CN106083558B - The method that anti-tumor active ingredient is detached from wheat embryo fermentate - Google Patents
The method that anti-tumor active ingredient is detached from wheat embryo fermentate Download PDFInfo
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- CN106083558B CN106083558B CN201610527995.6A CN201610527995A CN106083558B CN 106083558 B CN106083558 B CN 106083558B CN 201610527995 A CN201610527995 A CN 201610527995A CN 106083558 B CN106083558 B CN 106083558B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention discloses a kind of methods that anti-tumor active ingredient is detached in fermentate from wheat embryo, including：Superparamag-netic iron oxide is directly added into wheat embryo zymotic fluid, superparamag-netic iron oxide is made fully to adsorb antitumor 1,4-benzoquinone therein, the antitumor 1,4-benzoquinone includes methoxyl-p-benzoquinone and 2,6 dimethoxy 1,4-benzoquinone.The present invention directly adsorbs the antitumor 1,4-benzoquinone in wheat embryo zymotic fluid using superparamag-netic iron oxide, without in the affine substance of magnetic iron oxide particle area load, without being pre-processed to zymotic fluid, 1,4-benzoquinone that can be in efficient absorption wheat embryo zymotic fluid, separation is quick, and adsorption capacity is big, safe and non-toxic harmless, and superparamag-netic iron oxide is reusable, it is of low cost.
Description
Technical field
Present invention relates particularly to superparamag-netic iron oxides in separation wheat plumule fermentate in antitumor 1,4-benzoquinone
Purposes, belong to bioengineering field.
Background technology
Medicament containing quinones substance is the second largest kind anti-cancer drugs agent, is in clinical trial there are many medicament containing quinones
Stage.The study found that two kinds of 1,4-benzoquinone in fermentation plumule can induce cancer cell-apoptosis, and can improve the immunity of the human body.Therefore,
Wheat embryo fermentate has been approved as the dietary product of cancer patient by Hungary's food security and nutrition department.
Two kinds of 1,4-benzoquinone, that is, methoxyl-p-benzoquinones and 2,6- dimethoxy 1,4-benzoquinone in fermentation plumule, which have, significantly to be resisted
Tumor promotion, and two kinds of 1,4-benzoquinone have good synergistic effect with anticarcinogen Dacarbazine and 5 FU 5 fluorouracil.But
In field of food industry, isolating and purifying for bioactive substance would generally use solvent extraction, the precipitation method, ultrafiltration and preparation
Type liquid chromatography.However, these separation methods have certain defect, longer, equipment costliness, waste of solvent etc. are such as taken.
Invention content
The main purpose of the present invention is to provide a kind of superparamag-netic iron oxides in the antitumor 1,4-benzoquinone of separation
The purposes of purposes, especially superparamag-netic iron oxide in separation wheat plumule fermentate in two kinds of antitumor 1,4-benzoquinone,
With overcome the deficiencies in the prior art.
For realization aforementioned invention purpose, the technical solution adopted by the present invention includes：
An embodiment of the present invention provides purposes of the superparamag-netic iron oxide in the antitumor 1,4-benzoquinone of separation.
Further, an embodiment of the present invention provides the magnetic iron oxide (Fe that grain size is 10.1~108.6nm3O4) nanometer
Purposes of the particle in antitumor 1,4-benzoquinone in extraction wheat embryo zymotic fluid.
Further, the purposes includes：Superparamag-netic iron oxide is directly added into wheat embryo zymotic fluid
In, so that superparamag-netic iron oxide is fully adsorbed antitumor 1,4-benzoquinone therein, the antitumor 1,4-benzoquinone includes methoxyl group
1,4-benzoquinone and 2,6- dimethoxy 1,4-benzoquinone.
An embodiment of the present invention provides a kind of method that anti-tumor active ingredient is detached in fermentate from wheat embryo, packets
It includes：The antitumor 1,4-benzoquinone in the liquid-phase system containing antitumor 1,4-benzoquinone is directly adsorbed with superparamag-netic iron oxide.
Further, the method includes：It is directly inhaled with the superparamag-netic iron oxide that grain size is 10.1~108.6nm
Antitumor 1,4-benzoquinone in attached primary school's wheat germ zymotic fluid.
Compared with prior art, advantages of the present invention includes：
(1) directly synthesize the superparamag-netic iron oxide with absorption 1,4-benzoquinone substance, without negative in particle surface
Affine substance is carried, without being pre-processed to zymotic fluid, and separation purifying technique is simple to operation；
(2) superparamag-netic iron oxide prepares that raw material is simple, synthesis condition is mild, it is short to take, and obtains magnetic oxygen
It is reusable to change iron nano-particle；
(3) the superparamag-netic iron oxide purity that synthesizes is high, it is nontoxic, with good magnetism；
(4) superparamag-netic iron oxide provided can thoroughly adsorb two kinds of 1,4-benzoquinone, adsorption capacity 40mg/g-
60mg/g；
(5) it can realize that nano particle detaches by Magnetic Isolation under the action of externally-applied magnetic field, after removing target substance, nanometer
Particle is reusable after ultrasonic cleaning.
Description of the drawings
Fig. 1 is the x-ray diffraction pattern of superparamag-netic iron oxide obtained in the present invention, curve a, b, c difference in figure
Corresponding to embodiment 1,2,3 (i.e. example 1,2,3)；
Fig. 2 is the Fourier transform infrared spectroscopy figure of superparamag-netic iron oxide obtained in the present invention, curve in figure
A, b, c correspond respectively to embodiment 1,2,3；
Fig. 3 a- Fig. 3 c are the grain size distribution of superparamag-netic iron oxide obtained in 1-3 of the embodiment of the present invention respectively.
Specific implementation mode
In view of deficiency in the prior art, inventor is able to propose the present invention's through studying for a long period of time and largely putting into practice
Technical solution.The technical solution, its implementation process and principle etc. will be further explained as follows.
An embodiment of the present invention provides a kind of method that anti-tumor active ingredient is detached in fermentate from wheat embryo, packets
It includes：The antitumor 1,4-benzoquinone in the liquid-phase system containing antitumor 1,4-benzoquinone is directly adsorbed with superparamag-netic iron oxide.
Further, the method includes：Superparamag-netic iron oxide is directly added into wheat embryo zymotic fluid, is made
Superparamag-netic iron oxide fully adsorbs antitumor 1,4-benzoquinone therein, and the antitumor 1,4-benzoquinone includes methoxyl-p-benzoquinone
With 2,6- dimethoxy 1,4-benzoquinone.
Further, the method includes：It is directly inhaled with the superparamag-netic iron oxide that grain size is 10.1~108.6nm
Antitumor 1,4-benzoquinone in attached primary school's wheat germ zymotic fluid.
Further, the method may also include：Make antitumor 1,4-benzoquinone desorption from superparamag-netic iron oxide.
Further, the method includes:By wheat embryo zymotic fluid and superparamag-netic iron oxide in shaking speed
To mix 2h or more, preferably 2~12h under the conditions of 60-200rpm.
It is more preferred, at the beginning of the superparamag-netic iron oxide and the fermentation to form the wheat embryo zymotic fluid
The mass ratio of beginning plumule is more than 1：50.
Particularly preferably, the superparamag-netic iron oxide in the additive amount in wheat embryo zymotic fluid be 2~4g/L.
Further, the method includes：By superparamag-netic iron oxide electromagnet out of wheat embryo zymotic fluid
It separates, is dissolved in 50% ethanol solution, superparamag-netic iron oxide is separated and recycled after ultrasonic 10min, gained
Clear liquid is enriched with aforementioned antitumor 1,4-benzoquinone.
Further, the method includes：Superparamag-netic iron oxide is regenerated, regeneration method deionized water
It is alternately cleaned with acetate buffer.Wherein acetic acid concentration can be 0.05M, clean 2min every time, recycle at least 3 times, after cleaning
Superparamag-netic iron oxide can dry after preserve, can also be resuspended in deionized water and preserve.
Further, the preparation method of the wheat embryo zymotic fluid includes：Wheat embryo fermenting microbe selects saccharomycete
Or lactic acid bacteria, inoculum concentration are 2~5%, wherein OD600It is 0.2~1.2, a concentration of 50~100g/L of plumule in zymotic fluid, fermentation
Temperature is 28~35 DEG C, and shaking speed is 60~200rpm, and fermentation time is not less than for 24 hours.
An embodiment of the present invention provides purposes of the superparamag-netic iron oxide in the antitumor 1,4-benzoquinone of separation, including：
Two kinds of antitumor 1,4-benzoquinone in liquid-phase system are directly adsorbed with superparamag-netic iron oxide.
An embodiment of the present invention provides the magnetic iron oxide (Fe that grain size is 10.1~108.6nm3O4) nano particle is in extraction
Purposes in wheat embryo zymotic fluid in antitumor 1,4-benzoquinone, including：Wheat is directly adsorbed with superparamag-netic iron oxide
Antitumor 1,4-benzoquinone in bud zymotic fluid.
In some embodiments, the purposes includes：Ferric salt solution is mixed with aqueous slkali, solution is moved to
Reaction in autoclave, is made superparamag-netic iron oxide；Appropriate superparamag-netic iron oxide is directly added into wheat embryo
In zymotic fluid, superparamag-netic iron oxide is recycled with electromagnet after the completion of absorption.
Further, the purposes includes：Superparamag-netic iron oxide is directly added into wheat embryo zymotic fluid,
Superparamag-netic iron oxide is set fully to adsorb antitumor 1,4-benzoquinone therein, the antitumor 1,4-benzoquinone includes methoxyl group to benzene
Quinone and 2,6- dimethoxy 1,4-benzoquinone.
Further, the purposes includes：Superparamag-netic iron oxide is directly added into wheat embryo zymotic fluid
In, and it is 60~200rpm to control shaking speed, adsorption time is 2~12h, so that superparamag-netic iron oxide is fully adsorbed anti-
Tumour 1,4-benzoquinone；The superparamag-netic iron oxide and the initial plumule of fermentation to form the wheat embryo zymotic fluid
Mass ratio is more than 1：50.
Preferably, additive amount of the superparamag-netic iron oxide in wheat embryo zymotic fluid is 2~4g/L.
Further, the purposes includes：Complete adsorb after, with electromagnet by superparamag-netic iron oxide from
It isolates, and is scattered in 50% ethanol solution in wheat embryo zymotic fluid, ultrasonic 10min or more, later by magnetic iron oxide
Nano particle separates and recovers, and gained clear liquid includes the antitumor 1,4-benzoquinone of enrichment.
Further, the purposes includes：By the superparamag-netic iron oxide of recycling with deionized water and concentration
It is alternately cleaned for the acetate buffer of 0.05M, realizes the regeneration treatment to the superparamag-netic iron oxide.
Further, the purposes includes：Ferric salt solution and aqueous slkali are stirred into 0.2~1h in 40~70 DEG C,
It is transferred to reaction in autoclave later, reaction temperature is 120~200 DEG C, and the time is 1~4h, and magnetic ferric oxide nano is made
Grain；Wherein, a concentration of 0.1~1M of ferric salt solution, alkaline concentration are 0.2~1.5M, ferric salt solution and alkali soluble
The volume ratio of liquid is 1:1-1:3.
Further, the trivalent iron salt include in iron chloride, ferric sulfate and ferric nitrate any one or it is two or more
Combination, but not limited to this.
Further, the aqueous slkali includes arbitrary in sodium hydroxide solution, sodium carbonate liquor and sodium borohydride solution
A combination of one or more, but not limited to this.
Further, the preparation method of the wheat embryo zymotic fluid includes：Wheat embryo fermenting microbe selects saccharomycete
Or lactic acid bacteria, inoculum concentration are 2~5%, wherein OD600It is 0.2~1.2, a concentration of 50~100g/L of plumule in zymotic fluid, fermentation
Temperature is 28~35 DEG C, and shaking speed is 60~200rpm, and fermentation time is 24~50h.
In some more specific embodiment, the purposes includes the following steps：
(1) superparamag-netic iron oxide is prepared；
(2) quality of superparamag-netic iron oxide and the initial plumule of fermentation to form the wheat embryo zymotic fluid
Than should be greater than 1：50, adsorption time is not less than 2h, 60~200rpm of shaking speed in adsorption process.
(3) superparamag-netic iron oxide in step (2) is separated with electromagnet, is dissolved in 50% ethanol solution,
Superparamag-netic iron oxide is separated after ultrasonic 10min, the gained stillness of night is the sample for being enriched with two kinds of 1,4-benzoquinone；
(4) superparamag-netic iron oxide that step (3) is isolated is regenerated, regeneration method deionized water and second
Acid buffer alternately cleans.Wherein a concentration of 0.05M of acetate buffer cleans 2min every time, recycles at least 3 times, after cleaning
Superparamag-netic iron oxide preserves after can drying, and can also be resuspended in deionized water and preserve.
The nano oxidized iron particle of applied magnetic provided by the invention isolates and purifies antitumor to benzene in wheat embryo zymotic fluid
The method of quinone can be effectively improved the shortcomings of traditional separation method solvent easily wastes, is complicated for operation, save the operating time, reduce and divide
From purifying cost.Meanwhile superparamag-netic iron oxide good biocompatibility of the invention, nontoxic, preparation method is simple,
It is of low cost, and waste of solvent caused by traditional isolation and purification method, monodisperse magnetic ferric oxide nano obtained can be reduced
Graininess matter stabilization is used multiple times, and has good adsorption effect to two kinds of 1,4-benzoquinone in wheat embryo zymotic fluid.
Below in conjunction with attached drawing and several embodiments the technical solution of the present invention is further explained explanation.
The preparation method of wheat embryo zymotic fluid includes in following examples：Wheat embryo fermenting microbe select saccharomycete or
Lactic acid bacteria, 2~5% (OD of inoculum concentration600It is 0.2~1.2), a concentration of 50~100g/L of plumule in zymotic fluid, fermentation temperature 28~
35 DEG C, 60~200rpm of shaking speed, fermentation time is not less than for 24 hours.
Embodiment 1
(1) preparation of superparamag-netic iron oxide：100g ferric chloride hexahydrates are dissolved in 1L distilled water and 40g hydrogen-oxygens
Change sodium and be dissolved in 1L distilled water and mix above two solution, 30min is stirred under the conditions of temperature is 60 DEG C, later by mixed liquor
It is transferred in autoclave under the conditions of 160 DEG C and reacts 2h, then black precipitate is separated with electromagnet, with distilled water and anhydrous
Ethyl alcohol washs for several times, obtains superparamag-netic iron oxide.With the JCPDS cards (Fe of standard3O4) compare, diffraction maximum difference
Corresponding to (111) (220) (311) (400) (422) (511) (440) of cubic system iron oxide, show obtained magnetic Nano
The crystalline phase of grain is Fe3O4, see attached drawing 1.594cm in Fourier transform infrared collection of illustrative plates-1Bands of a spectrum belong to Fe-O key stretching vibrations, see attached
Fig. 2.
(2) superparamag-netic iron oxide is directly added into wheat embryo zymotic fluid, superparamag-netic iron oxide
Additive amount is 2g/L, and it is 60rpm, adsorption time 12h to control shaking speed.Later by the magnetic iron oxide after adsorption treatment
Nano particle isolates zymotic fluid with electromagnet, and is scattered in the ethanol solution that volume fraction is 50% and is ultrasonically treated 10min,
Separation and recovery superparamag-netic iron oxide, above-mentioned clear liquid obtained as two kinds of 1,4-benzoquinone of enrichment (methoxyl-p-benzoquinone and 2,
6- dimethoxys 1,4-benzoquinone) sample.Test shows in the present embodiment, the adsorbable quality of every gram of superparamag-netic iron oxide
For the methoxyl-p-benzoquinone of 47mg and the 2,6- dimethoxy 1,4-benzoquinone of 45mg.
The superparamag-netic iron oxide of recycling can regeneration treatment in the following way：By the magnetic oxygenated of ultrasound post-processing
The acetic acid solution of iron nano-particle deionized water and a concentration of 0.05M alternately clean, and clean 2min or more, wash cycles every time
3 times or more, the superparamag-netic iron oxide after cleaning preserves after can drying, and can also be resuspended in deionized water and preserve, and can
It reuses.
Embodiment 2
(1) preparation of superparamag-netic iron oxide：60g ferric sulfate solutions are dissolved in 1L distilled water with 50g sodium carbonate
In 1L distilled water and above two solution is mixed, 60min is stirred under the conditions of temperature is 40 DEG C, later shifts mixed liquor supreme
1h is reacted under the conditions of 180 DEG C in pressure kettle, then black precipitate is separated with electromagnet, is washed with distilled water and absolute ethyl alcohol
For several times, superparamag-netic iron oxide is obtained.
(2) superparamag-netic iron oxide is directly added into wheat embryo zymotic fluid, superparamag-netic iron oxide adds
Dosage is 4g/L, and it is 200rpm, adsorption time 2h to control shaking speed.The magnetic iron oxide after adsorption treatment is received later
Rice grain isolates zymotic fluid with electromagnet, and is scattered in the ethanol solution that volume fraction is 50% and is ultrasonically treated 10min, point
From recycling superparamag-netic iron oxide, at the same above-mentioned clear liquid obtained be enriched with two kinds of 1,4-benzoquinone (methoxyl-p-benzoquinone and
2,6- dimethoxys 1,4-benzoquinone) sample.Test shows in the present embodiment, the adsorbable matter of every gram of superparamag-netic iron oxide
Amount is the 2,6- dimethoxy 1,4-benzoquinone of the methoxyl-p-benzoquinone and 46mg of 51mg.
The superparamag-netic iron oxide of recycling can regeneration treatment in the following way：By the magnetic oxygenated of ultrasound post-processing
The acetic acid solution of iron nano-particle deionized water and a concentration of 0.05M alternately clean, and clean 2min or more, wash cycles every time
3 times or more, the superparamag-netic iron oxide after cleaning preserves after can drying, and can also be resuspended in deionized water and preserve, and can
It reuses.
Embodiment 3
(1) preparation of superparamag-netic iron oxide：160g Fe(NO3)39H2Os are dissolved in 1L distilled water and 30g boron hydrogen
Change sodium and be dissolved in 1L distilled water and mix above two solution, 50min is stirred under the conditions of temperature is 50 DEG C, later by mixed liquor
It is transferred in autoclave under the conditions of 200 DEG C and reacts 4h, then black precipitate is separated with electromagnet, with distilled water and anhydrous
Ethyl alcohol washs for several times, obtains superparamag-netic iron oxide.
(2) superparamag-netic iron oxide is directly added into wheat embryo zymotic fluid, superparamag-netic iron oxide
Additive amount is 3g/L, and it is 120rpm, adsorption time 6h to control shaking speed.Later by the magnetic iron oxide after adsorption treatment
Nano particle isolates zymotic fluid with electromagnet, and is scattered in the ethanol solution that volume fraction is 50% and is ultrasonically treated 10min,
Superparamag-netic iron oxide is separated and recovered, while above-mentioned clear liquid obtained is to be enriched with two kinds of 1,4-benzoquinone (methoxyl-p-benzoquinones
With 2,6- dimethoxys 1,4-benzoquinone) sample.Test shows in the present embodiment that every gram of superparamag-netic iron oxide is adsorbable
Quality is the 2,6- dimethoxy 1,4-benzoquinone of the methoxyl-p-benzoquinone and 55mg of 54mg.
The superparamag-netic iron oxide of recycling can regeneration treatment in the following way：By the magnetic oxygenated of ultrasound post-processing
The acetic acid solution of iron nano-particle deionized water and a concentration of 0.05M alternately clean, and clean 2min or more, wash cycles every time
3 times or more, the superparamag-netic iron oxide after cleaning preserves after can drying, and can also be resuspended in deionized water and preserve, and can
It reuses.
It should be appreciated that the technical concepts and features of above-described embodiment only to illustrate the invention, its object is to allow be familiar with this
The personage of item technology cans understand the content of the present invention and implement it accordingly, and it is not intended to limit the scope of the present invention.It is all
According to equivalent change or modification made by spirit of the invention, should be covered by the protection scope of the present invention.
Claims (7)
1. a kind of method for detaching anti-tumor active ingredient in fermentate from wheat embryo, it is characterised in that including：
The superparamag-netic iron oxide that grain size is 10.1-108.6nm is directly added into wheat embryo zymotic fluid, and controls and shakes
Bed rotating speed is 60-200rpm, and adsorption time 2-12h makes superparamag-netic iron oxide fully adsorb antitumor 1,4-benzoquinone,
Described in superparamag-netic iron oxide and big to the mass ratio for forming the initial plumule of fermentation of the wheat embryo zymotic fluid
In 1：50；
After completing to adsorb, superparamag-netic iron oxide is isolated from wheat embryo zymotic fluid with electromagnet, and disperses
In water-ethanol mixed solvent, ultrasonic 10min or more later separates and recovers superparamag-netic iron oxide, gained clear liquid packet
Antitumor 1,4-benzoquinone containing enrichment, the antitumor 1,4-benzoquinone include methoxyl-p-benzoquinone and 2,6- dimethoxy 1,4-benzoquinone.
2. the method for detaching anti-tumor active ingredient in the fermentate according to claim 1 from wheat embryo, feature exist
In：Additive amount of the superparamag-netic iron oxide in wheat embryo zymotic fluid is 2-4g/L.
3. the method for detaching anti-tumor active ingredient in the fermentate according to claim 1 from wheat embryo, feature exist
In further including：The superparamag-netic iron oxide of recycling is handed over the acetate buffer of deionized water and a concentration of 0.05mol/L
For cleaning, the regeneration treatment to the superparamag-netic iron oxide is realized.
4. the method for detaching anti-tumor active ingredient in the fermentate according to claim 1 from wheat embryo, feature exist
In including：Ferric salt solution and aqueous slkali are stirred 0.2-1 hours in 40-70 DEG C, are transferred to reaction in autoclave later, instead
It is 120-200 DEG C, time 1-4h to answer temperature, and superparamag-netic iron oxide is made；Wherein, ferric salt solution is a concentration of
The volume ratio of 0.1-1M, alkaline concentration 0.2-1.5M, ferric salt solution and aqueous slkali is 1:1-1:3.
5. the method for detaching anti-tumor active ingredient in the fermentate according to claim 4 from wheat embryo, feature exist
In：The trivalent iron salt includes any one or two or more combinations in iron chloride, ferric sulfate and ferric nitrate.
6. the method for detaching anti-tumor active ingredient in the fermentate according to claim 1 from wheat embryo, feature exist
In：The aqueous slkali include in sodium hydroxide solution, sodium carbonate liquor and sodium borohydride solution any one or it is two or more
Combination.
7. the method for detaching anti-tumor active ingredient in the fermentate according to claim 1 from wheat embryo, feature exist
In the preparation method of the wheat embryo zymotic fluid includes：Wheat embryo fermenting microbe selects saccharomycete or lactic acid bacteria, inoculum concentration
For 2-5%, wherein OD600For 0.2-1.2, a concentration of 50-100g/L of plumule in zymotic fluid, fermentation temperature is 28-35 DEG C, shaking table
Rotating speed is 60-200rpm, and fermentation time is not less than for 24 hours.
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| CN109776692A (en) * | 2019-01-23 | 2019-05-21 | 武汉轻工大学 | A method of separating anti-tumor active ingredient from fermentation Chinese wolfberry fruit object |
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| JP2001352975A (en) * | 2000-06-15 | 2001-12-25 | Hiroyuki Sumi | Physiologically active substance derived from bacillus natto |
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| CN103224962A (en) * | 2013-05-14 | 2013-07-31 | 聊城九州和谷生物科技有限公司 | Production method of wheat germ fermentation product |
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