CN1425650A - Process for extracting alliin from fresh garlic - Google Patents
Process for extracting alliin from fresh garlic Download PDFInfo
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- CN1425650A CN1425650A CN 03100420 CN03100420A CN1425650A CN 1425650 A CN1425650 A CN 1425650A CN 03100420 CN03100420 CN 03100420 CN 03100420 A CN03100420 A CN 03100420A CN 1425650 A CN1425650 A CN 1425650A
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Abstract
The extraction process of alliin from fresh garlic includes the steps of: pre-treatment to kill enzyme of garlic with microwave; organic extraction through ginding garlic into slurry, ethanol extraction, separating extractive liquid and depression concentration; cationic exchange resin adsorption of alliin from concentrated extractive liquid; ammonia water desorption of alliin; and obtaining alliin crystal. The said process has alliin yield of 0.1% and product has alliin content of 91.2%.
Description
Technical field
The present invention relates to extract from plant the method for alliin organic substance, is a kind of alliin production technique of extracting from bright garlic.
Background technology
Garlic has another name called giant garlic, is the underground bulb of Liliaceae allium garlic (Allium sativum L.).It is time-honored medicine food dual purpose plant.Alliin has another name called alliin, mainly is present in the cell of garlic bulbil no color or smell.Chemical name: S-allyl group-L-halfcystine sulfoxide (S-allyl-L-cysteinesulfoxide), C
6H
11O
3SN, molecular weight: 177.22, fusing point: 163.5 ℃ ℃ (decomposition), chemical molecular formula is:
It is soluble in water and be insoluble to non-polar organic solvents such as ether.Alliin character instability under allinase (Allinase) and water effect, is converted into allicin (Allicin) rapidly under the normal temperature, produces acetone and ammonia.Wherein allicin also will further resolve into multiple sulfocompound.
Among the multiple organic compounds containing sulfur of garlic, alliin is counted as the main functional component of garlic, and more than 90% of the suitable total cure thing of content exists with polysaccharide bonded form, is the distinctive non-protein sulfur-containing amino acid of garlic.Experimentation on animals proves that alliin has effects such as antithrombotic, fungicidal.
Alliin and allinase independently are present in the bulb of garlic respectively, smash these two kinds of materials of back to pieces and are in contact with one another, and decomposition reaction takes place rapidly.Therefore from garlic, extract relatively difficulty of alliin.
The present inventor has invented a kind of method of extracting alliin from garlic, and its Chinese number of patent application is 00101244.4, but only suitable a small amount of alliin that extracts.
Summary of the invention
The invention provides a kind of extraction alliin production technique from bright garlic of suitable batch production.
Technical scheme of the present invention is achieved like this: a kind of alliin production technique of from bright garlic, extracting, carry out according to the following steps:
The first step is carried out pre-treatment: garlic clove is carried out microwave enzyme killing handles, make garlic clove from white become translucent till;
Second step carried out organism and extracts: the garlic clove after the microwave treatment is worn into 100 to 200 purpose garlics slurry, and adding ethanol, be 40% to 70% with ethanol specific gravity hydrometer control garlic slurry alcohol concn, stirred 2 to 10 hours, separate obtaining extracting solution, and the concentrating under reduced pressure extracting solution;
The 3rd step was used the alliin in the cationic exchange resin adsorption concentrated extracting solution: concentrated extracting solution is passed through the cationic exchange resin adsorption post;
The 4th step was used ammoniacal liquor desorb alliin: with 2.0 to 0.4 moles of ammonia water elution cationic exchange resin adsorption posts, collection pH value is the elutriant in 5.0 to 9.0 scopes;
The 5th step obtained the crystalline alliin: the concentrating under reduced pressure elutriant, and press 20% to 35% of concentrate eluant volume and add ethanol, and be in 5.5 to 6.5 scopes with hydrochloric acid or ammoniacal liquor adjusting pH value, room temperature left standstill 24 to 60 hours, separated out the crystalline alliin.
In above-mentioned pre-treatment: garlic clove can be placed microwave 2 to 5 minutes.
Above-mentioned microwave frequency can be 2540 ± 50MHz, and the output microwave power can be 20KW.
In above-mentioned concentrating under reduced pressure, concentrating under reduced pressure can adopt multiple-effect decompression thin film concentration method to carry out, the end outlet temperature be controlled in 40 to 60 ℃ of scopes or 70 to 90 ℃ of scopes in, the ratio of the liquid volume after concentrating and the weight of the bright garlic of raw material is controlled in 0.8 to 1.2 or 0.4 to 0.6 or 1/45 to 1/55 the scope.
In concentrated extracting solution, add 1 to 6% finings and stir, in temperature is-5 to 5 ℃ of scopes, place and obtain supernatant liquor after 5 to 20 hours, and supernatant liquor is carried out passing through the cationic exchange resin adsorption post behind the concentrating under reduced pressure, wherein finings is a fruit juice clarifier.
After the cationic exchange resin adsorption post is saturated, can wash adsorption column with distilled water earlier, and wash that to be Molish reaction negative or distilled water consumption to effluent liquid be 0.5 to 1.5 times of garlic clove weight, and then with ammoniacal liquor wash-out cationic exchange resin adsorption post.
After above-mentioned crystalline alliin is lower than 2.9% through drying under reduced pressure to the water content in 60 to 80 ℃ of scopes, carry out airtight preservation with nitrogen or rare gas element.
Above-mentioned separation equipment used can adopt freezing closed screenings self-separation paste roller mill or centrifugal dried machine or the low temperature tubular type separating centrifuge of falling; Or/and above-mentioned cationic exchange resin adsorption post can adopt styrene group strongly acidic cation exchange resin adsorption column or 732 type strong-acid cation-exchange resin adsorption columns or 850 type strong-acid cation-exchange resin adsorption columns or 800 type macroporous type strong acid sun resin absorption post.
It is the medicinal alliin of raw material mass production that the present invention is suitable for bright garlic.Through fusing point test, do the contrast of UV spectrum and infrared spectra with standard reference material, every index affirmation product is an alliin with products obtained therefrom of the present invention.Through efficient liquid phase chromatographic analysis, products obtained therefrom yield of the present invention is 1.0 ‰ ± 10%, and containing alliin is 91.2 ± 2%.
Description of drawings
Accompanying drawing 1 is the infrared absorpting light spectra of embodiment of the invention products obtained therefrom;
Accompanying drawing 2 is the infrared absorpting light spectra of standard reference material;
Accompanying drawing 3 is alliin efficient liquid phase chromatographic analysis (being HPLC) collection of illustrative plates (1-Alliin, 2-Acetanilide).
Embodiment
The present invention is not subjected to the restriction of following embodiment, can determine concrete embodiment according to the technical scheme and the practical situation of the invention described above.
Embodiment, undertaken by following step:
The first step is carried out pre-treatment: garlic clove is carried out microwave enzyme killing handles, make garlic clove from white become translucent till; Preferably garlic clove was placed microwave 2 minutes or 3.5 minutes or 5 minutes, and microwave frequency is preferably 2540 ± 50MHz, the output microwave power is preferably 20KW.Carrying out before microwave enzyme killing handles, preferably the garlic clove demoulding is being cleaned and drained.
Second step carried out organism and extracts: the garlic clove after the microwave treatment is worn into 100 to 200 purpose garlics slurry, and add ethanol or alcohol, and be 40% to 70% with ethanol specific gravity hydrometer control garlic slurry alcohol concn, stirring reaction 2 to 10 hours, separate obtaining extracting solution, and the concentrating under reduced pressure extracting solution.Preferably weight is extracted 3 times or 5 times again.Concentrating under reduced pressure preferably adopts multiple-effect decompression thin film concentration method to carry out, the end outlet temperature is controlled in 40 to 60 ℃ of scopes, recovered solvent is that ethanol is reusable, and the ratio of the extracting liquid volume after concentrating and the weight of the bright garlic of raw material is controlled in 0.8 to 1.2 the scope.Before adsorbing with the cationic exchange resin adsorption post, be preferably in the concentrated extracting solution and add 1% or 3% or 6% finings and stir, in temperature is-5 to 5 ℃ of scopes, place and obtain supernatant liquor after 5 hours or 10 hours or 20 hours, and supernatant liquor carried out adsorbing by the cationic exchange resin adsorption post behind the concentrating under reduced pressure, wherein finings is the fruit juice clarifier of selling on the market, as: can select the outstanding board 101 type fruit juice clarifiers of the Chinese of selling on the market for use, the ratio that supernatant liquor carries out the weight of the bright garlic of volume and raw material behind the concentrating under reduced pressure is controlled in 0.4 to 0.6 the scope, the end outlet temperature is controlled in 40 to 60 ℃ of scopes, and recovered solvent is that ethanol is reusable.
The 3rd step was used the alliin in the cationic exchange resin adsorption concentrated extracting solution: concentrated extracting solution or concentrated supernatant are passed through the cationic exchange resin adsorption post.After the cationic exchange resin adsorption post is saturated, preferably with distilled water adsorption column is washed earlier, and wash to effluent liquid and be the Molish reaction negative or the distilled water consumption is 0.5 times or 1.5 times of garlic clove weight, and then carry out the following step and promptly use ammoniacal liquor desorb alliin.
The 4th step was used ammoniacal liquor desorb alliin: with the ammoniacal liquor wash-out cationic exchange resin adsorption post in 2.0 to 0.4 molar range, collection pH value is the elutriant in 5.0 to 9.0 scopes;
The 5th step obtained the crystalline alliin: the concentrating under reduced pressure elutriant, wherein concentrating under reduced pressure is or/and solvent recuperation preferably adopts multiple-effect thin film concentration method to carry out, the end outlet temperature is controlled in 70 ℃ or 90 ℃ or 70 to the 90 ℃ of scopes, the ratio of the liquid volume after concentrating and the weight of the bright garlic of raw material is controlled in 1/45 to 1/55 the scope, recovered solvent is that ammoniacal liquor is reusable, press 20% or 35% of concentrate eluant volume then and add ethanol, and to regulate pH value with hydrochloric acid or ammoniacal liquor be in 5.5 to 6.5 scopes, room temperature left standstill 24 hours or 50 hours or 60 hours, separated out the crystalline alliin.After preferably the crystalline alliin being lower than 2.9% through drying under reduced pressure to the water content in 60 to 80 ℃ of scopes, carry out airtight preservation with nitrogen or rare gas element.
In the above-described embodiments: separate equipment used and preferably adopt freezing closed screenings self-separation paste roller mill or centrifugal dried machine or the low temperature tubular type separating centrifuge of falling; The cationic exchange resin adsorption post can adopt styrene group strongly acidic cation exchange resin adsorption column or 732 type strong-acid cation-exchange resin adsorption columns or 850 type strong-acid cation-exchange resin adsorption columns or 800 type macroporous type strong acid sun resin absorption post.
Be to be the affirmation of alliin to the foregoing description products obtained therefrom below:
Standard reference material: Alliin-S (Indofine Chemical Company Inc.USA, purity 99.5%, lot number: 97112003)
1, proterties
Product is a white crystalline powder.Very easily water-soluble.Be insoluble to ethanol, chloroform.Microscopically is viewed as colourless needle crystal.It is pH=5.7-6.2 that the polyacrylamide gel isoelectric focusing electrophoresis calculates iso-electric point.Conform to standard reference material.
2, fusing point
Measure fusing point according to 2000 editions two appendix VI C of Chinese Pharmacopoeia melting point determination, first method, the standard reference material fusing point is 164-166 ℃ (decomposition).This product fusing point is 162-165 ℃ (decomposition).2 ℃ in advance of this product fusing points, molten distance has expansion slightly, shows that product purity is not as good as standard reference material.
3, ultra-violet absorption spectrum confirms that product is an alliin, the suitable standard reference material 93.7% of estimation product alliin content
Alliin standard reference material (Alliin-S) is the solution that solvent is made 42 μ g/ml with methyl alcohol, dilutes 7 times.Record UV spectrum with S-50 type ultraviolet spectrophotometer (Shanghai rib light), maximum absorption is arranged at 226 ± 1nm place.Optical density is 0.380, E
1% 226 ± 1nm=90.5.This product (Alliin-D) is that solvent is made 40 μ g/ml solution with methyl alcohol, dilutes 7 times, measures UV spectrum under same instrument similarity condition, at 226 ± 1nm place maximum absorption is arranged.Optical density is 0.339.E
1％ 226±1nm＝84.8
Both ultra-violet absorption spectrums are identical.With E
1% 226 ± 1nm(Alliin-D) and E
1% 226 ± 1nm(Alliin-S) calculate alliin content.84.8/90.5 * 100=93.7, this product contain 93.7% of the suitable standard reference material of alliin.
4, infrared absorption spectrum
Alliin standard reference material and this product are at EQUINOX55, and BRUKER infrared spectrophotometer-ATR annex is measured infrared absorption spectrum.This product collection of illustrative plates (accompanying drawing 1) is consistent with standard reference material collection of illustrative plates (accompanying drawing 2).But 1533,1526cm etc. locates to occur small and weak peak.At the 1050-1430cm of fingerprint region section nuance is arranged.Illustrate that product contains small amount of impurities.
5, conclusion
The result's judgement and the affirmation embodiment products obtained therefrom that obtain according to proterties examination, fusing point test, ultra-violet absorption spectrum and infrared absorption spectrum analysis are alliin.
Below the foregoing description products obtained therefrom is measured its alliin content:
Measure alliin content in the present embodiment products obtained therefrom with efficient liquid phase chromatographic analysis (being HPLC).
1, test liquid preparation
Alliin standard reference material and embodiment products obtained therefrom add interior mark (Acetanilide) respectively, are configured to test liquid with moving phase.(content: the about 100.0 μ g/ml of alliin, Acetanilide 10.0 μ g/ml).
2, chromatographic condition
Agilent 1100 high performance liquid chromatographs, ZORBAX SB-C
18Post (4.6 * 250mm, 5.0 μ m); Moving phase: methanol-water (60: 40); Flow velocity 0.8ml/min; Detect wavelength 214nm; Column temperature: 37 ℃.Interior mark: Acetanilide.Test liquid sample size: 10 μ l.Obtain color atlas (accompanying drawing 3), retention time: alliin 3.07, Acetanilide 5.12.Resolution (R)=14.6, theoretical plate number (n)=7.4 * 10
3Sheet.
3, linearity and regression equation
Sample size in 0.5-3.0 μ g scope, with peak area to concentration map regression equation:
Y＝10.3X-9.8，r＝0.9993。
Withinday precision RSD=1.88% (n=5).Day to day precision RSD=2.65% (n=5).
4, the content of three batches of products of embodiment gained
Three batches of products of embodiment gained (lot number: A, B, C), through efficient liquid phase chromatographic analysis (being HPLC), three batches of product yields are 1.0 ‰ ± 10%, contain alliin 91.2 ± 2%.
5, determination of foreign matter
The three batches of products are according to Chinese Pharmacopoeia 2000 editions two appendix muriates, molysite, vitriol, ammonium salts are lower than, moisture, ash content are checked method check.The result is: muriate, molysite, vitriol are lower than 0.01%.Ammonium salt is lower than 0.02%.Moisture: 2.2-2.6%.Ash content 0.07-0.11%.
Claims (10)
1, a kind of alliin production technique of extracting from bright garlic is characterized in that carrying out according to the following steps:
The first step is carried out pre-treatment: garlic clove is carried out microwave enzyme killing handles, make garlic clove from white become translucent till;
Second step carried out organism and extracts: the garlic clove after the microwave treatment is worn into 100 to 200 purpose garlics slurry, and adding ethanol, alcohol concn with ethanol specific gravity hydrometer control garlic slurry is 40% to 70%, stirred 2 to 5 hours, separate obtaining extracting solution, film concentrating under reduced pressure extracting solution also adds finings except that solid impurity;
The 3rd step was used the alliin in the cationic exchange resin adsorption concentrated extracting solution: concentrated extracting solution is passed through the cationic exchange resin adsorption post;
The 4th step was used ammoniacal liquor desorb alliin: with 2.0 to 0.4 moles of ammonia water elution cationic exchange resin adsorption posts, collection pH value is the elutriant in 5.0 to 9.0 scopes;
The 5th step obtained the crystalline alliin: the concentrating under reduced pressure elutriant, and press 20% to 35% of concentrate eluant volume and add ethanol, and be in 5.5 to 6.5 scopes with hydrochloric acid or ammoniacal liquor adjusting pH value, room temperature left standstill 24 to 60 hours, separated out the crystalline alliin.
2, the alliin production technique of extracting from bright garlic according to claim 1 is characterized in that garlic clove was placed microwave oven 2 to 5 minutes.
3, the alliin production technique of extracting from bright garlic according to claim 2 is characterized in that microwave frequency is 2540 ± 50MHz, and the output microwave power is 20KW.
4, according to claim 1 or the 2 or 3 described alliin production technique of from bright garlic, extracting, it is characterized in that concentrating under reduced pressure adopts multiple-effect decompression thin film concentration method to carry out, the end outlet temperature be controlled in 40 to 60 ℃ of scopes or 70 to 90 ℃ of scopes in, the ratio of the liquid volume after concentrating and the weight of the bright garlic of raw material is controlled in 0.8 to 1.2 or 0.4 to 0.6 or 1/45 to 1/55 the scope.
5, according to claim 1 or the 2 or 3 described alliin production technique of from bright garlic, extracting, it is characterized in that in concentrated extracting solution, adding 1 to 6% finings and stirring, in temperature is-5 to 5 ℃ of scopes, place and obtain supernatant liquor after 5 to 20 hours, then supernatant liquor is passed through the cationic exchange resin adsorption post, wherein finings is a fruit juice clarifier.
6, the alliin production technique of from bright garlic, extracting according to claim 4, it is characterized in that in concentrated extracting solution, adding 1 to 6% finings and stirring, in temperature is-5 to 5 ℃ of scopes, place and obtain supernatant liquor after 5 to 20 hours, then supernatant liquor is passed through the cationic exchange resin adsorption post, wherein finings is a fruit juice clarifier.
7, according to claim 1 or 2 or the 3 or 6 described alliin production technique of from bright garlic, extracting, after it is characterized in that the cationic exchange resin adsorption post is saturated, with distilled water adsorption column is washed earlier, and wash that to be Molish reaction negative or distilled water consumption to effluent liquid be 0.5 to 1.5 times of garlic clove weight, and then with ammoniacal liquor wash-out cationic exchange resin adsorption post.
8, the alliin production technique of from bright garlic, extracting according to claim 4, after it is characterized in that the cationic exchange resin adsorption post is saturated, with distilled water adsorption column is washed earlier, and wash that to be Molish reaction negative or distilled water consumption to effluent liquid be 0.5 to 1.5 times of garlic clove weight, and then with ammoniacal liquor wash-out cationic exchange resin adsorption post.
9, according to claim 1 or 2 or 3 or the 6 or 8 described alliin production technique of from bright garlic, extracting, after it is characterized in that the crystalline alliin is lower than 2.9% through drying under reduced pressure to the water content in 60 to 80 ℃ of scopes, carry out airtight preservation with nitrogen or rare gas element.
10, according to claim 1 or 2 or 3 or the 6 or 8 described alliin production technique of from bright garlic, extracting, it is characterized in that separating equipment used and adopt freezing closed screenings self-separation paste roller mill or centrifugal dried machine or the low temperature tubular type separating centrifuge of falling; Or/and the cationic exchange resin adsorption post adopts styrene group strongly acidic cation exchange resin adsorption column or 732 type strong-acid cation-exchange resin adsorption columns or 850 type strong-acid cation-exchange resin adsorption columns or 800 type macroporous type strong acid sun resin absorption post.
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Cited By (9)
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| JP2007084500A (en) * | 2005-09-26 | 2007-04-05 | T Hasegawa Co Ltd | Method for producing extract containing s-alkenyl(or alkyl)cysteine sulfoxide compounds in high concentration |
| CN101444272B (en) * | 2008-12-26 | 2012-04-11 | 许昌元化生物科技有限公司 | Novel process for deodorizing garlic oil |
| CN104059002A (en) * | 2014-06-27 | 2014-09-24 | 齐鲁工业大学 | Ultrasonic assisted aqueous two-phase extraction method for alliin |
| CN105541681A (en) * | 2015-12-24 | 2016-05-04 | 青岛自然珍萃生物科技有限公司 | Preparation method of high-content alliin |
| CN105820097A (en) * | 2016-05-20 | 2016-08-03 | 兰州大学 | Method for extracting isoalliin in onion cells through nitrogen pressurization and ethanol substitution |
| CN107973731A (en) * | 2018-01-09 | 2018-05-01 | 金乡县大蒜研究所 | A kind of method for extracting garlic alliin |
| CN108531524A (en) * | 2018-03-22 | 2018-09-14 | 姚福兰 | From method, alliin and the drink of the only head extracting alliin from garlic of purple skin |
| CN108929252A (en) * | 2018-07-12 | 2018-12-04 | 西安青春康美生物科技有限公司 | A method of extracting separation S-allylcysteine from garlic |
| CN109535049A (en) * | 2017-09-22 | 2019-03-29 | 江苏智谋科技有限公司 | A kind of extracting method of alliin |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2007084500A (en) * | 2005-09-26 | 2007-04-05 | T Hasegawa Co Ltd | Method for producing extract containing s-alkenyl(or alkyl)cysteine sulfoxide compounds in high concentration |
| CN101444272B (en) * | 2008-12-26 | 2012-04-11 | 许昌元化生物科技有限公司 | Novel process for deodorizing garlic oil |
| CN104059002A (en) * | 2014-06-27 | 2014-09-24 | 齐鲁工业大学 | Ultrasonic assisted aqueous two-phase extraction method for alliin |
| CN104059002B (en) * | 2014-06-27 | 2016-08-17 | 齐鲁工业大学 | A kind of ultrasonic wave added aqueous two-phase extracts the method for alliin |
| CN105541681A (en) * | 2015-12-24 | 2016-05-04 | 青岛自然珍萃生物科技有限公司 | Preparation method of high-content alliin |
| CN105820097A (en) * | 2016-05-20 | 2016-08-03 | 兰州大学 | Method for extracting isoalliin in onion cells through nitrogen pressurization and ethanol substitution |
| CN105820097B (en) * | 2016-05-20 | 2017-10-13 | 兰州大学 | A kind of method that nitrogen pressurization ethanol replacement extracts different alliin in onion cells |
| CN109535049A (en) * | 2017-09-22 | 2019-03-29 | 江苏智谋科技有限公司 | A kind of extracting method of alliin |
| CN107973731A (en) * | 2018-01-09 | 2018-05-01 | 金乡县大蒜研究所 | A kind of method for extracting garlic alliin |
| CN108531524A (en) * | 2018-03-22 | 2018-09-14 | 姚福兰 | From method, alliin and the drink of the only head extracting alliin from garlic of purple skin |
| CN108929252A (en) * | 2018-07-12 | 2018-12-04 | 西安青春康美生物科技有限公司 | A method of extracting separation S-allylcysteine from garlic |
| CN108929252B (en) * | 2018-07-12 | 2020-05-15 | 西安青春康美生物科技有限公司 | Method for extracting and separating S-allylcysteine from garlic |
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