CN109777843B - Method for preparing quinic acid - Google Patents
Method for preparing quinic acid Download PDFInfo
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- CN109777843B CN109777843B CN201910172792.3A CN201910172792A CN109777843B CN 109777843 B CN109777843 B CN 109777843B CN 201910172792 A CN201910172792 A CN 201910172792A CN 109777843 B CN109777843 B CN 109777843B
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- ethanol
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- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 title claims abstract description 35
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 title claims abstract description 35
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000000605 extraction Methods 0.000 claims abstract description 24
- 239000002994 raw material Substances 0.000 claims abstract description 23
- 239000011347 resin Substances 0.000 claims abstract description 20
- 229920005989 resin Polymers 0.000 claims abstract description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000004793 Polystyrene Substances 0.000 claims abstract description 16
- 229920002223 polystyrene Polymers 0.000 claims abstract description 16
- 239000002798 polar solvent Substances 0.000 claims abstract description 14
- 108010038851 tannase Proteins 0.000 claims abstract description 14
- 238000001179 sorption measurement Methods 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000004440 column chromatography Methods 0.000 claims abstract description 9
- 239000003480 eluent Substances 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 239000003463 adsorbent Substances 0.000 claims description 4
- 238000002137 ultrasound extraction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000005648 plant growth regulator Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 5
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- -1 alicyclic organic acid Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 241001552454 Castanopsis tibetana Species 0.000 description 1
- 241000219428 Fagaceae Species 0.000 description 1
- 241000592342 Tracheophyta Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000010204 pine bark Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a novel method for preparing quinic acid, which is specifically characterized in that a hook cone is used as a raw material, a polar solvent is used as a solvent for extraction, the extraction is carried out through tannase enzymolysis, and finally, the quinic acid is obtained through polystyrene type macroporous adsorption resin column chromatography; wherein the polar solvent is a composition of water and one or more than two of methanol, ethanol and acetone, and the proportion of the water is more than or equal to 20 v/v%; the polystyrene macroporous adsorption resin is D101, Diaion HP-20 or AB-8; the eluent used in the chromatography is a composition of water and one or more than two of methanol, ethanol and acetone, and the proportion of the water is more than or equal to 20 v/v%. The invention firstly takes the uncinate leaf as the raw material, and obtains the quinic acid with stable quality, high yield and high purity through extraction, tannase hydrolysis and column chromatography, thereby not only providing a new supply raw material for the preparation of the quinic acid, but also opening up a new utilization way for the uncinate.
Description
Technical Field
The invention relates to a preparation method of quinic acid, in particular to a novel method for preparing quinic acid.
Background
Quinic acid is an alicyclic organic acid which is specific to higher plants, is a precursor substance for aromatic amino acid biosynthesis, is commonly present in vascular plants, and often coexists with shikimic acid in the plant body. Quinic acid has a special structure, has a plurality of chiral centers, is an important material in stereo organic synthesis, is widely applied to the aspects of synthesizing natural products and preparing new polymeric materials and the like as chiral raw materials, and has a specific structure shown as the following formula:
hook awl (Castanopsis tibetana Hance) Is a plant of coniferous, Fagaceae, with thick bark, such as pine bark, and light reddish brown and smooth endothelium. The ring-hole wood has only fine wood rays in the xylem, has clear heartwood and border wood, reddish brown heartwood, lighter border wood color, clear annual rings, firm and heavy material and is resistant to water and moisture, is suitable for being used as pit wood, beams, columns, buildings and furniture, belongs to cones, and is a common main material tree species in the south of the Yangtze river. Ramulus Uncariae cum uncis fruit (ramulus Uncariae cum uncis) can be used for treating dysentery. To date, no report has been found concerning the isolation of quinic acid from the cone of uncinate.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a novel method for preparing quinic acid, which is characterized in that the quinic acid with stable quality, high yield and high purity is obtained by taking the uncinate as a raw material for the first time and performing simple and convenient processes such as extraction, tannase hydrolysis, column chromatography and the like, so that a novel supply raw material is provided for the preparation of the quinic acid, and a novel utilization way is opened up for the uncinate.
The novel method for preparing quinic acid is characterized in that the method comprises the steps of taking a hook cone as a raw material, taking a polar solvent as a solvent for extraction, recovering the solvent from an extracting solution, carrying out enzymolysis on the obtained residual liquid by using tannase, and carrying out polystyrene type macroporous adsorption resin column chromatography on an enzymolysis liquid to obtain the quinic acid; wherein,
the polar solvent is a composition of water and one or more than two of methanol, ethanol and acetone, wherein the proportion of the water in the polar solvent is more than or equal to 20 v/v%;
the polystyrene macroporous adsorption resin is D101, Diaion HP-20 or AB-8;
when the enzymolysis liquid is subjected to polystyrene macroporous adsorption resin column chromatography, the used eluent is a composition of water and one or more than two of methanol, ethanol and acetone, wherein the proportion of the water in the eluent is more than or equal to 20 v/v%.
In the technical scheme of the invention, the model of the polystyrene macroporous adsorption resin has very important influence on the yield and purity of the obtained product, and the test of the applicant shows that the high yield (2.5-3.2%) and the high purity (more than 93% by HPLC analysis method) can be obtained only when the polystyrene macroporous adsorption resin with the model of D101, Diaion HP-20 or AB-8 is selected.
In the technical scheme of the invention, leaves and/or branches and/or barks of the cone can be used as raw materials, and the raw materials are preferably cut or crushed and then extracted.
In the technical scheme of the invention, the extraction is heating extraction, ultrasonic extraction or normal temperature extraction, and the times of extraction, the addition amount of a solvent in each extraction, the extraction time and the like can refer to the conventional technology. Preferably, reflux extraction is adopted, and specifically, the extraction temperature is in the range of 40 ℃ to the reflux temperature of the solvent, and preferably in the range of 50 ℃ to the reflux temperature of the solvent; the extraction times are 2-4 times, preferably 3 times; the adding amount of the solvent in each extraction is 3-12 times of the weight of the raw materials, and preferably 6-10 times; the time for each extraction is 2-3 h, preferably 2.5 h.
In the technical scheme of the invention, the dosage of the tannase can be 0.2-1.0 per mill of the weight of the raw materials, and preferably 0.5 per mill. The enzymolysis is usually carried out at the temperature of less than or equal to 35 ℃, and the enzymolysis time is 1-4 h. The enzymolysis is preferably carried out at the temperature of 20-30 ℃, and the enzymolysis time is preferably 2-4 h.
In the technical scheme, in the composition of the polar solvent, the proportion of water is preferably 20-50 v/v%; in the composition of the eluent, the proportion of water is preferably 20-50 v/v%.
When the enzymolysis liquid is subjected to polystyrene macroporous adsorption resin column chromatography, the column is washed by water until the effluent liquid is colorless, then the column is eluted by an eluant, the combined fractions are detected by thin layer chromatography in the elution process, the target fractions are collected, the solvent is recovered, and then the quinic acid is obtained after drying.
Compared with the prior art, the method provided by the invention has the advantages that the method takes the uncinate leaves as the raw material for the first time, and the quinic acid with stable quality, high yield (2.5-3.3%) and high purity (more than 93%, HPLC analysis method) is obtained through simple and convenient processes such as extraction, tannase hydrolysis and column chromatography, so that a new supply raw material is provided for the preparation of the quinic acid, and a new utilization way is opened up for the uncinate.
Detailed Description
The present invention will be better understood from the following detailed description of specific examples, which should not be construed as limiting the scope of the present invention.
Example 1
Taking 1.0kg of fresh leaf raw material of the uncinate cone, cutting, adding ethanol/water solution (wherein the ethanol accounts for 60 v/v%) which is 8 times of the weight of the raw material, extracting for 2.5 hours at 50 ℃, and filtering; adding 8 times of ethanol/water solution (wherein ethanol accounts for 60 v/v%) of the weight of the raw materials into the filter residue, extracting at 50 ℃ for 2.5 hours under the condition of heat preservation, and filtering; adding 8 times of ethanol/water solution (wherein ethanol accounts for 60 v/v%) into the residue, extracting at 50 deg.C for 2.5 hr, filtering, mixing the filtrates, recovering ethanol, filtering to remove residual insoluble substances, and collecting the filtrate; cooling the filtrate to 25 ℃, adding 0.5g of tannase for hydrolysis for 3 hours, filtering, adsorbing the filtrate by polystyrene type macroporous adsorption resin (D101), eluting by using deionized water with 3 times of column volume, then using ethanol/water solution with 4 times of column volume (wherein ethanol accounts for 30 v/v%), determining the merged fluid by thin layer chromatography, concentrating the merged fluid under reduced pressure to obtain an extract, and drying the extract to obtain 30.1g of white solid (with the content of 96.3%).
The resulting white solid was subjected to structural identification (by MS, Mass Spectrometry, etc.),1H-NMR and13C-NMR etc.) and comparing the results with literature reported values.
LCIT-TOF-MS: m/z 191.0756 (M-H) (calcd for C7H12O6, 192.0634)。
1H-NMR(500 MHz, acetone-d 6) δ: 2.14-2.28 (4H, m, H-2a, H-2b, H-6a, H-6b), 3.68 (1H, dd, J=2.9, 8.3 Hz, H-4), 4.16 (1H, m, H-3), 4.24 (1H, m, H-5)。
13C-NMR(125 MHz, acetone-d 6) δ: 37.1 (C-2)，39.9 (C-6)，68.3 (C-5)，71.3 (C-4)，71.0 (C-3)，75.4 (C-1)，167.6 (C-7)。
The MS mentioned above,1H-NMR and13the C-NMR data are basically consistent with the reports in the literature, so that the quinic acid is identified, and the structure is as follows:
and (4) purity checking: HPLC analysis method [ column: cosmosil 5C18AR II (4.6250 mm, 5 μm); column temperature: 35 ℃; mobile phase: CH (CH)3CN-50 mM H3PO40-39 min 4-30% CH3CN; flow rate: 0.8 mL/min; detection wavelength: 209nm]The purity of the white solid obtained in the example was measured, and the result showed that the purity of the obtained white solid quinic acid was 96.3%.
Comparative example 1
Example 1 was repeated except that the D101 macroporous resin was replaced by a D102 macroporous resin. 20.3g of a white solid was finally obtained.
The white solid obtained in this comparative example was subjected to the same MS and,1H-NMR and13and identifying the quinic acid by C-NMR and other spectroscopic data.
The white solid obtained in this comparative example was checked for purity by the same method as in example 1, and the purity was found to be 87.7%.
Comparative example 2
Example 1 was repeated except that ADS-8 macroporous resin was used in place of the D101 macroporous resin. Finally, 24.6g of a white solid was obtained.
The white solid obtained in this comparative example was subjected to the same MS and,1H-NMR and13and identifying the quinic acid by C-NMR and other spectroscopic data.
The white solid obtained in this comparative example was checked for purity by the same method as in example 1, and the purity was determined to be 86.2%.
Example 2
Example 1 was repeated except that:
1) the polar solvent used for extraction was an ethanol/water solution (where ethanol accounts for 80 v/v%);
2) the adding amount of the tannase is 0.6 g;
3) the polystyrene macroporous adsorbent resin used is Diaion HP-20.
Finally, 33.3g of quinic acid (purity 94.8%) is obtained.
Example 3
Example 1 was repeated except that:
1) the raw material is crushed bark of the uncinate cone, and the polar solvent for extraction is methanol/water solution (wherein the methanol accounts for 60 v/v%);
2) the adding amount of the tannase is 1.0 g;
3) the polystyrene macroporous adsorbent resin is AB-8.
Finally, 34.1g of quinic acid (purity 93.4%) is obtained.
Example 4
Example 1 was repeated except that:
1) the raw material is crushed ramulus Uncariae cum uncis, and the polar solvent for extraction is acetone/water solution (wherein acetone accounts for 50 v/v%);
2) the adding amount of the tannase is 0.6g, and the enzymolysis is carried out at 35 ℃ for 2 hours;
3) in elution, 30 v/v% ethanol was replaced by 50 v/v% aqueous acetone.
Finally, 29.8g of quinic acid (purity 96.6%) is obtained.
Example 5
Example 1 was repeated except that:
1) the polar solvent used for extraction was methanol/water solution (methanol accounts for 70 v/v%);
2) the adding amount of the tannase is 0.2g, and the enzymolysis is carried out at the temperature of 20 ℃ for 4 hours;
3) the polystyrene macroporous adsorbent resin used was Diaion HP-20, and during elution, 30 v/v% ethanol was replaced with 70 v/v% aqueous methanol.
Finally, 32.6g of quinic acid (purity 95.0%) is obtained.
Example 6
Taking 1.0kg of fresh leaf raw material of the uncinate cone, cutting, adding ethanol/water solution (wherein the ethanol accounts for 30 v/v%) which is 10 times of the weight of the raw material, performing ultrasonic extraction at room temperature for 1 hour (the power is 250W, the ultrasonic frequency is 40kHz), and filtering; adding 5 times of ethanol/water solution (wherein ethanol accounts for 30 v/v%) into the residue, ultrasonic extracting at room temperature for 1 hr (power is 250W, ultrasonic frequency is 40kHz), filtering, mixing the filtrates for 2 times to obtain extractive solution, recovering ethanol from the extractive solution, filtering to remove residual insoluble substances, and collecting filtrate; cooling the filtrate to 30 ℃, adding 0.5g of tannase for hydrolysis for 3 hours, filtering, adsorbing the filtrate with polystyrene type macroporous adsorption resin (Diaion HP-20), eluting with 3 times of column volume of deionized water, then with 4 times of column volume of ethanol/water solution (wherein ethanol accounts for 30 v/v%), taking 0.2 times of column volume as one fraction, determining the combined fraction by thin layer chromatography, concentrating the combined solution at 50 ℃ below reduced pressure to obtain an extract, and drying the extract to obtain 31.1g of quinic acid compound (purity 95.6%).
Although the embodiments of the present invention have been described in detail, it should be understood that various changes, modifications, substitutions and the like can be made without departing from the spirit and principle of the present invention.
Claims (7)
1. A process for preparing quinic acid, which is characterized by: extracting with hook cone as raw material and polar solvent as solvent, recovering solvent from the extractive solution, performing enzymolysis on the obtained residue with tannase, and subjecting the enzymolysis solution to polystyrene macroporous adsorbent resin column chromatography to obtain the final product; wherein,
the polar solvent is a composition of water and one or more than two of methanol, ethanol and acetone, wherein the proportion of the water in the polar solvent is more than or equal to 20 v/v%;
the polystyrene macroporous adsorption resin is D101, Diaion HP-20 or AB-8;
when the enzymolysis liquid is subjected to polystyrene macroporous adsorption resin column chromatography, the used eluent is a composition of water and one or more than two of methanol, ethanol and acetone, wherein the proportion of the water in the eluent is more than or equal to 20 v/v%.
2. The process for the preparation of quinic acid, according to claim 1, wherein: the extraction is heating extraction, ultrasonic extraction or normal temperature extraction.
3. The process for the preparation of quinic acid, according to claim 1, wherein: the dosage of the tannase is 0.2-1.0 per mill of the weight of the raw materials.
4. The process for the preparation of quinic acid, according to claim 1, wherein: the enzymolysis is carried out at the temperature of less than or equal to 35 ℃, and the enzymolysis time is 1-4 h.
5. The process for the preparation of quinic acid, according to any one of claims 1 to 4, wherein: in particular to a method for preparing the plant growth regulator by using leaves and/or branches and/or barks of the hook cones as raw materials.
6. The process for the preparation of quinic acid, according to any one of claims 1 to 4, wherein: in the composition of the polar solvent, the proportion of water is 20-50 v/v%.
7. The process for the preparation of quinic acid, according to any one of claims 1 to 4, wherein: in the composition of the eluent, the proportion of water is 20-50 v/v%.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000086575A (en) * | 1998-09-16 | 2000-03-28 | Mitsui Chemicals Inc | Production of quinic acid and quinic ester |
| CN101343225A (en) * | 2008-08-26 | 2009-01-14 | 施树云 | Preparation method for high-purity di-coffee mesitoyl quinine acid compounds |
| WO2011071056A1 (en) * | 2009-12-09 | 2011-06-16 | 花王株式会社 | Method for producing purified tea extract |
| JP2012183079A (en) * | 2012-07-03 | 2012-09-27 | Kao Corp | Method for producing non-polymer catechin-containing purified green tea extract |
| CN102766140A (en) * | 2012-08-14 | 2012-11-07 | 玉溪市维和生物技术有限责任公司 | Process for separating and preparing quinine sulfate from peruvian bark |
-
2019
- 2019-03-07 CN CN201910172792.3A patent/CN109777843B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000086575A (en) * | 1998-09-16 | 2000-03-28 | Mitsui Chemicals Inc | Production of quinic acid and quinic ester |
| CN101343225A (en) * | 2008-08-26 | 2009-01-14 | 施树云 | Preparation method for high-purity di-coffee mesitoyl quinine acid compounds |
| WO2011071056A1 (en) * | 2009-12-09 | 2011-06-16 | 花王株式会社 | Method for producing purified tea extract |
| JP2012183079A (en) * | 2012-07-03 | 2012-09-27 | Kao Corp | Method for producing non-polymer catechin-containing purified green tea extract |
| CN102766140A (en) * | 2012-08-14 | 2012-11-07 | 玉溪市维和生物技术有限责任公司 | Process for separating and preparing quinine sulfate from peruvian bark |
Non-Patent Citations (4)
| Title |
|---|
| Anti-aging potential of extracts from Sclerocarya birrea (A. Rich.) Hochst and its chemical profiling by UPLC-Q-TOF-MS;Tinotenda Shoko等;《BMC Complementary and Alternative Medicine》;20180207;第1-14页 * |
| Three new compounds from the leaves of Castanopsis tibetana Hance;Ya-Feng Wang等;《Natural Product Research》;20210424;第1-5页 * |
| 钩锥化学成分研究(Ⅰ);王亚凤等;《中药材》;20190831;第42卷(第8期);第1789-1792页 * |
| 青霉高单宁酶活性菌株选育及酶法转化没食子酸及奎尼酸研究;刘小兰;《万方学位论文数据库》;20070807;全文 * |
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