CN102731460A - Method for separating and purifying cajanol from pigeon pea rhizomes - Google Patents
Method for separating and purifying cajanol from pigeon pea rhizomes Download PDFInfo
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- CN102731460A CN102731460A CN2011100915613A CN201110091561A CN102731460A CN 102731460 A CN102731460 A CN 102731460A CN 2011100915613 A CN2011100915613 A CN 2011100915613A CN 201110091561 A CN201110091561 A CN 201110091561A CN 102731460 A CN102731460 A CN 102731460A
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Abstract
The invention relates to a method for separating and purifying the active ingredient cajanol from pigeon pea rhizomes. The invention aims to provide a simple, secure, and cost-effective method for extracting, separating and purifying high purity cajanol from pigeon pea rhizomes. The invention adopts the following technical solution of: taking fresh or dry pigeon pea rhizomes as raw materials, employing a homogenate induction technology, an enzyme induction technology, a solvent extraction technology, an ultrasonic oscillation flocculation technology, a negative pressure cavitation suspension liquid solid extraction technology, a macroporous adsorption resin enrichment technology, a normal phase silica gel medium pressure column chromatography separation technology, and low temperature crystallization as well as recrystallization technologies, etc. so as to obtain refined cajanol with purity over 95%. The method of the invention has the advantages of easy and practicable process, high yield, and high purity and high value-added product, thus being suitable for industrial production.
Description
Technical field
The present invention relates to the method for extraction from plant, separation and purifying activeconstituents, specifically is extraction the fresh or exsiccant rhizome, separation and purifying cajanol from pigeonpea.
Background technology
Cajanol belongs to flavonoid compound, is that a kind of good antiseptic-germicide has anticancer effect simultaneously again.It all has stronger resistance to staphylococcus epidermidis, streptococcus aureus, subtilis, intestinal bacteria, Bacillus proteus, Pseudomonas aeruginosa; Can suppress intestinal bacteria through infringement DNA, and mainly be to suppress streptococcus aureus and increase (Liu Xiao-lei 2010) through acting on Yelkin TTS, phosphoric acid salt and DNA on the film to the anti-microbial effect of streptococcus aureus.In addition, cajanol can also be in vitro inhibition gram positive bacterium and gram negative bacterium growth.Except antibacterial effect, cajanol also has stronger anticancer effect, and cajanol can show resistance to the MCF-7 cell; Show concentration simultaneously and rely on, cajanol descends the MCF-7 cell survival rate, causes cell to block the phase in G2/M; And cell death inducing; Cajanol inductive apoptosis is through the plastosome dependent pathway, comprises outside the induced expression desintegrate mitochondrial membrane of the expression that suppresses Bcl-2 and Bax, and causes cytochrome c release.Therefore, cajanol has the excellent development prospect as a kind of potential pharmaceutical compound.According to our present discovering, cajanol exists only in the pigeonpea root, and content is higher.
Pigeonpea is to belong to annual or perennial woody plant, evergreen shrubs for the pulse family pigeonpea.Having another name called pigeon beans, tree soya bean etc., is a kind of medication among the people." Luchuan book on Chinese herbal medicine " record: Leaf of Cajan " flat, light, slightly poisonous "." Chinese medicine sea " done to further specify to this: Leaf of Cajan " flat, light, slightly poisonous, go into heart footpath " cures mainly children's's varicella, pain swells.Pigeonpea has in addition that clearing heat and detoxicating, invigorating the spleen and replenishing QI, Li Shui help digestion in addition, hemostasis and dysentery-stopping, the addiction pain relieving of loosing, the swollen effect of row's pain.Yet the research for pigeonpea at present concentrates on the research to Leaf of Cajan, the research of pigeonpea root is but reported less, and the pharmaceutical use of many pigeonpea roots does not obtain embodying.
In sum, cajanol is a kind of activity Flavonoid substances preferably, and its good antibacterial activity and anti-tumor activity make it very likely become a kind of potential pharmaceutical compound.But up to the present extraction, separation and the purifying process for cajanol do not appear in the newspapers as yet, and simultaneously, a large amount of pigeonpea Root Resources is all burnt as agricultural wastes, has not only consumed resource and has also destroyed environment.Therefore; The present invention is intended to set up a kind of through the combination of various modern separating and purifying technology; The method of separation cajanol rapidly and efficiently; Make the resource of pigeonpea root obtain rationally utilizing efficiently, give full play to the value of pigeonpea root, and to obtain highly purified cajanol sample be that scientific research and industrial production are supplied raw materials.
Summary of the invention
The object of the present invention is to provide that a kind of fresh or exsiccant rhizome is a raw material with pigeonpea; Through homogenate inductive technology, enzyme induction technology, solvent extraction techniques, ultra-sonic oscillation flocculation technique, negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction technology, macroporous adsorbent resin beneficiation technologies, purification on normal-phase silica gel medium pressure column chromatography stripping technique and low temperature crystallization and recrystallization technology; Thereby obtain the cajanol monomer in a large number, fast, this method is simple, the target compound loss is few.The objective of the invention is to reach through following scheme:
Pigeonpea is fresh or exsiccant root process water homogenate system is induced, enzymic hydrolysis; Can improve cajanol content; After the 60-85% alcohol solvent extracts, extract adds entry in 30-45 ℃ of ultra-sonic oscillation, static flocculation, and resultant throw out obtains the product of cajanol behind negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction, Amberlyst process enrichment and purification on normal-phase silica gel medium pressure column chromatography; Purity is greater than 80%, obtains purity greater than 95% pure article through low temperature crystallization and recrystallization.
Above-mentioned cajanol extracting and purifying method is characterized in that, get a certain amount of fresh or exsiccant pigeonpea root and add entry, temperature 30-45 ℃, volume be solid masses 3-8 doubly, homogenate is induced 3 times continuously, each 1-10 minute; In leaching process, use enzyme that fresh or dry pigeonpea root is induced hydrolysis; Slurries after homogenate induced use Hydrocerol A, Glacial acetic acid min. 99.5 or hydrochloric acid to transfer pH to be 3.0-6.0; Get 0.2-2% solid substance weight cellulase, polygalacturonase, glucuroide any two or three form prozyme, be dissolved in the damping fluid that pH is 3.0-6.0, in 50-60 ℃ of water-bath, activate 8-15 minute; Prozyme damping fluid after activating being added homogenate induce in the slurries, is in 30-50 ℃ the water-bath enzymolysis 3-6 hour in temperature; Material that ethanol extract is carried be homogenate induce with enzyme induction after solid substance, process for extracting is selected from that ultrasonic-assisted extraction, cold soaking are extracted, supercritical CO
2Extract or the microwave-assisted extraction; Induce the back solid substance to use the 60-85% extraction using alcohol; After induced liquid and ethanol extract merging concentrate, add entry in the pigeonpea root extract, extract is added 40-50 ℃ of warm water of 3-6 times of volume; Vibration was flocculated 15-30 minute under the 50-60KHz condition in the ultrasonic oscillation extraction device; Static 15-30 minute, hyperacoustic concussion effect made the bigger impurity stripping gradually of polarity that comprises in the thickness throw out, the throw out enrichment 90～99% cajanol in the extracting solution.Obtain throw out; With the 0.03-0.06MPa negative pressure is that power carries out the negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction with organic solvent; Every gram crude extract adds extraction solvent 5mL-20mL; Extraction times is 5-8 time, and solvent for use is a kind of in ETHYLE ACETATE, trichloromethane or the methylene dichloride, and organic phase can get the target solid substance after reclaiming solvent; Concentrated extract is to doing; The solid substance that obtains is with 20-30% ethanol suspendible, and being configured to feed concentration is 2-4mg/mL suspendible soup, simultaneously macroporous adsorbent resin is adopted wet method dress post; Keep liquid level; With the soup of suspendible through adsorption column, applied sample amount 0.5-1BV, with flow velocity for per hour 6-8mL/g resin, pH=5 condition were descended adsorption column.Impurity is washed with 30-40% ethanol 3BV in the absorption back, uses 50-60% ethanol 8-10BV desorb then.Collect desorbed solution, be concentrated into the dried solid substance that obtains.Taking by weighing quality in advance is the 5-10 silica gel doubly of extract quality, adopts wet method dress post, and solvent for use also comprises normal hexane except that sherwood oil.The gained solid substance is used a small amount of organic solvent dissolution, add with the medicinal extract mass ratio be that 1: 1.2 chromatographic silica gel mixes, reduces pressure that it is dried to revolve thoroughly, compression leg in the purification on normal-phase silica gel of packing into.Successively with 10-20BV sherwood oil, sherwood oil: ETHYLE ACETATE=10: 1, sherwood oil: compress and wash during ETHYLE ACETATE=5: 1, methyl alcohol compress and wash in continuously and takes off continuously and take off, collect elutriant, every part of 1/40-1/20BV.Flow point is collected in the TLC monitoring, merges same section, and developping agent is a sherwood oil: ETHYLE ACETATE=10: 1-2: 1, and ultraviolet wavelength is 254nm and 365nm.Obtain cajanol solution, the low temperature crystallization obtains product, obtains pure article behind the recrystallization.
The used macroporous adsorbent resin of the extracting and purifying method of cajanol is D101, NKA-9, NKA-2, AB-8, AL-9, H103, ADS-7, ADS-8, ADS-17 or ADS-21 in the above-mentioned pigeonpea.
Advantage of the present invention:
1. the present invention is a raw material with the fresh or dry pigeonpea root that in agriculture prodn, mostly goes out of use, and has improved the use value of this agricultural plants of pigeonpea, reasonable use resource, have actively and profound significance for the development and utilization of pigeonpea.
2. adopt advanced homogenate inductive technology, enzymic hydrolysis technology, solvent extraction techniques, ultra-sonic oscillation flocculation technique, negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction technology, macroporous adsorbent resin beneficiation technologies, purification on normal-phase silica gel medium pressure column chromatography stripping technique and low temperature crystallization and recrystallization technology to be used for inducing of cajanol and extraction separation in the invention, the products obtained therefrom yield is high, purity is high.
3. method therefor of the present invention is high in technological content, and the cycle is short, and consumption of organic solvent is few, and environmental pollution is little, and energy consumption is low, and cost is low, and simultaneously, the present invention can realize large-scale industrialized production.
Description of drawings
Fig. 1 is the structure of cajanol
Fig. 2 is the separation and purification schema
Embodiment
Instance 1
Take by weighing pigeonpea dry root 1000g, tentatively pulverize, continuous homogenate is induced 3 times behind 40 ℃ of warm water of 8 times of volumes of adding, and each 5 minutes, the slurries use Glacial acetic acid min. 99.5 accent pH that homogenate is induced was 4.0; Get the prozyme that the cellulase, polygalacturonase, glucuroide of 0.5% solid substance weight are formed according to mass ratio at 1: 1: 1, be dissolved in pH and be in 4.0 the damping fluid, in 40 ℃ of water-baths, activate 8 minutes; Prozyme damping fluid after activating being added homogenate induce in the slurries, is enzymolysis 6 hours in 45 ℃ the water-bath in temperature.Induced liquid separates the back solid substance and uses 70% extraction using alcohol, after induced liquid and ethanol extract merging concentrate extract is added in 40 ℃ of warm water, and volume is 4.5L; Vibration was flocculated 20 minutes under the 50-60KHz condition in the ultrasonic extraction device; Static 15 minutes, get throw out, be that power carries out the negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction with 13.5L ETHYLE ACETATE with the 0.05MPa negative pressure; Concentrated extract; Being configured to feed concentration with 30% ethanol is 4mg/mL suspendible soup, applied sample amount 0.8BV, and flow velocity is for per hour 8mL/g resin, pH=5 condition descended NKA-9 type macropore to cross adsorption resin column.Impurity is washed with 30% ethanol 3BV in the absorption back, uses 50% ethanol 10BV desorb then.Collect stripping liquid, be concentrated into and do the back with the small amount of methanol dissolving, add with the medicinal extract mass ratio be that 1: 1.2 order number is that the chromatographic silica gel of 500-800 is mixed thoroughly, 50 ℃ of evaporated under reduced pressure.Take by weighing the 500-800 order silica gel of 7 times of extract qualities in advance; Adopt sherwood oil wet method dress post, during the silica gel of having mixed sample is packed in the compression leg: compress and wash during ETHYLE ACETATE=5: 1, methyl alcohol compress and wash in continuously and takes off continuously and take off successively with 15BV sherwood oil, sherwood oil: ETHYLE ACETATE=10: 1, sherwood oil; Flow point is collected in the TLC monitoring; Concentrate and to obtain the cajanol bullion, with sherwood oil: the mixed solvent of ETHYLE ACETATE=5: 1 is cajanol 15 ℃ of following crystallizations to compound; 43.21mg purity is 95%.
Instance 2
Take by weighing fresh pigeonpea root 2000g, tentatively pulverize, continuous homogenate is induced 3 times behind 45 ℃ of warm water of 6 times of volumes of adding, and each 3 minutes, the slurries use Glacial acetic acid min. 99.5 accent pH that homogenate is induced was 4.5; Get the prozyme that the cellulase, polygalacturonase, glucuroide of 0.4% solid substance weight are formed according to mass ratio at 1: 1: 1, be dissolved in pH and be in 4.5 the damping fluid, in 45 ℃ of water-baths, activate 8 minutes; Prozyme damping fluid after activating being added homogenate induce in the slurries, is enzymolysis 6 hours in 45 ℃ the water-bath in temperature.Induced liquid separates the back solid substance and uses 70% extraction using alcohol, after induced liquid and ethanol extract merging concentrate extract is added in 40 ℃ of warm water, and volume is 4.5L; Vibration was flocculated 15 minutes under the 50-60KHz condition in the ultrasonic extraction device; Static 15 minutes, get throw out, be that power carries out the negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction with 10L ETHYLE ACETATE with the 0.055MPa negative pressure; Concentrated extract; Being configured to feed concentration with 30% ethanol is 4.5mg/mL suspendible soup, applied sample amount 0.8BV, and flow velocity is for per hour 8mL/g resin, pH=5 condition descended AB-8 type macropore to cross adsorption resin column.Impurity is washed with 30% ethanol 3BV in the absorption back, uses 50% ethanol 10BV desorb then.Collect stripping liquid, be concentrated into and do the back with the small amount of methanol dissolving, add with the medicinal extract mass ratio be that 1: 1.2 order number is that the chromatographic silica gel of 500-800 is mixed thoroughly, 50 ℃ of evaporated under reduced pressure.Take by weighing the 500-800 order silica gel of 8 times of extract qualities in advance; Adopt sherwood oil wet method dress post, during the silica gel of having mixed sample is packed in the compression leg: compress and wash during ETHYLE ACETATE=5: 1, methyl alcohol compress and wash in continuously and takes off continuously and take off successively with 15BV sherwood oil, sherwood oil: ETHYLE ACETATE=10: 1, sherwood oil; Flow point is collected in the TLC monitoring; Concentrate and to obtain the cajanol bullion, with normal hexane: the mixed solvent of ETHYLE ACETATE=2: 1 is 20 ℃ of following crystallizations, and obtaining compound is cajanol; 38.75mg purity is 97%.
Claims (9)
1. from the pigeonpea root, separate and the method for purifying cajanol, may further comprise the steps:
(1) induce and enzymic hydrolysis: the pigeonpea root is induced through the homogenate inductive technology, again through the hydrolysis of enzymic hydrolysis technology to increase the content of free cajanol;
(2) extract: induce with hydrolysis after solid matter through the 60-85% extraction using alcohol; Induce with hydrolyzed solution and ethanol extract and merge the water ultra-sonic oscillation flocculation that concentrates 40-50 ℃ of back adding; Static, obtain throw out, with throw out through the liquid-solid extraction of organic solvent negative pressure-cavitation homogenous solid-liquid phase;
(3) separate: the raw product that extraction is obtained after the solution concentration carrying out obtaining behind enrichment and the purification on normal-phase silica gel medium pressure column chromatography through macroporous adsorbent resin cajanol;
(4) crystallization: the raw product of cajanol is obtained purity greater than 95% pure article through low temperature crystallization and recrystallization.
2. according to the described method of from the pigeonpea root, separating with purifying cajanol of claim 1, it is characterized in that the described pigeonpea root origin of step (1) produces the fresh or exsiccant root of pigeonpea in Hainan, pass through pulverization process.
3. from the pigeonpea root, separate and the method for purifying cajanol according to claim 1 is described, it is characterized in that the described homogenate inductive technology of step (1), used solvent is a water; Temperature 30-45 ℃; Volume is 3-8 a times of solid masses, and homogenate is induced 3 times continuously, each 1-10 minute; The described enzymic hydrolysis technology of step (1); Slurries after at first homogenate being induced use Hydrocerol A, Glacial acetic acid min. 99.5 or hydrochloric acid to transfer pH to be 3.0-6.0; Get the prozyme that any two or three in cellulase, polygalacturonase and the glucuroide of 0.2-2% solid substance weight formed then; Be dissolved in the damping fluid that pH is 3.0-6.0, in 50-60 ℃ of water-bath, activate 8-15 minute; Prozyme damping fluid after activating being added homogenate induce in the slurries, is in 30-50 ℃ the water-bath enzymolysis 3-6 hour in temperature.
4. from the pigeonpea root, separate and the method for purifying cajanol according to claim 1 is described; It is characterized in that the described ethanol extract of step (2); Material that ethanol extract is carried be homogenate induce with enzymic hydrolysis after solid substance, process for extracting is selected from that ultrasonic-assisted extraction, cold soaking are extracted, supercritical CO
2Extraction, microwave-assisted extract, and solvent for use is a 60-85% ethanol.
5. from the pigeonpea root, separate and the method for purifying cajanol according to claim 1 is described; It is characterized in that the described ultra-sonic oscillation flocculation technique of step (2), add entry in the pigeon pea rhizome extract, temperature 40-50 ℃; Volume is 3-6 a times of extract quality; The ultra-sonic oscillation flocculation time is 15-30 minute, and frequency is 50-60KHz, and be 15-30 minute rest time.
6. from the pigeonpea root, separate and the method for purifying cajanol according to claim 1 is described; It is characterized in that the described negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction of step (2) technology, throw out is carried out the negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction, used organic solvent is a kind of in ETHYLE ACETATE, trichloromethane or the methylene dichloride; Every gram crude extract adds extraction solvent 5mL-20mL; Extraction times is 5-8 time, and used pressure is 0.03-0.06MPa, and organic phase can get the target solid substance after reclaiming solvent.
7. from the pigeonpea root, separate and the method for purifying cajanol according to claim 1 is described; It is characterized in that the described macroporous adsorbent resin enriching method of step (3); Used resin is selected from D101, NKA-9, NKA-2, AB-8, AL-9, H103, ADS-7, ADS-8, ADS-17 or ADS-21 macroporous adsorbent resin, and the macroporous resin adsorption step adopts wet method dress post in this method, keeps liquid level; Partly use the 20-30% ethanolic soln to be mixed with feed concentration the resulting solid substance of negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction and be 2-4mg/mL suspendible soup; Simultaneously macroporous adsorbent resin is adopted wet method dress post, keep liquid level, the soup of suspendible is passed through adsorption column; Applied sample amount is 0.5-1BV, with flow velocity for per hour 6-8mL/g resin, pH=5 condition were descended adsorption column; Impurity is washed with 30-40% ethanol 3BV in the absorption back, uses 50-60% ethanol 8-10BV desorb then; Collect stripping liquid, be concentrated into driedly, the gained solid substance is thick title product.
8. from the pigeonpea root, separate and the method for purifying cajanol according to claim 1 is described; It is characterized in that the described disposable purification on normal-phase silica gel medium pressure column chromatography technology of step (3); Purification on normal-phase silica gel medium pressure column chromatography specimen in use is a gained solid substance behind the resin concentration, and used silica gel is the 300-800 order; Taking by weighing quality in advance is the 5-10 silica gel doubly of sample size, adopts sherwood oil, normal hexane or ETHYLE ACETATE wet method dress post, and sample is dissolved with small amount of methanol, and adding is 1 with the medicinal extract mass ratio; 1.2 chromatographic silica gel mix, reduce pressure that it is dried to revolve thoroughly, in the pre-packed silicagel column of packing into; Successively with 10-20BV sherwood oil, sherwood oil: ETHYLE ACETATE=10: 1, sherwood oil; ETHYLE ACETATE=5: 1, methyl alcohol compress and wash in continuously and take off, and collect elutriant, every part of 1/40-1/20BV; Detect the elutriant composition with silica gel thin-layer chromatography, merge same section, developping agent is a trichloromethane; Methyl alcohol=30: 1-1: 1, ultraviolet wavelength is 254nm and 365nm.
9. from the pigeonpea root, separate and the method for purifying cajanol according to claim 1 is described; It is characterized in that described low temperature crystallization of step (4) and recrystallization technology; The recrystallization solvent for use is a kind of according to 50 in a kind of and trichloromethane, methylene dichloride, ETHYLE ACETATE, acetone, second eyeball or the methyl alcohol in sherwood oil, ether or the normal hexane: 1-1: the mixed solvent that 1 ratio is formed, the low temperature recrystallization temperature is-10 ℃-25 ℃.
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Cited By (1)
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| CN104016844A (en) * | 2013-02-28 | 2014-09-03 | 东北林业大学 | Method for separating and purifying chimaphilin from pyrola incarnate extract |
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| CN104016844B (en) * | 2013-02-28 | 2015-11-18 | 东北林业大学 | A kind of method of separation and purification chimaphilin from Herba Pyrolae incarnatae extract |
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Application publication date: 20121017 |