CN115197287A - Method for comprehensively extracting rubusoside, quercetin and ellagic acid from sweet tea and application thereof - Google Patents
Method for comprehensively extracting rubusoside, quercetin and ellagic acid from sweet tea and application thereof Download PDFInfo
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- CN115197287A CN115197287A CN202210716190.1A CN202210716190A CN115197287A CN 115197287 A CN115197287 A CN 115197287A CN 202210716190 A CN202210716190 A CN 202210716190A CN 115197287 A CN115197287 A CN 115197287A
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- quercetin
- rubusoside
- water
- ellagic acid
- sweet tea
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- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 title claims abstract description 106
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 title claims abstract description 52
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 title claims abstract description 52
- YWPVROCHNBYFTP-UHFFFAOYSA-N Rubusoside Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC1OC(CO)C(O)C(O)C1O YWPVROCHNBYFTP-UHFFFAOYSA-N 0.000 title claims abstract description 52
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229960001285 quercetin Drugs 0.000 title claims abstract description 52
- 235000005875 quercetin Nutrition 0.000 title claims abstract description 52
- YWPVROCHNBYFTP-OSHKXICASA-N rubusoside Chemical compound O([C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YWPVROCHNBYFTP-OSHKXICASA-N 0.000 title claims abstract description 52
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 title claims abstract description 51
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- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 title claims abstract description 51
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 238000010828 elution Methods 0.000 claims description 17
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- 108010009736 Protein Hydrolysates Proteins 0.000 claims description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 5
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- JMGCAHRKIVCLFW-UHFFFAOYSA-N 1-O-Galloylcastalagin Natural products Oc1cc(cc(O)c1O)C(=O)OC2C3OC(=O)c4c2c(O)c(O)c(O)c4c5c(O)c(O)c(O)c6c5C(=O)OC3C7OC(=O)c8cc(O)c(O)c(O)c8c9c(O)c(O)c(O)cc9C(=O)OCC7OC(=O)c%10cc(O)c(O)c(O)c6%10 JMGCAHRKIVCLFW-UHFFFAOYSA-N 0.000 description 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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Abstract
The invention discloses a method for comprehensively extracting rubusoside, quercetin and ellagic acid from rubus suavissimus, which at least comprises five steps of polyamide separation, rubusoside purification, acidolysis, quercetin purification and ellagic acid purification. According to the invention, plant polyphenol is efficiently separated by using polyamide, and meanwhile, the sweet tea is comprehensively extracted by using the solubility difference of quercetin and ellagic acid, so that high-purity rubusoside, quercetin and ellagic acid are obtained, the comprehensive utilization value of the sweet tea is improved, and the economic benefit is greatly enhanced; the purity of the rubusoside, the quercetin and the ellagic acid prepared by the method is higher than 95%, the recovery rate is higher than 90%, and the product has good color and luster; the method provided by the invention has the advantages of strong operability of the process, low cost, no pollution and suitability for industrial production, not only realizes the comprehensive utilization of sweet tea resources, but also solves the problem of environmental pollution caused by the sweet tea waste residue after the sweet tea glycoside is extracted by water.
Description
Technical Field
The invention relates to the technical field of extraction of plant effective components, and particularly relates to a method for comprehensively extracting rubusoside, quercetin and ellagic acid from rubus suavissimus and application thereof.
Background
The sweet tea contains abundant bioactive components including rubusoside, quercetin, ellagic acid, etc.
Ellagic acid is a natural polyphenol with molecular formula of C 14 H 6 O 8 In nature, it is mostly present in condensed form, while free ellagic acid is usually present in the structure of trans-gallic acid tannin and is less distributed in nature. Ellagic acid has various bioactive functions, such as antioxidant function, anticancer, antimutagenic, and inhibiting proliferation of HIV; ellagic acid is also a coagulant, has good inhibitory effect on various bacteria and viruses, and can prevent infection and inhibit ulcer. In addition, ellagic acid also has various physiological effects of lowering blood pressure, tranquilizing, and preventing osteoporosis.
Quercetin, which is mainly present in vegetables, fruits, tea, wine, etc. in the form of glycoside, is a dietary polyphenol that can benefit from its protective effects through diet or as a food supplement, and is widely available, safe and readily available as compared to chemical preparations. The anti-diabetes, anti-hypertension, anti-Alzheimer disease, anti-arthritis, anti-influenza virus, anti-microbial infection, anti-aging, autophagy influencing and cardiovascular protection effects of quercetin have been widely studied, and recently, the research on the anti-cancer activity of quercetin on different cancer cell lines has also been reported.
In the industrial production of rubusoside, as only high-purity rubusoside needs to be obtained, in the whole production process, various active ingredients including ellagitannin, quercetin and glycoside thereof are taken as waste liquid and waste residue to be discharged, so that not only is serious waste caused to the biological resources of rubusoside, but also higher economic value cannot be created, the treatment difficulty of three industrial wastes is increased, the pollution to water sources and soil is caused, and the sustainable development of the industry is not facilitated.
So far, no report related to a simple, environment-friendly, stable-process and industrial large-scale production method capable of comprehensively extracting rubusoside, quercetin and ellagic acid in the rubus suavissimus is found.
In view of this, the invention is particularly proposed.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a method for comprehensively extracting rubusoside, quercetin and ellagic acid in rubus suavissimus and application thereof.
In order to realize the purpose, the technical scheme of the invention is as follows:
a method for comprehensively extracting rubusoside, quercetin and ellagic acid from rubus suavissimus comprises the following steps:
s1, separation of Polyamide
Loading the supernatant obtained after sweet tea extraction on a polyamide column, collecting effluent liquid on the column, washing with water after sample loading to obtain water washing liquid, and eluting with alkali water after water washing to obtain alkali washing liquid;
s2, rubusoside purification
Mixing effluent liquid and water washing liquid in the step S1, loading the effluent liquid and the water washing liquid into a macroporous adsorption resin column, washing with water after sample loading is finished, eluting with ethanol water after the washing with water is finished, concentrating the obtained ethanol eluent to dryness, and carrying out purification treatment to obtain rubusoside;
s3, acid hydrolysis
Adding hydrochloric acid into the alkaline washing liquid in the S1 to adjust the pH value to be weakly acidic, adding acid for acidification after concentration, heating for hydrolysis, carrying out solid-liquid separation on the obtained hydrolysate, and cleaning the obtained first filter residue with deionized water until the water washing liquid is neutral to obtain the sweet tea polyphenol hydrolysate;
s4, purifying quercetin
Adding a 95v% ethanol aqueous solution into the sweet tea polyphenol hydrolysate in the step S3, heating, stirring and filtering while the mixture is hot to obtain a second filtrate and a second filter residue, concentrating the second filtrate, standing at a low temperature for crystallization, and sequentially performing suction filtration, water washing and drying to obtain quercetin;
s5, ellagic acid purification
And (3) dissolving the second filter residue in the S4 with alkali water, removing insoluble substances to obtain a second supernatant, adding acid into the second supernatant for acid precipitation, standing, filtering, and washing with deionized water until the second supernatant is neutral to obtain ellagic acid.
In the technical scheme, in the step S1, the flow rate of the supernatant liquid on the upper column is 0.5-1.5BV/h.
In the technical scheme, in the step S1, the elution volume and the elution flow rate of the water washing are respectively 1-2BV and 2-4BV/h.
In the above technical solution, in step S1, the alkaline water is a 1-5wt% NaOH aqueous solution.
In the technical scheme, in the step S1, the elution volume and the elution flow rate of the alkaline water are respectively 2-5BV and 2-4BV/h.
In the above technical solution, in step S3, the amount of the hydrochloric acid added is controlled to be pH 5.5-6.5.
In the above technical solution, in step S3, the multiple of the concentration is 5 to 10 times.
In the above technical scheme, in the step S3, the temperature and time of the heating hydrolysis are 100-120 ℃ and 1-5h, respectively.
Further, in the above technical solution, in step S4, the amount of the 95v% ethanol aqueous solution added is 5 to 50mL for 1g of sweet tea polyphenol hydrolysate.
Further, in the above technical solution, in the step S4, the heating temperature is 50 to 60 ℃.
Further, in the above technical solution, in step S5, the alkaline water is a 1-5wt% NaOH aqueous solution.
Further, in the above technical scheme, in step S5, the addition mass of the alkaline water is 10-100 times of that of the second filter residue.
Further, in the above technical scheme, in the step S5, the acid precipitation is specifically performed by adding acid to adjust the pH to 2-4, and standing for 5-20 hours.
Still further, in the above technical solution, in the step S2, the flow rate of the macroporous adsorbent resin on the column is 0.5-1.5BV/h.
Still further, in the above technical solution, in the step S2, the elution volume and the elution flow rate of the water washing are 4-6BV and 2-4BV/h, respectively.
Still further, in the above technical solution, in the step S2, the concentration, the elution volume, and the elution flow rate of the ethanol aqueous solution are 55-75v%, 2-5BV, and 2-4BV/h, respectively.
Further, in the above technical scheme, in the step S2, the purification treatment includes adding a certain proportion of solvent, heating for redissolution, crystallizing, filtering, and drying.
In a preferred embodiment of the present invention, the solvent is deionized water or an aqueous ethanol solution, and the crystallization temperature and time are 2-10 ℃ and 12-48h, respectively.
In a specific embodiment of the present invention, the method for comprehensively extracting rubusoside, quercetin and ellagic acid from rubus suavissimus further comprises:
s0, drying, extracting and concentrating
Cleaning and drying sweet tea to constant weight, pulverizing, sieving with 20-50 mesh sieve, adding 40-70v% ethanol water solution, heating and reflux extracting for several times, mixing extractive solutions, concentrating, recovering ethanol until no ethanol smell exists, centrifuging to remove insoluble substances, and collecting supernatant.
Specifically, in the above technical solution, in the step S0, the drying temperature is 40 to 60 ℃.
Specifically, in the above technical solution, in the step S0, the temperature of the heating reflux is 70 to 100 ℃.
Specifically, in the above technical solution, in step S0, in the heating reflux process, the material-to-liquid ratio is controlled to be 1g:5-30mL.
Specifically, in the above technical solution, in the step S0, the number of times of the heating reflux is 2 to 3 times.
Specifically, in the above technical solution, in the step S0, the heating reflux time is 30-90min.
The invention also provides application of the method in comprehensive extraction of rubusoside, quercetin and ellagic acid in rubus suavissimus.
Compared with the prior art, the invention has the following advantages:
(1) According to the invention, plant polyphenol is efficiently separated by using polyamide, and meanwhile, the sweet tea is comprehensively extracted by using the solubility difference of quercetin and ellagic acid, so that high-purity rubusoside, quercetin and ellagic acid are obtained, the comprehensive utilization value of the sweet tea is improved, and the economic benefit is greatly enhanced;
(2) The invention provides a brand-new method for extracting high-purity rubusoside, ellagic acid and quercetin from rubus suavissimus leaves, the purity of the rubusoside, the purity of the quercetin and the purity of the ellagic acid which are prepared are all higher than 95%, the recovery rate of 3 products is all higher than 90%, and the prepared 3 products have good color and luster and can be sold on the market as high-purity plant extracts;
(3) The method provided by the invention has the advantages of strong operability, low cost and no pollution, is suitable for industrial production, realizes comprehensive utilization of sweet tea resources, creates more considerable economic benefit, and solves the problem of environmental pollution caused by the sweet tea waste residue after the sweet tea glycoside is extracted by water.
Drawings
FIG. 1 is a HPLC detection result chart of rubusoside content in the supernatant obtained in step S1 in example 3 of the present invention;
FIG. 2 is a HPLC detection result chart of the quercetin content in the supernatant obtained in step S1 in example 3 of the present invention;
FIG. 3 is a HPLC detection result chart of the rubusoside content in the rubusoside pure product obtained in step S2 in example 3 of the present invention;
fig. 4 is a HPLC detection result chart of the quercetin content in the quercetin competitive product obtained in step S3 in embodiment 3 of the present invention;
fig. 5 is a HPLC detection result chart of the ellagic acid content in the ellagic acid refined product obtained in step S4 in example 3 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments.
It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In the examples, the means used are conventional in the art unless otherwise specified.
The terms "comprises," "comprising," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion.
For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
In addition, the technical features involved in the embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
The reagents and equipment used in the examples and comparative examples of the present invention were all commercially available products.
The sweet tea raw material used in the embodiment of the invention contains sweet tea glycoside, ellagic acid and quercetin 4.0-6.0wt%, 2.0-5.0wt% and 0.8-1.5wt%, respectively.
Example 1
The embodiment of the invention provides a method for comprehensively extracting rubusoside, quercetin and ellagic acid from rubus suavissimus, which specifically comprises the following steps:
(1) Washing, drying, extracting and concentrating
Cleaning the collected sweet tea leaves, vacuum drying at 50 deg.C to constant weight, pulverizing, and sieving with 20 mesh sieve. Weighing 1kg of sweet tea powder, adding 10L of 50% ethanol, performing reflux extraction at 80 deg.C, separating residue and filtrate, repeatedly extracting the residue with 10L of 50% ethanol under the above conditions, filtering, mixing the filtrates, concentrating the extractive solution, recovering ethanol until the extractive solution has no alcohol smell, centrifuging to remove insoluble substances to obtain supernatant;
(2) Rubusoside purification
And (2) feeding the supernatant obtained after centrifugation in the step (S1) onto a polyamide column at the flow rate of 1BV/h, collecting effluent liquid on the column, washing the supernatant with 1BV of deionized water at the flow rate of 2BV/h after sample loading to obtain water washing liquid, washing the supernatant with 3BV of 2% (mass concentration) NaOH aqueous solution at the flow rate of 2BV/h after water washing to obtain alkaline washing liquid, adjusting the pH of the alkaline washing liquid to 6.5, and concentrating the alkaline washing liquid to 1/6 of the original volume to obtain the sweet tea polyphenol concentrated solution containing the ellagitannin, the quercetin and derivatives thereof. Combining the polyamide column-loading effluent and the water washing liquid, loading the polyamide column-loading effluent and the water washing liquid on an AB-8 type macroporous resin column, loading the polyamide column-loading liquid at the flow rate of 1BV/h, washing the polyamide column-loading liquid with deionized water at the flow rate of 2BV/h for 5BV after loading, discarding the column-loading effluent and the water washing liquid, eluting the polyamide column-loading liquid and the water washing liquid with 65% ethanol at the flow rate of 2BV/h for 4BV to obtain an eluent, and concentrating the eluent to be dry to obtain the rubusoside crude product. Heating and dissolving the crude rubusoside with 200mL of deionized water, placing in a refrigerator at 4 ℃ for crystallizing for 28h, performing suction filtration, washing a filter cake for 3 times with ice water, and drying to obtain a pure rubusoside product 41.36g, wherein the content is 96.24% by HPLC (high performance liquid chromatography) and the recovery rate is 94.37%;
(3) Quercetin purification
And (3) taking the sweet tea polyphenol concentrated solution obtained in the step (S2), adding hydrochloric acid to enable the concentration of the hydrochloric acid to reach 2% (v/v), hydrolyzing at the constant temperature of 100 ℃ for 2h, cooling, filtering and separating solid and liquid, washing filter residues with deionized water until the filtrate is neutral, and obtaining the filter residues which are the sweet tea polyphenol hydrolysate. And adding 1000mL of 95% ethanol into the sweet tea polyphenol hydrolysate, heating to 60 ℃, stirring with ice, and filtering while hot to obtain a second filtrate and a second filter residue. Concentrating the second filtrate, standing at low temperature for crystallization, filtering, washing with water, drying to obtain quercetin refined product 12.78g, content by HPLC (high performance liquid chromatography) 97.11%, and recovery rate 93.91%;
(4) Ellagic acid purification
Dissolving the obtained second filter residue with 600mL of 2% NaOH aqueous solution, centrifuging to remove insoluble substances to obtain supernatant, adjusting the pH of the supernatant to be =3.0, performing acid precipitation, standing for 10h, filtering, washing with deionized water until the filtrate is neutral, drying the filter residue to obtain 39.58g of refined ellagic acid, wherein the content is 95.94% by HPLC (high performance liquid chromatography), and the recovery rate is 97.15%.
Example 2
The embodiment of the invention provides a method for comprehensively extracting rubusoside, quercetin and ellagic acid from rubus suavissimus, which specifically comprises the following steps:
(1) Washing, drying, extracting and concentrating
Cleaning the collected sweet tea leaves, vacuum drying at 50 deg.C to constant weight, pulverizing, and sieving with 30 mesh sieve. Weighing 2kg of sweet tea powder, adding 20L of 40% ethanol, performing reflux extraction at 75 deg.C, separating residue and filtrate, extracting the residue with 15L of 50% ethanol under the above conditions, filtering, mixing the filtrates, concentrating the extractive solution, recovering ethanol until the extractive solution has no alcohol smell, centrifuging to remove insoluble substances to obtain supernatant;
(2) Rubusoside purification
And (2) feeding the supernatant obtained after the centrifugation in the step (S1) onto a polyamide column at the flow rate of 1.5BV/h, collecting effluent liquid on the column, washing the supernatant with 1BV of deionized water at the flow rate of 3BV/h after the sample is loaded to obtain water washing liquid, washing the supernatant with 3BV of 3% (mass concentration) NaOH aqueous solution at the flow rate of 3BV/h after the water washing is completed to obtain alkaline washing liquid, adjusting the pH of the alkaline washing liquid to 6.0 by hydrochloric acid, and concentrating the alkaline washing liquid to 1/5 of the original volume to obtain the sweet tea polyphenol concentrated solution containing the ellagitannin, the quercetin and derivatives thereof. Combining the polyamide column-loading effluent and the water washing solution, loading on an AB-8 type macroporous resin column, loading at the flow rate of 1.5BV/h, washing with deionized water at the flow rate of 2BV/h for 5BV after loading is finished, discarding the column-loading effluent and the water washing solution, then eluting with 60% ethanol at the flow rate of 2BV/h for 4BV to obtain an eluent, and concentrating the eluent to dryness to obtain the rubusoside crude product. Heating and dissolving the crude rubusoside with 300mL of deionized water, placing in a refrigerator at 4 ℃ for crystallization for 30h, performing suction filtration, washing a filter cake with ice water for 3 times, and drying to obtain 84.17g of pure rubusoside, wherein the content is 95.19% by HPLC (high performance liquid chromatography) and the recovery rate is 97.34%;
(3) Quercetin purification
And (3) taking the sweet tea polyphenol concentrated solution obtained in the step (S2), adding sulfuric acid to enable the sulfuric acid concentration to reach 3% (v/v), hydrolyzing at the constant temperature of 110 ℃ for 3h, cooling, filtering and separating solid and liquid, washing filter residues with deionized water until the filtrate is neutral, and obtaining the filter residues which are the sweet tea polyphenol hydrolysate. 1400mL of 95% ethanol is added into the sweet tea polyphenol hydrolysate, the mixture is heated to 60 ℃ and stirred with ice, and the mixture is filtered while the mixture is hot, so that a second filtrate and a second filter residue are obtained. Concentrating the second filtrate, placing the second filtrate at low temperature for crystallization, filtering the second filtrate, washing filter residues with water, drying the filter residues to obtain 25.19g of a quercetin refined product, measuring the content by HPLC to be 96.16%, and obtaining the recovery rate to be 94.75%;
(4) Ellagic acid purification
And denaturing and dissolving the obtained second filter residue by using 1000mL of 3% NaOH aqueous solution, centrifuging to remove insoluble substances to obtain supernatant, adjusting the pH of the supernatant to be =2.5, carrying out renaturation precipitation, standing for 8h, filtering, washing with deionized water until the filtrate is neutral, drying the filter residue to obtain refined ellagic acid 80.06g, wherein the content of the ellagic acid is 96.37% by HPLC (high performance liquid chromatography), and the recovery rate is 93.95%.
Example 3
The embodiment of the invention provides a method for comprehensively extracting rubusoside, quercetin and ellagic acid from rubus suavissimus, which specifically comprises the following steps:
(1) Washing, drying, extracting and concentrating
Cleaning the collected sweet tea leaves, vacuum drying at 50 deg.C to constant weight, pulverizing, and sieving with 20 mesh sieve. Weighing sweet tea powder 10kg, adding 50% ethanol 10L, reflux extracting at 80 deg.C, separating residue and filtrate, extracting the residue twice with 6L 50% ethanol under the above conditions, filtering, mixing the filtrates obtained 3 times, concentrating the obtained extractive solution, recovering ethanol until the extractive solution has no alcohol smell, centrifuging to remove insoluble substances to obtain supernatant, and measuring the content of rubusoside (shown in figure 1) and quercetin (shown in figure 2) in the supernatant by HPLC to be 3.59% and 2.84%, respectively;
(2) Rubusoside purification
And (2) feeding the supernatant obtained after the centrifugation in the step (S1) to a polyamide column at the flow rate of 0.8BV/h, collecting effluent liquid on the column, washing the supernatant with 1.5BV of deionized water at the flow rate of 2BV/h after the sample is fed to obtain water washing liquid, washing the supernatant with 3BV of 2.5% (mass concentration) NaOH aqueous solution at the flow rate of 2BV/h after the water washing is finished to obtain alkaline washing liquid, adjusting the pH of the alkaline washing liquid to be 6.0 by using hydrochloric acid, and concentrating the alkaline washing liquid to 1/6 of the original volume to obtain the sweet tea polyphenol concentrated solution containing the ellagitannin, the quercetin and derivatives thereof. Combining the polyamide column-loading effluent and the water washing solution, loading on an AB-8 type macroporous resin column, loading at the flow rate of 0.8BV/h, washing with deionized water at the flow rate of 2BV/h for 5BV after loading is finished, discarding the column-loading effluent and the water washing solution, then eluting with 60% ethanol at the flow rate of 2BV/h for 3.5BV to obtain an eluent, and concentrating the eluent to dryness to obtain the rubusoside crude product. Heating and dissolving the crude rubusoside with 1.8L of deionized water, placing in a refrigerator at 4 deg.C for 36h, vacuum-filtering, washing the filter cake with ice water for 3 times, drying to obtain pure rubusoside 410.49g, with purity of 97.56% by HPLC (as shown in FIG. 3) and recovery rate of 95.52%;
(3) Quercetin purification
And (3) taking the sweet tea polyphenol concentrated solution obtained in the step (S2), adding hydrochloric acid to enable the concentration of hydrochloric acid to reach 4% (v/v), carrying out constant-temperature hydrolysis at 100 ℃ for 4h, cooling, filtering and separating solid and liquid, washing filter residues with deionized water until the filtrate is neutral, and obtaining the filter residues which are sweet tea polyphenol hydrolysate. Adding 12L of 95% ethanol into sweet tea polyphenol hydrolysate, heating to 60 deg.C, stirring with ice, and filtering while hot to obtain second filtrate and second filter residue. Concentrating the second filtrate, crystallizing at low temperature, filtering, washing with water, drying to obtain refined quercetin product 130.08g, content of 96.16% by HPLC (as shown in figure 4), and recovery rate of 95.84%;
(4) Ellagic acid purification
Dissolving the obtained second filter residue with 5L of 2.5% NaOH aqueous solution, centrifuging to remove insoluble substances to obtain supernatant, adjusting pH =3.0 of the supernatant, performing acid precipitation, standing for 8h, filtering, washing with deionized water until the filtrate is neutral, drying the filter residue to obtain refined ellagic acid 403.24g, with content of 95.94% by HPLC (shown in figure 5), and recovering 94.37%.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention.
It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent should be subject to the appended claims.
Claims (10)
1. A method for comprehensively extracting rubusoside, quercetin and ellagic acid from sweet tea is characterized in that,
the method comprises the following steps:
s1, separation of Polyamide
Subjecting the supernatant obtained after sweet tea extraction to polyamide column, collecting effluent liquid on the column, washing with water after sample loading to obtain water washing liquid, and eluting with alkali water after water washing to obtain alkali washing liquid;
s2, rubusoside purification
Mixing the effluent liquid and the water washing liquid in the step S1, loading the effluent liquid and the water washing liquid into a macroporous adsorption resin column, washing with water after the sample loading is finished, eluting with an ethanol water solution after the washing with water is finished, concentrating the obtained ethanol eluent to dryness, and purifying to obtain rubusoside;
s3, acid hydrolysis
Adding hydrochloric acid into the alkaline washing liquid in the S1 to adjust the pH value to be weakly acidic, adding acid for acidification after concentration, heating for hydrolysis, carrying out solid-liquid separation on the obtained hydrolysate, and cleaning the obtained first filter residue with deionized water until the water washing liquid is neutral to obtain the sweet tea polyphenol hydrolysate;
s4, purifying quercetin
Adding a 95v% ethanol aqueous solution into the sweet tea polyphenol hydrolysate in the step S3, heating, stirring and filtering while the mixture is hot to obtain a second filtrate and a second filter residue, concentrating the second filtrate, standing at a low temperature for crystallization, and sequentially performing suction filtration, water washing and drying to obtain quercetin;
s5, ellagic acid purification
And (3) dissolving the second filter residue in the S4 with alkali water, removing insoluble substances to obtain a second supernatant, adding acid into the second supernatant for acid precipitation, standing, filtering, and washing with deionized water until the second supernatant is neutral to obtain ellagic acid.
2. The method for the integrated extraction of rubusoside, quercetin and ellagic acid in rubus suavissimus according to claim 1, wherein,
in the step S1, the process of the step S,
the flow rate of the supernatant liquid on the upper column is 0.5-1.5BV/h;
and/or the elution volume and the elution flow rate of the water washing are respectively 1-2BV and 2-4BV/h;
and/or the alkaline water is 1-5wt% NaOH aqueous solution;
and/or the elution volume and the elution flow rate of the alkaline water elution are respectively 2-5BV and 2-4BV/h.
3. The method for the integrated extraction of rubusoside, quercetin and ellagic acid in rubus suavissimus according to claim 1, wherein,
in the step S3, the process is carried out,
the addition amount of the hydrochloric acid is controlled to be 5.5-6.5;
and/or, the concentration multiple is 5-10 times;
and/or the temperature and the time of the heating hydrolysis are 100-120 ℃ and 1-5h respectively.
4. The method for the integrated extraction of rubusoside, quercetin and ellagic acid in rubus suavissimus according to any one of claims 1 to 3,
in the step S4, the process is carried out,
the addition amount of the 95v% ethanol aqueous solution is 5-50mL corresponding to 1g of sweet tea polyphenol hydrolysate;
and/or the heating temperature is 50-60 ℃.
5. The method for the integrated extraction of rubusoside, quercetin and ellagic acid in rubus suavissimus according to any one of claims 1 to 3,
in the step S5, the process is carried out,
the alkaline water is 1-5wt% NaOH aqueous solution;
and/or the adding mass of the alkaline water is 10-100 times of that of the second filter residue;
and/or, the acid precipitation is specifically carried out by adding acid to adjust the pH value to 2-4 and standing for 5-20h.
6. The method for the integrated extraction of rubusoside, quercetin and ellagic acid from rubus suavissimus according to any one of claims 1 to 5,
in the step S2, the process is carried out,
the flow rate of the macroporous adsorption resin on the column is 0.5-1.5BV/h;
and/or the elution volume and the elution flow rate of the water washing are respectively 4-6BV and 2-4BV/h;
and/or the concentration, the elution volume and the elution flow rate of the ethanol aqueous solution are respectively 55-75v%, 2-5BV and 2-4BV/h.
7. The method for the integrated extraction of rubusoside, quercetin and ellagic acid from rubus suavissimus according to any one of claims 1 to 6,
in the step S2, the first step is performed,
the purification treatment comprises adding a certain proportion of solvent, heating for redissolution, crystallizing, filtering and drying to obtain the product;
preferably, the solvent is deionized water or ethanol water, and the crystallization temperature and time are 2-10 ℃ and 12-48h respectively.
8. The method for the integrated extraction of rubusoside, quercetin and ellagic acid from rubus suavissimus according to any one of claims 1 to 7,
further comprising:
s0, drying, extracting and concentrating
Cleaning folium Hydrangeae Strigosae, drying to constant weight, pulverizing, sieving with 20-50 mesh sieve, adding 40-70v% ethanol water solution, heating and reflux extracting for several times, mixing extractive solutions, concentrating, recovering ethanol until no alcohol smell is produced, and centrifuging to remove insoluble substances to obtain supernatant.
9. The method for the integrated extraction of rubusoside, quercetin and ellagic acid in rubus suavissimus according to claim 8, wherein,
in the step S0, the process is carried out,
the drying temperature is 40-60 ℃;
and/or the temperature of the heating reflux is 70-100 ℃;
and/or, in the heating reflux process, the feed-liquid ratio is controlled to be 1g:5-30 mL;
and/or the times of heating reflux are 2-3 times;
and/or the heating reflux time is 30-90min.
10. Use of the method of any one of claims 1-9 for the integrated extraction of rubusoside, quercetin and ellagic acid from rubus suavissimus.
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