CN104592185B - Method for extracting quercetin from eleocharis tuberosa peels - Google Patents
Method for extracting quercetin from eleocharis tuberosa peels Download PDFInfo
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- CN104592185B CN104592185B CN201410834869.6A CN201410834869A CN104592185B CN 104592185 B CN104592185 B CN 104592185B CN 201410834869 A CN201410834869 A CN 201410834869A CN 104592185 B CN104592185 B CN 104592185B
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- quercetin
- methyl alcohol
- under reduced
- concentrated under
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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 95
- 235000005875 quercetin Nutrition 0.000 title claims abstract description 49
- 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 46
- 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 45
- 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 45
- 229960001285 quercetin Drugs 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 22
- 244000103152 Eleocharis tuberosa Species 0.000 title abstract description 5
- 235000014309 Eleocharis tuberosa Nutrition 0.000 title abstract description 5
- 239000000284 extract Substances 0.000 claims abstract description 35
- 239000004952 Polyamide Substances 0.000 claims abstract description 23
- 229920002647 polyamide Polymers 0.000 claims abstract description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000499 gel Substances 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 138
- 239000012043 crude product Substances 0.000 claims description 35
- 235000003283 Pachira macrocarpa Nutrition 0.000 claims description 28
- 241001083492 Trapa Species 0.000 claims description 28
- 235000014364 Trapa natans Nutrition 0.000 claims description 28
- 235000009165 saligot Nutrition 0.000 claims description 28
- 239000003480 eluent Substances 0.000 claims description 24
- 238000004587 chromatography analysis Methods 0.000 claims description 20
- 238000001514 detection method Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 7
- 239000013505 freshwater Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- 238000012856 packing Methods 0.000 claims description 3
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 238000005227 gel permeation chromatography Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 6
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 6
- 238000007689 inspection Methods 0.000 description 6
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 6
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 6
- 235000005493 rutin Nutrition 0.000 description 6
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 6
- 229960004555 rutoside Drugs 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 206010062717 Increased upper airway secretion Diseases 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 2
- 208000026435 phlegm Diseases 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000722948 Apocynum cannabinum Species 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 1
- 240000008867 Capsella bursa-pastoris Species 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 1
- 241000332747 Dysosma versipellis Species 0.000 description 1
- 235000011201 Ginkgo Nutrition 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- GQODBWLKUWYOFX-UHFFFAOYSA-N Isorhamnetin Natural products C1=C(O)C(C)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 GQODBWLKUWYOFX-UHFFFAOYSA-N 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- YLWQTYZKYGNKPI-HMGRVEAOSA-N Quercetin 3'-glucoside Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=CC=C1O YLWQTYZKYGNKPI-HMGRVEAOSA-N 0.000 description 1
- 241000219784 Sophora Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 240000001085 Trapa natans Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 208000030303 breathing problems Diseases 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 235000008800 isorhamnetin Nutrition 0.000 description 1
- IZQSVPBOUDKVDZ-UHFFFAOYSA-N isorhamnetin Chemical compound C1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 IZQSVPBOUDKVDZ-UHFFFAOYSA-N 0.000 description 1
- 235000008777 kaempferol Nutrition 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- 206010036067 polydipsia Diseases 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
Abstract
The invention discloses a method for extracting quercetin from eleocharis tuberosa peels and belongs to the field of natural organic chemistry. The method is characterized by comprising the following steps of by using an acetone aqueous solution as a solvent, extracting quercetin from the eleocharis tuberosa peels, extracting an extract with ethyl acetate, separating an extractant with a middle-pressure MCI column chromatography and a polyamide column chromatography and purifying with Sephadex LH-20 gel and silica gel column chromatography to obtain a quercetin product of which the content of quercetin is not less than 95%. The method opens up a novel way for extracting and separating quercetin from natural plants, the good separation effect is achieved, the product is high in purify, the eleocharis tuberosa peels, which are always regarded as wastes, are changed into treasure, the selected chromatographic material MCI, polyamide and gel can be repeatedly used, the raw materials are easily available and are rich in resources, the method is low in production cost, the large-scale production can be performed and the method meets the needs of pharmaceutical industry.
Description
Technical field
The invention belongs to field of natural organic chemistry, it is related to a kind of extraction separation method of Quercetin, more particularly to one
Plant the method that separating meletin is extracted from water chestnut skin.
Background technology
Quercetin (Quercetin), chemistry entitled 3,5,7,3 ', 4 '-pentahydroxyflavone, also known as quercetin, Quercetin, be
Plant kingdom is distributed widest flavonoid drugs, is about distributed in 68% plant, be normally present in the flower of plant, leaf,
Among fruit.Contain substantial amounts of Quercetin in Chinese herbal medicine such as the sophora bud, red Dysosma versipellis, hyperici,herba, bluish dogbane leaf, ginkgo；Ocean in food
This composition is also enriched in green onion, grape, apple, red wine and green tea.Quercetin has good bioactivity, such as antitumor,
Anti-oxidant, anti-inflammatory, antiviral, antibacterial isoreactivity and eliminating the phlegm, cough-relieving, platelet aggregation-against, lowering blood pressure and blood fat, anti-tensile are coronal
Artery etc. is acted on, and clinically for treating chronic bronchitis, also has auxiliary therapeutic action to coronary heart disease and hyperpietic.
The main method of Quercetin is prepared for extraction method and rutin Hydrolyze method, is more commonly used with rutin Hydrolyze method.Publication number
For the Chinese invention patent of the A of CN 102382093 discloses a kind of production technology that Quercetin is prepared with rutin hydrolysis.The method
With rutin as raw material, through hydrolysis, filtering, washing and the operation such as refined obtain Quercetin, with simple production process, conversion ratio
Height, low production cost, the features such as product purity is high, but its raw material is rutin, it is necessary to be extracted from natural plants, is not easy to obtain
, and sour hydrolyzing rutin easily produces impurity such as Kaempferol and Isorhamnetin, two impurity are difficult by essence after forming aglycon
The method reduction content of system.
Water chestnut (Eleocharis tuberosa), also known as horseshoe, belongs to the ground of the perennial shallow water herbaceous plant water chestnut of Cyperaceae
Lower bulb, China's most area has cultivation.Wherein, Guangxi water chestnut yield accounts for the whole nation 70%, and He Prefecture water chestnut yield accounts for Guangxi
70%.According to the literature, water chestnut have antibacterial, it is antitumor, prevent and treat breathing problem, sharp intestines defaecation and diuresis row and the effect such as drench；Face
Can be used on bed treatment have sore throat, the disease such as phlegm-heat cough, pyreticosis polydipsia, difficult urination, dysentery.Research shows, the work of water chestnut
Property material is mainly enriched between pericarp and pulp.In water chestnut process, the water chestnut cortex amount being dropped accounts for fresh water chestnut
The 25% of shepherd's purse quality, resource is enriched very much.We have found under study for action, containing abundant Quercetin in water chestnut skin, but at present not
See the document report extracted from water chestnut skin and separate the compound.
The content of the invention
It is an object of the invention to：Propose a kind of method that water chestnut skin extracts Quercetin.
The method that water chestnut skin of the invention extracts Quercetin, extracts using traditional extraction method and chromatographic technique from water chestnut skin
Separating meletin, comprises the following steps that：
(1) fresh water chestnut skin is air-dried, is crushed, it is standby；By weight, 1 part of water chestnut skin powder is weighed, extractor is added
In, the 4-10 parts of aqueous acetone solution of 70% percent by volume is added every time, 24h is soaked at 25 DEG C, to soak 3 times, filtering merges
Filtrate, is concentrated under reduced pressure into paste, obtains extract.
(2) by weight, 1 part of extract is dispersed in 5 parts of water and is made suspension, with the 1-2 times of acetic acid second of water volume
Ester is extracted 3 times, combining extraction liquid, is concentrated under reduced pressure into dry, acquisition extract.
(3), to being completely dissolved, sample is mixed with the polyamide of 2-4 times of extract quality, by methyl alcohol toward addition methyl alcohol in extract
Dry, dress post is evaporated into, connection MCI posts carry out middle pressure and separate, and the methanol aqueous solution with 40-100% percents by volume is as mobile phase
Gradient elution, thin-layered chromatography detection, it is the eluent of 65-69% percentages to collect and combine flowing phase concentration, is concentrated under reduced pressure, and is obtained
Obtain crude product A.
(4), to being completely dissolved, sample is mixed with the polyamide of 2-4 times of quality toward addition methyl alcohol in crude product A, methyl alcohol is evaporated into
It is dry, it is transferred to polyamide chromatographic column and is separated, it is 3 with volume ratio:1-1:1 chloroform-methanol wash-out, thin-layered chromatography inspection
Survey, collect and combine the eluent containing Quercetin, be concentrated under reduced pressure, obtain crude product B.
(5) by weight, crude product B1 parts is dissolved in 4-8 parts of methyl alcohol, adds the water of equivalent methyl alcohol volume to be made suspension,
Purified with Sephadex LH-20 gel chromatographic columnses, eluted with methyl alcohol, thin-layered chromatography detection is collected and combined and contains Quercetin
Eluent, is concentrated under reduced pressure, and obtains crude product C.
(6) it is 9 with volume ratio by gained crude product C through silica gel chromatography:1-7:3 chloroform-acetone wash-out, collects
Merge the eluent containing Quercetin, be concentrated under reduced pressure, dry, obtain the Quercetin product that content is up to more than 95%.
2. method according to claim 1, it is characterised in that the described MCI post specifications in the step (3) are
70 × 460mm, packing material is MCI-gel CHP-20P, and column chromatography condition is：Post pressure is 80Psi, and flow rate of mobile phase is
50mL/min, Detection wavelength is 245nm；Described mobile phase is the methanol aqueous solution of 40-100% percents by volume.
3. method according to claim 1, it is characterised in that the polyamide described in the step (4), specification is
200-300 mesh；Eluent used is that volume ratio is 3:1-1:1 chloroform-methanol.
Its advantage is the present invention compared with prior art：Design science rationally, is opened and extracted from natural plants
The new way of separating meletin, good separating effect, product purity is high, the water chestnut skin for being always considered as discarded object is turned waste into wealth,
Selected chromatographic material MCI, polyamide and gel can Reusability, raw material is easy to get, aboundresources, and low production cost can
Large-scale production is carried out, medical industry needs are met.
Specific embodiment
With reference to embodiment, the invention will be further described, but embodiments of the present invention not limited to this.
The method that water chestnut skin of the invention extracts Quercetin, extracts using traditional extraction method and chromatographic technique from water chestnut skin
Separating meletin, comprises the following steps that：
(1) fresh water chestnut skin is air-dried, is crushed, it is standby.The water chestnut skin powder for weighing certain mass (g) adds extractor
In, the aqueous acetone solution of 70% percent by volume of 4-10 times of volume (mL) is added, 24h is soaked at 25 DEG C, soak 3 times,
Filtering, merging filtrate is concentrated under reduced pressure into paste, obtains extract.
(2) extract (g) is dispersed in 5 times of water of volume (mL) and is made suspension, with the 1-2 times of acetic acid second of water volume
Ester is extracted 3 times, combining extraction liquid, is concentrated under reduced pressure into dry, acquisition extract.
(3), to being completely dissolved, sample is mixed with the polyamide of 2-4 times of extract quality, by methyl alcohol toward addition methyl alcohol in extract
Dry, dress post is evaporated into, connection MCI posts carry out middle pressure and separate, and post specification is 70mm × 460mm, and packing material is Mitsubishi
The MCI-gel CHP-20P of company production, column chromatography condition is：Post pressure is 80Psi, and flow rate of mobile phase is 50mL/min, inspection
Survey wavelength is 254nm, is eluted by eluent gradient of the methanol aqueous solution of 40-100% percents by volume, according to the change of detection peak
Situation adjusts eluate concentration, is collected by every part of 500mL, thin-layered chromatography detection, and it is 65-69% to collect and combine flowing phase concentration
The eluent of percentage, is concentrated under reduced pressure, and obtains crude product A.
(4), to being completely dissolved, sample is mixed with the polyamide of 2-4 times of quality toward addition methyl alcohol in crude product A, methyl alcohol is evaporated into
It is dry, it is transferred to polyamide chromatographic column and is separated, it is 3 with volume ratio:1-1:1 chloroform-methanol wash-out, thin-layered chromatography inspection
Survey, collect and combine the eluent containing Quercetin, be concentrated under reduced pressure, obtain crude product B.
(5) crude product B (g) is dissolved in the methyl alcohol of 4-8 times of volume (mL), adds isometric water to be made suspension, with auspicious
The Sephadex LH-20 gel chromatographic columnses purifying of allusion quotation Amersham Pharmacia Biotech companies production, is washed with methyl alcohol
De-, thin-layered chromatography detection collects and combines the eluent containing Quercetin, is concentrated under reduced pressure, and obtains crude product C.
(6) it is 9 with volume ratio by gained crude product C through silica gel chromatography:1-7:3 chloroform-methanol wash-out, collects
Merge the eluent containing Quercetin, be concentrated under reduced pressure, dry, obtain the Quercetin product that content is up to more than 95%.
Embodiment 1
The fresh water chestnut skin powder of 8kg is added in extractor, the aqueous acetone solution of the percents by volume of 32L 70% is added,
24h is soaked at 25 DEG C, total immersion is steeped 3 times, filtering, merging filtrate, be concentrated under reduced pressure paste, obtains extract 1.05kg.
Turbid solution is made during extract is added into 5.0L water, is extracted 3 times with 5.0L ethyl acetate, combining extraction liquid, decompression
Concentration, obtains extract 120g.
The dissolving of 300mL methyl alcohol is added toward extract, sample is mixed with 260g polyamide, methyl alcohol is evaporated into dry, dress post, connection
MCI posts carry out middle pressure and separate, and the methanol aqueous solution with 40-100% percents by volume is eluent gradient wash-out, by every part
500mL is collected, thin-layered chromatography detection, and it is the eluent of 65-69% percentages to collect and combine flowing phase concentration, is concentrated under reduced pressure,
Obtain crude product A 9.8g.
Crude product A is dissolved in 20mL methyl alcohol, adds 20g polyamide to mix sample, methyl alcohol volatilization is dry, and being transferred to polyamide column is carried out
Separate, be 2 with volume ratio:1 chloroform-methanol wash-out, thin-layered chromatography detection collects and combines the wash-out containing Quercetin
Liquid, is concentrated under reduced pressure, and obtains crude product B 0.32g.
Crude product B is dissolved in the methyl alcohol of 1.0mL, adds 1.0mL water to be made suspension, with Sephadex LH-20 gel colors
Spectrum post purifying, is eluted with methyl alcohol, obtains crude product C 0.90mg.
It is 9 with volume ratio by gained crude product C through silica gel chromatography:1 chloroform-methanol wash-out, thin-layered chromatography inspection
Survey, collect and combine the eluent containing Quercetin, be concentrated under reduced pressure, dry, obtain the Quercetin product 35mg of content 97.0%.
Embodiment 2
The fresh water chestnut skin powder of 8kg is added in extractor, the aqueous acetone solution of the percents by volume of 32L 70% is added,
24h is soaked at 25 DEG C, total immersion is steeped 3 times, filtering, merging filtrate, be concentrated under reduced pressure paste, obtains extract 1.05kg.
Turbid solution is made during extract is added into 5.0L water, is extracted 3 times with 5.0L ethyl acetate, combining extraction liquid, decompression
Concentration, obtains extract 120g.
The dissolving of 300mL methyl alcohol is added toward extract, sample is mixed with 260g polyamide, methyl alcohol is evaporated into dry, dress post, connection
MCI posts carry out middle pressure and separate, and the methanol aqueous solution with 40-100% percents by volume is eluent gradient wash-out, by every part
500mL is collected, thin-layered chromatography detection, and it is the eluent of 65-69% percentages to collect and combine flowing phase concentration, is concentrated under reduced pressure,
Obtain crude product A 9.8g.
Crude product A is dissolved in 20mL methyl alcohol, adds 20g polyamide to mix sample, methyl alcohol volatilization is dry, and being transferred to polyamide column is carried out
Separate, be 3 with volume ratio:1 chloroform-methanol wash-out, thin-layered chromatography detection collects and combines the wash-out containing Quercetin
Liquid, is concentrated under reduced pressure, and obtains crude product B 0.27g.
Crude product B is dissolved in the methyl alcohol of 1.5mL, adds 1.5mL water to be made suspension, with Sephadex LH-20 gel colors
Spectrum post purifying, is eluted with methyl alcohol, obtains crude product C 55mg.
It is 9 with volume ratio by gained crude product C through silica gel chromatography:1 chloroform-methanol wash-out, thin-layered chromatography inspection
Survey, collect and combine the eluent containing Quercetin, be concentrated under reduced pressure, dry, obtain the Quercetin product 21mg that content is 95.3%.
Embodiment 3
The fresh water chestnut skin powder of 8kg is added in extractor, the aqueous acetone solution of the percents by volume of 32L 70% is added,
24h is soaked at 25 DEG C, total immersion is steeped 3 times, filtering, merging filtrate, be concentrated under reduced pressure paste, obtains extract 1.05kg.
Turbid solution is made during extract is added into 5.0L water, is extracted 3 times with 5.0L ethyl acetate, combining extraction liquid, decompression
Concentration, obtains extract 120g.
The dissolving of 300mL methyl alcohol is added toward extract, sample is mixed with 260g polyamide, methyl alcohol is evaporated into dry, dress post, connection
MCI posts carry out middle pressure and separate, and the methanol aqueous solution with 40-100% percents by volume is eluent gradient wash-out, by every part
500mL is collected, thin-layered chromatography detection, and it is the eluent of 65-69% percentages to collect and combine flowing phase concentration, is concentrated under reduced pressure,
Obtain crude product A 9.8g.
Crude product A is dissolved in 20mL methyl alcohol, adds 20g polyamide to mix sample, methyl alcohol volatilization is dry, and being transferred to polyamide column is carried out
Separate, be 1 with volume ratio:1 chloroform-methanol wash-out, thin-layered chromatography detection collects and combines the wash-out containing Quercetin
Liquid, is concentrated under reduced pressure, and obtains crude product B 0.48g.
Crude product B is dissolved in the methyl alcohol of 1.0mL, adds 1.0mL water to be made suspension, with Sephadex LH-20 gel colors
Spectrum post purifying, is eluted with methyl alcohol, obtains crude product C 0.95mg.
It is 8 with volume ratio by gained crude product C through silica gel chromatography:2 chloroform-methanol wash-out, thin-layered chromatography inspection
Survey, collect and combine the eluent containing Quercetin, be concentrated under reduced pressure, dry, obtain the Quercetin product 25mg of content 96.3%.
Products obtained therefrom is passed through1H-NMR、13C-NMR and ESIMS chromatograms confirm structure.Spectral data is confirmed, separated to purify
The product for arriving is Quercetin, and its chemical structural formula is as follows：
Quercetin, yellow needle-like crystals.1H NMR(400MHz,methanol-d4)δ:6.16(s,H-6),6.37(s,H-
8), 7.73 (s, H-2 '), 6.87 (d, J=8.3Hz, H-5 '), 7.62 (d, J=7.8Hz, H-6 ')；13C NMR(125MHz,
methanol-d4)δ:147.9(s,C-2),137.3(s,C-3),177.3(s,C-4),162.5(s C-5),99.4(s,C-
6),165.7(s,C-7),94.6(d,C-8),158.2(s,C-9),104.5(s,C-10),124.1(s,C-1′),116.1(d,
C-2′),146.3(s,C-3′),148.8(s,C-4′),116.4(d,C-5′),121.7(d,C-6′)；ESIMS(negative-
ion mode)m/z 301[M-H]-。
Claims (3)
1. a kind of method that water chestnut skin extracts Quercetin, it is comprised the following steps that：
(1) fresh water chestnut skin is air-dried, is crushed, it is standby；By weight, 1 part of water chestnut skin powder is weighed, in addition extractor,
The 4-10 parts of aqueous acetone solution of 70% percent by volume being added every time, 24h being soaked at 25 DEG C, soaked 3 times, filtering merges filter
Liquid, is concentrated under reduced pressure into paste, obtains extract；
(2) by weight, 1 part of extract is dispersed in 5 parts of water and is made suspension, extracted with the 1-2 times of ethyl acetate of water volume
Take 3 times, combining extraction liquid, be concentrated under reduced pressure into dry, acquisition extract；
(3), to being completely dissolved, sample is mixed with the polyamide of 2-4 times of extract quality toward addition methyl alcohol in extract, methyl alcohol is volatilized
To dry, post is filled, connection MCI posts carry out middle pressure and separate, and the methanol aqueous solution with 40-100% percents by volume is as eluent gradient
Wash-out, thin-layered chromatography detection, it is the eluent of 65-69% percentages to collect and combine flowing phase concentration, is concentrated under reduced pressure, and obtains thick
Product A；
(4) toward adding in crude product A methyl alcohol to being completely dissolved, sample is mixed with the polyamide of 2-4 times of quality, methyl alcohol is evaporated into dry, turned
Enter polyamide chromatographic column to be separated, be 3 with volume ratio:1-1:1 chloroform-methanol wash-out, thin-layered chromatography detection is received
Collection merges the eluent containing Quercetin, is concentrated under reduced pressure, and obtains crude product B；
(5) by weight, 1 part of crude product B is dissolved in 4-8 parts of methyl alcohol, adds the water of equivalent methyl alcohol volume to be made suspension, used
Sephadex LH-20 gel chromatographic columnses are purified, and are eluted with methyl alcohol, thin-layered chromatography detection, collect and combine washing containing Quercetin
De- liquid, is concentrated under reduced pressure, and obtains crude product C；
(6) it is 9 with volume ratio by gained crude product C through silica gel chromatography:1-7:3 chloroform-acetone wash-out, collects and combines
Eluent containing Quercetin, is concentrated under reduced pressure, and dries, and obtains the Quercetin product that content is up to more than 95%.
2. method according to claim 1, it is characterised in that described MCI posts specification in the step (3) for 70 ×
460mm, packing material is MCI-gel CHP-20P, and column chromatography condition is：Post pressure is 80Psi, and flow rate of mobile phase is 50mL/
Min, Detection wavelength is 245nm；Described mobile phase is the methanol aqueous solution of 40-100% percents by volume.
3. method according to claim 1, it is characterised in that the polyamide described in the step (4), specification is 200-
300 mesh；Eluent used is that volume ratio is 3:1-1:1 chloroform-methanol.
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| CN108440477B (en) * | 2018-04-23 | 2019-11-29 | 江苏耐雀生物工程技术有限公司 | A method of preparing Quercetin from tungoiltree juvenile leaf |
| CN115947709A (en) * | 2022-12-29 | 2023-04-11 | 陕西嘉禾药业有限公司 | Method for preparing quercetin from onion skin |
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| AU2005203232A1 (en) * | 2005-07-21 | 2007-02-08 | Bioequal Ag | Topical formulations for the treatment of papillary tubercles, nail diseases and nail care |
| CN101269161A (en) * | 2008-05-20 | 2008-09-24 | 贺州学院 | Technique for extracting total flavone from eleocharis dulcis trin.ex henschel husk |
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| AU2005203232A1 (en) * | 2005-07-21 | 2007-02-08 | Bioequal Ag | Topical formulations for the treatment of papillary tubercles, nail diseases and nail care |
| CN101269161A (en) * | 2008-05-20 | 2008-09-24 | 贺州学院 | Technique for extracting total flavone from eleocharis dulcis trin.ex henschel husk |
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Application publication date: 20150506 Assignee: Guangxi Hengfengda Supply Chain Management Co.,Ltd. Assignor: HEZHOU University Contract record no.: X2023980046610 Denomination of invention: Method for Extracting Quercetin from Water Chestnut Peel Granted publication date: 20170524 License type: Common License Record date: 20231108 Application publication date: 20150506 Assignee: Pingle Leyao Food Co.,Ltd. Assignor: HEZHOU University Contract record no.: X2023980046448 Denomination of invention: Method for Extracting Quercetin from Water Chestnut Peel Granted publication date: 20170524 License type: Common License Record date: 20231108 |
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