CN111303108A - Method for extracting procyanidine A2 from litchi peels - Google Patents
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- CN111303108A CN111303108A CN202010141866.XA CN202010141866A CN111303108A CN 111303108 A CN111303108 A CN 111303108A CN 202010141866 A CN202010141866 A CN 202010141866A CN 111303108 A CN111303108 A CN 111303108A
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
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Abstract
The invention belongs to the technical field of extraction of plant active ingredients, and particularly relates to a method for extracting procyanidine A2 from litchi peels. The method recycles industrial waste litchi rind, after free procyanidine is extracted by ethanol solution, bound procyanidine is separated by hydrolysis by sodium hydroxide with specific concentration, and free and bound procyanidine A2 in litchi rind can be extracted to the maximum extent by column chromatography and chromatographic separation and purification, and the method is simple to operate and high in product yield, and the obtained procyanidine A2 can be applied to the fields of health-care food, cosmetics and the like, and is wide in application range. The method has important significance for improving the additional value of the litchi product and promoting the sustainable development of the industry.
Description
Technical Field
The invention belongs to the technical field of extraction of plant active ingredients. More particularly relates to a method for extracting procyanidin A2 from litchi peels.
Background
Litchi is a seasonal fruit which is a special product in south China and has the reputation of Lingnan fruit king. It is mature in high-temperature seasons in midsummer and difficult to store and keep fresh for a long time, so the litchi is mainly used in deep processing industry except fresh eating. The industrialization of litchi mainly takes cans, fruit juice and fruit wine as main materials, and a large amount of litchi rind is discarded as a byproduct, so that the litchi rind is not effectively developed and utilized. The litchi rind is rich in polyphenol compounds, particularly rich in A-type Procyanidins with few natural sources, wherein procyanidin dimer formed by polymerizing epicatechin, namely procyanidin A2(Procyanidins A2, PCA2), is rich in content, has various biological activities of resisting oxidation, reducing blood fat, reducing blood sugar, inhibiting urinary tract infection and the like, can be widely applied to industries of health-care food, cosmetics and the like, and has wide application prospect.
At present, the method for extracting procyanidine from litchi peels mainly adopts organic solvent extraction, for example, Chinese patent application CN107721965A discloses an extraction process of procyanidine from litchi peels. Therefore, a method which makes full use of litchi rind resources, can extract free or combined procyanidine A2 in litchi rind to the maximum extent and is simple to operate is urgently needed.
Disclosure of Invention
The invention aims to solve the technical problem of overcoming the defect and the defect that the combined procyanidine in litchi peel cannot be extracted by using an organic solvent in the prior art, and provides a method which can fully utilize litchi peel resources, can extract the free and combined procyanidine A2 in the litchi peel to the greatest extent and is simple to operate.
The invention aims to provide a method for extracting procyanidine A2 from litchi peels.
The above purpose of the invention is realized by the following technical scheme:
a method for extracting procyanidin A2 from litchi peels comprises the following steps:
extracting litchi rind with ethanol solution, centrifuging, hydrolyzing the residue in the bottom layer with sodium hydroxide, adjusting pH, centrifuging, mixing the supernatants, concentrating, separating with column, separating by chromatography, and drying.
Further, the method specifically comprises the following steps:
s1, freezing litchi peels, putting the frozen litchi peels into an ethanol solution, crushing the frozen litchi peels, extracting the crushed litchi peels at 45-50 ℃ for 2-3 hours, centrifuging the crushed litchi peels, adding the bottom-layer residue X into the ethanol solution, and extracting the bottom-layer residue X once again by the same method to obtain a combined supernatant A and a bottom-layer residue Y obtained after two times of extraction;
s2, adding the bottom residue Y obtained in the step S1 into a (2-4) mol/L sodium hydroxide solution with the mass volume ratio of 1 (10-15) g/ml under the protection of inert gas, shaking for hydrolysis for 2-4 h, adjusting the pH value to 2.0, centrifuging at 4 ℃, and separating to obtain a supernatant B;
s3, mixing the supernatant A obtained in the step S1 and the supernatant B obtained in the step S2, concentrating, eluting by macroporous resin, collecting 50% fractions, concentrating and drying to obtain a crude product of procyanidin A2;
s4, eluting and separating the crude product of the procyanidin A2 obtained in the step S3 by using a preparative chromatograph of a reversed-phase C18 chromatographic column, collecting 50% methanol fraction, concentrating and drying to obtain the procyanidin A2.
Further, in step S1, the ethanol solution has a volume percentage of 70 to 80%.
Further, in the step S1, the weight volume ratio of the litchi rind to the ethanol solution is 1 (15-20) g/ml.
Further, in step S2, the solvent for adjusting pH is hydrochloric acid with a concentration of 6 mol/L.
Further, in step S3, the macroporous resin is AB-8 macroporous resin.
Further, in step S3, the eluted eluents are ethanol solutions with 30%, 50% and 70% volume fractions in sequence.
Further, in step S4, a pressure of 2 to 3MPa is applied during elution and separation by the preparative chromatograph.
Further, in step S4, the eluted solution is 30%, 50%, 70% methanol aqueous solution by volume percentage.
The invention has the following beneficial effects:
according to the method, the industrial waste litchi rind is recycled, after free procyanidine is extracted by an ethanol solution, bound procyanidine is separated by hydrolysis by sodium hydroxide with a specific concentration, and then the free and bound procyanidine A2 in the litchi rind can be extracted to the maximum extent by column chromatography and chromatographic separation and purification.
Drawings
FIG. 1 is an HPLC chromatogram of crude procyanidin A2(PCA2) prepared in example 1 of the invention.
FIG. 2 is an HPLC chromatogram of procyanidin A2(PCA2) prepared in example 1 of the invention.
FIG. 3 is a first order mass spectrum of procyanidin A2(PCA2) prepared in example 1 of the invention.
FIG. 4 is a secondary mass spectrum of procyanidin A2(PCA2) prepared in example 1 of the invention.
Detailed Description
The invention is further described with reference to the drawings and the following detailed description, which are not intended to limit the invention in any way. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated.
Unless otherwise indicated, reagents and materials used in the following examples are commercially available.
Example 1A method for extracting procyanidin A2 from litchi rind
The method for extracting procyanidine A2 from litchi peels specifically comprises the following steps:
s1, freezing litchi rind, putting the frozen litchi rind into 70% ethanol solution by volume percentage, crushing the litchi rind and the ethanol solution to enable the weight-volume ratio of the litchi rind to the ethanol solution to be 1:20g/ml, extracting the litchi rind and the ethanol solution for 3 hours at 50 ℃, centrifuging the litchi rind and the ethanol solution, adding the bottom-layer residue X into the ethanol solution, extracting the mixture once again by the same method to obtain combined supernatant A and bottom-layer residue Y after two times of extraction, and storing the mixture at 4 ℃ for later use;
s2, adding 2mol/L sodium hydroxide solution with the mass volume ratio of 1:15g/ml into the bottom layer residue Y obtained in the step S1 under the protection of nitrogen, shaking for hydrolysis for 4 hours, adjusting the pH value to 2.0 by hydrochloric acid with the concentration of 6mol/L, centrifuging at 6000rpm for 10min at 4 ℃, and separating to obtain a supernatant B;
s3, combining the supernatant A obtained in the step S1 and the supernatant B obtained in the step S2, concentrating, feeding the mixture into AB-8 macroporous resin, eluting the mixture by using 30 percent, 50 percent and 70 percent ethanol solution in sequence, collecting 50 percent fractions, concentrating and drying the fractions to obtain a crude product of procyanidin A2;
s4, separating the crude product of the procyanidine A2 obtained in the step S3 by a preparative chromatograph of a reversed-phase C18 chromatographic column under the pressure of 3MPa, collecting 50% methanol fraction as eluent which is 30%, 50% and 70% methanol water solution by volume percentage, concentrating and drying to obtain the procyanidine A2.
Example 2A method for extracting procyanidin A2 from litchi rind
The method for extracting procyanidine A2 from litchi peels specifically comprises the following steps:
s1, freezing litchi rind, putting the frozen litchi rind into 70% ethanol solution by volume percentage, crushing the litchi rind and the ethanol solution to enable the weight-volume ratio of the litchi rind to the ethanol solution to be 1:20g/ml, extracting the litchi rind and the ethanol solution for 3 hours at 50 ℃, centrifuging the litchi rind and the ethanol solution, adding the bottom-layer residue X into the ethanol solution, extracting the mixture once again by the same method to obtain combined supernatant A and bottom-layer residue Y after two times of extraction, and storing the mixture at 4 ℃ for later use;
s2, adding 3mol/L sodium hydroxide solution with the mass volume ratio of 1:15g/ml into the bottom layer residue Y obtained in the step S1 under the protection of nitrogen, shaking for hydrolysis for 3h, adjusting the pH value to 2.0 by hydrochloric acid with the concentration of 6mol/L, centrifuging at 6000rpm at 4 ℃ for 10min, and separating to obtain a supernatant B;
s3, combining the supernatant A obtained in the step S1 and the supernatant B obtained in the step S2, concentrating, feeding the mixture into AB-8 macroporous resin, eluting the mixture by using 30 percent, 50 percent and 70 percent ethanol solution in sequence, collecting 50 percent fractions, concentrating and drying the fractions to obtain a crude product of procyanidin A2;
s4, separating the crude product of the procyanidine A2 obtained in the step S3 by a preparative chromatograph of a reversed-phase C18 chromatographic column under the pressure of 2MPa, wherein the eluent is 30 percent, 50 percent and 70 percent of methanol aqueous solution, collecting 50 percent of methanol fraction, concentrating and drying to obtain the procyanidine A2.
Example 3A method for extracting procyanidin A2 from litchi rind
The method for extracting procyanidine A2 from litchi peels specifically comprises the following steps:
s1, freezing litchi rind, putting the frozen litchi rind into 70% ethanol solution by volume percentage, crushing the litchi rind and the ethanol solution to enable the weight-volume ratio of the litchi rind to the ethanol solution to be 1:15g/ml, extracting the litchi rind and the ethanol solution for 3 hours at 50 ℃, centrifuging the litchi rind and the ethanol solution, adding the bottom-layer residue X into the ethanol solution, extracting the mixture once again by the same method to obtain combined supernatant A and bottom-layer residue Y after two times of extraction, and storing the mixture at 4 ℃ for later use;
s2, adding 4mol/L sodium hydroxide solution with the mass volume ratio of 1:15g/ml into the bottom layer residue Y obtained in the step S1 under the protection of nitrogen, shaking for hydrolysis for 2h, adjusting the pH value to 2.0 by hydrochloric acid with the concentration of 6mol/L, centrifuging at 6000rpm at 4 ℃ for 10min, and separating to obtain a supernatant B;
s3, combining the supernatant A obtained in the step S1 and the supernatant B obtained in the step S2, concentrating, feeding the mixture into AB-8 macroporous resin, eluting the mixture by using 30 percent, 50 percent and 70 percent ethanol solution in sequence, collecting 50 percent fractions, concentrating and drying the fractions to obtain a crude product of procyanidin A2;
s4, separating the crude product of the procyanidine A2 obtained in the step S3 by a preparative chromatograph of a reversed-phase C18 chromatographic column under the pressure of 3MPa, collecting 50% methanol fraction as eluent which is 30%, 50% and 70% methanol water solution by volume percentage, concentrating and drying to obtain the procyanidine A2.
Comparative example 1 method for extracting procyanidin A2 from litchi peels
The method for extracting procyanidine A2 from litchi peels specifically comprises the following steps:
s1, freezing litchi rind, putting the frozen litchi rind into 70% ethanol solution by volume percentage, crushing the litchi rind and the ethanol solution to enable the weight-volume ratio of the litchi rind to the ethanol solution to be 1:20g/ml, extracting the litchi rind and the ethanol solution for 3 hours at 50 ℃, centrifuging the litchi rind and the ethanol solution, adding the bottom-layer residue X into the ethanol solution, extracting the mixture once again by the same method to obtain combined supernatant A and bottom-layer residue Y after two times of extraction, and storing the mixture at 4 ℃ for later use;
s2, adding 6mol/L sodium hydroxide solution with the mass volume ratio of 1:15g/ml into the bottom layer residue Y obtained in the step S1 under the protection of nitrogen, shaking for hydrolysis for 2h, adjusting the pH value to 2.0 by using 6mol/L hydrochloric acid, centrifuging at 6000rpm at 4 ℃ for 10min, and separating to obtain a supernatant B;
s3, combining the supernatant A obtained in the step S1 and the supernatant B obtained in the step S2, concentrating, feeding the mixture into AB-8 macroporous resin, eluting the mixture by using 30 percent, 50 percent and 70 percent ethanol solution in sequence, collecting 50 percent fractions, concentrating and drying the fractions to obtain a crude product of procyanidin A2;
s4, separating the crude product of the procyanidine A2 obtained in the step S3 by a preparative chromatograph of a reversed-phase C18 chromatographic column under the pressure of 3MPa, collecting 50% methanol fraction as eluent which is 30%, 50% and 70% methanol water solution by volume percentage, concentrating and drying to obtain the procyanidine A2.
Comparative example 1 is different from example 1 in that the concentration of the sodium hydroxide solution used in step S2 is 6 mol/L.
Comparative example 2 method for extracting procyanidin A2 from litchi peels
The method for extracting procyanidine A2 from litchi peels specifically comprises the following steps:
s1, freezing litchi rind, putting the frozen litchi rind into 70% ethanol solution by volume percentage, crushing the litchi rind and the ethanol solution to enable the weight-volume ratio of the litchi rind to the ethanol solution to be 1:20g/ml, extracting the litchi rind and the ethanol solution for 3 hours at 50 ℃, centrifuging the litchi rind and the ethanol solution, adding the bottom-layer residue X into the ethanol solution, extracting the mixture once again by the same method to obtain combined supernatant A and bottom-layer residue Y after two times of extraction, and storing the mixture at 4 ℃ for later use;
s2, concentrating the supernatant A obtained in the step S1, loading the concentrated supernatant A on AB-8 macroporous resin, eluting the concentrated supernatant A with 30% by volume, 50% by volume and 70% by volume of ethanol solution in sequence, collecting 50% fractions, concentrating and drying the fractions to obtain a crude product of procyanidine A2;
s3, separating the crude product of procyanidine A2 obtained in the step S2 by a preparative chromatograph of a reversed-phase C18 chromatographic column under the pressure of 3MPa, collecting 50% methanol fraction as eluent with the volume percentage of 30%, 50% and 70% methanol water solution, concentrating and drying to obtain procyanidine A2.
Comparative example 2 differs from example 1 in that no alkaline hydrolysis was carried out.
Experimental example 1 HPLC analysis and structural identification of UPLC-Q-TOF-MS
Taking example 1 as an example, HPLC analysis and UPLC-Q-TOF-MS structural identification are performed on the prepared crude procyanidin a2 product and procyanidin a2 sample, and the results are shown in fig. 1 to 4, and the results of examples 2 to 3 are similar to those of example 1.
Wherein, HPLC conditions are as follows: shimadzu LC-20 system, SPD-20A detector; a chromatographic column:
c18 (4.6X 250mm, 5 μm), column temperature 30 deg.C, sample size 20 μ L, and detection wavelength 280 nm; mobile phase a was 0.4% acetic acid aqueous solution, mobile phase B was acetonitrile, flow rate: 1.00mL/min, gradient elution: 0-40 min, 5% -35% B; for 40-45 min, 35-50% of B; 45-50 min, 50-80% B; 50-60 min, 5% -5% of B, and balancing the mobile phase A for 10 min.
Ultra performance liquid chromatography-quadrupole-time of flight mass spectrometer (UPLC-Q-TOF-MS) conditions: agilent system, model: 1290-6540; mass spectrum conditions: in an ESI negative ion source mode, the capillary voltage is 3500V, the fragment voltage is 175V, the atomization pressure is 65Psi, the drying gas temperature is 300 ℃, and a primary mass spectrum and a secondary mass spectrum are collected in a mass spectrum ion range of m/z 100-1200. The chromatographic conditions were as above.
As can be seen from fig. 1-2, in the HPLC chromatogram of the crude procyanidin a2 product, a large amount of other impurities exist in addition to procyanidin a2, and after certain refining, procyanidin a2 impurities are significantly reduced, and the purity is high.
As can be seen from FIGS. 3 to 4, the molecular weight of the procyanidin A2 sample prepared in example 1 of the invention is 576.11, and the molecular ion peak is 575.11[ M-H ]]-The fragment peaks mainly comprise 285.04, 423.07 and the like, and the comparison with the procyanidin A2 standard proves that the sample prepared in the example 1 of the invention is compoundedThe extract is procyanidin A2.
Experimental example 2 yield measurement
The yield and purity of the procyanidin A2 prepared in the examples 1-3 and the comparative examples 1-2 are measured and calculated, and the results are shown in the table 1.
Table 1 yield of procyanidin a2
| Group of | Yield (%) | Purity (%) |
| Example 1 | 0.57±0.05 | 90.53±7.51 |
| Example 2 | 0.53±0.07 | 89.91±5.23 |
| Example 3 | 0.51±0.05 | 90.82±9.21 |
| Comparative example 1 | 0.41±0.08 | 90.31±3.38 |
| Comparative example 2 | 0.37±0.02 | 90.70±3.25 |
As can be seen from Table 1, the procyanidin A2 prepared in the embodiments 1 to 3 of the invention has higher yield, while the extraction method is changed in the comparative examples 1 to 2, so that the yield is obviously reduced.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (9)
1. A method for extracting procyanidine A2 from litchi peels is characterized by comprising the following steps:
extracting litchi rind with ethanol solution, centrifuging, hydrolyzing the residue in the bottom layer with sodium hydroxide, adjusting pH, centrifuging, mixing the supernatants, concentrating, separating with column, separating by chromatography, and drying.
2. The method according to claim 1, characterized in that it comprises in particular the steps of:
s1, freezing litchi peels, putting the frozen litchi peels into an ethanol solution, crushing the frozen litchi peels, extracting the crushed litchi peels at 45-50 ℃ for 2-3 hours, centrifuging the crushed litchi peels, adding the bottom-layer residue X into the ethanol solution, and extracting the bottom-layer residue X once again by the same method to obtain a combined supernatant A and a bottom-layer residue Y obtained after two times of extraction;
s2, adding the bottom residue Y obtained in the step S1 into a (2-4) mol/L sodium hydroxide solution with the mass volume ratio of 1 (10-15) g/ml under the protection of inert gas, shaking for hydrolysis for 2-4 h, adjusting the pH value to 2.0, centrifuging at 4 ℃, and separating to obtain a supernatant B;
s3, mixing the supernatant A obtained in the step S1 and the supernatant B obtained in the step S2, concentrating, eluting by macroporous resin, collecting 50% fractions, concentrating and drying to obtain a crude product of procyanidin A2;
s4, eluting and separating the crude product of the procyanidin A2 obtained in the step S3 by using a preparative chromatograph of a reversed-phase C18 chromatographic column, collecting 50% methanol fraction, concentrating and drying to obtain the procyanidin A2.
3. The method according to claim 2, wherein in step S1, the volume percentage of the ethanol solution is 70-80%.
4. The method as claimed in claim 2, wherein in step S1, the weight/volume ratio of litchi rind to ethanol solution is 1 (15-20) g/ml.
5. The method according to claim 2, wherein the solvent for adjusting pH in step S2 is hydrochloric acid with a concentration of 6 mol/L.
6. The method of claim 2, wherein in step S3, the macroporous resin is an AB-8 macroporous resin.
7. The method according to claim 2, wherein in step S3, the eluted eluents are sequentially 30%, 50%, 70% ethanol solution by volume fraction.
8. The method of claim 2, wherein in step S4, a pressure of 2 to 3MPa is applied during elution and separation by the preparative chromatograph.
9. The method according to claim 2, wherein in step S4, the eluted solution is 30-70% by volume of methanol aqueous solution.
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