CN106916193A - A kind of method that afzclin is extracted in the leaf from cercis - Google Patents
A kind of method that afzclin is extracted in the leaf from cercis Download PDFInfo
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- CN106916193A CN106916193A CN201710206992.7A CN201710206992A CN106916193A CN 106916193 A CN106916193 A CN 106916193A CN 201710206992 A CN201710206992 A CN 201710206992A CN 106916193 A CN106916193 A CN 106916193A
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- afzclin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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Abstract
A kind of method the invention discloses afzclin is extracted in leaf from cercis, comprises the following steps：With dry cercis leaf as raw material, with 70% ethanol, 50 DEG C of extractions after crushing, extract solution is recovered under reduced pressure solvent and obtains extract medicinal extract；After extract medicinal extract is dissolved in water, after the macroporous resin column loadings of D 101, different concentration ethanol gradient elution is used, obtain corresponding elution fraction；Post will be filled after 40% ethanol elution part silica gel mixed sample, eluted with dichloromethane and methyl alcohol, thin layer detection, merging identical point carries out that solvent is recovered under reduced pressure, and obtains crude product；By dissolving crude product, the gel chromatographic columnses of LH 20 are crossed, methyl alcohol wash-out obtains afzclin sterling.A kind of method the invention provides separation afzclin is extracted in cercis leaf, is conducive to preferably this medicinal plant of exploitation cercis, is conducive to the sustainable use of plant；Extraction process of the present invention is simple, is easy to get to afzclin monomer, and solvent recoverable, extracted amount greatly, can industrialized production.
Description
Technical field
The invention belongs to technical field of plant extraction, and in particular to a kind of method that afzclin is extracted in leaf from cercis.
Background technology
Cercis（Mitragyna rotundifolia Kuntze.）It is pulse family section（Rubiaceae）Redbud
（Mitragyna L.）Plant.Bark and timber can be used as medicine, clearing heat and detoxicating with blood-activating and qi-promoting, the effects such as swelling and pain relieving, cercis
Flower can be used to treat infantile malnutrition due to digestive disturbances or intestinalparasites sore in treating rheumatic ostealgia, nose；Fruit of Chinese redbud can treat cough.
Native compound afzclin system involved in the present invention obtains from Redbud in plant cercis first, category
In one kind of flavonoid drugs.Afzclin abundance, is present in various plants, and modern pharmacology research shows it
To ovalbumin induction pneumonia of rats play the role of inhibitory action, with anti-oxidant and liver protection.Research discovery, A Fu beans recently
Glycosides also has preferable antithrombotic acitivity, can further be researched and developed as antithrombotic drug candidate.As can be seen here, A Fu beans
Glycosides has bright prospects, although afzclin has high level in cercis leaf, but has not yet to see a large amount of from redbud
Extract the report of afzclin.
The content of the invention
Based on the deficiencies in the prior art, it is an object of the invention to provide the side that afzclin is extracted in a kind of leaf from cercis
Method.
To achieve these goals, the technical solution adopted by the present invention is：
A kind of method that afzclin is extracted in leaf from cercis, comprises the following steps：
（1）With dry cercis leaf as raw material, 2 ~ 4 times, every time 2.5 ~ 3.5 are extracted in 45 ~ 55 DEG C with 65 ~ 75% ethanol after crushing
H, merges extract solution, solvent is recovered under reduced pressure and obtains extract medicinal extract；Extract medicinal extract is dissolved in water, macroporous resin column loading
Afterwards, corresponding elution fraction is obtained with 20% ethanol, 40% ethanol, 60% ethanol and 90% ethanol gradient elution successively；
（2）By step（1）Compare 1 according to weight with 60 ~ 100 mesh silica gel in the ethanol elution part of gained 40%：29 ~ 31 mix sample after fill post,
Dichloromethane is with methyl alcohol according to volume ratio 9 ~ 10：1 wash-out, thin layer detection, merging identical point carries out that solvent, get A Fu is recovered under reduced pressure
Beans glycosides crude product.
Further, by step（2）Gained afzclin crude methanol dissolves, and crosses Sephadex LH-20 gel chromatographic columnses,
Methyl alcohol is eluted, and obtains afzclin sterling.
Afzclin molecular formula of the present invention：C21H20O10, molecular weight：432, its structural formula is as follows：
Beneficial effects of the present invention：
（1）Up to the present, there is not yet extracting the report of afzclin from cercis, the invention provides being carried in a kind of cercis leaf
The method for separating afzclin is taken, is conducive to preferably this medicinal plant of exploitation cercis.
（2）It is a large amount of from cercis leaf to extract the sustainable use that afzclin is more beneficial for plant.
（3）The present invention extracts the compound afzclin for obtaining extensive bioactivity, and has abundant raw material sources；
The invention provides a kind of extracting method, it is easy to carry out in-depth study to it.
（3）Extraction process of the present invention is simple, is easy to get to afzclin monomer, and solvent recoverable, extracted amount greatly, can work
Industry metaplasia is produced.
Specific embodiment
In order that technical purpose of the invention, technical scheme and beneficial effect are clearer, with reference to specific embodiment
Technical scheme is further illustrated, but the embodiment is intended to explain the present invention, and it is not intended that right
Limitation of the invention, in the examples where no specific technique or condition is specified, according to the technology described by document in the art or
Condition is carried out according to product description.
In following embodiments, Huangchuan County of Henan Province cercis planting base is collected in as the cercis leaf of raw material；The ethanol,
Methanol concentration is volumetric concentration.
Embodiment 1
A kind of method that afzclin is extracted in leaf from cercis, comprises the following steps：
（1）It is raw material by the dry cercis leaves of 4.5 kg, 70% ethanol is used after crushing（The consumption 25L of 70% ethanol）, 50 DEG C extract 3
Secondary, 3 h, merges extract solution every time, solvent is recovered under reduced pressure and obtains extract medicinal extract；Extract medicinal extract is dissolved in water, D-101 is big
After the resin column loading of hole, successively with 20% ethanol, 40% ethanol, 60% ethanol and 90% ethanol gradient elution, accordingly wash-out portion is obtained
Point；
（2）By step（1）Compare 1 according to weight with 60 mesh silica gel in the ethanol elution part of gained 40%：30 mix sample after fill post, dichloromethane
Alkane is with methyl alcohol according to volume ratio 10：1 wash-out, thin layer detection, merging identical point carries out that solvent is recovered under reduced pressure, and obtains afzclin thick
Product；
（3）By step（2）Gained afzclin crude product methyl alcohol dissolves, and crosses Sephadex LH-20 gel chromatographic columnses, 100% first
Alcohol is eluted, and obtains afzclin sterling.
Afzclin sterling proterties obtained above is crystallized in yellow particle shape, and yield is 0.022%.
Structure is identified with various spectroscopy techniques to afzclin sterling obtained above, it is specific as follows：
Instrument material：It is ultraviolet to be determined on UV-210A ultraviolet spectroscopy instrument；1H, 13C NMR collection of illustrative plates are by Bruker am-
400 MHz nmr determinations.TMS is internal standard；Two dimensional NMR collection of illustrative plates is surveyed by DRX-500 MHz NMRs
It is fixed；Mass spectrum is determined by VG.AUTO Spec-3000 types mass spectrograph.
Experimental result：EI-MS m/z: 432[M]+ 1H-NMR(DMSO-d6, 400 MHz) δ:12.62 (1H, s),
10.27 (1H, s), 7.75 (2H, d, H-2', H-6'), 6.91 (2H, d, H-3', H-5'), 6.41 (1H,
d, H-8), 6.21 (1H, d, H-6), 5.29 (1H, s, H-1''), 0.79 (3H, s, H-6''). 13C-NMR
(DMSO-d6,100 MHz) δ:177.76 (C-4), 164.30 (C-7), 161.33 (C-5), 160.04 (C-4'),
157.30 (C-9), 156.55 (C-2), 134.84 (C-3), 130.66 (C-2', C-6'), 120.56 (C-1'),
115.44 (C-3', C-5'), 104.17 (C-10), 101.81 (C-1''), 98.78 (C-6), 93.81 (C-8),
71.15 (C-4''), 70.68 (C-3''), 70.35 (C-5''), 70.12 (C-2''), 17.51 (C-6'')。
Check：It is in hyperfluorescence in UV 254nm using TLC；Sulfuric acid chromogenic reagent, 5 minutes at 110 DEG C, is presented yellow.
Assay：Using HPLC, chromatographic condition：Agilent SB-C18 chromatographic columns；Mobile phase is methyl alcohol：Water（30：70
~90：10）, flow velocity：0.8mL/min, Detection wavelength 254nm, the min of retention time value 32.4.After testing, purity >=99%.
Embodiment 2
A kind of method that afzclin is extracted in leaf from cercis, comprises the following steps：
（1）With dry cercis leaf as raw material, with the extraction 2 times of 55 DEG C of 65% ethanol after crushing, 3.5 h, merges extract solution every time,
Solvent is recovered under reduced pressure and obtains extract medicinal extract；Extract medicinal extract is dissolved in water, after D-101 macroporous resin column loadings, is used successively
20% ethanol, 40% ethanol, 60% ethanol and 90% ethanol gradient elution, obtain corresponding elution fraction；
（2）By step（1）Compare 1 according to weight with 80 mesh silica gel in the ethanol elution part of gained 40%：29 mix sample after fill post, dichloromethane
Alkane is with methyl alcohol according to volume ratio 9：1 wash-out, thin layer detection, merging identical point carries out that solvent is recovered under reduced pressure, and obtains afzclin crude product；
（3）By step（2）Gained afzclin crude product methyl alcohol dissolves, and crosses Sephadex LH-20 gel chromatographic columnses, 100% first
Alcohol is eluted, and obtains afzclin sterling.
Afzclin sterling proterties obtained above is crystallized in yellow particle shape, and yield is 0.020%, purity >=99%.
Embodiment 3
A kind of method that afzclin is extracted in leaf from cercis, comprises the following steps：
（1）With dry cercis leaf as raw material, with the extraction 4 times of 45 DEG C of 75% ethanol after crushing, 2.5 h, merges extract solution every time,
Solvent is recovered under reduced pressure and obtains extract medicinal extract；Extract medicinal extract is dissolved in water, after D-101 macroporous resin column loadings, is used successively
20% ethanol, 40% ethanol, 60% ethanol and 90% ethanol gradient elution, obtain corresponding elution fraction；
（2）By step（1）Compare 1 according to weight with 100 mesh silica gel in the ethanol elution part of gained 40%：31 mix sample after fill post, dichloromethane
Alkane is with methyl alcohol according to volume ratio 10：1 wash-out, thin layer detection, merging identical point carries out that solvent is recovered under reduced pressure, and obtains afzclin thick
Product；
（3）By step（2）Gained afzclin crude product methyl alcohol dissolves, and crosses Sephadex LH-20 gel chromatographic columnses, 100% first
Alcohol is eluted, and obtains afzclin sterling.
Afzclin sterling proterties obtained above is crystallized in yellow particle shape, and yield is 0.021%, purity >=99%.
Claims (2)
1. a kind of method that afzclin is extracted in leaf from cercis, it is characterised in that comprise the following steps：
（1）With dry cercis leaf as raw material, 2 ~ 4 times, every time 2.5 ~ 3.5 are extracted in 45 ~ 55 DEG C with 65% ~ 75% ethanol after crushing
H, merges extract solution, solvent is recovered under reduced pressure and obtains extract medicinal extract；Extract medicinal extract is dissolved in water, macroporous resin column loading
Afterwards, corresponding elution fraction is obtained with 20% ethanol, 40% ethanol, 60% ethanol and 90% ethanol gradient elution successively；
（2）By step（1）Compare 1 according to weight with 60 ~ 100 mesh silica gel in the ethanol elution part of gained 40%：29 ~ 31 mix sample after fill post,
Dichloromethane is with methyl alcohol according to volume ratio 9 ~ 10：1 wash-out, thin layer detection, merging identical point carries out that solvent, get A Fu is recovered under reduced pressure
Beans glycosides crude product.
2. the method for extracting afzclin from cercis leaf according to claim 1, it is characterised in that：By step（2）Gained
Afzclin crude methanol dissolves, and crosses Sephadex LH-20 gel chromatographic columnses, and methyl alcohol wash-out obtains afzclin sterling.
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| CN201710206992.7A CN106916193B (en) | 2017-03-31 | 2017-03-31 | A method of extracting afzclin from cercis leaf |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107987112A (en) * | 2018-01-17 | 2018-05-04 | 天津科技大学 | A kind of preparation method of afzclin derivative |
| CN108218935A (en) * | 2018-02-06 | 2018-06-29 | 河南大学 | The method for extracting myricetrin, quercitin and afzclin from cercis leaf using ionic liquid |
| CN108578461A (en) * | 2018-01-22 | 2018-09-28 | 河南大学 | Cercis extract and its extracting method and the application in terms of preparing antithrombotic reagent |
| CN113717140A (en) * | 2021-10-11 | 2021-11-30 | 许昌学院 | Method for preparing quercetin and kaempferol-3-O-rutinoside from folium Cercis chinensis extract |
| CN114105929A (en) * | 2021-10-11 | 2022-03-01 | 河南大学 | Method for preparing kaempferol and afzerin from Chinese redbud leaf extract |
-
2017
- 2017-03-31 CN CN201710206992.7A patent/CN106916193B/en active Active
Non-Patent Citations (2)
| Title |
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| 催莹: "寸节七化学成分研究", 《中草药》 * |
| 谭鸣鸿 等: "紫荆花化学成分的研究（I）", 《中草药》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107987112A (en) * | 2018-01-17 | 2018-05-04 | 天津科技大学 | A kind of preparation method of afzclin derivative |
| CN107987112B (en) * | 2018-01-17 | 2020-11-03 | 天津科技大学 | Preparation method of afzelin derivative |
| CN108578461A (en) * | 2018-01-22 | 2018-09-28 | 河南大学 | Cercis extract and its extracting method and the application in terms of preparing antithrombotic reagent |
| CN108218935A (en) * | 2018-02-06 | 2018-06-29 | 河南大学 | The method for extracting myricetrin, quercitin and afzclin from cercis leaf using ionic liquid |
| CN108218935B (en) * | 2018-02-06 | 2020-11-03 | 河南大学 | Method for extracting myricitrin, quercitrin and afzelin from Chinese redbud leaves by using ionic liquid |
| CN113717140A (en) * | 2021-10-11 | 2021-11-30 | 许昌学院 | Method for preparing quercetin and kaempferol-3-O-rutinoside from folium Cercis chinensis extract |
| CN114105929A (en) * | 2021-10-11 | 2022-03-01 | 河南大学 | Method for preparing kaempferol and afzerin from Chinese redbud leaf extract |
| CN113717140B (en) * | 2021-10-11 | 2023-03-24 | 许昌学院 | Method for preparing quercetin and kaempferol-3-O-rutinoside from folium Cercis chinensis extract |
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