CN104592247A - Method for extracting eleocharin F - Google Patents
Method for extracting eleocharin F Download PDFInfo
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- CN104592247A CN104592247A CN201410833074.3A CN201410833074A CN104592247A CN 104592247 A CN104592247 A CN 104592247A CN 201410833074 A CN201410833074 A CN 201410833074A CN 104592247 A CN104592247 A CN 104592247A
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- water chestnut
- methyl alcohol
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- water
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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Abstract
The invention discloses a method for extracting eleocharin F, particularly relates to a method for extracting and separating eleocharin F from eleocharis tuberosa peels and belongs to the field of natural organic chemistry. The method is characterized by comprising the following steps of extracting eleocharin F from the eleocharis tuberosa peels in an aqueous solution of acetone as a solvent, extracting an extract with ethyl acetate, separating an extractant by virtue of a middle-pressure MCI and polyamide chromatographic column and purifying with Sephadex LH-20 gel and MCI chromatographic column to obtain an eleocharin F product of which the content of eleocharin F is not less than 95%. According to the method, eleocharin F is extracted and separated from waste eleocharis tuberosa peels, good separation effect is achieved, the product is high in purify, 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 has better application prospects.
Description
Technical field
The invention belongs to field of natural organic chemistry, relate to the extraction and separation method of oneself element of a kind of water chestnut, particularly relate to a kind of method of oneself element of extraction and isolation water chestnut from water chestnut skin.
Background technology
The own element (Eleocharin F) of water chestnut, chemistry (+)-(Z)-8-(3,4-dihydroxy-benzene methylene radical)-5-hydroxyl-2 by name, 2-dimethyl-2H-furo [2,3-h] chromene-9-ketone, be orange powder, its molecular formula is C
20h
16o
6, molecular weight is 352.0946, is dissolved in methyl alcohol, ethanol, acetone.Oneself element of water chestnut is the derivative of aureusidin, belongs to Aurone compound.This compounds has the multiple pharmacologically actives such as anti-oxidant, antibacterial, antitumor, antiviral, anti-inflammatory, antianaphylaxis.
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 have found the own plain new compound of water chestnut in the research of water chestnut skin activeconstituents extraction and isolation, 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: the extracting method proposing oneself element of a kind of water chestnut.
The extracting method of oneself element of water chestnut of the present invention, utilize traditional extraction method and the own element of MCI, polymeric amide and gel chromatography technology extraction and isolation water chestnut, 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 oneself element of water chestnut, concentrating under reduced pressure, obtains crude product B.
(5) by weight, by crude product B1 part, be dissolved in 4-8 part methyl alcohol, add isopyknic water and make suspension liquid, with Sephadex LH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, collect the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, obtain crude product C.
(6) by weight, gained crude product C1 part is dissolved in 3-6 part methyl alcohol, the water adding 2 times of methyl alcohol volumes makes suspension liquid, use MCI chromatography, with the methanol aqueous solution wash-out of 68-80% volume percent, tlc detects, collect the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, dry, obtain the own plain product of water chestnut that content reaches more than 95%.
Described MCI post specification in described step (3) is 70 × 460mm, and 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, 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; utilize discarded water chestnut skin for the own element of raw material extraction and isolation water chestnut; good separating effect, product purity is high, and water chestnut skin 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, there is good application prospect.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but embodiments of the present invention are not limited thereto.
The extracting method of oneself element of water chestnut of the present invention, utilize traditional extraction method and the own element of MCI, polymeric amide and gel chromatography technology extraction and isolation water chestnut, 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 volume of water 1-2 extraction into ethyl acetate doubly 3 times, 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 oneself element of water chestnut, 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 oneself element of water chestnut, concentrating under reduced pressure, obtain crude product C.
(6) gained crude product C (g) is dissolved in the methyl alcohol of 3-6 times of volume (mL), the water adding 2 times of methyl alcohol volumes makes suspension liquid, use MCI chromatography, with the methanol aqueous solution wash-out of 68-80% volume percent, tlc detects, and collects the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, drying, obtains the own plain product of water chestnut 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, adds 60g polymeric amide and mix sample, by dry for methyl alcohol volatilization, proceeding to polyamide column to be separated, is the chloroform-methanol wash-out of 2:1 by volume ratio, and tlc detects, collect the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, obtain crude product B 1.4g.
Be dissolved in the methyl alcohol of 6.0mL by crude product B, add 6.0mL water and make suspension liquid, with Sephadex LH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, obtains crude product C 150mg.
Gained crude product C is dissolved in 1.0mL methyl alcohol, add 2.0mL water and make suspension liquid, use MCI chromatography, with the methanol aqueous solution wash-out of 73% volume percent, tlc detects, and collects the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, drying, obtains the own plain 16.0mg of water chestnut that content is 95.2%.
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, adds 60g polymeric amide and mix sample, by dry for methyl alcohol volatilization, proceeding to polyamide column to be separated, is the chloroform-methanol wash-out of 3:1 by volume ratio, and tlc detects, collect the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, obtain crude product B 0.93g.
Be dissolved in the methyl alcohol of 4.0mL by crude product B, add 4.0mL water and make suspension liquid, with Sephadex LH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, obtains crude product C 110mg.
Gained crude product C is dissolved in 0.5mL methyl alcohol, add 2.0mL water and make suspension liquid, use MCI chromatography, with the methanol aqueous solution wash-out of 73% volume percent, tlc detects, and collects the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, drying, obtains the own plain 12.0mg of water chestnut that content is 97.0%.
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, adds 60g polymeric amide and mix sample, by dry for methyl alcohol volatilization, proceeding to polyamide column to be separated, is the chloroform-methanol wash-out of 1:1 by volume ratio, and tlc detects, collect the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, obtain crude product B 1.0g.
Be dissolved in the methyl alcohol of 4.0mL by crude product B, add 4.0mL water and make suspension liquid, with Sephadex LH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, obtains crude product C 130mg.
Gained crude product C is dissolved in 1.0mL methyl alcohol, add 2.0mL water and make suspension liquid, use MCI chromatography, with the methanol aqueous solution wash-out of 73% volume percent, tlc detects, and collects the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, drying, obtains the own plain 17mg of water chestnut that content is 96.2%.
Products obtained therefrom is used
1h-NMR,
13c-NMR, IR, HREIMS, UV carry out Structural Identification.Spectral data confirms, oneself chemical structural formula of element of the purified water chestnut obtained is as follows:
Oneself is plain for water chestnut, orange amorphous powder.[α] 16D:+1.7 (c 0.58, MeOH), IR (KBr) ν
max: 3427,2919,1737,1631,1476,1384,1266,1180,1118cm
-1, UV (MeOH): λ
max(log ε) 405.5 (3.53), 285.0 (3.44), 203.0 (3.91) nm,
1h NMR (600MHz, DMSO-d
6) δ: 5.85 (s, H-7), 6.20 (s, H-10), 7.34 (d, J=1.8Hz, H-2 '), 6.77 (d, J=8.2Hz, H-5 '), 7.07 (dd, J=8.2,1.8Hz, H-6 '), 6.52 (d, J=9.9Hz, H-1 "), 5.32 (d, J=9.9Hz, H-2 "), 1.37 (s, 3H, H-4 "), 1.37 (s, 3H, H-5 "), 8.41 (br s, HO-7),
13c NMR (150MHz, DMSO-d
6) δ: 147.5 (s, C-2), 176.6 (s, C-3), 153.0 (s, C-4), 106.1 (s C-5), 167.2 (s, C-6), 92.7 (d, C-7), 167.1 (s, C-8), 98.7 (s, C-9), 106.9 (d, C-10), 124.5 (s, C-1 '), 117.1 (d, C-2 '), 145.6 (s, C-3 '), 146.9 (s, C-4 '), 116.1 (d, C-5 '), 123.3 (d, C-6 '), 118.4 (d, C-1 "), 122.8 (d, C-2 "), 76.9 (s, C-3 "), 28.0 (q, C-4 "), 28.0 (q, C-5 "), ESIMS (positive-ion mode) m/z 375 [M+Na]
+, HREIMS m/z 352.0946 [M]
+, C
20h
16o
6calculated value is 352.0947..
Claims (3)
1. an extracting method for oneself element of water chestnut, 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 oneself element of water chestnut, concentrating under reduced pressure, obtains crude product B.
(5) by weight, by crude product B1 part, be dissolved in 4-8 part methyl alcohol, add isopyknic water and make suspension liquid, with Sephadex LH-20 gel chromatography column purification, by methanol-eluted fractions, tlc detects, collect the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, obtain crude product C.
(6) by weight, gained crude product C1 part is dissolved in 3-6 part methyl alcohol, the water adding 2 times of methyl alcohol volumes makes suspension liquid, use MCI chromatography, with the methanol aqueous solution wash-out of 68-80% volume percent, tlc detects, collect the elutriant merged containing oneself element of water chestnut, concentrating under reduced pressure, dry, obtain the own plain product of water chestnut 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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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111990416A (en) * | 2020-09-22 | 2020-11-27 | 河北农业大学 | Insecticidal substance, insecticide and preparation method and application thereof |
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| CN103589185A (en) * | 2013-10-28 | 2014-02-19 | 南昌大学 | Method for extracting pigment and polyphenol from water chestnut peels |
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2014
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| CN101270230A (en) * | 2008-05-20 | 2008-09-24 | 贺州学院 | Method for auxiliary extraction of chufa husk natural brown vegetarian with ultrasound wave |
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Application publication date: 20150506 |