CN103408558A - Cloud point extraction based psoralen and isopsoralen extracting method - Google Patents
Cloud point extraction based psoralen and isopsoralen extracting method Download PDFInfo
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Abstract
The invention discloses a cloud point extraction based psoralen and isopsoralen extracting method. The method comprises the following steps: fully mixing Psoralea corylifolia powder with a surfactant solution, and extracting under an ultrasonic condition; collecting the obtained extract liquid after extracting completion, centrifuging, collecting the obtained supernatant, adding an electrolyte for adjusting the ion intensity, balancing in a constant temperature water bath, and allowing the supernatant obtained after the centrifugation to stand in order to obtain an aqueous surfactant solution layer and a surfactant enrichment layer; and filtering the surfactant enrichment layer by an ultrafilter membrane after the two-phase layering, recovering the surfactant, and carrying out rotation evaporation of the obtained filtrate to obtain a fat-soluble crude extract containing psoralen and isopsoralen. The method has the advantages of no need of toxic harmful organic solvents, extracting rate increase, environmental pollution reduction, and suitableness for the industrialized large-scale extraction.
Description
Technical field
The invention belongs to the extractive technique field of active components of plants, relate to a kind of method of extracting psoralen and isopsorapen based on cloud point extraction.
Background technology
Psoralen and isopsorapen is effective constituent important in Psoralea corylifolia.Because the content in plant such as Psoralea corylifolia are low, and the monomer extraction yield is lower.Study efficient psoralen and isopsorapen extracting method significant.In fact, the major cause that the monomer extraction yield is low is the first step when plant, obtaining efficient part (crude extract), most conventional organic solvents extraction methods of using, and this technique reflux temperature is high, and effective constituent is oxidized or decompose and destroy, cause extraction yield low.Visible raising Psoralea corylifolia crude extract extraction yield is prerequisite and the key that realizes that high yield is extracted.
The method of extracting for efficient part in the plant Psoralea corylifolia is a lot, mainly contains:
1) organic solvent extraction method:
The organic solvent extraction method is to using organic solvent as a kind of extraction means of disperse phase, and this method is applicable to the extraction of many organic compositions, such as flavonoid, glycoside, coumarins etc.Also to extract at present efficient part in plant to use maximum a kind of extracting method.But main drawback is: complex operation, extraction yield are low, the enrichment rate variance.Especially use the poisonous organic solvents such as methyl alcohol, environmental pollution is large, dissolvent residual toxicity is high.
2) other method:
In order to overcome the above-mentioned shortcoming of solvent-extraction process, people extract and improve efficient part, mainly comprise supercritical extraction, microwave or ultrasonic-assisted extraction method etc.
Supercritical extraction, be to using carbonic acid gas etc. as supercritical fluid solvent, extracts plant Psoralea corylifolia efficient part.But supercritical fluid extraction equipment belongs to high-tension apparatus, invest greatlyr, usually need organic entrainment agent just can reach desirable separating effect.This method can not be avoided the use of organic solvent.
Microwave or ultrasonic-assisted extraction method: be to utilize microwave or the auxiliary deliquescent a kind of method of solute in solvent that increase of ultrasonic wave.In most cases in laboratory, use.But still need with an organic solvent, can't avoid toxicity and the pollution problem of these solvents.
Cloud-Point Extraction Technique (cloud point extraction is called for short CPE) is a kind of emerging environment-friendly type liquid-liquid technique.Cloud-Point Extraction Technique is usingd water to replace organic solvent as extraction agent, reaches high efficiency extraction separation purpose by adding a small amount of tensio-active agent to produce the cloud point phenomenon.Its principle is: surfactant molecule in the aqueous solution, can form hydrophilic radical outwards, the inside micella of hydrophobic group.This micellar solution can make slightly soluble or water-fast organism solubleness greatly increase.Simultaneously, water phase surfactant mixture is more than being heated to certain temperature (cloud point temperature), and solution becomes muddy and phase-splitting occurs.By changing experiment parameter (as the ionic strength of solution, temperature etc.), cause and be separated, the efficiently concentrating of finally realizing solute with separate.
With traditional Liquid-liquid Extraction Processes, compare; operating between two waters of cloud point extraction isolation technique carried out; so avoided the use of harmful organic solvent; also avoided the impact of volatile organic solvent on environment; and can protect original character of extract; accelerate extracting and separating speed, improve the extracting and enriching rate.And this technology for trace even trace substance good inrichment is arranged.
Summary of the invention
The problem that the present invention solves is to provide a kind of method of extracting psoralen and isopsorapen based on cloud point extraction, and the method, without poisonous and hazardous organic solvent, has increased extraction yield, has reduced environmental pollution.
The present invention is achieved through the following technical solutions:
A kind of method of extracting psoralen and isopsorapen based on cloud point extraction comprises following operation:
1) by Malaytea Scurfpea Fruit with after surfactant soln fully mixes, and extract under ultrasound condition;
2) extracted rear collection extracting solution, centrifugal, collect supernatant liquor and add ionogen to regulate ionic strength, then in the water bath with thermostatic control balance, aqueous layer and tensio-active agent enriched layer that centrifugal rear supernatant liquor phase-splitting is tensio-active agent;
3) after being divided into two-phase, tensio-active agent enriched layer ultrafiltration membrance filter, reclaim tensio-active agent, and filtrate is spin-dried for, and obtains comprising the fat-soluble class crude extract of psoralen and isopsorapen.
Further, specifically comprise the following steps:
1) the Psoralea corylifolia plant powder being joined to volume-fraction concentration is in 10～15% surfactant soln, wherein liquid-solid ratio is 150mL:1g～200mL:1g, in vortex mixer, fully mix, and, under 25 ℃, under 300W ultrasonic processor supersound process, extract 30～35min;
2) extracted rear collection extracting solution, centrifugal, collect supernatant liquor and add ionogen and regulate ionic strength, wherein electrolyte concentration is 2.5～3molL
-1, then centrifugal after 50 ℃ of water bath with thermostatic control balance 35～45min, the supernatant liquor phase-splitting is aqueous layer and the tensio-active agent enriched layer of tensio-active agent;
3) by the ultrafiltration membrance filter of tensio-active agent enriched layer with 0.45 μ m, reclaim tensio-active agent, filtrate is spin-dried for, and must comprise the crude extract of psoralen and isopsorapen.
In described step 1), the volumetric concentration of tensio-active agent is 15%, and liquid-solid ratio is at 150mL:1g, and extraction time is 30min;
Described step 2), in, add 2.5molL
-1Sodium-chlor under at 50 ℃ of water bath with thermostatic control balance 40min.
Described tensio-active agent comprises: anion surfactant, cats product, zwitterionics and nonionogenic tenside.
Described anion surfactant is stearic acid or Sodium dodecylbenzene sulfonate;
Cats product is quaternary ammonium compound;
Zwitterionics is Yelkin TTS, amino acid pattern, betaine type or ethoxylated dodecyl alcohol;
Nonionogenic tenside is Triton X-100, glycerin fatty acid ester, the lipid acid sorb is smooth or polysorbate.
Described ethoxylated dodecyl alcohol is GENAPOL X080.
Described Triton X-100 is Triton X-100, Triton X-114 or Triton X-45.
Described ionogen comprises vitriol, nitrate, hydrochloride, sulphite, carbonate, sulphite.
Described filtration ultra-filtration membrane is natural membranes or polymer membrane.
Compared with prior art, the present invention has following useful technique effect:
The method of extracting psoralen and isopsorapen based on cloud point extraction provided by the invention, the method, without poisonous and hazardous organic solvent, has increased extraction yield, has reduced environmental pollution, is suitable for industrialized extensive extraction.
Than using the methanol extraction method, at first, under same condition, effective constituent extraction efficiency of the present invention has clear superiority.Using GENAPOL X080 as extraction agent, and the percentage extraction of Psoralea corylifolia and isopsoralen is respectively 8.9 and 10.6mgg
-1, and the percentage extraction of methyl alcohol method is 6.4 and 9.1mgg
-1Moreover, in extracting operation, use hardly poisonous organic solvent, have environmental friendliness, advantage easy and simple to handle.
The method of extracting psoralen and isopsorapen based on cloud point extraction provided by the invention, also have following advantage: 1. percentage extraction is high; 2. economic environmental protection; 3. dosage of surfactant is few, and is easy to process; 4. activeconstituents volatility not; 5. easy and simple to handle; Time saving and energy saving; 6. with low cost.
The present invention extracts the cloud point extraction method for the industrialization of the effective constituents such as the Psoralea corylifolia of plant Psoralea corylifolia and different Psoralea corylifolia,, low toxicity efficient to obtain, easy extracting method.And, during the extraction that the method also can be generalized to the effective constituent of other plant separates, be of great significance for modernization of Chinese medicine tool.
The accompanying drawing explanation
Fig. 1 is the impact of the concentration of Genapol X-080 on extraction yield, and wherein X-coordinate is the concentration (%, v/v) of Genapol X-080, and ordinate zou is extraction yield.
Fig. 2 is the impact of liquid-solid ratio on extraction yield, and wherein X-coordinate is solid-to-liquid ratio, and ordinate zou is extraction yield;
Fig. 3 is the impact of sodium-chlor consumption on extraction yield, and wherein X-coordinate is the concentration of sodium-chlor, and ordinate zou is the rate of recovery;
Fig. 4 is the impact of equilibrium temperature on extraction yield, and wherein X-coordinate is equilibrium temperature, and ordinate zou is the rate of recovery;
Fig. 5 is the impact of starting time on extraction yield, and wherein X-coordinate is starting time, and ordinate zou is the rate of recovery;
Fig. 6 is the HPLC spectrogram of Psoralea corylifolia and different Psoralea corylifolia.
Embodiment
The present invention is described in further detail below in conjunction with specific embodiment, and the explanation of the invention is not limited.
The method of extracting psoralen and isopsorapen based on cloud point extraction provided by the invention, the cloud point extraction method of take is major technique, is aided with ultrasound assisted extraction technique and ultra-filtration technique, realizes separating of Psoralea corylifolia and different Psoralea corylifolia isoreactivity composition in the plant Psoralea corylifolia.Mainly comprise following operation:
From medicinal material by extracts active ingredients to the tensio-active agent liquid layer:
By Malaytea Scurfpea Fruit and surfactant soln, fully mix on vortex mixer; This is because psoralene, isopsoralen are fat-soluble cpdss, can not be by the solvent extraction of water isopolarity, but due to after having added and having formed tensio-active agent, form the micella of inner nonpolar outside polarity, so add the extraction that tensio-active agent can be realized the compounds such as Psoralea corylifolia afterwards; In order to make the abundant solubilising of this extracting solution, assisting ultrasonic is processed when extracting;
Again by effective constituent from tensio-active agent, filtering out:
After extraction completed, extract was centrifugal, and supernatant liquor adds ionogen regulator solution ionic strength, water bath with thermostatic control balance at a certain temperature, and centrifugal rear solution gets final product phase-splitting--be divided into aqueous layer and the tensio-active agent enriched layer of tensio-active agent; Wherein electrolytical adding can be so that the separating of two-phase with the rising temperature, under suitable electrolyte concentration, can obtain the highest percentage extraction, and when concentration increased again, surfactant layer floated on solution surface, make extract layer be difficult to form two-phase, thereby percentage extraction is reduced greatly; While only having simultaneously equilibrium temperature to reach the cloud point temperature of tensio-active agent used, system just can be divided into two-phase, and excess Temperature can cause composition to decompose;
After being divided into two-phase, tensio-active agent enriched layer ultrafiltration membrance filter, reclaim tensio-active agent, and filtrate is spin-dried for, and must comprise the fat-soluble class crude extract of psoralen and isopsorapen.
Concrete, the method based on cloud point extraction extraction psoralen and isopsorapen comprises the following steps:
1) after the Psoralea corylifolia plant powder is soaked in water, join certain density tensio-active agent, then on vortex mixer, fully mix, and 25 ℃ of lower 300W ultrasonic processor supersound process;
2) after having extracted, extract 3500rpm is centrifugal, and supernatant liquor adds ionogen regulator solution ionic strength, centrifugal after water bath with thermostatic control balance for some time, the solution layering: the aqueous layer and the tensio-active agent enriched layer that are divided into tensio-active agent;
3) by tensio-active agent enriched layer ultrafiltration membrance filter, reclaim tensio-active agent, filtrate is spin-dried for, and must comprise the crude extract of psoralen and isopsorapen.
Wherein, tensio-active agent comprises:
Anion surfactant: as stearic acid, Sodium dodecylbenzene sulfonate etc.;
Cats product: as quaternary ammonium compound etc.;
Zwitterionics: as Yelkin TTS, amino acid pattern, betaine type, ethoxylated dodecyl alcohol (GENAPOL X080) etc.;
Nonionogenic tenside: as Triton X-100 (Triton X series), glycerin fatty acid ester, the lipid acid sorb is smooth, polysorbate etc.;
Described ionogen comprises vitriol, nitrate, hydrochloride, sulphite, carbonate, sulphite etc.;
Described filtration is with synthetic films such as the natural membranes such as ultra-filtration membrane temperature microbial film or polymer membranes.
According to aforesaid operations, provide determining of some parameters in aforesaid operations below by embodiment:
The selection of embodiment 1 tensio-active agent
Attempted anion surfactant: as stearic acid, Sodium dodecylbenzene sulfonate etc.; Cats product: as quaternary ammonium compound etc.; Zwitterionics: as Yelkin TTS, amino acid pattern, betaine type, ethoxylated dodecyl alcohol (GENAPOL X080) etc.; Nonionogenic tenside: as Triton X-100 (Triton X series), glycerin fatty acid ester, the lipid acid sorb is smooth, polysorbate etc.;
Result shows that above-mentioned tensio-active agent all is applicable to extract based on cloud point extraction the method for psoralen and isopsorapen, wherein the extraction effect of GENAPOL X080 is best, may be because GENAPOL X080 is a kind of lard type tensio-active agent that does not contain aromatic nucleus, under 210nm, without uv-absorbing, can not disturb the assay of Psoralea corylifolia and different Psoralea corylifolia.
In following embodiment, adopt the tensio-active agent of GENAPOL X080 as cloud point extraction.
The impact of embodiment 2 surfactant concentrations on the psoralen and isopsorapen extraction efficiency.
In the situation that other extraction conditions are constant, surfactant concentration changes on the impact of psoralen and isopsorapen extraction efficiency as shown in Figure 1, wherein, psoralen is the change curve of the extraction efficiency of psoralene, and ispsoralen is the change curve of isopsoralen extraction efficiency;
Can find out, when surfactant concentration is increased to 15% (v/v, volume ratio), the extraction yield increase of psoralene, isopsoralen from 1.0%, and surfactant concentration is while being increased to 20% from 15%, although its extraction yield increase to some extent change not remarkable.And after surfactant concentration was increased to 20%, extraction yield continue to increase, but viscosity also increase, be difficult to process, so, under this condition, adopt 10～15% tensio-active agents as the optimum condition extracted, wherein 15% is top condition.
Implement the extraction recovery impact of 3 liquid-solid ratioes on psoralen and isopsorapen.
In the situation that other extraction conditions are constant, investigate the extraction yield impact of liquid-solid ratio on psoralen and isopsorapen, wherein liquid-solid ratio refers to tenside/solvent used and the ratio between Malaytea Scurfpea Fruit, is another key factor that affects extraction efficiency.As shown in Figure 2, preferably liquid-solid ratio is at 50:1～400:1(mL/g) for result, and when 150:1 (15mL/0.1g), extraction efficiency is the highest when liquid-solid ratio.
The impact of 4 ultrasonic extraction times of embodiment on recovery of extraction
In the situation that other extraction conditions are constant, the ultrasonic auxiliary extraction time of 5-60min is investigated.During at 30min, the percentage extraction of psoralen and isopsorapen is the highest when the time, if, more than the time extends to 35min again, may be because effective constituent is easy to change under long-time ultrasonic state.So, in following embodiment step, all adopt 30min as the ultrasonic dissolution assisting time.
Electrolytical adding can be so that the separating of two-phase with the rising temperature, so investigated the impact on percentage extraction of starting time in the experiment, equilibrium temperature, electrolytical consumption.
The impact of embodiment 5 ionogen consumptions
In the present embodiment, select sodium-chlor.In the situation that other conditions are constant, under 50 ℃ of equilibrium temperatures, starting time is 30min, investigates concentration at 1.0-5.0molL
-1The impact of sodium chloride solution on extraction yield.When ionic strength increased, the micella particle diameter increased, and it is constant that micelle-forming concentration keeps.
As can be seen from Figure 3,2.5molL
-1Salt concn under can obtain the highest percentage extraction.When concentration increased again, surfactant layer floated on solution surface, makes extract layer be difficult to form two-phase, thereby percentage extraction is reduced greatly.So, 2.5～3molL
-1For optimum condition, 2.5molL
-1Sodium chloride solution under obtain optimum ionic strength.
The impact of embodiment 6 equilibrium temperatures on recovery of extraction
In this extracting process, while only having equilibrium temperature to reach the cloud point temperature of tensio-active agent used, system just can be divided into two-phase, and excess Temperature can cause composition to decompose, and adopts and can realize two minimum temperatures that are separated so need.From theory, be generally to adopt to be advisable higher than 20 ℃ of tensio-active agent cloud point temperature 10 –, yet Fig. 4 has shown the relation of percentage extraction and equilibrium temperature, at the temperature of 50 ℃, has obtained the highest extraction efficiency.
The impact of embodiment 7 starting times on extraction efficiency.
In the situation that other extraction conditions are constant, the variation of percentage extraction under having attempted from 20min to 60min, in the situation that determine 50 ℃ of equilibrium temperatures, as shown in Figure 5, arrive 40min at 20min, time lengthening, percentage extraction increases, but the time extends to 50min, percentage extraction decline again, so, in 35～45min scope, can obtain the highest extraction yield.
Comprehensive above embodiment conditional filtering is as can be known, and the extraction conditions of optimization is:
1) the Psoralea corylifolia plant powder being joined to volumetric concentration is in 10～15% surfactant soln, wherein liquid-solid ratio is 150mL:1g～200mL:1g, on vortex mixer, fully mix, and under 25 ℃, 300W ultrasonic processor supersound process auxiliary under, extract 30～35min;
2) after having extracted, extract is centrifugal, and supernatant liquor adds ionogen regulator solution ionic strength, and wherein electrolyte concentration is 2.5～3molL
-1, centrifugal after 50 ℃ of water bath with thermostatic control balance 35～45min, solution layering: the aqueous layer and the tensio-active agent enriched layer that are divided into tensio-active agent;
3) by tensio-active agent enriched layer ultrafiltration membrance filter, reclaim tensio-active agent, filtrate is spin-dried for, and must comprise the crude extract of psoralen and isopsorapen.
Further optimum condition is:
Adopt GENAPOL X080 as tensio-active agent, the volumetric concentration of tensio-active agent is 15%, and liquid-solid ratio is at 150mL:1g, ultrasonic auxiliary extraction 30min; And add 2.5molL
-1Sodium-chlor under at 50 ℃ of balance 40min; The recovery of extraction of the psoralen and isopsorapen extracted is respectively: 79.37 ± 1.79% and 76.54 ± 1.04% (n=6).
Detection to the psoralen and isopsorapen that extracts:
1) crude extract is measured and slightly put forward efficiency by the HPLC method.
Under the chromatographic condition of pharmacopeia, the retention time of Psoralea corylifolia and different Psoralea corylifolia is respectively 10.6min and the 12.7min. retention factors is respectively 6.75 and 9.04, as shown in Figure 6.
Chromatographic condition:
Chromatographic column: Diamonsil C18 post (150mm * 4.6mm, 5 μ m);
Moving phase: methanol-water 55:45;
Detect wavelength: 246nm;
Flow: 1.0mLmin
-1
Column temperature: 30 ℃;
Sample size: 10 μ L.
2) with traditional extracting method extraction efficiency relatively
Than using the methanol extraction method, under same condition, effective constituent extraction efficiency of the present invention has clear superiority.Using GENAPOL X080 as extraction agent, and the percentage extraction of Psoralea corylifolia and isopsoralen is respectively 8.9 and 10.6mgg
-1, and the percentage extraction of methyl alcohol method is 6.4 and 9.1mgg
-1.
Claims (9)
1. a method of extracting psoralen and isopsorapen based on cloud point extraction, is characterized in that, comprises following operation:
1) by Malaytea Scurfpea Fruit with after surfactant soln fully mixes, and extract under ultrasound condition;
2) extracted rear collection extracting solution, centrifugal, collect supernatant liquor and add ionogen to regulate ionic strength, then in the water bath with thermostatic control balance, aqueous layer and tensio-active agent enriched layer that centrifugal rear supernatant liquor phase-splitting is tensio-active agent;
3) after being divided into two-phase, tensio-active agent enriched layer ultrafiltration membrance filter, reclaim tensio-active agent, and filtrate is spin-dried for, and obtains comprising the fat-soluble class crude extract of psoralen and isopsorapen.
2. the method for extracting psoralen and isopsorapen based on cloud point extraction as claimed in claim 1, is characterized in that, specifically comprises the following steps:
1) the Psoralea corylifolia plant powder being joined to volume-fraction concentration is in 10～15% surfactant soln, wherein liquid-solid ratio is 150mL:1g～200mL:1g, in vortex mixer, fully mix, and, under 25 ℃, under 300W ultrasonic processor supersound process, extract 30～35min;
2) extracted rear collection extracting solution, centrifugal, collect supernatant liquor and add ionogen and regulate ionic strength, wherein electrolyte concentration is 2.5～3molL
-1, then centrifugal after 50 ℃ of water bath with thermostatic control balance 35～45min, the supernatant liquor phase-splitting is aqueous layer and the tensio-active agent enriched layer of tensio-active agent;
3) by the ultrafiltration membrance filter of tensio-active agent enriched layer with 0.45 μ m, reclaim tensio-active agent, filtrate is spin-dried for, and must comprise the crude extract of psoralen and isopsorapen.
3. the method for extracting psoralen and isopsorapen based on cloud point extraction as claimed in claim 2, is characterized in that, in described step 1), the volumetric concentration of tensio-active agent is 15%, and liquid-solid ratio is at 150mL:1g, and extraction time is 30min;
Described step 2), in, add 2.5molL
-1Sodium-chlor under at 50 ℃ of water bath with thermostatic control balance 40min.
4. the method for extracting psoralen and isopsorapen based on cloud point extraction as claimed in claim 1 or 2, it is characterized in that, described tensio-active agent comprises: anion surfactant, cats product, zwitterionics and nonionogenic tenside.
5. the method for extracting psoralen and isopsorapen based on cloud point extraction as claimed in claim 4, is characterized in that, described anion surfactant is stearic acid or Sodium dodecylbenzene sulfonate;
Cats product is quaternary ammonium compound;
Zwitterionics is Yelkin TTS, amino acid pattern, betaine type or ethoxylated dodecyl alcohol;
Nonionogenic tenside is Triton X-100, glycerin fatty acid ester, the lipid acid sorb is smooth or polysorbate.
6. the method for extracting psoralen and isopsorapen based on cloud point extraction as claimed in claim 5, is characterized in that, described ethoxylated dodecyl alcohol is GENAPOL X080.
7. the method for extracting psoralen and isopsorapen based on cloud point extraction as claimed in claim 5, is characterized in that, described Triton X-100 is Triton X-100, Triton X-114 or Triton X-45.
8. the method for extracting psoralen and isopsorapen based on cloud point extraction as claimed in claim 1 or 2, is characterized in that, described ionogen comprises vitriol, nitrate, hydrochloride, sulphite, carbonate, sulphite.
9. the method for extracting psoralen and isopsorapen based on cloud point extraction as claimed in claim 1 or 2, is characterized in that, described filtration ultra-filtration membrane is natural membranes or polymer membrane.
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| CN105017273A (en) * | 2015-07-27 | 2015-11-04 | 徐州医学院 | Method for extracting, separating and purifying psoralen and isopsoralen from fructus psoraleae |
| CN113226345A (en) * | 2019-01-04 | 2021-08-06 | D-自然株式会社 | Selective extraction method of natural substance |
| JP2022518111A (en) * | 2019-01-04 | 2022-03-14 | ディーネイチャー カンパニー リミテッド | Selective extraction method of natural substances |
| EP3888668A4 (en) * | 2019-01-04 | 2023-01-04 | D-Nature Co., Ltd. | Selective extraction method for natural substances |
| CN113226345B (en) * | 2019-01-04 | 2023-10-03 | D-自然株式会社 | Selective extraction method of natural substances |
| CN113945651A (en) * | 2021-09-26 | 2022-01-18 | 兰州石化职业技术学院 | Method for extracting ferulic acid from angelica sinensis by using non-ionic surfactant and application of ferulic acid |
| CN115014890A (en) * | 2022-05-18 | 2022-09-06 | 深圳职业技术学院 | Sample processing method and method for measuring nitrofuran metabolite |
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