CN112409151B - Industrial method for extracting resin acid and xanthohumol from hops - Google Patents
Industrial method for extracting resin acid and xanthohumol from hops Download PDFInfo
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- G01N30/02—Column chromatography
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- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G01N2030/062—Preparation extracting sample from raw material
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Abstract
The invention relates to an industrialized method for extracting effective components from hops, which belongs to the technical field of extraction of plant functional components and comprises the following steps: 1) extracting the hops by using a ketone or alcohol solvent of C1-C8 as an extracting agent to obtain an extracting solution; 2) adding a diluting solvent into the extracting solution obtained in the step 1), adjusting the pH value to 2-6, adding a C4-C8 hydrocarbon solvent for extraction, standing for layering, and concentrating the upper solution to obtain resin acid; 3) concentrating the lower layer sample liquid in the step 2), adding a polar solvent, separating out solids, filtering and drying to obtain the xanthohumol. The extractant selected by the invention has very high selectivity on the resin acid and the xanthohumol, can be used for fully and specifically extracting, can be used for obtaining the resin acid and the xanthohumol through simple subsequent separation, has simple process and low production cost, and is beneficial to industrial production.
Description
Technical Field
The invention relates to the technical field of plant functional component extraction, in particular to an industrialized method for extracting resin acid and xanthohumol from hops.
Background
The hops has the effects of invigorating stomach, promoting digestion, promoting urination, calming the nerves, relieving cough and reducing sputum, can be used for treating inappetence, abdominal distension, pulmonary tuberculosis, pleuritis, insomnia, hysteria, edema, cystitis and the like, is recorded in various classics as a national medicine (traditional Chinese medicine) in China, and is a Xinjiang characteristic resource plant with both medicine and food. The chemical components of hops mainly include resin acids, polyphenol compounds, volatile flavor components and the like. Hop resin acids are mainly two types, alpha-acids and beta-acids, and the isomerization product of alpha-acids iso-alpha-acids are the main source of bitterness. The alpha-acids are mainly composed of 5 homologs of humulone, cohumulone, adhumulone, etc., while the beta-acids are composed of 5 homologs of lupulone, cohumulone, adhumulone, post-lupulone, and pre-lupulone. Besides resin acids, the hop contains abundant xanthohumol, demethyl xanthohumol, lutequinine and other components, wherein the xanthohumol is a unique component of the hop and accounts for 0.1-1% of the dry weight of the hop.
At present, the research at home and abroad mainly focuses on the research on the extraction and isomerization of the resin acid in the hop, and the extraction mode usually utilizes supercritical CO 2 The technology is used for extraction. However, research on xanthohumol mostly focuses on extraction, separation and purification, and the hop meal after resin acid extraction is extracted by using an alcohol solution and then extracted by means of chromatographic separation, crystallization and the like, so that the extraction is insufficient, and in order to obtain high-purity xanthohumol, a plurality of separation and purification steps are used.
Disclosure of Invention
Aiming at the problems, the invention discloses an industrial method for extracting resin acid and xanthohumol from hops, which has high extraction efficiency and simple purification method and is beneficial to industrial mass production.
In order to achieve the purpose, the invention adopts the technical scheme that:
a method for extracting resin acids and xanthohumol from hops comprises the following steps:
1) extracting the hop by using a ketone or alcohol solvent of C1-C8 as an extracting agent to obtain an extracting solution;
2) adding a diluting solvent into the extracting solution obtained in the step 1), adjusting the pH value to 2-6, adding a C4-C8 hydrocarbon solvent for extraction, standing for layering, and concentrating the upper solution to obtain resin acid;
3) concentrating the lower layer sample liquid in the step 2), adding a polar solvent, separating out solids, filtering and drying to obtain the xanthohumol.
The technical scheme of the invention is further improved as follows: the ketone and alcohol solvents of C1-C8 in the step 1) comprise one or the combination of more than two of acetone, butanone, methanol, ethanol and propanol.
The technical scheme of the invention is further improved as follows: the volume fraction of the ketone and alcohol solvents in the step 1) is more than 80 percent.
The technical scheme of the invention is further improved as follows: the mass-to-volume ratio of hops to the extraction solvent in step 1) (kg: l) is less than 1: 3-7; the extraction temperature is between 25 and 60 ℃; the extraction time is 2-6 h; the extraction times are 1-4 times.
The technical scheme of the invention is further improved as follows: the diluting solvent in the step 2) comprises one or the combination of more than two of water, chloroform, 10-80% alcohol solution and 10-80% ketone solution.
The technical scheme of the invention is further improved as follows: the polar solvent in the step 3) comprises one or the combination of more than two of water, 1-30% of alcohol solution and 1-30% of ketone solution.
The technical scheme of the invention is further improved as follows: the concentration of the extractant after the dilution solvent is added in the step 2) is less than 80 percent.
The technical scheme of the invention is further improved as follows: the concentration range of the extracting agent is between 10 and 40 percent after the polar solvent is added in the step 3).
The technical scheme of the invention is further improved as follows: the hydrocarbon solvent of C4-C8 in the step 2) comprises vegetable oil, petroleum ether and n-hexane.
Due to the adoption of the technical scheme, the invention has the following beneficial effects:
1) the invention provides a method for simultaneously extracting resin acid and xanthohumol, the operation procedures are simple and comprise the operations of extraction, concentration and extraction, compared with the scheme of separately extracting picrorhiza supercritical extraction in the prior art, the extraction solvent is easy to separate and recycle, the next step of production and application is easy to carry out, the drying and concentration cost in the extraction process is low, and the method is suitable for industrial large-scale production.
2) The content of the two products can be ensured by controlling the concentration of the extraction solvent and the type and proportion of the extraction solvent.
3) By adopting the method, the resin acid and the xanthohumol in the hop can be fully extracted, the yield of the obtained resin acid is 90 percent, and the content is more than 65 percent; the yield of the xanthohumol is more than 90 percent, and the purity is more than 65 percent.
Drawings
FIG. 1 is a liquid chromatogram of xanthohumol extracted according to the example of the present invention.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The resin acid is detected according to the national standard method GB/T20369-2006.
The method for detecting the xanthohumol comprises the following steps:
1. sample pretreatment:
(1) preparation of extract sample solution in production process
Weighing 0.3-0.5 g (accurate to 0.0001g) of extract sample in a 50mL volumetric flask, paralleling the sample, ultrasonically dissolving the sample in methanol, fixing the volume, and shaking up. The sample is filtered through a 0.45 mu m filter membrane to be detected.
(2) Preparation of raw Material samples
Dividing the measured hop raw material by quartering method, pulverizing for 3 times with universal pulverizer, each time pulverizing time can not exceed 10s, placing into mixing bag, and shaking for 2-3 min. Accurately weighing 1.0g (accurate to 0.0001g) ± 0.1g of sample, placing the sample in a 100mL volumetric flask, diluting to constant volume with methanol, performing water bath ultrasound for 30min, shaking up, and filtering the sample solution with a 0.45 μm filter membrane to be detected.
2. High performance liquid reference chromatography conditions
And (3) chromatographic column: caprisil C18-AQ column (250X 4.6mm, 5 μm)
Temperature of the column: at 40 ℃. Sample injection amount: 10 ul. Operating time: and 20 min. Flow rate: 1.0 mL/min.
Detection wavelength: 358 nm.
Example 1:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 70L of 98% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. Adding 180L of water into the extractive solution, and adjusting the concentration of acetone to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 460L vegetable oil extraction solvent, stirring uniformly, standing and layering. After the upper layer liquid is separated, the upper layer liquid is concentrated until the residual solvent is below 800ppm, and 1.112kg of resin acid product with 68.61 percent of content and 98.06 percent of yield of resin acid content is obtained. The lower solution was concentrated and water was added to bring the acetone concentration to 10%, at which point the solids content was 10%. Filtering, drying the filter cake to obtain 55.0g of xanthohumol product, wherein the content of the xanthohumol product is 71.29%, and the yield of the xanthohumol content is 98.02%.
Example 2:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 98% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. Adding 10% acetone 90L into the extractive solution, and adjusting the concentration of acetone to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 200L vegetable oil extraction solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of below 800ppm, and 1.109kg of resin acid product with the content of 68.72 percent and the yield of the resin acid content of 97.96 percent is obtained. The lower solution was concentrated and water was added to a concentration of 25% acetone, at which point the solids content was 10%. Filtering, drying the filter cake to obtain 53.8g of xanthohumol product, wherein the content of the xanthohumol product is 71.01%, and the yield of the xanthohumol content is 95.51%.
Example 3:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 98% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. 76L of water was added to the extract and the concentration of the extractant acetone was adjusted down to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 200L vegetable oil extraction solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated until the residual solvent is below 800ppm, and 1.104kg of resin acid product with 68.67 percent of content and 97.44 percent of yield of resin acid content is obtained. The lower solution was concentrated and water was added to a concentration of 40% acetone, at which point the solids content was 15%. Filtering, drying the filter cake to obtain 52.6g of xanthohumol product, wherein the content of the xanthohumol product is 69.95%, and the yield of the xanthohumol content is 91.98%.
Example 4:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 98% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. 76L of water was added to the extract and the concentration of the extractant was adjusted down to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 200L vegetable oil extraction solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of below 800ppm, and 1.101kg of resin acid product is obtained, the content of the resin acid product is 68.71 percent, and the yield of the resin acid content is 97.24 percent. The lower solution was concentrated and water was added to bring the acetone concentration to 10% at which point the solids content was 30%. Filtering, drying the filter cake to obtain 57.2g of xanthohumol product, wherein the content of the xanthohumol product is 66.94%, and the yield of the xanthohumol content is 95.72%.
Example 5:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 98% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. 27L of water was added to the extract and the concentration of the extractant acetone was adjusted down to 80%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 150L vegetable oil extraction solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of below 800ppm, and 1.099kg of resin acid product is obtained, the content of the resin acid product is 66.52%, and the yield of the resin acid content is 93.97%. The lower solution was concentrated and water was added to bring the acetone concentration to 10% at which point the solids content was 10%. Filtering, drying the filter cake to obtain 59.3g of xanthohumol product, wherein the content of the xanthohumol product is 65.14%, and the yield of the xanthohumol content is 96.57%.
Example 6:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 80% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. 40L of water was added to the extract and the concentration of the extractant acetone was adjusted down to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 160L petroleum ether solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of below 800ppm, and 1.121kg of resin acid product is obtained, the content of the resin acid product is 66.75 percent, and the yield of the resin acid content is 96.18 percent. The lower solution was concentrated and water was added to a concentration of 25% acetone, at which point the solids content was 10%. Filtering, and drying the filter cake to obtain 58.2g of xanthohumol product, wherein the content of the xanthohumol product is 66.35%, and the yield of the xanthohumol content is 96.54%.
Example 7:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 100% methanol solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. Adding 80L water into the extractive solution, and adjusting the concentration of methanol as extractant to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 200L petroleum ether solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated until the residual solvent is below 800ppm, and 1.033kg of resin acid product is obtained, wherein the content of the resin acid product is 68.12 percent, and the yield of the resin acid content is 90.45 percent. The lower solution was concentrated and water was added to a concentration of 25% methanol, at which point the solids content was 10%. Filtering, and drying the filter cake to obtain 54.6g of xanthohumol product, wherein the content of the xanthohumol product is 68.09%, and the yield of the xanthohumol content is 90.14%.
Example 8:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 100% methanol solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. 95L of water was added to the extract and the concentration of the extractant methanol was adjusted down to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 200L n-hexane solvent, continuously stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of below 800ppm, and 1.029kg of resin acid product is obtained, the content of the resin acid product is 68.07%, and the yield of the resin acid content is 90.03%. The lower solution was concentrated and water was added to a 25% acetone concentration, at which point the solids content was 15%. Filtering, drying the filter cake to obtain 55.1g of xanthohumol product, wherein the content of the xanthohumol product is 67.83%, and the yield of the xanthohumol content is 93.44%.
Example 9:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 80% methanol solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. Adding 40L of water into the extractive solution, and adjusting the concentration of the extractant to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 160L n-hexane solvent, continuously stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of below 800ppm, and 1.03kg of resin acid product with 67.98% of content and 90.0% of resin acid content yield is obtained. The lower solution was concentrated and water was added to a concentration of 25% acetone, at which point the solids content was 10%. Filtering, and drying the filter cake to obtain 53.7g of xanthohumol product, wherein the content of the xanthohumol product is 67.14%, and the yield of the xanthohumol content is 90.14%.
Comparative example 1:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 20L of 98% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. Adding 50L water into the extractive solution, and adjusting the concentration of acetone to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 130L vegetable oil extraction solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of less than 800ppm, and 0.75kg of resin acid product with 68.61% of content and 66.14% of yield is obtained. The lower solution was concentrated and water was added to bring the acetone concentration to 10% at which point the solids content was 10%. Filtering, drying the filter cake to obtain 46.5g of xanthohumol product, wherein the content of the xanthohumol product is 71.29%, and the yield of the xanthohumol content is 82.87%.
Comparative example 2:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 70% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. Adding 20L of water into the extractive solution, and adjusting the concentration of acetone to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 35L vegetable oil extraction solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of less than 800ppm, and 0.771kg of resin acid product is obtained, the content of the resin acid product is 60.49 percent, and the yield of the resin acid content is 59.95 percent. The lower solution was concentrated and water was added to bring the acetone concentration to 10% at which point the solids content was 10%. And filtering, and drying a filter cake to obtain 56.3g of a xanthohumol product, wherein the content of the xanthohumol product is 54.32%, and the yield of the xanthohumol content is 76.46%.
Comparative example 3:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 98% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. 11L of water was added to the extract and the concentration of the extractant acetone was adjusted down to 90%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 33L vegetable oil extraction solvent, stirring uniformly, standing for layering. After the upper layer liquid is separated, the upper layer liquid is concentrated to the solvent residue of below 800ppm, and 1.64kg of resin acid product is obtained, the content of the resin acid product is 45.74 percent, and the yield of the resin acid content is 96.42 percent. The lower solution was concentrated and water was added to a concentration of 50% acetone, at which point the solids content was 10%. Filtering, and drying the filter cake to obtain 30.1g of xanthohumol product, wherein the content of the xanthohumol product is 48.96%, and the yield of the xanthohumol content is 36.84%.
Comparative example 4:
taking 10kg of hop raw material, the resin acid content and the xanthohumol content are respectively 7.78% and 0.4%, adding 30L of 98% acetone solvent, extracting at 60 deg.C for 6h, and extracting for 4 times. Mixing the extractive solutions. 76L of water was added to the extract and the concentration of the extractant acetone was adjusted down to 60%. Dropwise adding 0.5mol/L hydrochloric acid until the pH value is 4, stirring uniformly, adding 50L vegetable oil extraction solvent, stirring uniformly, standing for layering. After the separation of the upper layer liquid, the upper layer liquid is concentrated to the residual solvent of below 800ppm, and 1.102kg of resin acid product is obtained, the content of which is 68.49 percent, and the yield of the resin acid content is 97.01 percent. After the lower solution was concentrated, water was added to a concentration of 10% acetone and a solid content of 40%. Filtering, and drying the filter cake to obtain 62.1g of xanthohumol product, wherein the content of the xanthohumol product is 58.04%, and the yield of the xanthohumol content is 90.11%.
TABLE 1 comparison of resin acid and xanthohumol content and yield for each example and comparative example
From the above examples and comparative examples, it can be seen that the method of the present application simultaneously obtains xanthohumol and resin acids, and the obtained xanthohumol and resin acids have higher content and higher yield.
The industrial method for extracting the resin acid and the xanthohumol from the hops has high extraction efficiency and simple purification method, and is beneficial to industrial mass production.
Claims (1)
1. A method for extracting resin acids and xanthohumol from hops is characterized in that: the method comprises the following steps:
1) extracting flos Lupuli with acetone or methanol as extractant to obtain extractive solution;
2) adding a diluting solvent into the extracting solution obtained in the step 1), adjusting the pH value to 2-6, adding vegetable oil, petroleum ether or n-hexane for extraction, standing for layering, and concentrating the upper-layer solution to obtain resin acid;
3) concentrating the lower layer sample liquid in the step 2), adding a polar solvent, separating out solids, filtering and drying to obtain xanthohumol;
the volume fraction of acetone or methanol in the step 1) is more than 80 percent; the mass-to-volume ratio kg of the hop to the extraction solvent in the step 1): l is less than 1: 3-7; the extraction temperature is 60 ℃; the extraction time is 2-6 h; extracting for 1-4 times; the diluting solvent in the step 2) is water; after the diluent solvent is added in the step 2), the concentration of the extractant is less than 80 percent; the polar solvent in the step 3) is water; the concentration range of the extracting agent after the polar solvent is added in the step 3) is 10-40%.
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Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1274678A (en) * | 1968-11-19 | 1972-05-17 | Bush Boake Allen Ltd | Hop extracts |
| GB1310019A (en) * | 1970-03-03 | 1973-03-14 | White Tomkins Ltd | Purification of hop extracts |
| SI1230337T1 (en) * | 1999-11-18 | 2007-04-30 | Steiner Inc S S | Process for the hydrogenation of hop resin acids |
| CN101376625A (en) * | 2008-10-07 | 2009-03-04 | 浙江大学 | Method for separating alpha and beta acid from hop extract |
| CN110746284A (en) * | 2019-11-18 | 2020-02-04 | 新疆大学 | Extraction and separation method of β -acid homolog in hops |
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