CN104529977B - Corm Eleocharitis skin extracts the method for luteolin - Google Patents
Corm Eleocharitis skin extracts the method for luteolin Download PDFInfo
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- CN104529977B CN104529977B CN201410833075.8A CN201410833075A CN104529977B CN 104529977 B CN104529977 B CN 104529977B CN 201410833075 A CN201410833075 A CN 201410833075A CN 104529977 B CN104529977 B CN 104529977B
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- luteolin
- methanol
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- corm eleocharitis
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- 239000000284 extract Substances 0.000 title claims abstract description 61
- 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 60
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 title claims abstract description 60
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 235000009498 luteolin Nutrition 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 105
- 238000000605 extraction Methods 0.000 claims abstract description 22
- 239000011347 resin Substances 0.000 claims abstract description 20
- 229920005989 resin Polymers 0.000 claims abstract description 20
- 239000007864 aqueous solution Substances 0.000 claims abstract description 17
- 239000000243 solution Substances 0.000 claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 12
- 239000000047 product Substances 0.000 claims abstract description 11
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000003463 adsorbent Substances 0.000 claims abstract description 3
- 239000002024 ethyl acetate extract Substances 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 13
- 238000004809 thin layer chromatography Methods 0.000 claims description 13
- 239000003480 eluent Substances 0.000 claims description 12
- 238000001179 sorption measurement Methods 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 229930182470 glycoside Natural products 0.000 claims description 7
- 150000002338 glycosides Chemical class 0.000 claims description 7
- 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 description 7
- 238000001291 vacuum drying Methods 0.000 claims description 7
- 238000010936 aqueous wash Methods 0.000 claims description 3
- 238000005202 decontamination Methods 0.000 claims description 3
- 230000003588 decontaminative effect Effects 0.000 claims description 3
- 230000028161 membrane depolarization Effects 0.000 claims description 3
- 241001128140 Reseda Species 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 abstract description 8
- 238000005227 gel permeation chromatography Methods 0.000 abstract description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- 241000196324 Embryophyta Species 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
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- 235000005853 Cyperus esculentus Nutrition 0.000 abstract 1
- 241000103725 Cyperus esculentus var. esculentus Species 0.000 abstract 1
- 239000010903 husk Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 230000003068 static effect Effects 0.000 description 5
- -1 flavonoid Compound Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
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- 239000011265 semifinished product Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 2
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 2
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 2
- 240000008867 Capsella bursa-pastoris Species 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- 241000628997 Flos Species 0.000 description 2
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 description 2
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 description 2
- 229940025878 hesperidin Drugs 0.000 description 2
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 description 2
- 210000000582 semen Anatomy 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 241000404844 Callicarpa nudiflora Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 244000103152 Eleocharis tuberosa Species 0.000 description 1
- 235000014309 Eleocharis tuberosa Nutrition 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 235000003283 Pachira macrocarpa Nutrition 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- 241000282806 Rhinoceros Species 0.000 description 1
- 241000207929 Scutellaria Species 0.000 description 1
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 description 1
- 206010043458 Thirst Diseases 0.000 description 1
- 240000001085 Trapa natans Species 0.000 description 1
- 235000014364 Trapa natans Nutrition 0.000 description 1
- 240000000377 Tussilago farfara Species 0.000 description 1
- 235000004869 Tussilago farfara Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000012407 engineering method Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 description 1
- AIONOLUJZLIMTK-UHFFFAOYSA-N hesperetin Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-UHFFFAOYSA-N 0.000 description 1
- 229960001587 hesperetin Drugs 0.000 description 1
- 235000010209 hesperetin Nutrition 0.000 description 1
- FTODBIPDTXRIGS-UHFFFAOYSA-N homoeriodictyol Natural products C1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 FTODBIPDTXRIGS-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229920000344 molecularly imprinted polymer Polymers 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000009165 saligot Nutrition 0.000 description 1
- 229940091258 selenium supplement Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The Corm Eleocharitis skin of the present invention extracts the method for luteolin, belong to field of natural organic chemistry, it is characterized in that, with any one in methanol aqueous solution, ethanol water or aqueous acetone solution as solvent, luteolin in extraction of chufa husk, extract separates with macroporous adsorbent resin after ethyl acetate extracts, and gained crude product gel chromatography column purification obtains content luteolin product more than 95%.The present invention opens and extracts the new way separating luteolin from natural plants; good separating effect; product purity is high, makes the Corm Eleocharitis skin being always considered garbage turn waste into wealth, and selected macroporous resin and gel all can Reusabilities; raw material is easy to get; aboundresources, production cost is low, has preferable application prospect; large-scale production can be carried out, meet medical industry needs.
Description
Technical field
The invention belongs to field of natural organic chemistry, relate to the extraction separation method of a kind of luteolin, particularly
Relate to a kind of method extracted from Corm Eleocharitis skin and separate luteolin.
Background technology
Luteolin (Luteolin), chemistry entitled 5,7,3 ', 4 '-kaempferol, is a kind of natural flavonoid
Compound, has multiple pharmacologically active, such as antioxidation, antibacterial, antitumor, antiviral, antiinflammatory, antiallergic etc.
Biological activity and vasodilator, antifertility act on hormone, immunomodulating etc., and clinic is mainly used in cough-relieving, dispels
The diseases such as expectorant, antiinflammatory, blood fat reducing and treatment cardiovascular disease, SARS, hepatitis.Have in the market multiple with
Luteolin is the product of main component, such as Radix Lamiophlomidis Rotatae capsule, MAISHU Capsules and frondosa oral liquid in late autumn etc..
Luteolin is widely distributed in nature, is primarily present in Flos Lonicerae, Flos Chrysanthemi, Herba Schizonepetae, Bai Maoxia withered
In the crude drugs such as grass, arithoke, Perilla, Scutellaria, Callicarpa nudiflora and selenium supplement, cabbage, cauliflower,
In the vegetables such as Radix Betae, Broccoli, Radix Dauci Sativae, Herba Apii graveolentis, Fructus Capsici, Fructus Capsici and Semen arachidis hypogaeae.Luteolin can be from reseda
With isolated in other various plants, it is possible to be directly synthesized or semi-synthetic obtain.
The Chinese patent of Publication No. CN 101712669A discloses one and utilizes molecular engineering method to extract separation
The method of luteolin.This method prepares the material of molecularly imprinted polymer with luteolin for masterplate, and with this point
The luteolin in Pericarppium arachidis hypogaeae extracting solution from purification, it is thus achieved that luteolin sterling.It is characterized in separating material
Having the strongest specific aim, but make complexity, cost is high, is unfavorable for large-scale production.Publication No. CN
The Introduction To Cn Patent of 102040579A utilizes the method that Roots of Peanut, stem, leaf, shell extract luteolin.
The method 70% ethanol extraction, Reusability macroporous resin adsorption separates, and refines finally by recrystallization method
Obtain luteolin.Its feature is that the plant resources using low cost sustainable use is raw material, uses environmental protection
Ethanol carry out extracting and eluting.At present, luteolin is mainly with medical materials such as Radix Lamiophlomidis Rotatae, Semen arachidis hypogaeae, little spring flowers
For raw material, it is Extraction solvent with methanol or ethanol, reflux, extract, obtain with purification with macroreticular resin, exist
Raw material is few, source is unstable, high in cost of production shortcoming.
The Chinese patent of Publication No. CN 1666987A discloses a kind of method synthesizing luteolin, the party
Method is with phloroglucinol as initiation material, it is not necessary to protection, and directly with 3,4-dimethyl phenacyl ethyl acetate is condensed,
Cyclization, obtains luteolin through aluminum chloride/pyridine catalysis demethylation, and total recovery is 34.2%.Publication No.
A kind of Hesperidin of the Introduction To Cn Patent of CN 103145668A prepares the new technique of luteolin, the method
Obtaining hesperetin first with Hesperidin hydrolysis, then prepare Herba Pelargonii Graveolentis grass element through dehydrogenase/reductase, last demethylation obtains
Obtain luteolin.It is directly synthesized luteolin and easily entrains impurity, and the raw material used by semi-synthetic luteolin is also
It is difficult to obtain.
Corm Eleocharitis (Eleocharis tuberosa), also known as Horse hoof, belongs to Cyperaceae perennial shallow water herbaceous plant Corm Eleocharitis
Underground bulb, China's most area has cultivation.Wherein, Guangxi Corm Eleocharitis yield accounts for the whole nation 70%, He Prefecture water chestnut
Shepherd's purse yield accounts for Guangxi 70%.According to the literature, Corm Eleocharitis has antibacterial, antitumor, prevents and treats respiratory tract disease, profit intestinal
The effects such as relieving constipation and diuresis row's pouring；Can be clinically used for treatment have sore throat, phlegm-heat cough, calentura excessive thirst, little
The diseases such as the most unfavorable, dysentery.Research shows, the active substance of Corm Eleocharitis is mainly enriched between peel and sarcocarp.?
In the Corm Eleocharitis course of processing, the Corm Eleocharitis cortex amount being dropped accounts for the 25% of fresh Corm Eleocharitis quality, and resource is the abundantest.
We find under study for action, containing abundant luteolin in Corm Eleocharitis skin, but have no at present and extract from Corm Eleocharitis skin
Separate the document report of this compound.
Summary of the invention
It is an object of the invention to: propose a kind of method that Corm Eleocharitis skin extracts luteolin.
The Corm Eleocharitis skin of the present invention extracts the method for luteolin, by traditional extraction method and macroporous resin and gel chromatography
Technology extracts separation luteolin from Corm Eleocharitis skin, specifically comprises the following steps that
(1) fresh Corm Eleocharitis skin is air-dried, pulverize, standby；By weight, take 1 part of Corm Eleocharitis corium farinosum end,
Enter in extraction pot, add Extraction solvent 8-20 part every time, at 50-70 DEG C, extract 1-3h, extract 2-3 altogether
Secondary, filter, merging filtrate, be evaporated to paste, it is thus achieved that extract.
(2) by weight, by extract 1 part, it is dispersed in 5-8 part water and makes turbid solution, with 1-2 times
The ethyl acetate of water volume extracts 3 times, and combining extraction liquid is evaporated to do, it is thus achieved that extract.
(3) by weight, by extract 1 part, it is dissolved in 2-3 part methanol, adds methanol volume 10-15
Water again makes suspension, after macroporous resin adsorption, with methanol aqueous solution or the ethanol of 35% percent by volume
Aqueous solution eluting, thin layer chromatography tracing detection, collect and merge the eluent containing luteolin, concentrating under reduced pressure,
Obtain crude product.
(4) by weight, being dissolved in 4-8 part methanol by crude product 1 part, the water of the methanol volumes such as addition is made outstanding
Turbid liquid, separates with Sephadex LH-20 gel chromatographic columns, and by methanol-eluted fractions, thin layer chromatography detects,
Collect and merge the eluent containing luteolin, concentrating under reduced pressure, vacuum drying, obtain content more than 95%
Luteolin product.
Extraction solvent described in described step (1) is the methanol aqueous solution of 50-75% percent by volume, ethanol
Aqueous solution or aqueous acetone solution therein any one, Extraction solvent volume with Corm Eleocharitis corium farinosum end mass ratio is
8-20m L/g。
Macroporous adsorbent resin used in described step (3) is X-5, NKA-II, D101, AB-8H, NKA-9,
Any one in S-8, D3520, D4020 and H103 type resin；The type of elution of this step is: first use
Washing decontamination, then with the big glycoside of the methanol aqueous solution of 35% percent by volume or ethanol aqueous wash depolarization
Impurity, finally with methanol aqueous solution or the ethanol water of 55-60% percent by volume.
Compared with prior art it provides the benefit that the present invention: design science is reasonable, opens from natural plants
Extracting the new way separating luteolin, good separating effect, product purity is high, makes always to be considered garbage
Corm Eleocharitis skin is turned waste into wealth, selected macroporous resin and gel all can Reusability, raw material is easy to get, aboundresources,
Production cost is low, has preferable application prospect, can carry out large-scale production, meet medical industry needs.
Detailed description of the invention
Below in conjunction with embodiment, the invention will be further described, but embodiments of the present invention are not limited to this.
The Corm Eleocharitis skin of the present invention extracts method traditional extraction method and macroporous resin and the gel chromatography of luteolin
Technology extracts separation luteolin from Corm Eleocharitis skin, specifically comprises the following steps that
(1) fresh Corm Eleocharitis skin is air-dried, pulverize, standby.Weigh the Corm Eleocharitis corium farinosum end of certain mass (g)
Add in extraction pot, add the 50-75% percent by volume of 8-20 times of volume (mL) methanol aqueous solution,
Any one in ethanol water or aqueous acetone solution, extracts 1-3h at 50-70 DEG C, extracts 2-3 altogether
Secondary, filter, merging filtrate, be evaporated to paste, it is thus achieved that extract.
(2) extract (g) is dispersed in the water of 5-8 times of volume (mL) and makes turbid solution, use 1-2
The ethyl acetate of times water volume extracts 3 times, and combining extraction liquid is evaporated to do, it is thus achieved that extract.
(3) extract (g) is dissolved in the methanol of 2-3 times of volume (mL), adds methanol volume 10-15
Water again makes suspension, and by macroporous resin adsorption, big pore adsorption resin is produced by Tianjin Nankai university
NKA-9, X-5, AB-8H, S-8, D3520, NKA-II, D101, D4020 and H103 type resin
In any one, after static adsorption, first wash decontamination with water, then the methanol by 35% percent by volume be water-soluble
Liquid or the big glycoside impurity of ethanol aqueous wash depolarization, finally water-soluble with the methanol of 55-60% percent by volume
Liquid or ethanol water eluting, thin layer chromatography detects, and collects and merges the eluent containing luteolin, decompression
Concentrate, it is thus achieved that crude product.
(4) crude product (g) is dissolved in the methanol of 4-8 times of volume (mL), adds isopyknic water and make outstanding
Turbid liquid, is purified with Sephadex LH-20 gel chromatographic columns, and by methanol-eluted fractions, thin layer chromatography detects,
Collect and merge the eluent containing luteolin, concentrating under reduced pressure, vacuum drying, obtain content more than 95%
Luteolin product.
Embodiment 1
(1) in extraction pot, 800g fresh Corm Eleocharitis corium farinosum end and the third of 6.4L 50% percent by volume is added
Ketone aqueous solution, extracts 2h at 50 DEG C, filters, extract 3 times altogether, and merging filtrate, concentrating under reduced pressure becomes cream
Shape, it is thus achieved that extract 120g.
(2) make turbid solution toward addition 900mL water in extract, be subsequently adding the extraction of 1.8L ethyl acetate
3 times, combining extraction liquid, concentrating under reduced pressure, it is thus achieved that extract 10.5g.
(3) extract is dissolved in 25mL methanol, adds 250mL water and make suspension, proceed to 1kg
D101 macroporous resin chromatographic column adsorbs, and after static adsorption, first washes with water to effluent colourless, then with 35%
The methanol aqueous solution 800mL of percent by volume washes away the glycoside impurity that polarity is big, finally uses 60% volume basis
The methanol aqueous solution eluting of ratio, thin layer chromatography detects, and collects and merges the eluent containing luteolin, decompression
Concentrate, it is thus achieved that luteolin crude product 0.33g.
(4) semi-finished product are dissolved in 3.5mL methanol, add 3.5mL water and make turbid solution, use Sephadex
LH-20 gel chromatography column purification, by methanol-eluted fractions, thin layer chromatography detects, and collects and merges containing luteolin
Eluent, concentrating under reduced pressure, vacuum drying, it is thus achieved that content is the luteolin product 25mg of 95.2%.
Embodiment 2
(1) in extraction pot, 800g fresh shepherd's purse corium farinosum end and the methanol of 1.6L 75% percent by volume are added
Aqueous solution, extracts 2.5h at 70 DEG C, filters, extract 3 times altogether, merging filtrate, concentrating under reduced pressure paste,
Obtain extract 150g.
(2) make turbid solution toward addition 750mL water in extract, add 1.5L ethyl acetate and extract 3 times,
Combining extraction liquid, concentrating under reduced pressure, it is thus achieved that extract 12.0g.
(3) in extract, add the dissolving of 24mL methanol, add 240mL water and make suspension, proceed to 1
The chromatographic column of kg S-8 macroporous resin separates, after static adsorption, first washes with water to effluent colourless, then
Wash away, with the methanol aqueous solution 800mL of 35% percent by volume, the glycoside impurity that polarity is big, finally use 55% body
The methanol aqueous solution eluting of long-pending percentage ratio, thin layer chromatography detects, and collects and merges the eluent containing luteolin,
Concentrating under reduced pressure, it is thus achieved that luteolin semi-finished product 0.28g.
(4) semi-finished product are dissolved in 3.0mL methanol, add 3.0mL water and make suspension, use Sephadex
LH-20 gel chromatography column purification, by methanol-eluted fractions, thin layer chromatography detects, and collects and merges containing luteolin
Eluent, concentrating under reduced pressure, vacuum drying, it is thus achieved that content is the luteolin product 18mg of 95.9%.
Embodiment 3
(1) in extraction pot, adding 800g fresh Corm Eleocharitis corium farinosum end 8.0L volume fraction is the ethanol of 70%
Aqueous solution, extracts at 65 DEG C 1.5 hours, extracts 2 times altogether, filter, merging filtrate, and concentrating under reduced pressure becomes
Paste, it is thus achieved that extract 100g.
(2) make turbid solution toward addition 800mL water in extract, add and take 1.6L ethyl acetate extraction 3
Secondary, merge ester layer, concentrating under reduced pressure, it is thus achieved that extract 9.5g.
(3) extract is dissolved in 19mL methanol, adds 190mL water and make suspension, proceed to 1kg D101
The chromatographic column of macroporous resin adsorbs, and after static adsorption, first washes with water to effluent colourless, then with 35%
The ethanol water 800mL of percent by volume washes away the glycoside impurity that polarity is big, finally uses 58% volume basis
The ethanol water eluting of ratio, thin layer chromatography detects, and collects and merges the eluent containing luteolin, decompression
Concentrate, it is thus achieved that luteolin crude product 0.29g.
(4) crude product is dissolved in 3.0mL methanol, adds 3.0mL water and make turbid solution, use Sephadex LH-20
Gel chromatography column purification, by methanol-eluted fractions, thin layer chromatography detects, and collects and merges the eluting containing luteolin
Liquid, concentrating under reduced pressure, vacuum drying, it is thus achieved that content is the luteolin product 21mg of 95.5%.
Embodiment 4
(1) in extraction pot, add 800g Corm Eleocharitis corium farinosum end and 8.0L volume fraction is the methanol-water of 60%
Solution, extracts 2h at 60 DEG C, extracts 2 times altogether, filter, merging filtrate, concentrating under reduced pressure paste, obtain
Obtain extract 125g.
(2) make turbid solution toward addition 800mL water in extract, add 1.6L ethyl acetate and extract 3 times,
Merge ester layer, concentrating under reduced pressure, it is thus achieved that extract 9.2g.
(3) extract adds 17mL methanol dissolve, add water and make 170mL suspension, proceed to 1kg
D101 macroporous resin chromatographic column adsorbs, after static adsorption, first washes with water to effluent colourless, then use
The ethanol water 800mL of 35% percent by volume washes away the glycoside impurity that polarity is big, finally uses 55% volume
The ethanol water eluting of percentage ratio, collects and merges the eluent containing luteolin, concentrating under reduced pressure, it is thus achieved that wood
Rhinoceros grass element crude product 0.27g.
(4) crude product is dissolved in 2.0mL methanol, adds 2.0mL water and make suspension, use Sephadex LH-20
Gel chromatography column purification, by methanol-eluted fractions, thin layer chromatography detects, and collects and merges the eluting containing luteolin
Liquid, concentrating under reduced pressure, vacuum drying, it is thus achieved that content is the luteolin 18mg of 96.0%.
Products obtained therefrom warp1H-NMR、13C-NMR and ESIMS confirms structure.Spectral data confirms, is carried
Take that purification obtains for luteolin, its chemical structural formula is as follows:
Luteolin, yellow needle-like crystals.1HNMR(400MHz,acetone-d6)δ:6.58(s,H-3),
6.24 (d, J=2.1Hz, H-6), 6.51 (d, J=2.1Hz, H-8), 7.50 (d, J=2.2Hz, H-2 '), 7.00 (d, J=
8.3Hz, H-5 '), 7.47 (dd, J=8.3,2.2Hz, H-6 ')；13C NMR(125MHz,acetone-d6)δ:
165.2(s,C-2),103.9(d,C-3),183.0(s,C-4),163.2(s C-5),99.7(d,C-6),165.5(s,C-7),
94.7(s,C-8),158.7(s,C-9),105.0(s,C-10),123.2(s,C-1′),114.1(d,C-2′),146.8(s,
C-3′),150.6(s,C-4′),116.7(d,C-5′),119.8(d,C-6′)；ESIMS(negative-ion mode)m/z
285[M–H]–。
Claims (2)
1. the method that Corm Eleocharitis skin extracts luteolin, it specifically comprises the following steps that
(1) fresh Corm Eleocharitis skin is air-dried, pulverize, standby；By weight, take 1 part of Corm Eleocharitis corium farinosum end, enter
In extraction pot, add Extraction solvent 8-20 part every time, at 50-70 DEG C, extract 1-3h, extract 2-3 time altogether, mistake
Filter, merging filtrate, it is evaporated to paste, it is thus achieved that extract；
(2) by weight, by extract 1 part, it is dispersed in 5-8 part water and makes turbid solution, with 1-2 times of water body
Long-pending ethyl acetate extracts 3 times, and combining extraction liquid is evaporated to do, it is thus achieved that extract；
(3) by weight, by extract 1 part, it is dissolved in 2-3 part methanol, adds methanol volume 10-15
Times water make suspension, after macroporous resin adsorption, first wash decontamination with water, then by 35% percent by volume
Methanol aqueous solution or the big glycoside impurity of ethanol aqueous wash depolarization, finally with the methanol of 55-60% percent by volume
Aqueous solution or ethanol water eluting, thin layer chromatography tracing detection, collect and merge the eluent containing luteolin,
Concentrating under reduced pressure, it is thus achieved that crude product；
(4) by weight, being dissolved in 4-8 part methanol by crude product 1 part, the water of the methanol volumes such as addition is made suspended
Liquid, separates with Sephadex LH-20 gel chromatographic columns, and by methanol-eluted fractions, thin layer chromatography detects, and collects
Merge the eluent containing luteolin, concentrating under reduced pressure, vacuum drying, obtain content reseda more than 95%
Element product.
Corm Eleocharitis skin the most according to claim 1 extracts the method for luteolin, it is characterised in that described
Macroporous adsorbent resin used in step (3) is X-5, NKA-II, D101, AB-8H, NKA-9, S-8,
Any one in D3520, D4020 and H103 type resin.
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Application publication date: 20150422 Assignee: Guangxi Hengfengda Supply Chain Management Co.,Ltd. Assignor: HEZHOU University Contract record no.: X2023980046610 Denomination of invention: Method for Extracting Luteolin from Water Chestnut Peel Granted publication date: 20160921 License type: Common License Record date: 20231108 Application publication date: 20150422 Assignee: Pingle Leyao Food Co.,Ltd. Assignor: HEZHOU University Contract record no.: X2023980046448 Denomination of invention: Method for Extracting Luteolin from Water Chestnut Peel Granted publication date: 20160921 License type: Common License Record date: 20231108 |