CN111675640B - Method for separating and preparing high-purity zeaxanthin - Google Patents
Method for separating and preparing high-purity zeaxanthin Download PDFInfo
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Abstract
The invention provides a method for separating and preparing high-purity zeaxanthin, which utilizes an alkaline lower phase solvent as a mobile phase of a countercurrent chromatography to realize synchronous hydrolysis and separation of zeaxanthin dipalmitate and zeaxanthin monopalmitate in the separation process, thereby overcoming the defects of complicated saponification and hydrolysis operation and denaturation caused by long-time exposure of zeaxanthin in medlar in the separation process of the zeaxanthin. In addition, the solubility and the selectivity of the lower phase solvent relative to the zeaxanthin in the HSCCC two-phase solvent system are increased through the hydrogen bonding effect of the eutectic solvent, and a feasible scheme is provided for the rapid, continuous and efficient preparation of the high-purity zeaxanthin.
Description
Technical Field
The invention belongs to the technical field of natural product separation, and particularly relates to a separation and preparation method of high-purity zeaxanthin.
Background
Zeaxanthin (Zeaxanthin,3, 3' -dihydroxy- β -carotene), also known as Zeaxanthin, belongs to the isoprenoid class and is an oxygen-containing carotenoid. The zeaxanthin has the specificity of absorbing blue light in ultraviolet rays, so that the damage of the blue light to a retina is avoided, and the asthenopia can be relieved. The human body cannot synthesize zeaxanthin by itself and must be supplemented by ingesting an article containing zeaxanthin.
Lycium chinense is the plant with the highest zeaxanthin content. Researches show that the eyesight improving effect of the medlar has a direct relation with zeaxanthin, and more researchers use the zeaxanthin as a medlar pigment to play a main index of the physiological activity of improving eyesight so as to measure the quality of a medlar pigment extract. Meanwhile, the zeaxanthin is also a main index component of the food additive zeaxanthin and a new food raw material zeaxanthin. Therefore, the extraction and separation of high-purity zeaxanthin (HPLC is more than or equal to 98%) for the reference substance of quality detection of zeaxanthin-related products becomes a hotspot of research in the field.
A large amount of carotenoid substances are accumulated in the ripe fruits of the Ningxia wolfberry, particularly the content of zeaxanthin dipalmitate (zeaxanthin dipalmitate) is most abundant in the Ningxia wolfberry, accounts for more than 56-75% of the total amount of the pigment substances, and in addition, the mature fruits of the Ningxia wolfberry also contain a small amount of zeaxanthin, zeaxanthin monopalmitate, beta-carotene and beta-cryptoxanthin. Therefore, the Chinese wolfberry is one of the main raw materials of the zeaxanthin. The high-purity zeaxanthin (HPLC is more than or equal to 98%) separated from the medlar needs to be converted into the zeaxanthin after the zeaxanthin dipalmitate and the zeaxanthin monopalmitate in the medlar are saponified and hydrolyzed on one hand, and needs to be separated from the isomeric lutein of the zeaxanthin on the other hand.
The existing separation and purification technologies for zeaxanthin mainly comprise a solvent extraction method, a membrane separation method, a column chromatography technology, a macroporous adsorption resin separation technology and a high performance liquid chromatography technology.
Chinese patent publication No. CN 106543769 a discloses a method for extracting a carotenoid monomer pigment mainly containing zeaxanthin from lycium barbarum, which comprises the steps of saponifying and extracting zeaxanthin in lycium barbarum with an alkali-containing ethanol solution, and separating, purifying and refining a zeaxanthin extract with acid, ethanol and tetrahydrofuran aqueous solutions of different concentrations to obtain zeaxanthin, but the method is difficult to separate and remove the isomeric form of zeaxanthin, so that the content of zeaxanthin can only reach about 80%, and the method cannot be used for preparing a reference substance.
Chinese patent publication No. CN105503681A discloses a method for preparing high-purity lycium ruthenicum zeaxanthin palmitate from lycium ruthenicum zeaxanthin palmitate, which comprises using petroleum ether and ethanol as solvent systems, separating by alumina column chromatography, extracting with ethyl acetate, and extracting with supercritical carbon dioxide to obtain zeaxanthin palmitate with purity of 90% or more. The method respectively utilizes column chromatography, solvent extraction and carbon dioxide extraction, has the advantages of complex operation, high cost, and no continuous separation and preparation, is a separation and preparation method of ester components, and is not suitable for separation and preparation of high-purity zeaxanthin. Chinese patent publication No. CN 108586306a discloses a method for separating lutein and zeaxanthin by ionic liquid enhanced extraction, which utilizes different types of ionic liquids, biodiesel, n-hexane and water to extract and back-extract the mixture of lutein and zeaxanthin to obtain high-purity lutein and zeaxanthin respectively. However, this method is only suitable for the separation and purification of two monomer mixtures with simple components, and is not suitable for the separation and purification of zeaxanthin in complex systems such as lycium barbarum extract.
Disclosure of Invention
The invention aims to provide a method for separating and preparing high-purity zeaxanthin, thereby making up for the defects of the prior art.
The method for separating and preparing the high-purity zeaxanthin provided by the invention comprises the following steps:
1) drying fructus Lycii, and pulverizing to obtain fructus Lycii powder;
the drying is to ensure that the moisture content is less than 5 percent,
2) putting the medlar powder into a subcritical extraction kettle, and adjusting the vacuum degree to-0.05 MPa;
3) extracting with butane solvent at 45 deg.C under 0.25MPa, removing solvent, and collecting the fructus Lycii oil extract;
4) taking a eutectic solvent as an additive, taking a two-phase solvent system formed by petroleum ether, hexane, ethanol, an alkaline aqueous solution and the eutectic solvent as a solvent system of high-speed countercurrent chromatography (HSCCC), pumping an upper phase/lower phase of the solvent system into an HSCCC spiral pipe column, dissolving a medlar oil extract by using the solvent system after the two phases in the spiral pipe column reach hydrodynamic balance, injecting the medlar oil extract into the HSCCC spiral pipe column through a sample valve, and continuously mixing the alkaline lower phase solvent and an upper phase solvent containing zeaxanthin components by using the high-speed rotation of the HSCCC to realize the hydrolysis of zeaxanthin dipalmitate and zeaxanthin monopalmitate and the separation of the zeaxanthin after the hydrolysis;
5) monitoring a chromatographic peak of zeaxanthin at a wavelength of 445nm by using an HSCCC ultraviolet visible wavelength detector, merging eluent containing the zeaxanthin according to an HSCCC chromatogram, adjusting the pH to 6.7-7.2 by using hydrochloric acid, recovering the solvent under reduced pressure, separating out zeaxanthin crystals, cleaning the zeaxanthin crystals, removing impurities on the surfaces of the crystals, and freeze-drying to obtain the high-purity zeaxanthin.
The Eutectic solvent (DES) is a Eutectic mixture formed by combining a hydrogen bond acceptor and a hydrogen bond donor through hydrogen bonding;
wherein the hydrogen bond donor is carboxylic acid, amide, and polyalcohol, and comprises at least one of urea, ethylene glycol, 1, 4-butanediol, 1, 3-butanediol, glycerol, lactic acid, oxalic acid, glucose, acetic acid, and propionic acid;
the hydrogen bond acceptor is quaternary ammonium salt, such as at least one of choline chloride, betaine, acetyl choline chloride, tetrabutyl ammonium bromide, ammonium chloride, methyl triphenyl phosphonium bromide and benzyl triphenyl phosphonium chloride,
wherein the molar ratio of the hydrogen bond acceptor to the hydrogen bond donor is 1:1-1: 2.
In the two-phase solvent system consisting of the petroleum ether, the normal hexane, the ethanol, the alkaline aqueous solution and the eutectic solvent, the concentration of the eutectic solvent is 0.5-5%, preferably 0.5-1%;
wherein the volume ratio of the petroleum ether/n-hexane/ethanol/alkaline aqueous solution is (3-6) to (5-10) to (1-4),
preferably a solvent system containing 1 percent of DES, and the volume ratio of petroleum ether/n-hexane/ethanol/alkaline aqueous solution is 3:3 (5-6): (1-2).
The alkaline aqueous solution is composed of sodium hydroxide or potassium hydroxide aqueous solution, and the mass concentration is 0.5-10g/ml, preferably 8-10 g/ml.
The loading concentration of the medlar oil extract is 0.5-5g/ml, preferably 2 g/ml.
The separation temperature of the HSCCC is 25-50 ℃, preferably 35 ℃.
The separation mode of the HSCCC is a reverse phase mode or a normal phase mode, preferably the reverse phase mode, wherein the upper phase of the solvent system is a stationary phase, and the lower phase is a mobile phase.
And 5) cleaning with water, petroleum ether or n-hexane.
The invention utilizes an alkaline lower phase solvent as a mobile phase of the countercurrent chromatography to realize the synchronous hydrolysis and separation of the zeaxanthin dipalmitate and the zeaxanthin monopalmitate in the separation process, thereby overcoming the defects of complicated saponification and hydrolysis operation and denaturation caused by long-time exposure of the zeaxanthin in the separation process of the zeaxanthin in the medlar. In addition, the solubility and the selectivity of the lower phase solvent relative to the zeaxanthin in the HSCCC two-phase solvent system are increased through the hydrogen bonding effect of the eutectic solvent, and a feasible scheme is provided for the rapid, continuous and efficient preparation of the high-purity zeaxanthin.
Drawings
FIG. 1-1 shows an HPLC chromatogram of an oil extract of Lycium barbarum obtained by subcritical extraction;
FIGS. 1-2 HSCCC separation chromatograms of an oil extract of Lycium barbarum;
FIGS. 1-3 are HPLC chromatograms of isolated zeaxanthin monomers.
Detailed Description
The invention takes medlar as raw material, extracts of zeaxanthin and derivatives thereof are obtained by subcritical extraction, the extracts are dissolved by a high-speed countercurrent (HSCCC) solvent system and then injected into the HSCCC, and the synchronous saponification and separation preparation of the zeaxanthin derivatives are realized by utilizing an alkaline solvent system containing a eutectic solvent. The method established by the invention is simple and rapid, and can realize continuous powder separation; and high-purity zeaxanthin can be obtained. The whole separation process is a closed and light-proof system, and the risks that the zeaxanthin is easily oxidized and is denatured by illumination in the traditional chromatographic separation process are overcome.
The present invention will be described in detail with reference to examples.
Example 1
(1) Drying fructus Lycii in oven until water content is less than 5%, pulverizing, and sieving with 40 mesh sieve.
(2) Weighing 0.5kg of medlar powder, putting into a subcritical extraction kettle, and adjusting the vacuum degree to-0.05 MPa.
(3) Adding 2.5L butane for extraction at 45 deg.C under 0.25MPa for 2 times each for 45 min. After extraction, desolventizing, collecting 11.6g of medlar oil extract, and obtaining an HPLC chromatogram which is detailed in 1-1.
(4) A two-phase solvent system formed by petroleum ether, n-hexane, ethanol and 8% potassium hydroxide aqueous solution (the volume ratio is 3:3:5:1) and a eutectic solvent is a solvent system of high-speed countercurrent chromatography (HSCCC). Specifically, 10g of choline chloride: the eutectic solvent formed by ethylene glycol (1:2) was added to 1000mL of a mixed solvent made of petroleum ether, n-hexane, ethanol, and 8% aqueous potassium hydroxide (in a volume ratio of 3:3:5:1) to prepare a two-phase solvent system.
Pumping the upper phase of the two-phase solvent system into an HSCCC spiral pipe column at a speed of 20ml/min, and adjusting the temperature of the system to 35 ℃ and the rotating speed of the HSCCC to 700 r/min after the spiral pipe column is completely filled with the solvent; the lower phase of the biphasic solvent system was then pumped into the spiral column at 2ml/min according to the "head → tail" elution mode. After hydrodynamic equilibrium between the two phases in the spiral column (no upper phase solvent run out), 5g of the wolfberry oil extract was dissolved using a 10ml solvent system (5 ml upper phase, 5ml lower phase) and injected through the sample valve into the HSCCC spiral column.
Adjusting the detection wavelength of an ultraviolet and visible wavelength detector of HSCCC to 445nm, wherein the chromatogram is detailed in 1-2, collecting the eluate according to 5 min/bottle, merging the eluates of 170min to 190min according to the chromatogram of HSCCC, adjusting the pH to 7.1 by using hydrochloric acid, recovering the solvent under reduced pressure to separate out zeaxanthin crystals, washing zeaxanthin respectively by using 20ml of petroleum ether and water for several times, and discarding. After freeze-drying, 100mg of zeaxanthin is obtained.
The purity of zeaxanthin detected by HPLC is 98.8%, and the HPLC chromatogram of zeaxanthin monomer is detailed in 1-3. The yield of the zeaxanthin reaches 75 percent.
The HPLC chromatographic conditions were as follows: YMC C30(4.6 mm. times.250 mm, 5 μm); the mobile phase is dichloromethane, acetonitrile and methanol (2: 3: 5); the detection wavelength is 450 nm; the column temperature is 30 ℃; the injection volume is 20. mu.L.
Example 2
(1) Drying fructus Lycii in oven until water content is less than 5%, pulverizing, and sieving with 40 mesh sieve.
(2) Weighing 0.25kg of medlar powder, putting into a subcritical extraction kettle, and adjusting the vacuum degree to-0.05 MPa.
(3) Adding 1.25L butane to extract at 45 deg.C under 0.25MPa for 2 times each for 45 min. After extraction, desolventizing is carried out, and 5.5g of medlar oil extract is collected.
(4) A two-phase solvent system formed by petroleum ether, n-hexane, ethanol and 8% potassium hydroxide aqueous solution (3:3:5:1, V/V/V) is a solvent system of high-speed countercurrent chromatography (HSCCC). (in this example, eutectic solvent was not added)
The upper phase of the solvent system was pumped into the HSCCC spiral column at 20ml/min, after the spiral column was completely filled with solvent, the system temperature was adjusted to 35 ℃, the HSCCC speed was adjusted to 700 rpm, and the lower phase was pumped into the spiral column at 2ml/min according to the "head → tail" elution profile. After hydrodynamic equilibrium between the two phases in the spiral column (no upper phase solvent run out), 5g of the wolfberry oil extract was dissolved using a 10ml solvent system (5 ml upper phase, 5ml lower phase) and injected through the sample valve into the HSCCC spiral column.
Adjusting the detection wavelength of an ultraviolet visible wavelength detector of HSCCC to 445nm, collecting the eluate according to 5 min/bottle, combining the eluates of 160min to 195min according to the chromatogram of HSCCC, adjusting pH to 6.95 with hydrochloric acid, recovering solvent under reduced pressure to obtain zeaxanthin, washing zeaxanthin with 20ml of petroleum ether and water for several times, respectively, and discarding. Freeze drying to obtain zeaxanthin 110 mg.
In this example, compared with example 1, eutectic solvent was not used as an additive, thereby affecting the separation efficiency between zeaxanthin and lutein with similar structure, and the separated zeaxanthin contains part of lutein components, and the purity of zeaxanthin detected by HPLC was 89.8%, which is lower than that of zeaxanthin in example 1.
Claims (8)
1. A method for separating and preparing zeaxanthin is characterized by comprising the following steps:
1) drying fructus Lycii, and pulverizing to obtain fructus Lycii powder;
2) putting the medlar powder into a subcritical extraction kettle, and adjusting the vacuum degree to-0.05 MPa;
3) extracting with butane solvent at 45 deg.C under 0.25MPa,
desolventizing after extraction is finished, and collecting the medlar oil extract;
4) taking a eutectic solvent as an additive, taking a two-phase solvent system formed by petroleum ether, hexane, ethanol, an alkaline aqueous solution and the eutectic solvent as a solvent system of high-speed countercurrent chromatography (HSCCC), pumping an upper phase/lower phase of the solvent system into an HSCCC spiral pipe column, dissolving a medlar oil extract by using the solvent system after the two phases in the spiral pipe column reach hydrodynamic balance, injecting the medlar oil extract into the HSCCC spiral pipe column through a sample valve, and continuously mixing the alkaline lower phase solvent and an upper phase solvent containing zeaxanthin components by using the high-speed rotation of the HSCCC to realize the hydrolysis of zeaxanthin dipalmitate and zeaxanthin monopalmitate and the separation of the zeaxanthin after the hydrolysis;
5) monitoring a chromatographic peak of zeaxanthin at a wavelength of 445nm by using an HSCCC ultraviolet visible wavelength detector, merging eluents containing zeaxanthin according to an HSCCC chromatogram, adjusting the pH to 6.7-7.2 by using hydrochloric acid, recovering a solvent under reduced pressure, separating out zeaxanthin crystals, cleaning the zeaxanthin crystals, removing impurities on the surfaces of the crystals, and freeze-drying to obtain high-purity zeaxanthin;
the eutectic solvent is a eutectic mixture formed by combining a hydrogen bond acceptor and a hydrogen bond donor through hydrogen bond action, and the hydrogen bond donor is ethylene glycol; the hydrogen bond receptor is choline chloride; wherein the mol ratio of the choline chloride to the ethylene glycol is 1: 2.
2. The method of claim 1, wherein the drying in 1) is carried out to a moisture content of less than 5%.
3. The method according to claim 1, wherein the concentration of the eutectic solvent in the two-phase solvent system of 3) is 0.5-5%.
4. The method as claimed in claim 1, wherein the volume ratio of the petroleum ether, the n-hexane, the ethanol and the alkaline aqueous solution in 4) is 3-6:3-6:5-10: 1-4.
5. The method as claimed in claim 1, wherein the volume ratio of the petroleum ether, the n-hexane, the ethanol and the alkaline aqueous solution in 4) is 3:3:5-6: 1-2.
6. The method of claim 1, wherein the alkaline aqueous solution in 4) is an aqueous solution of sodium hydroxide or potassium hydroxide with a mass concentration of 0.5-10 g/ml.
7. The method of claim 1, wherein said HSCCC separation temperature in 4) is from 25 ℃ to 50 ℃.
8. The method of claim 1, wherein the washing of the zeaxanthin crystals in 5) is with water, petroleum ether or n-hexane.
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| CN114292527B (en) * | 2021-12-28 | 2022-10-04 | 中国科学院兰州化学物理研究所 | Method for extracting maize yellow component from maize |
| CN114656386A (en) * | 2022-04-19 | 2022-06-24 | 中国科学院兰州化学物理研究所 | A method for extracting lycine red pigment from fructus Lycii |
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