CN115650942A - Method for extracting, separating and purifying 8-isopentenyl naringenin from hops - Google Patents
Method for extracting, separating and purifying 8-isopentenyl naringenin from hops Download PDFInfo
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- CN115650942A CN115650942A CN202211313437.1A CN202211313437A CN115650942A CN 115650942 A CN115650942 A CN 115650942A CN 202211313437 A CN202211313437 A CN 202211313437A CN 115650942 A CN115650942 A CN 115650942A
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- 238000000034 method Methods 0.000 title claims abstract description 52
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- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 description 1
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- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
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- 235000008209 xanthohumol Nutrition 0.000 description 1
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- 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
- B01D11/0288—Applications, solvents
-
- 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
- B01D11/0203—Solvent extraction of solids with a supercritical fluid
-
- 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
- B01D11/028—Flow sheets
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0488—Flow sheets
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/265—Adsorption chromatography
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
- B01D9/0013—Crystallisation cooling by heat exchange by indirect heat exchange
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C3/00—Treatment of hops
- C12C3/04—Conserving; Storing; Packing
- C12C3/08—Solvent extracts from hops
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
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Abstract
The invention provides a method for extracting, separating and purifying 8-isopentenyl naringenin from hops, which comprises the following steps: s1, performing first extraction on a hop raw material by supercritical carbon dioxide to obtain first hop raffinate; s2, extracting the first hop raffinate by using an extracting agent to obtain an extracting solution; the extractant comprises water and a first solvent, the first solvent is selected from one of methanol, ethanol, acetone and ethyl acetate, and the volume mixing ratio of the water to the first solvent is 1:0.05 to 1; s3, performing second extraction on the extracting solution through an extracting agent to obtain second extracting solution; the extractant comprises the following components according to the weight ratio of 0.5: 0.1-5 volume ratio of one or two of n-butyl alcohol, isobutyl alcohol, ethyl acetate, n-hexane, cyclohexane and petroleum ether; and S4, carrying out column chromatography on the second extract liquor, and purifying to obtain the 8-isopentenyl naringenin. Realizes the extraction, separation and purification of the high-purity 8-isopentenyl naringenin from the hops.
Description
Technical Field
The invention relates to the field of biological medicine, in particular to a method for extracting, separating and purifying 8-isopentenyl naringenin from hops.
Background
8-Prenylnaringenin (8-Prenylnaringenin, 8PN for short) is a prenylflavone with estrogenic action found in hops, and the 8PN is reported to be the most potential phytoestrogen found so far. In vivo and in vitro studies show that 8PN has stronger estrogen action, can exert the effect under low dose, has stronger action than found phytoestrogens such as soybean isoflavone, genistein and the like, can effectively relieve various symptoms of women in menopause, has weak side effects, and is considered as a novel phytoestrogen for replacing hormone substitution therapy. Besides the estrogen action, 8-isopentenyl naringenin also has other effects of preventing cancer, preventing osteoporosis, inhibiting vascular proliferation, resisting oxidation, etc.
At present, the research at home and abroad mainly focuses on the extraction and separation of the oil ester components and the xanthohumol of the hops, but the research on extracting the beneficial component 8-isopentenyl naringenin from the hops is not carried out; in particular, high purity 8-prenylnaringenin is difficult to extract from hops by means of the prior art.
In view of the above, there is a need to provide a method for extracting, separating and purifying 8-prenylnaringenin from hops, so as to extract, separate and purify high-purity 8-prenylnaringenin from hops, thereby realizing industrial production.
Disclosure of Invention
The invention mainly aims to provide a method for extracting, separating and purifying 8-isopentenyl naringenin from hops, and aims to realize the extraction, separation and purification of high-purity 8-isopentenyl naringenin from hops in industrial production.
In order to achieve the purpose, the invention provides a method for extracting, separating and purifying 8-isopentenyl naringenin from hops, which comprises the following steps:
s1, performing first extraction on the hop raw material by supercritical carbon dioxide to obtain first hop raffinate.
S2, extracting the first hop raffinate by using an extracting agent to obtain an extracting solution; the extraction agent comprises water and a first solvent, the first solvent is selected from one of methanol, ethanol, acetone and ethyl acetate, and the volume mixing ratio of the water to the first solvent is 1:0.05 to 1.
S3, performing second extraction on the extracting solution through an extracting agent to obtain second extracting solution; the extractant comprises the following components in percentage by weight of 0.5: 0.1-5 volume ratio of one or two of n-butyl alcohol, isobutyl alcohol, ethyl acetate, n-hexane, cyclohexane and petroleum ether.
And S4, performing column chromatography on the second extract, and purifying to obtain the 8-isopentenyl naringenin.
Further, in the step S1, the hop material is a hop pulverized material pulverized into 20 to 120 mesh.
Further, in the step S1, the first extraction is performed at 10 to 60 ℃.
Further, the first extraction time is 2-10 hours.
Further, in the step S2, after the extracting process, the method further includes: and concentrating the volume of the mixed solution of the extracting agent and the first hop raffinate to 0.1-0.9 time of the original volume at 40-90 ℃ to obtain the extracting solution.
Further, in step S4, the column chromatography process specifically includes:
s41, loading the second extraction liquid;
s42, eluting with 0-50% ethanol water solution with first concentration to obtain first eluent.
S43, eluting the first eluent by using 50-100% ethanol water solution with second concentration to obtain second eluent.
S44, concentrating the second eluent at 40-90 ℃ until no ethanol exists.
Further, in the step S4, the first filtering process is followed by decoloring; the decoloring process specifically comprises the following steps:
and S51, carrying out vacuum drying treatment on the first filtered product to obtain a first dried product.
S52, dissolving the dried product by using 50-100% ethanol water solution with a third concentration at the temperature of 30-90 ℃, wherein the mass volume ratio of the dried product to the ethanol water solution with the third concentration is 1:5 to 20 percent to obtain decolorized dissolved solution.
S53, adding activated carbon accounting for 0.5-10% of the volume of the decolored dissolved solution into the decolored dissolved solution, decoloring at 30-90 ℃ for 0.5-4 hours, filtering, concentrating to obtain a decolored concentrated solution, cooling, crystallizing and recrystallizing to obtain the 8-isopentenyl naringenin.
Further, in step S53, the cooling and crystallizing process specifically includes: and standing the decolorized concentrated solution treated by the decolorization process at 4-10 ℃ for 2-48 hours for crystallization, and performing secondary filtration to obtain a crystallized product.
Further, in the step S53, the recrystallization process specifically includes: dissolving the crystallized product treated in the cooling crystallization process by using 50-100% of third high-concentration ethanol water at the temperature of 30-90 ℃, wherein the mass-volume ratio of the crystallized product to the third high-concentration ethanol water is 1:5 to 20, and obtaining the re-dissolving solution.
And standing the re-dissolved solution at 4-10 ℃ for 2-48 hours for crystallization, and performing third filtration to obtain the 8-isopentenyl naringenin.
Further, the second filtering step and the third filtering step further comprise vacuum drying the second filtered product and the third filtered product.
The invention has the following beneficial effects:
(1) The method comprises the steps of carrying out first extraction on a hop raw material by supercritical carbon dioxide to obtain a first hop raffinate; and then the first hop raffinate is subjected to extraction, separation and purification operations such as extraction, second extraction, column chromatography and the like one by one, so that the 8-isopentenyl naringenin is extracted, separated and purified from the hops. The 8-isopentenyl naringenin prepared by the extraction, separation and purification operation has high purity and less impurities.
(2) Pure carbon dioxide is adopted in the first extraction process for first extraction, an extracting agent in the extraction process comprises water and a first solvent, the first solvent is selected from one of methanol, ethanol, acetone and ethyl acetate, and the extracting agent in the second extraction process comprises one or two of n-butyl alcohol, isobutyl alcohol, ethyl acetate, n-hexane, cyclohexane and petroleum ether. The residual quantity of the solvents is small, and the solvent has no toxic or side effect on the environment.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the structures shown in the drawings without creative efforts.
FIG. 1 is a schematic flow chart of the method for extracting, separating and purifying 8-prenylnaringenin from hops according to the embodiment of the present invention.
The implementation, functional features and advantages of the present invention will be further described with reference to the accompanying drawings.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is apparent that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
It should be noted that the features in the following embodiments and examples may be combined with each other without conflict. It is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs and are intended to be open ended, i.e., to include any methods, devices, and materials similar or equivalent to those described in the examples.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any number between the two endpoints are optional unless otherwise specified in the invention. Test methods in which specific conditions are not noted in the following examples are generally performed under conventional conditions or conditions recommended by each manufacturer. The materials or reagents required in the following examples are commercially available unless otherwise specified.
It should be noted that the solvents involved in the present invention, such as the first solvent (methanol, ethanol, acetone, and ethyl acetate), and the solvents involved in the extraction agent (n-butanol, isobutanol, ethyl acetate, n-hexane, cyclohexane, and petroleum ether), are all commercially available as-pure reagents unless otherwise specified.
Referring to fig. 1, in order to realize the industrial production of extracting, separating and purifying high-purity 8-isopentenyl naringenin from hops, the invention provides a method for extracting, separating and purifying 8-isopentenyl naringenin from hops, which comprises the following steps:
s1, subjecting the hop raw material to first extraction by supercritical carbon dioxide to obtain a first hop raffinate.
The supercritical carbon dioxide is carbon dioxide in a state where the temperature is higher than the critical temperature Tc =31.26 ℃ and the pressure is higher than the critical pressure Pc =7.4 MPa. Specifically, the hop raw material can be subjected to a first extraction with pure carbon dioxide in a supercritical carbon dioxide unit extraction tank to obtain a first hop raffinate.
S2, extracting the first hop raffinate by using an extracting agent to obtain an extracting solution; the extractant comprises water and a first solvent, the first solvent is selected from one of methanol, ethanol, acetone and ethyl acetate, and the volume mixing ratio of the water to the first solvent is 1:0.05 to 1.
S3, performing second extraction on the extracting solution through an extracting agent to obtain second extracting solution; the extractant comprises the following components according to the weight ratio of 0.5: 0.1-5 volume ratio of one or two of n-butyl alcohol, isobutyl alcohol, ethyl acetate, n-hexane, cyclohexane and petroleum ether. Through the second extraction step, the second extraction containing the 8-isopentenyl naringenin effective component can be further extracted, and irrelevant components are discarded; it is beneficial to obtain high purity 8-isopentenylnaringenin after the rest of the steps.
And S4, carrying out column chromatography on the second extract liquor, and purifying to obtain the 8-isopentenyl naringenin.
The 8-prenylnaringenin can be obtained from hops through the steps, and the obtained 8-prenylnaringenin has high purity and less impurities.
Pure carbon dioxide is adopted in the first extraction process in the step S1 for first extraction, the extracting agent in the extraction process in the step S2 comprises water and a first solvent, the first solvent is selected from one of methanol, ethanol, acetone and ethyl acetate, and the extracting agent in the second extraction process in the step S3 comprises one or two of n-butyl alcohol, isobutyl alcohol, ethyl acetate, n-hexane, cyclohexane and petroleum ether. The residual quantity of the solvents is small, and the solvents have no toxic or side effect on the environment.
Further, in step S1, the hop material is a hop pulverized product pulverized into 20 to 120 mesh. The hop pulverized material pulverized into 20-120 meshes can be sufficiently mixed with pure carbon dioxide so as to fully perform extraction reaction in an extraction tank of a supercritical carbon dioxide device, and a first hop raffinate is obtained.
Further, in step S1, the first extraction is carried out at 10 to 60 ℃. This temperature range facilitates the extraction of hop feedstock by pure carbon dioxide.
Further, the first extraction time is 2 to 10 hours. The extraction time is less than 2 hours, and the first hop raffinate cannot be obtained to the maximum extent; too long an extraction time, in excess of 10 hours, can result in supersaturation of the first hop raffinate.
Further, in step S2, after the extracting process, the method further includes: concentrating the volume of the mixed solution of the extracting agent and the first hop raffinate to 0.1 to 0.9 time of the original volume at the temperature of between 40 and 90 ℃ to obtain the extracting solution.
Specifically, the obtained first hop raffinate is mixed with one of water and methanol, ethanol, acetone and ethyl acetate according to a mixing ratio of 1:0.05 to 1, stirring and extracting the extract for 2 to 4 times at the temperature of between 10 and 60 ℃, each time for 0.5 to 5 hours, filtering, combining the filtrates, and concentrating the filtrate under reduced pressure at the temperature of between 40 and 90 ℃ until the volume of the first hop raffinate is 0.2 to 2 times of the input volume.
Further, in step S4, the elution and impurity removal process specifically includes:
s41, loading the second extraction liquid;
s42, eluting the product of column chromatography by using 0-50% ethanol water solution with first concentration to obtain first eluent.
S43, eluting the first eluent by using 50-100% ethanol water solution with second concentration to obtain second eluent.
S44, concentrating the second eluent at 40-90 ℃ until no ethanol exists.
Specifically, the obtained extracting solution is put on a resin column, and is eluted by 0-50% ethanol water solution with first concentration, and partial impurities are removed to obtain first eluent; then eluting with 50-100% ethanol water solution with second concentration to obtain second eluent; collecting the second eluent, decompressing and concentrating at 40-90 ℃ until no ethanol exists, filtering to obtain light yellow precipitate, and drying in vacuum.
Further, in step S4, the first filtering process is followed by decolorization; the decoloring process specifically comprises the following steps:
and S51, carrying out vacuum drying treatment on the first filtered product to obtain a first dried product.
S52, dissolving the dried product in 50-100% ethanol water solution with third concentration at 30-90 ℃, wherein the mass-volume ratio of the dried product to the ethanol water solution with third concentration is 1:5 to 20 percent to obtain decolorized dissolved solution.
It should be noted that the ethanol water solution with the third concentration and the ethanol water with the second concentration used in the above step S43 may be ethanol water solutions with the same concentration.
S53, adding activated carbon accounting for 0.5-10% of the volume of the decolored dissolved solution into the decolored dissolved solution, decoloring at 30-90 ℃ for 0.5-4 hours, filtering, concentrating to obtain a decolored concentrated solution, cooling, crystallizing, and recrystallizing to obtain the 8-isopentenyl naringenin.
Specifically, the first dried product is mixed with 50-100% ethanol water solution with a third concentration according to the proportion of 1: stirring and dissolving at the temperature of 30-90 ℃ in a weight-volume ratio of 5-20, adding active carbon accounting for 0.5-10% of the volume of the decolored solution, decoloring at the temperature of 30-90 ℃ for 0.5-4 hours, passing through a precision filter, and concentrating the obtained filtrate at the temperature of 40-90 ℃ under reduced pressure until the volume of the decolored solution is 0.2-1.
Further, in step S53, the process of cooling and crystallizing specifically includes: and standing the decolorized concentrated solution after the decolorization process at 4-10 ℃ for 2-48 hours for crystallization, and performing second filtration to obtain a crystallized product.
Specifically, standing the decolorized concentrated solution at 4-10 ℃ for 2-48 hours for crystallization, carrying out secondary filtration after complete crystallization to obtain yellowish crystals, and drying in vacuum to obtain a crystallized product.
Further, in step S53, the recrystallization process specifically includes: at the temperature of 30-90 ℃, dissolving the crystallized product treated by the cooling crystallization process by using 50-100% of third high-concentration ethanol water, wherein the mass volume ratio of the crystallized product to the third high-concentration ethanol water is 1:5 to 20, and obtaining the re-dissolving solution.
Standing the re-dissolved solution at 4-10 ℃ for 2-48 hours for crystallization, and performing third filtration to obtain the 8-isopentenyl naringenin.
Specifically, at the temperature of 30-90 ℃, 50-100% of third high-concentration ethanol water is used for dissolving the crystallized product after cooling crystallization process, and the mass-volume ratio of the crystallized product to the third high-concentration ethanol water is 1:5 to 20, and obtaining the re-dissolving solution. Standing for 2-48 hours at 4-10 ℃ for crystallization, carrying out third filtration after complete crystallization, and carrying out vacuum drying to obtain white crystals.
Further, the second filtering step and the third filtering step are followed by vacuum drying of the second filtered product and the third filtered product.
Specifically, the final product after vacuum drying is crushed to obtain the finished product of 8-isopentenyl naringenin.
For a further understanding of the invention, reference will now be made to the following examples:
example 1
A method for extracting, separating and purifying 8-prenylnaringenin from flos Lupuli comprises:
1.2 kg of hop raw materials are taken, crushed to 40-60 meshes and placed in a supercritical carbon dioxide extraction kettle, a supercritical carbon dioxide extraction device is operated to extract hops for 4 hours, and 1.95kg of first hop raffinate is obtained after extraction is finished.
2. Putting 1.95kg of first hop raffinate after degreasing into an extraction tank, adding 16L of 40% methanol aqueous solution, extracting at 50 ℃ for 2 hours twice, combining extracting solutions, concentrating at 50 ℃ under reduced pressure to 0.5L, adding 2L of ethyl acetate, extracting for 1 hour, standing for 0.5 hour, separating an ethyl acetate layer, extracting a water layer for 3 times by 2L of ethyl acetate, combining ethyl acetate extracting layers, concentrating under reduced pressure to be free of ethyl acetate, adding 50mL of ethanol, completely dissolving, putting on a D101 resin column, washing with 2 times of water, 2 times of 20% ethanol water and 2 times of 40% ethanol water to remove impurities, eluting with 1 time of 90% ethanol, and collecting 90% ethanol eluent.
3. Recovering under reduced pressure to 25mL at 50 deg.C, vacuum drying to obtain 150mg pale yellow powder, measuring the content to obtain 8-isopentenyl naringenin content of 65.23%, dissolving 150mg pale yellow powder with 20mL anhydrous ethanol, adding 0.1g activated carbon, stirring, decolorizing for 1 hr, filtering with 0.45 μm filter membrane, concentrating the filtrate at 50 deg.C under reduced pressure to 10mL, standing in refrigerator at 4 deg.C for crystallizing for 24 hr, filtering, vacuum drying the obtained crystal to obtain 85mg, measuring the content to obtain 8-isopentenyl naringenin content of 89.77%, and making it yellowish. Dissolving the obtained 85mg pale yellow powder with 10mL of anhydrous ethanol, standing in a refrigerator at 4 ℃ for crystallization for 24 hours, filtering, and vacuum drying the obtained crystals to obtain 72mg, wherein the content of 8-isopentenyl naringenin is 98.70% by content measurement, and the color is white.
Example 2
A method for extracting, separating and purifying 8-isopentenyl naringenin from hops comprises the following steps:
1. taking 1kg of hop raw material, crushing the hop raw material to 40-60 meshes, putting the hop raw material into a supercritical carbon dioxide extraction kettle, operating a supercritical carbon dioxide extraction device to extract hops for 4 hours, and obtaining 0.92kg of first hop raffinate after extraction is finished.
2. Putting 0.92kg of first hop raffinate after degreasing into an extraction tank, adding 8L of 60% methanol aqueous solution, extracting at 50 ℃ for 2 hours twice, combining the extracting solutions, concentrating at 50 ℃ under reduced pressure to 0.3L, adding 1L of ethyl acetate, extracting for 1 hour, standing for 2 hours, separating an ethyl acetate layer, extracting a water layer for 1 time by 1L of ethyl acetate, combining the ethyl acetate extracting layers, concentrating under reduced pressure to be free of ethyl acetate, adding 80mL of ethanol, completely dissolving, loading onto an AB-8 resin column, washing with 0.5 time of water, 1 time of 20% ethanol water and 1 time of 60% ethanol water to remove impurities, eluting with 1 time of 80% ethanol, and collecting 80% ethanol eluent.
3. Recovering under reduced pressure to 25mL at 90 deg.C, vacuum drying to obtain 160mg pale yellow powder, measuring the content to obtain 8-isopentenyl naringenin content of 72.2%, dissolving the obtained 160mg pale yellow powder with 10mL anhydrous ethanol, adding 0.2g activated carbon, stirring, decolorizing for 1 hr, filtering with 0.45 μm filter membrane, concentrating the obtained filtrate at 50 deg.C under reduced pressure to 30mL, standing in a refrigerator at 4 deg.C for crystallizing for 24 hr, filtering, vacuum drying the obtained crystal to obtain 92mg, measuring the content to obtain 8-isopentenyl naringenin content of 91.6%, and making the color yellowish. Dissolving the obtained 92mg pale yellow powder with 30mL of anhydrous ethanol, standing in a refrigerator at 4 ℃ for crystallization for 24 hours, filtering, and vacuum drying the obtained crystals to obtain 77mg, wherein the content of 8-isopentenyl naringenin is 98.05% by content measurement, and the color is white.
Example 3
A method for extracting, separating and purifying 8-isopentenyl naringenin from hops comprises the following steps:
1. 10kg of hop raw materials are taken, crushed to 40-60 meshes and placed in a supercritical carbon dioxide extraction kettle, a supercritical carbon dioxide extraction device is operated to extract hops for 4 hours, and 9.58kg of first hop raffinate is obtained after extraction is finished.
2. Putting 9.58kg of first hop raffinate after degreasing into an extraction tank, adding 80L of 60% methanol aqueous solution, extracting at 50 ℃ for 2 hours twice, combining the extracting solutions, concentrating at 50 ℃ under reduced pressure to 3L, adding 6L of ethyl acetate, extracting for 1 hour, standing for 2 hours, separating an ethyl acetate layer, extracting a water layer for 1 time by 6L of ethyl acetate, combining the ethyl acetate extracting layers, concentrating under reduced pressure to be free of ethyl acetate, adding 640mL of ethanol, completely dissolving, putting on an AB-8 resin column, washing with water 3 times the volume of the resin column, 20% ethanol water 3 times the volume of the resin column and 60% ethanol water 2 times the volume of the resin column to remove impurities, eluting with 1 time of 95% ethanol, and collecting 95% ethanol eluent.
3. Recovering to 450mL under reduced pressure at 40 ℃, vacuum drying to obtain 1863mg of light yellow powder, measuring the content to obtain the 8-isopentenyl naringenin content of 70.08%, dissolving the obtained 1863mg of light yellow powder with 150mL of anhydrous ethanol, adding 4.5g of activated carbon, stirring and decoloring for 1 hour, filtering with a 0.45-micrometer filter membrane, concentrating the obtained filtrate to 160mL under reduced pressure at 80 ℃, standing in a refrigerator at 4 ℃ for crystallization for 24 hours, filtering, vacuum drying the obtained crystals to obtain 865mg, measuring the content to obtain the 8-isopentenyl naringenin content of 90.66%, and obtaining yellowish color. Dissolving the obtained 865mg pale yellow powder with 100mL of anhydrous ethanol, standing and crystallizing in a refrigerator at 4 ℃ for 24 hours, filtering, and vacuum drying the obtained crystals to obtain 689mg, wherein the content of 8-isopentenyl naringenin is 98.79% by content measurement, and the color is white.
Example 4
Only the first solvent and the extractant in step 2 were changed compared to example 1.
That is, 1.95kg of the first hop raffinate after degreasing is put into an extraction tank, 16L of 30% acetone aqueous solution is added, extraction is performed for 2 hours at 50 ℃, extraction is performed twice, the extract solutions are combined, reduced pressure concentration is performed at 50 ℃ to 0.5L, 2L of the first hop raffinate is added, and the weight ratio of the first hop raffinate to the second hop raffinate is calculated according to the following formula: 1, extracting the mixed solution of normal hexane and cyclohexane in a volume ratio of 1 for 1 hour, standing for 0.5 hour, separating an ethyl acetate layer, performing secondary extraction on a water layer by using 2L of ethyl acetate for 3 times, combining ethyl acetate extraction layers, concentrating under reduced pressure until no ethyl acetate exists, adding 50mL of ethanol to dissolve completely, putting the mixture on a D101 resin column, washing with 2 times of water, 2 times of 20% ethanol water and 2 times of 40% ethanol water to remove impurities, eluting with 1 time of 90% ethanol, and collecting 90% ethanol eluent.
The operation in step 3 and in example 1 was repeated further to obtain 312mg finally, wherein the content of 8-isopentenylnaringenin was 98.30% by content measurement, and the color was white.
Example 5
Compared with example 1, only the first solvent and the extractant in step 2 were changed.
Namely, 1.95kg of first hop raffinate after degreasing is put into an extraction tank, 16L of 10% ethyl acetate aqueous solution is added, the extraction is carried out for 2 hours at 50 ℃, the extraction is carried out twice, the extracting solution is combined, the pressure reduction concentration is carried out to 0.5L at 50 ℃, 2L of petroleum ether is added, the extraction is carried out for 1 hour, the standing is carried out for 0.5 hour, an ethyl acetate layer is separated, the water layer is subjected to second extraction for 3 times by using 2L of ethyl acetate, the ethyl acetate extracting layer is combined, the pressure reduction concentration is carried out until no ethyl acetate exists, 50mL of ethanol is added for complete dissolution, the mixture is put into a D101 resin column, impurities are washed by using 2 times of water, 2 times of 20% ethanol water and 2 times of 40% ethanol water, the mixture is eluted by using 1 time of 90% ethanol, and 90% ethanol eluent is collected.
The operation in step 3 of example 1 was repeated further to obtain 529mg, which was found to contain 99.20% of 8-prenylnaringenin and to have a white color.
Comparative example 1
Compared with example 1, only the first solvent and the extractant in step 2 were changed.
That is, 1.95kg of the first hop raffinate after de-greasing was placed in an extraction tank, and added to the extraction tank at a volume ratio of 1:5, extracting for 2 hours at 50 ℃, extracting twice, combining extracting solutions, concentrating to 0.5L at 50 ℃ under reduced pressure, adding 2L of ethyl acetate, extracting for 1 hour, standing for 0.5 hour, separating an ethyl acetate layer, performing second extraction on a water layer for 3 times by using 2L of ethyl acetate, combining ethyl acetate extracting layers, concentrating under reduced pressure until no ethyl acetate exists, adding 50mL of ethanol for complete dissolution, loading on a D101 resin column, washing with 2 times of water, 2 times of 20% of ethanol water and 2 times of 40% of ethanol water to remove impurities, eluting with 1 time of 90% of ethanol, and collecting 90% ethanol eluent.
By continuing to repeat the operation in step 3 of example 1, 8-prenylnaringenin could not be obtained.
Comparative example 2
Compared with example 1, only the first solvent and the extractant in step 2 were changed.
Namely, 1.95kg of the first hop raffinate after degreasing is put into an extraction tank, and added with a volume ratio of 1:1 of mixed solution XXL of normal hexane and petroleum ether, extracting for 2 hours at 50 ℃, extracting twice, combining extracting solutions, concentrating to 0.5L at 50 ℃ under reduced pressure, adding 2L of ethyl acetate, extracting for 1 hour, standing for 0.5 hour, separating an ethyl acetate layer, performing second extraction on a water layer for 3 times by using 2L of ethyl acetate, combining ethyl acetate extracting layers, concentrating to be free of ethyl acetate under reduced pressure, adding 50mL of ethanol for complete dissolution, loading on a D101 resin column, washing with 2 times of water, 2 times of 20% of ethanol water and 2 times of 40% of ethanol water to remove impurities, eluting with 1 time of 90% of ethanol, and collecting 90% ethanol eluent.
The procedure of step 3, in example 1 was repeated, and 8-prenylnaringenin could not be obtained.
Therefore, the invention realizes the extraction, separation and purification of the high-purity 8-isopentenyl naringenin from the hop, and the 8-isopentenyl naringenin obtained by the extraction, separation and purification operation has high purity and less impurities; and the residual quantity of the solvent adopted in the extraction, separation and purification operation process is less, and the method has no toxic or side effect on the environment.
In summary, in the above technical solutions of the present invention, the above are only preferred embodiments of the present invention, and the technical scope of the present invention is not limited thereby, and all equivalent structural changes made by using the contents of the specification and the drawings of the present invention or other related technical fields directly/indirectly applied thereto are included in the scope of the present invention.
Claims (10)
1. A method for extracting, separating and purifying 8-isopentenyl naringenin from hops is characterized by comprising the following steps:
s1, performing first extraction on a hop raw material by supercritical carbon dioxide to obtain first hop raffinate;
s2, extracting the first hop raffinate through an extracting agent to obtain an extracting solution; the extractant comprises water and a first solvent, the first solvent is selected from one of methanol, ethanol, acetone and ethyl acetate, and the volume mixing ratio of the water to the first solvent is 1:0.05 to 1;
s3, performing second extraction on the extracting solution through an extracting agent to obtain second extracting solution; the extractant comprises the following components according to a ratio of 0.5: 0.1-5 volume ratio of one or two of n-butyl alcohol, isobutyl alcohol, ethyl acetate, n-hexane, cyclohexane and petroleum ether;
and S4, performing column chromatography on the second extract, and purifying to obtain the 8-isopentenyl naringenin.
2. The method for extracting, separating and purifying 8-prenylnaringenin from hops according to claim 1, wherein the hop material is a pulverized hop material pulverized into 20 to 120 mesh in the step S1.
3. The method for extracting, separating and purifying 8-prenylnaringenin from hop as claimed in claim 1, wherein in step S1, the first extraction is carried out at 10-60 ℃.
4. The method for extracting, separating and purifying 8-isopentenyl naringenin from hop according to claim 1, wherein the time period of the first extraction is 2-10 hours.
5. The method for extracting, separating and purifying 8-prenylnaringenin from hop according to claim 1, wherein in step S2, the extraction process is followed by: and concentrating the volume of the mixed solution of the extracting agent and the first hop raffinate to 0.1-0.9 time of the original volume at 40-90 ℃ to obtain the extracting solution.
6. The method for extracting, separating and purifying 8-isopentenylnaringenin from hops as claimed in claim 1, wherein in the step S4, the column chromatography specifically comprises:
s41, loading the second extraction liquid;
s42, eluting with 0-50% ethanol water solution with a first concentration to obtain a first eluent;
s43, eluting the first eluent by using 50-100% ethanol water solution with second concentration to obtain second eluent;
s44, concentrating the second eluent at 40-90 ℃ until no ethanol exists.
7. The method for extracting, separating and purifying 8-isopentenylnaringenin from hop as claimed in claim 1, wherein in the step S4, the first filtering process is followed by decolorization; the decoloring process specifically comprises the following steps:
s51, carrying out vacuum drying treatment on the first filtered product to obtain a first dried product;
s52, dissolving the dried product with 50-100% ethanol water solution with a third concentration at 30-90 ℃, wherein the mass-volume ratio of the dried product to the ethanol water solution with the third concentration is 1:5 to 20 percent to obtain decolorized dissolved solution;
s53, adding activated carbon accounting for 0.5-10% of the volume of the decolored dissolved solution into the decolored dissolved solution, decoloring at 30-90 ℃ for 0.5-4 hours, filtering, concentrating to obtain a decolored concentrated solution, cooling, crystallizing and recrystallizing to obtain the 8-isopentenyl naringenin.
8. The method for extracting, separating and purifying 8-isopentenylnaringenin from hops as claimed in claim 7, wherein in the step S53, the cooling and crystallization process specifically comprises: and standing the decolorized concentrated solution treated by the decolorization process at 4-10 ℃ for 2-48 hours for crystallization, and performing secondary filtration to obtain a crystallized product.
9. The method for extracting, separating and purifying 8-prenylnaringenin from hop according to claim 7, wherein in step S53, the recrystallization process comprises: dissolving the crystallized product treated in the cooling crystallization process by using 50-100% of third high-concentration ethanol water at the temperature of 30-90 ℃, wherein the mass-volume ratio of the crystallized product to the third high-concentration ethanol water is 1: 5-20 to obtain a re-dissolved solution;
and standing the re-dissolved solution at 4-10 ℃ for 2-48 hours for crystallization, and performing third filtration to obtain the 8-isopentenyl naringenin.
10. The method for extracting, separating and purifying 8-isopentenylnaringenin from hop according to claim 8-9, wherein the second filtration and the third filtration are further followed by vacuum drying of the second filtration and the third filtration.
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| PCT/CN2022/131559 WO2024087261A1 (en) | 2022-10-25 | 2022-11-11 | Method for extracting, separating, and purifying 8-prenylnaringenin from hops |
| BE20225985A BE1030422B1 (en) | 2022-10-25 | 2022-12-02 | METHOD FOR EXTRACTION AND PURIFICATION OF 8-PRENYLNARINGENIN FROM HOPS |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005092353A1 (en) * | 2004-03-16 | 2005-10-06 | Dr. Willmar Schwabe Gmbh & Co. Kg | Hop extracts, production and use thereof |
| JP2005343864A (en) * | 2004-06-07 | 2005-12-15 | Kuraray Co Ltd | Skin care preparation for external use |
| CN1893963A (en) * | 2003-12-16 | 2007-01-10 | 生物动力公司 | Production of hop extracts having oestrogenic and antiproliferative bioactivity |
| ITMI20060244A1 (en) * | 2006-02-10 | 2007-08-11 | Hammer Pharma S P A | ENRICHING AND EXTRACTION PROCESS OF SPECIFIC HIP POLYPHENOLS |
| CN101138418A (en) * | 2007-10-16 | 2008-03-12 | 浙江大学 | Hop supercritical residues comprehensive utilization method |
| CN101768068A (en) * | 2010-01-06 | 2010-07-07 | 刘玉英 | Method utilizing hop residues to extract xanthohumol |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19939350B4 (en) * | 1999-08-19 | 2005-04-07 | Plantextrakt Gmbh & Co. Kg | Hop extract and process for its preparation |
| DE10139479A1 (en) * | 2001-08-10 | 2003-02-27 | Schwabe Willmar Gmbh & Co | Hop extracts, process for their preparation and use |
| CA2544488A1 (en) * | 2006-05-01 | 2007-11-01 | Chemisch Biochemisch Onderzoekscn | Use of hop polyphenols in beer |
| CN107337661A (en) * | 2016-11-30 | 2017-11-10 | 南昌大学 | A kind of method that the tri hydroxy flavanone of 8 prenyl 4,5,7 is extracted from hops |
| JP7122106B2 (en) * | 2017-12-05 | 2022-08-19 | 株式会社ユーグレナ | Antiviral food composition and antiviral agent |
| WO2020012681A1 (en) * | 2018-07-09 | 2020-01-16 | 株式会社ダイセル | Method for producing 8-prenylnaringenin |
-
2022
- 2022-10-25 CN CN202211313437.1A patent/CN115650942B/en active Active
- 2022-11-11 WO PCT/CN2022/131559 patent/WO2024087261A1/en unknown
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Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1893963A (en) * | 2003-12-16 | 2007-01-10 | 生物动力公司 | Production of hop extracts having oestrogenic and antiproliferative bioactivity |
| US20070110835A1 (en) * | 2003-12-16 | 2007-05-17 | Francis Maes | Method for the production of enriched hop extracts having combined oestrogenic and antiproliferative bioactivity |
| WO2005092353A1 (en) * | 2004-03-16 | 2005-10-06 | Dr. Willmar Schwabe Gmbh & Co. Kg | Hop extracts, production and use thereof |
| JP2005343864A (en) * | 2004-06-07 | 2005-12-15 | Kuraray Co Ltd | Skin care preparation for external use |
| ITMI20060244A1 (en) * | 2006-02-10 | 2007-08-11 | Hammer Pharma S P A | ENRICHING AND EXTRACTION PROCESS OF SPECIFIC HIP POLYPHENOLS |
| CN101138418A (en) * | 2007-10-16 | 2008-03-12 | 浙江大学 | Hop supercritical residues comprehensive utilization method |
| CN101768068A (en) * | 2010-01-06 | 2010-07-07 | 刘玉英 | Method utilizing hop residues to extract xanthohumol |
Non-Patent Citations (3)
| Title |
|---|
| JANG HOON KIM等: ""Kushenol A and 8-prenylkaempferol, tyrosinase inhibitors, derived from Sophora flavescens"", JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, vol. 33, no. 1, pages 1048 - 1054 * |
| M. BIENDL等: ""Isolation of Prenylflavonoids from Hops"", IIIRD INT’L HUMULUS SYMP., pages 131 - 140 * |
| 崔熠可;赖玉清;黄惠明;陈静华;周跃平;闫冀;吴磊;: "啤酒花中8-异戊烯基柚皮素提取及含量测定方法的优化及验证", 中国生物制品学杂志, no. 08, pages 850 - 854 * |
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| WO2024087261A1 (en) | 2024-05-02 |
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