CN104497092B - A kind of method extracting 23-alisol acetyl C from Rhizoma Alismatis - Google Patents
A kind of method extracting 23-alisol acetyl C from Rhizoma Alismatis Download PDFInfo
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- CN104497092B CN104497092B CN201410817488.7A CN201410817488A CN104497092B CN 104497092 B CN104497092 B CN 104497092B CN 201410817488 A CN201410817488 A CN 201410817488A CN 104497092 B CN104497092 B CN 104497092B
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- C07—ORGANIC CHEMISTRY
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- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
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Abstract
The present invention provides a kind of method extracting 23 alisol acetyl C from Rhizoma Alismatis, mainly solves operation complexity in prior art, and product content is low, and the response rate is low.The method that should extract 23 alisol acetyl C from Rhizoma Alismatis comprises the following steps: 1] extract；2] membrance separation；3] remove impurity；4] crystallization.The method that should extract 23 alisol acetyl C from Rhizoma Alismatis uses aqueous alkali moistening, can be removed by the impurity molecule of big for part polarity；Simple to operate, product content is high, and the response rate is high, is suitable for industrialized production.
Description
Technical field
The invention belongs to Rhizoma Alismatis and extract separation field, relate to a kind of method extracting triterpenoid compound, be specifically related to one
Plant the method extracting 23-alisol acetyl C from Rhizoma Alismatis.
Background technology
Rhizoma Alismatis derives from the dry tuber of Notes On Alism At Aceae Rhizoma Alismatis, has effect of heat clearing away, diuresis.For dysuria,
Edema distension, oliguria of having loose bowels, dizziness due to fluid-retention, the puckery pain of pyretic stranguria, hyperlipidemia, be a kind of clinical practice Chinese medicine widely.Pool
The chemical composition rushed down is based on triterpenes components, and 23-alisol acetyl C, as one of main active component, studies about it
That reports is fewer, so finding the process route of an applicable industrialized production to be particularly important.
Application No. 201010554160.2, about the preparation method of a kind of alisol C monoacetic ester, proposes in technique to adopt
With microwave extracting apparatus carries out microwave extracting, and multi-stage counter current extraction and absorption with macroporous adsorbent resin, silica gel column chromatography, first
Alcohol crystallizing and drying obtains.
Summary of the invention
In order to solve the technical problem in the presence of background technology, the present invention proposes a kind of to extract 23-acetyl from Rhizoma Alismatis
The method of alisol C, simple to operate, product content is high, and the response rate is high, is suitable for industrialized production.
Technical scheme:
A kind of method extracting 23-alisol acetyl C from Rhizoma Alismatis, comprises the following steps:
1] extract
Raw material Rhizoma Alismatis is pulverized, with the aqueous alkali moistening 4h that concentration is 0.1%-10%, uses water or organic solvent extraction 2-3
Secondary, then to extracting solution concentration；
Described aqueous alkali is potassium hydroxide solution, sodium hydroxide solution, calcium hydroxide or ammonia；Described organic solvent is acetic acid
Ethyl ester, chloroform, methanol or ethanol；
2] membrance separation
Gained concentrated solution in step 1 is used Ultra filtration membrane, and gained ultrafiltrate with nanofiltration membrane separation, collects medicinal liquid again,
Concentration of liquid medicine dried is obtained dried powder；
The retaining molecular weight of described ultrafilter membrane is 1000-2000dalton, 2000-5000dalton, 5000-
8000dalton；The retaining molecular weight of described NF membrane is 150-450dalton, 400-600dalton, 400-
1000dalton、400-800dalton；
3] remove impurity
Under the conditions of 10 DEG C-60 DEG C, the solvent adding 1-10 times amount in step 2 gained dried powder carries out dissolving 1-
3h, filters, is then concentrated to dryness the 0.5-3 times amount of powder quality；
Described solvent is one or more mixing in petroleum ether, ethyl acetate, dichloromethane, acetone, isopropanol；
4] crystallization
Adding concentration in step 3 gained concentrated solution is 1%-10% clarifier, under the conditions of 40 DEG C-60 DEG C, is incubated 1h-
2h, filters, is concentrated into the 0.1-0.8 times amount of original volume, and the concentration of the 0.1-0.5 times of quality being subsequently adding concentrated solution is 98%
Ethanol, stands crystallization, centrifugal drying, obtains 23-alisol acetyl C.
Described clarifier is ZTC I A+B, ZTC II A+B, ZTC III A+B, ZTC IV A+B, cationic flocculant,
One or more mixing in Flokal B, composite flocculation agent, non-ionic flocculant.
In above-mentioned steps 1, raw material Rhizoma Alismatis is pulverized, with the calcium hydroxide moistening 4h that concentration is 0.5%, use ethyl acetate
Extract 2 times, then to extracting solution concentration.
In above-mentioned steps 2, it is the super of 2000-5000dalton that gained concentrated solution in step 1 uses retaining molecular weight
Filter membrane separates, and gained ultrafiltrate is the nanofiltration membrane separation of 400-1000dalton with retaining molecular weight again, collects medicinal liquid, by medicine
Liquid concentrate drying processes to obtain dried powder.
In above-mentioned steps 3, under the conditions of 50 DEG C, the mass ratio adding 6 times amount in step 2 gained dried powder is 1:1:
0.5:0.2 ethyl acetate, dichloromethane, acetone, the mixed solvent of isopropanol dissolve, then by lysate concentration.
In above-mentioned step 4, adding 0.02 times amount concentration in step 3 gained concentrated solution is 1.5% composite flocculation agent,
Under the conditions of 50 DEG C, being incubated 1h, filter, be concentrated into 0.7 times amount of original volume, being subsequently adding 0.15 times amount concentration is 98% ethanol,
Stand crystallization, centrifugal drying, both obtain 23-alisol acetyl C.
The material of above-mentioned ultrafilter membrane and NF membrane is PVC, PES, PAN or PVDF.
Advantages of the present invention:
1, use aqueous alkali moistening, the impurity molecule of big for part polarity can be removed；
2, by extracting solution by membrance separation, replace conventional step center pillar to separate, reduce production link；
3, optimizing the combination of technique, make production cost be substantially reduced, flow process shortens, and product yield is high；
4, whole technique simply easily industrialized production.
Detailed description of the invention
Embodiment one:
100kg raw material pulverizing is to 40 mesh, and with the potassium hydroxide solution moistening 4h that 200kg concentration is 0.1%, employing concentration is
80% ethanol extraction 3 times, extracts 2h every time, and extracting solution is standby after concentrating.
Carrying out medicinal liquid clarification by extracting the tubular membrane that concentration employing material is PVC, its molecular cut off is 2000-
5000dalton, collects clear liquid and dope, clear liquid continuation nanofiltration membrane separation, and the material of employing is the hollow-fibre membrane of PVDF,
Molecular cut off is 150-450dalton, collects dope, is dried after concentration；
By dry powder, under conditions of 40 DEG C, use dichloromethane and the acetone mixed solvent of 2 times of dried powder quality
Dissolving 1h, its mass ratio is 1:1, filters, is concentrated to dryness 1 times amount of powder quality, places standby；
Be initially charged the ZTC I A+B type clarifier of concentrated solution quality 1% to 40 DEG C of concentrated solutions, wherein the concentration of A, B is
2%, first stirring adds B, and after 10 minutes to be mixed, the mass ratio adding A, itself B and A is 2:1, and 40 DEG C are incubated 20 minutes；Then
Adding the non-ionic flocculant that concentration is 2.0% of concentrated solution quality 1%, be incubated 1h, filter under the conditions of 40 DEG C, filtrate concentrates
To 0.1 times amount of original volume, in concentrated solution, add the ethanol that concentration is 98% of 0.1 times of concentrated solution quality, place crystallization, from
The heart is dried, and obtains 180g, and content is the product of 98.2%.
Embodiment two
100kg raw material pulverizing, to 20 mesh, with the sodium hydroxide solution moistening 4h of 300kg 1.2%, uses ethyl acetate to carry
Taking 3 times, extract 2h every time, extracting solution is standby after concentrating；
Carrying out medicinal liquid clarification by extracting the tubular membrane that concentration employing material is PES, its molecular cut off is 5000-
8000dalton, collects clear liquid and dope, clear liquid continuation nanofiltration membrane separation, and the material of employing is the hollow-fibre membrane of PVDF,
Molecular cut off is 400-600dalton, collects dope, is dried after concentration.
By dry powder, under conditions of 50 DEG C, use the dichloromethane of 10 times of dried powder quality and the mixed of isopropanol
Bonding solvent dissolves 2h, and its mass ratio is 3:2, filters, is concentrated to dryness 3 times amount of powder quality, places standby；
Add the ZTC III A+B type clarifier of concentrated solution quality 10% to 60 DEG C of concentrated solutions, wherein the concentration of A, B is
10%, first stirring adds B, and after 15 minutes to be mixed, the mass ratio adding A, itself B and A is 1:2.60 DEG C are incubated 40 minutes.Then
Adding the Flokal B that concentration is 1% of concentrated solution quality 1.2%, filtering, filtrate is concentrated into 1 times amount of original volume,
In concentrated solution, add the ethanol that concentration is 98% of 0.2 times of concentrated solution quality, place crystallization, centrifugal drying, obtain 185g, contain
Amount is the product of 98.6%.
Embodiment three
100kg raw material pulverizing is to 30 mesh, and with the aqua calcis moistening 4h of 150kg 5%, using concentration is 80% first
Alcohol extraction 2 times, extracts 1.5h every time, and extracting solution is standby after concentrating
Carrying out medicinal liquid clarification by extracting the tubular membrane that concentration employing material is PAN, its molecular cut off is 1000-
2000dalton, collects clear liquid and dope, clear liquid continuation nanofiltration membrane separation, and the material of employing is the hollow-fibre membrane of PVDF,
Molecular cut off is 400-1000dalton, collects dope, is dried after concentration；
By dry powder, under conditions of 60 DEG C, use ethyl acetate and the mixing of isopropanol of 8 times of dried powder quality
Solvent dissolves 1.5h, and its mass ratio is 1:1, filters, is concentrated to dryness 1.5 times amount of powder quality, places standby.
Be initially charged the ZTC II A+B type clarifier of concentrated solution quality 5% to 40 DEG C of concentrated solutions, wherein the concentration of A, B is
6%, first stirring adds B, and after 20 minutes to be mixed, the mass ratio adding A, itself B and A is 3:1,40 DEG C of insulation 1h, places；Cross
Filter, filtrate is concentrated into 0.5 times amount of original volume, adds the ethanol that concentration is 98% of 0.5 times of concentrated solution quality in concentrated solution,
Placing crystallization, centrifugal drying, obtain 183g, content is the product of 98.4%.
Embodiment four
100kg raw material pulverizing, to 60 mesh, with the aqua calcis moistening 4h that 180kg concentration is 0.5%, uses acetic acid second
Ester extracts 2 times, extracts 1.5h every time, standby after extracting solution；
Said extracted concentrating the tubular membrane using material to be PVDF and carries out medicinal liquid clarification, its molecular cut off is 2000-
5000dalton, collects clear liquid and dope, clear liquid continuation nanofiltration membrane separation, and the material of employing is the hollow-fibre membrane of PVDF,
Molecular cut off is 400-1000dalton, collects dope, is dried after concentration；
By dry powder, under conditions of 50 DEG C, use the ethyl acetate of 6 times of dried powder quality, dichloromethane, third
Ketone, the mixed solvent of isopropanol dissolve 3h, and its mass ratio is 1:1:0.5:0.2, filters, is concentrated to dryness 1 times of powder quality
Amount, places standby；
Add the composite flocculation agent that concentration is 1.5% of concentrated solution quality 2% to 50 DEG C of concentrated solutions, be incubated under the conditions of 50 DEG C
1h, filters, and filtrate is concentrated into 0.7 times amount of original volume, and the concentration adding 0.15 times of concentrated solution quality in concentrated solution is 98%
Ethanol, place crystallization, centrifugal drying, obtain 190g, content is the product of 99.1%.
Embodiment five
100kg raw material pulverizing, to 50 mesh, with the ammonia spirit moistening 4h that 150kg concentration is 10%, uses chloroform extraction 3
Secondary, extract 3h every time, extracting solution is standby after concentrating；
Said extracted concentrating the tubular membrane using material to be PVC and carries out medicinal liquid clarification, its molecular cut off is 5000-
8000dalton, collects clear liquid and dope, clear liquid continuation nanofiltration membrane separation, and the material of employing is the hollow-fibre membrane of PES, cuts
Staying molecular weight is 400-800dalton, collects dope, is dried after concentration；
By dry powder, under conditions of 40 DEG C, use the dichloromethane of 1 times of dried powder quality, acetone, ethyl acetate
Mixed solvent dissolve 2.5h, its mass ratio is 1:3.5:0.8, filter, be concentrated to dryness 0.5 times amount of powder quality, place
Standby；
Be initially charged the ZTC IV A+B type clarifier of concentrated solution quality 30% to 60 DEG C of concentrated solutions, wherein the concentration of A, B is equal
Being 4%, first stirring adds B, and after 13 minutes to be mixed, the mass ratio adding A, itself B and A is 3:2, and 60 DEG C are incubated 15 minutes；So
After add concentrated solution quality 1.5% the cationic flocculant that concentration is 3.5%, under the conditions of 60 DEG C be incubated 1h, filter, filtrate
It is concentrated into 0.8 times amount of original volume, in concentrated solution, adds the ethanol that concentration is 98% of 0.3 times of concentrated solution quality, place knot
Crystalline substance, centrifugal drying, obtain 188g, content is the product of 98.7%.
Can draw through abundant experimental results, the method gained product separating 23-alisol acetyl C should be extracted from Rhizoma Alismatis
The yield of product is more than or equal to 0.18%, and in product, 23-alisol acetyl C content is more than or equal to 98.0%；Therefore, the method product
Content is high, and the response rate is high, is suitable for industrialized production.
The present invention and prior art carry out experimental result contrast, and draw following result:
| CN201010554160.2 | The present invention | |
| Yield | 0.167%～0.172% | More than 0.18% |
| Content | 93.8%～97.9% | More than 98.0% |
| Production cost | 22.7 ten thousand yuan/kg | 12.2 ten thousand yuan/kg |
| Production cycle | 60h | 30h |
| Step | 5 steps | 4 steps |
Claims (6)
1. the method extracting 23-alisol acetyl C from Rhizoma Alismatis, it is characterised in that comprise the following steps:
1] extract
Raw material Rhizoma Alismatis is pulverized, with the aqueous alkali moistening 4h that concentration is 0.1%-10%, uses organic solvent extraction 2-3 time, then
To extracting solution concentration；
Described aqueous alkali is potassium hydroxide solution, sodium hydroxide solution, calcium hydroxide or ammonia；Described organic solvent is acetic acid second
Ester, chloroform, methanol or ethanol；
2] membrance separation
Gained concentrated solution in step 1 is used Ultra filtration membrane, and gained ultrafiltrate with nanofiltration membrane separation, collects medicinal liquid, by medicine again
Liquid concentrate drying processes to obtain dried powder；
The retaining molecular weight of described ultrafilter membrane is 1000-2000dalton, 2000-5000dalton, 5000-
8000dalton；The retaining molecular weight of described NF membrane is 150-450dalton, 400-600dalton, 400-
1000dalton、400-800dalton；
3] remove impurity
Under the conditions of 10 DEG C-60 DEG C, the solvent adding 1-10 times amount in step 2 gained dried powder carries out dissolving 1-3h, mistake
Filter, is then concentrated to dryness the 0.5-3 times amount of powder quality；
Described solvent is one or more mixing in petroleum ether, ethyl acetate, dichloromethane, acetone, isopropanol；
4] crystallization
Adding concentration in step 3 gained concentrated solution is 1%-10% clarifier, under the conditions of 40 DEG C-60 DEG C, is incubated 1h-2h,
Filter, be concentrated into the 0.1-0.8 times amount of original volume, be subsequently adding the second that concentration is 98% of 0.1-0.5 times of quality of concentrated solution
Alcohol, stands crystallization, centrifugal drying, obtains 23-alisol acetyl C；
Described clarifier is ZTC I A+B, ZTC II A+B, ZTC III A+B, ZTC IV A+B, cationic flocculant, cloudy from
One or more mixing in sub-flocculant, composite flocculation agent, non-ionic flocculant.
The method extracting 23-alisol acetyl C from Rhizoma Alismatis the most according to claim 1, it is characterised in that: described step
In 1, raw material Rhizoma Alismatis is pulverized, with the calcium hydroxide moistening 4h that concentration is 0.5%, use ethyl acetate to extract 2 times, then to carrying
Take liquid concentration.
The method extracting 23-alisol acetyl C from Rhizoma Alismatis the most according to claim 2, it is characterised in that: described step
In 2, gained concentrated solution in step 1 is used retaining molecular weight is the Ultra filtration membrane of 2000-5000dalton, gained ultrafiltration
Liquid is the nanofiltration membrane separation of 400-1000dalton with retaining molecular weight again, collects medicinal liquid, concentration of liquid medicine dried is obtained
Dried powder.
The method extracting 23-alisol acetyl C from Rhizoma Alismatis the most according to claim 3, it is characterised in that: described step
In 3, under the conditions of 50 DEG C, add in step 2 gained dried powder the mass ratio of 6 times amount be 1:1:0.5:0.2 ethyl acetate,
Dichloromethane, acetone, the mixed solvent of isopropanol dissolve, then by lysate concentration.
The method extracting 23-alisol acetyl C from Rhizoma Alismatis the most according to claim 4, it is characterised in that: described step
In rapid 4, adding 0.02 times amount concentration in step 3 gained concentrated solution is 1.5% composite flocculation agent, under the conditions of 50 DEG C, and insulation
1h, filters, is concentrated into 0.7 times amount of original volume, and being subsequently adding 0.15 times amount concentration is 98% ethanol, stands crystallization, centrifugal dry
Dry, both obtained 23-alisol acetyl C.
The method extracting 23-alisol acetyl C from Rhizoma Alismatis the most according to claim 5, it is characterised in that: described ultrafiltration
The material of film and NF membrane is PVC, PES, PAN or PVDF.
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| CN107964031B (en) * | 2017-12-22 | 2020-04-14 | 成都普思生物科技股份有限公司 | Triterpenoid extracted and separated from rhizoma alismatis, and method and application thereof |
| CN112876529A (en) * | 2021-01-25 | 2021-06-01 | 福建中医药大学 | Purification preparation method of 23-acetyl alisol C and application thereof in preparing anti-osteoporosis medicine |
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| CN102093454B (en) * | 2010-11-23 | 2012-08-15 | 苏州派腾生物医药科技有限公司 | Preparation method of alisol C monoacetic ester |
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Address after: 710075 Xi'an high tech Zone, Shaanxi hi tech Road, No. 25 Maple Leaf Garden District, block C, No. 157 Applicant after: SHAANXI JIAHE PHYTOCHEM CO., LTD. Address before: 710075 Xi'an high tech Zone, Shaanxi hi tech Road, No. 25 Maple Leaf Garden District, block C, No. 157 Applicant before: Shanxi Jiahe Plant Chemical Co., Ltd. |
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