CN104311616B - A kind of extraction high purity cortex fraxini and method of fraxin from Cortex Fraxini - Google Patents
A kind of extraction high purity cortex fraxini and method of fraxin from Cortex Fraxini Download PDFInfo
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- CN104311616B CN104311616B CN201410519725.1A CN201410519725A CN104311616B CN 104311616 B CN104311616 B CN 104311616B CN 201410519725 A CN201410519725 A CN 201410519725A CN 104311616 B CN104311616 B CN 104311616B
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- 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
- C07H17/075—Benzo[b]pyran-2-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
The invention provides a kind of extraction high purity cortex fraxini and method of fraxin from Cortex Fraxini.Use conventional method pulverize Cortex Fraxini raw material and circumfluence distillation, prepare aqueous two-phase, dissolve, extract, concentrate, desalination, crystallisation step.Key step includes: 1) prepare double-aqueous phase system, standby after separating upper and lower phase, dissolves Cortex Fraxini extract with phase solvent；2) after being centrifuged or filter the above-mentioned solution containing Cortex Fraxini extract, add appropriate lower phase solvent, it is thoroughly mixed, stand, the upper phase solution of isolated concentrates, inorganic matter in Cortex Fraxini extract, monosaccharide, polysaccharide and the solid impurity such as vegetable protein, chlorophyll be can effectively remove, aseculin and the content of fraxin improved.The solution that above-mentioned steps obtains, after the impurity such as conventional method desalination, is concentrated into suitable concn, can successively obtain aseculin and fraxin crystallization.Instant invention overcomes and from Cortex Fraxini, prepare at present aseculin and fraxin exists is difficult to crystallization or the problem such as production cost is high, operation is complicated, there is the features such as simple, the environmental protection of production equipment.
Description
Technical field
The present invention relates to the aqueous two-phase that a kind of organic solvent using inorganic salt/energy miscible with water is formed
Aseculin in the upper and lower phase solution dissolving of system, extraction Cortex Fraxini extract and the side of fraxin
Method, belongs to technical field of biochemical industry.
Background technology
At present, the main uses of highly purified aseculin has 1. as biochemistry detection reagent: utilize
The structure enzyme of the antibacterial that some metabolism is active can quickly make aseculin hydrolysis generate aesculetin and Portugal
Grape sugar, the aesculetin of generation can decompose product with ferric ammonium citrate in culture medium or ferric citrate again
Raw Fe2+Reaction, generates black-and-blue material, makes culture medium present black-and-blue speckle, can be straight with this
See, differentiate accurately the kind of some oxygen-containing antibacterial, can be able to draw in 15 30 minutes the soonest
Testing result, compared with traditional general culture method detection using microorganism, is a kind of novel
Microbial check reagent fast and effectively.2. can play in the cosmetics whitening, sun-proof,
The effect of antiperspirant, as important natural cosmetics raw material, existing century-old applicating history.
It addition, aseculin, fraxin to be formed with eye drop, oral cavity as main matter basis clear
Lotions etc. are applied to health regulation.
At present, separate from Cortex Fraxini and prepare the method for highly purified aseculin and fraxin and can divide
Two kinds of methods are extracted for column chromatography and organic solvent.Wherein the form of column chromatography mainly has: " from
The method of isolated and purified monomeric compound in Barks of Fraxinus chinensis Roxb " (Chinese patent CN102924416B) carry
The employing gel filtration filler Superose 12 gone out is carrier of separating, and the methanol-water with 10 80% is
Eluent, fraction collection target components, through being concentrated to give aseculin, the Cortex Fraxini of more than 98%
B prime, fraxin and fraxetin.It addition, " high purity cortex fraxini and preparation method thereof " (China
Patent CN1955173B) propose to use macroporous resin for absorption and carrier of separating, with deionized water be
Eluant, after being washed till clarification, collects the eluting solution of 10～15 times of column volumes, concentrates, filter,
Recrystallization can get the aseculin of purity more than 97%.Said method uses gel and macroporous resin
As carrier of separating, production cost is high, and the adsorbance of carrier is limited, the pre-treatment of carrier and use
After Regeneration Treatment complicated, after being used for multiple times, its adsorbance necessarily declines, and process repeatability is poor, no
It is beneficial to being carried out continuously of operation and prepares aseculin and fraxin with scale.Organic solvent extractionprocess
Implementation process be to use chloroform extraction to remove the liposoluble such as the resin in Cortex Fraxini extracting solution, chlorophyll
Property impurity after, then be extracted with ethyl acetate the removing impurity such as aesculetin therein, concentrate through 2
The Cortex Fraxini extract liquid that secondary extraction processes, to suitable volumes, is placed, and crystallizes or is recrystallized to give the Qin
Leather armour element.The subject matter that the method is primarily present is, many containing a large amount of plants in solution to be crystallized
Sugar and monosaccharide, albumen etc., viscosity is high, is difficult to crystallization.
Therefore, exist during this area needs a kind of production that can overcome existing aseculin and fraxin
Problems, production cost can be reduced, it is easy to large-scale production, the height of environmentally friendly type
Purity aseculin and the method for fraxin.
Summary of the invention
It is an object of the invention to provide a kind of extraction high purity cortex fraxini and fraxin from Cortex Fraxini
Method, the method is easily operated and large-scale production, have that production cost is low, equipment simple,
The features such as environmental protection.
The invention provides a kind of extraction high purity cortex fraxini and method of fraxin from Cortex Fraxini,
It is characterized in that comprising the following steps:
(1) methanol or water conventional method is used to obtain the different quality containing aseculin, fraxin etc. dense
The Cortex Fraxini extract of degree；
(2) double-aqueous phase system is prepared, and the upper and lower phase solution of isolated aqueous two-phase, use
Phase solution dissolves Cortex Fraxini extract repeatedly, does not contains aseculin and fraxin to Cortex Fraxini extract
Till；
(3), after being centrifuged or filter the above-mentioned solution containing aseculin and fraxin, add above-mentioned molten
The lower phase solution of liquid 1～3 times amount, fully extracts, and the solid content impurity ratio in supreme phase is the brightest
Till aobvious minimizing, the upper phase solution of isolated, it is concentrated to give main containing aseculin and fraxin
Solution；
(4), after using conventional means desalination and oil-soluble impurities composition, concentrate, crystallize obtain high-purity
Degree aseculin and fraxin.
Described double-aqueous phase system uses Na2HPO4、(NH4)2SO4、K2HPO4And can be formed double
The inorganic salt of aqueous phase prepares gained.
Organic solvent in described double-aqueous phase system is methanol, ethanol.
The solution temperature of described double-aqueous phase system is 20 °～30 DEG C.
Indication Cortex Fraxini of the present invention, refers to the certified products Cortex Fraxini medical material (bag specified with version Chinese Pharmacopoeia in 2010
Include Oleaceae fraxinus rhynchophylla Hance Fraxinus rhynchophylla Hance, Chinese ash Fraxinus
Chinensis Roxb., point leaf Chinese ash Fraxinus szaboana Lingelsh. or place post Chinese ash
Fraxinus stylosa Lingelsh.) and lanceolata Chinese ash Fraxinus baroniana Diels, lobule
The dry branch skin of Chinese ash Fraxinus bungeana DC. or dried bark.And as raw material, often
Rule method such as methanol, ethanol, water pass through through reflux, extract, the fluid extract of concentration or extractum and dust
The mass concentration of the powder etc. obtained, aseculin and fraxin is typically respectively 5%～30% He
3%～about 20%.
In said extracted thing, principle active component includes aseculin (Esculin), aesculetin
The Coumarins composition such as (Aesculetin), fraxin (Fraxin), fraxetin (Fraxetin),
And substantial amounts of chlorophyll, saccharide and resin etc., wherein aseculin and the chemical constitution of fraxin
Formula is as follows:
Extraction and crystallisation step in the inventive method belong to conventional method in the art.
Such as, described extraction step can be carried out as follows: the Cortex Fraxini coarse powder after pulverizing is extremely
In reflux, extract, tank, with the water of raw material weight 5 times amount or methanol as Extraction solvent, backflow carries
After taking 3 hours, release and be filtrated to get extracting solution, normal pressure or be concentrated in vacuo to proportion 1.10～1.20
Concentrated extract.
Such as, described crystallisation step can be carried out as follows: after treatment containing Cortex Fraxini
After the upper phase solution of A prime and fraxin concentrates, use conventional method, as added to certain density
After organic solvent desalination, it is concentrated into suitable volumes, adds aseculin crystal seed, crystallize, obtain the Qin
Leather armour element crude product, adds a small amount of ethanol in mother solution, place, crystallize, obtain fraxin crude product,
The two i.e. can get more than 98% aseculin and fraxin product again with ethyl alcohol recrystallization.
The present invention uses the conventional organic solvent such as inorganic salt with low cost and ethanol to prepare aqueous two-phase body
System, separates phase solution up and down and is easily controlled as dissolution solvent and extractant, production scale, raw
Produce low cost, it is easy to crystallization obtains target component.
The present invention can effectively remove inorganic matter in Cortex Fraxini extract, monosaccharide, polysaccharide and vegetable protein,
The solid impurities such as chlorophyll, improve aseculin and the content of fraxin.
The present invention uses the cheap chemical industry adjuvant being easy to get, through dissolving, extracting and routine operation, i.e.
Highly purified aseculin and the scale of two kinds of natural products of fraxin can be obtained from Cortex Fraxini simultaneously
Production technology, easy and simple to handle, technological process is short, can effectively reduce production cost and production difficulty.
It addition, the present invention mainly uses, people and the inorganic salt of production environment nonhazardous and organic reagent are made
For extracting carrier, production scale easily controls.The mode of production using liquid-liquid extraction makes target component
Losing little, product yield is high.
Accompanying drawing explanation
Fig. 1 is the HPLC collection of illustrative plates of Cortex Fraxini raw material.
Fig. 2 is the aseculin HPLC collection of illustrative plates that embodiment obtains.
Fig. 3 is the fraxin HPLC collection of illustrative plates that embodiment obtains.
Detailed description of the invention
Below in conjunction with example, the invention will be further described.TLC and HPLC detection method in example
See Chen Dechang chief editor " traditional Chinese chemical contrast service manual " (China Medical Science Press,
2000, P129 130).
Take Cortex Fraxini medical material (place of production: Shaanxi) 1 kilogram, be ground into coarse powder, add 6 kg ethanol,
It is heated to reflux 1 hour, leaches solution；Add 4 kg ethanol to be heated to reflux 1 hour, leach
Solution, merges twice gained extracting solution, and concentrating under reduced pressure reclaims ethanol, obtains the leaching that proportion is 1.15
Cream, standby.
Keep ambient temperature 20 DEG C, with ammonium sulfate, ethanol, water prepare double-aqueous phase system (ammonium sulfate,
Ethanol mass concentration in system is respectively 14% and 30%), after being sufficiently mixed, stand to up and down
Phase volume, without significant change, separates upper and lower phase solution, standby.
Use a small amount of mode repeatedly, fully dissolve extractum with phase solution on above-mentioned gained, use TLC
Or HPLC detection, in extractum without obvious aseculin, testing result as shown in Figure 1, Figure 2 and
Shown in Fig. 3.Merging above-mentioned solution, totally 4.2 liters, being separately added into phase solution under 0.5 liter, to extract this molten
Liquid 2 times, till in supreme phase solution, solid impurity ratio no longer significantly reduces.Isolate phase to contain
There is the solution of aseculin and fraxin, be evaporated to 0.2 liter, add ethanol to alcohol content 90%
Above, removing inorganic salt, then concentrating under reduced pressure removes ethanol, gained solution adds suitable quantity of water and heats
Dissolve, stand, crystallize, filter, obtain aseculin crude product 16.8g, with ethyl alcohol recrystallization, obtain
To the white aseculin 8.6g that purity is 98.6%；Above-mentioned mother solution is again concentrated to the 1/2 of original volume,
Add the crystallization of trace fraxin and a small amount of ethanol, again place, crystallize, filter, obtain 6.8g pure
Degree is the faint yellow fraxin acicular crystal of 98.2%.
Claims (4)
1. one kind is extracted high purity cortex fraxini and the method for fraxin from Cortex Fraxini, it is characterised in that
Comprise the following steps:
(1) methanol or water conventional method is used to obtain containing aseculin, fraxin Cortex Fraxini raw material
The Cortex Fraxini extract of different quality concentration；Described Cortex Fraxini raw material includes version Chinese Pharmacopoeia in 2010
Regulation certified products Cortex Fraxini medical material, lanceolata Chinese ash, Fraxinus bungeana and other contain Cortex Fraxini
The dry branch skin of the Oleaceae plants of A prime and fraxin or dried bark；Wherein aseculin and Cortex Fraxini
The mass concentration of glycosides is respectively 5%～30% and 3%～20%；
(2) double-aqueous phase system is prepared, and the upper and lower phase solution of isolated aqueous two-phase,
Repeatedly dissolve Cortex Fraxini extract with phase solution, do not contain to Cortex Fraxini extract aseculin and
Till fraxin；
(3) after being centrifuged or filter the above-mentioned solution containing aseculin and fraxin, in addition
State the lower phase solution of solution 1～3 times amount, fully extract, the solid content impurity ratio in supreme phase
Till example no longer significantly reduces, the upper phase solution of isolated, it is concentrated to give the main first Han Cortex Fraxini
Element and the solution of fraxin；
(4), after using conventional means desalination and oil-soluble impurities composition, condensing crystallizing obtains high-purity
Degree aseculin and fraxin.
2. extraction high purity cortex fraxini and the side of fraxin from Cortex Fraxini as claimed in claim 1
Method, it is characterised in that described double-aqueous phase system uses Na2HPO4、(NH4)2SO4、K2HPO4And
The inorganic salt that can form aqueous two-phase prepares gained.
3. extraction high purity cortex fraxini and the side of fraxin from Cortex Fraxini as claimed in claim 1
Method, it is characterised in that the organic solvent in described double-aqueous phase system is methanol, ethanol.
4. extraction high purity cortex fraxini and the side of fraxin from Cortex Fraxini as claimed in claim 1
Method, it is characterised in that the solution temperature of described double-aqueous phase system is 20 °～30 DEG C.
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| KR102021281B1 (en) * | 2018-05-25 | 2019-09-16 | 한국 한의학 연구원 | Composition for preventing, ameliorating or treating depression and anxiety disorders comprising fraxin as effective component |
| CN109134562A (en) * | 2018-10-26 | 2019-01-04 | 宁县恒瑞康生物科技有限公司 | A kind of aesculin purification process |
| CN111662345B (en) * | 2020-05-14 | 2021-04-06 | 温州医科大学 | Method for extracting chicory glycoside from Fraxinus chinensis Franch leaves |
| CN114767737B (en) * | 2022-06-21 | 2022-11-29 | 上海中医药大学 | Cortex fraxini extract, preparation method and application thereof |
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| CN1923194A (en) * | 2005-09-01 | 2007-03-07 | 成都恩威药业有限公司 | Preparation method and application of cortex fraxini extract |
| CN102091132A (en) * | 2011-01-25 | 2011-06-15 | 西南民族大学 | Method for detecting esculin, aesculetin, fraxin and fraxetin in cortex fraxini or extract thereof |
| CN102924416A (en) * | 2012-11-05 | 2013-02-13 | 聊城大学 | Method for separating and purifying monomeric compounds from ash bark |
| CN103558324A (en) * | 2013-10-25 | 2014-02-05 | 齐齐哈尔大学 | Method for extracting and identifying aesculin, fraxin, fraxetin and resveratrol from ledum palustre l.var.angustum e.busch |
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Patent Citations (4)
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| CN1923194A (en) * | 2005-09-01 | 2007-03-07 | 成都恩威药业有限公司 | Preparation method and application of cortex fraxini extract |
| CN102091132A (en) * | 2011-01-25 | 2011-06-15 | 西南民族大学 | Method for detecting esculin, aesculetin, fraxin and fraxetin in cortex fraxini or extract thereof |
| CN102924416A (en) * | 2012-11-05 | 2013-02-13 | 聊城大学 | Method for separating and purifying monomeric compounds from ash bark |
| CN103558324A (en) * | 2013-10-25 | 2014-02-05 | 齐齐哈尔大学 | Method for extracting and identifying aesculin, fraxin, fraxetin and resveratrol from ledum palustre l.var.angustum e.busch |
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