CN109082452A - A kind of method of liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment - Google Patents
A kind of method of liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment Download PDFInfo
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- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
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Abstract
A kind of method of liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment, the three-phase system is by gross mass by the ethyl alcohol of 15-30wt.%, the ammonium sulfate of 15-25wt.%, the water of the mulberry juice of 5-20wt.%, 2-10wt.% immobilization alpha-L-Rhamnosidase (15.73 ± 0.03U/mg of enzyme activity) and surplus forms.Under conditions of pH is 3.5-5.5, temperature is 20-50 DEG C, the reaction time is 1-3h, extraction and separation mulberry red pigment.Utilize the corn flower -3-O- rutinoside (C in immobilization alpha-L-Rhamnosidase catalysis mulberry red pigment3R), specific cleavage rhamnose glycosidic bond, orientation are converted into C-3-G (C3G), the C of high concentration is prepared3G.Generating process is environmentally friendly, pollution-free, and enzyme is reusable, at low cost, and the rate of recovery is high, realizes the enrichment of one-component, and the water solubility of product is good with tinctorial property, has boundless market prospects.
Description
Technical field
The invention belongs to biological chemical fields, and in particular to a kind of liquid-liquid-solid system enzymatic hydrolysis-extraction and separation mulberry
The method of mulberry haematochrome
Background technique
Mulberry fruit (Mulberry fruit) also known as sorosis are the fruit of Moraceae deciduous tree mulberry tree (Morus alba L.),
Annual 4-6 month is mature.1993, health ministry was just classified as mulberry fruit in one of the agricultural product of " being both food and drug ".
Edible mulberry fruit can enhance the weight of immune organ, enhance nonspecific immunity function and humoral immune function, have to cell mutation
Prevention effect also has the function of the virus such as resistance of hepatitis B and AIDS (Journal of Nutritional
Biochemistry,2015,26(8):860-867).Mulberry fruit is rich in haematochrome, is China's official approval use 48 kinds natural
One of pigment.Mulberry red pigment category anthocyanin type components are that fruit and vegetable food is presented from red to blue material base, have suppression
Platelet aggregation processed, pre- preventing thrombosis, heart disease anticancer, the effects of delaying senescence, are widely used in bakings, drink, cosmetics, gently
The industries such as work (Carpathian Journal of Food Science&Technology, 2016,8 (1): 169-174).Cause
This, mulberry red pigment is just becoming the irreplaceable fresh fruit pigment of other fruits, and market application prospect is wide.
Mulberry red pigment contains C-3-G (Cyanidin-3-O-glucoside, C3G), corn flower-
3-O- rutinoside (Cyanidin 3-rutinoside, C3R), corn flower -3-O- galactoside and corn flower -7- glucose
The ingredients such as four kinds of anthocyanin such as glycosides and a small amount of pelargonidin, delphinidin (Cancer Letters, 2006,235 (2):
248-59).Wherein, C3G is the main component of mulberry red pigment, accounts for about the 60% of total amount, and C3R accounts for about 30% (Food of total amount
Chemistry,2015,171(171):128-136).Studies have shown that C3G can enhance metabolism, inhibit weight gain, improve
Body lipid accumulation (Molecular Nutrition&Food Research, 2017)；There is protective effect to liver, it can be with
Hepar damnification (Journal of Functional Foods, 2017,37:16-24) caused by alleviation is drunk；It can induce mammary gland
Cancer cell-apoptosis is potential anticancer drug active constituent (Anti-cancer agents in medicinal
chemistry,2017,17(999)).Therefore, it is based on C3G has above-mentioned many bioactivity, it is necessary to further increase C3G exists
Content in mulberry red pigment.According to glycosidase directionally hydrolyzing C3The rhamnopyranosyl of R, makes C3R is converted into C3Mulberry fruit can be improved in G
C in haematochrome3The content of G makes its content close to even more than 90%.
Currently, reported mulberry red pigment extracting process mainly has solvent extraction method, microwave extraction method, macropore tree
Rouge method, aqueous two-phase system etc..Such as: solvent extraction method (CN101531825), the citric acid water for the use of weight ratio being 1.5-5 ‰
The mulberry fruit 30-180min that solution impregnates crushing at 30-50 DEG C obtains extracting solution, and through filtering, absorption, elution, concentration, mulberry is made
Mulberry haematochrome, recovery rate is up to 89%；Microwave radiation assisted extraction method (CN101100557) adopts the mulberry fruit residue after squeezing the juice
With microwave reinforced extraction, microwave power is 227.5-650W, to extract solid-liquid ratio be 1: 5-1: 25, extractant concentration of alcohol is 0-
60%, under the conditions of microwave treatment time is 2-10min etc., the pigment concentration of extraction is up to 98.7mg/L；Flavonoids by Macroporous Adsorption Resin
(CN105062125A), with 80% ethyl alcohol: 0.1%HCl (1:1, v/v) is extractant, liquid-to-solid ratio 1:15, ultrasonic 30min, weight
Again twice, using macroporous absorbent resin D101 2.7g/g adsorbing separation, the yield for obtaining Application of Mulberry Anthocyanins is 5.6mg/g.It is above-mentioned
Extracting process has good effect of extracting to mulberry red pigment, but only can be realized its extraction, and can not achieve mulberry fruit red
The specific enrichment of plain ingredient.In recent years, aqueous two phase extraction technique due to high extractability, mild condition, it is low in cost and
The potentiality such as purifying and the concentration of required product (Food Chemistry, 2011,129 (2): 443- are able to achieve in single step
453), gradually it is applied to the separation of natural product active ingredient.Double-aqueous phase system (ATPS) is by short chain alcohol/hydrophilic organic solvent
It is formed with inorganic matter.Patent CN107739359A has used the ethyl alcohol of 30-35wt%, the ammonium sulfate of 20-25wt%, 1.8-
The sodium chloride of 2.2wt% and the water of surplus form double-aqueous phase system, are centrifuged 10-15min under the revolving speed of 3000-6000r/min,
Extraction is stood, procyanidine recovery rate is up to 90% or more, and the distribution coefficient of phase reaches 5.2 up and down, illustrates that aqueous two-phase system can
To be able to achieve the extraction of mulberry pigment, colour component therein can be also separated to a certain extent.Therefore, aqueous two-phase system
It is considered as a kind of effective and general emerging isolation technics.But using in double-aqueous phase system separation mulberry red pigment
C3G, by itself and C3R is kept completely separate, still time-consuming, cumbersome, it is difficult to meet the needs in market.
Reaction-separation coupling technology is completed at the same time two processes of reaction and separation in a system, has good skill
Art economy and green friendly.Patent CN107141219A discloses a kind of UF membrane coupling esterification and prepares citric acid three
The method of ethyl ester, using Citric Acid Mono and ethyl alcohol as reaction raw materials, through esterification, activated carbon adsorption, vacuum distillation process system
Standby Triethyl Citrate with High Purity, purity are greater than 99.5%；Patent CN102094052A discloses a kind of glycosidase catalytic water
The method that solution prepares natural drug with salting-out extraction coupling converts dioscorea zingiberensis wright saponin(e and salting-out extraction using cellulase catalytic
Coupling, reaction efficiency improve 1 times than organic phase reaction, improve 27.6 times than aqueous phase reactions；Patent CN107955054A is disclosed
A kind of method that film simultaneous reaction and separation prepares phytosterin ester realizes the serialization of esterification and purifying, obtains purity
97% or more phytosterin ester, no poisonous and harmful waste material discharge.Therefore, reaction-separation coupling can efficiently obtain high-purity
Product has many advantages, such as that effectively energy-saving, reduction discharge and raw material utilize maximization.Therefore, by two aqueous phase extraction method with
Enzymic catalytic reaction-extraction and separation coupling combines, and is catalyzed while extracting mulberry red pigment using alpha-L-Rhamnosidase
C3R is converted to C3G improves C3G content is a novel bio-iabrication process.
However, the organic solvent contained can be right during double-aqueous phase system is for enzymatic conversion mulberry red pigment
The activity of resolvase or cell generates inhibiting effect.In view of immobilised enzymes has the stability for improving enzyme, good enzyme is obtained
Vigor and recycling degree, repeated multiple times can use, thus the advantages that reducing reaction cost, reduce environmental pollution
(CN101689638A), resolvase and cell therefore using immobilised enzymes are replaced.Enzyme immobilization technology passes through water-soluble enzyme
It is either physically or chemically fixed on immobilization material, makes enzyme not soluble in water.Patent CN106498000A is disclosed
A kind of method that the fixed trehalose synthase catalysis maltose of resin produces trehalose, prepares immobilised enzymes and is suitable for high concentration substrate,
Can be successive reaction 14-18 days at 50 DEG C, substantially increase the stability of enzyme.These advantages of immobilised enzymes can improve double water
The inhibiting effect that organic solvent may cause enzyme activity in phase system.Currently, there is no about ethyl alcohol-salt-immobilised enzymes liquid-
The report of liquid-solid system enzymatic hydrolysis-extraction and separation mulberry red pigment.Therefore, this research uses ethyl alcohol-salt aqueous two-phase body
System is added immobilization alpha-L-Rhamnosidase and forms ethyl alcohol-salt-immobilised enzymes liquid-liquid-solid three-phase system, extraction and separation mulberry fruit
Haematochrome, specific cleavage rhamnose glycosidic bond, by C3R orientation is converted into C3G is expected to improve C3G content develops novel high-quality
Mulberry red pigment.
Summary of the invention
The technical issues of solution: the present invention is in view of the above-mentioned problems, the present invention provides a kind of liquid-liquid-solid system enzymatic water
Solution-extraction and separation mulberry red pigment method.Using ethyl alcohol-salt-immobilised enzymes three-phase system, C is extracted3G and C3R, specificity are disconnected
Split C3The rhamnose glycosidic bond of R, directional catalyzing C3R is converted to C3G, to improve C3G content develops novel high-quality mulberry red pigment.
Technical solution: a kind of method of liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment, three-phase system
By gross mass by the ethyl alcohol of 15-35wt.%, the ammonium sulfate of 15-25wt.%, the mulberry juice of 5-20wt.%, 2-10wt.% fixed
Change the water composition of alpha-L-Rhamnosidase and surplus；In the item that pH is 3.5-5.5, temperature is 20-50 DEG C, the reaction time is 1-3h
Under part, extraction and separation mulberry red pigment utilizes the corn flower -3-O- in immobilization alpha-L-Rhamnosidase catalysis mulberry red pigment
Rutinoside (C3R), orientation is converted into C-3-G (C3G), the C of high concentration is made3G。
Preferably, the material that alpha-L-Rhamnosidase is fixed in above-mentioned three-phase system is multi-walled carbon nanotube.
Preferably, mass ratio shared by ethyl alcohol is 27.12wt.% in above-mentioned three-phase system.
Preferably, mass ratio shared by ammonium sulfate is 18.10wt.% in above-mentioned three-phase system.
Preferably, mass ratio shared by mulberry juice is 12.93wt.% in above-mentioned three-phase system.
Preferably, the mass ratio of immobilised enzymes is 4.24wt.% in above-mentioned three-phase system, and enzyme activity is 15.73 ± 0.03U/
mg。
Preferably, the pH reacted in above-mentioned three-phase system is 5.
Preferably, the reaction temperature in above-mentioned three-phase system is 45 DEG C.
The reaction principle of the synthesis of C-3-G are as follows:
The utility model has the advantages that being primary raw material present invention employs natural mulberry juice, the C of high concentration is prepared3G, exploitation
Novel high-quality mulberry red pigment.Gu using liquid-liquid-three-phase system, association reaction-separation coupling technology realizes single group
Divide C3The enrichment of G, extraction while again can separation product, substantially increase the rate of recovery；Immobilised enzymes is added, since it is three
It can effectively quickly be separated with product in phase system, realize being used repeatedly for immobilised enzymes, and just because of good point
The activity of enzyme is promoted again from effect, so that improving unit enzyme amount catalyzes and synthesizes C3The yield of G.Three complements each other, and generates
Journey is environmentally friendly, pollution-free, at low cost, and the rate of recovery is high, and the water solubility of product is good with tinctorial property, is easy to industrial applications,
With boundless market prospects.After liquid-liquid-solid system enzymatic hydrolysis-extraction and separation, C3The rate of recovery of G is expected to mention
Height is to 90% or more.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
The measuring method that detection mulberry pigment is used in the present embodiment is high performance liquid chromatography, chromatographic condition: Alltima
C18(250mm × 4.6mm, 5 μm), mobile phase: -1% phosphoric acid (55:25:5, V/V/V) of -5% acetic acid of 11% acetonitrile；Detection wavelength:
513nm；Flow velocity: 1.0mL/min；Column temperature: 35 DEG C；Sample volume: 20 μ L.
Wherein, high performance liquid chromatography detection is to two kinds of morins, including Cyanidin -3-O- glucoside (C3G it) and swears
Che Jusu -3-O- rutinoside (C3R)。
C3G、C3The calculation method of the R rate of recovery are as follows:
C3The calculation method of G yield are as follows:
Wherein: C, C0The concentration (mg/mL) of the forward and backward reactant of-reaction
V、V0The volume (mL) of the forward and backward reactant of-reaction
mC3G、mC3R—C3G、C3The quality (mg) of R
MC3G、MC3R—C3G、C3The molal weight of R
Embodiment 1
Take free alpha-L-Rhamnosidase and 9 kinds of immobilization materials: multi-walled carbon nanotube, carboxylated multi-wall carbon nano-tube
Pipe, hydroxyl multi-walled carbon nanotube, short functionalized multi-wall carbonnanotubes, short MWCNTs, carboxyl carbon nanotube, carbon nanotube
Nickel, short hydroxylated multi-walled carbon nanotubes, graphene, are added in double-aqueous phase system according to the ratio of 5wt.% respectively, form three
Phase system reacts 1h under the conditions of pH 4.5,35 DEG C of temperature.After reaction, it is centrifuged, stands, respectively from mutually sampling up and down, remember
The volume of phase up and down is recorded, and uses the C in HPLC detection up and down phase3G and C3R content, the results are shown in Table 1.The result shows that Suo Youtian
The C of the experimental group of immobilization alpha-L-Rhamnosidase is added3G overall recovery is above resolvase, and uses multi-wall carbon nano-tube
C of the pipe as immobilization material3G overall recovery highest, reaches 81.87 ± 0.75%.
The form of enzyme is to C in 1 system of table3The influence of G enzymatic conversion rate
Embodiment 2
Fresh mulberry fruit is taken, is squeezed the juice, is filtered, centrifugation obtains mulberry juice.Weigh the ethyl alcohol of 35wt.%, the sulfuric acid of 15wt.%
Ammonium, the mulberry juice of 5wt.% and the water of surplus are sufficiently mixed, and form double-aqueous phase system, anti-under the conditions of pH 3.5,20 DEG C of temperature
Answer 0.5h.After reaction, it is centrifuged, stands, respectively from mutually sampling up and down, record the volume of phase up and down, and detect using HPLC
C in phase up and down3G and C3R content.It is computed, C3The rate of recovery of G is 53.91 ± 0.74%, C3The rate of recovery of R be 52.74 ±
0.64%.
Take above-mentioned same system, after stablizing, add 2wt.% immobilization alpha-L-Rhamnosidase (enzyme activity 15.73 ±
0.03U/mg), liquid-liquid-solid three-phase system is formed, reacts 1h under the conditions of pH 3.5,30 DEG C of temperature.After reaction, it is centrifuged, it is quiet
It sets, respectively from mutually sampling up and down, records the volume of phase up and down, and use the C in HPLC detection up and down phase3G and C3R content.Through counting
It calculates, C3The enzymatic conversion yield of G is 8.47 ± 0.73%, C3The overall recovery of G is 62.38 ± 0.98%.
Embodiment 3
Fresh mulberry fruit is taken, is squeezed the juice, is filtered, centrifugation obtains mulberry juice.Weigh the ethyl alcohol of 27.12wt.%, 18.10wt.%
Ammonium sulfate, the mulberry juice of 12.93wt.% and the water of surplus is sufficiently mixed, and double-aqueous phase system is formed, in pH 4.5, temperature 35
0.5h is reacted under the conditions of DEG C.After reaction, it is centrifuged, stands, respectively from mutually sampling up and down, record the volume of phase up and down, and make
With the C in HPLC detection up and down phase3G and C3R content.It is computed, C3The rate of recovery of G is 73.71 ± 1.02%, C3The rate of recovery of R
It is 68.37 ± 1.13%.
Above-mentioned same system is taken, after stablizing, adds 4.24wt.% immobilization alpha-L-Rhamnosidase (enzyme activity 15.73
± 0.03U/mg), liquid-liquid-solid three-phase system is formed, reacts 1h under the conditions of pH 5, temperature 45 C.After reaction, it is centrifuged, it is quiet
It sets, respectively from mutually sampling up and down, records the volume of phase up and down, and use the C in HPLC detection up and down phase3G and C3R content.Through counting
It calculates, C3The enzymatic conversion yield of G is 19.71 ± 0.94%, C3The overall recovery of G is 93.42 ± 1.04%.
Embodiment 4
Fresh mulberry fruit is taken, is squeezed the juice, is filtered, centrifugation obtains mulberry juice.Weigh the ethyl alcohol of 15wt.%, the sulfuric acid of 25wt.%
Ammonium, the mulberry juice of 20wt.% and the water of surplus are sufficiently mixed, and form double-aqueous phase system.It is anti-under the conditions of pH 5.5, temperature 50 C
Answer 0.5h.It takes out, is centrifuged after reaction, stand, respectively from mutually sampling up and down, record the volume of phase up and down, and use HPLC
Detect the C in phase up and down3G and C3R content.It is computed, C3The rate of recovery of G is 65.86 ± 0.84%, C3The rate of recovery of R is
60.95 ± 0.84%.
Take above-mentioned same system, after stablizing, add 10wt.% immobilization alpha-L-Rhamnosidase (enzyme activity 15.73 ±
0.03U/mg), liquid-liquid-solid three-phase system is formed, reacts 1h under the conditions of pH 5.5, temperature 50 C.After reaction, it is centrifuged, it is quiet
It sets, respectively from mutually sampling up and down, records the volume of phase up and down, and use the C in HPLC detection up and down phase3G and C3R content.Through counting
It calculates, C3The enzymatic conversion yield of G is 14.76 ± 0.74%, C3The overall recovery of G is 80.62 ± 1.33%.
Claims (8)
1. a kind of liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment method, it is characterised in that three-phase system is pressed
Ethyl alcohol of the gross mass by 15-35wt.%, the ammonium sulfate of 15-25wt.%, the mulberry juice of 5-20wt.%, 2-10wt.% immobilization
Alpha-L-Rhamnosidase and the water of surplus composition；In the condition that pH is 3.5-5.5, temperature is 20-50 DEG C, the reaction time is 1-3h
Under, extraction and separation mulberry red pigment utilizes the corn flower -3-O- rue in immobilization alpha-L-Rhamnosidase catalysis mulberry red pigment
Fragrant glucosides (C3R), orientation is converted into C-3-G (C3G), the C of high concentration is made3G。
2. liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment method according to claim 1, feature
It is that the material that alpha-L-Rhamnosidase is fixed in the three-phase system is multi-walled carbon nanotube.
3. liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment method according to claim 1, feature
It is in the three-phase system that mass ratio shared by ethyl alcohol is 27.12wt.%.
4. liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment method according to claim 1, feature
It is in the three-phase system that mass ratio shared by ammonium sulfate is 18.10wt.%.
5. liquid-liquid-solid system enzymatic hydrolysis extraction and separation mulberry red pigment method according to claim 1, feature
It is in the three-phase system that mass ratio shared by mulberry juice is 12.93wt.%.
6. liquid-liquid-solid system enzymatic hydrolysis-extraction and separation mulberry red pigment method according to claim 1, special
Sign is that the mass ratio of immobilised enzymes in the three-phase system is 4.24wt.%, and enzyme activity is 15.73 ± 0.03U/mg.
7. liquid-liquid-solid system enzymatic hydrolysis-extraction and separation mulberry red pigment method according to claim 1, special
Sign is that the pH reacted in the three-phase system is 5.
8. liquid-liquid-solid system enzymatic hydrolysis-extraction and separation mulberry red pigment method according to claim 1, special
Levying the reaction temperature being in the three-phase system is 45 DEG C.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111254075A (en) * | 2020-03-14 | 2020-06-09 | 江苏科技大学 | Device and method for modifying mulberry red pigment through microfluidic two-aqueous-phase immobilized enzyme catalysis |
| CN112159382A (en) * | 2020-09-14 | 2021-01-01 | 华南农业大学 | Method for efficiently preparing active oligomeric proanthocyanidins from physiological fruit drop of litchi |
| CN113684235A (en) * | 2021-08-19 | 2021-11-23 | 江苏科技大学 | Method for converting mulberry red pigment component by double aqueous phase whole cell catalysis |
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| CN102875721A (en) * | 2012-10-18 | 2013-01-16 | 华东理工大学 | Two potential of hydrogen (pH) response regenerated polymers capable of forming acidic aqueous two-phase system and preparation methods and applications of two pH response regenerated polymers |
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| CN102094052A (en) * | 2010-12-12 | 2011-06-15 | 大连理工大学 | Method for preparing natural medicines by coupling glycosidase catalysis and salting-out extraction |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111254075A (en) * | 2020-03-14 | 2020-06-09 | 江苏科技大学 | Device and method for modifying mulberry red pigment through microfluidic two-aqueous-phase immobilized enzyme catalysis |
| CN112159382A (en) * | 2020-09-14 | 2021-01-01 | 华南农业大学 | Method for efficiently preparing active oligomeric proanthocyanidins from physiological fruit drop of litchi |
| CN112159382B (en) * | 2020-09-14 | 2023-02-28 | 华南农业大学 | Method for efficiently preparing active oligomeric proanthocyanidins from physiological fruit drop of litchi |
| CN113684235A (en) * | 2021-08-19 | 2021-11-23 | 江苏科技大学 | Method for converting mulberry red pigment component by double aqueous phase whole cell catalysis |
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Application publication date: 20181225 |