CN115197287B - Method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea and application of method - Google Patents
Method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea and application of method Download PDFInfo
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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 97
- 241001122767 Theaceae Species 0.000 title claims abstract description 58
- 235000009508 confectionery Nutrition 0.000 title claims abstract description 57
- 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 51
- 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 51
- 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 48
- 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 48
- 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 48
- 229960001285 quercetin Drugs 0.000 title claims abstract description 48
- 235000005875 quercetin Nutrition 0.000 title claims abstract description 48
- 229920002079 Ellagic acid Polymers 0.000 title claims abstract description 46
- 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 46
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 title claims abstract description 46
- 229960002852 ellagic acid Drugs 0.000 title claims abstract description 46
- 235000004132 ellagic acid Nutrition 0.000 title claims abstract description 46
- 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 46
- 238000000034 method Methods 0.000 title claims abstract description 38
- 150000008442 polyphenolic compounds Chemical class 0.000 claims abstract description 24
- 235000013824 polyphenols Nutrition 0.000 claims abstract description 24
- 238000000746 purification Methods 0.000 claims abstract description 20
- 239000004952 Polyamide Substances 0.000 claims abstract description 13
- 229920002647 polyamide Polymers 0.000 claims abstract description 13
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
- 239000000243 solution Substances 0.000 claims description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 239000006228 supernatant Substances 0.000 claims description 28
- 239000007788 liquid Substances 0.000 claims description 27
- 238000010438 heat treatment Methods 0.000 claims description 23
- 238000011068 loading method Methods 0.000 claims description 23
- 239000008367 deionised water Substances 0.000 claims description 21
- 229910021641 deionized water Inorganic materials 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 238000001035 drying Methods 0.000 claims description 19
- 239000000706 filtrate Substances 0.000 claims description 19
- 238000001914 filtration Methods 0.000 claims description 17
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- 238000010992 reflux Methods 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
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- 239000002253 acid Substances 0.000 claims description 8
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 238000003916 acid precipitation Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 108010009736 Protein Hydrolysates Proteins 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
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- 238000000967 suction filtration Methods 0.000 claims description 4
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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
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229920001968 ellagitannin Polymers 0.000 description 4
- JMGCAHRKIVCLFW-CNWXVVPTSA-N ellagitannin Chemical compound OC1=C(O)C(O)=CC(C(=O)O[C@H]2C3=C4C(=O)O[C@@H]2[C@@H]2[C@@H]5OC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C=C6C(=O)OC[C@H]5OC(=O)C5=CC(O)=C(O)C(O)=C5C=5C(O)=C(O)C(O)=C(C=5C(=O)O2)C4=C(O)C(O)=C3O)=C1 JMGCAHRKIVCLFW-CNWXVVPTSA-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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- 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
- C07D311/28—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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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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- C—CHEMISTRY; METALLURGY
- 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 in sweet tea, 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 utilizing polyamide, and meanwhile, the sweet tea is comprehensively extracted by utilizing the solubility difference of quercetin and ellagic acid, so that high-purity rubusoside, quercetin and ellagic acid are obtained, the comprehensive utilization value of sweet tea is improved, and the economic benefit is greatly enhanced; the purities of the rubusoside, the quercetin and the ellagic acid prepared by the method are all higher than 95%, the recovery rate is higher than 90%, and the product has good color; the method provided by the invention has the advantages of strong operability in the technical process, low cost and no pollution, is suitable for industrial production, not only realizes comprehensive utilization of sweet tea resources, but also solves the problem of environmental pollution of sweet tea waste residues after water extraction of rubusoside.
Description
Technical Field
The invention relates to the technical field of extraction of plant active ingredients, in particular to a method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea and application thereof.
Background
The sweet tea contains rich bioactive components including rubusoside, quercetin, ellagic acid, etc.
Ellagic acid is a natural polyphenol with molecular formula of C 14H6O8, which exists in condensed form in nature, while free ellagic acid usually exists 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 properties, and can inhibit proliferation of human immunodeficiency virus; ellagic acid is also coagulant, has good inhibitory effect on various bacteria and viruses, and can prevent infection and inhibit ulcer. In addition, ellagic acid has various physiological effects of lowering blood pressure, tranquilizing, and preventing osteoporosis.
Quercetin is mainly in the form of glycoside in vegetables, fruits, tea, wine and the like, is dietary polyphenol, can benefit from the protection effect of the quercetin by eating or serving as a food supplement, and has wide sources, safety and easy availability compared with chemical preparations. The anti-diabetic, antihypertensive, anti-Alzheimer's, anti-arthritic, anti-influenza virus, anti-microbial infection, anti-aging, autophagy-affecting and cardiovascular protection effects of quercetin have been widely studied, and recently, anticancer activity studies on different cancer cell lines have also been reported.
In the industrial production of rubusoside, because only high-purity rubusoside is needed to be obtained, in the whole production process, various effective component ingredients including ellagitannin, quercetin and glycosides thereof are discharged as waste liquid and waste residues, so that serious waste is caused on biological resources of the rubusoside, higher economic value cannot be created, the treatment difficulty of three industrial wastes is increased, the pollution of water sources and soil is caused, and the sustainable development of industry is not facilitated.
So far, no report on a method which can comprehensively extract rubusoside, quercetin and ellagic acid in sweet tea, is simple and environment-friendly, has stable process and is suitable for industrialized mass production is available.
In view of this, the present invention has been made.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention provides a method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea and application thereof.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
A method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea comprises the following steps:
S1, polyamide separation
Loading the supernatant obtained after sweet tea extraction on a polyamide column, collecting effluent liquid from the column, washing with water after loading to obtain a water washing solution, and eluting with alkaline water after washing to obtain an alkaline washing solution;
S2, rubusoside purification
Combining the effluent liquid of the upper column in the step S1 with the water washing liquid, loading the mixture on a macroporous adsorption resin column, washing the mixture after loading, eluting the mixture with ethanol water solution after washing, concentrating the obtained ethanol eluent to dryness, and purifying the ethanol eluent to obtain rubusoside;
S3, acidolysis
Adding hydrochloric acid into the alkaline washing liquid in the step S1 to adjust the pH to be weak acid, adding acid for acidification after concentrating, then heating for hydrolysis, carrying out solid-liquid separation on the obtained hydrolysate, and washing the obtained first filter residue with deionized water until the washing liquid is neutral to obtain sweet tea polyphenol hydrolysate;
S4, quercetin purification
Adding 95v% ethanol water solution into the sweet tea polyphenol hydrolysate in the step S3, heating, stirring and filtering while the sweet tea polyphenol hydrolysate is hot to obtain second filtrate and second filter residue, concentrating the second filtrate, standing at a low temperature for crystallization, and sequentially carrying out suction filtration, water washing and drying to obtain quercetin;
S5, ellagic acid purification
Dissolving the second filter residue in the step S4 with alkaline 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 solution is neutral to obtain ellagic acid.
In the technical scheme, in the step S1, the upper column flow rate of the supernatant is 0.5-1.5BV/h.
In the technical scheme, in the step S1, the eluting volume and the eluting flow rate of the water washing are respectively 1-2BV and 2-4BV/h.
In the above technical scheme, in step S1, the alkaline water is 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 elution are respectively 2-5BV and 2-4BV/h.
In the above technical solution, in step S3, the adding amount of the hydrochloric acid is to control the pH thereof to be 5.5-6.5.
In the above technical solution, in step S3, the multiple of concentration is 5-10 times.
In the above technical scheme, in step S3, the temperature and time of the thermal hydrolysis are 100-120 ℃ and 1-5 hours, respectively.
Further, in the above technical scheme, in step S4, the amount of the 95v% aqueous ethanol solution added is 5-50mL, corresponding to 1g of sweet tea polyphenol hydrolysate.
Further, in the above technical scheme, in step S4, the heating temperature is 50-60 ℃.
Further, in the above technical scheme, in step S5, the alkaline water is 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 that of the second filter residue.
Further, in the above technical scheme, in step S5, the acid precipitation is specifically performed by adding acid to adjust the pH to 2-4, and standing for 5-20 hours.
In the technical scheme, in the step S2, the flow rate of the macroporous adsorption resin on the column is 0.5-1.5BV/h.
In the above technical scheme, in step S2, the eluting volume and the eluting flow rate of the water wash are 4-6BV and 2-4BV/h, respectively.
Still further, in the above technical scheme, in step S2, the concentration, the elution volume and the elution flow rate of the aqueous ethanol solution are 55-75v%, 2-5BV and 2-4BV/h, respectively.
In the above technical scheme, in 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 12-48 hours, respectively.
In one specific embodiment of the present invention, the method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea further comprises:
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 ethanol smell, centrifuging to remove insoluble substances, and collecting supernatant.
Specifically, in the above technical scheme, in step S0, the drying temperature is 40-60 ℃.
Specifically, in the above technical scheme, in step S0, the temperature of the heating reflux is 70-100 ℃.
Specifically, in the above technical solution, in step S0, in the heating reflux process, the feed liquid ratio is controlled to be 1g:5-30mL.
Specifically, in the above technical solution, in step S0, the number of times of heating reflux is 2-3 times.
Specifically, in the above technical solution, in step S0, the heating reflux time is 30-90min.
The invention also provides an application of the method in comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea.
Compared with the prior art, the invention has the following advantages:
(1) According to the invention, plant polyphenol is efficiently separated by utilizing polyamide, and meanwhile, the sweet tea is comprehensively extracted by utilizing the solubility difference of quercetin and ellagic acid, so that high-purity rubusoside, quercetin and ellagic acid are obtained, the comprehensive utilization value of 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 sweet tea, wherein the purities of the prepared rubusoside, quercetin and ellagic acid are higher than 95%, the recovery rates of 3 products are higher than 90%, and the prepared 3-stage product has good color and luster, and can be sold on the market as a high-purity plant extract;
(3) The method provided by the invention has the advantages of strong operability in the technical process, low cost and no pollution, is suitable for industrial production, realizes comprehensive utilization of sweet tea resources, creates considerable economic benefit, and solves the problem of environmental pollution of sweet tea waste residues after water extraction of rubusoside.
Drawings
FIG. 1 is a graph showing the HPLC detection result of the content of rubusoside in the supernatant obtained in the step S1 in the embodiment 3 of the present invention;
FIG. 2 is a graph showing the results of HPLC detection of the quercetin content in the supernatant obtained in step S1 of example 3 of the present invention;
FIG. 3 is a graph showing the HPLC detection result of the content of rubusoside in the pure rubusoside product obtained in step S2 in example 3 of the present invention;
FIG. 4 is a graph showing the results of HPLC detection of the content of quercetin in the refined quercetin product obtained in step S3 of example 3 of the present invention;
FIG. 5 is a graph showing the results of HPLC detection of the ellagic acid content in the ellagic acid concentrate obtained in step S4 of example 3 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present invention more apparent.
It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
In the examples, all means used are conventional in the art unless otherwise specified.
The terms "comprising," "including," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion.
For example, a composition, step, 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, step, method, article, or apparatus.
In addition, the technical features of the embodiments of the present invention described below may be combined with each other as long as they do not collide with each other.
The reagents and apparatus used in the examples and comparative examples of the present invention are commercially available products.
The sweet tea raw materials used in the embodiment of the invention have the contents of 4.0-6.0wt%, 2.0-5.0wt% and 0.8-1.5wt% of rubusoside, ellagic acid and quercetin respectively.
Example 1
The embodiment of the invention provides a method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea, which comprises the following steps:
(1) Washing, drying, extracting and concentrating
Cleaning the collected sweet tea leaves, vacuum drying at 50deg.C to constant weight, pulverizing, and sieving with 20 mesh sieve. Weighing 1kg of sweet tea powder, adding 10L of 50% ethanol, reflux-extracting at 80deg.C, separating filter residue and filtrate, repeatedly extracting the filter 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 ethanol smell, centrifuging to remove insoluble substances, and collecting supernatant;
(2) Rubusoside purification
And (3) loading the supernatant obtained after the centrifugation in the step (S1) on a polyamide column at a flow rate of 1BV/h, collecting effluent of the loading, washing with deionized water of 1BV at a flow rate of 2BV/h to obtain a water washing solution, washing with NaOH aqueous solution of 3BV concentration of 2% (mass concentration) at a flow rate of 2BV/h to obtain an alkaline washing solution, adjusting the pH of the alkaline washing solution to 6.5, and concentrating to 1/6 of the original volume to obtain the sweet tea polyphenol concentrated solution containing ellagitannin, quercetin and derivatives thereof. And (3) combining the polyamide column effluent and the water washing liquid, loading on an AB-8 type macroporous resin column, loading according to the flow rate of 1BV/h, washing 5BV with deionized water at the flow rate of 2BV/h after loading is completed, discarding the column effluent and the water washing liquid, eluting 4BV with 65% ethanol at the flow rate of 2BV/h 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 crystallization for 28h, carrying out suction filtration, washing a filter cake with ice water for 3 times, and drying to obtain 41.36g of pure rubusoside with the content of 96.24% measured by HPLC and the recovery rate of 94.37%;
(3) Quercetin purification
And (2) 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 for 2 hours at a constant temperature of 100 ℃, cooling after hydrolysis, filtering to separate solid and liquid, washing filter residues with deionized water until the filter liquor is neutral, and obtaining filter residues which are sweet tea polyphenol hydrolysate. 1000mL 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 to obtain second filtrate and second filter residue. Concentrating the second filtrate, standing at low temperature for crystallization, filtering, washing the filter residue with water, and drying to obtain quercetin refined product 12.78g, wherein the content measured by HPLC is 97.11%, and the recovery rate is 93.91%;
(4) Ellagic acid purification
The second filter residue obtained is dissolved by 600mL of 2% NaOH aqueous solution, insoluble matters are removed by centrifugation to obtain supernatant, the pH=3.0 of the supernatant is adjusted for acid precipitation, the supernatant is kept stand for 10 hours and filtered, deionized water is used for washing until the filtrate is neutral, the filter residue is dried to obtain refined ellagic acid product 39.58g, the content measured by HPLC is 95.94%, 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 in sweet tea, which comprises the following steps:
(1) Washing, drying, extracting and concentrating
The collected sweet tea leaves are cleaned and dried to constant weight in vacuum at 50 ℃, crushed and sieved by a 30-mesh sieve. Weighing 2kg of sweet tea powder, adding 40% ethanol 20L, reflux-extracting at 75deg.C, separating filter residue and filtrate, repeatedly extracting the filter 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 ethanol smell, centrifuging to remove insoluble substances, and collecting supernatant;
(2) Rubusoside purification
And (3) loading the supernatant obtained after the centrifugation in the step (S1) on a polyamide column at a flow rate of 1.5BV/h, collecting effluent from the column, washing with deionized water of 1BV at a flow rate of 3BV/h after the loading is finished to obtain a water washing liquid, washing with NaOH aqueous solution of 3BV concentration (mass concentration) at a flow rate of 3BV/h after the washing is finished to obtain an alkaline washing liquid, adjusting the pH of the alkaline washing liquid to 6.0 by hydrochloric acid, and concentrating to 1/5 of the original volume to obtain the sweet tea polyphenol concentrated solution containing ellagitannin, quercetin and derivatives thereof. And (3) combining the polyamide column effluent and the water washing liquid, loading on an AB-8 type macroporous resin column, loading according to the flow rate of 1.5BV/h, washing with deionized water at the flow rate of 2BV/h for 5BV after loading is completed, discarding the column effluent and the water washing liquid, eluting with 60% 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 300mL of deionized water, placing in a refrigerator at 4 ℃ for crystallization for 30h, carrying out suction filtration, washing a filter cake with ice water for 3 times, and drying to obtain 84.17g of pure rubusoside with 95.19% of HPLC content and 97.34% of recovery rate;
(3) Quercetin purification
And (2) taking the sweet tea polyphenol concentrated solution obtained in the step (S2), adding sulfuric acid to enable the concentration of the sulfuric acid to reach 3% (v/v), hydrolyzing at the constant temperature of 110 ℃ for 3 hours, cooling after the hydrolysis is completed, filtering to separate solid and liquid, washing filter residues with deionized water until the filter liquor is neutral, and obtaining the filter residues which are 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 to obtain second filtrate and second filter residue. Concentrating the second filtrate, standing at low temperature for crystallization, filtering, washing the filter residue with water, and drying to obtain quercetin refined product 25.19g, wherein the content measured by HPLC is 96.16%, and the recovery rate is 94.75%;
(4) Ellagic acid purification
The second filter residue obtained is denatured and dissolved by 1000mL of 3% NaOH aqueous solution, insoluble matters are removed by centrifugation to obtain supernatant, pH=2.5 of the supernatant is regulated for renaturation and precipitation, the supernatant is kept stand for 8 hours and filtered and washed by deionized water until the filtrate is neutral, 80.06g of ellagic acid refined product is obtained after the filter residue is dried, the content measured by HPLC is 96.37%, 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 in sweet tea, which comprises the following steps:
(1) Washing, drying, extracting and concentrating
Cleaning the collected sweet tea leaves, vacuum drying at 50deg.C to constant weight, pulverizing, and sieving with 20 mesh sieve. Weighing 10kg of sweet tea powder, adding 10L of 50% ethanol, reflux-extracting at 80deg.C, separating filter residue and filtrate, repeatedly extracting the filter residue with 6L of 50% ethanol twice under the above conditions, filtering, mixing the filtrates obtained 3 times, concentrating the obtained extractive solution, recovering ethanol until the extractive solution has no ethanol smell, centrifuging to remove insoluble substances to obtain supernatant, wherein the content of rubusoside (shown in figure 1) and quercetin (shown in figure 2) in the supernatant is 3.59% and 2.84% respectively;
(2) Rubusoside purification
And (3) loading the supernatant obtained after the centrifugation in the step (S1) on a polyamide column at a flow rate of 0.8BV/h, collecting effluent from the column, washing with deionized water of 1.5BV at a flow rate of 2BV/h to obtain a water washing solution, washing with NaOH aqueous solution of 3BV concentration of 2.5% (mass concentration) at a flow rate of 2BV/h to obtain an alkaline washing solution, regulating the pH of the alkaline washing solution to 6.0 by using hydrochloric acid, and concentrating to 1/6 of the original volume to obtain the sweet tea polyphenol concentrated solution containing ellagitannin, quercetin and derivatives thereof. And (3) combining the polyamide column-loading effluent and the water washing liquid, loading on an AB-8 type macroporous resin column at a flow rate of 0.8BV/h, washing with deionized water at a flow rate of 2BV/h for 5BV after loading, discarding the column-loading effluent and the water washing liquid, eluting with 60% ethanol at a flow rate of 2BV/h for 3.5BV to obtain an eluent, and concentrating the eluent to be dry to obtain a rubusoside crude product. Dissolving crude rubusoside with 1.8L deionized water under heating, crystallizing in refrigerator at 4deg.C for 36 hr, suction filtering, washing the filter cake with ice water for 3 times, and drying to obtain pure rubusoside 410.49g with HPLC content of 97.56% (shown in figure 3) and recovery rate of 95.52%;
(3) Quercetin purification
And (2) 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 4% (v/v), hydrolyzing for 4 hours at a constant temperature of 100 ℃, cooling after hydrolysis, filtering to separate solid and liquid, washing filter residues with deionized water until the filter liquor is neutral, and obtaining filter residues which are sweet tea polyphenol hydrolysate. Adding 12L of 95% ethanol into the sweet tea polyphenol hydrolysate, heating to 60 ℃ and 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 the filter residue with water, and drying to obtain refined quercetin 130.08g with content 96.16% (shown in figure 4) by HPLC, and recovery rate of 95.84%;
(4) Ellagic acid purification
The second filter residue obtained is dissolved by 5L of 2.5% NaOH aqueous solution, insoluble matters are removed through centrifugation to obtain supernatant, the pH=3.0 of the supernatant is adjusted for acid precipitation, the supernatant is kept stand for 8 hours and filtered and washed by deionized water until the filtrate is neutral, 403.24g of ellagic acid refined product is obtained after the filter residue is dried, the content of the ellagic acid refined product is 95.94 percent (shown in figure 5) through HPLC, and the recovery rate is 94.37 percent.
The above examples illustrate only a few embodiments of the invention, which are described in detail and are not to be construed as limiting the scope of the invention.
It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (6)
1. A method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea is characterized in that,
Comprising the following steps:
S0, drying, extracting and concentrating
Cleaning folium Hydrangeae Strigosae, drying to constant weight, pulverizing, sieving with 20-50 mesh sieve, adding 40-70 v% ethanol water solution, heating and reflux extracting for several times, mixing extractive solutions, concentrating, recovering ethanol until no ethanol smell, centrifuging to remove insoluble substances, and collecting supernatant;
S1, polyamide separation
Loading the supernatant obtained after sweet tea extraction on a polyamide column, collecting effluent liquid from the column, washing with water after loading to obtain a water washing solution, and eluting with alkaline water after washing to obtain an alkaline washing solution;
S2, rubusoside purification
Combining the effluent liquid of the upper column in the step S1 with the water washing liquid, loading the mixture on a macroporous adsorption resin column, washing the mixture after loading, eluting the mixture with ethanol water solution after washing, concentrating the obtained ethanol eluent to dryness, and purifying the ethanol eluent to obtain rubusoside;
S3, acidolysis
Adding hydrochloric acid into the alkaline washing liquid in the step S1 to adjust the pH to be weak acid, adding acid for acidification after concentrating, then heating for hydrolysis, carrying out solid-liquid separation on the obtained hydrolysate, and washing the obtained first filter residue with deionized water until the washing liquid is neutral to obtain sweet tea polyphenol hydrolysate;
S4, quercetin purification
Adding 95 v% ethanol water solution into the sweet tea polyphenol hydrolysate in the step S3, heating, stirring and filtering while the sweet tea polyphenol hydrolysate is hot to obtain second filtrate and second filter residue, concentrating the second filtrate, standing at a low temperature for crystallization, and sequentially carrying out suction filtration, water washing and drying to obtain quercetin;
S5, ellagic acid purification
Dissolving the second filter residue in the step S4 with alkaline 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 solution is neutral to obtain ellagic acid;
In the step S3 of the process,
The adding amount of the hydrochloric acid is controlled to be 5.5-6.5 in pH;
And, the multiple of the concentration is 5-10 times;
And the temperature and time of the heating hydrolysis are respectively 100-120 ℃ and 1-5 h;
in the step S5 of the process,
The alkaline water is 1-5 wt% NaOH aqueous solution;
And the adding mass of the alkaline water is 10-100 times of that of the second filter residue;
and the acid precipitation is specifically carried out by adding acid to adjust the pH to 2-4 and standing for 5-20 h;
in the step S2 of the process,
The purification treatment comprises adding a certain proportion of solvent, heating for redissolution, crystallizing, filtering, and drying to obtain the final product;
The solvent is deionized water or ethanol water solution, and the crystallization temperature and time are respectively 2-10 ℃ and 12-48 h.
2. The method for comprehensively extracting rubusoside, quercetin and ellagic acid from sweet tea according to claim 1, wherein,
In the step S1 of the process,
The flow rate of the supernatant on the column is 0.5-1.5 BV/h;
and/or the elution volume and elution flow rate of the water wash are 1-2 BV and 2-4 BV/h respectively;
And/or, the alkaline water is 1-5 wt% NaOH aqueous solution;
and/or the volume and flow rate of the alkaline water are 2-5 BV and 2-4 BV/h respectively.
3. The method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea according to any one of claims 1 to 2, wherein,
In the step S4 of the process,
The addition amount of the 95 v% ethanol water solution is 5-50 mL corresponding to 1g sweet tea polyphenol hydrolysate;
And/or the heating temperature is 50-60 ℃.
4. The method for comprehensively extracting rubusoside, quercetin and ellagic acid in sweet tea according to any one of claims 1 to 2, wherein,
In the step S2 of the process,
The flow rate of the macroporous adsorption resin on the column is 0.5-1.5 BV/h;
And/or the elution volume and elution flow rate of the water wash are 4-6 BV and 2-4 BV/h respectively;
And/or the concentration, elution volume and elution flow rate of the aqueous ethanol solution are 55-75 v%, 2-5 BV and 2-4BV/h, respectively.
5. The method for comprehensively extracting rubusoside, quercetin and ellagic acid from sweet tea according to claim 1, wherein,
In the step S0 of the process,
The drying temperature is 40-60 ℃;
and/or, the temperature of the heating reflux is 70-100 ℃;
And/or in the heating reflux process, controlling the feed liquid ratio to be 1 g:5-30 mL;
And/or the number of times of heating reflux is 2-3 times;
and/or the heating reflux time is 30-90 min.
6. Use of the method according to any one of claims 1-5 for the integrated extraction of rubusoside, quercetin and ellagic acid in sweet tea.
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