CN104529975A - Method for extracting 6-methylluteolin from eleocharis tuberose peels - Google Patents
Method for extracting 6-methylluteolin from eleocharis tuberose peels Download PDFInfo
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- CN104529975A CN104529975A CN201410833028.3A CN201410833028A CN104529975A CN 104529975 A CN104529975 A CN 104529975A CN 201410833028 A CN201410833028 A CN 201410833028A CN 104529975 A CN104529975 A CN 104529975A
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- VSHICDFQSGJNPK-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methylchromen-4-one Chemical compound C=1C(=O)C2=C(O)C(C)=C(O)C=C2OC=1C1=CC=C(O)C(O)=C1 VSHICDFQSGJNPK-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 13
- 241000202829 Eleocharis Species 0.000 title abstract 4
- 235000016067 Polianthes tuberosa Nutrition 0.000 title abstract 4
- 244000014047 Polianthes tuberosa Species 0.000 title abstract 4
- 239000000284 extract Substances 0.000 claims abstract description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 9
- 238000000926 separation method Methods 0.000 claims abstract description 9
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 129
- 239000012043 crude product Substances 0.000 claims description 36
- 235000003283 Pachira macrocarpa Nutrition 0.000 claims description 29
- 235000014364 Trapa natans Nutrition 0.000 claims description 29
- 235000009165 saligot Nutrition 0.000 claims description 29
- 241001083492 Trapa Species 0.000 claims description 26
- 238000000605 extraction Methods 0.000 claims description 22
- 150000001408 amides Chemical class 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 238000012856 packing Methods 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 abstract description 5
- 229920002647 polyamide Polymers 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 description 5
- 240000001085 Trapa natans Species 0.000 description 4
- 238000007654 immersion Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241000234646 Cyperaceae Species 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
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- 239000013543 active substance Substances 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
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000013461 design Methods 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
- 208000001848 dysentery Diseases 0.000 description 1
- 206010013990 dysuria Diseases 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
- 239000013505 freshwater Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000002659 luteolin Chemical class 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 206010036067 polydipsia Diseases 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003786 synthesis reaction 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
- C07D311/40—Separation, e.g. from natural material; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for extracting 6-methylluteolin from eleocharis tuberose peels and belongs to the field of natural organic chemistry. The method is characterized by comprising the following steps of as an aqueous solution of acetone is used as a solvent, extracting the 6-methylluteolin from the eleocharis tuberose peels to obtain an extract, extracting the extract with ethyl acetate to obtain an extractant, separating the extractant with a medium-pressure MCI column chromatography and a polyamide column chromatography, purifying with a SephadexLH-20 gel chromatography and finally recrystallizing to obtain a 6-methylluteolin product of which the content of the 6-methylluteolin is above 95%. By the method, a novel way for extracting and separating 6-methylluteolin from natural plants is created, god separation effect is achieved, the product is high in purity, the eleocharis tuberose peels always regarded as wastes are changed into treasure, chromatographic materials, namely, MCI, polyamide and sol, can be repeatedly used, and the method has the advantages that raw materials are easily available, resources are abundant and the production cost is low, the product can be subjected to large-scale production and meets the needs of pharmaceutical industry.
Description
Technical field
The invention belongs to field of natural organic chemistry, relate to a kind of extraction and separation method of 6-methyl luteolin, particularly relate to a kind of method carrying middle extraction and isolation 6-methyl luteolin from water chestnut skin.
Background technology
6-methyl luteolin (6-Methylluteolin), yellow crystals, chemistry 6-methyl-5,7 by name, 3 ', 4 '-kaempferol is the C-methylated derivative of luteolin.This flavonoids has multiple pharmacologically active, as anti-oxidant, antibacterial, antitumor etc.6-methyl luteolin structure is unique, and distributed in nature is few, and pertinent literature is also few, and people are obtained by synthesis usually.Do not find the extraction and separation technology introduction about 6-methyl luteolin at present.
Water chestnut (Eleocharis tuberosa), also known as water chestnut, belong to the underground bulb of Cyperaceae perennial shallow water herbaceous plant water chestnut, China's most area has cultivation.Wherein, Guangxi water chestnut output accounts for the whole nation 70%, and He Prefecture water chestnut output accounts for Guangxi 70%.According to the literature, water chestnut have antibacterial, antitumor, prevent and treat respiratory tract disease, sharp intestines defaecation and effect such as diuresis row pouring etc.; Can be used for the diseases such as treatment is had sore throat, phlegm heat cough, pyreticosis polydipsia, dysuria, dysentery clinically.Research shows, the active substance of water chestnut is mainly enriched between pericarp and pulp.In the water chestnut course of processing, the water chestnut cortex amount be dropped accounts for 25% of fresh water chestnut quality, and resource is very abundant.We find containing 6-methyl luteolin in water chestnut skin under study for action, but have no the bibliographical information of this compound of extraction and isolation from water chestnut skin at present.
Summary of the invention
The object of the invention is to: propose a kind of method that water chestnut skin extracts 6-methyl luteolin.
6-methyl luteolin, its chemical structural formula is as follows:
Water chestnut skin of the present invention extracts the method for 6-methyl luteolin, application traditional extraction method and MCI, polymeric amide and gel chromatography technology extraction and isolation 6-methyl luteolin from water chestnut skin, and concrete steps are as follows:
(1) the water chestnut skin by fresh is air-dry, pulverizes, for subsequent use; By weight, take 1 part, water chestnut skin powder, add in extractor, add the aqueous acetone solution of 4-10 part 70% volume percent at every turn, at 25 DEG C, soak 24h, soak 3 times, filter, merging filtrate, is evaporated to paste, obtains extract.
(2) by weight, be dispersed in 5 parts of water by extract 1 part and make suspension liquid, with the extraction into ethyl acetate 3 times of 1-2 times of volume of water, combining extraction liquid, is evaporated to dry, obtains extract.
(3) in extract, methyl alcohol is added to dissolving completely, sample is mixed with the polymeric amide of 2-4 times of extract quality, methyl alcohol is evaporated into dry, dress post, connects MCI post and carries out the separation of middle pressure, with the methanol aqueous solution of 40-100% volume percent for eluent gradient wash-out, tlc detects, collect and merge the elutriant that moving phase concentration is 70-90% volume percent, concentrating under reduced pressure, obtain crude product A.
(4) in crude product A, methyl alcohol is added to dissolving completely, sample is mixed with the polymeric amide of 2-4 times of quality, methyl alcohol is evaporated into dry, proceed to polymeric amide chromatographic column to be separated, with the chloroform-methanol wash-out that volume ratio is 3:1-1:1, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product B.
(5) by weight, crude product B1 part is dissolved in 4-8 part methyl alcohol, the water methyl alcohol volume such as adding makes suspension liquid, with Sephadex LH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product C.
(6) by gained crude product C through methyl alcohol or ethyl alcohol recrystallization, dry, obtain the 6-methyl luteolin product that content reaches more than 95%.
Described MCI post specification in described step (3) is 70 × 460mm, and packing material is MCI-gelCHP-20P, and column chromatography condition is: post pressure is 80Psi, and flow rate of mobile phase is 50mL/min, and determined wavelength is 245nm; Described moving phase is the methanol aqueous solution of 40-100% volume percent.
Polymeric amide described in described step (4), specification is 200-300 order; The chloroform-methanol of elutriant used to be volume ratio be 3:1-1:1.
The present invention compared with prior art its beneficial effect is: design science is reasonable; open the new way of extraction and isolation 6-methyl luteolin from natural phant; good separating effect, product purity is high, and the water chestnut skin being always regarded as waste is turned waste into wealth; selected chromatographic material MCI, polymeric amide and gel all can Reusabilities; raw material is easy to get, aboundresources, and production cost is low; can large-scale production be carried out, meet medicine industry needs.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but embodiments of the present invention are not limited thereto.
Water chestnut skin of the present invention extracts the method for 6-methyl luteolin, application traditional extraction method and MCI, polymeric amide and gel chromatography technology extraction and isolation 6-methyl luteolin from water chestnut skin, and concrete steps are as follows:
(1) the water chestnut skin by fresh is air-dry, pulverizes, for subsequent use.The water chestnut skin powder taking certain mass (g) adds in extractor, then adds the aqueous acetone solution of 70% volume percent of 4-10 times of volume (mL), at 25 DEG C, soak 24h, soak 3 times, filter, merging filtrate, be evaporated to paste, obtain extract.
(2) be dispersed in by extract (g) in the water of 5 times of volumes (mL) and make suspension liquid, with the extraction into ethyl acetate 3 times of 1-2 times of volume of water, combining extraction liquid, is evaporated to dry, obtains extract.
(3) in extract, methyl alcohol is added to dissolving completely, sample is mixed with the polymeric amide of 2-4 times of extract quality, methyl alcohol is evaporated into dry, dress post, connect MCI post and carry out the separation of middle pressure, post specification is 70mm × 460mm, packing material is the MCI-gel CHP-20P that Mitsubishi chemical company produces, column chromatography condition is: post pressure is 80Psi, flow rate of mobile phase is 50mL/min, determined wavelength is 254nm, with the methanol aqueous solution of 40-100% volume percent for eluent gradient wash-out, eluate concentration is regulated according to detected peaks changing conditions, collect by every part of 500mL, tlc detects, collect and merge the elutriant that moving phase concentration is 70-90% volume percent, concentrating under reduced pressure, obtain crude product A.
(4) in crude product A, methyl alcohol is added to dissolving completely, sample is mixed with the polymeric amide of 2-4 times of quality, methyl alcohol is evaporated into dry, proceed to polymeric amide chromatographic column to be separated, with the chloroform-methanol wash-out that volume ratio is 3:1-1:1, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product B.
(5) crude product B (g) is dissolved in the methyl alcohol of 4-8 times of volume (mL), the water methyl alcohol volume such as adding makes suspension liquid, with the Sephadex LH-20 gel chromatography column purification that Amersham Pharmacia Biotech company of Sweden produces, by methanol-eluted fractions, tlc detects, collect the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtain crude product C.
(6) by gained crude product C through methyl alcohol or ethyl alcohol recrystallization purifying, dry, obtain the 6-methyl luteolin product that content reaches more than 95%.
Embodiment 1
Be added in extractor by fresh for 8kg water chestnut skin powder, add the aqueous acetone solution of 32L 70% volume percent, at 25 DEG C, soak 24h, total immersion steeps 3 times, filters, merging filtrate, concentrating under reduced pressure paste, obtains extract 1.05kg.
Extract is added in 5.0L water and make turbid solution, with 5.0L extraction into ethyl acetate 3 times, combining extraction liquid, concentrating under reduced pressure, obtain extract 120g.
300mL dissolve with methanol is added in extract, sample is mixed with 260g polymeric amide, methyl alcohol is evaporated into dry, dress post, connect MCI post and carry out the separation of middle pressure, be eluent gradient wash-out with the methanol aqueous solution of 40-100% volume percent, collect by every part of 500mL, tlc detects, and collects and merges the elutriant that moving phase concentration is 70-90% volume percent, concentrating under reduced pressure, obtains crude product A 31g.
Crude product A is dissolved in 90mL methyl alcohol, add 60g polymeric amide and mix sample, by dry for methyl alcohol volatilization, proceed to polyamide column to be separated, with the chloroform-methanol wash-out that volume ratio is 2:1, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product B 1.1g.
Crude product B is dissolved in the methyl alcohol of 5.0mL, adds 5.0mL water and make suspension liquid, with SephadexLH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product C 0.12g.
By gained crude product C through recrystallizing methanol purifying, dry, obtain the 6-methyl luteolin product 8.0mg of content 95.4%.
Embodiment 2
Be added in extractor by fresh for 8kg water chestnut skin powder, add the aqueous acetone solution of 32L 70% volume percent, at 25 DEG C, soak 24h, total immersion steeps 3 times, filters, merging filtrate, concentrating under reduced pressure paste, obtains extract 1.05kg.
Extract is added in 5.0L water and make turbid solution, with 5.0L extraction into ethyl acetate 3 times, combining extraction liquid, concentrating under reduced pressure, obtain extract 120g.
300mL dissolve with methanol is added in extract, sample is mixed with 260g polymeric amide, methyl alcohol is evaporated into dry, dress post, connect MCI post and carry out the separation of middle pressure, be eluent gradient wash-out with the methanol aqueous solution of 40-100% volume percent, collect by every part of 500mL, tlc detects, and collects and merges the elutriant that moving phase concentration is 70-90% volume percent, concentrating under reduced pressure, obtains crude product A 31g.
Crude product A is dissolved in 90mL methyl alcohol, add 60g polymeric amide and mix sample, by dry for methyl alcohol volatilization, proceed to polyamide column to be separated, with the chloroform-methanol wash-out that volume ratio is 2.5:1, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product B 0.95g.
Crude product B is dissolved in the methyl alcohol of 5.0mL, adds 5.0mL water and make suspension liquid, with SephadexLH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product C 0.10g.
By gained crude product C through ethyl alcohol recrystallization purifying, dry, obtain the 6-methyl luteolin product 9.5mg of content 96.0%.
Embodiment 3
Be added in extractor by fresh for 8kg water chestnut skin powder, add the aqueous acetone solution of 32L 70% volume percent, at 25 DEG C, soak 24h, total immersion steeps 3 times, filters, merging filtrate, concentrating under reduced pressure paste, obtains extract 1.05kg.
Extract is added in 5.0L water and make turbid solution, with 5.0L extraction into ethyl acetate 3 times, combining extraction liquid, concentrating under reduced pressure, obtain extract 120g.
300mL dissolve with methanol is added in extract, sample is mixed with 260g polymeric amide, methyl alcohol is evaporated into dry, dress post, connect MCI post and carry out the separation of middle pressure, be eluent gradient wash-out with the methanol aqueous solution of 40-100% volume percent, collect by every part of 500mL, tlc detects, and collects and merges the elutriant that moving phase concentration is 70-90% volume percent, concentrating under reduced pressure, obtains crude product A 31g.
Crude product A is dissolved in 90mL methyl alcohol, add 60g polymeric amide and mix sample, by dry for methyl alcohol volatilization, proceed to polyamide column to be separated, with the chloroform-methanol wash-out that volume ratio is 1:1, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product B 1.25g.
Crude product B is dissolved in the methyl alcohol of 15.0mL, adds 15.0mL water and make suspension liquid, with SephadexLH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product C 115mg.
By gained crude product C through recrystallizing methanol purifying, dry, obtain the 6-methyl luteolin product 7.0mg of content 98.1%.
Products obtained therefrom warp
1h-NMR,
13c-NMR and ESIMS confirms structure.Spectral data confirms, what institute's extraction purification obtained is 6-methyl luteolin, and its chemical structural formula is as follows:
6-methyl luteolin, yellow crystals.
1H NMR(400MHz,Methanol-d
4)δ:6.45(s,H-3),6.49(s,H-8),7.34(br s,H-2′),6.88(br s,H-5′),7.34(br s,H-6′),2.03(s,3H,CH
3-6)；
13C NMR(125MHz,Methanol-d
4)δ:164.1(s,C-2),103.8(d,C-3),183.9(s,C-4),160.1(s C-5),109.1(s,C-6),166.1(s,C-7),94.0(d,C-8),157.1(s,C-9),105.0(s,C-10),123.8(s,C-1′),114.2(d,C-2′),147.2(s,C-3′),151.1(s,C-4′),116.9(d,C-5′),120.3(d,C-6′),7.6(q,CH
3-6)；ESIMS(negative-ion mode)m/z 299[M–H]
–。
Claims (3)
1. water chestnut skin extracts a method for 6-methyl luteolin, and its concrete steps are as follows:
(1) the water chestnut skin by fresh is air-dry, pulverizes, for subsequent use; By weight, take 1 part, water chestnut skin powder, add in extractor, add the aqueous acetone solution of 4-10 part 70% volume percent at every turn, at 25 DEG C, soak 24h, soak 3 times, filter, merging filtrate, is evaporated to paste, obtains extract.
(2) by weight, be dispersed in 5 parts of water by extract 1 part and make suspension liquid, with the extraction into ethyl acetate 3 times of 1-2 times of volume of water, combining extraction liquid, is evaporated to dry, obtains extract.
(3) in extract, methyl alcohol is added to dissolving completely, sample is mixed with the polymeric amide of 2-4 times of extract quality, methyl alcohol is evaporated into dry, dress post, connects MCI post and carries out the separation of middle pressure, with the methanol aqueous solution of 40-100% volume percent for eluent gradient wash-out, tlc detects, collect and merge the elutriant that moving phase concentration is 70-90% volume percent, concentrating under reduced pressure, obtain crude product A.
(4) in crude product A, methyl alcohol is added to dissolving completely, sample is mixed with the polymeric amide of 2-4 times of quality, methyl alcohol is evaporated into dry, proceed to polymeric amide chromatographic column to be separated, with the chloroform-methanol wash-out that volume ratio is 3:1-1:1, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product B.
(5) by weight, crude product B1 part is dissolved in 4-8 part methyl alcohol, the water methyl alcohol volume such as adding makes suspension liquid, with Sephadex LH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing 6-methyl luteolin, concentrating under reduced pressure, obtains crude product C.
(6) by gained crude product C through methyl alcohol or ethyl alcohol recrystallization, dry, obtain the 6-methyl luteolin product that content reaches more than 95%.
2. method according to claim 1, is characterized in that, the described MCI post specification in described step (3) is 70 × 460mm, packing material is MCI-gel CHP-20P, column chromatography condition is: post pressure is 80Psi, and flow rate of mobile phase is 50mL/min, and determined wavelength is 245nm; Described moving phase is the methanol aqueous solution of 40-100% volume percent.
3. method according to claim 1, is characterized in that, the polymeric amide described in described step (4), and specification is 200-300 order; The chloroform-methanol of elutriant used to be volume ratio be 3:1-1:1.
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| CN101269161A (en) * | 2008-05-20 | 2008-09-24 | 贺州学院 | Technique for extracting total flavone from eleocharis dulcis trin.ex henschel husk |
| CN103087546A (en) * | 2013-01-18 | 2013-05-08 | 江汉大学 | Method for extracting pigments in eleocharis tuberose peel |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101269161A (en) * | 2008-05-20 | 2008-09-24 | 贺州学院 | Technique for extracting total flavone from eleocharis dulcis trin.ex henschel husk |
| CN103087546A (en) * | 2013-01-18 | 2013-05-08 | 江汉大学 | Method for extracting pigments in eleocharis tuberose peel |
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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 6-Methyl Luteolin from Water Chestnut Peel Granted publication date: 20160706 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 6-Methyl Luteolin from Water Chestnut Peel Granted publication date: 20160706 License type: Common License Record date: 20231108 |