CN106957883A - A kind of allicin synthesizes the process of 4,5,9-trithiadodeca-1,6,11-triene 9-oxide - Google Patents
A kind of allicin synthesizes the process of 4,5,9-trithiadodeca-1,6,11-triene 9-oxide Download PDFInfo
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Abstract
The invention belongs to garlic deep process technology field, and in particular to a kind of process of allicin synthesis ajoene and preparation method thereof.Comprise the steps of：Allinase extraction, allinase purifying, allinase immobilization, prepare allicin, synthesis 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, 4,5,9-trithiadodeca-1,6,11-triene 9-oxide purifying.The present invention fixes allinase using enzyme immobilization technology, in bioreactor, and catalysis alliin is converted into allicin, and reaction selectivity is good, and high catalytic efficiency can obtain the allicin product of high-purity；Allicin is complexed to improve the stabilization of allicin by the characteristics of for allicin cracking reaction, the form reacted using complex catalysis with hydrophilic complex compound, the solution complexing in reaction, such allicin reacts generation ajoene in time, it is to avoid substantial amounts of side reaction occurs.
Description
Technical field
The invention belongs to garlic deep process technology field, and in particular to a kind of process of allicin synthesis 4,5,9-trithiadodeca-1,6,11-triene 9-oxide and
Its preparation method.
Background technology
Allicin (Allicin, garlicin) is three thio-allyl ether class compounds, is naturally occurring in liliaceous plant
In the bulb of garlic.There is antibacterial action to a variety of Gram-positives and negative bacterium, it is (shigella dysenteriae, typhoid bacillus, big to bacillus
Enterobacteria, Bordetella pertussis), fungi (Candida albicans, cryptococcus, aspergillus fumigatus), viral (cytomegalovirus), amoeba it is former
Worm, Trichomonas vaginalis, pinworm etc. have suppression killing action, especially act on strong to enteric bacteria such as Escherichia coli, shigella dysenteriaes.
But, allicin is extremely unstable, will be decomposed in normal temperature condition.4,5,9-trithiadodeca-1,6,11-triene 9-oxide is used as one kind activity from garlic
Composition, more stablizes than allicin and without the peppery garlic odour smell of unacceptable garlic, with antithrombus formation, induction is swollen
Oncocyte, which is adjusted, dies and the special physiological function such as anti-inflammation, is a kind of active component of efficiency natural.But allicin
In acetone/water system, catabolite is mainly E/Z- 4,5,9-trithiadodeca-1,6,11-triene 9-oxides.These catabolites result in allicin, and to be converted into 4,5,9-trithiadodeca-1,6,11-triene 9-oxide anti-
The complexity answered, there is substantial amounts of side reaction, is unfavorable for the synthesis of 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.
The content of invention
Present invention solves the technical problem that being, allicin is in acetone/water system, and catabolite is mainly E/Z- Ah suddenly
Alkene.These catabolites result in the complexity that allicin is converted into 4,5,9-trithiadodeca-1,6,11-triene 9-oxide reaction, there is substantial amounts of side reaction, unfavorable
In the synthesis of 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.
To solve the above problems, the characteristics of present invention is directed to allicin cracking reaction, project is reacted using complex catalysis
Form, allicin is complexed with hydrophilic complex compound to improve the stabilization of allicin, and the solution complexing in reaction, such allicin is timely
Reaction generation 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, it is to avoid substantial amounts of side reaction occurs.
Technical scheme is as follows：
A kind of allicin synthesizes the process of 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, comprises the steps of：
(1) allinase is extracted：The garlic for adding allinase extract solution is obtained into garlic with colloid mill grinding to starch, centrifuged out
Clear liquid；Under the conditions of -5 DEG C~5 DEG C, ammonium sulfate is added in supernatant, is stirred in addition, the second clear liquid is then demultiplex out；
Polyethylene glycol is added into the second clear liquid again, is stirred in addition, centrifugation sub-argument goes out precipitation, weight is molten, and supernatant is obtained after centrifugation；
The present invention is specific according to the requirement of immobilised enzymes immobilization technology and industrial enzymes, sets up the enzyme purification of suitable large-scale application
Technique.Leaching liquor component in allinase purge process is investigated using enzyme activity yield, specific activity of enzyme as index, according to the zymetology of garlic allinase
Property, carries the garlic allinase in crude enzyme liquid from salting out method, the organic polymer precipitation method respectively；It is determined that most suitable ammonium sulfate concentrations,
PEG8000 concentration.
(2) allinase is purified：The supernatant ultrafiltration that step (1) is obtained, clear liquid is successively through the descending molecule of molecular weight
Milipore filter carries out 2-3 grades and is separated by filtration, and it is molecular weight 200000, final stage molecule milipore filter that the molecule milipore filter used is filtered first
Molecular weight be 15000-5000；Modern hyperfiltration technique is replaced into extraction and purification process of the dialysis applied to allinase.Ultrafiltration
Essentially consisted in technique according to allinase in crude enzyme liquid and the wherein size of foreign protein molecular weight, select one or more groups of molecular weight
Milipore filter, to reach the purpose for removing various foreign proteins.On the other hand, because enzyme is easily denatured under drastic conditions, in research
In, under investigating respectively using centrifugal pump, plunger pump, membrane pump as the separation condition of power, influence to enzyme activity selects to be applicable
In the pump of allinase ultra-filtration and separation.
(3) allinase immobilization：By dipotassium hydrogen phosphate/sodium, the aqueous solution soluble in water that is made into is stand-by respectively with calcium chloride respectively,
The allinase that step (2) is obtained again is added in calcium chloride water, and regulation pH is 5-9, after stirring, and adds phosphoric acid hydrogen two
The aqueous solution of potassium/sodium, the obtained precipitation i.e. allinase of immobilization；By the research to allinase function assessment, with enzyme adsorption rate, fixation
Change the indexs such as specific activity of enzyme, immobilised enzymes stability, it is determined that being adapted to the immobilization way of allinase.
(4) allicin is prepared：Under conditions of -5 DEG C~5 DEG C, pH are 4-6, the immobilization allinase that step (3) is obtained adds
Enter into alliin solution, solid-liquid ratio is 1:1-1:5, obtained product is extracted with ethanol, and the allicin being obtained by extraction is standby；Will
Immobilization allinase is assembled into bioreactor, and the influence to alliin conversion ratio such as reaction temperature, pH is investigated by orthogonal test,
To determine optimum reaction condition.
(5) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is synthesized：The beta-schardinger dextrin aqueous solution is configured, the allicin obtained with step (4) is mixed, suspended
Thing, then mixture heating response dries, pulverizes and sieves and obtains inclusion compound containing 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.
(6) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is purified：The 4,5,9-trithiadodeca-1,6,11-triene 9-oxide inclusion compound that step (5) is obtained is extracted with polar organic solvent, recycling design
Obtain 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.
Further, allinase extract solution is to contain complexing agent, antioxidant, buffer and glycerine in the step (1)
The aqueous solution.
Further, step (1) complexing agent is disodium ethylene diamine tetraacetate；Antioxidant is mercaprol；Buffering
Agent is phosphate.
Further, the addition of ammonium sulfate is 20%-30% in the step (1), and the addition of polyethylene glycol is
30%-50%.
Further, step (1) the centrifugal condition 3000-5000 × g, 30min.
Further, step (3) dipotassium hydrogen phosphate/sodium water solution concentration is 1M, calcium chloride water concentration
For 1M.
Further, the solid-liquid ratio of beta-schardinger dextrin and water is 1 in the beta-schardinger dextrin aqueous solution in the step (5):1-1:5,
30 DEG C~70 DEG C of reaction temperature.
Further, polar organic solvent is methanol, ethanol, acetone in the step (6), and it is 1 to extract feed liquid ratio:4-
1:6, extract hot 30 DEG C~90 DEG C of temperature.
The invention has the advantages that：
1st, allinase is fixed using enzyme immobilization technology, in bioreactor, catalysis alliin is converted into allicin, reacts
Selectivity is good, high catalytic efficiency, can obtain the allicin product of high-purity.
2nd, reacted using complex catalysis, it is to avoid a large amount of side reactions are produced, it is ensured that 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is in high yield.
Embodiment
To make the purpose, technical scheme and advantage of the embodiment of the present invention clearer, below in the embodiment of the present invention
Technical scheme is clearly and completely described, it is clear that described embodiment is a part of embodiment of the invention, rather than entirely
The embodiment in portion.Based on the embodiment in the present invention, those of ordinary skill in the art are not under the premise of creative work is made
The every other embodiment obtained, belongs to the scope of protection of the invention.
Embodiment 1：
A kind of allicin synthesizes the process of 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, comprises the steps of：
(1) allinase is extracted：The garlic for adding allinase extract solution is obtained into garlic with colloid mill grinding to starch, centrifuged out
Clear liquid；Under the conditions of 0 DEG C, ammonium sulfate is added in supernatant, is stirred in addition, the second clear liquid is then demultiplex out；Again to
Polyethylene glycol is added in two clear liquids, is stirred in addition, centrifugation sub-argument goes out precipitation, weight is molten, and supernatant is obtained after centrifugation；The present invention
According to the specific of the requirement of immobilised enzymes immobilization technology and industrial enzymes, the enzyme purification process of suitable large-scale application is set up.
Leaching liquor component in allinase purge process is investigated using enzyme activity yield, specific activity of enzyme as index, according to the zymologic property of garlic allinase,
The garlic allinase in crude enzyme liquid is carried from salting out method, the organic polymer precipitation method respectively；It is determined that most suitable ammonium sulfate concentrations,
PEG8000 concentration.Allinase extract solution is to contain the water-soluble of complexing agent, antioxidant, buffer and glycerine in the step (1)
Liquid；Complexing agent is disodium ethylene diamine tetraacetate；Antioxidant is mercaprol；Buffer is phosphate.Sulfuric acid in the step (1)
The addition of ammonium is 25%, and the addition of polyethylene glycol is 40%.Centrifugal condition 4000 × g, 30min.
(2) allinase is purified：The supernatant ultrafiltration that step (1) is obtained, clear liquid is successively through the descending molecule of molecular weight
Milipore filter carries out 2 grades and is separated by filtration, and it is molecular weight 200000 that the molecule milipore filter used is filtered first, final stage molecule milipore filter
Molecular weight is 10000；
(3) allinase immobilization：By dipotassium hydrogen phosphate/sodium, the aqueous solution soluble in water that is made into is stand-by respectively with calcium chloride respectively,
The allinase that step (2) is obtained again is added in calcium chloride water, and regulation pH is 7, after stirring, and adds phosphoric acid hydrogen two
The aqueous solution of potassium/sodium, the obtained precipitation i.e. allinase of immobilization；Step (3) dipotassium hydrogen phosphate/sodium water solution concentration is
1M, calcium chloride water concentration is 1M.
(4) allicin is prepared：Under conditions of 0 DEG C, pH is 5, the immobilization allinase that step (3) is obtained is added to garlic ammonia
In acid solution, solid-liquid ratio is 1:3, obtained product is extracted with ethanol, and the allicin being obtained by extraction is standby.
(5) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is synthesized：The beta-schardinger dextrin aqueous solution is configured, the allicin obtained with step (5) is mixed, suspended
Thing, then mixture heating response dries, pulverizes and sieves and obtains inclusion compound containing 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.Beta-schardinger dextrin in the step (5)
The solid-liquid ratio of beta-schardinger dextrin and water is 1 in the aqueous solution:3.
(6) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is purified：The inclusion compound containing 4,5,9-trithiadodeca-1,6,11-triene 9-oxide of step (5) is taken, by solid-liquid ratio 1:4 add ethanol, are heated to 60
1h is extracted in DEG C stirring, filtering, and filtrate decompression recycling design obtains 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, and content is 82.3%.
Embodiment 2：
A kind of allicin synthesizes the process of 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, comprises the steps of：
(1) allinase is extracted：The garlic for adding allinase extract solution is obtained into garlic with colloid mill grinding to starch, centrifuged out
Clear liquid；Under the conditions of -5 DEG C, ammonium sulfate is added in supernatant, is stirred in addition, the second clear liquid is then demultiplex out；Again to
Polyethylene glycol is added in two clear liquids, is stirred in addition, centrifugation sub-argument goes out precipitation, weight is molten, and supernatant is obtained after centrifugation；The present invention
According to the specific of the requirement of immobilised enzymes immobilization technology and industrial enzymes, the enzyme purification process of suitable large-scale application is set up.
Leaching liquor component in allinase purge process is investigated using enzyme activity yield, specific activity of enzyme as index, according to the zymologic property of garlic allinase,
The garlic allinase in crude enzyme liquid is carried from salting out method, the organic polymer precipitation method respectively；It is determined that most suitable ammonium sulfate concentrations,
PEG8000 concentration.Allinase extract solution is to contain the water-soluble of complexing agent, antioxidant, buffer and glycerine in the step (1)
Liquid；Complexing agent is disodium ethylene diamine tetraacetate；Antioxidant is mercaprol；Buffer is phosphate.Sulfuric acid in the step (1)
The addition of ammonium is 20%, and the addition of polyethylene glycol is 30%-.Centrifugal condition 5000 × g, 30min.
(2) allinase is purified：The supernatant ultrafiltration that step (1) is obtained, clear liquid is successively through the descending molecule of molecular weight
Milipore filter carries out 2 grades and is separated by filtration, and it is molecular weight 200000 that the molecule milipore filter used is filtered first, final stage molecule milipore filter
Molecular weight is 15000.
(3) allinase immobilization：By dipotassium hydrogen phosphate/sodium, the aqueous solution soluble in water that is made into is stand-by respectively with calcium chloride respectively,
The allinase that step (2) is obtained again is added in calcium chloride water, and regulation pH is 5, after stirring, and adds phosphoric acid hydrogen two
The aqueous solution of potassium/sodium, the obtained precipitation i.e. allinase of immobilization.Step (3) dipotassium hydrogen phosphate/sodium water solution concentration
For 1M, calcium chloride water concentration is 1M.
(4) allicin is prepared：Under conditions of 5 DEG C, pH is 4, the immobilization allinase that step (3) is obtained is added to garlic ammonia
In acid solution, solid-liquid ratio is 1:5, obtained product is extracted with ethanol, and the allicin being obtained by extraction is standby.
(5) configure the beta-schardinger dextrin aqueous solution, the allicin obtained with step (5) mixes, obtain suspension, by mixture plus
Thermal response, then dries, pulverizes and sieves and obtain inclusion compound containing 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.β-ring in the beta-schardinger dextrin aqueous solution in the step (5)
The solid-liquid ratio of dextrin and water is 1:1.
(6) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is purified：The inclusion compound containing 4,5,9-trithiadodeca-1,6,11-triene 9-oxide of step (5) is taken, by solid-liquid ratio 1:5 add ethanol, are heated to 45
1h is extracted in DEG C stirring, filtering, and filtrate decompression recycling design obtains 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, and content is 78.8%.
Embodiment 3：
A kind of allicin synthesizes the process of 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, comprises the steps of：
(1) allinase is extracted：The garlic for adding allinase extract solution is obtained into garlic with colloid mill grinding to starch, centrifuged out
Clear liquid；Under the conditions of 5 DEG C, ammonium sulfate is added in supernatant, is stirred in addition, the second clear liquid is then demultiplex out；Again to
Polyethylene glycol is added in two clear liquids, is stirred in addition, centrifugation sub-argument goes out precipitation, weight is molten, and supernatant is obtained after centrifugation；The present invention
According to the specific of the requirement of immobilised enzymes immobilization technology and industrial enzymes, the enzyme purification process of suitable large-scale application is set up.
Leaching liquor component in allinase purge process is investigated using enzyme activity yield, specific activity of enzyme as index, according to the zymologic property of garlic allinase,
The garlic allinase in crude enzyme liquid is carried from salting out method, the organic polymer precipitation method respectively；It is determined that most suitable ammonium sulfate concentrations,
PEG8000 concentration.Allinase extract solution is to contain the water-soluble of complexing agent, antioxidant, buffer and glycerine in the step (1)
Liquid；Complexing agent is disodium ethylene diamine tetraacetate；Antioxidant is mercaprol；Buffer is phosphate.Sulfuric acid in the step (1)
The addition of ammonium is 30%, and the addition of polyethylene glycol is 50%.Centrifugal condition 3000 × g, 30min.
(2) allinase is purified：The supernatant ultrafiltration that step (1) is obtained, clear liquid is successively through the descending molecule of molecular weight
Milipore filter carries out 2 grades and is separated by filtration, and it is molecular weight 200000 that the molecule milipore filter used is filtered first, final stage molecule milipore filter
Molecular weight is 15000.
(3) allinase immobilization：By dipotassium hydrogen phosphate/sodium, the aqueous solution soluble in water that is made into is stand-by respectively with calcium chloride respectively,
The allinase that step (2) is obtained again is added in calcium chloride water, and regulation pH is 9, after stirring, and adds phosphoric acid hydrogen two
The aqueous solution of potassium/sodium, the obtained precipitation i.e. allinase of immobilization.Step (3) dipotassium hydrogen phosphate/sodium water solution concentration
For 1M, calcium chloride water concentration is 1M.
(4) allicin is prepared：Under conditions of -5 DEG C, pH is 6, the immobilization allinase that step (3) is obtained is added to garlic
In propylhomoserin solution, solid-liquid ratio is 1:5, obtained product is extracted with ethanol, and the allicin being obtained by extraction is standby.
(5) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is synthesized：The allicin obtained with step (5) is mixed, and obtains suspension, by mixture heating response,
Then dry, pulverize and sieve and obtain inclusion compound containing 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.Beta-schardinger dextrin and water in the beta-schardinger dextrin aqueous solution in the step (5)
Solid-liquid ratio be 1:1.
(6) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is purified：The inclusion compound containing 4,5,9-trithiadodeca-1,6,11-triene 9-oxide of step (5) is taken, by solid-liquid ratio 1:3 add ethanol, are heated to 30
1h is extracted in DEG C stirring, filtering, and filtrate decompression recycling design obtains 4,5,9-trithiadodeca-1,6,11-triene 9-oxide, and content is 76.4%.
Claims (8)
1. a kind of allicin synthesizes the process of ajoene, it is characterised in that comprise the steps of：
(1) allinase is extracted：The garlic for adding allinase extract solution is obtained into garlic with colloid mill grinding to starch, supernatant is centrifuged out
Liquid；Under the conditions of -5 DEG C~5 DEG C, ammonium sulfate is added in supernatant, is stirred in addition, the second clear liquid is then demultiplex out；Again
Polyethylene glycol is added into the second clear liquid, is stirred in addition, centrifugation sub-argument goes out precipitation, weight is molten, and supernatant is obtained after centrifugation；
(2) allinase is purified：The supernatant ultrafiltration that step (1) is obtained, clear liquid is successively through the descending molecule ultrafiltration of molecular weight
Film carries out 2-3 grades and is separated by filtration, and it is molecular weight 200000, point of final stage molecule milipore filter that the molecule milipore filter used is filtered first
Son amount is 15000-5000；
(3) allinase immobilization：By dipotassium hydrogen phosphate/sodium, the aqueous solution soluble in water that is made into is stand-by respectively with calcium chloride respectively, then will
The allinase that step (2) is obtained is added in calcium chloride water, and regulation pH is 5-9, after stirring, and addition dipotassium hydrogen phosphate/
The aqueous solution of sodium, the obtained precipitation i.e. allinase of immobilization；
(4) allicin is prepared：Under conditions of -5 DEG C~5 DEG C, pH are 4-6, the immobilization allinase that step (3) is obtained is added to
In alliin solution, solid-liquid ratio is 1:1-1:5, obtained product is extracted with ethanol, and the allicin being obtained by extraction is standby；
(5) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is synthesized：The beta-schardinger dextrin aqueous solution is configured, the allicin obtained with step (5) is mixed, and obtains suspension, will
Mixture heating response, then dries, pulverizes and sieves and obtain inclusion compound containing 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.
(6) 4,5,9-trithiadodeca-1,6,11-triene 9-oxide is purified：The 4,5,9-trithiadodeca-1,6,11-triene 9-oxide inclusion compound that step (5) is obtained is extracted with polar organic solvent, recycling design obtain Ah
Alkene suddenly.
2. the preparation method of the process of allicin synthesis ajoene as claimed in claim 1, it is characterised in that：The step
Suddenly allinase extract solution is the aqueous solution containing complexing agent, antioxidant, buffer and glycerine in (1).
3. the preparation method of the process of allicin synthesis ajoene as claimed in claim 2, it is characterised in that：The step
Suddenly (1) complexing agent is disodium ethylene diamine tetraacetate；Antioxidant is mercaprol；Buffer is phosphate.
4. the preparation method of the process of allicin synthesis ajoene as claimed in claim 1, it is characterised in that：The step
Suddenly the addition of ammonium sulfate is 20%-30% in (1), and the addition of polyethylene glycol is 30%-50%.
5. the preparation method of the process of allicin synthesis ajoene as claimed in claim 1, it is characterised in that：The step
Suddenly (1) centrifugal condition 3000-5000 × g, 30min.
6. the preparation method of the process of allicin synthesis ajoene as claimed in claim 1, it is characterised in that：The step
Suddenly (3) dipotassium hydrogen phosphate/sodium water solution concentration is 1M, and calcium chloride water concentration is 1M.
7. the preparation method of the process of allicin synthesis ajoene as claimed in claim 1, it is characterised in that：The step
Suddenly the solid-liquid ratio of beta-schardinger dextrin and water is 1 in the beta-schardinger dextrin aqueous solution in (5):1-1:5.
8. the preparation method of the process of allicin synthesis ajoene as claimed in claim 1, it is characterised in that：The step
Suddenly polar organic solvent is methanol, ethanol, acetone in (6).
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108795749A (en) * | 2018-08-23 | 2018-11-13 | 五峰赤诚生物科技股份有限公司 | A kind of devices and methods therefor of immobilized tannase production gallic acid |
| IT201800003394A1 (en) * | 2018-03-09 | 2019-09-09 | Piante Acqua Natura Srl P A N | LYMPH-COMPATIBLE FORMULATION BASED ON ALLICIN |
| CN111004161A (en) * | 2019-12-31 | 2020-04-14 | 河南大学 | Method for enhancing stability of allicin |
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| IT201800003394A1 (en) * | 2018-03-09 | 2019-09-09 | Piante Acqua Natura Srl P A N | LYMPH-COMPATIBLE FORMULATION BASED ON ALLICIN |
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| CN111004161A (en) * | 2019-12-31 | 2020-04-14 | 河南大学 | Method for enhancing stability of allicin |
| CN114847481A (en) * | 2022-06-06 | 2022-08-05 | 齐鲁工业大学 | Application of ajoene and ajoene nutrition powder for inhibiting helicobacter pylori |
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