CN112174977A - Method for extracting ellagic acid from oil tea fruit shell - Google Patents
Method for extracting ellagic acid from oil tea fruit shell Download PDFInfo
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- CN112174977A CN112174977A CN202011233554.8A CN202011233554A CN112174977A CN 112174977 A CN112174977 A CN 112174977A CN 202011233554 A CN202011233554 A CN 202011233554A CN 112174977 A CN112174977 A CN 112174977A
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- acid
- ellagic acid
- camellia oleifera
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- 229920002079 Ellagic acid Polymers 0.000 title claims abstract description 53
- 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 53
- 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 53
- 235000004132 ellagic acid Nutrition 0.000 title claims abstract description 53
- 229960002852 ellagic acid Drugs 0.000 title claims abstract description 53
- 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 53
- 238000000034 method Methods 0.000 title claims abstract description 20
- 235000013399 edible fruits Nutrition 0.000 title claims abstract description 14
- 241001122767 Theaceae Species 0.000 title claims abstract description 13
- 241000526900 Camellia oleifera Species 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000010298 pulverizing process Methods 0.000 claims abstract description 3
- 238000007873 sieving Methods 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 240000001548 Camellia japonica Species 0.000 claims 2
- 235000018597 common camellia Nutrition 0.000 claims 2
- 238000000605 extraction Methods 0.000 abstract description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229920001864 tannin Polymers 0.000 description 6
- 235000018553 tannin Nutrition 0.000 description 6
- 239000001648 tannin Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229920002770 condensed tannin Polymers 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 206010062129 Tongue neoplasm Diseases 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 230000002019 anti-mutation Effects 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920001968 ellagitannin Polymers 0.000 description 1
- 201000004101 esophageal cancer Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 201000006134 tongue cancer Diseases 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- 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
Abstract
The invention provides a method for extracting ellagic acid from oil tea fruit shells, which is characterized by comprising the following steps: 1) drying oil tea fruit shell in the sun, pulverizing and sieving for use; 2) adding an acid solution, stirring and extracting, and collecting the solution after reaction; 3) the collected solution is further purified to prepare ellagic acid. According to the method, the camellia oleifera shells are crushed and sieved and then added with the acid solution for stirring and extraction, so that the extraction rate of ellagic acid in the camellia oleifera shells can be greatly improved, and the additional value of the camellia oleifera shells is improved.
Description
Technical Field
The invention belongs to the field of substance extraction, and particularly relates to a method for extracting ellagic acid from oil tea shells.
Background
The camellia oleifera shells are shells outside camellia oleifera fruits, are rich in tannin, and have the component composition shown in table 1.
TABLE 1 composition of Camellia oleifera shells
At present, tannins are classified into hydrolyzed tannins, condensed tannins, and tannins in which the condensed tannins and glucose in the hydrolyzed tannins are linked by a carbon-carbon bond, and the main active ingredients of the hydrolyzed tannins are gallic acid and ellagic acid. Ellagic Acid (Ellagic Acid) is a natural polyphenol component widely present in plant tissues of various soft fruits, nuts, etc., and is a dimeric derivative of gallic Acid, which is a polyphenol dilactone. It can exist not only in free form but also in more condensed form (such as ellagitannins, glycosides, etc.) in nature. Ellagic acid has important physiological functions, and in recent decades, considerable research has been conducted on the anti-mutation and anti-carcinogenic effects of ellagic acid and its inhibitory effect on the carcinogenesis induced by chemical substances. In vivo and in vitro experiments on tissue transplantation of mice and human bodies, ellagic acid shows obvious inhibition effect on chemical substance induced canceration and other multiple canceration, and especially has good inhibition effect on colon cancer, esophageal cancer, liver cancer, lung cancer, tongue and skin cancer and the like.
Ellagic acid has a molecular formula of C14H6O8The structural formula is shown in figure 1. The camellia oleifera shells contain a small amount of ellagic acid, water or alcohol is used for extraction and preparation of active ingredients in the camellia oleifera shells in the prior art, but no related prior art exists for extraction of ellagic acid in the camellia oleifera shells, and the camellia oleifera shells are mostly treated as waste materials at present, so that waste of raw materials is caused, and further research is needed for extraction of ellagic acid in the camellia oleifera shells.
Disclosure of Invention
The technical problem to be solved by the invention is to provide the method for extracting the ellagic acid from the oil tea fruit shell, which is simple to operate and high in extraction rate.
The technical scheme adopted by the invention for solving the technical problems is as follows: a method for extracting ellagic acid from oil tea fruit shells is characterized by comprising the following steps:
1) drying oil tea fruit shell in the sun, pulverizing and sieving for use;
2) adding an acid solution, stirring and extracting, and collecting the solution after reaction;
3) the collected solution is further purified to prepare ellagic acid.
In order to improve the extraction efficiency of ellagic acid, preferably, the acid solution in step 2) takes acid as a solute and water as a solvent, the acid is selected from one of hydrochloric acid, sulfuric acid, oxalic acid, acetic acid and citric acid, and the concentration of the acid is 0.01-2 mol/L.
Preferably, the acid is hydrochloric acid. After extraction, the flocculent precipitate of the organic acid system is easy to block seriously, and the cost of using the weak acid of the organic acid is obviously higher than that of hydrochloric acid and sulfuric acid, so the organic acid is not selected. Sulfuric acid is easy to agglomerate and carbonize with powder, which affects heat conduction and container life, so it is not selected either. Although there is no caking or floc precipitation in acetic acid, hydrochloric acid is clearly more effective than acetic acid, and therefore HCl is preferred as the hydrolysis acid in the present invention.
In order to further improve the extraction efficiency of ellagic acid, the concentration of the acid is preferably 0.5-1.0 mol/L.
In order to further improve the extraction efficiency of ellagic acid, preferably, the adding ratio of the oil tea fruit shell to the acid solution in the step 2) is 1 g: 3-100 mL.
In order to further improve the extraction efficiency of ellagic acid, preferably, the adding ratio of the oil tea fruit shell to the acid solution in the step 2) is 1 g: 20-50 mL.
In order to further improve the extraction efficiency of ellagic acid, the reaction time in the step 2) is preferably 0.1-3 h.
In order to further improve the extraction efficiency of ellagic acid, the reaction time in the step 2) is preferably 0.8-1.2 h.
In order to further improve the extraction efficiency of ellagic acid, the reaction temperature in the step 2) is preferably 20-100 ℃.
In order to further improve the extraction efficiency of ellagic acid, the reaction temperature in the step 2) is preferably 80-100 ℃.
Compared with the prior art, the invention has the advantages that: the camellia oleifera shells are mostly treated as waste materials at present, and are crushed and sieved, and then the acid solution is added for stirring and extraction, so that the method can greatly improve the extraction rate of ellagic acid in the camellia oleifera shells and improve the additional value of the camellia oleifera shells.
Drawings
FIG. 1 shows ellagic acid molecular formula.
FIG. 2 is a spectrum diagram of the detection of ellagic acid standard substance by high performance liquid chromatography; the peak area indicates the ellagic acid content.
FIG. 3 is a standard curve of the peak area and concentration of ellagic acid standard substance with different concentrations detected by high performance liquid chromatography.
FIG. 4 is a graph showing the extraction rate of ellagic acid by using hydrochloric acid of different concentrations in examples 10 to 14 of the present invention.
Fig. 5 is a graph of the extraction rate of ellagic acid from camellia oleifera shells and hydrochloric acid solution with different material-to-liquid ratios in examples 15 to 19 of the present invention.
FIG. 6 is a graph showing the extraction rate of ellagic acid from the same concentration of hydrochloric acid over different time periods according to examples 20 to 24 of the present invention.
Detailed Description
The invention is described in further detail below with reference to the accompanying examples.
Examples 1 to 24 are methods for extracting ellagic acid from oil tea fruit shells by the method of the present invention, and specific parameter settings and extraction rates are shown in table 2. Wherein:
in examples 10 to 14, the effect of different acid concentrations on the extraction amount of the target extract was examined by taking hydrochloric acid as an example and the hydrochloric acid concentrations were 0, 0.5, 1, 1.5 and 2mol/L, respectively, and as a result, as shown in FIG. 4, the ellagic acid extraction rate was between 0.69 and 2.63mg/g, and the extraction efficiency was better when the HCl concentration was 0.5 to 1.0 mol/L.
Examples 15 to 19 were carried out using hydrochloric acid as an example, and the feed-liquid ratios were 1:10, 1:20, 1:30, 1:40, and 1:50, respectively, to investigate the influence of the feed-liquid ratio on the extraction amount of the target extract; as shown in figure 5, the extraction rate is 2.28-3.41 mg/g, the material-liquid ratio (w/v) is 1 g: when the concentration is 20-50 mL, the ellagic acid extraction rate is good.
Examples 20 to 24 take hydrochloric acid as an example, the extraction time was 1, 2, 3, 4, 5h, and the effect of different times on the extraction amount of the objective extract was investigated. As shown in FIG. 6, the ellagic acid extraction rate was 1.72 to 2.75mg/g, and the best extraction effect was obtained after 1 hour.
Comparative example 50 (v/v)% ethanol aqueous solution was used, according to the material ratio 1: adding 5g of the powder into 100mL of 50% ethanol aqueous solution, performing ultrasonic extraction at 30 ℃ for 30min, performing vacuum filtration, diluting to a constant volume, and performing liquid phase measurement after passing through a 0.45-micron water film.
The material-liquid ratio in table 2 is the mass-to-volume ratio of the camellia oleifera shells to the acid solution/ethanol.
The detection method comprises the following steps: accurately weighing 5g of camellia oleifera pollen powder which is sieved by a 50-mesh sieve, collecting a solution after reaction, carrying out vacuum filtration, washing the container with a small amount of distilled water for multiple times, diluting with constant volume, and carrying out liquid phase measurement after passing through a 0.45-micron water film.
The HPLC chromatographic conditions are as follows: the present experiment was eluted using acetonitrile (a) and 1V% acetic acid (B) as mobile phases, thus setting the mobile phase conditions to: 0-5min, 10 v% A; 5-20min, 10% -25% A; 20-25min, 10% A, flow rate 1.0 mL/min.
The extraction rate (mg/g) is cr×V÷m
Wherein c isrAnd (3) measuring the concentration of ellagic acid and the volume of V constant volume, wherein m is the mass of the camellia oleifera abel.
As can be seen from Table 2, compared with the comparative example, the extraction rate of the ellagic acid is greatly improved, and the extraction rate of the ellagic acid can reach 3.39 mg/g.
Table 2 examples and comparative examples extraction parameter settings and test results
Claims (10)
1. A method for extracting ellagic acid from oil tea fruit shells is characterized by comprising the following steps:
1) drying oil tea fruit shell in the sun, pulverizing and sieving for use;
2) adding an acid solution, stirring and extracting, and collecting the solution after reaction;
3) the collected solution is further purified to prepare ellagic acid.
2. The method for extracting ellagic acid from a camellia oleifera shell according to claim 1, wherein: in the step 2), the acid solution takes acid as a solute and water as a solvent, the acid is selected from one of hydrochloric acid, sulfuric acid, oxalic acid, acetic acid and citric acid, and the concentration of the acid is 0.01-2 mol/L.
3. The method for extracting ellagic acid from a camellia oleifera shell according to claim 2, characterized in that: the acid is hydrochloric acid.
4. The method for extracting ellagic acid from a camellia oleifera shell according to claim 2, characterized in that: the concentration of the acid is 0.5-1.0 mol/L.
5. The method for extracting ellagic acid from a camellia oleifera shell according to claim 1, wherein: the adding ratio of the oil-tea camellia shells to the acid solution in the step 2) is 1 g: 3-100 mL.
6. The method for extracting ellagic acid from a camellia oleifera shell according to claim 5, wherein: the adding ratio of the oil-tea camellia shells to the acid solution in the step 2) is 1 g: 20-50 mL.
7. The method for extracting ellagic acid from a camellia oleifera shell according to claim 1, wherein: the reaction time in the step 2) is 0.1-3 h.
8. The method for extracting ellagic acid from a camellia oleifera shell according to claim 7, wherein: the reaction time in the step 2) is 0.8-1.2 h.
9. The method for extracting ellagic acid from a camellia oleifera shell according to claim 1, wherein: the reaction temperature in the step 2) is 20-100 ℃.
10. The method for extracting ellagic acid from a camellia oleifera shell according to claim 9, wherein: the reaction temperature in the step 2) is 80-100 ℃.
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| CN202011233554.8A CN112174977A (en) | 2020-11-06 | 2020-11-06 | Method for extracting ellagic acid from oil tea fruit shell |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114605428A (en) * | 2022-03-31 | 2022-06-10 | 广西壮族自治区林业科学研究院 | Method for extracting and purifying ellagic acid from camellia oleifera shells |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114605428A (en) * | 2022-03-31 | 2022-06-10 | 广西壮族自治区林业科学研究院 | Method for extracting and purifying ellagic acid from camellia oleifera shells |
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