CN101973974A - Preparation method of chrysoeriol - Google Patents
Preparation method of chrysoeriol Download PDFInfo
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- CN101973974A CN101973974A CN2010102358997A CN201010235899A CN101973974A CN 101973974 A CN101973974 A CN 101973974A CN 2010102358997 A CN2010102358997 A CN 2010102358997A CN 201010235899 A CN201010235899 A CN 201010235899A CN 101973974 A CN101973974 A CN 101973974A
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- chrysoeriol
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Abstract
The invention provides a preparation method of chrysoeriol. A high-purity chrysoeriol product is obtained by the steps of alkali extraction and water precipitation, organic solvent extraction, membrane concentration, macroporous resin adsorption, and the like. In a membrane separation process, not only the product purity is improved, but also the damage to resin is alleviated, and the service life of the resin is prolonged; and by adopting crystallization and recrystallization, the purification efficiency is high. The whole preparation process has the advantages that requirements on environment and equipment are low, extraction and separation time is short, purity is high and the preparation method is simple and easy to operate.
Description
Technical field:
The invention belongs to field of medicine and chemical technology, relate to a kind of preparation method of chrysoeriol.
Background technology:
Chrysoeriol, justice name Jin Shengcao (Huang) element,
English name: Chrysoeriol, molecular formula: C
16H
12O
6Molecular weight: 300.26;
Molecular structural formula:
Chrysoeriol is a pale yellow powder, mp.320-322 ℃ (mp.336-337 ℃ of report also arranged).Be soluble in the organic solvents such as chloroform, vinyl acetic monomer.
Medicine turns usefulness into: antitumor (suppress 3, the carcinogenesis of 4-benzopyrene suppresses the benzopyrene metabolism); Cell toxicant (P388, ED
50=1.9 μ g/ml); CAMP phosphodiesterase inhibitor (in vitro, IC
50=269 μ mol/L); Antianaphylaxis resistance scorching (suppress basophilic leukocyte and discharge histamine, suppress neutrophil cell and discharge GRD beta-glucuronidase); Aldose reductase inhibitor (10 μ mol/L inhibiting rate 31.3%); Xanthine oxidase inhibitor (50 μ g/ml inhibiting rates 61.5%, IC
50=14.0 μ mol/ml); Anti-short coagulating (suppressed the expression of interleukin I inductive person monocytic cell tissue factor, IC
50=2.6 μ mol/L); Anticomplement.
Chrysoeriol all has separation to obtain in plants such as Herba Vernoniae Cinereae, betel nut fruit, lotus leaf, Evergreen Dogwood, the mugwort that withers, Cephalotaxus fortunei, tree peony seed, celery seed.But have not yet to see the report of chrysoeriol extracting and preparing technique, mainly be in the plant chemical ingredient research process to its composition slightly extract, behind the organic solvent extraction repeatedly silica gel column chromatography separate, and determine that by mass spectroscopy institute gets compound structure, it is lower that this method is separated the chrysoeriol extraction yield that obtains, and loses bigger.
Summary of the invention:
The preparation method who the purpose of this invention is to provide a kind of chrysoeriol obtains highly purified chrysoeriol, thereby makes it as the further investigation of chrysoeriol and the raw material of medicine and healthcare products.
Steps such as the present invention is heavy by the alkali water lift, organic solvent extraction, membrane concentration, macroporous resin enrichment, crystallization and recrystallization can obtain highly purified chrysoeriol product.
A kind of preparation method of chrysoeriol is characterized in that may further comprise the steps:
1) get the medicinal material that contains chrysoeriol, pulverize, use buck supersound extraction 0.5-3 hour, filter, concentrate, to neutral, centrifugal with acid accent pH, the precipitation adding distil water is made suspension liquid;
2) add ethyl acetate extraction again, combining extraction liquid after suspension liquid being added chloroform extraction;
3) above-mentioned extraction liquid is carried out micro-filtration, ultrafiltration and nanofiltration successively in the multifunctional membrane separating device;
4) above-mentioned stoste through nanofiltration is passed through macroporous resin, elder generation is washed till closely colourless with deionized water, discard water lotion, use the aqueous ethanolic solution gradient elution again, with the volume ratio of ethanol in aqueous ethanolic solution, by 30% ethanol, interval 10% is incremented to 90% successively, collects elutriant;
5) with above-mentioned elutriant decompression recycling ethanol, concentrate, drying is with 50% methyl alcohol heating for dissolving, cooling, standing over night are separated out crystallization, filter, get the chrysoeriol crude product, use ethyl acetate, methyl alcohol, acetone, chloroform or their mixing solutions recrystallization again, get the pure product of chrysoeriol.
The described medicinal material that contains chrysoeriol of step 1) is the mugwort that withers, Lonicera confusa DC., Evergreen Dogwood, tree peony seed, Herba Vernoniae Cinereae, celery seed, lotus leaf, etc.
The optional ammoniacal liquor of the described buck of step 1), sodium hydroxide solution, pH is 9-12, consumption is 4-15 a times of quality of medicinal material, extracts 40-60 ℃ of temperature.
The used acid of step 1) is hydrochloric acid, acetic acid, phosphoric acid or sulfuric acid.
The described mould material of step 3) is poly (ether sulfone) film, polysulfone membrane, polyvinylidene fluoride film, polyacrylonitrile or polyamide membrane; The microfiltration membrane aperture is 0.2-0.45 μ m, and the ultra-filtration membrane molecular weight cut-off is 1000-3000KD, and the nanofiltration membrane molecular weight cut-off is 200-400KD.
A kind of in the optional ethyl acetate-acetone of the described recrystallization solvent of step 5), acetone, chloroform-acetone, the chloroform-methanol.
Technical characterstic:
A. a whole set of method is not high to environment and equipment requirements, and extraction time is short, the purity height.
B. adopt membrane separation technique in this separation purge process, improved product purity, and the sample before the macroporous adsorbent resin column chromatography is purified, alleviate, prolonged the work-ing life of resin the resin infringement; Sample can directly be gone up sample before nanofiltration made the resin column chromatography, had simplified operation.
C. the present invention adopts macroporous resin enrichment, and adsorptive capacity is big, uses repeatedly after can handling, and is easy to control.
D. adopt crystallization and recrystallization to carry out purifying, the purification efficiency height.
Embodiment:
Embodiment 1:
Get the mugwort powder 10kg that withers, the aqueous sodium hydroxide solution 80L that adds pH10 is 45 ℃ of following supersound extraction 30 minutes, uses the aqueous sodium hydroxide solution 40L supersound extraction 1 time of pH10 after the filtration again, merges filtered liquid twice.Transfer pH to neutral with hydrochloric acid filtered liquid, under the 3000r/min rotating speed centrifugal 15 minutes, throw out adds an amount of distilled water and makes the 1L suspension liquid, in suspension liquid, add the 1L chloroform and carry out the continuous ultrasound extraction, extract 2 times, take off layer, upper strata liquid is again with 1L ethyl acetate continuous ultrasound extraction 2 times, merge four extraction liquids and be total to 4L, in the multifunctional membrane separating device, carry out micro-filtration successively, ultrafiltration and nanofiltration, working pressure is 2bar, wherein the microfiltration membrane material is a polyvinylidene fluoride film, the aperture is 0.2 μ m, the ultra-filtration membrane material is a polyacrylonitrile film, molecular weight cut-off is 2000KD, nanofiltration membrane is a poly (ether sulfone) film, and molecular weight cut-off is 200KD, will pass through the LSA-10 macroporous adsorbent resin through the stoste of nanofiltration, be washed till earlier closely colourless with deionized water, discard water lotion, use the aqueous ethanolic solution gradient elution again, with the volume ratio of ethanol in aqueous ethanolic solution, by 30% ethanol, interval 10% is incremented to 90% successively, collects elutriant, with the elutriant decompression recycling ethanol, concentrate, the dry chrysoeriol ethanol elution thing that gets, with 50% methyl alcohol heating for dissolving, cooling, standing over night, separate out yellow crystal, filter, get the chrysoeriol crude product, use ethyl acetate-acetone recrystallization again, get the pure product of 146mg chrysoeriol, chrysoeriol purity is 98.6%.
Embodiment 2:
Get tree peony powder of seeds 10kg, the aqueous sodium hydroxide solution 100L that adds pH9 is 50 ℃ of following supersound extraction 1 hour, uses the aqueous sodium hydroxide solution 50L supersound extraction 1 time of pH9 after the filtration again, merges filtered liquid twice.Transfer pH to neutral with hydrochloric acid filtered liquid, under the 3000r/min rotating speed centrifugal 10 minutes, throw out adds an amount of distilled water and makes the 1L suspension liquid, in suspension liquid, add the 1L chloroform and carry out the continuous ultrasound extraction, extract 2 times, take off layer, upper strata liquid is again with 1L ethyl acetate continuous ultrasound extraction 2 times, merge four extraction liquids and be total to 4L, in the multifunctional membrane separating device, carry out micro-filtration successively, ultrafiltration and nanofiltration, working pressure is 1.5bar, wherein the microfiltration membrane material is a polyvinylidene fluoride film, the aperture is 0.45 μ m, the ultra-filtration membrane material is a poly (ether sulfone) film, molecular weight cut-off is 3000KD, nanofiltration membrane is a polysulfone membrane, and molecular weight cut-off is 300KD, will pass through the D101 macroporous adsorbent resin through the stoste of nanofiltration, be washed till earlier closely colourless with deionized water, discard water lotion, use the aqueous ethanolic solution gradient elution again, with the volume ratio of ethanol in aqueous ethanolic solution, by 30% ethanol, interval 10% is incremented to 90% successively, collects elutriant, with the elutriant decompression recycling ethanol, concentrate, the dry chrysoeriol ethanol elution thing that gets, with 50% methyl alcohol heating for dissolving, cooling, standing over night, separate out yellow crystal, filter, get the chrysoeriol crude product, use chloroform-acetone recrystallization again, get the pure product of 137.5mg chrysoeriol, chrysoeriol purity is 98.4%.
Embodiment 3:
Get Evergreen Dogwood herb powder 50kg, the aqueous sodium hydroxide solution 600L that adds pH10 is 60 ℃ of following supersound extraction 1.5 hours, uses the aqueous sodium hydroxide solution 300L supersound extraction 1 time of pH10 after the filtration again, merges filtered liquid twice.Transfer pH to neutral with hydrochloric acid filtered liquid, under the 3000r/min rotating speed centrifugal 10 minutes, throw out adds an amount of distilled water and makes the 5L suspension liquid, in suspension liquid, add the 5L chloroform and carry out the continuous ultrasound extraction, extract 2 times, take off layer, upper strata liquid is again with 5L ethyl acetate continuous ultrasound extraction 2 times, merge four extraction liquids and be total to 20L, in the multifunctional membrane separating device, carry out micro-filtration successively, ultrafiltration and nanofiltration, working pressure is 1.5bar, wherein the microfiltration membrane material is a polyvinylidene fluoride film, the aperture is 0.45 μ m, the ultra-filtration membrane material is a poly (ether sulfone) film, molecular weight cut-off is 3000KD, nanofiltration membrane is a polysulfone membrane, and molecular weight cut-off is 300KD, will pass through the AB-8 macroporous adsorbent resin through the stoste of nanofiltration, be washed till earlier closely colourless with deionized water, discard water lotion, use the aqueous ethanolic solution gradient elution again, with the volume ratio of ethanol in aqueous ethanolic solution, by 30% ethanol, interval 10% is incremented to 90% successively, collects elutriant, with the elutriant decompression recycling ethanol, concentrate, the dry chrysoeriol ethanol elution thing that gets, with 50% methyl alcohol heating for dissolving, cooling, standing over night, separate out yellow crystal, filter, get the chrysoeriol crude product, use acetone recrystallization again, get the pure product of 239mg chrysoeriol, chrysoeriol purity is 96.56%.
Embodiment 4:
Get celery seed powder 100kg, the aqueous sodium hydroxide solution 1300L that adds pH9 is 55 ℃ of following supersound extraction 2 hours, uses the aqueous sodium hydroxide solution 600L supersound extraction 1 time of pH9 after the filtration again, merges filtered liquid twice.Transfer pH to neutral with hydrochloric acid filtered liquid, under the 3000r/min rotating speed centrifugal 15 minutes, throw out adds an amount of distilled water and makes the 10L suspension liquid, in suspension liquid, add the 10L chloroform and carry out the continuous ultrasound extraction, extract 2 times, take off layer, upper strata liquid is again with 10L ethyl acetate continuous ultrasound extraction 2 times, merge four extraction liquids and be total to 40L, in the multifunctional membrane separating device, carry out micro-filtration successively, ultrafiltration and nanofiltration, working pressure is 1.2bar, wherein the microfiltration membrane material is a polyvinylidene fluoride film, the aperture is 0.2 μ m, the ultra-filtration membrane material is a polysulfone membrane, molecular weight cut-off is 1000KD, nanofiltration membrane is a poly (ether sulfone) film, and molecular weight cut-off is 200KD, will pass through the XSD-1 macroporous adsorbent resin through the stoste of nanofiltration, be washed till earlier closely colourless with deionized water, discard water lotion, use the aqueous ethanolic solution gradient elution again, with the volume ratio of ethanol in aqueous ethanolic solution, by 30% ethanol, interval 10% is incremented to 90% successively, collects elutriant, with the elutriant decompression recycling ethanol, concentrate, the dry chrysoeriol ethanol elution thing that gets, with 50% methyl alcohol heating for dissolving, cooling, standing over night, separate out yellow crystal, filter, get the chrysoeriol crude product, use the chloroform-methanol recrystallization again, get the pure product of 489mg chrysoeriol, chrysoeriol purity is 97.22%.
Claims (6)
1. the preparation method of a chrysoeriol is characterized in that may further comprise the steps:
1) get the medicinal material that contains chrysoeriol, pulverize, use buck supersound extraction 0.5-3 hour, filter, concentrate, to neutral, centrifugal with acid accent pH, the precipitation adding distil water is made suspension liquid;
2) add ethyl acetate extraction again, combining extraction liquid after suspension liquid being added chloroform extraction;
3) above-mentioned extraction liquid is carried out micro-filtration, ultrafiltration and nanofiltration successively in the multifunctional membrane separating device;
4) above-mentioned stoste through nanofiltration is passed through macroporous resin, elder generation is washed till closely colourless with deionized water, discard water lotion, use the aqueous ethanolic solution gradient elution again, with the volume ratio of ethanol in aqueous ethanolic solution, by 30% ethanol, interval 10% is incremented to 90% successively, collects elutriant;
5) with above-mentioned elutriant decompression recycling ethanol, concentrate, drying is with 50% methyl alcohol heating for dissolving, cooling, standing over night are separated out crystallization, filter, get the chrysoeriol crude product, use ethyl acetate, methyl alcohol, acetone, chloroform or their mixing solutions recrystallization again, get the pure product of chrysoeriol.
2. the preparation method of a kind of chrysoeriol according to claim 1, it is characterized in that: the described medicinal material that contains chrysoeriol of step 1) is the mugwort that withers, Lonicera confusa DC., Evergreen Dogwood, tree peony seed, Herba Vernoniae Cinereae, celery seed, lotus leaf, etc.
3. the preparation method of a kind of chrysoeriol according to claim 1 is characterized in that: the optional ammoniacal liquor of the described buck of step 1), sodium hydroxide solution, pH is 9-12, consumption be quality of medicinal material 4-15 doubly, extract 40-60 ℃ of temperature.
4. the preparation method of a kind of chrysoeriol according to claim 1, it is characterized in that: the used acid of step 1) is hydrochloric acid, acetic acid, phosphoric acid or sulfuric acid.
5. the preparation method of a kind of chrysoeriol according to claim 1, it is characterized in that: the described mould material of step 3) is poly (ether sulfone) film, polysulfone membrane, polyvinylidene fluoride film, polyacrylonitrile or polyamide membrane; The microfiltration membrane aperture is 0.2-0.45 μ m, and the ultra-filtration membrane molecular weight cut-off is 1000-3000KD, and the nanofiltration membrane molecular weight cut-off is 200-400KD.
6. the preparation method of a kind of chrysoeriol according to claim 1 is characterized in that: a kind of in the optional ethyl acetate-acetone of the described recrystallization solvent of step 5), acetone, chloroform-acetone, the chloroform-methanol.
Priority Applications (1)
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|---|---|---|---|
| CN2010102358997A CN101973974A (en) | 2010-07-26 | 2010-07-26 | Preparation method of chrysoeriol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102358997A CN101973974A (en) | 2010-07-26 | 2010-07-26 | Preparation method of chrysoeriol |
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| CN101973974A true CN101973974A (en) | 2011-02-16 |
Family
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| CN2010102358997A Pending CN101973974A (en) | 2010-07-26 | 2010-07-26 | Preparation method of chrysoeriol |
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-
2010
- 2010-07-26 CN CN2010102358997A patent/CN101973974A/en active Pending
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Application publication date: 20110216 |