CN105002238A - Naringin hydroxyl protective reaction method based on Pseudomonas stutzeri cell catalysis - Google Patents
Naringin hydroxyl protective reaction method based on Pseudomonas stutzeri cell catalysis Download PDFInfo
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- CN105002238A CN105002238A CN201510448169.8A CN201510448169A CN105002238A CN 105002238 A CN105002238 A CN 105002238A CN 201510448169 A CN201510448169 A CN 201510448169A CN 105002238 A CN105002238 A CN 105002238A
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Abstract
The invention discloses a naringin hydroxyl protective reaction method based on Pseudomonas stutzeri cell catalysis. The method includes the following steps: organic solvents, naringin, acylation substrates and Pseudomonas stutzeri cell catalysts are respectively added into a 10-ml triangular flask with a plug and evenly mixed, and the flask is placed into a water bath constant temperature oscillator for carrying out reaction. Under the optimal reaction condition determined by the research, the maximum productive rate of naringin acylation reactions is promoted by Pseudomonas stutzeri cells to be 70.8%. Influences of the reaction conditions on the regioselectivity of the Pseudomonas stutzeri cells in the naringin acylation reactions are not large, and the 6''-regioselectivity is kept 99% or more.
Description
Technical field
The invention belongs to biocatalysis and biological medicine synthesis and control field, be specifically related to a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis.
Background technology
Flavonoid compound is that two phenyl ring are interconnected by three carbon atoms and a series of important polyphenolic compound formed, and is extensively present in nearly all plant, especially vegetables and fruit; Medicine, foods and cosmetics there is very large using value.Flavones has multiple biological activity to comprise anti-oxidant activity, anti-inflammatory, anticancer, antibacterial, antianaphylaxis and antiviral etc., but due to its polyhydroxy structure, most of flavones biological activity is limited to that it is low fat-soluble or water-soluble.Be positioned at the biological and chemical activity of the hydroxyl on phenyl ring or glycoside skeleton on flavones and have important impact.The esterification of flavones is considered to the very promising method of one, can be used for the solubleness improving flavones, thus make flavones show more physiologically active.There are some researches show, modifying flavonoid compound structure not only can improve physico-chemical properties selectively, e.g., and thermostability and fat-soluble; And its biological activity can be strengthened, as anti-oxidant activity, anti-microbial activity, Premeabilisation of cells ability, fat-reducing and hypolipemic function.
Naringin is the one in flavonoid glycoside, and pharmaceutically have reduction cholesterol, the effects such as anti-inflammatory hemostasis, also can add in food as antioxidant.Naringin has 8 hydroxyls, is distributed on phenyl ring or sugared ring.Not only hydroxyl on ring has important impact to its activity, therefore optionally carries out esterification to the hydroxyl of naringin and has great importance, and can keep its activity but also can improve it fat-solublely increases otherwise activity.
Summary of the invention
The present invention utilizes traditional chemical process to be usually difficult to protect specific hydroxyl, and the object of the invention is to develop a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis.Pseudomonas stutzeri cell is urged the suitableeest organic solvent of naringin hydrate acylation reaction, acry radical donor, acry radical donor and naringin hydrate mol ratio, initial moisture content, Pseudomonas stutzeri cell catalyst, temperature of reaction and hunting speed and is respectively tertiary amyl alcohol, propionate (VP), 20:1,0%(v/v), 40mg/mL, 40 DEG C and 180rpm, after reaction 24h, productive rate can reach 70.8%.Reaction conditions is little on the regioselectivity impact of Pseudomonas stutzeri cell in the propionating reaction of naringin, and 6 ' '-regioselectivity remains on more than 99%.
The method catalyst preparing is simple to operation, and reaction conditions is gentle, and productive rate is high, and initial velocity is fast, and hydroxyl protection regioselectivity can control, and the selectivity overcoming traditional chemical routes is low and cause substrate utilization ratio low, and product purity is low, easily generates the shortcomings such as by product.
The present invention is achieved through the following technical solutions:
Based on a naringin hydroxyl protection reaction method for Pseudomonas stutzeri cell catalysis, comprise the following steps:
1) Pseudomonas stutzeri cell catalyst is made: bacterium seed liquor be seeded to containing producing in the liquid nutrient medium of enzyme inducer, inoculum size is 0.5% ~ 20%(v/v), culture condition is 30 DEG C ~ 50 DEG C, and incubation time is 12 ~ 144h; Collected after centrifugation thalline, distilled water wash twice, through vacuum lyophilization 12h-36h, results thalline dry powder, is bacterial cell catalyzer;
2) in band plug triangular flask, organic solvent is added;
3) flavonoid compound is added;
4) acry radical donor is added;
5) in organic solvent reaction system, add 0 ~ 160 μ L water;
6) adding Pseudomonas stutzeri cell catalyst makes whole reaction system final quality be 20 ~ 160mg, mixes;
7) be placed in water-bath constant temperature oscillator reaction, speed is 100 ~ 260rpm.
Further, can appropriate change step 2) volume of described band plug triangular flask zooms in or out reaction system volume;
Step 2) described band plug triangular flask volume is 10mL; Described organic solvent is single kind organic solvent or mixed organic solvents, and wherein single kind organic solvent is the trimethyl carbinol or tertiary amyl alcohol, and mixed organic solvents is acetonitrile-tertiary amyl alcohol, pyridine-tertiary amyl alcohol etc.; The volume of organic solvent is 2mL;
Flavonoid compound described in step 3) is naringin or bark of ash first hydrate, and its consumption is 10mmol-90mmol;
The propionate of to be consumption be 60 ~ 2400 mmol of acry radical donor described in step 4);
Water that step 5) uses is ultrapure water or distilled water;
Method for controlling reaction temperature described in step 7) is the device water-bath of shaking bath isothermal vibration or constant temperature shaking flask cabinet gas bath etc., and temperature of reaction is 25 DEG C ~ 60 DEG C.
Further optimally, said method comprising the steps of:
1) Pseudomonas stutzeri cell catalyst is made;
2) in 10mL band plug triangular flask, add 2mL organic solvent, can be pure organic solvent or mixed organic solvents;
3) naringin hydrate is added;
4) add acry radical donor propionate, consumption is respectively 60 ~ 2400 mmol;
5) in 2mL tertiary amyl alcohol reaction system, 0-160 μ L water is added;
6) in 2mL tertiary amyl alcohol reaction system, adding Pseudomonas stutzeri cell catalyst makes whole reaction system final quality be 20 ~ 160mg;
7) during naringin hydroxyl protection, temperature of reaction is 25 DEG C ~ 60 DEG C, reacts in water-bath constant temperature oscillator;
8) in water-bath constant temperature oscillator oscillatory reaction, concussion speed is 100 ~ 260rpm.
Step 2) in react the triangular flask volume that uses and be not limited to 10mL, reaction system can suitably zoom in or out; Organic solvent be single kind organic solvent as pyridine or mixed organic solvents, as acetonitrile-tertiary amyl alcohol, the trimethyl carbinol-pyridine, tertiary amyl alcohol-pyridine; Best mixed organic solvents is tertiary amyl alcohol, but is not limited thereto solvent;
In step 5) use water for ultrapure water or distilled water;
Step 8) isothermal vibration device is not limited to shaking bath, as the gas bath conditions such as constant temperature shaking flask cabinet also can.
The present invention has following advantage compared with prior art:
1, utilize biological catalyst Pseudomonas stutzeri cell as catalyzer, environmental friendliness gentle than chemical catalyst reaction conditions; Low than enzyme catalyst cost.
2, in the method, catalyst preparing is simple to operation, and acry radical donor propionate is conventional easily to be bought, and initial velocity of reaction is fast; productive rate is high, and regioselectivity is high, and the low substrate utilization ratio that causes of the selectivity overcoming traditional chemical routes is low; product purity is low, easily generates the shortcomings such as by product.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, but enforcement of the present invention and protection domain are not limited thereto.
embodiment 1
2mL pyridine, 60 mmol naringin hydrates, 1200mmol propionate and 80mg Pseudomonas stutzeri cell catalyst is all added in 10mL band plug triangular flask, mix, be placed in water-bath constant temperature oscillator reaction (40 DEG C, 180r/min), timing sampling 20 μ L, dilutes 50 times with 60% (volume fraction, lower same) methanol-water mixing solutions, mix rear centrifugal (15,000r/min) 15min, automatic sampler gets supernatant liquor 20 μ L, for efficient liquid phase chromatographic analysis.In pure tertiary amyl alcohol, Pseudomonas stutzeri cell can catalysis naringin generation acylation reaction, and after 24h, productive rate is respectively 70.8%, 6 ' ' regioselectivity is respectively 99.5%.
Spawn culture method: slant medium, nutrient broth medium; Seed liquor is inoculated in fermention medium after cultivating 24h, and inoculum size is 2%(v/v), 180r/m, cultivates 48h by 30 DEG C.Seed liquor substratum (w/v) is 1% glucose, 1% extractum carnis, 1% peptone, 0.5% K
2hPO
4, 0.02% MgSO
47H
2o, 0.5%NaCl, pH 7.0 ± 0.1; Fermention medium (w/v) is 0.5% soybean oil, 0.1% yeast extract, 0.5% (NH
4)
2sO
4, 0.1% K
2hPO
4, 0.02% MgSO
47H
2o.
embodiment 2
In 3 10mL band plug triangular flasks, 60 mmol naringin hydrates, 1200mmol propionate are mixed with 2mL organic solvent (tetrahydrofuran (THF), the trimethyl carbinol, tertiary amyl alcohol) respectively, add 80mg Pseudomonas stutzeri cell catalyst, mix, be placed in water-bath constant temperature oscillator reaction (40 DEG C, 180r/min), timing sampling 10 μ L, 100 times are diluted with 40% methanol-water mixing solutions, mix rear centrifugal (15,000r/min) 15min, automatic sampler gets supernatant liquor 20 μ L, for efficient liquid phase chromatographic analysis.Reaction result is as table 1.
Table 1 different organic solvents urgees the impact of the propionating reaction of naringin to Pseudomonas stutzeri cell
| logP | Transformation efficiency/% | Regioselectivity/% | |
| Tetrahydrofuran (THF) | 0.49 | 21.7±0.12 | 99.5±0.04 |
| The trimethyl carbinol | O.80 | 61.8±0.20 | 99.3±0.03 |
| Virahol | 1.9 | 10.4±0.02 | 99.3±0.02 |
In table, reaction conditions: 2mL organic solvent, 80mg Pseudomonas stutzeri cell catalyst, 60 mmol naringin hydrates, 1200 mmol propionate, 40 DEG C, 180 rpm, reaction 24h.
embodiment 3
2mL tertiary amyl alcohol is all added in 8 10mL band plug triangular flasks, naringin (the 10mmol of different amounts is added again respectively in 8 band plug triangular flasks, 20mmol, 40mmol, 50mmol, 60mmol, 70mmol, 80mmol, 90mmol), 1200mmol propionate and 80mg Pseudomonas stutzeri cell catalyst is all added in the most backward each band plug triangular flask, mix, be placed in water-bath constant temperature oscillator reaction (40 DEG C, 180r/min), timing sampling 20 μ L, 50 times are diluted with 60% methanol-water mixing solutions, mix rear centrifugal (15, 000 r/min) 15min, automatic sampler gets supernatant liquor 20 μ L, for efficient liquid phase chromatographic analysis.Reaction result shows, when naringin concentration is lower (5 ~ 25mmol/L), increase the amount of substrate, speed of response significantly increases; Continue the concentration increasing naringin, speed of response increase is tending towards slow; In the concentration range of the effects, speed of response is not yet urged in steady state value, and the whole-cell catalyst input amount can knowing 40 mg/mL by inference is unsaturated by substrate yet in reaction system.But along with the increase (>30mmol/L) of naringin concentration, reaction yield is slow downtrending, regioselectivity change maintains 99%.
embodiment 4
2mL 50%(v/v is all added in 8 10mL band plug triangular flasks) octane-iso-pyridine mixed organic solvents, 60mmol naringin and 1200mmol/L propionate, different mass Pseudomonas stutzeri cell catalyst (10mg is added respectively again in 8 band plug triangular flasks, 20mg, 30mg, 40mg, 50mg, 60mg, 70mg, 80mg), mix, be placed in water-bath constant temperature oscillator reaction (30 DEG C, 140r/min), timing sampling 20 μ l, 50 times are diluted with 60% methanol-water mixing solutions, mix rear centrifugal (15, 000 r/min) 15min, automatic sampler gets supernatant liquor 20 μ L, for efficient liquid phase chromatographic analysis.Reaction result shows, in the propionating reaction of naringin, Pseudomonas stutzeri cell catalyst consumption is greater than 20 mg/mL(using 50%(v/v) octane-iso-pyridine is as solvent) time productive rate tend to be steady, and productive rate reaches maximum value 65% when consumption is 20 mg/mL; In propionating reaction, when Pseudomonas stutzeri cell catalyst consumption is greater than 40 mg/mL, continue to increase Pseudomonas stutzeri cell catalyst consumption, productive rate almost no longer improves, and maximum value is 85.6%; And regioselectivity change is little, all the time more than 99%.
embodiment 5
2mL tertiary amyl alcohol and 60mmol naringin is all added in 9 10mL band plug triangular flasks, different volumetric molar concentration propionate (60 mmol are added respectively again in 9 band plug triangular flasks, 300 mmol, 600mmol, 900 mmol, 1200 mmol, 1500 mmol, 1800 mmol, 2100 mmol, 2400 mmol), 80mg Pseudomonas stutzeri cell catalyst is all added in the most backward each band plug triangular flask, mix, be placed in water-bath constant temperature oscillator reaction (40 DEG C, 180r/min), timing sampling 20 μ l, 100 times are diluted with 40% methanol-water mixing solutions, mix rear centrifugal (15, 000 r/min) 15min, automatic sampler gets supernatant liquor 20 μ l, for efficient liquid phase chromatographic analysis.Reaction result shows; the initial velocity that full cell urgees the propionating reaction of naringin all increases along with the increase of propionate and naringin mol ratio (1:1-20:1), then increases mol ratio, and productive rate change is little; but 6 ' '-regioselectivity change is little, all the time higher than 99%.
Consider, think that the optimum proportion that full cell urgees propionate and naringin hydrate mol ratio in naringin hydrate acetylization reaction is 20:1.
embodiment 6
2mL tertiary amyl alcohol is all added in 9 10mL band plug triangular flasks, 60mmol naringin and propionate 1200 mmol, ultrapure water (the 0 μ L of different volumes is added again respectively in 9 band plug triangular flasks, 20 μ L, 40 μ L, 60 μ L, 80 μ L, 100 μ L, 120 μ L, 140 μ L, 160 μ L), 40mg Pseudomonas stutzeri cell catalyst is added in the most backward each band plug triangular flask, mix, be placed in water-bath constant temperature oscillator reaction (40 DEG C, 180r/min), timing sampling 20 μ L, 50 times are diluted with 60% methanol-water mixing solutions, mix rear centrifugal (15, 000 r/min) 15min, automatic sampler gets supernatant liquor 20 μ L, for efficient liquid phase chromatographic analysis.Reaction result shows; when adding ultrapure water and being little; the initial velocity of acylation reaction and productive rate reduce with the increase adding volume; the increase change reached again with moisture content after certain value is little; regioselectivity is substantially constant; all the time more than 99%, therefore think that the volume of the ultrapure water added in reaction system is advisable with 0%.
embodiment 7
2mL tertiary amyl alcohol is all added in 8 10mL band plug triangular flasks, 0 μ L ultrapure water, 60mmol naringin, propionate 1200 mmol and 40mg Pseudomonas stutzeri cell catalyst, mix, be placed in differing temps (25 DEG C, 30 DEG C, 35 DEG C, 40 DEG C, 45 DEG C, 50 DEG C, 55 DEG C, 60 DEG C) under water-bath constant temperature oscillator reaction (180r/min), timing sampling 20 μ L, 50 times are diluted with 60% methanol-water mixing solutions, mix rear centrifugal (15, 000 r/min) 15min, automatic sampler gets supernatant liquor 20 μ L, for efficient liquid phase chromatographic analysis.Reaction result shows, in 25 ~ 40 DEG C of temperature ranges, along with the rising of temperature of reaction, the initial velocity that the full cell of Pseudomonas stutzeri urgees the propionating reaction of naringin increases all thereupon.But compared with initial velocity, the productive rate of reaction shows the trend of typically falling after rising.Optimum temperuture is 40 DEG C-55 DEG C, and now, productive rate is at 70.8%-74.3%, and after temperature is higher than 55 DEG C, productive rate declines obviously, 6 ' ' impact of-regioselectivity is little, is all greater than 99%.
Claims (9)
1., based on a naringin hydroxyl protection reaction method for Pseudomonas stutzeri cell catalysis, it is characterized in that, comprise the following steps:
1) Pseudomonas stutzeri cell catalyst is made;
2) in band plug triangular flask, organic solvent is added;
3) flavonoid compound is added;
4) add acry radical donor, form organic solvent reaction system;
5) in organic solvent reaction system, add 0 ~ 160 μ L water;
6) adding Pseudomonas stutzeri cell catalyst makes whole reaction system final quality be 20 ~ 160mg, mixes;
7) be placed in water-bath constant temperature oscillator reaction, concussion speed is 100 ~ 260rpm.
2. a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis according to claim 1, is characterized in that step 2) described band plug triangular flask volume is 10mL.
3. a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis according to claim 1; it is characterized in that step 2) described organic solvent is single kind organic solvent or mixed organic solvents; wherein single kind organic solvent is the trimethyl carbinol or tertiary amyl alcohol, and mixed organic solvents is acetonitrile-tertiary amyl alcohol, pyridine-tertiary amyl alcohol etc.
4. a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis according to claim 1, is characterized in that step 2) volume of described organic solvent is 2mL.
5. a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis according to claim 1, it is characterized in that flavonoid hydrate described in step 3) is naringin hydrate, naringin consumption is 10mmol-90mmol.
6. a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis according to claim 1, is characterized in that acry radical donor consumption described in step 4) is the propionate of 60 ~ 2400 mmol.
7., according to a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis described in claim 1, it is characterized in that water that step 5) uses is for ultrapure water or distilled water.
8., according to a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis described in claim 1, it is characterized in that method for controlling reaction temperature is the device water-bath of shaking bath isothermal vibration or constant temperature shaking flask cabinet gas bath etc.
9. a kind of naringin hydroxyl protection reaction method based on Pseudomonas stutzeri cell catalysis according to claim 1, is characterized in that temperature of reaction described in step 7) is 25 DEG C ~ 60 DEG C.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018218903A1 (en) * | 2017-05-27 | 2018-12-06 | 华南理工大学 | Method for preparing troxerutin ester using whole cell catalysis |
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|---|---|---|---|---|
| CN102851337A (en) * | 2012-08-31 | 2013-01-02 | 华南理工大学 | Method for realizing protective reaction for hydroxyl groups of cytidine compound through catalysis of Aspergillus oryzae cells |
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Patent Citations (2)
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| CN102851337A (en) * | 2012-08-31 | 2013-01-02 | 华南理工大学 | Method for realizing protective reaction for hydroxyl groups of cytidine compound through catalysis of Aspergillus oryzae cells |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018218903A1 (en) * | 2017-05-27 | 2018-12-06 | 华南理工大学 | Method for preparing troxerutin ester using whole cell catalysis |
| US11286511B2 (en) | 2017-05-27 | 2022-03-29 | South China University Of Technology | Method for preparing troxerutin ester using whole-cell catalysis |
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Application publication date: 20151028 |