CN106905278A - A kind of separation from falcate crazyweed herb prepares 5 kinds of methods with antiinflammatory active compound - Google Patents
A kind of separation from falcate crazyweed herb prepares 5 kinds of methods with antiinflammatory active compound Download PDFInfo
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- CN106905278A CN106905278A CN201710153628.9A CN201710153628A CN106905278A CN 106905278 A CN106905278 A CN 106905278A CN 201710153628 A CN201710153628 A CN 201710153628A CN 106905278 A CN106905278 A CN 106905278A
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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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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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
- C07D311/30—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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- 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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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Abstract
5 kinds of methods with antiinflammatory active compound are prepared the invention discloses a kind of separation from falcate crazyweed herb, 5 kinds of compounds are pinocembrin, the methoxy chalcones of 4 hydroxyl 2,7 hydroxyl dihydro anthoxanthins, 2,4 dihydroxy dihydrochalcones and 2,4 dihydroxy chalcones, comprise the following steps：(1) falcate crazyweed herb extractive of general flavone is taken, is extracted with petroleum ether and ethyl acetate successively, take ethyl acetate extract；(2) ethyl acetate extract dried powder is taken, purifying resin, methyl alcohol wash-out takes eluate, dries, and obtains purified；(3) purified is separated with preparative chromatography, obtains pinocembrin, the methoxy chalcones of 4 hydroxyl 2,7 hydroxyl dihydro anthoxanthins, 2, the 4 dihydroxy dihydrochalcones and 2 of high-purity, 4 dihydroxy chalcones.The method preparation amount is big, and product purity is high, is suitable for commercial Application.
Description
Technical field
5 kinds of methods with antiinflammatory active compound are prepared the present invention relates to a kind of separation from falcate crazyweed herb.
Background technology
Oxytropis falcate Bunge (Oxytropis falcate Bunge) (the entitled cowherb of Tibetan medicine reaches the summer) is pulse family
(Leguminosae) Genus Oxytropis Dc (Oxytropis D.C.) herbaceos perennial.It is grown in river shoal, the sand of 2700~4300m
Ground, hillside, grassy marshland, mainly originate in Qinghai-Tibet Platean.According to《Jingzhubencao》Record, falcate crazyweed herb have healing the open sore part, it is convenient, prevent
Spur produces, it is ailing to control, except poison, hemostasis the effect of, and can disinfect, treat anthracnose, leprosy and influenza, tonsillitis.
Clinical research proves that falcate crazyweed herb has unique curative effect for prevention, treatment influenza and chronic bronchitis.It is many
It is well known, because classes of compounds is numerous and content differs in plant, directly height with practical value is largely obtained from plant
Pure compound be it is extremely difficult, especially when need therefrom simultaneously extract multiple target compounds when, then it is more difficult.Cause
This although including multiple compounds in known falcate crazyweed herb, does not have with it as raw material, while obtaining various high-purities at present
The report of reactive compound.
The content of the invention
To solve the above problems, separating 5 kinds of preparation from falcate crazyweed herb the invention provides one kind has anti-inflammatory activity
The method of compound, the described 5 kinds compounds with anti-inflammatory activity are pinocembrin, the methoxy chalcones of 4- hydroxyls -2,7- hydroxyls two
Hydrogen flavones, 2,4- dihydroxy-dihydrochalcone and 2,4- dihydroxy-chalcone, comprise the following steps：
(1) falcate crazyweed herb extractive of general flavone is taken, is extracted with petroleum ether and ethyl acetate successively, take ethyl acetate extract；
(2) ethyl acetate extract dried powder is taken, purifying resin, methyl alcohol wash-out takes eluate, dries, and obtains purified；
(3) purified is separated with preparative chromatography, obtains pinocembrin, the methoxy chalcones of 4- hydroxyls -2, the 7- of high-purity
Hydroxyl dihydro anthoxanthin, 2,4- dihydroxy-dihydrochalcone and 2,4- dihydroxy-chalcone；Chromatographic condition is as follows：
Detection wavelength：210~380nm；
Chromatographic column：C18 or C8 chromatographic columns；
Mobile phase A is methyl alcohol, and Mobile phase B is water；
Condition of gradient elution is：0~10min, 50%A → 60%A；10~40min, 60%A → 90%A.
Further, the chromatographic column is C18 chromatographic columns.
Further, the column temperature of the chromatographic condition is 20~30 DEG C.
Further, the resin is micro-porous resin or macroreticular resin
Further, the flow velocity of the chromatographic condition is 10~100mL/min.
Further, the Detection wavelength is 360nm.
Further, the falcate crazyweed herb extractive of general flavone is prepared by the following method：
(1) falcate crazyweed herb is taken, addition concentration is 70%-80% alcohols solvents, and Microwave Extraction obtains extract solution, and the alcohols is molten
Agent is 10~35 with the volume mass ratio of medicinal material:1mL/g；
(2) concentrated extracting solution, ceramic membrane filtration, organic film purifying takes filtrate, is drying to obtain.
Further, the alcohols solvent is the ethanol of concentration 75%, and the power of Microwave Extraction is 731W, and extraction time is
26 minutes, ethanol was 26 with the volume mass ratio of medicinal material:1.
Further, the methyl alcohol wash-out is to be eluted with 2~10 times of 80% methanol solutions of column volume.
Present invention also offers pinocembrin, the methoxy chalcones of 4- hydroxyls -2,7- hydroxyl dihydro anthoxanthins, 2,4- dihydroxy -
Dihydrochalcone or 2,4- dihydroxy-application of the chalcone in anti-inflammatory drug is prepared.
With falcate crazyweed herb as raw material, separation has prepared pinocembrin, the methoxy chalcones of 4- hydroxyls -2,7- hydroxyls to the present invention
Base flavanone, 2,4- dihydroxy-dihydrochalcone and 2,4- dihydroxy-chalcone, product purity are all higher than 98%.The method
Preparation amount is big, and product purity is high, is suitable for commercial Application.
Obviously, the above of the invention, according to the ordinary technical knowledge and customary means of this area, is not departing from
Under the premise of the above-mentioned basic fundamental thought of the present invention, the modification of other diversified forms can also be made, is replaced or is changed.
The specific embodiment of form, remakes further specifically to the above of the invention by the following examples
It is bright.But this scope for being interpreted as above-mentioned theme of the invention should not be only limitted to following example.It is all based on the above of the present invention
The technology realized belongs to the scope of the present invention.
Brief description of the drawings
Fig. 1 obtains compound for pinocembrin (A), the methoxy chalcones of 4- hydroxyls -2 (B), 7- to separate preparative chromatography figure
Hydroxyl dihydro anthoxanthin (C), 2,4- dihydroxy-dihydrochalcone (D), 2,4- dihydroxy-chalcone (E).
Specific embodiment
Falcate crazyweed herb picks up from Haibei Prefecture in August, 2015, through Northwest Plateau-organisms Research Inst. of Chinese Academy of Sciences grandson
Cyanines assistant researcher identifies；Rutin standard items are purchased from Chinese drug inspection office (lot number：100080-200707, content is
90.5%), it is pure that ethanol, natrium nitrosum, aluminum nitrate, NaOH are analysis.Self-control ultra-pure water.
Microwave Extraction instrument (RWBC, Nanjing Su Enrui companies) METTLER TOLEDO PL203 and XS204 electronic balances are (auspicious
Scholar Mettler Toledo Inc.)；TU-1901 type ultraviolet-uisible spectrophotometers.
Chromatogram methyl alcohol (Shandong Yu Wang companies)；Preparative chromatograph (Hanbon Sci. ＆ Tech. Co., Ltd.), ceramic membrane separation sets
Standby (Hefei Shi Jiemo Co., Ltds)；Organic membrane separation plant (Hefei Shi Jiemo Co., Ltds), petroleum ether, ethyl acetate are day
Tianjin all generations company.
The unit of solid-liquid ratio is ml/g.
Embodiment 1
1. the preparation of falcate crazyweed herb extract
Preparation method：
1) Microwave Extraction：Microwave Extraction power is 731w, and extraction time is 26min, and liquid ratio is 26, and 75% ethanol is carried
Take.
2) extract solution concentration.
3) ceramic membrane filter removal of impurities：0.1um ceramic membranes, pressure 3MPa, flow velocity 50ml is per minute, removes fine slag, soil
Deng impurity, reclaim through survey solution.
4) organic membrane separating and purifying：Use molecular weight to be purified for 2000 molecular weight organic film, pressure is 1MPa, flow
Fast 50ml is per minute, collects through survey solution.
5) microwave drying, freeze-drying, spray drying are dried.
2. extract：
After deionized water dissolving by the beans extract of sour jujube medicinal extract with 10 times of its quality, successively with petroleum ether, acetic acid second
Ester is extracted, and respectively obtains petroleum ether part, ethyl acetate extract and water position；By the ethyl acetate extract drying to perseverance
After weight, ethyl acetate extract dried powder is obtained.
3. removal of impurities
After deionized water dissolving by the ethyl acetate extract dried powder with 30 times of its quality, filtrate is filtrated to get
A, filtrate injection micro-porous resin is separated, and is eluted with the methanol solution that the volume fraction of 10 times of column volumes is 80%, and collection is washed
De- thing.After the eluate is freeze-dried, anti-inflammatory active ingredient in whin is obtained final product.
5. refine
The freeze drying example 10 times of methyl alcohol of quality dissolve, and are injected into after 0.45um micro-pore-film filtrations with preparation
In chromatogram arrangement, 0-10min, 50-60% methyl alcohol, 10-40min 60%-90% methyl alcohol wash-out, online ultraviolet detection obtain final product symbol
The compound of chemical reference substance requirement and purity ＞ 98% is closed, yield is about 70%.Result is as shown in Figure 1.
Compound is pinocembrin (A), the methoxy chalcones of 4- hydroxyls -2 (B), 7- hydroxyl dihydro anthoxanthins (C), 2,4- dihydroxies
Base-dihydrochalcone (D), 2,4- dihydroxy-chalcone (E) (significant composition).
The anti-inflammatory activity of the compound of embodiment 2
To compound pinocembrin,-the hydroxy-2 '-methoxychalcone of -2 methoxy chalcones of 4- hydroxyls 4 ', 7- hydroxyls
Base flavanone, 2,4- dihydroxy-dihydrochalcone, 2,4- dihydroxy-chalcone carry out anti-inflammatory experiment, and 5 kinds of compounds have
Preferable anti-inflammatory activity.
1 Study of cytotoxicity
The toxicity test of RAW264.7 cells, mtt assay.As a result shown in table 1~5.
Table 1
Table 2
Table 3
Table 4
Table 5
2 culture macrophage RAW264.7, detect TNF-α respectively, and the index of NO, PEG2 as a result as shown in table 6-8, is examined
Survey method sees below document：
1 single sonorous stone side, Wang Qiangsong, Cui Yuanlu, Biqi capsules extract to the antiinflammatory action of RAW264.7 cell models, it is middle into
Medicine, 2014,36 (1)：26-30.
2 Wang Juan, Jiang Wei, Wang Yi, flavone compound is to lipopolysaccharide-induced RAW264.7 cell antiinflammatory actions in dalbergia wood
Research, cell and molecular immunology magazine, 2013,29 (7)：681-684.
3 stone Meng Qiong, Qin Huilin, Zhang Yongfeng, Liu Ying, Deng Wei, Yang Wenyan, etc., pawpaw triterpene under lipopolysaccharide-induced
The influence of the RAW264.7 cellular inflammation model cell factors, Pharmacology and Clinics of Chinese Materia Medica, 2016,32 (3)：76-80.
The 4 Luo Fu tinkling of pieces of jade, Zhao Hengguang, Li Hongzhong, Wan Jingyuan, Zhou Qixin, Tet is thin to lipopolysaccharide-induced lower RAW264.7
The effect of born of the same parents' inflammatory model cell factor, Chinese herbal medicine, 2011,42 (3):542-545.
The LPS inducing cell PEG2 changes of contents of table 6
| Concentration (uM) | PEG2(pg/ml) | |
| Blank | 1633.38 | |
| LPS | 3345.28 | |
| Pinocembrin | 60 | 2639.25 |
| Pinocembrin | 30 | 2760.13 |
| Pinocembrin | 15 | 2962.62 |
| The methoxy chalcones of 4- hydroxyls -2 | 2.5 | 2829.31 |
| The methoxy chalcones of 4- hydroxyls -2 | 1.25 | 2828.11 |
| The methoxy chalcones of 4- hydroxyls -2 | 0.625 | 2972.92 |
| 7- hydroxyl dihydro anthoxanthins | 60 | 2561.09 |
| 7- hydroxyl dihydro anthoxanthins | 30 | 2842.09 |
| 7- hydroxyl dihydro anthoxanthins | 15 | 3146.89 |
| 2,4- dihydroxy-chalcone | 1 | 2356.53 |
| 2,4- dihydroxy-chalcone | 0.5 | 2970.7 |
| 2,4- dihydroxy-chalcone | 0.25 | 3167.52 |
| 2,4- dihydroxy-dihydrochalcone | 20 | 2712.24 |
| 2,4- dihydroxy-dihydrochalcone | 10 | 2829.56 |
| 2,4- dihydroxy-dihydrochalcone | 5 | 3107.04 |
The NO contents of table 7
| Concentration (uM) | PEG2(umol/L) | |
| Blank | 1.93 | |
| LPS | 6.03 | |
| Pinocembrin | 60 | 3.3 |
| Pinocembrin | 30 | 4.05 |
| Pinocembrin | 15 | 4.5 |
| The methoxy chalcones of 4- hydroxyls -2 | 2.5 | 3.56 |
| The methoxy chalcones of 4- hydroxyls -2 | 1.25 | 4.29 |
| The methoxy chalcones of 4- hydroxyls -2 | 0.625 | 5.04 |
| 7- hydroxyl dihydro anthoxanthins | 60 | 3.58 |
| 7- hydroxyl dihydro anthoxanthins | 30 | 4.64 |
| 7- hydroxyl dihydro anthoxanthins | 15 | 5.65 |
| 2,4- dihydroxy-chalcone | 1 | 2.8 |
| 2,4- dihydroxy-chalcone | 0.5 | 4.81 |
| 2,4- dihydroxy-chalcone | 0.25 | 5.39 |
| 2,4- dihydroxy-dihydrochalcone | 20 | 3.79 |
| 2,4- dihydroxy-dihydrochalcone | 10 | 4.52 |
| 2,4- dihydroxy-dihydrochalcone | 5 | 5.32 |
The TNF-α changes of contents of table 8
| Concentration (uM) | TNF-α(pg/ml) | |
| Blank | 52.37 | |
| LPS | 207.45 | |
| Pinocembrin | 60 | 122.11 |
| Pinocembrin | 30 | 129.06 |
| Pinocembrin | 15 | 151.16 |
| The methoxy chalcones of 4- hydroxyls -2 | 2.5 | 138.99 |
| The methoxy chalcones of 4- hydroxyls -2 | 1.25 | 10.48 |
| The methoxy chalcones of 4- hydroxyls -2 | 0.625 | 161.42 |
| 7- hydroxyl dihydro anthoxanthins | 60 | 113.78 |
| 7- hydroxyl dihydro anthoxanthins | 30 | 148.07 |
| 7- hydroxyl dihydro anthoxanthins | 15 | 162.27 |
| 2,4- dihydroxy-chalcone | 1 | 95.09 |
| 2,4- dihydroxy-chalcone | 0.5 | 160.24 |
| 2,4- dihydroxy-chalcone | 0.25 | 183.95 |
| 2,4- dihydroxy-dihydrochalcone | 20 | 134.61 |
| 2,4- dihydroxy-dihydrochalcone | 10 | 138.24 |
| 2,4- dihydroxy-dihydrochalcone | 5 | 169.66 |
Falcate crazyweed herb has antiinflammatory action, and to so far, reactive compound is separated in rare document report falcate crazyweed herb
Prepare, the inventive method carries out separation preparation to antiinflammatory active compound in falcate crazyweed herb using preparative chromatograph, and obtains pure
Degree compound higher, and cytoactive experiment is further carried out to compound, isolated compound is mainly by suppressing
Inflammatory factor NO, TNF-α etc. discharge, and inhibitory action are directly played, so as to show antiinflammatory action.The inventive method is easy to be real
With for the anti-inflammatory substance basis of falcate crazyweed herb provides theoretical foundation, while being supported for pharmaceutical production also provides data.
Claims (10)
1. a kind of separation from falcate crazyweed herb prepares 5 kinds of methods with antiinflammatory active compound, it is characterised in that：Described 5 kinds
Be pinocembrin with antiinflammatory active compound, the methoxy chalcones of 4- hydroxyls -2,7- hydroxyl dihydro anthoxanthins, 2,4- dihydroxy -
Dihydrochalcone and 2,4- dihydroxy-chalcone, comprise the following steps：
(1) falcate crazyweed herb extractive of general flavone is taken, is extracted with petroleum ether and ethyl acetate successively, take ethyl acetate extract；
(2) ethyl acetate extract dried powder is taken, purifying resin, methyl alcohol wash-out takes eluate, dries, and obtains purified；
(3) purified is separated with preparative chromatography, obtains pinocembrin, the methoxy chalcones of 4- hydroxyls -2, the 7- hydroxyls of high-purity
Flavanone, 2,4- dihydroxy-dihydrochalcone and 2,4- dihydroxy-chalcone；Chromatographic condition is as follows：
Detection wavelength：210~380nm；
Chromatographic column：C18 or C8 chromatographic columns；
Mobile phase A is methyl alcohol, and Mobile phase B is water；
Condition of gradient elution is：0~10min, 50%A → 60%A；10~40min, 60%A → 90%A.
2. method according to claim 1, it is characterised in that：The chromatographic column is C18 chromatographic columns.
3. method according to claim 1, it is characterised in that：The column temperature of the chromatographic condition is 20~30 DEG C.
4. method according to claim 1, it is characterised in that：The resin is micro-porous resin or macroreticular resin.
5. method according to claim 1, it is characterised in that：The flow velocity of the chromatographic condition is 10~100mL/min.
6. method according to claim 1, it is characterised in that：The Detection wavelength is 360nm.
7. the method according to claim any one of 1-4, it is characterised in that：The falcate crazyweed herb extractive of general flavone is logical
Cross what following methods were prepared：
(1) take falcate crazyweed herb, addition concentration is 70%-80% alcohols solvents, Microwave Extraction obtains extract solution, the alcohols solvent with
The volume mass ratio of medicinal material is 10~35:1mL/g；
(2) concentrated extracting solution, ceramic membrane filtration, organic film purifying takes filtrate, is drying to obtain.
8. method according to claim 7, it is characterised in that：The alcohols solvent is the ethanol of concentration 75%, and microwave is carried
The power for taking is 731W, and extraction time is 26 minutes, and ethanol is 26 with the volume mass ratio of medicinal material:1mL/g.
9. the method according to claim any one of 1-8, it is characterised in that：The methyl alcohol wash-out is with 2~10 times of cylinders
Long-pending 80% methanol solution wash-out.
10. pinocembrin, the methoxy chalcones of 4- hydroxyls -2,7- hydroxyl dihydro anthoxanthins, 2,4- dihydroxy-dihydrochalcone or 2,4-
Application of the dihydroxy-chalcone in anti-inflammatory drug is prepared.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108659073A (en) * | 2018-04-28 | 2018-10-16 | 中国科学院西北高原生物研究所 | A kind of method and application thereof preparing six kinds of compounds of oxytroflavoside from falcate crazyweed herb |
| CN110917236A (en) * | 2020-01-07 | 2020-03-27 | 四川农业大学 | Oxytropis falcate anti-fungal infection extract and preparation method and application thereof |
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| JP2008106011A (en) * | 2006-10-26 | 2008-05-08 | National Institute Of Advanced Industrial & Technology | Inflammatory cytokine production inhibitor |
| WO2013038136A1 (en) * | 2011-09-16 | 2013-03-21 | The University Of Surrey | BI-AROMATIC AND TRI-AROMATIC COMPOUNDS AS NADPH OXIDASE 2 (Nox2) INHIBITORS |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108659073A (en) * | 2018-04-28 | 2018-10-16 | 中国科学院西北高原生物研究所 | A kind of method and application thereof preparing six kinds of compounds of oxytroflavoside from falcate crazyweed herb |
| CN108659073B (en) * | 2018-04-28 | 2021-03-23 | 中国科学院西北高原生物研究所 | Method for preparing oxytrofloxacin six compounds from Oxytropis falcate and application thereof |
| CN110917236A (en) * | 2020-01-07 | 2020-03-27 | 四川农业大学 | Oxytropis falcate anti-fungal infection extract and preparation method and application thereof |
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