CN108315361A - A method of utilizing Microbe synthesis parahydroxyben-zaldehyde - Google Patents
A method of utilizing Microbe synthesis parahydroxyben-zaldehyde Download PDFInfo
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Abstract
The invention discloses a kind of methods using Microbe synthesis parahydroxyben-zaldehyde, are production bacterium with the fungal bacterial strain Gongronella sp.w5 of soil sources, and separation is extracted from its zymotic fluid and obtains parahydroxyben-zaldehyde.Compared with chemical synthesis, the entire reaction process of the present invention carries out at normal temperatures and pressures, and pollution is small, energy consumption is small, and preparation method is simple, does not need aldehydes matter as raw material, the purity of target product is more than 98%.
Description
Technical field
The present invention relates to a kind of methods using Microbe synthesis parahydroxyben-zaldehyde.
Background technology
Parahydroxyben-zaldehyde (p-Hydroxybenzaldehyde) is a kind of important intermediate species, is widely used
In fields such as medicine, fragrance, pesticide and petrochemical industries.Medical aspect, parahydroxyben-zaldehyde can be used for synthesizing amoxycillin
(Amoxicillin), Trimethoprim trimethoprim (TMP), cardiovascular medicament Ai Siluo, to hydroxyglycine and people
Make the drugs such as Rhizoma Gastrodiae；In terms of fragrance, parahydroxyben-zaldehyde can be used for synthesis of vanillin, heliotropin, anisic aldehyde, syringaldehyde and
Many rare spices such as raspberry ketone；In terms of pesticide, parahydroxyben-zaldehyde can be used for synthesizing efficient herbicide Brominal and hydroxyl enemy
Oxalic acid dinitrile；In addition, parahydroxyben-zaldehyde can also be used to produce fungicide, food feed additive, nickel plating gloss agent and liquid crystal material
Expect the synthesis of precursor.
Currently, the industrial production of parahydroxyben-zaldehyde is mainly with diathesin, septichen, phenol, neighbour
Cresols is synthesized for raw material, is primarily present problems with：Cost is higher, yield is relatively low, environmental pollution is serious etc..
Invention content
The present invention is in order to avoid above-mentioned existing deficiencies in the technology, it is desirable to provide a kind of to be closed using microorganism
At the method for parahydroxyben-zaldehyde.The present invention is production bacterium with the fungal bacterial strain Gongronella sp.w5 of soil sources, from it
Extraction separation obtains parahydroxyben-zaldehyde in zymotic fluid.The Microbe synthesis method can carry out and have at normal temperatures and pressures
The advantages that green high-efficient.
The method that the present invention utilizes Microbe synthesis parahydroxyben-zaldehyde, includes the following steps：
Step 1：The preparation of Gongronella sp.w5 zymotic fluids
1a, actication of culture：Aseptically, a small bacterium is marked from bacterial strain Gongronella sp.w5 preservations inclined-plane
Block (1cm × 1cm) is inoculated on solid CPDA culture mediums, is cultivated 5 days in 28 DEG C of biochemical cultivation cases；
It is prepared by 1b, seed liquor：Aseptically, shovel marks four ferfas block (1cm from 1a cultured solid mediums
× 1cm) it is transferred in the 250mL triangular flasks equipped with VI fluid nutrient mediums of 100mL, 28 DEG C, carry out culture 4 in 120rpm shaking tables
It, the tunning of acquisition is as seed liquor；
1c, fermentation：The seed liquor homogenate that 1b is obtained is smashed, homogenate is inoculated into the ratio of 2.5% (V/V) and is equipped with
In the 1L triangular flasks of VI fluid nutrient mediums of 400mL, 37 DEG C, cultivate 3 days in 120rpm shaking tables, zymotic fluid 50L is collected；
Step 2：The preparation of Gongronella sp.w5 fermentation broth coarse extracts
The 50L zymotic fluids that step 1 is collected are extracted with isometric ethyl acetate, combining extraction liquid, and concentrated by rotary evaporation removes
Solvent obtains crude extract medicinal extract；
Step 3：The separation of crude extract
The crude extract medicinal extract that step 2 obtains being dissolved with methanol, 0.22 μm of membrane filtration, upper silicagel column carries out crude separation,
Component 2 is obtained after gradient elution；
Step 4：Component 2 isolates and purifies
The component 2 that step 3 is obtained crosses ODS reversed-phase columns, carries out gradient elution, obtains parahydroxyben-zaldehyde (w5-2).
In step 1, the solid CPDA culture mediums counted with 1L form it is as follows：(200g potatoes add 200g potatoes filter liquor
400mL distilled water boils 30min, filtering), 20g glucose, 3.0g potassium dihydrogen phosphates, 1.5g epsom salts, 0.04g dimension life
Plain B1And 15g agar powders obtain after 115 DEG C of 30min that sterilize after mixing.
In step 1, VI fluid nutrient medium counted with 1L form it is as follows：15g sucrose, 1.5g DL- asparagines, 1.0g
Potassium dihydrogen phosphate, 0.5g epsom salts, 0.1g disodium hydrogen phosphates, 0.01g calcium chloride, 0.01g ferrous sulfate heptahydrates,
2mg zinc sulfate, 2mg cupric sulfate pentahydrates, 0.05mg vitamin B1s and 28mg adenylates are after mixing in 115 DEG C of sterilizings
It is obtained after 30min.
In step 1, the bacterial strain Gongronella sp.w5 are to detach to obtain from soil, which has been preserved in China
Type Tissue Collection, address：Wuhan, China Wuhan University, preservation date：On December 30th, 2017, deposit number
CCTCC NO：M 2017787.
In step 3, the elution parameters of gradient elution are：
Four gradients are set, and eluent is respectively 100 according to volume ratio by dichloromethane and methanol:1、100:2、
100:4、100:8 are constituted, two column volumes of each gradient elution, are that a fraction is collected per 100mL, are examined by thin-layer chromatography
It surveys, same section merges, and obtains component 2.
The process of silicagel column progress crude separation specifically comprises the following steps in step 3：
3a, sample is mixed：Crude extract medicinal extract and silica gel (200-300 mesh) are pressed 1:2 ratio mix sample, after natural air drying,
It is for use to be ground into fine powdered；
3b, dress column：Claim the dry silica gel (200-300 mesh) of 10-50 times of applied sample amount, the dichloro for doing one times of silicone volume is added
Methane after being sufficiently stirred into homogenate with glass bar, pours into the glass column dried, loads onto and stores liquid ball, opens column lower piston, makes it
Natural subsidence will be stained with and gently rinse and (ensure that silica gel upper surface is smooth) in the silica gel initial wash agent on wall；
3c, compacting：After the completion of sedimentation, more dichloromethane are added, until (silica gel upper level does not exist the compacting of column bed
Decline)；
3d, loading：Excellent sample will be mixed above to be slowly added on the silicagel column of compacting, some dichloros are slowly added into along wall
Methane, then by a degreasing tampon to close to silica gel upper surface, Silica Surface is pounded hole when preventing continuous liquid；
3e, column and collection are crossed：Gradient elution (dichloromethane is carried out with dichloromethane and methyl alcohol mixed liquor：Methanol=100:
1、100:2、100:4、100:8), each gradient rushes two column volumes, is that a fraction is collected per 100mL, passes through thin-layer chromatography
It is detected, same section merges, and obtains component 2.
In step 4, the elution parameters of gradient elution are：
Two gradients are set, and eluent is respectively 3 according to volume ratio by first alcohol and water:7、4:6 are constituted, each gradient
Two column volumes are eluted successively, a fraction is collected per 100mL, collect obtain 10 fractions altogether, detected by thin-layer chromatography, phase
With partly merging (fraction 4 and fraction 5), low temperature concentration removes solvent, you can obtains parahydroxyben-zaldehyde (w5-2).
After compound w5-2 low temperature produced by the present invention is evaporated, deuterated methanol dissolving, using TMS as internal standard, AM- is added
400 type NMR spectrometer with superconducting magnet measure the nuclear-magnetism spectrum of compound w5-2, including：1H-NMR、13C-NMR、DEPT 135；Separately by first
The sample of alcohol dissolving carries out mass spectroscopy.
Compared with prior art, beneficial effects of the present invention are embodied in：
1, compared with chemical synthesis, entire reaction process carries out at normal temperatures and pressures, and pollution is small, energy consumption is small, and
And preparation method is simple, does not need aldehydes matter as raw material.
2, Gongronella sp.w5 bacterial strains full-length genome has been sequenced, and ensure that its safety, is given birth to for its industrially scalable
Theoretical foundation has been established in production.
3, the purity of target product is more than 98%.
Description of the drawings
Fig. 1 is that component 2 crosses the TLC figures after ODS reversed-phase columns.
Fig. 2 is the MS spectrograms of w5-2 prepared by the present invention.
Fig. 3 is the hydrogen nuclear magnetic resonance spectrogram of w5-2 prepared by the present invention.
Fig. 4 is the carbon-13 nmr spectra figure of the w5-4 of w5-2 prepared by the present invention.
Fig. 5 is the nuclear magnetic resonance DEPT135 carbon spectrograms of w5-2 prepared by the present invention.
Specific implementation mode
Technical solution of the present invention is further analyzed and described below by specific embodiment.
The present invention is as follows using the method for Microbe synthesis P-hydroxybenzoic acid：
1, the preparation of raw material
1a, bacterial strain Gongronella sp.w5 are to detach to obtain from soil, which has been preserved in Chinese Typical Representative culture
Collection, preservation date：On December 30th, 2017, deposit number CCTCC NO：M 2017787..
The preparation of 1b, solid CPDA culture mediums：By 20% potato filter liquor, 20g glucose, 3.0g potassium dihydrogen phosphates,
1.5g epsom salts, 0.04g vitamin B1s and 15g agar powders are uniformly mixed, and then sterilize in 115 DEG C 30min, spare.
The preparation of 1c, VI fluid nutrient medium：By 15g sucrose, 1.5g DL- asparagines, 1.0g potassium dihydrogen phosphates,
0.5g epsom salts, 0.1g disodium hydrogen phosphates, 0.01g calcium chloride, 0.01g ferrous sulfate heptahydrates, 2mg zinc sulfate,
2mg cupric sulfate pentahydrates, 0.05mg vitamin B1s and 28mg adenylates are uniformly mixed, and then sterilize in 115 DEG C 30min, spare.
2, the preparation of Gongronella sp.w5 zymotic fluids
1a, actication of culture：Aseptically, a small bacterium is marked from bacterial strain Gongronella sp.w5 preservations inclined-plane
Block (1cm × 1cm) is inoculated on solid CPDA culture mediums, is cultivated 5 days in 28 DEG C of biochemical cultivation cases；
It is prepared by 1b, seed liquor：Aseptically, shovel marks four ferfas block (1cm from 1a cultured solid mediums
× 1cm) it is transferred in the 250mL triangular flasks equipped with VI fluid nutrient mediums of 100mL, 28 DEG C, carry out culture 4 in 120rpm shaking tables
It, the tunning of acquisition is as seed liquor；
1c, fermentation：The seed liquor homogenate that 1b is obtained is smashed, homogenate is inoculated into the ratio of 2.5% (V/V) and is equipped with
In the 1L triangular flasks of VI fluid nutrient mediums of 400mL, 37 DEG C, cultivate 3 days in 120rpm shaking tables, zymotic fluid 50L is collected；
3, the preparation of Gongronella sp.w5 fermentation broth coarse extracts
The 50L zymotic fluids that step 2 is collected are extracted with isometric ethyl acetate, combining extraction liquid, and concentrated by rotary evaporation removes
Solvent obtains crude extract medicinal extract；
4, the separation of crude extract
The crude extract medicinal extract that step 3 obtains being dissolved with methanol, 0.22 μm of membrane filtration, upper silicagel column carries out crude separation,
Component 2 is obtained after gradient elution；
The process that silicagel column carries out crude separation specifically comprises the following steps：
4a, sample is mixed：Crude extract medicinal extract and silica gel (200-300 mesh) are pressed 1:2 ratio mix sample, after natural air drying,
It is for use to be ground into fine powdered；
4b, dress column：Claim the dry silica gel (200-300 mesh) of 10-50 times of applied sample amount, the dichloro for doing one times of silicone volume is added
Methane after being sufficiently stirred into homogenate with glass bar, pours into the glass column dried, loads onto and stores liquid ball, opens column lower piston, makes it
Natural subsidence will be stained with and gently rinse and (ensure that silica gel upper surface is smooth) in the silica gel initial wash agent on wall；
4c, compacting：After the completion of sedimentation, more dichloromethane are added, until (silica gel upper level does not exist the compacting of column bed
Decline)；
4d, loading：Excellent sample will be mixed above to be slowly added on the silicagel column of compacting, some dichloros are slowly added into along wall
Methane, then by a degreasing tampon to close to silica gel upper surface, Silica Surface is pounded hole when preventing continuous liquid；
4e, column and collection are crossed：Gradient elution (dichloromethane is carried out with dichloromethane and methyl alcohol mixed liquor：Methanol=100:
1、100:2、100:4、100:8), each gradient rushes two column volumes, is that a fraction is collected per 100mL, passes through thin-layer chromatography
It is detected, same section merges, and obtains component 2.
5, component 4 isolates and purifies
The component 2 that step 4 is obtained crosses ODS reversed-phase columns, carries out gradient elution, and the elution parameters of gradient elution are：
Two gradients are set, and eluent is respectively 3 according to volume ratio by first alcohol and water:7、4:6 are constituted, each gradient
Two column volumes are eluted successively, a fraction is collected per 100mL, collect obtain 10 fractions altogether, detected by thin-layer chromatography, phase
With partly merging (fraction 4 and fraction 5), low temperature concentration removes solvent, you can obtains parahydroxyben-zaldehyde (w5-2).
After compound w5-2 low temperature produced by the present invention is evaporated, deuterated methanol dissolving, using TMS as internal standard, AM- is added
400 type NMR spectrometer with superconducting magnet measure the nuclear-magnetism spectrum of compound w5-2, including：1H-NMR、13C-NMR、DEPT 135；Separately by first
The sample of alcohol dissolving carries out mass spectroscopy, and testing result is shown in Fig. 2-Fig. 5.By the nuclear-magnetism modal data and mass spectrometric data and document of measurement
It is compared, identifies that the compound is parahydroxyben-zaldehyde, structure is as follows：
The spectral data of compound w5-2：
C7H6O2, EI-MS m/z：121[M-H]-。
1H-NMR(400MHz,MeOD,δin ppm,J in Hz):9.68 (1H, s, CHO-1), 7.70 (2H, d, J=
8.6Hz, H-2,6), 6.86 (2H, d, J=8.6Hz, H-3,5), 5.15 (1H, s, OH-4).
13C-NMR(100MHz,MeOD,δin ppm):193.00(CHO),165.16(C-4),133.56(C-2,6),
130.25(C-1),116.95(C-3,5)。
Claims (9)
1. a kind of method using Microbe synthesis parahydroxyben-zaldehyde, it is characterised in that include the following steps：
Step 1：The preparation of Gongronella sp.w5 zymotic fluids
1a, actication of culture：Aseptically, fungus block inoculation is marked from bacterial strain Gongronella sp.w5 preservations inclined-plane
In on solid CPDA culture mediums, cultivated 5 days in 28 DEG C of biochemical cultivation cases；
It is prepared by 1b, seed liquor：Aseptically, shovel marks four ferfas blocks and is transferred to dress from 1a cultured solid mediums
In the 250mL triangular flasks for having VI fluid nutrient mediums of 100mL, 28 DEG C, culture 4 days, the fermentation production of acquisition are carried out in 120rpm shaking tables
Object is as seed liquor；
1c, fermentation：The seed liquor homogenate that 1b is obtained is smashed, homogenate is inoculated by 2.5% volume ratio equipped with VI liquid of 400mL
In the 1L triangular flasks of body culture medium, 37 DEG C, cultivate 3 days in 120rpm shaking tables, zymotic fluid 50L is collected；
Step 2：The preparation of Gongronella sp.w5 fermentation broth coarse extracts
The 50L zymotic fluids that step 1 is collected are extracted with isometric ethyl acetate, combining extraction liquid, and concentrated by rotary evaporation removes solvent,
Obtain crude extract medicinal extract；
Step 3：The separation of crude extract
The crude extract medicinal extract that step 2 obtains is dissolved with methanol, 0.22 μm of membrane filtration, upper silicagel column carries out crude separation, gradient
Component 2 is obtained after elution；
Step 4：Component 2 isolates and purifies
The component 2 that step 3 is obtained crosses ODS reversed-phase columns, carries out gradient elution, obtains parahydroxyben-zaldehyde.
2. according to the method described in claim 1, it is characterized in that：
In step 1, the solid CPDA culture mediums counted with 1L form it is as follows：200g potatoes filter liquor, 20g glucose, 3.0g phosphorus
Acid dihydride potassium, 1.5g epsom salts, 0.04g vitamin Bs1And 15g agar powders are after mixing in 115 DEG C of sterilizing 30min
After obtain.
3. according to the method described in claim 2, it is characterized in that：
The potato filter liquor is to filter to obtain after adding 400mL distilled water to boil 30min by 200g potatoes.
4. according to the method described in claim 1, it is characterized in that：
In step 1, VI fluid nutrient medium counted with 1L form it is as follows：15g sucrose, 1.5g DL- asparagines, 1.0g phosphoric acid
Potassium dihydrogen, 0.5g epsom salts, 0.1g disodium hydrogen phosphates, 0.01g calcium chloride, 0.01g ferrous sulfate heptahydrates, 2mg
Zinc sulfate, 2mg cupric sulfate pentahydrates, 0.05mg vitamin B1s and 28mg adenylates are after mixing after 115 DEG C of 30min that sterilize
It obtains.
5. according to the method described in claim 1, it is characterized in that：
In step 1, the bacterial strain Gongronella sp.w5 are to detach to obtain from soil, which has been preserved in Chinese Typical Representative
Culture collection, deposit number CCTCC NO：M 2017787.
6. according to the method described in claim 1, it is characterized in that：
In step 3, the elution parameters of gradient elution are：
Four gradients are set, and eluent is respectively 100 according to volume ratio by dichloromethane and methanol:1、100:2、100:4、
100:8 are constituted, two column volumes of each gradient elution, are that a fraction is collected per 100mL, are detected by thin-layer chromatography, identical
Part merges, and obtains component 2.
7. according to the method described in claim 1, it is characterized in that：
The process of silicagel column progress crude separation specifically comprises the following steps in step 3：
3a, sample is mixed：Crude extract medicinal extract and silica gel are pressed 1:2 ratio mix sample, after natural air drying, is ground into fine powdered and waits for
With；
3b, dress column：Claim the dry silica gel of 10-50 times of applied sample amount, the dichloromethane for doing one times of silicone volume is added, is filled with glass bar
After point stirring into homogenate, pour into the glass column dried, load onto and store liquid ball, open column lower piston, make its natural subsidence, will be stained in
Silica gel initial wash agent on wall gently rinses；
3c, compacting：After the completion of sedimentation, more dichloromethane are added, until column bed is compacted；
3d, loading：Excellent sample will be mixed above to be slowly added on the silicagel column of compacting, some dichloromethanes are slowly added into along wall
Alkane, then by a degreasing tampon to close to silica gel upper surface, Silica Surface is pounded hole when preventing continuous liquid；
3e, column and collection are crossed：Gradient elution is carried out with dichloromethane and methyl alcohol mixed liquor, each gradient rushes two column volumes, often
100mL is that a fraction is collected, and is detected by thin-layer chromatography, same section merges, and obtains component 2.
8. according to the method described in claim 7, it is characterized in that：
In step 3e, four gradients are set, the volume ratio of dichloromethane and methanol is respectively 100 when gradient elution:1、
100:2、100:4、100:8。
9. according to the method described in claim 1, it is characterized in that：
In step 4, the elution parameters of gradient elution are：
Two gradients are set, and eluent is respectively 3 according to volume ratio by first alcohol and water:7、4:6 are constituted, and each gradient is successively
Two column volumes are eluted, a fraction is collected per 100mL, collects obtain 10 fractions altogether, detected by thin-layer chromatography, identical portions
Divide and merge, low temperature concentration removes solvent, you can obtains parahydroxyben-zaldehyde.
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| CN109627153A (en) * | 2019-01-30 | 2019-04-16 | 桂林医学院 | A method of separating p-hydroxybenzaldehyde is extracted from Nostoc commune |
| CN108998480B (en) * | 2018-08-15 | 2020-03-27 | 遵义医学院 | Method for preparing phenol compounds by using microorganisms |
| CN114250254A (en) * | 2021-12-20 | 2022-03-29 | 宁夏清研高分子新材料有限公司 | Microbial synthesis method of p-hydroxybenzoic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114250254B (en) * | 2021-12-20 | 2024-01-05 | 宁夏清研高分子新材料有限公司 | Microorganism synthesis method of p-hydroxybenzoic acid |
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| CN108315361B (en) | 2021-04-13 |
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