CN106518590A - Method for extracting polyphenol substances from pomegranate peel by using low eutectic solvent - Google Patents
Method for extracting polyphenol substances from pomegranate peel by using low eutectic solvent Download PDFInfo
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- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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Abstract
The present invention relates to the technical field of ionic liquid applications, more particularly to a method for extracting polyphenol substances from pomegranate peel by using a low eutectic solvent. The method comprises: drying, crushing and screening pomegranate peel; mixing the screened pomegranate peel and a low eutectic solvent, and carrying out ultrasonic heating extraction, such that the polyphenol substances in the pomegranate peel is extracted into the low eutectic solvent to obtain a polyphenol substance-containing eutectic solvent; and centrifugating, taking the centrifugating liquid, adding ethanol to the centrifugating liquid, diluting, and filtering with an organic filtration membrane. According to the present invention, the method has advantages of mild condition, convenient operation, complete polyphenol substance extraction, and high extraction efficiency.
Description
Technical field
The present invention relates to ionic liquid applied technical field, and in particular to a kind of to be extracted in Pericarpium Granati using eutectic solvent
The method of polyphenols.
Background technology
The uniquenesses such as there is ionic liquid steam to force down, non-combustible, dissolubility and excellent conductivity, electrochemical stability window width
Physicochemical properties, receive much attention in fields such as isolation technics, living things catalysis, organic synthesiss and electrochemistry.However, ionic liquid
Body exist building-up process complexity, purification difficult, it is relatively costly the shortcomings of, so as to limit its heavy industrialization application and send out
Exhibition.Additionally, relevant toxicological study shows, pyridine and glyoxaline ion liquid non-fully " green ", its toxicity is organic with tradition
Solvent is suitable, even greater than conventional organic solvents.Therefore, find simple, the economic and more green replacement solvent of synthesis to have
Highly important meaning.
2003, Abbott etc. was found that a kind of physicochemical properties formed by quaternary ammonium salt and amide compound are excellent first
Good solvent eutectic solvent (Deep Eutectic Solvents).This nontoxic solvent, it is biodegradable, and synthesize
Process atom utilization, up to 100%, is a kind of new green solvent.The physicochemical properties of eutectic solvent and ionic liquid
It is extremely similar, therefore also someone is classified as a class novel ion liquid or ionic liquid analog it.At present, eutectic solvent has been
The extensive attention of countries in the world researcher is caused, and it is aobvious in fields such as separation process, chemical reaction, functional material and electrochemistry
Good application prospect is shown.
In addition, containing polyphenols, mainly chlorogenic acid, tan in prior art in Punica granatum L. processed side product Pericarpium Granati
Flower acid etc..Chlorogenic acid has antioxidation, antibacterial, antitoxin, eliminates many use such as free radical, defying age, anti-skeletal muscle be aging
Place；Ellagic acid then shows to induce canceration and other various cancerations to have obvious inhibitory action chemical substance, particularly to knot
Intestinal cancer, the esophageal carcinoma, hepatocarcinoma, pulmonary carcinoma, tongue and skin carcinoma etc. have good inhibiting effect.The extraction process of Pericarpium Granati in prior art
Exist and extract not thoroughly, the defect of complex process etc..
Therefore, need a kind of method for providing that polyphenols in Pericarpium Granati are thoroughly extracted in simple to operate, extraction badly.Mesh
Before, also do not find both at home and abroad to extract the relevant report of polyphenols in Pericarpium Granati using eutectic solvent.
The content of the invention
It is an object of the invention to provide a kind of using the eutectic solvent extraction for synthesizing simple, dissolubility height, safe green
The method of polyphenols in Pericarpium Granati, with it is simple to operate, extract thoroughly advantage.
The method that employing eutectic solvent of the present invention extracts polyphenols in Pericarpium Granati, comprises the following steps：
(1) material prepares：Pericarpium Granati is dried, crushes, is sieved；
(2) Ultrasonic Heating is extracted：Pericarpium Granati after step (1) is sieved is mixed with eutectic solvent, and Jing Ultrasonic Heatings are carried
Take, the polyphenols in Pericarpium Granati are extracted in eutectic solvent, obtain the eutectic solvent containing polyphenols；
(3) centrifugation, dilution, filtration：After the centrifugation of the eutectic solvent containing polyphenols that first step (2) is obtained,
Extracting centrifugal liquid, then add ethanol dilution in centrifugal liquid, most after the organic membrane filtrations of Jing.
Wherein：
In step (1), Pericarpium Granati is crushed to 60～120 mesh.
In step (2), the collocation method of eutectic solvent is as follows：First choline chloride and ethylene glycol are mixed, without water bar
Under part and stirring, heating is until form the clear solution of stable homogeneous, finally sealed is preserved.
The mol ratio of described choline chloride and ethylene glycol is 1:1～2.
Described heating-up temperature is 65～80 DEG C.
In step (2), after the Pericarpium Granati after step (1) is sieved is mixed with eutectic solvent, acidic materials control is added
The pH value of system is 3.0～3.2, after adding surfactant, then carries out Ultrasonic Heating extraction.
The present invention not only increases the surface tension of eutectic solvent by the pH value of addition acidic materials control system,
And it is more beneficial for the release of associativity polyphenols in Pericarpium Granati.
The present invention is compounded with eutectic solvent by adding surfactant, regulates and controls the microcosmic knot of eutectic solvent
Structure, changes density and the viscosity of eutectic solvent, produces cooperative effect, improve the dissolubility of polyphenols.
The preferred aqueous hydrochloric acid solution of described acidic materials or acetic acid aqueous solution, concentration are 0.8～1.2mol/L.
Described surfactant is Tweenses surfactant, surfactant and eutectic solvent in step (2)
Mass volume ratio example is 0.01～0.02g:1mL.
The mass volume ratio example of Pericarpium Granati after sieving in step (1) and eutectic solvent in step (2) is 0.75～
1.5g:1mL。
In step (2), Ultrasonic Heating extraction time is 15～25min, and Ultrasonic Heating Extracting temperature is 50～80 DEG C, ultrasound
Power is 90～110W.
In step (3), ethanol consumption is 0.1～0.2 times of eutectic solvent consumption in step (2).
In step (3) under the conditions of 10000rpm, 4 DEG C, 8～15min is centrifuged.
In step (3), the aperture of organic filter membrane is 0.22 μm, and organic filter membrane is commercially available prod, and preferably nylon of the invention is (poly-
Amide) microporous filter membrane.
Beneficial effects of the present invention are as follows：
(1) eutectic solvent of the present invention has the advantages that preparation process is simple, low cost, does not adopt poisonous and harmful solvent,
It is that actual production and application provide advantage；
(2) present invention using eutectic solvent extract Pericarpium Granati in polyphenols mild condition, it is easy to operate, to polyphenol
Class material extracts thorough；
(3) present invention makes Punica granatum L. processed side product Pericarpium Granati turn waste into wealth, for the effectively utilizes and deep layer of Punica granatum L. resource
Secondary Product processing is had great importance with exploitation.
Description of the drawings
Fig. 1 is the high-efficient liquid phase chromatogram of 1 Polyphenols standard substance mixed solution of embodiment.
Fig. 2 is the high-efficient liquid phase chromatogram of polyphenols in 2 Pericarpium Granati of embodiment.
Fig. 3 is the high-efficient liquid phase chromatogram of polyphenols in 3 Pericarpium Granati of embodiment.
Fig. 4 is the high-efficient liquid phase chromatogram of polyphenols in 4 Pericarpium Granati of embodiment.
Fig. 5 is the high-efficient liquid phase chromatogram of polyphenols in 5 Pericarpium Granati of embodiment.
Fig. 6 is the high-efficient liquid phase chromatogram of polyphenols in 6 Pericarpium Granati of embodiment.
Fig. 7 is the high-efficient liquid phase chromatogram of polyphenols in 7 Pericarpium Granati of embodiment.
Specific embodiment
With reference to embodiments the present invention is described further.
Embodiment 1
Configuration choline chloride, ethylene glycol eutectic solvent：
Mol ratio is 1:, under anhydrous condition and stirring, 70 DEG C of heating are until form homogeneous for 2 choline chloride and ethylene glycol
Stable clear solution, sealing preserve.
Eutectic solvent is used for the present invention process of Polyphenols standard substance, and by means of high performance liquid chromatography to Polyphenols
Material carries out Sensitive Detection.Comprise the following steps that；
(1) a certain amount of chlorogenic acid, the standard substance of two kinds of polyphenols of ellagic acid are weighed, adds ethanol dissolving to be made into green
Ortho acid, ellagic acid are 2.5 × 10-4The mixed solution of the polyphenols of mol/L；
(2) mixed solution obtained in measuring 2.0mL steps (1), adds 2.0mL eutectic solvents, vortex oscillation
15min, then 0.22 μm of organic membrane filtration of Jing；
(3) filtrate for obtaining step (2) carries out efficient liquid phase ultraviolet detection, chromatograph under conditions of wavelength is 276nm
Figure is shown in Fig. 1.
Embodiment 2
The eutectic solvent prepared using embodiment 1 is extracted to polyphenols in Pericarpium Granati sample, is then carried out
Efficient liquid phase ultraviolet detection.Comprise the following steps that：
(1) material prepares：Pericarpium Granati is dried, is crushed to 60～120 mesh, sieves；
(2) Ultrasonic Heating is extracted：1.0g Pericarpium Granatis after step (1) is sieved are put in 4mL centrifuge tubes, add 1mL low
Congruent melting solvent dissolves, in 65 DEG C, 90W power, and Ultrasonic Heating 22.5min, the polyphenols in Pericarpium Granati are extracted to low common
In molten solvent, the eutectic solvent containing polyphenols is obtained；
(3) centrifugation, dilution, filtration：First the eutectic solvent containing polyphenols that step (2) is obtained is existed
10000rpm, is centrifuged 10min under the conditions of 4 DEG C, takes 200 μ L centrifugal liquid, then adds 200 μ L ethanol dilutions in centrifugal liquid, finally
Organic membrane filtration of 0.22 μm of Jing.
Filtrate after filtration is carried out into high performance liquid chromatography separation UV-detector inspection under conditions of wavelength is 276nm
Survey, chromatogram is shown in Fig. 2.
With Pericarpium Granati quality g as calculating benchmark, under the conditions of this chlorogenic acid extracting yield be 28.249mg/g, ellagic acid yield
For 10.942mg/g.
Embodiment 3
The eutectic solvent prepared using embodiment 1 is extracted to polyphenols in Pericarpium Granati sample, is then carried out
Efficient liquid phase ultraviolet detection.Comprise the following steps that：
(1) material prepares：Pericarpium Granati is dried, is crushed to 60～120 mesh, sieves；
(2) Ultrasonic Heating is extracted：1.5g Pericarpium Granatis after step (1) is sieved are put in 4mL centrifuge tubes, add 1mL low
Congruent melting solvent dissolves, and in 80 DEG C, 100W power, Ultrasonic Heating 15min, the polyphenols in Pericarpium Granati are extracted to eutectic
In solvent, the eutectic solvent containing polyphenols is obtained；
(3) centrifugation, dilution, filtration：First the eutectic solvent containing polyphenols that step (2) is obtained is existed
10000rpm, is centrifuged 12min under the conditions of 4 DEG C, takes 200 μ L centrifugal liquid, then adds 200 μ L ethanol dilutions in centrifugal liquid, finally
Organic membrane filtration of 0.22 μm of Jing.
Filtrate after filtration is carried out into efficient liquid phase ultraviolet detection under conditions of wavelength is 276nm, chromatogram is shown in Fig. 3.
With Pericarpium Granati quality g as calculating benchmark, under the conditions of this chlorogenic acid extracting yield be 20.815mg/g, ellagic acid yield
For 9.854mg/g.
Embodiment 4
The eutectic solvent prepared using embodiment 1 is extracted to polyphenols in Pericarpium Granati sample, is then carried out
Efficient liquid phase ultraviolet detection.Comprise the following steps that：
(1) material prepares：Pericarpium Granati is dried, is crushed to 60～120 mesh, sieves；
(2) Ultrasonic Heating is extracted：1.25g Pericarpium Granatis after step (1) is sieved are put in 4mL centrifuge tubes, add 1mL low
Congruent melting solvent dissolves, and in 65 DEG C, 95W power, Ultrasonic Heating 15min, the polyphenols in Pericarpium Granati are extracted to eutectic
In solvent, the eutectic solvent containing polyphenols is obtained；
(3) centrifugation, dilution, filtration：First the eutectic solvent containing polyphenols that step (2) is obtained is existed
10000rpm, is centrifuged 15min under the conditions of 4 DEG C, takes 200 μ L centrifugal liquid, then adds 200 μ L ethanol dilutions in centrifugal liquid, finally
Organic membrane filtration of 0.22 μm of Jing.
Filtrate after filtration is carried out into efficient liquid phase ultraviolet detection under conditions of wavelength is 276nm, chromatogram is shown in Fig. 4.
With Pericarpium Granati quality g as calculating benchmark, under the conditions of this chlorogenic acid extracting yield be 24.355mg/g, ellagic acid yield
For 8.887mg/g.
Embodiment 5
The eutectic solvent prepared using embodiment 1 is extracted to polyphenols in Pericarpium Granati sample, is then carried out
Efficient liquid phase ultraviolet detection.Comprise the following steps that：
(1) material prepares：Pericarpium Granati is dried, is crushed to 60～120 mesh, sieves；
(2) Ultrasonic Heating is extracted：1.0g Pericarpium Granatis after step (1) is sieved are put in 4mL centrifuge tubes, add 1mL low
Congruent melting solvent dissolves, and the pH value for adding the aqueous hydrochloric acid solution control system that concentration is 1mol/L is 3.0, adds surfactant
0.01g Tween 80s, in 65 DEG C, 90W power, Ultrasonic Heating 22.5min, the polyphenols in Pericarpium Granati are extracted to eutectic
In solvent, the eutectic solvent containing polyphenols is obtained；
(3) centrifugation, dilution, filtration：First the eutectic solvent containing polyphenols that step (2) is obtained is existed
10000rpm, is centrifuged 10min under the conditions of 4 DEG C, takes 200 μ L centrifugal liquid, then adds 200 μ L ethanol dilutions in centrifugal liquid, finally
Organic membrane filtration of 0.22 μm of Jing.
Filtrate after filtration is carried out into high performance liquid chromatography separation UV-detector inspection under conditions of wavelength is 276nm
Survey, chromatogram is shown in Fig. 5.
With Pericarpium Granati quality g as calculating benchmark, under the conditions of this chlorogenic acid extracting yield be 31.802mg/g, ellagic acid yield
For 13.251mg/g.
Embodiment 6
The eutectic solvent prepared using embodiment 1 is extracted to polyphenols in Pericarpium Granati sample, is then carried out
Efficient liquid phase ultraviolet detection.Comprise the following steps that：
(1) material prepares：Pericarpium Granati is dried, is crushed to 60～120 mesh, sieves；
(2) Ultrasonic Heating is extracted：1.5g Pericarpium Granatis after step (1) is sieved are put in 4mL centrifuge tubes, add 1mL low
Congruent melting solvent dissolves, and the pH value for adding the aqueous hydrochloric acid solution control system that concentration is 1mol/L is 3.1, adds surfactant
0.02g Tween 80s, in 80 DEG C, 100W power, Ultrasonic Heating 15min, the polyphenols in Pericarpium Granati are extracted to eutectic
In solvent, the eutectic solvent containing polyphenols is obtained；
(3) centrifugation, dilution, filtration：First the eutectic solvent containing polyphenols that step (2) is obtained is existed
10000rpm, is centrifuged 12min under the conditions of 4 DEG C, takes 200 μ L centrifugal liquid, then adds 200 μ L ethanol dilutions in centrifugal liquid, finally
Organic membrane filtration of 0.22 μm of Jing.
Filtrate after filtration is carried out into efficient liquid phase ultraviolet detection under conditions of wavelength is 276nm, chromatogram is shown in Fig. 6.
With Pericarpium Granati quality g as calculating benchmark, under the conditions of this chlorogenic acid extracting yield be 29.517mg/g, ellagic acid yield
For 12.438mg/g.
Embodiment 7
The eutectic solvent prepared using embodiment 1 is extracted to polyphenols in Pericarpium Granati sample, is then carried out
Efficient liquid phase ultraviolet detection.Comprise the following steps that：
(1) material prepares：Pericarpium Granati is dried, is crushed to 60～120 mesh, sieves；
(2) Ultrasonic Heating is extracted：1.25g Pericarpium Granatis after step (1) is sieved are put in 4mL centrifuge tubes, add 1mL low
Congruent melting solvent dissolves, and the pH value for adding the aqueous hydrochloric acid solution control system that concentration is 1.2mol/L is 3.2, adds surfactant
0.01g Tween 80s, in 65 DEG C, 95W power, Ultrasonic Heating 15min, it is molten that the polyphenols in Pericarpium Granati are extracted to eutectic
In agent, the eutectic solvent containing polyphenols is obtained；
(3) centrifugation, dilution, filtration：First the eutectic solvent containing polyphenols that step (2) is obtained is existed
10000rpm, is centrifuged 15min under the conditions of 4 DEG C, takes 200 μ L centrifugal liquid, then adds 200 μ L ethanol dilutions in centrifugal liquid, finally
Organic membrane filtration of 0.22 μm of Jing.
Filtrate after filtration is carried out into efficient liquid phase ultraviolet detection under conditions of wavelength is 276nm, chromatogram is shown in Fig. 7.
With Pericarpium Granati quality g as calculating benchmark, under the conditions of this chlorogenic acid extracting yield be 36.731mg/g, ellagic acid yield
For 16.255mg/g.
Comparative example 1
Polyphenols in Pericarpium Granati sample are extracted in method of the prior art, comprised the following steps that：
(1) material prepares：Pericarpium Granati is dried, is crushed to 60～120 mesh, sieves；
(2) extract：1.0g Pericarpium Granatis after step (1) is sieved are put in 4mL centrifuge tubes, add 1mL pH's 3.1
60% ethanol solution, in 65 DEG C, 95W power, Ultrasonic Heating 15min；
(3) centrifugation, dilution, filtration：The solution that first step (2) is obtained is centrifuged 15min in 10000rpm under the conditions of 4 DEG C,
Take 200 μ L centrifugal liquid, most after 0.22 μm of Jing organic membrane filtration.
With Pericarpium Granati quality g as calculating benchmark, under the conditions of this chlorogenic acid extracting yield be 18.431mg/g, ellagic acid yield
For 7.207mg/g.
Claims (10)
1. a kind of method that employing eutectic solvent extracts polyphenols in Pericarpium Granati, it is characterised in that comprise the following steps：
(1) material prepares：Pericarpium Granati is dried, crushes, is sieved；
(2) Ultrasonic Heating is extracted：Pericarpium Granati after step (1) is sieved is mixed with eutectic solvent, and Jing Ultrasonic Heatings are extracted, stone
Polyphenols in pomegranate skin are extracted in eutectic solvent, obtain the eutectic solvent containing polyphenols；
(3) centrifugation, dilution, filtration：First by step (2) obtain containing polyphenols eutectic solvent centrifugation after, take from
Heart liquid, then add ethanol dilution in centrifugal liquid, most after the organic membrane filtrations of Jing.
2. the method that employing eutectic solvent according to claim 1 extracts polyphenols in Pericarpium Granati, its feature exist
In：In step (2), the collocation method of eutectic solvent is as follows：First choline chloride and ethylene glycol are mixed, in anhydrous condition and is stirred
Mix down, heating is until form the clear solution of stable homogeneous, finally sealed is preserved.
3. the method that employing eutectic solvent according to claim 2 extracts polyphenols in Pericarpium Granati, its feature exist
In：The mol ratio of choline chloride and ethylene glycol is 1:1～2.
4. the method that employing eutectic solvent according to claim 2 extracts polyphenols in Pericarpium Granati, its feature exist
In：Heating-up temperature is 65～80 DEG C.
5. the method that employing eutectic solvent according to claim 1 extracts polyphenols in Pericarpium Granati, its feature exist
In：In step (2), after the Pericarpium Granati after step (1) is sieved is mixed with eutectic solvent, acidic materials control system is added
PH value is 3.0～3.2, after adding surfactant, then carries out Ultrasonic Heating extraction.
6. the method that employing eutectic solvent according to claim 5 extracts polyphenols in Pericarpium Granati, its feature exist
In：Acidic materials are aqueous hydrochloric acid solution or acetic acid aqueous solution, and concentration is 0.8～1.2mol/L.
7. the method that employing eutectic solvent according to claim 5 extracts polyphenols in Pericarpium Granati, its feature exist
In：Surfactant is Tweenses surfactant, the mass volume ratio example of eutectic solvent in surfactant and step (2)
It is 0.01～0.02g:1mL.
8. the method that employing eutectic solvent according to claim 1 extracts polyphenols in Pericarpium Granati, its feature exist
In：Pericarpium Granati after sieving in step (1) is 0.75～1.5g with the mass volume ratio example of eutectic solvent in step (2):
1mL。
9. the method that employing eutectic solvent according to claim 1 extracts polyphenols in Pericarpium Granati, its feature exist
In：In step (2), Ultrasonic Heating extraction time is 15～25min, and Ultrasonic Heating Extracting temperature is 50～80 DEG C, and ultrasonic power is
90～110W.
10. the method that employing eutectic solvent according to claim 1 extracts polyphenols in Pericarpium Granati, its feature exist
In：In step (3), ethanol consumption is 0.1～0.2 times of eutectic solvent consumption in step (2)；In step (3) in
10000rpm, under the conditions of 4 DEG C, 8～15min is centrifuged.
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