CN107904267A - A kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde - Google Patents
A kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde Download PDFInfo
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- CN107904267A CN107904267A CN201711086192.2A CN201711086192A CN107904267A CN 107904267 A CN107904267 A CN 107904267A CN 201711086192 A CN201711086192 A CN 201711086192A CN 107904267 A CN107904267 A CN 107904267A
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Abstract
The present invention relates to a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the described method comprises the following steps：1) by suspension optical density OD600It is worth the Ganoderma Lucidum seed liquor for 0.15~0.25, is inoculated into the nutrient solution containing fleece-flower root water extract, under conditions of 24~30 DEG C, with the rotating speed of 150~200r/min, 30~40h of shaking table culture, obtains the zymotic fluid containing parahydroxyben-zaldehyde；2) after the zymotic fluid that step 1) obtains is extracted 2~4 times using extractant, then condensing crystallizing, parahydroxyben-zaldehyde crude product is obtained, crude product is dissolved using organic solvent, adds in gel chromatographic columns and is purified, up to parahydroxyben-zaldehyde.Present invention synthesis the efficient of parahydroxyben-zaldehyde, yield is high, purity is high, and easy to operate；Effectively reduce synthesis cost and time.
Description
Technical field
The present invention relates to a kind of preparation method of parahydroxyben-zaldehyde, and in particular to one kind is using microorganism conversion synthesis pair
The method of hydroxy benzaldehyde.
Background technology
Parahydroxyben-zaldehyde (p-HBA), molecular weight formula are C7H6O2, off-white color or light yellow crystal, have faint, order
The pleasant aromatic odor of people.Parahydroxyben-zaldehyde is a kind of important chemical industry and medicine intermediate, it can be used for developing a series of
Dyestuff, spices (such as anisaldehyde), medicine (such as Trimethoprim), pesticide (such as Brominal), liquid crystal, food fine chemistry industry production
Product；In addition parahydroxyben-zaldehyde can also be used as fungicide, photograph emulsifying agent and tin plating brightener etc..Since parahydroxyben-zaldehyde is wide
General purposes makes it, and at home and abroad supply falls short of demand in the market.
At present, the synthetic method of parahydroxyben-zaldehyde has chemical synthesis and microbe transformation method, wherein in it is most important
It is chemical synthesis.Common chemical synthesis has phynol method, para-nitrotoluene method, cresols Indirect Electrooxidation and paracresol
Method.Consider that chemical synthesis has complicated, poor selectivity, low output, production from synthesis parahydroxyben-zaldehyde synthetic degree of angle
The shortcomings of of high cost, difficult control of reaction conditions and environmental pollution,
And microbe transformation method have the advantages that operating condition it is gentle, it is environmentally protective have in material synthesis it is certain excellent
Gesture.The Microbe synthesis technology of parahydroxyben-zaldehyde is still in budding stage, the research in relation to parahydroxyben-zaldehyde biosynthesis
Report is few；Sachan in 2004 etc. is using p-Coumaric Acid as substrate, using paecilomyces bacterium as transformed bacteria, synthesizes para hydroxybenzene
Formaldehyde, but parahydroxyben-zaldehyde is an intermediate, has been finally converted into P-hydroxybenzoic acid.Wang Shengwen etc. uses p-
Putideks-0160 (FERMP-12879) strain, in the media such as sugar yeast containing sweet dew, controls 27 DEG C of temperature, pH6.8's turns
Paracresol is added after shaken cultivation 5d under the conditions of change, ferments to obtain parahydroxyben-zaldehyde through 3d.Can from only several reports
With find out parahydroxyben-zaldehyde in certain micro-organisms body it is unstable, can be further converted into hydroxyl under the action of relevant enzyme
Benzoic acid；And there is no the introduction of relevant bacteria species in the case of microorganism successful conversion parahydroxyben-zaldehyde, it is unfavorable for the method
Promotion and application, while the long low production efficiency of this method transformation time.And used mould is easily expanded to surrounding environment
Dissipate, there is the defects of pollution for easily leading to environment.
The content of the invention
It is an object of the invention to provide a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, micro- life
Thing conversion method comprises the following steps：
1) by suspension OD600It is worth the Ganoderma Lucidum seed liquor for 0.15~0.25, is inoculated into the culture containing fleece-flower root water extract
In liquid, under conditions of 24~30 DEG C, with the rotating speed of 150~200r/min, 30~40h of shaking table culture, obtains and contains to hydroxyl
The zymotic fluid of benzaldehyde；
2) after the zymotic fluid that step 1) obtains is extracted 2~4 times using extractant, then condensing crystallizing, obtain para hydroxybenzene first
Aldehyde crude product；The crude product is dissolved using organic solvent, adds in gel chromatographic columns and is purified, up to parahydroxyben-zaldehyde.
OD600It is worth the optical density for suspension.
The present invention is fermented using Ganoderma Lucidum as transformed bacteria with the nutrient solution containing fleece-flower root water extract active ingredient；
Shown by the research to its converted product, item yield in existing parahydroxyben-zaldehyde building-up process at this stage can be solved
The problem of low, environmental pollution is serious, synthesis precursor is single etc., breaks through traditional chemical synthesis mode, improves micro- life at this stage
Thing transformation technology, there is provided a kind of new synthesis thinking, improves parahydroxyben-zaldehyde combined coefficient and yield, simplifies procedures,
Save production cost.
Ganoderma Lucidum of the present invention is purchased from Guangdong Province's Culture Collection, numbering GIM5.250.
Present invention further propose that, the Ganoderma Lucidum seed liquor is 5%~6.8% to connect by nutrient solution volume percentage
Kind amount is seeded in nutrient solution.
Present invention further propose that, the Ganoderma Lucidum seed liquor is made in the following way：Ganoderma Lucidum is trained in solid
Support after being activated on base, be seeded in fluid nutrient medium, cultivate to suspension OD600It is worth for 0.15~0.25, it is spare.The present invention is into one
What step proposed, the fleece-flower root water extract is prepared in the following way：Take 6~6.5g Radix Polygoni Multifloris, add 4~5 times water decoct 2~
3 times, 25~35min is decocted every time, filtrate is filtered to take, adds water to be settled to 22~27mL, it is spare.
Preferably, 6.2~6.3g Radix Polygoni Multifloris are taken, add 4.5~4.8 times water decoct 2~3 times, every time decoct 28~
32min, filters to take filtrate, adds water to be settled to 25mL, spare.
Wherein, the water preferably uses deionization；The time of the decoction starts timing with slightly boiling.The present invention further carries
Go out, the nutrient solution includes the potato leaching powder of 5.5~6.5/L and the glucose of 16~24g/L.
The nutrient solution of Ganoderma Lucidum seed liquor is vaccinated with, its bottled amount is 10%~50%.
Present invention further propose that, the step 1) is specially：By suspension OD600It is worth the Ganoderma Lucidum seed liquor for 0.2,
It is seeded to by the inoculum concentration that nutrient solution volume percentage is 5%~6.8% in the nutrient solution containing fleece-flower root water extract, 26~
Under conditions of 30 DEG C, with the rotating speed of 160~200r/min, 36~40h of shaking table culture, obtains the fermentation containing parahydroxyben-zaldehyde
Liquid；
The Ganoderma Lucidum seed liquor and the volume ratio of the fleece-flower root water extract are 1:1.8~2.2, it is preferably 1:2.
The Ganoderma Lucidum seed liquor is after the 36h that ferments, and the synthetic quantity of parahydroxyben-zaldehyde reaches high value, suitable for step 2)
Purification processes.
Present invention further propose that, the extractant is ethyl acetate or n-butanol；Preferably ethyl acetate.
Present invention further propose that, the organic solvent is methanol or chloroform, is preferably methanol.
Wherein, every milliliter of organic solvent dissolving 0.4~0.5g parahydroxyben-zaldehyde crude product.
Present invention further propose that, the purification is purified using gel chromatographic columns, is specially：Advance methanol is molten
Gel powder after liquid immersion is added in gel column；Dissolved parahydroxyben-zaldehyde crude product solution is passed through 0.15~0.28 μm again
Filtering with microporous membrane after, add gel column in；The flow velocity of every 6 seconds one drops is controlled, TLC is collected and detects spotted position, subtract
Pressure is concentrated and dried, up to P-hydroxybenzoic acid.
The gel column is 30mm × 1000mm；The gel column activation,：Column is rinsed using the methanol of 3~4 times of column volumes
Son；
Wherein, test tube can be used to collect, collects a test tube within every 20 minutes；There is 41st pipe of the spot in collection in TLC detections
To the 51st pipe, merge the 41st~51 pipe.
TLC testing conditions：Solvent (isopropanol-absolute ethyl alcohol-ammonium hydroxide 7:2:1), ultraviolet colour developing；
The weight ratio of parahydroxyben-zaldehyde and gel powder is 1:18~22；
The miillpore filter is preferably 0.20~0.24 μm.
Preferred solution as the present invention, there is provided a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, institute
The method of stating comprises the following steps：
1) by suspension OD600It is worth the Ganoderma Lucidum seed liquor for 0.2, is 5%~6.8% to connect by nutrient solution volume percentage
Kind amount is seeded in the nutrient solution containing fleece-flower root water extract, under conditions of 26~30 DEG C, with turning for 160~200r/min
Speed, 36~40h of shaking table culture, obtains the zymotic fluid containing parahydroxyben-zaldehyde；
The Ganoderma Lucidum seed liquor and the volume ratio of the fleece-flower root water extract are 1:1.8~2.2；
2) zymotic fluid that step 1) obtains is adopted after being extracted with ethyl acetate 2~4 times, combined ethyl acetate layer, then concentrated
Crystallization, obtains parahydroxyben-zaldehyde crude product；
3) gel powder after advance methanol solution is soaked is added in gel column；Again by the dissolved para hydroxybenzene first of methanol
Aldehyde crude product solution is added in gel column after 0.20~0.24 μm of filtering with microporous membrane；The flow velocity of every 6 seconds one drops is controlled,
Collect TLC and detect spotted position, be concentrated under reduced pressure drying, up to parahydroxyben-zaldehyde.
The present invention uses Ganoderma Lucidum as transformed bacteria, it is fairly simple to fermentation medium components requirement, can effectively reduce hair
Ferment cost；
The present invention uses microbe transformation method, it synthesizes the efficient of parahydroxyben-zaldehyde, yield is high, purity is high, and
It is easy to operate；
The present invention uses Ganoderma Lucidum as transformed bacteria, its fermentation medium only needs potato leaching powder, glucose, fleece-flower root water to carry
Thing；The preparation of culture medium is simple, without adding other materials, can largely save fermentation costs, reduce at the same time
Medium component Optimization Steps, greatly save the time；Zymotic fluid is purified using gel chromatographic columns, is substantially increased to hydroxyl
The purity of benzaldehyde.The present invention provides a kind of quick, method for efficiently synthesizing parahydroxyben-zaldehyde.
Brief description of the drawings
Fig. 1 is the HPLC testing results of parahydroxyben-zaldehyde made from embodiment 1；
Parahydroxyben-zaldehyde is made for embodiment 1 in Fig. 21H-NMR；
Fig. 3 is parahydroxyben-zaldehyde made from embodiment 113C-NMR。
Embodiment
Following embodiments are used to illustrate the present invention, but are not limited to the scope of the present invention.
The reagent used in following embodiments is commercially available.
The culture liquid level potato glucose water, purchased from the BR (biochemical reagents) of Hai Bo Bioisystech Co., Ltd；
The ethyl acetate, methanol are purchased from Chinese medicines group；
Suspension OD600It is worth and is prepared with the following method for 0.2 Ganoderma Lucidum seed liquor：Ganoderma Lucidum is trained in PDA culture medium
After supporting 7 days, aseptically, it is inoculated into fluid nutrient medium, shaking table culture 2 days under the conditions of 28 DEG C, first order seed, knot is made
Ganoderma Lucidum suspension optical density OD during beam culture600Value reaches 0.2；
Embodiment 1
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, comprise the following steps：
1) by suspension OD600It is worth the Ganoderma Lucidum seed liquor for 0.2, is inoculated with by the inoculum concentration that nutrient solution volume percentage is 6%
To containing in fleece-flower root water extract nutrient solution, under conditions of 26~30 DEG C, with the rotating speed of 160~200r/min, shaking table culture
36h, obtains the zymotic fluid containing parahydroxyben-zaldehyde；
The Ganoderma Lucidum seed liquor and the volume ratio of the fleece-flower root water extract are 1:2；
2) zymotic fluid that step 1) obtains is adopted after being extracted with ethyl acetate 2~4 times, combined ethyl acetate layer, then concentrated
Crystallization, it is dissolving crystallized using methanol, obtain parahydroxyben-zaldehyde crude product；
3) gel powder after advance methanol solution is soaked is added in gel column；Again by the dissolved para hydroxybenzene first of methanol
Aldehyde crude product solution is added in gel column after 0.20~0.24 μm of filtering with microporous membrane；The flow velocity of every 6 seconds one drops is controlled,
Collect TLC and detect spotted position, be concentrated under reduced pressure drying, up to parahydroxyben-zaldehyde；
The dissolving 0.4g parahydroxyben-zaldehyde crude products wherein per ml methanol.
Embodiment 2
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the difference with embodiment 1
Only shaking table culture 30h.
Embodiment 3
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the difference with embodiment 1
Only shaking table culture 36h.
Embodiment 4
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the difference with embodiment 1
Only shaking table culture 40h.
Embodiment 2
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the difference with embodiment 1
Only shaking table culture 30h.
Embodiment 5
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the difference with embodiment 1
The volume ratio of only Ganoderma Lucidum seed liquor and the fleece-flower root water extract is 1:1.5.
Embodiment 6
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the difference with embodiment 1
The volume ratio of only Ganoderma Lucidum seed liquor and the fleece-flower root water extract is 1:2.5.
Embodiment 7
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the difference with embodiment 1
Only every milliliter of organic solvent dissolving 0.5g parahydroxyben-zaldehyde crude product.
Comparative example 1
The present embodiment provides a kind of method using microorganism conversion synthesis parahydroxyben-zaldehyde, the difference with embodiment 1
Only every milliliter of organic solvent dissolving 1g parahydroxyben-zaldehyde crude product.
Test example
1st, using product obtained by magnetic nuclear resonance method detection embodiment 1；
Nuclear Magnetic Resonance model：BRUKER AV-400 types nuclear magnetic resonance spectrometer (German Bruker companies)
As shown in Fig. 2, parahydroxyben-zaldehyde1H-NMR：
1H-NMR(CD3OD,600MHz)δ:10.58 (1H, s, OH), δ:9.78 (1H, s, CHO), 7.74 (2H, d, J=
9.0Hz, H-2,6), 6.91 (2H, d, J=9.0Hz, H-3,5)
As shown in figure 3, parahydroxyben-zaldehyde13C-NMR：
13C-NMR(CD3OD,150MHz)δ:130.3 (C-1), 133.2 (C-2,6), 116.9 (C-3,5), 162.8 (C-
4),192.7(CHO)
2nd, (the production of parahydroxyben-zaldehyde peak area percent made from above-described embodiment 1~6 is detected using HPLC detection methods
Rate) situation of change；
HPLC models：Agilent 1260infinity (Anjelen Sci. ＆ Tech. Inc)；
Chromatography column type number：Agilent 5HC-C18(250×4.6mm)；
HPLC testing conditions：0~50min, 10~80% (mobile phases：Acetonitrile-water), 15 μ L of flow velocity 1ml/min sample introductions, column
Temperature 25 DEG C, wavelength 210nm.
Testing result is as shown in table 1 below：
Table 1
From above-mentioned table, after shaking table culture to 36h, the yield of parahydroxyben-zaldehyde attains to a high place.
Although above the present invention is made to retouch in detail with general explanation, embodiment and experiment
State, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Scope.
Claims (10)
- A kind of 1. method using microorganism conversion synthesis parahydroxyben-zaldehyde, it is characterised in that comprise the following steps：1) by suspension OD600It is worth the Ganoderma Lucidum seed liquor for 0.15~0.25, is inoculated into the nutrient solution containing fleece-flower root water extract In, under conditions of 24~30 DEG C, with the rotating speed of 150~200r/min, 30~40h of shaking table culture, acquisition contains para hydroxybenzene The zymotic fluid of formaldehyde；2) after the zymotic fluid that step 1) obtains is extracted 2~4 times using extractant, then condensing crystallizing, it is thick to obtain parahydroxyben-zaldehyde Product；The crude product is dissolved using organic solvent, adds in gel chromatographic columns and is purified, up to parahydroxyben-zaldehyde.
- 2. according to the method described in claim 1, it is characterized in that, the Ganoderma Lucidum seed liquor is by nutrient solution volume percentage 5%~6.8% inoculum concentration is seeded in nutrient solution；The Ganoderma Lucidum seed liquor and the volume ratio of the fleece-flower root water extract are 1:1.5~2.5.
- 3. method according to claim 1 or 2, it is characterised in that the Ganoderma Lucidum seed liquor is made in the following way： After Ganoderma Lucidum is activated on solid medium, it is seeded in fluid nutrient medium, cultivates to suspension OD600It is worth for 0.15~0.25, It is spare.
- 4. according to any method of claims 1 to 3, it is characterised in that the fleece-flower root water extract is in the following way It is made：6~6.5g Radix Polygoni Multifloris are taken, adds 4~5 times of water to decoct 2~3 times, decocts 25~35min every time, filter to take filtrate, add water 22~27mL is settled to, it is spare.
- 5. according to any method of Claims 1 to 4, it is characterised in that the nutrient solution includes 5.5~6.5g/L's The glucose of potato leaching powder and 16~24g/L.
- 6. according to any method of Claims 1 to 5, it is characterised in that step 1) is specially：By suspension OD600It is worth and is 0.2 Ganoderma Lucidum seed liquor, is seeded to by the inoculum concentration that nutrient solution volume percentage is 5%~6.8% and is carried containing fleece-flower root water In the nutrient solution of thing, under conditions of 26~30 DEG C, with the rotating speed of 160~200r/min, 36~40h of shaking table culture, is contained There is the zymotic fluid of parahydroxyben-zaldehyde；The Ganoderma Lucidum seed liquor and the volume ratio of the fleece-flower root water extract are 1:1.8~2.2.
- 7. according to any method of claim 1~6, it is characterised in that the extractant is ethyl acetate or n-butanol.
- 8. according to any method of claim 1~7, it is characterised in that the organic solvent is methanol or chloroform；Preferably, every milliliter of organic solvent dissolving 0.4~0.5g parahydroxyben-zaldehyde crude product.
- 9. according to any method of claim 1~8, it is characterised in that the purification is specially：By advance methanol solution Gel powder after immersion is added in gel column；Again by dissolved parahydroxyben-zaldehyde crude product solution by 0.15~0.28 μm After filtering with microporous membrane, add in gel column；The flow velocity of every 6 seconds one drops is controlled, TLC is collected and detects spotted position, decompression It is concentrated and dried, up to P-hydroxybenzoic acid.
- 10. according to the method described in claim 1, it is characterised in that it includes following steps：1) by suspension OD600It is worth the Ganoderma Lucidum seed liquor for 0.2, by the inoculum concentration that nutrient solution volume percentage is 5%~6.8% It is seeded in the nutrient solution containing fleece-flower root water extract, under conditions of 26~30 DEG C, with the rotating speed of 160~200r/min, shakes Bed 36~40h of culture, obtains the zymotic fluid containing parahydroxyben-zaldehyde；The Ganoderma Lucidum seed liquor and the volume ratio of the fleece-flower root water extract are 1:1.8~2.2；2) zymotic fluid that step 1) obtains is adopted after being extracted with ethyl acetate 2~4 times, combined ethyl acetate layer, then condensing crystallizing, It is dissolving crystallized using methanol, obtain parahydroxyben-zaldehyde crude product；3) gel powder after advance methanol solution is soaked is added in gel column；It is again that the dissolved parahydroxyben-zaldehyde of methanol is thick Product solution is added in gel column after 0.20~0.24 μm of filtering with microporous membrane；The flow velocity of every 6 seconds one drops is controlled, is collected TLC detects spotted position, and be concentrated under reduced pressure drying, up to parahydroxyben-zaldehyde.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108315361A (en) * | 2018-04-20 | 2018-07-24 | 安徽大学 | Method for synthesizing p-hydroxybenzaldehyde by using microorganisms |
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| WO2008150899A1 (en) * | 2007-05-29 | 2008-12-11 | Emory University | Combination therapies for treatment of cancer and inflammatory diseases |
| CN104894180A (en) * | 2015-05-25 | 2015-09-09 | 浙江大学 | Method for preparing aglycone by transforming soybean isoflavone glycoside through lucid ganoderma fermentation |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108315361A (en) * | 2018-04-20 | 2018-07-24 | 安徽大学 | Method for synthesizing p-hydroxybenzaldehyde by using microorganisms |
| CN108315361B (en) * | 2018-04-20 | 2021-04-13 | 安徽大学 | Method for synthesizing p-hydroxybenzaldehyde by using microorganisms |
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