CN106083983A - A kind of method preparing helexin from Fructus Sapindi Mukouossi - Google Patents
A kind of method preparing helexin from Fructus Sapindi Mukouossi Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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Abstract
The invention provides a kind of method preparing helexin from Fructus Sapindi Mukouossi, the method utilizes alcohol water mixed solvent to extract total saponin of sapindusmukerossi, through hydrolyzing and using purified by crystallisation to obtain helexin.The helexin preparation method productivity of the present invention is high, simple to operate, mild condition, with low cost, environmental protection.Helexin preparation method of the present invention, highly purified helexin can not only be obtained, and production cost is cheaper than existing, and productivity is greatly improved, it is a kind of production method with wide application prospect, the demand of the medical industry developed rapidly can be met.
Description
Technical field
The present invention relates to extract drug activity ingredient technology field from natural plants, be specifically related to a kind of from Fructus Sapindi Mukouossi
The method preparing helexin.
Technical background
Research data shows, helexin has the functions such as antidepressant, fat-reducing, blood fat reducing, blood sugar lowering and (sees patent
1:CN 101214250A；Patent 2:CN 101564405A；Patent 3:CN 02109763.1；Patent 4:CN 101125880A),
The most simple and effective this compound that obtains at low cost becomes focus of concern.Helexin is planted in major part
In thing, content is relatively low, and how exists with saponin form, if therefore industrialization, producing this compound, its basic ideas in large quantities
It is exactly first total saponins to be extracted from the plant that its content is higher, then is translated into aglycon with acid-hydrolysis method, finally adopt
Highly purified helexin is obtained with crystallization process.
Helexin is prepared, it is common that by the Chang Chun in Chinese herbal medicine from the Chinese herbal medicine containing Hederagenin
Rattan saponin direct hydrolysis becomes aglycon, then extracts sapogenin from filtering residue with low pole or non-polar solven, then carries out crude product point
From purification, this method need to consume substantial amounts of acid, and filtering residue is the most neutral by massive laundering again, thus produces a large amount of acid pickle, and
And once saponin hydrolysis is not thorough, then directly affect the total yield of aglycon.The patent of Publication No. CN102633857A is reported
Method be i.e. to have employed first hydrolyzing saponin, then the thinking of extraction separation and purification sapogenin so that production line is longer, adds
The consumption of acid and the corrosion of equipment, and produce a large amount of waste acid water liquid.
After obtaining helexin extracting solution or hydrolyzed solution, for further isolated and purified product, in subsequent technique
Often use ion exchange, membrane filter method, metal salts as precipitator, active carbon adsorption etc. and extracting solution or hydrolyzed solution are carried out pre-
Process, the most again after further concentrating under reduced pressure, carry out recrystallization or spray drying.These methods are primarily present three and ask
Topic: one is that the selectivity to impurity is the highest, does not has gratifying impurity-eliminating effect, and two is to bring serious target to produce
The problem of thing loss；Three is that the concentration of these methods pretreated solution decompression is required for higher energy consumption.Problem above is very big
Add production cost.
Lot of documents report helexin is a kind of sky with functions such as antidepressant, blood sugar lowering, blood fat reducing, fat-reducing
So active substance, yet with the deficiency of tradition extraction separation and purification method, significantly constrains and helexin is entered one
Step researches and exploitation.Therefore, find practical and be suitable to heavy industrialization and prepare high-purity helexin
Preparation method, will have great economic benefit and social benefit.
Summary of the invention
It is contemplated that overcome the deficiencies in the prior art, it is provided that a kind of simplicity, the efficient and Hederagenin of energy-conserving and environment-protective
The preparation method of unit, to solve the problem that heavy industrialization prepares high-purity helexin.
The preparation method of helexin of the present invention, is with Chinese crude drug Fructus Sapindi Mukouossi as raw material, often obtains according to the following steps
Caulis Hederae Sinensis total aglycone goods:
1) preparing volumetric concentration is 60～the ethanol water of 95% or methanol aqueous solution are as extracting solution；
2) seed of Chinese crude drug Fructus Sapindi Mukouossi is taken out, obtain Fructus Sapindi Mukouossi powder after its peel is dried and is pulverized, according to solid-liquid ratio
1: 5～10 kg/L will carry out reflux, extract, in Fructus Sapindi Mukouossi powder addition said extracted solution, and reflux, extract, temperature is 50～80
DEG C, reflux, extract, 2～obtain extracting solution for 8 hours, extracting solution cooled and filtered also collects filtrate, filtrate is condensed into syrupy shape and carries
Take thing；
3) (present invention refers both to and deionization to add extract weight 4～the deionized water of 9 times and equal-volume in above-mentioned extract
Water equal-volume) the sulfuric acid solution that concentration is 2～3mol/L solution such as (or) hydrochloric acid, under 50～80 DEG C of water-baths, hydrolyze 2～8 little
It is centrifuged time after, abandoning supernatant, precipitate is washed with deionized repeatedly to white, is dried, obtains white or Petiolus Trachycarpi toner
End；
4) above-mentioned powder is dissolved in dehydrated alcohol, with alkali liquor regulation pH to alkalescence, filters off insoluble matter, in filtrate, add acid solution adjust
Joint pH, to acid, stands overnight, sucking filtration after separating out crystal, and the solid collected after sucking filtration is dried, and obtains helexin.
Can be sodium hydroxide solution, potassium hydroxide etc. for regulating the alkali liquor of pH；
Can be hydrochloric acid solution, sulfuric acid solution etc. for regulating the acid solution of pH；
Preferably, the ethanol water of described step 1) or the volumetric concentration of methanol aqueous solution are 70～80%.
Described step 2) solid-liquid ratio be 1: 6～8 kg/L.
Described step 2) concentrate the filtrate to the 0.5-10% of original volume, obtain syrupy shape extract.
Described step 3) adds extract weight 6～the deionized water of 8 times in extract.
Described step 3) hydrolysis time is 4-6 hour.
Powder is dissolved in dehydrated alcohol by described step 4), regulates pH to PH=11-with sodium hydroxide solution or other alkali liquor
13。
Described step 4), adds hydrochloric acid or other acid solution regulation pH to PH=1-3 in filtrate.
The baking temperature of described step 4) is less than 50 DEG C.
The present invention uses above technical scheme, selects the plant (Fructus Sapindi Mukouossi) that Hederagenin content is high, first uses machine solvent
Hederagenin is extracted from Fructus Sapindi Mukouossi, then prepares helexin crude product with acid-hydrolysis method, then use crystallization process
Prepare high-purity helexin, at present, adopt the method preparing helexin in this way from Chinese medicine Fructus Sapindi Mukouossi
There is not been reported.
The remarkable advantage of the present invention is: easy and simple to handle, step is brief, it is to avoid first hydrolyzing saponin, the most again to obtained
The further extracting and developing of sapogenin, purification a series of loaded down with trivial details, time-consuming, power consumption step, avoid first to greatest extent
The loss problem of the helexin not exclusively caused because of saponin hydrolysis in the method for kind.Meanwhile, the present invention uses crystallization skill
Art, efficiently complete target product with physical means is isolated and purified, overcomes additive method incomplete to Impurity removal, easy
Target product is caused to lose, and the high energy consumption problem of subsequent concentration recycling design, be conducive to its preparation of industrialization.
Accompanying drawing explanation
Below in conjunction with the drawings and specific embodiments, the invention will be further described:
Fig. 1 is the mass spectrum of helexin；
Fig. 2 is the infrared spectrogram of helexin.
Detailed description of the invention
A kind of method preparing helexin from Fructus Sapindi Mukouossi, comprises the following steps:
1) preparing volumetric concentration is 60～the ethanol water of 95% or methanol aqueous solution are as extracting solution；
2) seed of Chinese crude drug Fructus Sapindi Mukouossi is taken out, obtain Fructus Sapindi Mukouossi powder after its peel is dried and is pulverized, according to solid-liquid ratio
1: 5～10 kg/L will carry out reflux, extract, in Fructus Sapindi Mukouossi powder addition said extracted solution, and reflux, extract, temperature is 50～80
DEG C, reflux, extract, 2～extremely extraction in 8 hours obtain extracting solution completely, and extracting solution cooled and filtered also collects filtrate, filtrate is concentrated
Become the 0.5-10% of original volume, obtain syrupy shape extract；
3) in above-mentioned extract, add extract weight 4～the deionized water of 9 times and isopyknic concentration is 2～3mol/L
Sulfuric acid solution, centrifugal after hydrolyzing 2～8 hours under 50～80 DEG C of water-baths, abandoning supernatant, precipitate is washed with deionized
Repeatedly to white, it is dried, obtains white or taupe powder；
4) above-mentioned powder is dissolved in dehydrated alcohol, with alkali liquor regulation pH to alkalescence (PH=11-13), filters off insoluble matter, in filtrate
Adding acid solution regulation pH the most acid (PH=1-3), stand overnight, sucking filtration after separating out crystal, the solid collected after sucking filtration is being less than
It is dried at a temperature of 50 DEG C, obtains helexin.
It is below several instantiations of the present invention, further describes the present invention, but the present invention is not limited only to this.
Embodiment 1
A kind of method preparing helexin from Fructus Sapindi Mukouossi, comprises the following steps:
1) adding a certain amount of deionized water in dehydrated alcohol, prepared volumetric concentration is the ethanol water of 80%, molten for extracting
Liquid；
2) seed of Chinese crude drug Fructus Sapindi Mukouossi is taken out, obtain Fructus Sapindi Mukouossi powder after its peel is dried and is pulverized, according to solid-liquid ratio
1: 6kg/L will carry out reflux, extract, in Fructus Sapindi Mukouossi powder addition said extracted solution, and reflux, extract, temperature is 80 DEG C, and backflow carries
Taking 4 hours and obtain extracting solution completely to extraction, extracting solution cooled and filtered also collects filtrate, and filtrate is condensed into original volume
5%, obtain syrupy shape extract；
3) deionized water and the sulphuric acid that isopyknic concentration is 2mol/L that add extract weight 6 times in above-mentioned extract are molten
Liquid, centrifugal after hydrolyzing 4 hours under 70 DEG C of water-baths, abandoning supernatant, precipitate is washed with deionized repeatedly to white, dry
Dry, obtain taupe powder；
4) above-mentioned powder is dissolved in dehydrated alcohol, with sodium hydroxide solution regulation pH to alkalescence (PH=11), filters off insoluble matter, to
Adding salt acid for adjusting pH in filtrate the most acid (PH=3), stand overnight, sucking filtration after separating out crystal, the solid collected after sucking filtration exists
It is dried at a temperature of less than 50 DEG C, obtains helexin.
The present embodiment, step 2) it is to add 1kg Fructus Sapindi Mukouossi powder in 6L ethanol water to carry out reflux, extract, obtain
Brown ceramic powder is 278g, and step 4) is finally dried to obtain 67g helexin powder crystal, and through mass spectral analysis, this crystal mass spectrum divides
Son amount is 472, and molecular formula is C30H48O4, Mass Spectrometer Method uses positive ion mode, and m/z295.3444 is quasi-molecular ion peak [M+
Na]+(see figure 1).Infrared analysis display 3375.92cm-1There is-CH at place2The absorption of-OH, 1688.92cm-1There is the absorption of-C=O at place
(see figure 2).
Embodiment 2
A kind of method preparing helexin from Fructus Sapindi Mukouossi, comprises the following steps:
1) methanol aqueous solution that volumetric concentration is 70% is prepared as extracting solution；
2) seed of Chinese crude drug Fructus Sapindi Mukouossi is taken out, obtain Fructus Sapindi Mukouossi powder after its peel is dried and is pulverized, according to solid-liquid ratio
1: 8 kg/L will carry out reflux, extract, in Fructus Sapindi Mukouossi powder addition said extracted solution, and reflux, extract, temperature is 70 DEG C, and backflow carries
Taking 6 hours and obtain extracting solution completely to extraction, extracting solution cooled and filtered also collects filtrate, and filtrate is condensed into original volume
3%, obtain syrupy shape extract；
3) deionized water and the sulphuric acid that isopyknic concentration is 3mol/L that add extract weight 8 times in above-mentioned extract are molten
Liquid, centrifugal after hydrolyzing 6 hours under 60 DEG C of water-baths, abandoning supernatant, precipitate is washed with deionized repeatedly to white, dry
Dry, obtain taupe powder；
4) above-mentioned powder is dissolved in dehydrated alcohol, with sodium hydroxide solution regulation pH to alkalescence (PH=12), filters off insoluble matter, to
Adding salt acid for adjusting pH in filtrate the most acid (PH=2), stand overnight, sucking filtration after separating out crystal, the solid collected after sucking filtration exists
It is dried at a temperature of less than 50 DEG C, obtains helexin.
Embodiment 3
A kind of method preparing helexin from Fructus Sapindi Mukouossi, comprises the following steps:
1) ethanol water that volumetric concentration is 60% or methanol aqueous solution are prepared as extracting solution；
2) seed of Chinese crude drug Fructus Sapindi Mukouossi is taken out, obtain Fructus Sapindi Mukouossi powder after its peel is dried and is pulverized, according to solid-liquid ratio
1: 10 kg/L will carry out reflux, extract, in Fructus Sapindi Mukouossi powder addition said extracted solution, and reflux, extract, temperature is 50 DEG C, backflow
Extracting 8 hours and obtain extracting solution completely to extraction, extracting solution cooled and filtered also collects filtrate, and filtrate is condensed into original volume
0.5%, obtain syrupy shape extract；
3) deionized water and the sulphuric acid that isopyknic concentration is 2mol/L that add extract weight 9 times in above-mentioned extract are molten
Liquid, centrifugal after hydrolyzing 8 hours under 50 DEG C of water-baths, abandoning supernatant, precipitate is washed with deionized repeatedly to white, dry
Dry, obtain grayish powder；
4) above-mentioned powder is dissolved in dehydrated alcohol, with sodium hydroxide solution regulation pH to alkalescence (PH=13), filters off insoluble matter, to
Adding salt acid for adjusting pH in filtrate the most acid (PH=1), stand overnight, sucking filtration after separating out crystal, the solid collected after sucking filtration exists
It is dried at a temperature of less than 50 DEG C, obtains helexin.
Embodiment 4
A kind of method preparing helexin from Fructus Sapindi Mukouossi, comprises the following steps:
1) ethanol water that volumetric concentration is 95% or methanol aqueous solution are prepared as extracting solution；
2) seed of Chinese crude drug Fructus Sapindi Mukouossi is taken out, its peel is dried and pulverizes, will be without suffering from according to solid-liquid ratio 1: 5 kg/L
Sub-powder adds in said extracted solution and carries out reflux, extract, and reflux, extract, temperature is 80 DEG C, and reflux, extract, 2 hours is to having extracted
Entirely obtaining extracting solution, extracting solution cooled and filtered also collects filtrate, and filtrate is condensed into the 10% of original volume, obtains syrupy shape and carries
Take thing；
3) deionized water and the sulphuric acid that isopyknic concentration is 3mol/L that add extract weight 4 times in above-mentioned extract are molten
Liquid, centrifugal after hydrolyzing 2 hours under 80 DEG C of water-baths, abandoning supernatant, precipitate is washed with deionized repeatedly to white, dry
Dry, obtain taupe powder；
4) above-mentioned powder is dissolved in dehydrated alcohol, with sodium hydroxide solution regulation pH to alkalescence (PH=12), filters off insoluble matter, to
Adding salt acid for adjusting pH in filtrate the most acid (PH=2), stand overnight, sucking filtration after separating out crystal, the solid collected after sucking filtration exists
It is dried at a temperature of less than 50 DEG C, obtains helexin.
Claims (9)
1. the method preparing helexin from Fructus Sapindi Mukouossi, it is characterised in that: it comprises the following steps:
1) preparing volumetric concentration is 60～the ethanol water of 95% or methanol aqueous solution are as extracting solution；
2) seed of Chinese crude drug Fructus Sapindi Mukouossi is taken out, obtain Fructus Sapindi Mukouossi powder after its peel is dried and is pulverized, according to solid-liquid ratio
1: 5～10 kg/L will carry out reflux, extract, in Fructus Sapindi Mukouossi powder addition said extracted solution, and reflux, extract, temperature is 50～80
DEG C, reflux, extract, 2～obtain extracting solution for 8 hours, extracting solution cooled and filtered also collects filtrate, filtrate is condensed into syrupy shape and carries
Take thing；
3) in above-mentioned extract, add extract weight 4～the deionized water of 9 times and isopyknic concentration is 2～3mol/L
Sulfuric acid solution, centrifugal after hydrolyzing 2～8 hours under 50～80 DEG C of water-baths, abandoning supernatant, precipitate is washed with deionized
Repeatedly, it is dried, obtains powder；
4) above-mentioned powder is dissolved in dehydrated alcohol, with alkali liquor regulation pH to alkalescence, filters off insoluble matter, in filtrate, add acid solution adjust
Joint pH, to acid, stands overnight, sucking filtration after separating out crystal, and the solid collected after sucking filtration is dried, and obtains helexin.
The preparation method of helexin the most according to claim 1, it is characterised in that: the ethanol water of described step 1)
The volumetric concentration of solution or methanol aqueous solution is 70～80%.
The preparation method of helexin the most according to claim 1, it is characterised in that: described step 2) solid-liquid ratio
It is 1: 6～8 kg/L.
The preparation method of helexin the most according to claim 1, it is characterised in that: described step 2) filtrate is dense
It is reduced to the 0.5-10% of original volume, obtains syrupy shape extract.
The preparation method of helexin the most according to claim 1, it is characterised in that: described step 3) is to extract
Middle addition extract weight 6～the deionized water of 8 times.
The preparation method of helexin the most according to claim 1, it is characterised in that: described step 3) hydrolysis time
For 4-6 hour.
The preparation method of helexin the most according to claim 1, it is characterised in that: described step 4) is molten by powder
In dehydrated alcohol, regulate pH to PH=11-13 with sodium hydroxide solution.
The preparation method of helexin the most according to claim 1, it is characterised in that: described step 4), in filtrate
Add salt acid for adjusting pH to PH=1-3.
9. according to the preparation method of the helexin described according to claim 1, it is characterised in that: being dried of described step 4)
Temperature is less than 50 DEG C.
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| CN201610450153.5A CN106083983B (en) | 2016-06-20 | 2016-06-20 | A kind of method that hederagenin is prepared from soapberry |
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| CN201610450153.5A CN106083983B (en) | 2016-06-20 | 2016-06-20 | A kind of method that hederagenin is prepared from soapberry |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107228833A (en) * | 2017-04-21 | 2017-10-03 | 东莞微领生物科技有限公司 | A kind of total saponin of sapindusmukerossi quick detection kit and detection method |
| CN108794562A (en) * | 2018-08-30 | 2018-11-13 | 佛山市欧若拉生物科技有限公司 | A kind of processing technology of sapindoside extract |
| CN111018937A (en) * | 2019-11-25 | 2020-04-17 | 国际竹藤中心 | Method for preparing soapberry saponin monomer by high-speed counter-current chromatography |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101564405A (en) * | 2009-05-26 | 2009-10-28 | 赵全成 | Application of total aglycone of himalayan teasel roots and single-component hederagenin in medicaments preparing Alpha-glucosidase inhibitor |
| CN102633857A (en) * | 2012-04-24 | 2012-08-15 | 吉林大学 | Extraction method of hederagenin |
-
2016
- 2016-06-20 CN CN201610450153.5A patent/CN106083983B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101564405A (en) * | 2009-05-26 | 2009-10-28 | 赵全成 | Application of total aglycone of himalayan teasel roots and single-component hederagenin in medicaments preparing Alpha-glucosidase inhibitor |
| CN102633857A (en) * | 2012-04-24 | 2012-08-15 | 吉林大学 | Extraction method of hederagenin |
Non-Patent Citations (2)
| Title |
|---|
| AMITA SHARMA ET AL.: ""Triterpenoid saponins from the pericarps of Sapindus mukorossi"", 《JOURNAL OF CHEMISTRY》 * |
| 何宇新 等: ""反相高效液相色谱法测定不同产地无患子药材中常春藤皂苷元的含量"", 《时珍国医国药》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107228833A (en) * | 2017-04-21 | 2017-10-03 | 东莞微领生物科技有限公司 | A kind of total saponin of sapindusmukerossi quick detection kit and detection method |
| CN107228833B (en) * | 2017-04-21 | 2020-07-17 | 东莞微领生物科技有限公司 | Rapid detection kit and detection method for total saponins of soapberry |
| CN108794562A (en) * | 2018-08-30 | 2018-11-13 | 佛山市欧若拉生物科技有限公司 | A kind of processing technology of sapindoside extract |
| CN111018937A (en) * | 2019-11-25 | 2020-04-17 | 国际竹藤中心 | Method for preparing soapberry saponin monomer by high-speed counter-current chromatography |
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