CN104529980A - Method for extracting cryrtominetin from eleocharis tuberose peels - Google Patents
Method for extracting cryrtominetin from eleocharis tuberose peels Download PDFInfo
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- CN104529980A CN104529980A CN201410833026.4A CN201410833026A CN104529980A CN 104529980 A CN104529980 A CN 104529980A CN 201410833026 A CN201410833026 A CN 201410833026A CN 104529980 A CN104529980 A CN 104529980A
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- cryrtominetin
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- methyl alcohol
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- 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
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
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- 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
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- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to a method for extracting cryrtominetin 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 cryrtominetin 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 and purifying with a semi-preparative high-performance liquid chromatography to obtain a cryrtominetin product of which the content of the cryrtominetin is above 95%. By the method, a novel way for extracting and separating the cryrtominetin from natural plants is created, the good 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, specifically relate to a kind of extraction and separation method of cryrtominetin, particularly relate to a kind of method of extraction and isolation cryrtominetin from water chestnut skin.
Background technology
Cryrtominetin (Cyrtominetin), also claims cyrtominetin, and chemistry (R) by name-6,8-dimethyl-5,7,3 ', 4 '-tetrahydroxy flavanone, exists in Dryopteridaceae Cyrtomium plant.Cryrtominetin is that C-methylates flavanone, and this compounds has anti-oxidant, anti-inflammatory, analgesia, the multiple pharmacologically active such as antitumor.Cryrtominetin structure is special, and the distribution in plant less and content is not high.Also do not find at present about the Technology document of extraction and isolation cryrtominetin from plant.
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 cryrtominetin 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 cryrtominetin.
Water chestnut skin of the present invention extracts the method for cryrtominetin, and application traditional extraction method and MCI, polymeric amide and Semipreparative chromatography technology extraction and isolation cryrtominetin from water chestnut skin, specifically comprise step 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% per-cent, 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 2:1-0:1, tlc detects, and collects the elutriant merged containing cryrtominetin, concentrating under reduced pressure, obtains crude product B.
(5) by weight, gained crude product B 1 part is dissolved in 2-5 part methyl alcohol, purify with Semipreparative chromatography, with the methanol aqueous solution of 46-58% volume percent for moving phase, collect the elutriant merged containing cryrtominetin, concentrating under reduced pressure, dry, obtain the cryrtominetin 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 2:1-0:1.
4. method according to claim 1, is characterized in that, the chromatographic column used in described step (6) is Zorbax SB-C18 (9.4mm 25cm) post; Described moving phase is the methanol aqueous solution of 46-58% volume percent.
The present invention compared with prior art its beneficial effect is: design science is reasonable; open the new way of extraction and isolation cryrtominetin 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 and polymeric amide 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.
Water chestnut skin of the present invention extracts the method for cryrtominetin, and application traditional extraction method and MCI, polymeric amide and Semipreparative chromatography technology extraction and isolation cryrtominetin from water chestnut skin, specifically comprise step 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% per-cent, concentrating under reduced pressure, obtain crude product A.
(4) in crude product, methyl alcohol is added to dissolving completely, sample mixed by the polymeric amide adding 2-4 times of quality, by dry for methyl alcohol volatilization, the chromatographic column proceeding to polymeric amide is separated, with the chloroform-methanol wash-out that volume ratio is 2:1-0:1, tlc detects, and collects the elutriant merged containing cryrtominetin, concentrating under reduced pressure, obtains crude product B.
(5) gained crude product B (g) is dissolved in the methyl alcohol of 2-5 times of volume (mL), purify with Semipreparative chromatography, chromatographic column used is Zorbax SB-C18 (9.4mm 25cm) post that Agilent company of the U.S. produces, with the methanol aqueous solution of 46-58% volume percent for moving phase, collect the elutriant merged containing cryrtominetin, concentrating under reduced pressure, dry, obtain the cryrtominetin 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% per-cent, concentrating under reduced pressure, obtains crude product A 31g.
Be dissolved in 90mL methyl alcohol by crude product A, add 60g polymeric amide and mix sample, by dry for methyl alcohol volatilization, proceed to polyamide column and be separated, by methanol-eluted fractions, tlc detects, and collects the elutriant merged containing cryrtominetin, concentrating under reduced pressure, obtains crude product B 0.28g.
Gained crude product C is dissolved in 1.0mL methyl alcohol, purifies with Semipreparative chromatography, with the methanol aqueous solution of 52% volume percent for moving phase, collect the elutriant merged containing cryrtominetin, concentrating under reduced pressure, dry, obtain the cryrtominetin 8.0mg that content is 96.8%.
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% per-cent, 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 1:2 by volume ratio, and tlc detects, collect the elutriant merged containing cryrtominetin, concentrating under reduced pressure, obtain crude product B 0.25g.
Gained crude product C is dissolved in 1.0mL methyl alcohol, purifies with Semipreparative chromatography, with the methanol aqueous solution of 51% volume percent for moving phase, collect the elutriant merged containing cryrtominetin, concentrating under reduced pressure, dry, obtain the cryrtominetin 9.0mg that content is 95.2%.
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% per-cent, 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 cryrtominetin, concentrating under reduced pressure, obtain crude product B 0.19g.
Gained crude product C is dissolved in 1.0mL methyl alcohol, purifies with Semipreparative chromatography, with the methanol aqueous solution of 54% volume percent for moving phase, collect the elutriant merged containing cryrtominetin, concentrating under reduced pressure, dry, obtain the cryrtominetin 4.0mg that content is 96.1%.
Products obtained therefrom warp
1h-NMR,
13c-NMR and ESIMS chromatogram confirms.Spectral data confirms, the compound that institute's extraction purification obtains is cryrtominetin, and its chemical structural formula is as follows:
Cryrtominetin, buff powder.
1H NMR(400MHz,Methanol-d
4)δ:5.22(dd,J＝12.6,2.7Hz,H-2),3.00(dd,J＝17.0,12.7Hz,H
a-3),2.69(dd,J＝17.0,2.7Hz,H
b-3),6.78(s,H-2′),6.94(s,H-5′),6.78(s,H-6′),1.99(s,3H,CH
3-8),1.98(s,3H,CH
3-6)；
13CNMR(125MHz,Methanol-d
4)δ:80.0(d,C-2),44.1(t,C-3),198.3(s,C-4),160.2(sC-5),104.7(s,C-6),164.3(s,C-7),104.1(s,C-8),159.3(s,C-9),103.2(s,C-10),132.2(s,C-1′),114.5(d,C-2′),146.5(s,C-3′),146.7(s,C-4′),116.2(d,C-5′),119.0(d,C-6′),8.2(q,CH
3-6),7.4(q,CH
3-8)；ESIMS(negative-ion mode)m/z 315[M–H]
–。
Claims (4)
1. water chestnut skin extracts a method for cryrtominetin, 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% per-cent, 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 2:1-0:1, tlc detects, and collects the elutriant merged containing cryrtominetin, concentrating under reduced pressure, obtains crude product B.
(5) by weight, gained crude product B 1 part is dissolved in 2-5 part methyl alcohol, purify with Semipreparative chromatography, with the methanol aqueous solution of 46-58% volume percent for moving phase, collect the elutriant merged containing cryrtominetin, concentrating under reduced pressure, dry, obtain the cryrtominetin 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 2:1-0:1.
4. method according to claim 1, is characterized in that, the chromatographic column used in described step (6) is Zorbax SB-C18 (9.4mm 25cm) post; Described moving phase is the methanol aqueous solution of 46-58% volume percent.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1636569A (en) * | 1927-07-19 | Douglas william kent-jones and charles woodland chitty | ||
| US20040038914A1 (en) * | 2000-06-28 | 2004-02-26 | Jean Krutmann | Flavone/ flavanone derivatives for the systemic treatment and prophlaxis of uv-induced dermatoses |
| CN101602754A (en) * | 2009-07-16 | 2009-12-16 | 李青山 | A kind of flavanone derivatives and its production and use |
-
2014
- 2014-12-29 CN CN201410833026.4A patent/CN104529980A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1636569A (en) * | 1927-07-19 | Douglas william kent-jones and charles woodland chitty | ||
| US20040038914A1 (en) * | 2000-06-28 | 2004-02-26 | Jean Krutmann | Flavone/ flavanone derivatives for the systemic treatment and prophlaxis of uv-induced dermatoses |
| CN101602754A (en) * | 2009-07-16 | 2009-12-16 | 李青山 | A kind of flavanone derivatives and its production and use |
Non-Patent Citations (3)
| Title |
|---|
| F.URSINI等: "A NOVEL ANTIOXIDANT FLAVONOID (IdB 1031) AFFECTING MOLECULAR MECHANISMS OF CELLULAR ACTIVATION", 《FREE RADICAL BIOLOGY & MEDICINE》, vol. 16, no. 5, 31 December 1994 (1994-12-31) * |
| TSUKASA IWASHINA等: "Flavonoids in the species of Cyrtomium (Dryopteridaceae) and related genera", 《BIOCHEMICAL SYSTEMATICS AND ECOLOGY》, vol. 34, 31 December 2006 (2006-12-31) * |
| 盛景芬等: "东北贯众抗血吸虫有效成分的分离鉴定", 《药学通报》, vol. 16, no. 2, 31 December 1981 (1981-12-31) * |
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