CN103266154A - Biological transformation method for preparing high-activity theasaponin - Google Patents
Biological transformation method for preparing high-activity theasaponin Download PDFInfo
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Abstract
The invention provides a biological transformation method for preparing high-activity theasaponin and belongs to the technical field of biochemical engineering. The biological transformation method comprises the following technological processes of: purifying crude theasaponin by AB-8 macroporous resin, preparing a theasaponin enzymolysis substrate, extracting enzyme liquid, carrying out enzymolysis on the theasaponin and separating enzymolysis components. According to the biological transformation method, firstly sasanguasaponin hydrolytic enzymes are extracted from aspergillus oryzae and aspergillus niger strains, and then sasanguasaponin is hydrolyzed by an enzymic method, experimental conditions are mild, products are easy to control, the pollutant discharge is reduced, and therefore, the biological transformation method is a new green manufacturing technology. Compared with the antioxidant activity of the original sasanguasaponin, the antioxidant activity of the obtained theasaponin is greatly increased. Oil-tea cakes mainly contain crude protein, saccharides, oil, the theasaponin and the like and have very high comprehensive utilization value. Therefore, the oil-tea cakes are used for extracting the theasaponin which is subjected to the enzymolysis, so that the theasaponin with low sugar chain and high activity is obtained. The biological transformation method has prominent economic benefits and social benefits in the research, development and application of the comprehensive utilization of the oil-tea cakes.
Description
Technical field
The present invention relates to a kind of bioconversion method for preparing high reactivity tea saponin, belong to the biochemical engineering technical field.
Background technology
The tea saponin is a kind of pentacyclic triterpene glycoside compounds that extracts from plant of theaceae, extensively is present in the various teas plants, and along with the development of modern separate analytical technique, people have carried out deep research to the structure of tea saponin.The tea saponin is because its special chemical structure, has good activity at aspects such as emulsification, dispersion, moistening, foaming, steady bubble, decontaminations, is a kind of natural surface active agent of excellent property: be widely used in foodstuff additive, sterilant.Many-sides such as that the tea saponin bioactive shows is antibiotic, anti-inflammatory, antiulcer agent, anti-oxidant, reducing blood-fat.
At present, people mainly concentrate on tissue distribution and the physiologically active aspect of saponin to the research of tea saponin, and the separation-extraction technology of saponin is also possessed some special knowledge.But the bioactivity research report that improves the tea saponin by the change structure is still rare.And the hydrolysis of tea saponin adopted acid, alkaline process more, condition is violent and seriously polluted.Sasanguasaponin is carried out bio-transformation, its active general tea saponin is increased, for the enzyme solution of tea saponin, yet there are no report in the data at home and abroad.
China is that world's oil tea output is the highest, the cultivated area maximum, the country that kind is the abundantest, the oil tea cake that is left after 750,000 tons of oil expressions is arranged national every year, the utilization ratio of domestic resource only is 10%, because oil tea cake bitter can not directly be used as feed, the peasant in the place of production often is used as fertilizer or soil agricultural chemicals processed to the oil tea cake, and economic benefit is extremely low.Mainly contain crude protein, carbohydrate, grease, tea saponin etc. in the oil tea cake, have very high comprehensive utilization value.Thereby, strengthen using significant to the research and development of oil tea cake comprehensive utilization.
Summary of the invention
Various disadvantages at hydrolysis tea saponin; the present invention seeks to propose a kind of biotransformation method enzymolysis tea saponin and prepare the sasanguasaponin with low-sugar-chain high-activity; its chemical name is 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A; molecular weight is 967, and molecular formula is C
49H
75O
19
The technical solution used in the present invention is: a kind of bioconversion method for preparing high reactivity tea saponin comprises the steps:
(1) utilize the AB-8 macroporous resin to the purifying of thick tea saponin:
The thick tea saponin mass concentration that to extract from the oil tea cake is 70～95% alcohol solution dippings, filter clear liquid, 50～75 ℃ of decompressions steam ethanol, obtain the clear liquid of sasanguasaponin, AB-8 macroporous resin column on the clear liquid, leave standstill and make abundant absorption, wash with 1.5BV/h speed with deionized water, the 0.1%NaOH aqueous solution successively, be washed till washings pH=7-8 with deionized water again, use the ethanolic soln wash-out, collect ethanol eluate, 50～75 ℃ are evaporated to driedly, obtain tea saponin behind the purifying;
(2) preparation of tea saponin enzymolysis substrate:
Tea saponin behind the purifying is put into china bowl, add methyl alcohol and make its dissolving, and tea saponin concentration is 3-8mg/mL, adding quality in this solution is tea saponin quality 5-10 100～200 order silica gel doubly, stir, put and be heated to 65-80 ℃ on the water-bath, treat to make sample glue after solvent evaporates fully;
Adding quality in chromatography column is tea saponin quality 30-300 300～400 purpose silica gel doubly, keeps the upper surface level, vacuumizes to make it fine and closely woven even, reinstalls dry good sample glue;
After silicagel column installed, earlier with pure chloroform through post, chloroform: methyl alcohol=9:1,8:2,7:3,6:4,5:5 gradient elution tea saponin were by volume successively collected elutriant respectively, and the product of collecting are analyzed again, obtain tea saponin enzymolysis substrate tea saponin A
5, its chemical name is 3-oxygen-β-D-galactopyranose base-(1-2) [β-D-glucopyranosyl-(1-2)-α-L-arabopyranose base (1-3)] beta d glucopyranosiduronic acid base-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A;
(3) extraction of enzyme liquid:
Dregs of beans is blended, cross 20 mesh sieves, take by weighing dregs of beans and wheat bran respectively, the weight ratio that makes the two is 1:3, put into Erlenmeyer flask, the adding tap water makes moistening, and every g mixture adds the 1mL tap water, stir, sterilized 15～20 minutes down at 121 ℃, after cooling, insert aspergillus tubigensis, cultivated 2～5 days down in 25～40 ℃, after waiting to grow a large amount of spores, in substratum, add 0.02mol/L, the pH value is 5.0 NaAc-HAc damping fluid, and the damping fluid volume is 5 times of aforementioned tap water volume, soaked 1～2 hour, use filtered through gauze, filtrate under 9000 rev/mins of rotating speeds centrifugal 15 minutes is removed wherein partial impurities, namely obtain enzyme liquid, slowly add dehydrated alcohol in enzyme liquid, making alcohol concn is 70%～75%, spends the night in 2～8 ℃ of placements, saltout, enzyme liquid after saltouing under 8000-10000 rev/min of rotating speed centrifugal 10-20 minute will precipitate with the above-mentioned damping fluid of 1-3mL and wash, place dialysis tubing with acetate buffer solution in 2～8 ℃ of dialysis 24-48 hour, centrifugal more afterwards, the gained supernatant liquor is enzyme liquid;
(4) enzymolysis of tea saponin:
The tea saponin A that the step (2) of 0.5～5.0mg/mL of equal volume is obtained
5The enzyme liquid that solution and step (3) obtain is evenly mixed, and making the pH value is 4.0～6.0,40～55 ℃ of reactions 10～20 hours, during reaction terminating, adds 2 times of volume tea saponin A in reaction system
5The propyl carbinol of solution rocks repeatedly, behind the standing demix, takes out upper strata liquid, with the propyl carbinol evaporate to dryness, namely gets enzymolysis product;
(5) separation of enzymolysis component:
Adopt the thick preparation of silica gel chromatoplate of 1mm, method and requirement according to thin-layer chromatography, the enzymolysis product that separating step (4) obtains, enzymolysis product becomes 0.5～5.0mg/mL solution to carry out point sample with dissolve with methanol, and developping agent is: chloroform: methyl alcohol: water=7:3:0.5, determine that the position of target product on chromatoplate is Rf=0.67, scrape the silica gel of this position with blade, with 1-5mL methyl alcohol it is dissolved again, filter, obtain the saponin product A behind the enzymolysis after filtrate is concentrated
6, its chemical name is 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A.
Described aspergillus tubigensis is chosen a kind of from black-koji mould sp.48, black-koji mould sp.92, black-koji mould sp.848, black-koji mould sp.3112, black-koji mould sp.3111, black-koji mould sp.uv-11, aspergillus oryzae sp.39, aspergillus oryzae sp.42, aspergillus oryzae sp.00, aspergillus oryzae sp.3102.
Above-mentioned technical scheme is a kind of bioconversion method for preparing 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A with enzymolysis tea saponin.The bioconversion reaction formula is as follows: A5 has cut away β-D-glucopyranosyl-(1-2)-α-L-arabopyranose base behind enzymolysis, obtain tea saponin A6.
The invention has the beneficial effects as follows: the bioconversion method of this preparation high reactivity tea saponin adopts the AB-8 macroporous resin to purifying, preparation tea saponin enzymolysis substrate, extraction enzyme liquid, the enzymolysis tea saponin and the technological process of separating the enzymolysis component of thick tea saponin, from aspergillus oryzae and Aspergillus niger strain, extract the sasanguasaponin lytic enzyme first, by the enzymatic hydrolysis sasanguasaponin, experiment condition gentleness, product are easy to control, reduce disposal of pollutants, are a kind of green manufacturing novel procesies.By gained tea saponin A6 and former oil tea saponin A5 are removed 1,1-phenylbenzene-2-trinitrophenyl-hydrazine free radical activity test relatively, find that the more former oil tea saponin of gained tea saponin anti-oxidant activity improves a lot.Mainly contain crude protein, carbohydrate, grease, tea saponin etc. in the oil tea cake, have very high comprehensive utilization value.Thereby, utilizing the oil tea cake to extract the tea saponin, and it is carried out enzymolysis, and then obtain the tea saponin of low-sugar-chain high-activity, this research and development to the comprehensive utilization of oil tea cake is used and will be produced remarkable economic efficiency and social benefit.
Description of drawings
Fig. 1 is tea saponin A
5The mass spectrum of (molecular weight is 1262).Owing to be negative ion mode, the molecular ion peak that obtains and related fragment peak are respectively:
M/z=1261 is [M-H]
-, m/z=966 is [M-H-C
11H
19O
9]
-, m/z=803 is [M-H-C
11H
19O
9-C
6H
11O
5]
-, wherein, C
11H
19O
9Be the glycosyl that a five-carbon sugar links to each other with a hexose, be glucopyranosyl and arabopyranose base; C
6H
11O
5Be a hexose base, be the galactopyranose base.These features and A
5Structure be consistent.
Fig. 2 is tea saponin A
6The mass spectrum of (molecular weight is 967).Owing to be negative ion mode, the molecular ion peak that obtains and related fragment peak are respectively:
M/z=966 is [M-H]
-, m/z=803 is [M-H-C
6H
11O
5]
-, wherein, C
6H
11O
5Be a hexose base, should be the galactopyranose base.These features and A
6Structure be consistent.
Fig. 3 is tea saponin A
5And A
6The anti-oxidant activity comparison diagram.By finding out among the figure, under 4 reduced concentrations, tea saponin A
6Clearance rate to 1,1-phenylbenzene-2-trinitrophenyl-hydrazine (DPPH) free radical all is higher than tea saponin A
5To the clearance rate of DPPH free radical, for example, when concentration is 1.2mg/mL, tea saponin A
6To the clearance rate of DPPH free radical near 70%, and the tea saponin A of same concentrations
5To the clearance rate of DPPH free radical less than 50%.The tea saponin anti-oxidant activity that this explanation present method obtains improves a lot.
Remove the mensuration of DPPH free radical activity: in the test tube (10mL) of the absolute methanol solution that 5mL100 μ mol/L DPPH is housed.The saponin solution that adds people 5mL different concns, making cumulative volume is 10mL, places 30min in the dark of concussion back.Be blank with the anhydrous methanol, in wavelength 525nm place its absorbancy of mensuration.Each sample is made 3 parallel samples, averages.Calculate its clearance rate.
Clearance rate (%)=(A
0-A)/A
0* 100
In the formula, A
0-blank absorbency value (add DPPH, do not add sample);
A-525nm place adds the absorbance of the DPPH of sample.
Embodiment
The invention will be further elaborated below in conjunction with embodiment.
Embodiment 1
(1) utilize the AB-8 macroporous resin to the purifying of thick tea saponin:
The thick tea saponin mass concentration that to extract from the oil tea cake is 70% alcohol solution dipping, filter clear liquid, 50 ℃ of decompressions steam ethanol, obtain the clear liquid of sasanguasaponin, AB-8 macroporous resin column on the clear liquid, leave standstill and make abundant absorption, wash with 1.5BV/h speed with deionized water, the 0.1%NaOH aqueous solution successively, be washed till washings pH=7 with deionized water again, use the ethanolic soln wash-out, collect ethanol eluate, 50 ℃ are evaporated to driedly, obtain tea saponin behind the purifying;
(2) preparation of tea saponin enzymolysis substrate:
Tea saponin behind the 0.3g purifying is put into china bowl, add 100mL methyl alcohol and make its dissolving, add 100～200 order silica gel of 3g in this solution, stir, put heating (65 ℃) on the water-bath, treat to make sample glue after solvent evaporates fully;
In chromatography column, add 300～400 order silica gel of 50g, keep the upper surface level, vacuumize and make it fine and closely woven even, reinstall dry good sample glue;
After silicagel column installed, earlier with pure chloroform through post, chloroform: methyl alcohol=9:1,8:2,7:3,6:4,5:5 gradient elution tea saponin were by volume successively collected elutriant respectively, and the product of collecting are analyzed again, obtain tea saponin enzymolysis substrate-tea saponin A
5, its chemical name is 3-oxygen-β-D-galactopyranose base-(1-2) [β-D-glucopyranosyl-(1-2)-α-L-arabopyranose base (1-3)] beta d glucopyranosiduronic acid base-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A;
(3) extraction of enzyme liquid:
Take by weighing dregs of beans (20 orders blend) 5g, wheat bran 15g puts into the 250mL Erlenmeyer flask, adds the 20mL tap water, stirs, and makes substratum all moistening and loose, does not have caking.Sterilized 20 minutes down at 121 ℃.After cooling, insert aspergillus niger sp.48 bacterium, cultivate couple of days under 30 ℃, rock once every several hrs the centre, makes it keep loose, is conducive to bacterial classification and evenly grows.Wait to expand and join bacterial classification and grow a large amount of spores, add 100mL0.02mol/L pH value in the substratum and be 5.0 NaAc-HAc damping fluid, soaked 2 hours, use filtered through gauze, filtrate under 9000 rev/mins of rotating speeds centrifugal 15 minutes is removed wherein partial impurities, namely obtains crude enzyme liquid.Slowly add the 175mL dehydrated alcohol in crude enzyme liquid, making its concentration is 70%.Spend the night 4 ℃ of placements then, saltout.Enzyme liquid after saltouing under 9000 rev/mins of rotating speeds centrifugal 15 minutes will precipitate with the above-mentioned damping fluid of 1mL and wash, place dialysis tubing in 4 ℃ with acetate buffer solution dialysis 24 hours, 5 hours exchange buffering liquid of period interval is once.Afterwards, centrifugal again, the gained supernatant liquor is enzyme liquid.
(4) enzymolysis of tea saponin:
Tea saponin A with 1mL5mg/mL
5Solution and 1mL enzyme liquid are mixed, and evenly making pH value is 6.0, in 50 ℃ of reactions 16 hours, during reaction terminating, adds the 2mL propyl carbinol in the reaction system and rocks repeatedly, and behind the standing demix, taking-up upper strata liquid with the propyl carbinol evaporate to dryness, namely gets enzymolysis product;
(5) separation of enzymolysis component:
Adopt the thick preparation of silica gel chromatoplate of 1mm, according to method and the requirement of thin-layer chromatography, the enzymolysis product that separating step (4) obtains.Enzymolysis product becomes 1mg/mL solution to carry out point sample with dissolve with methanol; developping agent is: chloroform: methyl alcohol: water=7:3:0.5; determine the position (Rf=0.67) of target product on chromatoplate; scrape the silica gel of this position with blade; with 2mL methyl alcohol it is dissolved again; filter, can obtain saponin product 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid the base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A behind the enzymolysis after filtrate is concentrated, note is made A
6
Embodiment 2
Experimental technique is with embodiment 1, and the bacterial classification of using in the time of just will extracting enzyme liquid is changed to aspergillus niger sp.848 bacterium, obtains 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A.
Embodiment 3
Experimental technique is with embodiment 1, and the bacterial classification of using in the time of just will extracting enzyme liquid is changed to aspergillus oryzae sp.39 bacterium, obtains 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A.
Embodiment 4
Experimental technique is with embodiment 1, and just the pH value with enzyme digestion reaction is adjusted to 5.0, obtains 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A.
Embodiment 5
Experimental technique just shortens to 12 hours with the enzyme digestion reaction time with embodiment 1, obtains 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A.
Embodiment 6
Experimental technique is with embodiment 1, just with enzyme digestion reaction substrate tea saponin A
5Concentration become 2mg/mL, obtain 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A.
Claims (2)
1. a bioconversion method for preparing high reactivity tea saponin is characterized in that, comprises the steps:
(1) utilize the AB-8 macroporous resin to the purifying of thick tea saponin:
The thick tea saponin mass concentration that to extract from the oil tea cake is 70～95% alcohol solution dippings, filter clear liquid, 50～75 ℃ of decompressions steam ethanol, obtain the clear liquid of sasanguasaponin, AB-8 macroporous resin column on the clear liquid, leave standstill and make abundant absorption, wash with 1.5BV/h speed with deionized water, the 0.1%NaOH aqueous solution successively, be washed till washings pH=7-8 with deionized water again, use the ethanolic soln wash-out, collect ethanol eluate, 50～75 ℃ are evaporated to driedly, obtain tea saponin behind the purifying;
(2) preparation of tea saponin enzymolysis substrate:
Tea saponin behind the purifying is put into china bowl, add methyl alcohol and make its dissolving, and tea saponin concentration is 3-8mg/mL, adding quality in this solution is tea saponin quality 5-10 100～200 order silica gel doubly, stir, put and be heated to 65-80 ℃ on the water-bath, treat to make sample glue after solvent evaporates fully;
Adding quality in chromatography column is tea saponin quality 30-300 300～400 purpose silica gel doubly, keeps the upper surface level, vacuumizes to make it fine and closely woven even, reinstalls dry good sample glue;
After silicagel column installed, earlier with pure chloroform through post, chloroform: methyl alcohol=9:1,8:2,7:3,6:4,5:5 gradient elution tea saponin were by volume successively collected elutriant respectively, and the product of collecting are analyzed again, obtain tea saponin enzymolysis substrate-tea saponin A
5, its chemical name is 3-oxygen-β-D-galactopyranose base-(1-2) [β-D-glucopyranosyl-(1-2)-α-L-arabopyranose base (1-3)] beta d glucopyranosiduronic acid base-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A;
(3) extraction of enzyme liquid:
Dregs of beans is blended, cross 20 mesh sieves, take by weighing dregs of beans and wheat bran respectively, the weight ratio that makes the two is 1:3, put into Erlenmeyer flask, the adding tap water makes moistening, and every g mixture adds the 1mL tap water, stir, sterilized 15～20 minutes down at 121 ℃, after cooling, insert aspergillus tubigensis, cultivated 2～5 days down in 25～40 ℃, after waiting to grow a large amount of spores, in substratum, add 0.02mol/L, the pH value is 5.0 NaAc-HAc damping fluid, and the damping fluid volume is 5 times of aforementioned tap water volume, soaked 1～2 hour, use filtered through gauze, filtrate under 9000 rev/mins of rotating speeds centrifugal 15 minutes is removed wherein partial impurities, namely obtain enzyme liquid, slowly add dehydrated alcohol in enzyme liquid, making alcohol concn is 70%～75%, spends the night in 2～8 ℃ of placements, saltout, enzyme liquid after saltouing under 8000-10000 rev/min of rotating speed centrifugal 10-20 minute will precipitate with the above-mentioned damping fluid of 1-3mL and wash, place dialysis tubing with acetate buffer solution in 2～8 ℃ of dialysis 24-48 hour, centrifugal more afterwards, the gained supernatant liquor is enzyme liquid;
(4) enzymolysis of tea saponin:
The tea saponin A that the step (2) of 0.5～5.0mg/mL of equal volume is obtained
5The enzyme liquid that solution and step (3) obtain is evenly mixed, and making the pH value is 4.0～6.0,40～55 ℃ of reactions 10～20 hours, during reaction terminating, adds 2 times of volume tea saponin A in reaction system
5The propyl carbinol of solution rocks repeatedly, behind the standing demix, takes out upper strata liquid, with the propyl carbinol evaporate to dryness, namely gets enzymolysis product;
(5) separation of enzymolysis component:
Adopt the thick preparation of silica gel chromatoplate of 1mm, method and requirement according to thin-layer chromatography, the enzymolysis product that separating step (4) obtains, enzymolysis product becomes 0.5～5.0mg/mL solution to carry out point sample with dissolve with methanol, and developping agent is: chloroform: methyl alcohol: water=7:3:0.5, determine that the position of target product on chromatoplate is Rf=0.67, scrape the silica gel of this position with blade, with 1-5mL methyl alcohol it is dissolved again, filter, obtain the saponin product A behind the enzymolysis after filtrate is concentrated
6, its chemical name is 3-oxygen-[β-D-galactopyranose base-(1-2)-beta d glucopyranosiduronic acid base]-21-oxygen-Radix Angelicae Sinensis acidic group-28-oxy-acetyl-theasapogenol A.
2. the bioconversion method of preparation high reactivity tea saponin according to claim 1, it is characterized in that: described aspergillus tubigensis is chosen a kind of from black-koji mould sp.48, black-koji mould sp.92, black-koji mould sp.848, black-koji mould sp.3112, black-koji mould sp.3111, black-koji mould sp.uv-11, aspergillus oryzae sp.39, aspergillus oryzae sp.42, aspergillus oryzae sp.00, aspergillus oryzae sp.3102.
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| CN104496762A (en) * | 2015-01-12 | 2015-04-08 | 中南林业科技大学 | Method for separating two bibenzyl compounds from ordinary oil tea camellia |
| CN107530258A (en) * | 2015-03-31 | 2018-01-02 | 株式会社爱茉莉太平洋 | For promoting hair growth or hair reparation and composition for anti-inflammatory |
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Application publication date: 20130828 |