dedicated capillary chromatographic column (0.25mm × 0.25 μm × 30m), high purity helium (99.999%) as carrier gas, and volume flow rate of 1.0mL min-1(ii) a A sample inlet is 250 ℃; the sample introduction amount is 1 mu L, and the sample introduction is not carried out by shunting; the initial column temperature was 50 deg.C, held for 5min, then heated to 290 deg.C at a rate of 10 deg.C/min, and held for 11 min.
The mass spectrometry conditions adopted in the gas chromatography-mass spectrometry combined detection can be as follows: the EI source temperature is 200 ℃; a transmission line is 250 ℃; electron energy 70 eV; mass spectrum scanning range is 45-800 Da.
In a third aspect, the invention also claims the pseudonymphaascus panorum BJZ 13.
The invention discloses a new application of pseudogenomics pannorum BJZ13, namely that finazocine can be obtained after pseudogenomics pannorum BJZ13 fermentation culture, the operation is simple, the cost is low, the production period is short, and the application potential of industrial scale production is realized. The invention provides a new way for the resource development of finazocine medicines.
Deposit description
Suggested classification nomenclature: pseudogenococcus panorum
According to the biological materials (strains): BJZ13
The preservation organization: china general microbiological culture Collection center
The preservation organization is abbreviated as: CGMCC (China general microbiological culture Collection center)
Address: xilu No.1 Hospital No. 3 of Beijing market facing Yang district
The preservation date is as follows: 3, 8 months in 2018
Registration number of the preservation center: CGMCC No.15389
Drawings
FIG. 1 is a GC-MS total ion flow diagram.
FIG. 2 is a mass spectrum at 25.222min retention time and comparison with NIST database.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The quantitative tests in the following examples, all set up three replicates and the results averaged.
Filter paper: hangzhou special paper industry Co., Ltd, the qualitative filter paper (102) is cut at medium speed and diameter of 9-15cm as required.
Example 1 acquisition and characterization of Pseudomonas panorum BJZ13
1. Pretreatment: the harvested plants of the trichophyton sanctum were harvested with sterile water [ harvested at 2015, 8 months and 8 days. Location in new Orthon area of Isvalba (Svalbard) Islands of North Pole region (
78 degrees 54 '01.242' N, 12 degrees 09 '33.816' E) are cleaned.
2. Plant surface disinfection: cutting cleaned Trichophyton japonicus under aseptic condition, sterilizing with 75% ethanol for 1min, washing with sterile water for 1min, and washing for 5 times.
3. Culturing symbiotic bacteria: under aseptic conditions, the surface-sterilized bryophytes were spread evenly on the medium. Culturing at 15 deg.C for 5-15 days. The components of the culture medium: soluble starch 20g/L, FeCl3 0.00065g/L，MgSO4 0.5g/L，KH2PO4 0.5g/L，(NH4)2SO40.65g/L, pH 7.2-7.4, agar 2%, autoclaving at 121 deg.C for 20min, adding ampicillin to a final concentration of 1 μ L/ml.
4. And (3) purifying symbiotic bacteria: after culturing for several days in a constant temperature incubator, gradually picking up newly grown thalli on a new plate under the aseptic condition, forming bacterial colonies after several days, preliminarily judging the strain types according to the difference of colony morphology and color and the growth time of the bacterial colonies, picking out different bacterial strains and respectively inoculating the different bacterial strains on the new plate, and repeating the operations until pure bacterial colonies are separated out.
5. And (3) strain identification: the purified strain is inoculated on a flat plate and sent to Beijing Liu-He Hua Dageney science and technology Limited company for sequencing identification. The purified fungus is subjected to 18S sequencing, the ITS sequence length is 570bp, and the sequence is shown as SEQ ID No. 1. The strain had a homology of 99% with Pseudomonas panorum (Geomomyces panorum) as determined by sequence alignment, and was thus designated Pseudomonas panorum BJZ 13.
That is, the BJZ13 strain was identified as Pseudomonas panorum. Pseudo-zymograms pannorum BJZ13 has been deposited in China general microbiological culture Collection center (CGMCC, No. 3 of West Lu 1 of Beijing, Chaoyang, China academy of sciences microbiological research institute) at 3.8.2018, and the deposited registration number is CGMCC No. 15389.
Example 2 preparation of finazocine Using Pseudogenomics pannorum BJZ13
First, culture of Pseudogenomics pannorum BJZ13
The fermentation medium comprises the following components: soluble starch 20g, FeCl3 0.00065g，MgSO4 0.5g，KH2PO40.5g，(NH4)2SO40.65g, adding distilled water to a constant volume of 1000 mL. The preparation method of the culture medium specifically comprises the following steps: weighing 20g of soluble starch, putting the soluble starch into a beaker, heating the soluble starch until the solution is clear, cooling the solution to room temperature, adding FeCl3、MgSO4、KH2PO4、(NH4)2SO4Adding water to a volume of slightly less than 1000ml, adjusting the pH value to 7.2-7.4 by using 2mol/L NaOH, and supplementing water to 1000 ml. 200ml of the liquid medium was placed in a 500ml Erlenmeyer flask at 121 ℃ for 20min, and after autoclaving, ampicillin was added to a final concentration of 1. mu.l/ml for further use.
A single colony of Pseudomonas panorum BJZ13 was inoculated into 200ml of the above fermentation medium and cultured with shaking at 120r/min at 28 ℃ for 34 days.
Secondly, preparing a crude extract
1. And (4) taking the fermentation system obtained in the step one, and separating and collecting the bacterial liquid by using filter paper.
2. Taking the bacterial liquid (about 200ml) obtained in the step 1, extracting with 200ml of ethyl acetate, selecting a separating funnel with the volume of 1L, sequentially adding the bacterial liquid and the ethyl acetate, fully oscillating, standing at room temperature until an ethyl acetate phase and a water phase are separated, and respectively collecting the water phase and the ethyl acetate phase;
3. taking the water phase (about 200ml) obtained in the step 2, adding 200ml of ethyl acetate, fully oscillating, standing at room temperature until the ethyl acetate phase and the water phase are separated, and respectively collecting the water phase and the ethyl acetate phase;
4. taking the water phase (about 200ml) obtained in the step 3, adding 200ml of ethyl acetate, fully oscillating, standing at room temperature until the ethyl acetate phase and the water phase are separated, and respectively collecting the water phase and the ethyl acetate phase;
5. and (4) combining the ethyl acetate phase obtained in the step (2), the ethyl acetate phase obtained in the step (3) and the ethyl acetate phase obtained in the step (4), and distilling under reduced pressure to obtain an extract.
6. And (3) extracting the extract obtained in the step (5) by using dichloromethane, fully permeating the dichloromethane into the extract, standing for 1 hour at room temperature, and distilling under reduced pressure to obtain a dichloromethane phase extract (also called crude extract).
Third, GC-MS analysis
And (4) taking the crude extract obtained in the step two 6, dissolving the crude extract by using dichloromethane, filtering the solution by using a 0.45-micron microporous filter membrane, collecting filtrate, and performing GC-MS online identification.
Gas chromatography conditions: bruker 320 triple quadrupole gas chromatography-mass spectrometer, DB-5MS special capillary chromatographic column (0.25mm multiplied by 0.25um multiplied by 30m), high purity helium (99.999%) as carrier gas, and 1.0mL min of volume flow-1(ii) a A sample inlet is 250 ℃; the sample introduction amount is 1 mu L, and the sample introduction is not carried out by shunting; the initial column temperature was 50 deg.C, held for 5min, then heated to 290 deg.C at a rate of 10 deg.C/min, and held for 11 min.
Mass spectrum conditions: the EI source temperature is 200 ℃; a transmission line is 250 ℃; electron energy 70 eV; mass spectrum scanning range is 45-800 Da.
The GC-MS total ion flow diagram is shown in FIG. 1.
The mass spectrum at retention time 25.222min is compared with NIST database as shown in FIG. 2.
And (4) separating 20 peaks from the crude extract obtained in the step two 6. The identification of the mass spectrogram corresponding to the chromatographic peak is carried out by a positive and negative retrieval method of a mass spectrogram library of an NIST database, and the peak with the retention time of 25.222min is identified as finazocine.
The structural formula of phenazocine is as follows:
<110> university of Beijing teachers
<120> a method for preparing phenazocine by microbial fermentation and a strain thereof
<130> GNCLN180735
<160> 1
<170> PatentIn version 3.5
<210> 1
<211> 570
<212> DNA
<213> Pseudogymnoascus pannorum
<400> 1
tttccgtagg gtgacctgcg gaaggatcat tacagtagtc gcccgggttg ccgcaaggcc 60
tcccgggtaa cctaccaccc tttgtttatt acactttgtt gctttggcaa gcctgccctc 120
gggctgctgg ctccggccgg cgagcgcttg ccagaggacc taaactctgt ttgtctatac 180
tgtctgagta ctatataata gttaaaactt tcaacaacgg atctcttggt tctggcatcg 240
atgaagaacg cagcgaaatg cgataagtaa tgtgaattgc agaattcagt gaatcatcga 300
atctttgaac gcacattgcg ccccctggta ttccgggggg catgcctgtc cgagcgtcat 360
tacaaccctc aagctcagct tggtgttggg ccccgccgcc ccggcgggcc ctaaagtcag 420
tggcggtgcc gtccggctcc gagcgtagta attcttctcg ctctggaggt ccggtcgtgt 480
gctcgccagc aacccccaat ttttttcagg ttgacctcgg atcaggtagg gatacccgct 540
gaacttaagc atatcaataa agcggaggaa 570
Claims (10)
- The use of pseudogenomics pannorum BJZ13 in the preparation of phenazocine;the preservation registration number of the pseudogenomics pannoum BJZ13 in the common microorganism center of China Committee for culture Collection of microorganisms is CGMCC No. 15389.
- 2. A process for preparing phenazocine, comprising the steps of: carrying out fermentation culture on pseudogenomics pannorum BJZ13 to obtain phenazocine;the preservation registration number of the pseudogenomics pannoum BJZ13 in the common microorganism center of China Committee for culture Collection of microorganisms is CGMCC No. 15389.
- 3. The method of claim 2, wherein: the method also comprises a step of separating bacterial liquid from a fermentation system obtained by the fermentation culture.
- 4. The method of claim 3, wherein: the method also comprises the step of extracting the bacterial liquid by using an organic solvent.
- 5. The method of claim 4, wherein: the organic solvent is ethyl acetate and dichloromethane.
- 6. The method of claim 5, wherein: the extraction of the bacterial liquid by adopting ethyl acetate and dichloromethane is carried out according to the method comprising the following steps: extracting the bacterial liquid by using ethyl acetate; distilling the obtained ethyl acetate phase under reduced pressure to obtain extract; and extracting the obtained extract by using dichloromethane, and distilling under reduced pressure to obtain a dichloromethane phase extract.
- 7. The method of claim 6, wherein: the extraction of the bacterial liquid by adopting ethyl acetate and dichloromethane is carried out according to the method comprising the following steps:(1) extracting the bacterial liquid with ethyl acetate with the same volume, and respectively collecting a water phase and an ethyl acetate phase;(2) taking the water phase obtained in the step (1), adding ethyl acetate with the same volume for extraction, and respectively collecting the water phase and the ethyl acetate phase;(3) taking the water phase obtained in the step (2), adding ethyl acetate with the same volume for extraction, and respectively collecting the water phase and the ethyl acetate phase;(4) combining the ethyl acetate phase obtained in the step (1), the ethyl acetate phase obtained in the step (2) and the ethyl acetate phase obtained in the step (3), and distilling under reduced pressure to obtain an extract;(5) and (4) extracting the extract obtained in the step (4) by using dichloromethane, and distilling under reduced pressure to obtain the dichloromethane phase extract.
- 8. The method according to claim 6 or 7, characterized in that: the method also comprises a step of obtaining phenazocine from the dichloromethane phase extract.
- 9. The method of claim 8, wherein: the finazocine is obtained from the dichloromethane phase extract by the method comprising the following steps: and (3) carrying out gas chromatography-mass spectrometry detection on the dichloromethane phase extract, and collecting a peak with the retention time of 25.222min to obtain the finazocine.
- 10, pseudogenomics pannorum BJZ13, wherein the preservation registration number of the China general microbiological culture Collection center is CGMCC No. 15389.
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