CN106755149A - A kind of method that utilization lipase prepares hydroxytyrosol DHA ester - Google Patents
A kind of method that utilization lipase prepares hydroxytyrosol DHA ester Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
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Abstract
A kind of method that utilization lipase prepares hydroxytyrosol DHA ester, including step：To methyl tertiary butyl ether(MTBE) is added in hydroxytyrosol, take DHA and be added in hydroxytyrosol solution, take lipase and be added in alkyd mixed solution, seal inflated with nitrogen, after oscillating reactions, frozen water cooling is filtered to remove lipase, rotary evaporation, removes methyl tertiary butyl ether(MTBE), obtains crude product；Crude product is dissolved in ethanol, adds sodium carbonate, water, nitrogen to protect, and flow back saponification, the saponification solution n-hexane extraction of gained, and then rotary evaporation, obtains hydroxytyrosol DHA ester.Hydroxytyrosol and DHA reaction are prepared hydroxytyrosol ester by the present invention under the catalysis of enzyme, and obtained product can strengthen hydroxytyrosol into cell and the ability of tissue, improve its half-life period；Meanwhile, DHA has the functions such as suppression inflammation, reduction blood fat, enhancing memory and thinking ability.
Description
Technical field
The present invention relates to the preparation of hydroxytyrosol derivatives, hydroxyl is prepared using lipase more specifically to one kind
The method of tyrosol-DHA ester.
Background technology
Hydroxytyrosol (Hydroxytyrosol) is a kind of natural polyphenol class compound, is mainly derived from olive oil and adds
In the waste water that work olive oil is produced.Correlative study shows that hydroxytyrosol is a kind of important bioactivator, is had perhaps to human body
More healthy and beneficial effect, such as increases human body HDL-C (HDL-C), reduces the damage of human body lipid oxidation, suppresses
Inflammation, lifting endothelial function, reduction systolic pressure, suppression growth and metastasis of tumours, protection nervous centralis etc..
Although hydroxytyrosol has many healthy and beneficial effects to human body, and absorbs preferable in enteron aisle, in fact its life
Thing availability is relatively low.Hydroxytyrosol is very fast in enterocyte and liver cell intracellular metabolite, generates minimal amount of metabolin, and produces
Metabolin blood and tissue in concentration it is very low.
The content of the invention
It is an object of the invention to synthesis of hydroxy tyrosol derivative --- hydroxytyrosol-DHA ester, can be with
Enhancing hydroxytyrosol enters the ability of cell and tissue, improves its half-life period；Ensure that synthesising method reacting condition is gentle simultaneously, make
Standby and purge process is simple, end-product purity is high.
In order to achieve the above object, the present invention provides one kind and prepares hydroxytyrosol-DHA using lipase
The method of ester, comprises the following steps：
S1, to methyl tertiary butyl ether(MTBE) is added in hydroxytyrosol, ultrasound is fully mixed, and obtains hydroxytyrosol solution, the hydroxyl
Base tyrosol is 1 with methyl tertiary butyl ether(MTBE) molal volume ratio:25~50 (mol/L)；
S2, take DHA (DHA) and be added in the hydroxytyrosol solution obtained by step S1, ultrasound is fully mixed
It is even, obtain alkyd mixed solution；The DHA is 6~12 with hydroxytyrosol mol ratio:1；
S3, take lipase EC 3.1.1.3 and be added in the alkyd mixed solution obtained by step S2, seal inflated with nitrogen, obtain
Lipase solution；The lipase EC 3.1.1.3 >=5000U/g, the lipase EC3.1.1.3 and hydroxytyrosol mass body
Product is than being 30~60:1(g/mol)；
Under preferred embodiment, the lipase EC 3.1.1.3 are Novozyme-435, from antarctic candida.
S4, by the lipase solution obtained by step S3, be placed in 35~50 DEG C, oscillating reactions 24 under 100~200rpm environment
After~72h, taking-up is placed in ice-water bath and cools down, and obtains enzyme reaction solution；
S5, by the enzyme reaction solution filtration treatment obtained by step S4, lipase is removed, then at 35~45 DEG C, relative vacuum
Rotary evaporation under the conditions of -0.05~-0.08Mpa of degree, removes methyl tertiary butyl ether(MTBE), obtains crude product；
S6, by step S5 gained crude product be dissolved in the ethanol that volumetric concentration is 95%, add sodium carbonate, water, nitrogen
Protection, flow back 20~30min of saponification at 40~50 DEG C, obtains saponification solution；The crude product and the ethanol that volumetric concentration is 95%
Mass volume ratio is 1:10~20 (g/mL), the crude product is 1 with sodium carbonate mass ratio:0.8~1.2, the crude product with
Water quality volume ratio is 1:4~6 (g/mL)；
S7, by the n-hexane extraction 1~3 time of the saponification solution obtained by step S6, the n-hexane layer anhydrous slufuric acid for obtaining
Sodium is removed water, then the rotary evaporation under the conditions of 35~45 DEG C, relative degree of vacuum -0.05~-0.08Mpa, removes n-hexane, is obtained
Hydroxytyrosol-DHA ester；The volume of extraction n-hexane used is with volumetric concentration used in step S6 every time
The ratio of the volume of 95% ethanol is 2~6:1.
Technological innovation of the invention is：
1st, reaction condition of the present invention is gentle, and product esterification yield is high, and the hydroxytyrosol-DHA ester of preparation need not be using post layer
The methods such as analysis purifying, the purity of end-product is high.
2nd, hydroxytyrosol and DHA (DHA) reaction are prepared hydroxytyrosol by the present invention under the catalysis of enzyme
Ester, obtained product can strengthen hydroxytyrosol into cell and the ability of tissue, improve its half-life period；Meanwhile, DHA has suppression
The functions such as inflammation processed, reduction blood fat, enhancing memory and thinking ability.
3rd, the present invention can simultaneously play hydroxytyrosol and DHA in healthy and beneficial side by the hydroxytyrosol-DHA ester for synthesizing
The effect in face.
Specific embodiment
Following non-limiting examples can make one of ordinary skill in the art be more fully understood the present invention, but not with
Any mode limits the present invention.
Embodiment 1
S1,0.1mol hydroxytyrosols are taken, be slowly added to methyl tertiary butyl ether(MTBE), hydroxytyrosol:Methyl tertiary butyl ether(MTBE) is 1:25
(mol/L), ultrasound is fully mixed；
S2, take during 0.6mol DHA add S1 resulting solutions, then fully mixed by ultrasonic；
S3, take lipase (Novozyme-435, from antarctic candida, EC 3.1.1.3) add S2 resulting solutions
In, enzyme:Hydroxytyrosol is controlled 30:1 (g/mol), then to glass container nitrogen charging hermetic seal；
S4, glass container is placed in constant temperature oscillator and is reacted, reaction temperature is 40 DEG C, hunting speed is
100rpm, the reaction time is 48h.After the completion of reaction, taking-up is placed in ice-water bath and cools down；
S5, by the solution filtration treatment obtained by S4, lipase is removed, then at 35 DEG C of temperature, relative degree of vacuum -0.08Mpa
Under the conditions of rotary evaporation, remove methyl tertiary butyl ether(MTBE), obtain crude product；
S6, by S5 gained crude product be dissolved in the ethanol that volumetric concentration is 95%, crude product:95% ethanol is controlled 1:15
(g/mL)；Add sodium carbonate, the quality of crude product:The quality control of sodium carbonate is 1:0.8(g/g)；Add water, the matter of crude product
Amount:The fixing fabric structure of water is 1:5 (g/mL), by above-mentioned reactant mixture under nitrogen stream protection, in 40 DEG C of reaction temperatures, backflow
Saponification 30min；
S7, by S6 gained mixtures, be transferred in separatory funnel, with n-hexane extraction 2 times, each extraction n-hexane
Volume:The fixing fabric structure of 95% ethanol is 6 in S5:1 (mL/mL), the n-hexane layer anhydrous sodium sulfate water removal for obtaining, Ran Houyu
Rotary evaporation under the conditions of 35 DEG C of temperature, relative degree of vacuum -0.08Mpa, removes n-hexane, obtains hydroxytyrosol-DHA ester, its matter
It is 19.1833g to measure.
By above-mentioned steps, the esterification yield of hydroxytyrosol is 41.3%.Using HPLC-UV (efficient liquid phases-ultraviolet detection
Device) detection, hydroxytyrosol-DHA ester, purity is 86.4%.
Embodiment 2
S1,0.1mol hydroxytyrosols are taken in sealable glass container, be slowly added to methyl tertiary butyl ether(MTBE), hydroxyl junket
Alcohol:Methyl tertiary butyl ether(MTBE) is controlled 1:50 (mol/L), are then fully mixed by ultrasonic；
S2, take during 1.2mol DHA add S1 resulting solutions, then fully mixed by ultrasonic；
S3, take lipase (Novozyme-435, from antarctic candida, EC 3.1.1.3) add S2 resulting solutions
In, enzyme:Hydroxytyrosol is controlled 50:1 (g/mol), then to glass container nitrogen charging hermetic seal；
S4, glass container is placed in constant temperature oscillator and is reacted, reaction temperature is 45 DEG C, hunting speed is
150rpm, the reaction time is 48h.After the completion of reaction, taking-up is placed in ice-water bath and cools down；
S5, by the solution filtration treatment obtained by S4, lipase is removed, then at 40 DEG C of temperature, relative degree of vacuum -0.06Mpa
Under the conditions of rotary evaporation, remove methyl tertiary butyl ether(MTBE), obtain crude product；
S6, by S5 gained crude product be dissolved in 95% ethanol, crude product:95% ethanol is controlled 1:20(g/mL)；Add
Sodium carbonate, the quality of crude product:The quality control of sodium carbonate is 1:1.2(g/g)；Add water, crude product:Water management is 1:6(g/
ML), by above-mentioned reactant mixture under nitrogen stream protection, in 40 DEG C of reaction temperatures, backflow saponification 30min；
S7, by S6 gained mixtures, be transferred in separatory funnel, with n-hexane extraction 3 times, each extraction n-hexane:
The control of 95% ethanol is 4 in S5:1 (mL/mL), the n-hexane layer anhydrous sodium sulfate water removal for obtaining, then in temperature 45 C, phase
To rotary evaporation under the conditions of vacuum -0.08Mpa, n-hexane is removed, obtain hydroxytyrosol-DHA ester, its quality is
19.9265g。
By above-mentioned steps, the esterification yield of hydroxytyrosol is 42.9%.Using HPLC-UV (efficient liquid phases-ultraviolet detection
Device) detection, hydroxytyrosol-DHA ester, purity is 87.2%.
Embodiment 3
S1,0.1mol hydroxytyrosols are taken in sealable glass container, be slowly added to methyl tertiary butyl ether(MTBE), hydroxyl junket
Alcohol:Methyl tertiary butyl ether(MTBE) is controlled 1:30 (mol/L), are then fully mixed by ultrasonic；
S2, take during 0.8mol DHA add S1 resulting solutions, then fully mixed by ultrasonic；
S3, take lipase (Novozyme-435, from antarctic candida, EC 3.1.1.3) add S2 resulting solutions
In, the quality of enzyme:The molal quantity of hydroxytyrosol is controlled 40:1 (g/mol), then to glass container nitrogen charging hermetic seal；
S4, glass container is placed in constant temperature oscillator and is reacted, reaction temperature is 40 DEG C, hunting speed is
150rpm, the reaction time is 48h.After the completion of reaction, taking-up is placed in ice-water bath and cools down；
S5, by the solution filtration treatment obtained by S4, lipase is removed, then at 40 DEG C of temperature, relative degree of vacuum -0.07Mpa
Under the conditions of rotary evaporation, remove methyl tertiary butyl ether(MTBE), obtain crude product；
S6, by S5 gained crude product be dissolved in 95% ethanol, the quality of crude product:The fixing fabric structure of 95% ethanol is 1:15
(g/mL)；Add sodium carbonate, the quality of crude product:The quality control of sodium carbonate is 1:0.8(g/g)；Add water, the matter of crude product
Amount:The fixing fabric structure of water is 1:5 (g/mL), by above-mentioned reactant mixture under nitrogen stream protection, in 40 DEG C of reaction temperatures, backflow
Saponification 30min；
S7, by S6 gained mixtures, be transferred in separatory funnel, with n-hexane extraction 2 times, each extraction n-hexane:
The control of 95% ethanol is 6 in S5:1 (mL/mL), the n-hexane layer anhydrous sodium sulfate water removal for obtaining, then in 40 DEG C of temperature, phase
To rotary evaporation under the conditions of vacuum -0.06Mpa, n-hexane is removed, obtain hydroxytyrosol-DHA ester, its quality is
19.4156g。
By above-mentioned steps, the esterification yield of hydroxytyrosol is 41.8%.Using HPLC-UV (efficient liquid phases-ultraviolet detection
Device) detection, hydroxytyrosol-DHA ester, purity is 86.5%.
Embodiment 4
S1,0.1mol hydroxytyrosols are taken in sealable glass container, be slowly added to methyl tertiary butyl ether(MTBE), hydroxyl junket
Alcohol:Methyl tertiary butyl ether(MTBE) is controlled 1:50 (mol/L), are then fully mixed by ultrasonic；
S2, take during 1.2molDHA adds S1 resulting solutions, then fully mixed by ultrasonic；
S3, take lipase (Novozyme-435, from antarctic candida, EC 3.1.1.3) add S2 resulting solutions
In, the quality of enzyme:The molal quantity of hydroxytyrosol is controlled 60:1 (g/mol), then to glass container nitrogen charging hermetic seal；
S4, glass container is placed in constant temperature oscillator and is reacted, reaction temperature is 50 DEG C, hunting speed is
200rpm, the reaction time is 72h, and after the completion of reaction, taking-up is placed in ice-water bath and cools down；
S5, by the solution filtration treatment obtained by S4, lipase is removed, then at temperature 45 C, relative degree of vacuum -0.05Mpa
Under the conditions of rotary evaporation, remove methyl tertiary butyl ether(MTBE), obtain crude product；
S6, by S5 gained crude product be dissolved in 95% ethanol, crude product:95% ethanol is controlled 1:20(g/mL)；Add
Sodium carbonate, crude product:Sodium carbonate is controlled 1:1.2(g/g)；Add water, crude product:Water management is 1:6 (g/mL), will be above-mentioned anti-
Mixture is answered under nitrogen stream protection, in 50 DEG C of reaction temperatures, backflow saponification 30min；
S7, by S6 gained mixtures, be transferred in separatory funnel, with n-hexane extraction 3 times, each extraction n-hexane:
The control of 95% ethanol is 4 in S5:1 (mL/mL), the n-hexane layer anhydrous sodium sulfate water removal for obtaining, then in 40 DEG C of temperature, phase
To rotary evaporation under the conditions of vacuum -0.06Mpa, n-hexane is removed, obtain hydroxytyrosol-DHA ester, its quality is
19.6942g。
By above-mentioned steps, the esterification yield of hydroxytyrosol is 42.4%.Using HPLC-UV (efficient liquid phases-ultraviolet detection
Device) detection, hydroxytyrosol-DHA ester, purity is 87.1%.
Embodiment 5
S1,0.1mol hydroxytyrosols are taken in sealable glass container, be slowly added to methyl tertiary butyl ether(MTBE), hydroxyl junket
Alcohol:Methyl tertiary butyl ether(MTBE) is controlled 1:40 (mol/L), are then fully mixed by ultrasonic；
S2, take during 1molDHA adds S1 resulting solutions, then fully mixed by ultrasonic；
S3, take lipase (Novozyme-435, from antarctic candida, EC 3.1.1.3) add S2 resulting solutions
In, enzyme:Hydroxytyrosol is controlled 45:1 (g/mol), then to glass container nitrogen charging hermetic seal；
S4, glass container is placed in constant temperature oscillator and is reacted, reaction temperature is 45 DEG C, hunting speed is
150rpm, the reaction time is 48h, and after the completion of reaction, taking-up is placed in ice-water bath and cools down；
S5, by the solution filtration treatment obtained by S4, lipase is removed, then at 40 DEG C of temperature, relative degree of vacuum -0.06Mpa
Under the conditions of rotary evaporation, remove methyl tertiary butyl ether(MTBE), obtain crude product；
S6, by S5 gained crude product be dissolved in 95% ethanol, the quality of crude product:The fixing fabric structure of 95% ethanol is 1:15
(g/mL)；Add sodium carbonate, crude product:Sodium carbonate is controlled 1:1.0(g/g)；Add water, crude product:Water management is 1:5(g/
ML), by above-mentioned reactant mixture under nitrogen stream protection, in 50 DEG C of reaction temperatures, backflow saponification 25min；
S7, by S6 gained mixtures, be transferred in separatory funnel, with n-hexane extraction 3 times, each extraction n-hexane:
The control of 95% ethanol is 4 in S5:1 (mL/mL), the n-hexane layer anhydrous sodium sulfate water removal for obtaining, then in 40 DEG C of temperature, phase
To rotary evaporation under the conditions of vacuum -0.06Mpa, n-hexane is removed, obtain hydroxytyrosol-DHA ester, its quality is
19.4620g。
By above-mentioned steps, the esterification yield of hydroxytyrosol is 41.9%.Using HPLC-UV (efficient liquid phases-ultraviolet detection
Device) detection, hydroxytyrosol-DHA ester, purity is 86.0%.
Embodiment 6
S1,0.1mol hydroxytyrosols are taken in sealable glass container, be slowly added to methyl tertiary butyl ether(MTBE), hydroxyl junket
Alcohol:Methyl tertiary butyl ether(MTBE) is controlled 1:45 (mol/L), are then fully mixed by ultrasonic；
S2, take during 1mol DHA add S1 resulting solutions, then fully mixed by ultrasonic；
S3, take lipase (Novozyme-435, from antarctic candida, EC 3.1.1.3) add S2 resulting solutions
In, enzyme:Hydroxytyrosol is controlled 50:1 (g/mol), then to glass container nitrogen charging hermetic seal；
S4, glass container is placed in constant temperature oscillator and is reacted, reaction temperature is 50 DEG C, hunting speed is
200rpm, the reaction time is 72h, and after the completion of reaction, taking-up is placed in ice-water bath and cools down；
S5, by the solution filtration treatment obtained by S4, lipase is removed, then at temperature 45 C, relative degree of vacuum -0.06Mpa
Under the conditions of rotary evaporation, remove methyl tertiary butyl ether(MTBE), obtain crude product；
S6, by S5 gained crude product be dissolved in 95% ethanol, crude product:95% ethanol is controlled 1:20(g/mL)；Add
Sodium carbonate, crude product:Sodium carbonate is controlled 1:1.0(g/g)；Add water, crude product:Water management is 1:6 (g/mL), will be above-mentioned anti-
Mixture is answered under nitrogen stream protection, in 40 DEG C of reaction temperatures, backflow saponification 30min；
S7, by S6 gained mixtures, be transferred in separatory funnel, with n-hexane extraction 3 times, each extraction n-hexane：
The control of 95% ethanol is 4 in S5:1 (mL/mL), the n-hexane layer anhydrous sodium sulfate water removal for obtaining, then in 40 DEG C of temperature, phase
To rotary evaporation under the conditions of vacuum -0.06Mpa, n-hexane is removed, obtain hydroxytyrosol-DHA ester, its quality is
19.5084g。
By above-mentioned steps, the esterification yield of hydroxytyrosol is 42.0%.Using HPLC-UV (efficient liquid phases-ultraviolet detection
Device) detection, hydroxytyrosol-DHA ester, purity is 86.7%.
The above, the only present invention preferably specific embodiment, but protection scope of the present invention is not limited thereto,
Any one skilled in the art in the technical scope of present disclosure, technology according to the present invention scheme and its
Inventive concept is subject to equivalent or change, should all be included within the scope of the present invention.
Claims (2)
1. a kind of method that utilization lipase prepares hydroxytyrosol-DHA ester, it is characterised in that including following step
Suddenly：
S1, to methyl tertiary butyl ether(MTBE) is added in hydroxytyrosol, ultrasound is fully mixed, and obtains hydroxytyrosol solution, the hydroxyl junket
Alcohol is 1 with methyl tertiary butyl ether(MTBE) molal volume ratio:25~50 (mol/L)；
S2, take DHA and be added in the hydroxytyrosol solution obtained by step S1, ultrasound is fully mixed, and obtains alkyd
Mixed solution；The DHA is 6~12 with hydroxytyrosol mol ratio:1；
S3, take lipase EC 3.1.1.3 and be added in the alkyd mixed solution obtained by step S2, seal inflated with nitrogen, obtain fat
Enzyme solutions；The lipase EC 3.1.1.3 >=5000U/g, the lipase EC3.1.1.3 and hydroxytyrosol mass volume ratio
It is 30~60:1(g/mol)；
S4, by the lipase solution obtained by step S3, be placed in 35~50 DEG C, 24~72h of oscillating reactions under 100~200rpm environment
Afterwards, take out to be placed in ice-water bath and cool down, obtain enzyme reaction solution；
S5, by the enzyme reaction solution filtration treatment obtained by step S4, remove lipase, then at 35~45 DEG C, relative degree of vacuum-
Rotary evaporation under the conditions of 0.05~-0.08Mpa, removes methyl tertiary butyl ether(MTBE), obtains crude product；
S6, by step S5 gained crude product be dissolved in the ethanol that volumetric concentration is 95%, add sodium carbonate, water, nitrogen protection,
Flow back 20~30min of saponification at 40~50 DEG C, obtains saponification solution；The crude product and the ethanol mass body that volumetric concentration is 95%
Product is than being 1:10~20 (g/mL), the crude product is 1 with sodium carbonate mass ratio:0.8~1.2, the crude product and water quality
Volume ratio is 1:4~6 (g/mL)；
S7, by the n-hexane extraction 1~3 time of the saponification solution obtained by step S6, the n-hexane layer for obtaining is removed with anhydrous sodium sulfate
Water, then the rotary evaporation under the conditions of 35~45 DEG C, relative degree of vacuum -0.05~-0.08Mpa, removes n-hexane, obtains hydroxyl
Tyrosol-DHA ester；The volume and volumetric concentration used in step S6 of extraction n-hexane used are 95% every time
The ratio of the volume of ethanol is 2~6:1.
2. the method for being prepared hydroxytyrosol-DHA ester using lipase according to claim 1, its feature is existed
In lipase EC 3.1.1.3 described in step S3 are Novozyme-435, from antarctic candida.
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Cited By (1)
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Application publication date: 20170531 |