CN108640955A - A method of extraction prepares crenatoside from bend pipe broomrape - Google Patents
A method of extraction prepares crenatoside from bend pipe broomrape Download PDFInfo
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- CN108640955A CN108640955A CN201810385307.6A CN201810385307A CN108640955A CN 108640955 A CN108640955 A CN 108640955A CN 201810385307 A CN201810385307 A CN 201810385307A CN 108640955 A CN108640955 A CN 108640955A
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- crenatoside
- bend pipe
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
The present invention relates to the method for preparing crenatoside is extracted in a kind of broomrape from bend pipe, belong to Chemistry for Chinese Traditional Medicine field, processing step includes as follows：Bend pipe broomrape raw material crushes, and 95% EtOH Sonicate is added to extract, and extracting solution is concentrated to give medicinal extract, then by ethyl acetate water two-phase dispersion extraction, takes ethyl acetate organic phase to concentrate, isolated and purified through silica gel medium pressure column chromatography, obtain high-purity crenatoside.The method of the present invention has many advantages, such as that simple for process, efficiently quick, purity is high, preparation amount is big.
Description
Technical field：
The invention belongs to Chemistry for Chinese Traditional Medicine fields, are related to the extraction and preparation technique of crenatoside, in mainly a kind of application
The method that pressure column chromatography method prepares high-purity crenatoside from bend pipe broomrape crude extract.
Background technology：
Crenatoside, alias：Oraposide；Orobanchoside, chemical name：β-D-glucopyranose,3-
O-(6-deoxy-α-L-mannopyranosyl)-1,2-O-[(2S)-2-(3,4-dihydroxyphenyl)-1,2-
Ethanediyl] -, 4- [(2E) -3- (3,4-dihydroxyphenyl) -2-propenoate], molecular formula：C29H34O15, point
Son amount：622.57, compositional classification：Benzyl carbinol glycoside, structural formula are as follows：
Physical property：Light yellow crystal (methanol), UV365Aobvious blue-fluorescence down, the reaction of 1% ferric trichloride ethanol solution are in
It is black-and-blue, there is good water-soluble and hygroscopicity, be soluble in methanol, dissolve in acetone.Pharmacological properties：With significantly anti-oxidant
Activity is only second to vitamin C, while pharmacological evaluation shows it also and has the effects that reducing blood lipid, hypoglycemic, anti-inflammatory, sterilization.
Currently without the report for the systems approach for preparing high-purity crenatoside.It is therefore desirable to seek it is a kind of it is easy,
The method of safety, economic, efficient extracting and developing and purifying crenatoside, to promote the deep development to bend pipe broomrape
And utilization.
Invention content：
It is a kind of simple for process that present invention aims at exploitations, efficiently, quickly, purifying and preparing high-purity crenatoside's
Method.
The technical proposal of the invention is realized in this way：
A method of extraction prepares crenatoside from bend pipe broomrape, includes the following steps：
1) ultrasonic extraction：By bend pipe broomrape pulverizing medicinal materials, ethyl alcohol is used to carry out ultrasonic extraction, rotary evaporation as extraction solvent
It is concentrated to give medicinal extract；
2) it extracts：By above-mentioned medicinal extract by ethyl acetate-water two-phase dispersion extraction, ethyl acetate layer is taken, second is recovered under reduced pressure
Acetoacetic ester, residue extraction concentrate；
3) silica gel medium pressure chromatographs：Above-mentioned gained extraction concentrate is isolated and purified through silica gel medium pressure column chromatography, according to
TLC inspections, which are known, merges target fraction, obtains crenatoside eluents；
4) it recrystallizes：It being dissolved with solvent after said components are concentrated under reduced pressure, opening, which is stood, is precipitated crenatoside crystallizations,
Filtering；It repeats this step 2-4 times, dries in the shade to get crenatoside.
Preferably, crushed in the step 1) is 80-100 mesh；Ultrasonic time is 40-60min, ultrasonic extraction 3-5 every time
Merge extracting solution after secondary.
Preferably, ethanol consumption is 8-10 times of bend pipe broomrape powder product in the step 1), concentration of alcohol 95%.
Preferably, the volume ratio of ethyl acetate and water is 1 in the step 2):1；Ethyl acetate is arranged with bend pipe in step 1)
When powder volume ratio is 2:1.
Preferably, silica gel medium pressure column chromatography chromatogram solvent system is dichloromethane in the step 3):Methanol:Water volume ratio
For (18-12):1:0.1；Permanent gradient elution is collected by every part of 50mL, and (polyamide board, Haiyang Chemical Plant, Qingdao's production are known in TLC inspections
Product；Solvent, dichloromethane：Methanol：Water (10:3:0.1)；Color developing agent, 1% ferric trichloride ethanol solution), take Rf value (Rf)
=0.4 single-point fraction merges, and obtains crenatoside eluents.
Preferably, the elution flow rate that the step 3) isolates and purifies is 10-20mL/min, and column pressure is 2.5MPa.
Preferably, step 4) the crystallisation step solvent is methanol.
Preferably, step 4) the crystallisation step solvent methanol dosage is step 1) per 1000mL bend pipe broomrape medicinal powders
It is 40-50 DEG C that (being equivalent to medicinal powder quality 260g), which uses methanol 5-20mL, solution temperature,.
Advantageous effect：
The present invention provides a kind of simple for process, efficiently, quickly, the method for purifying and preparing high-purity crenatoside, compared with
Conventional method, the crenatoside purity highers that this method is extracted, and this method are more efficiently quick, and preparation amount is big.
Specific implementation mode：
It is further illustrated the present invention below in conjunction with specific implementation mode, but the scope of protection of present invention is not limited to
In following embodiments.
Embodiment 1：
It is 80 mesh by bend pipe broomrape pulverizing medicinal materials, takes powder 1000mL (being equivalent to medicinal powder quality 260g), is added 8 times
95% EtOH Sonicate of volume extracts 5 times, each 40min, and filtering merges extracting solution, is concentrated under reduced pressure to give bronzing medicinal extract,
With ethyl acetate and water each 2000mL (volume ratios 1:1) two-phase extracts, and takes upper layer ethyl acetate organic phase, is concentrated under reduced pressure into leaching
Cream obtains extraction concentrate.Above-mentioned gained is extracted concentrate through six-way valve to be pumped into pretreated silica gel medium pressure column (pressure is
In 2.5MPa), dichloromethane is used:Methanol：Water (volume ratio 18:1:0.1) permanent gradient elution, elution flow rate 20mL/min are pressed
Every part of 50mL is collected, and (polyamide board, Haiyang Chemical Plant, Qingdao's product are known in TLC inspections；Solvent, dichloromethane：Methanol：Water (10:
3:0.1)；Color developing agent, 1% ferric trichloride ethanol solution), take the single-point fraction of Rf value (Rf)=0.4 to merge, by above-mentioned merging
Fraction is heated with 15mL methanol at 40 DEG C after being concentrated under reduced pressure, and opening is stood, and crenatoside crystallizations are precipitated, filter out
Crenatoside crystallize, repeat crystallization 2 times, dry in the shade to get purity be 98.25% crenatoside.
Embodiment 2：
It is 100 mesh by bend pipe broomrape pulverizing medicinal materials, takes powder 1000mL (being equivalent to medicinal powder quality 260g), is added 9
95% EtOH Sonicate of times volume extracts 4 times, each 50min, and filtering merges extracting solution, is concentrated under reduced pressure to give bronzing leaching
Above-mentioned gained extraction concentrate is pumped into through six-way valve in pretreated silica gel medium pressure column (pressure 2.5MPa), with two by cream
Chloromethanes:Methanol：Water (volume ratio 18:1:0.1) permanent gradient elution, elution flow rate 20mL/min are collected by every part of 50mL,
(polyamide board, Haiyang Chemical Plant, Qingdao's product are known in TLC inspections；Solvent, dichloromethane：Methanol：Water (10:3:0.1)；Color developing agent,
1% ferric trichloride ethanol solution), it takes the single-point fraction of Rf value (Rf)=0.4 to merge, it is concentrated under reduced pressure in above-mentioned merging fraction
The methanol of 10mL is used to be heated at 45 DEG C afterwards, opening is stood, and crenatoside crystallizations are precipitated, and filters out crenatoside crystallizations,
Repeat crystallization 2 times, dry in the shade to get purity be 98.31% crenatoside.
Embodiment 3：
It is 90 mesh by bend pipe broomrape pulverizing medicinal materials, takes powder 1000mL (being equivalent to medicinal powder quality 260g), is added 10
95% EtOH Sonicate of times volume extracts 3 times, each 60min, and filtering merges extracting solution, is concentrated under reduced pressure to give bronzing leaching
Above-mentioned gained extraction concentrate is pumped into through six-way valve in pretreated silica gel medium pressure column (pressure 2.5MPa), with two by cream
Chloromethanes:Methanol：Water (volume ratio 18:1:0.1) permanent gradient elution, elution flow rate 20mL/min are collected by every part of 50mL,
(polyamide board, Haiyang Chemical Plant, Qingdao's product are known in TLC inspections；Solvent, dichloromethane：Methanol：Water (10:3:0.1)；Color developing agent,
1% ferric trichloride ethanol solution), it takes the single-point fraction of Rf value (Rf)=0.4 to merge, it is concentrated under reduced pressure in above-mentioned merging fraction
The methanol of 10mL is used to be heated at 50 DEG C afterwards, opening is stood, and crenatoside crystallizations are precipitated, and filters out crenatoside crystallizations,
Repeat crystallization 3 times, dry in the shade to get purity be 98.57% crenatoside.
Embodiment 4：
It is 80 mesh by bend pipe broomrape pulverizing medicinal materials, takes powder 1000mL (being equivalent to medicinal powder quality 260g), is added 10
95% EtOH Sonicate of times volume extracts 5 times, each 60min, and filtering merges extracting solution, is concentrated under reduced pressure to give bronzing leaching
Above-mentioned gained extraction concentrate is pumped into through six-way valve in pretreated silica gel medium pressure column (pressure 2.5MPa), with two by cream
Chloromethanes:Methanol：Water (volume ratio 18:1:0.1) permanent gradient elution, elution flow rate 20mL/min are collected by every part of 50mL,
(polyamide board, Haiyang Chemical Plant, Qingdao's product are known in TLC inspections；Solvent, dichloromethane：Methanol：Water (10:3:0.1)；Color developing agent,
1% ferric trichloride ethanol solution), it takes the single-point fraction of Rf value (Rf)=0.4 to merge, it is concentrated under reduced pressure in above-mentioned merging fraction
The methanol of 15mL is used to be heated at 50 DEG C afterwards, opening is stood, and crenatoside crystallizations are precipitated, and filters out crenatoside crystallizations,
Repeat crystallization 4 times, dry in the shade to get purity be 98.22% crenatoside.
Claims (8)
1. extracting the method for preparing crenatoside in a kind of broomrape from bend pipe, it is characterised in that：Include the following steps：
1) ultrasonic extraction：By bend pipe broomrape pulverizing medicinal materials, ethyl alcohol is used to carry out ultrasonic extraction, rotary evaporation concentration as extraction solvent
Obtain medicinal extract；
2) it extracts：By above-mentioned medicinal extract by ethyl acetate-water two-phase dispersion extraction, ethyl acetate layer is taken, acetic acid second is recovered under reduced pressure
Ester, residue extraction concentrate；
3) silica gel medium pressure chromatographs：Above-mentioned gained extraction concentrate is isolated and purified through silica gel medium pressure column chromatography, is examined according to TLC
Know and merge target fraction, obtains crenatoside eluents；
4) it recrystallizes：It is dissolved with solvent after said components are concentrated under reduced pressure, opening, which is stood, is precipitated crenatoside crystallizations, filtering；
It repeats this step 2-4 times, dries in the shade to get crenatoside.
2. the method as described in claim 1, it is characterised in that：Crushed in the step 1) is 80-100 mesh；Ultrasonic time is every
Secondary is 40-60min, 3-5 rear merging extracting solution of ultrasonic extraction.
3. the method as described in claim 1, it is characterised in that：Ethanol consumption is bend pipe broomrape powder product in the step 1)
8-10 times, concentration of alcohol 95%.
4. the method as described in claim 1, it is characterised in that：The volume ratio of ethyl acetate and water is 1 in the step 2):1；
Ethyl acetate is 2 with bend pipe broomrape powder volume ratio in step 1):1.
5. the method as described in claim 1, it is characterised in that：Silica gel medium pressure column chromatography chromatogram solvent system in the step 3)
For dichloromethane:Methanol:Water volume ratio is (18-12):1:0.1；Permanent gradient elution takes the single-point stream of Rf value (Rf)=0.4
Part merges, and obtains crenatoside eluents.
6. the method as described in claim 1, it is characterised in that：The elution flow rate that the step 3) isolates and purifies is 10-20mL/
Min, column pressure are 2.5MPa.
7. the method as described in claim 1, it is characterised in that：Step 4) the crystallisation step solvent is methanol.
8. the method for claim 7, it is characterised in that：Step 4) the crystallisation step solvent methanol dosage is step 1)
Per 1000mL bend pipe broomrape medicinal powder methanol 5-20mL, solution temperature is 40-50 DEG C.
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| CN201810385307.6A CN108640955A (en) | 2018-04-26 | 2018-04-26 | A method of extraction prepares crenatoside from bend pipe broomrape |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101214282A (en) * | 2007-12-28 | 2008-07-09 | 中山大学 | Method for extracting active component from cistanche salsa |
| CN101411753A (en) * | 2008-12-04 | 2009-04-22 | 闫明 | Broomrape extract, broomrape total glycosides, broomrape polysaccharide as well as preparation method and application thereof |
-
2018
- 2018-04-26 CN CN201810385307.6A patent/CN108640955A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101214282A (en) * | 2007-12-28 | 2008-07-09 | 中山大学 | Method for extracting active component from cistanche salsa |
| CN101411753A (en) * | 2008-12-04 | 2009-04-22 | 闫明 | Broomrape extract, broomrape total glycosides, broomrape polysaccharide as well as preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| 曲正义，等: "ＲP-HPLC同时测定向日葵列当中苯乙醇苷类化合物crenatoside和类叶升麻苷", 《中国实验方剂学杂志》 * |
| 曲正义，等: "向日葵列当抗氧化活性研究", 《中药材》 * |
| 曲正义: "向日葵列当化学成分及抗氧化活性研究", 《中国农业科学院硕士学位论文》 * |
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Application publication date: 20181012 |