CN112858554A - Method for extracting anthocyanin substances from polluted membrane in membrane separation process - Google Patents
Method for extracting anthocyanin substances from polluted membrane in membrane separation process Download PDFInfo
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Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
Abstract
The invention relates to the technical field of extraction and identification of anthocyanin, and discloses a method for extracting anthocyanin substances from a polluted membrane in a membrane separation process, which comprises the following steps: (1) pretreatment of a polluted film: drying the polluted membrane at 25 +/-2 ℃ in a dark place, and cutting the polluted membrane into membrane fragments; (2) preparing an extraction solvent: fully mixing acetonitrile, methanol, isopropanol, water and acetic acid to prepare an extraction solvent; (3) extracting anthocyanin: mixing the membrane fragments and the extraction solvent in a light-proof container, stirring for 1-2h at 25 + -2 deg.C in the dark, centrifuging, and collecting supernatant to obtain anthocyanin extract; (4) and (3) anthocyanin identification: and identifying the anthocyanin in the anthocyanin extracting solution. The invention creatively compounds acetonitrile, methanol, isopropanol, water and acetic acid as an extraction solvent, can extract anthocyanin substances from a polluted membrane, and has better extraction effect.
Description
Technical Field
The invention relates to the technical field of extraction and identification of anthocyanin, in particular to a method for extracting anthocyanin substances from a polluted membrane in a membrane separation process.
Background
Blueberry and blueberry extracts are known for their high content of anthocyanins, which have high antioxidant capacity and can play an important role in preventing many degenerative diseases such as cancer, cardiovascular disease and alzheimer disease by neutralizing unstable free radicals. Blueberries are seasonal fruits, are not easy to store, and are often processed into jams, juices, or high anthocyanin content blueberry extracts. Concentrated blueberry juice or extract thereof is the most common preservation method to reduce volume or weight, reduce packaging, facilitate handling and transportation, and provide a longer shelf life for the concentrate.
Membrane separation technology is a useful technology for recovering, fractionating, and concentrating phenolic compounds from the products, by-products, and aqueous or alcoholic waste processing of biomass processing, and has been successfully used in food and beverage industries such as dairy products, fruit juices, wine, vegetable oils, drinking water, and agricultural wastewater. The membrane separation technology utilizes the selectivity of a membrane, generally takes the concentration gradient or the operating pressure of feed liquid and filtrate as a driving force, and intercepts macromolecular substances larger than the pore diameter when a mixture of molecules with different particle diameters passes through a semi-permeable membrane with certain molecular weight cutoff on the molecular level, so that the micromolecular substances pass through the membrane pores and enter the filtrate along with a solvent, thereby realizing the selective separation. As a non-thermal separation technology, the membrane separation technology replaces the traditional concentration method by the advantages of low energy consumption, few process steps, high separation efficiency, good product quality, capability of meeting different separation requirements of clarification, concentration and the like in the fruit juice processing process by membranes with different molecular weight cut-off values and the like.
Membrane fouling is a major problem that restricts membrane separation technology. For example, blueberry contains a large amount of phenolic substances, particularly anthocyanin substances, and is easy to interact with other components in juice or extract, such as secondary metabolites of protein, carbohydrate, lipid and the like, and the secondary metabolites are easy to cause irreversible changes in membrane flux, separation characteristics and the like after being adsorbed on a membrane. To characterize and identify fouling, compounds on/in the membrane must first be extracted. However, there is no report on the extraction of anthocyanins from membrane materials, and the method for extracting anthocyanins from plants is not suitable for membrane materials because: anthocyanins bind tightly to membranes and organic fouling tends to form complexes on membranes, which can increase the difficulty of extracting and identifying anthocyanins from the fouled membranes. For example, chinese patent application No. CN200610013546.6 discloses a method for extracting anthocyanin from black bean skin, comprising the following steps: (1) extracting the black bean skin raw material: adding ethanol water solution or methanol water solution into the black bean hull raw material, soaking, extracting, filtering, wherein the pH of the ethanol water solution or methanol water solution is 1-4, concentrating the leaching solution until no alcohol exists, standing, and removing the precipitate to obtain supernatant; (2) and (3) adsorbing and separating the styrene resin. The acidic ethanol aqueous solution or methanol aqueous solution has a good effect of extracting anthocyanin in plants, but the effect is not ideal when used for extracting anthocyanin from a membrane.
Disclosure of Invention
In order to solve the technical problem, the invention provides a method for extracting anthocyanin substances from a polluted membrane in a membrane separation process. The method can extract anthocyanin substances from the polluted membrane, and has good extraction effect.
The specific technical scheme of the invention is as follows:
a method for extracting anthocyanin substances from a polluted membrane in a membrane separation process comprises the following steps:
(1) pretreatment of a polluted film: drying the polluted membrane at 25 +/-2 ℃ in a dark place, and cutting the polluted membrane into membrane fragments;
(2) preparing an extraction solvent: fully mixing acetonitrile, methanol, isopropanol, water and acetic acid to prepare an extraction solvent;
(3) extracting anthocyanin: mixing the membrane fragments and the extraction solvent in a dark container, stirring for 1-2h at 25 + -2 deg.C in the dark, centrifuging, and collecting supernatant to obtain anthocyanin extract.
In the contaminated membrane, anthocyanin is tightly combined with the membrane, and is easy to form a compound with monosaccharide, polysaccharide, phenolic acid and the like, so compared with the extraction of anthocyanin substances from plants, the extraction conditions from the membrane are more severe. After a large number of experiments, the inventor creatively compounds acetonitrile, methanol, isopropanol, water and acetic acid as an extraction solvent, can successfully extract anthocyanin substances from a polluted membrane, and has a good extraction effect; moreover, each component in the extraction solvent is crucial to the extraction of anthocyanin in the film, and the lack of any component causes unsatisfactory extraction effect.
In addition, anthocyanin substances are poor in stability and are easily degraded into phenolic acid and aldehydes under the action of light and heat, so that the pretreatment of the polluted membrane and the extraction process of anthocyanin are carried out under the conditions of being away from light and being close to room temperature, and the inaccurate identification result caused by degradation of anthocyanin is prevented.
In the step (1), the polluted membrane can be an ultrafiltration membrane, a nanofiltration membrane, a reverse osmosis membrane or a microfiltration membrane, and the material of the polluted membrane can be polyether sulfone (PES), Polyacrylonitrile (PAN), polyvinylidene fluoride (PVDF), Polystyrene (PS) or Polyamide (PA).
Preferably, in the step (2), the volume ratio of the acetonitrile to the methanol to the isopropanol to the water to the acetic acid is 25:25:25: 0.1-0.5.
Further, in the step (2), the volume ratio of the acetonitrile to the methanol to the isopropanol to the water to the acetic acid is 25:25:25:25: 0.1.
Besides the components of the extraction solvent, the ratio of the components also affects the extraction effect of anthocyanin in the polluted membrane. The inventor finds through experiments that when the volume ratio of acetonitrile, methanol, isopropanol, water and acetic acid is controlled to be 25:25:25:25:0.1-0.5, the amount of monomeric anthocyanin and polymeric anthocyanin extracted from the membrane is large, and when the volume ratio is controlled to be 25:25:25:25:0.1, the extraction effect is best.
Preferably, in the step (3), the mass-to-volume ratio of the membrane fragments to the extraction solvent is 4-10g:100 mL.
Preferably, in the step (4), after the anthocyanin extract is obtained, the anthocyanin in the anthocyanin extract is identified by HPLC-MS (high performance liquid chromatography-mass spectrometry combined technology).
Preferably, in the step (1), the drying method is natural drying, and the drying time is 18-24 h.
Preferably, in the step (3), a magnetic stirrer is adopted for stirring, and the rotation speed is 750-1000 rpm.
Preferably, in step (3), the light-shielding container is a brown bottle.
Preferably, in the step (3), the rotation speed of the centrifugation is 5000-.
Preferably, the operating conditions of HPLC (high performance liquid chromatography) are as follows: a reversed phase C-18 column was used, mobile phase A was 1-5wt% aqueous formic acid, mobile phase B was acetonitrile, the flow rate was 1-1.5mL/min, and the detection wavelength was 520 nm.
Preferably, the operating conditions of the MS (Mass Spectrometry) are as follows: detecting by adopting an ESI ion source and a positive ion sensitivity mode; the capillary voltage is 2.8-3.2kV, the sample taper hole voltage is 25-35V, the sample extraction voltage is 4.8-5.3V, the ion source temperature is 115-125 ℃, and the desolventizing gas temperature is 345-355 ℃; the spray gas is high-purity nitrogen, the collision gas is high-purity argon, the flow rate of the back-blowing gas is 75-85L/h, and the flow rate of the desolventizing gas is 750-; the scanning range of the mass spectrum is 100-1200Da, and the scanning times are 0.2-0.4 s.
Compared with the prior art, the invention has the following advantages:
(1) the pretreatment of the polluted membrane and the extraction process of the anthocyanin are carried out under the conditions of light resistance and near room temperature, so that the inaccurate identification result caused by degradation of the anthocyanin can be prevented;
(2) the extraction solvent is a mixed solution of acetonitrile, methanol, isopropanol, water and acetic acid, and the proportion of the components is controlled within a certain range, so that the extraction effect on anthocyanin substances in the polluted membrane is good.
Drawings
FIG. 1 is a mass spectrum of the anthocyanin identification in example 1; wherein, the figure (a) is a mass spectrogram of the feeding liquid, and the figure (b) is a mass spectrogram of the anthocyanin extracting solution;
FIG. 2 is the mass spectrum of 14 anthocyanin monomers, chalcone and myricetin in the feed liquid.
Detailed Description
The present invention will be further described with reference to the following examples.
General examples
A method for extracting anthocyanin substances from a polluted membrane in a membrane separation process comprises the following steps:
(1) pretreatment of a polluted film: drying the polluted membrane at 25 +/-2 ℃ in a dark place for 18-24h, and cutting into membrane fragments;
(2) preparing an extraction solvent: fully mixing acetonitrile, methanol, isopropanol, water and acetic acid according to a volume ratio of 25:25:25:25:0.1-0.5 to prepare an extraction solvent;
(3) extracting anthocyanin: mixing the membrane fragments and the extraction solvent in a light-proof container according to the mass-volume ratio of 4-10g:100mL, placing the mixture on a magnetic stirring instrument, stirring the mixture for 1-2h at the rotating speed of 750 plus-1000 rpm in the dark at the temperature of 25 plus-minus 2 ℃, then centrifuging the mixture for 10-20min at the rotating speed of 5000 plus-6500 rpm at the temperature of 2-6 ℃, and collecting the supernatant to obtain the anthocyanin extracting solution;
(4) and (3) anthocyanin identification: identifying anthocyanin in the anthocyanin extracting solution by HPLC-MS;
the operating conditions for HPLC were as follows: using a reversed phase C-18 column, wherein the mobile phase A is 1-5wt% formic acid aqueous solution, the mobile phase B is acetonitrile, the flow rate is 1-1.5mL/min, and the detection wavelength is 520 nm;
the operating conditions for MS were as follows: detecting by adopting an ESI ion source and a positive ion sensitivity mode; the capillary voltage is 2.8-3.2kV, the sample taper hole voltage is 25-35V, the sample extraction voltage is 4.8-5.3V, the ion source temperature is 115-125 ℃, and the desolventizing gas temperature is 345-355 ℃; the spray gas is high-purity nitrogen, the collision gas is high-purity argon, the flow rate of the back-blowing gas is 75-85L/h, and the flow rate of the desolventizing gas is 750-; the scanning range of the mass spectrum is 100-1200Da, and the scanning times are 0.2-0.4 s.
Example 1
The pollution membrane is derived from a membrane concentration process of blueberry extract, and the membrane concentration process comprises the following steps:
(I) crushing 25g of dried blueberries by a food processor, dispersing in a brown glass bottle containing 2L of pure water, stirring and extracting for 1.5h on a magnetic stirrer at the speed of 750rpm in the dark at the temperature of 25 ℃, carrying out suction filtration (by using filter paper with the diameter of GB-191490 mm) to obtain a crude blueberry aqueous extract, placing the crude blueberry aqueous extract in a refrigerated centrifuge at the speed of 5000rpm, centrifuging for 10min, and centrifuging at the temperature of 4 ℃ to obtain a supernatant;
and (II) concentrating the supernatant obtained in the step (I) by using a nanofiltration membrane (400Da) made of PA material under the conditions of transmembrane pressure of 1.0MPa, flow rate of 1.0L/min and temperature of 25 +/-2 ℃ in a dark place to obtain a blueberry extract concentrated solution with a volume concentration coefficient of 2.0.
Taking out the polluted membrane subjected to nanofiltration in the step (II), and extracting anthocyanin substances from the polluted membrane, wherein the method comprises the following steps:
(1) pretreatment of a polluted film: naturally drying the polluted membrane in dark (the temperature is 25 +/-2 ℃) for 24 hours, and then shearing the polluted membrane into membrane fragments with the size of about 3mm multiplied by 3 mm;
(2) preparing an extraction solvent: fully mixing acetonitrile, methanol, isopropanol, water and acetic acid according to a volume ratio of 25:25:25:25:0.1 to prepare an extraction solvent;
(3) extracting anthocyanin: mixing the membrane fragments and the extraction solvent in a brown bottle according to the mass volume ratio of 8g to 100mL, placing the mixture on a magnetic stirring instrument, stirring the mixture for 1.5h at the rotating speed of 750rpm in the dark at the temperature of 25 ℃, then centrifuging the mixture for 10min at the rotating speed of 5000rpm at the temperature of 4 ℃, and collecting the supernatant to obtain the anthocyanin extracting solution.
And (3) identifying anthocyanin in the feed liquid (namely the blueberry extract concentrated solution obtained in the step (II)) and the anthocyanin extracting solution obtained in the step (3) by HPLC-MS, wherein the operating conditions of the HPLC-MS are as follows:
operating conditions of HPLC: using a Waters 2695 high performance liquid chromatograph and a Waters 2489 ultraviolet detector; a ZORBAX C18 column (250 mm. times.4.6 mm. times.5 μm, Agilent, USA) was used, mobile phase A was 5wt% aqueous formic acid, mobile phase B was acetonitrile, the flow rate was 1mL/min, and the gradient protocol was as follows: 5% B (0-5 min), 5% B (5-15 min), 10% B (15-28 min), 10% B (28-35 min), 13% B (35-50 min), 5% B (50-55 min); keeping the temperature of the column at 25 ℃, wherein the detection wavelength is 520nm, and the sample injection amount is 10 mol/L;
operating conditions of the MS: detecting by using a Waters UPLC-Synapt G2 combined instrument and an ESI ion source in a positive ion sensitivity mode; the capillary voltage is 3.0kV, the sample taper hole voltage is 30V, the sample extraction voltage is 5.0V, the ion source temperature is 120 ℃, and the desolventizing gas temperature is 350 ℃; the spray gas is high-purity nitrogen, the collision gas is high-purity argon, the flow rate of the back blowing gas is 80L/h, and the flow rate of the desolventizing gas is 800L/h; the mass spectrum scanning range is 100-1200Da, and the scanning times are 0.3 s; the standard substance of the calibration curve is sodium formate; real-time calibration standard m/z 556.2771+ (leucine enkephalin);
HPLC charts of the obtained feed solution and anthocyanin extract are shown in FIG. 1(a) and FIG. 1(b), respectively, and mass spectra of each peak in FIG. 1(a) are shown in FIG. 2. The retention time and mass-to-charge ratio of each peak were obtained from fig. 2, and the kind of monomeric anthocyanin represented by each peak was determined based on the retention time and mass-to-charge ratio, and the results are shown in table 1.
TABLE 1 identification of anthocyanin monomers
Comparing table 1 and fig. 1(b), it was confirmed that 7 kinds of anthocyanins similar to those in the blueberry extract concentrate were extracted from the contaminated membrane, which were delphinidin-3-O-galactoside, delphinidin-3-O-glucoside, delphinidin-3-O-arabinoside, cyanidin-3-O-galactoside, morning glory-3-O-galactoside, peoniflorin-3-O-glucoside, and malvidin-3-O-arabinoside, respectively, and chalcone and myricetin were detected.
Example 2
Anthocyanin-type substances were extracted from the same contaminated membrane as in example 1, comprising the steps of:
(1) pretreatment of a polluted film: naturally drying the polluted membrane in dark (the temperature is 25 +/-2 ℃) for 24 hours, and then shearing the polluted membrane into membrane fragments with the size of about 3mm multiplied by 3 mm;
(2) preparing an extraction solvent: fully mixing acetonitrile, methanol, isopropanol, water and acetic acid according to a volume ratio of 25:25:25:25:0.1 to prepare an extraction solvent;
(3) extracting anthocyanin: mixing the membrane fragments and the extraction solvent in a brown bottle according to the mass volume ratio of 4g to 100mL, placing the mixture on a magnetic stirring instrument, stirring the mixture for 1.5h at the rotating speed of 750rpm in the dark at the temperature of 25 ℃, then centrifuging the mixture for 10min at the rotating speed of 5000rpm at the temperature of 4 ℃, and collecting the supernatant to obtain the anthocyanin extracting solution.
Example 3
This example is different from example 2 in that acetonitrile, methanol, isopropanol, water, and acetic acid were sufficiently mixed at a volume ratio of 25:25:25:25:0.3 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Example 4
This example is different from example 2 in that acetonitrile, methanol, isopropanol, water, and acetic acid were sufficiently mixed at a volume ratio of 25:25:25:25:0.5 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Example 5
This example is different from example 2 in that acetonitrile, methanol, isopropanol, water, and acetic acid were sufficiently mixed at a volume ratio of 25:25:25:25:1 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Example 6
This example is different from example 2 in that acetonitrile, methanol, isopropanol, water, and acetic acid were sufficiently mixed at a volume ratio of 30:30:30:10:0.1 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Example 7
This example is different from example 2 in that acetonitrile, methanol, isopropanol, water, and acetic acid were sufficiently mixed at a volume ratio of 20:40:20:20:0.1 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Comparative example 1
This comparative example is different from example 2 in that in step (2), ethanol, water, and hydrochloric acid were mixed to prepare an extraction solvent, wherein the volume ratio of ethanol to water was 20:80, the mass fraction of HCl was 0.1 wt%, and the other steps were the same as example 2.
Comparative example 2
This comparative example is different from example 2 in that in step (2), methanol, water, and hydrochloric acid were mixed to prepare an extraction solvent, wherein the volume ratio of methanol to water was 80:20, the mass fraction of HCl was 0.1 wt%, and the other steps were the same as example 2.
Comparative example 3
This comparative example is different from example 2 in that acetonitrile, methanol, isopropanol, and water were sufficiently mixed at a volume ratio of 25:25:25:25 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Comparative example 4
This comparative example is different from example 2 in that, in step (2), methanol, isopropanol, water and acetic acid were sufficiently mixed at a volume ratio of 25:25:25:0.1 to prepare an extraction solvent, and the other steps were the same as example 2.
Comparative example 5
This comparative example is different from example 2 in that acetonitrile, isopropanol, water, and acetic acid were sufficiently mixed at a volume ratio of 25:25:25:0.1 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Comparative example 6
This comparative example is different from example 2 in that acetonitrile, methanol, water, and acetic acid were sufficiently mixed at a volume ratio of 25:25:25:0.1 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Comparative example 7
This comparative example is different from example 2 in that acetonitrile, methanol, isopropanol, and acetic acid were sufficiently mixed at a volume ratio of 25:25:25:0.1 in step (2) to prepare an extraction solvent, and the other steps were the same as example 2.
Test example
The contents of total monomeric anthocyanin and polymeric anthocyanin in the polluted membranes were obtained by measuring the monomeric anthocyanin and the polymeric anthocyanin in the anthocyanin extract solutions obtained in examples 2 to 7 and comparative examples 1 to 7, and the specific method was as follows:
(1) determination of monomeric anthocyanin:
the anthocyanin extract was diluted with potassium chloride buffer (pH 1.0) and sodium acetate buffer (pH 4.5). The mixture was left in the dark for 30min, and the absorbance was measured at 520nm and 700nm, respectively, using a spectrophotometer. TAC (tetra acetic acid)1The calculation formula of (a) is as follows:
MW, molecular weight of anthocyanin (cyanidin-3-glucoside, 449.2 g/mol); DF, dilution factor; ε, extinction coefficient (26900L/mol cm); l, 1 cm.
Total monomer anthocyanin content TAC in contaminated film2The calculation formula of (a) is as follows:
in the formula, 10, the volume of the solvent for extracting the membrane fouling, mL; 0.4, contaminated membrane mass, g; DF, determination of TAC1Dilution factor of supernatant.
(2) Determination of polymerized anthocyanin:
diluting the anthocyanin extract with pure water to make its absorbance at 520nm between 0.5-1.0. To 2.8mL of the diluted sample was added 0.2mL of 0.9M potassium metabisulfite, and to 2.8mL of the diluted sample (unbleached control sample) was added 0.2mL of distilled water. After standing for 15min, the samples were measured at 700nm, 520nm and 420nm, respectively. The color density of the control sample was calculated as follows:
color density=[(A420nm-A700nm)+(A520nm-A700nm)]×dilution factor
bleaching the sample with bisulfite to determine the polymerized anthocyanin content, the formula is as follows:
polymeric color=[(A420nm-A700nm)+(A520nm-A700nm)]×dilution factor
the percent polymerized color was calculated as follows:
%polymeric color=(polymeirc color/color density)×100
the calculation formula of the total polymerized anthocyanin content in the polluted membrane is as follows:
the results of measuring the contents of total monomeric anthocyanins and polymeric anthocyanins in the contaminated membrane are shown in table 2.
TABLE 2 Mixed solvent extraction of anthocyanin from Membrane fouling
Comparing the data in table 2 for each example and comparative example, the following conclusions can be drawn:
(1) in the prior art for extracting anthocyanin from plants, acidic aqueous methanol solution or aqueous ethanol solution is generally used as an extraction solvent, and the two extraction solvents are used for extracting anthocyanin in a polluted membrane in comparative example 1 and comparative example 2, and the obtained monomeric anthocyanin and polymeric anthocyanin are obviously lower in amount than in example 2, which indicates that the extraction solvents in the prior art are not suitable for extracting anthocyanin substances from the polluted membrane.
(2) The extraction solvents adopted in comparative examples 3-7 respectively contain one less component, the amounts of the extracted monomeric anthocyanin and polymeric anthocyanin are obviously lower than those of example 2, which shows that the components in the extraction solvents are all important for extracting anthocyanin in the membrane, and the lack of any one component can cause unsatisfactory extraction effect.
(3) In examples 2 to 7, a mixed solution of acetonitrile, methanol, isopropanol, water, and acetic acid was used as an extraction solvent, and the ratio of each component was different. The amounts of monomeric anthocyanin and polymeric anthocyanin extracted in examples 2-4 were higher than those in examples 5-7, wherein example 2 is the highest, and shows that when the volume ratio of acetonitrile, methanol, isopropanol, water and acetic acid is controlled to be 25:25:25:0.1-0.5, the extraction effect on anthocyanin in the contaminated membrane is better, and the extraction effect is the best when the volume ratio is 25:25:25: 0.1.
The raw materials and equipment used in the invention are common raw materials and equipment in the field if not specified; the methods used in the present invention are conventional in the art unless otherwise specified.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and all simple modifications, alterations and equivalents of the above embodiments according to the technical spirit of the present invention are still within the protection scope of the technical solution of the present invention.
Claims (10)
1. A method for extracting anthocyanin substances from a polluted membrane in a membrane separation process is characterized by comprising the following steps:
(1) pretreatment of a polluted film: drying the polluted membrane at 25 +/-2 ℃ in a dark place, and cutting the polluted membrane into membrane fragments;
(2) preparing an extraction solvent: fully mixing acetonitrile, methanol, isopropanol, water and acetic acid to prepare an extraction solvent;
(3) extracting anthocyanin: mixing the membrane fragments and the extraction solvent in a dark container, stirring for 1-2h at 25 + -2 deg.C in the dark, centrifuging, and collecting supernatant to obtain anthocyanin extract.
2. The method according to claim 1, wherein in the step (2), the volume ratio of the acetonitrile, the methanol, the isopropanol, the water and the acetic acid is 25:25:25:25: 0.1-0.5.
3. The method of claim 1, wherein in step (3), the mass to volume ratio of membrane fragments to extraction solvent is 4-10g:100 mL.
4. The method according to claim 1, wherein in step (3), after the anthocyanin extract is obtained, anthocyanins in the anthocyanin extract are identified by HPLC-MS.
5. The method according to claim 1, wherein in the step (1), the drying method is natural drying, and the drying time is 18-24 h.
6. The method as claimed in claim 1, wherein in step (3), the stirring is performed by using a magnetic stirrer at a rotation speed of 750-.
7. The method of claim 1, wherein in step (3), the light-resistant container is a brown bottle.
8. The method as claimed in claim 1, wherein in the step (3), the rotation speed of the centrifugation is 5000-.
9. The method of claim 4, wherein the HPLC conditions are as follows: a reversed phase C-18 column was used, mobile phase A was 1-5wt% aqueous formic acid, mobile phase B was acetonitrile, the flow rate was 1-1.5mL/min, and the detection wavelength was 520 nm.
10. The method of claim 4, wherein the operating conditions of the MS are as follows: detecting by adopting an ESI ion source and a positive ion sensitivity mode; the capillary voltage is 2.8-3.2kV, the sample taper hole voltage is 25-35V, the sample extraction voltage is 4.8-5.3V, the ion source temperature is 115-125 ℃, and the desolventizing gas temperature is 345-355 ℃; the spray gas is high-purity nitrogen, the collision gas is high-purity argon, the flow rate of the back-blowing gas is 75-85L/h, and the flow rate of the desolventizing gas is 750-; the scanning range of the mass spectrum is 100-1200Da, and the scanning times are 0.2-0.4 s.
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CN115057899A (en) * | 2022-07-26 | 2022-09-16 | 山东省农业科学院 | Method for extracting anthocyanin from mulberry wine residues |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007125562A2 (en) * | 2006-04-28 | 2007-11-08 | Giuseppe Lazzarino | Method for the preparation and use of an enriched cyanidine-s-o-beta-glucopyranoside extract and derivatives thereof from fruits and vegetables containing said anthocyanin and method for the purification and use of cyanidine-3-o-beta- glucopyranoside and derivatives thereof obtained |
CN101701945A (en) * | 2009-11-20 | 2010-05-05 | 广东省农业科学院蚕业与农产品加工研究所 | Method for determining anthocyanin composition spectrum and content in germplasm and seed coat of black soyabean by utilizing HPLC |
EP2204229A1 (en) * | 2007-10-03 | 2010-07-07 | Fujifilm Corporation | Method of producing emulsion or dispersion and food, skin external preparation and drug containing emulsion or dispersion obtained by the production method |
JP2010236905A (en) * | 2009-03-30 | 2010-10-21 | Meiji Seika Kaisha Ltd | Method for analysis of anthocyanin |
CN103235080A (en) * | 2013-05-13 | 2013-08-07 | 山东省农业科学院中心实验室 | Method for quickly determining anthocyanin in seed coat of black peanut by using UPLC/MS/MS (Ultra Performance Liquid Chromatography/tandem Mass Spectrometry) |
CN103760289A (en) * | 2014-02-17 | 2014-04-30 | 江苏省农业科学院 | Extraction and high efficiency liquid-phase measurement method for anthocyanin in blood-flesh peach fruits |
CN106046074A (en) * | 2016-04-06 | 2016-10-26 | 李鹏民 | Glycosylation derivatives of 3-hydroxyphloretin and extraction method thereof |
CN106188180A (en) * | 2015-04-30 | 2016-12-07 | 中国科学院大连化学物理研究所 | The isolation and purification method of tree peony anthocyanins isomer in a kind of black Fructus Lycii |
CN107966517A (en) * | 2017-08-11 | 2018-04-27 | 江苏省农业科学院 | It is a kind of to measure the method for anthocyanin component and content in strawberry fruit using HPLC-MS/MS |
CN108165589A (en) * | 2017-12-23 | 2018-06-15 | 安徽工程大学 | A kind of fungi anthocyanin class red pigment and its fermentation preparation |
CN108409809A (en) * | 2018-06-13 | 2018-08-17 | 西北农林科技大学 | A kind of dihydro looks into youngster's ketose glycoside derivates and its extracting method |
-
2020
- 2020-12-31 CN CN202011627299.5A patent/CN112858554A/en active Pending
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007125562A2 (en) * | 2006-04-28 | 2007-11-08 | Giuseppe Lazzarino | Method for the preparation and use of an enriched cyanidine-s-o-beta-glucopyranoside extract and derivatives thereof from fruits and vegetables containing said anthocyanin and method for the purification and use of cyanidine-3-o-beta- glucopyranoside and derivatives thereof obtained |
EP2204229A1 (en) * | 2007-10-03 | 2010-07-07 | Fujifilm Corporation | Method of producing emulsion or dispersion and food, skin external preparation and drug containing emulsion or dispersion obtained by the production method |
JP2010236905A (en) * | 2009-03-30 | 2010-10-21 | Meiji Seika Kaisha Ltd | Method for analysis of anthocyanin |
CN101701945A (en) * | 2009-11-20 | 2010-05-05 | 广东省农业科学院蚕业与农产品加工研究所 | Method for determining anthocyanin composition spectrum and content in germplasm and seed coat of black soyabean by utilizing HPLC |
CN103235080A (en) * | 2013-05-13 | 2013-08-07 | 山东省农业科学院中心实验室 | Method for quickly determining anthocyanin in seed coat of black peanut by using UPLC/MS/MS (Ultra Performance Liquid Chromatography/tandem Mass Spectrometry) |
CN103760289A (en) * | 2014-02-17 | 2014-04-30 | 江苏省农业科学院 | Extraction and high efficiency liquid-phase measurement method for anthocyanin in blood-flesh peach fruits |
CN106188180A (en) * | 2015-04-30 | 2016-12-07 | 中国科学院大连化学物理研究所 | The isolation and purification method of tree peony anthocyanins isomer in a kind of black Fructus Lycii |
CN106046074A (en) * | 2016-04-06 | 2016-10-26 | 李鹏民 | Glycosylation derivatives of 3-hydroxyphloretin and extraction method thereof |
CN107966517A (en) * | 2017-08-11 | 2018-04-27 | 江苏省农业科学院 | It is a kind of to measure the method for anthocyanin component and content in strawberry fruit using HPLC-MS/MS |
CN108165589A (en) * | 2017-12-23 | 2018-06-15 | 安徽工程大学 | A kind of fungi anthocyanin class red pigment and its fermentation preparation |
CN108409809A (en) * | 2018-06-13 | 2018-08-17 | 西北农林科技大学 | A kind of dihydro looks into youngster's ketose glycoside derivates and its extracting method |
Non-Patent Citations (2)
Title |
---|
M. BDIRI ET AL.: "Identification of phenolic compounds and their fouling mechanisms in ionexchange membranes used at an industrial scale for wine tartaric stabilization by electrodialysis", 《SEPARATION AND PURIFICATION TECHNOLOGY》 * |
宋小蒙 等: "HPLC-ESI-MS/MS 分析金钗石斛花花色苷组成及其抗氧化活性测定", 《江苏农业科学》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115057899A (en) * | 2022-07-26 | 2022-09-16 | 山东省农业科学院 | Method for extracting anthocyanin from mulberry wine residues |
CN115057899B (en) * | 2022-07-26 | 2023-09-22 | 山东省农业科学院 | Method for extracting anthocyanin from mulberry wine residues |
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