CN107383041A - A kind of method that podophyllotoxin and Hyperoside are extracted from Dysosma versipellis - Google Patents
A kind of method that podophyllotoxin and Hyperoside are extracted from Dysosma versipellis Download PDFInfo
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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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- C07H1/08—Separation; Purification from natural products
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- 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
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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Abstract
The present invention provides a kind of method that podophyllotoxin and Hyperoside are extracted from Dysosma versipellis, and Dysosma versipellis is extracted using alcohol reflux, filtering, filtrate concentration, obtains medicinal extract；Medicinal extract adds diethyl ether extraction, the upper silicagel column purifying of extract concentration, crystallization, adds alcohol to dissolve rear decoloring, recrystallizes to obtain podophyllotoxin sterling；Lower floor's liquid adds alcohol to dissolve, filtering, silicagel column on filtrate, alcohol eluen concentration, crystallizes to obtain Hyperoside sterling.The method can be extracted to obtain podophyllotoxin and the Hyperoside of high-purity simultaneously, substantially increase the utilization rate of Dysosma versipellis, improve added value；Podophyllotoxin and the production cost of Hyperoside are reduced simultaneously, saves Dysosma versipellis medicine resource, while shortens extraction time, greatlys save energy consumption again.
Description
Art
The present invention relates to a kind of method that high-purity podophyllotoxin and Hyperoside are extracted from Dysosma versipellis, belong to natural production
The technical field of thing chemistry.
Background technology
Dysosma versipellis, it is called：Jin Kuilian, drought are anistree, belong to Berberidaceae may apple, Latin literary fame Dysosma
versipellis(Hance)M.Cheng ex Ying.The height above sea level 300-2200m dark and damp place of hillside sylvan life is distributed in, is among the people
Conventional Chinese herbal medicine, wind eliminating the phlegm can be dissipated by being used as medicine, and sterilization solution is swollen, desinsection, there is its special detoxicating functions, can control snake bite.Root and
Rhizome podophyllotoxin containing anticancer component and Deoxypodophyllotoxin, in addition glycosides containing astragalus, Hyperoside, Quercetin, Kaempferol and paddy
The compositions such as sterol.
Podophyllotoxin belongs to lignanoids, is primarily present in Berberidaceae foot leaf careless category, Jeffersonia, Diphylleia and anise
In nelumbium.Remarkable result is obtained for treating condyloma acuminatum, has certain inhibitory action to inhibition of HIV, herpesviral.Podophyllum emodi var chinense
Toxin white, needle-shaped crystals powder.Chloroform, acetone, ethyl acetate and benzene are soluble in, dissolves in ethanol, ether is not soluble in water.Point
Minor C22H22O8, molecular weight 414.41,183.3~184.0 DEG C of fusing point.Podophyllotoxin extraction and purification process is methanol, second at present
Podophyllotoxin in the plant such as the backflow of the organic solvents such as alcohol or Ultrasonic Heating extraction Dysosma versipellis, Dysosma Pleiantha, Chinese podophyllum root, obtains podophyllotoxin
Plain medicinal extract, then using solvent extraction, recrystallizing technology separates to obtain podophyllotoxin.
A kind of method that podophyllotoxin is extracted from Dysosma versipellis of Publication No. CN102875563A Introduction To Cn Patent,
Extract is obtained using microwave abstracting, is added on large pore resin absorption column and adsorbs, elutes, ethanol is recovered under reduced pressure and concentrates, is added to
On polyamide chromatography post, elution, by the use of class polyamide film of the same race more than state eluant, eluent to deploy as supporting detection, collect, subtract
Recycling design is pressed, acetone crystallization is added, fractional crystallization, washs, is drying to obtain.
Publication No. CN101974008A Introduction To Cn Patent one kind extraction purification podophyllotoxin from small Dysosma versipellis
Technique.The technique is to take small Dysosma versipellis rhizome to be ground into coarse powder, and small Dysosma versipellis coarse powder is pre-processed by organic solvent,
Through refluxing extraction in hot water, filter residue continues circumfluence distillation and filtered again, merges filtrate twice, is used in right amount after reclaiming organic solvent
Water constant volume, obtain podophyllotoxin extract solution.It is 0.12g/mL~0.18g/mL's to be prepared with podophyllotoxin extract solution containing crude drug amount
Solution is as sample solution, and the macroporous absorbent resin for selecting to have purified is as upper prop resin, fully after absorption, respectively with water, 10%
Ethanol washes away impurity successively, then is eluted with strippant, collects elution fraction, uses suitable quantity of water constant volume after reclaiming strippant, obtains
To podophyllotoxin refined solution.
Publication No. CN1587266 Introduction To Cn Patent is a kind of from a kind of extraction and purification process of podophyllotoxin.This
Invention is using solvent crystallization and depressurizes chromatography extraction purification podophyllotoxin, simple to operate, is easy to industrialized production, Ke Yifang
Just the podophyllotoxin that purity is not less than 97% is obtained.It can directly be extracted from Chinese podophyllum root, or enter one by Chinese podophyllum root extract
One-step refining forms.
Publication No. CN101503410 Introduction To Cn Patent is a kind of to prepare high-purity podophyllotoxin from Chinese podophyllum root
Method, be divided into raw material with alcohols extract medicinal extract again through extracting to obtain podophyllotoxin crude product and podophyllotoxin crude product high pressure column chromatography two
Part forms, and concretely comprises the following steps：By Chinese podophyllum root rhizome after ultramicro grinding, alcohols solvent heating extraction is used under Ultrasonic Conditions
Three times, merge extract solution three times, merge extract solution concentration alcohols solvent, obtain the bronzing medicinal extract that proportion is 1.0-1.2；Again plus
The water for entering 1-2 times of medicinal extract volume obtains podophyllotoxin alcohol aqueous phase；Podophyllotoxin alcohol aqueous phase is extracted with isometric dichloromethane
Three times, merge dichloromethane phase three times, be concentrated to give the faint yellow podophyllotoxin crude product that purity is 40%-50%；It is faint yellow
Podophyllotoxin crude product dissolves, and loading to silica gel is the high-pressure column of 300-400 mesh, is washed with the mixing of acetone+dichloromethane solvent
De- liquid elutes, collection product section eluent, and after thickening filtration, drying to purity is more than 99% podophyllotoxin fine work.
A kind of method that podophyllotoxin is extracted from unmrellaleaf of Publication No. CN101974006A Introduction To Cn Patent,
Method is using unmrellaleaf as raw material, and 75-85% methanol ultrasonic extractions, be concentrated under reduced pressure to obtain medicinal extract, then with ethyl acetate ultrasonic extraction,
Extract solution is concentrated, and places crystallization, and crystallization is dissolved with absolute ethyl alcohol, adds activated carbon backflow to decolourize, filtering, and organic solvent extraction is dense
Contracting, crystallization, absolute methanol recrystallization are drying to obtain product.Present invention process is simple to operate, cost is low.
Hyperoside, also known as Quercetin -3-O- β-D- galactopyranosides, belong to flavonols glycosides compound.It is faint yellow
Acicular crystal, 227~229 DEG C of fusing point, is soluble in ethanol, methanol, acetone and pyridine.Hyperoside has liver protection, antiallergy, resisted
Inflammation, spasmolysis, decompression, anti-hepatitis virus and notable cough-relieving etc. act on, and particularly have analgesia and the defencive function to cardiovascular and cerebrovascular,
Its analgesic activity is better than aspirin, is weaker than morphine, and does not have dependence, is referred to as " the 3rd class antalgesic ", is a kind of new
Type antalgesic.At present mainly using alcohol heat reflux extraction, the extraction of methanol circumfluence distillation, EtOH Sonicate, methanol ultrasonic extraction
The methods of Hyperoside is slightly carried from crude drug powder.
The preparation side of Hyperoside and hypericin in Publication No. CN1880328 Introduction To Cn Patent hypericum perforatum
Method, the leaf that passes through for being related to the preparation method present invention comprehensive utilization China's abundant of Hyperoside and hypericin medicinal active ingredient connect
Fruit is stuck up, while prepares two kinds of medicinal active ingredients of the high Hyperoside of total recovery rate and product purity and hypericin,
Production cost is low；In process of production, the recovery of multi-solvents such as ethanol ether and Reusability again are realized；Realize anti-
Micelle abstraction agent and the regeneration of polymeric adsorbent and Reusability use the plant biological active material that the inventive method is prepared, can
It is widely used in the medicine such as clearing heat and detoxicating astringing to arrest bleeding diuresis and depressed treatment.
Publication No. CN1634325 Introduction To Cn Patent one kind from the Rhododendron pizewalskii leaf extraction separation Hyperoside and
The method of gossypetin -3-O- β-D- galactosides, after Rhododendron pizewalskii leaf is crushed, heat backflow first is carried out with petroleum ether to remove
Pigment and oil-soluble impurities；Extracted again with ethanol solution, filter, obtain crude extract；After crude extract is dissolved with water, through polyamide
Column chromatography for separation, ethanol solution elution, and efflux is collected respectively, concentrate, absolute ethyl alcohol crystallization, 95% ethyl alcohol recrystallization, obtain
To gossypetin -3-O- β-D- galactosides (yield is 0.1%~0.3%) and Hyperoside (yield is 0.3%~
0.6%).
Publication No. CN101260133 Introduction To Cn Patent prepares Hyperoside and isoquercitin from cotton petal
Method, be using cotton petal as raw material, extracted with organic solvent, extract solution is then concentrated under reduced pressure into medicinal extract, add appropriate
Aqueous dissolution, upper macroreticular resin are the column chromatography of carrier, rinse post bed to colourless with water, then elute post with ethanol solution
Bed, eluent is collected, concentration, obtains the crude product of Hyperoside and isoquercitin, then crude product is obtained with silica gel or C18 silica gel column chromatographies
To Hyperoside and the sterling of isoquercitin.
A kind of Publication No. CN101386634 Introduction To Cn Patent extracting method and its preparation and use of Hyperoside
On the way, it is by the concentrate of sunset abelmoschus flower ethanol extract, with n-butanol or ethyl acetate extraction, or passes through HPD100 or HPD600
Macroporous adsorbent resin column chromatography and maniod ebish flower extract crude product is made, then through solvent purification and complex crystallization, obtain Hyperoside and contain
Amount is 90-98% by weight percentage.Hyperoside preparation, it is processed into by active component and pharmaceutic adjuvant of Hyperoside
Freeze drying powder injection or liquid drugs injection or transfusion or dripping pill or tablet or capsule or soft capsule.
A kind of method for separating Hyperoside of Publication No. CN102234299A Introduction To Cn Patent, it is characterized in that take
Large-fruited Chinese hawthorn or leaves of Hawthorn medicinal material, are ground into coarse powder, with aqueous alcohol refluxing extraction, extract solution filtering, merging filtrate, are concentrated under reduced pressure into
Without alcohol taste, cleaned through AB-8 or D101 macroporous absorbent resins, using concentration as 30-80% ethanol elutions, be concentrated under reduced pressure into no alcohol taste,
Dry, gained dried object is separated through polyamide column chromatography, and with hydrous ethanol gradient elution, elution fraction is concentrated under reduced pressure, warp
Layer of silica gel column chromatography, then with ethyl acetate-butanone-formic acid-water elution or ethyl acetate-acetone-formic acid-water elution, directly obtain
Hyperoside.
The extraction separation of a kind of Hyperoside bulk drug of Publication No. CN103224540A Introduction To Cn Patent and quiet
The preparation method of arteries and veins parenteral solution, by rhododendron micranthum leaf ethanol heating and refluxing extraction, ethanol is recovered under reduced pressure in alcohol extract, is condensed into leaching
Cream；Above-mentioned medicinal extract is extracted 2-3 times with ethyl acetate again, each dosage is 8-12 times of medicinal extract, and each extraction time is that 1-2 is small
When, ethyl acetate is reclaimed, obtains ethyl acetate extract；Silica gel column chromatography is carried out, is recrystallized, obtains Hyperoside sterling, is made
Into intravenous fluid.
The producer of Hyperoside is extracted in a kind of wintergreen of Publication No. CN103030674A Introduction To Cn Patent
Method, raw material is put into after coarse crushing from cast hopper, the rotation of extractor group main frame, material slowly pushed away backward from unit front end
Enter, while the feed tube of Extraction solvent slave group end enters in extractor, the material forward end stream by tank rear end through movement
Dynamic, solid-liquid two-phase material fully contacts in this reverse movement, so as to which extracts active ingredients in medicinal material be come out.The dregs of a decoction are through going out
Material conveyer is forced to be pushed to slag notch and discharge, and special Juice squeezer is extruded the dregs of a decoction, and dregs of a decoction Shen residual liquor is squeezed
Go out medicinal material tissue, reduce dregs of a decoction Shen residual liquor content.Extraction efficiency is higher, extraction is more complete.
A kind of Publication No. CN102600194A Introduction To Cn Patent extracting method of Hyperoside and its prepare medicine
The purposes of thing, take acute turpinia leaf or Herba Hyperici Monogyni, add 5~15 times amount 30%~90% alcohol refluxs extract 1~3 time, often
Secondary refluxing extraction 1~3 hour, filtration；Merging filtrate, ethanol is reclaimed, the aqueous solution is eluted by large pore resin absorption column, and collection is washed
De- part, is concentrated under reduced pressure, and dries, and obtains the total glycosides of mixing of Hyperoside, through silica gel column chromatography, Sephadex LH-20 column chromatographies point
From merging Hyperoside fraction, crystallization obtains Hyperoside sterling, and Hyperoside can make neuraminidase inhibitor and be used in advance
Anti- and treatment influenza, is made pharmaceutically acceptable formulation.
Publication No. CN102924537A Introduction To Cn Patent one kind prepares Hyperoside simultaneously from Folium Apocyni Veneti
With the method for isoquercitrin, using Folium Apocyni Veneti as raw material, heated backflow or ultrasonic extraction, be concentrated under reduced pressure to obtain medicinal extract；Medicinal extract adds
Water is dissolved, and depigmentaton and oil-soluble impurities are removed with petroleum ether；Aqueous phase dilutes, and passes through the macroporous absorbent resin of at least thtee-stage shiplock
Post, after Dynamic Adsorption to saturation, stream plus wash miscellaneous liquid and wash miscellaneous, then flowed out with elution to without Hyperoside and isoquercitrin,
And collect efflux；Efflux is concentrated under reduced pressure, and recrystallizes in methyl alcohol, through being filled with C18The middle pressure gradient elution system of reverse phase silica gel
System obtains Hyperoside and isoquercitrin that purity reaches 90%-98% simultaneously.
In summary, podophyllotoxin and Hyperoside are respectively provided with stronger pharmacological action, before the application of medicine
Scape is wide.Dysosma versipellis does not obtain comprehensive development and utilization at present, explores from Dysosma versipellis while extracts podophyllotoxin and Hyperoside
Mean a great.
The content of the invention
Presently disclosed documents and materials only study the extraction active ingredient podophyllotoxin from Dysosma versipellis, but not to other activity
Composition is comprehensively utilized.For the non-comprehensive development and utilization problem of active component of Dysosma versipellis, the present invention provides a kind of operation letter
List, rational technology, the quick production technology for extracting podophyllotoxin and Hyperoside simultaneously.
The technical solution adopted by the present invention includes：Dysosma versipellis is extracted using alcohol reflux, filtering, filtrate concentration, obtains medicinal extract；
Medicinal extract adds diethyl ether extraction, the upper silicagel column purifying of extract concentration, crystallization, adds alcohol to dissolve rear decoloring, recrystallize podophyllotoxin is pure
Product；Lower floor's liquid adds alcohol to dissolve, filtering, silicagel column on filtrate, alcohol eluen concentration, crystallizes to obtain Hyperoside sterling.
Therefore, the present invention provides a kind of method that podophyllotoxin and Hyperoside are extracted from Dysosma versipellis, specific steps bag
Include as follows：
(1) Dysosma versipellis is crushed to the mesh of 80 mesh~120, adds 70~90% ethanol solution refluxing extraction 2 times, 2 hours every time,
Filtering, merging filtrate, filtrate are concentrated under reduced pressure at 55 DEG C~65 DEG C, obtain medicinal extract.
(2) by medicinal extract add two volumes ether extract 2 times, 1 hour every time, merge ether extraction liquid, obtain ether solution and
Lower floor's liquid.
(3) ether solution is concentrated into certain volume, upper silica gel column chromatography (200~300 mesh), after adsorbing 30min, uses 5-
The ethanol of 8BV upper prop liquid elutes with dichloromethane mixed liquor, collects eluent I, is concentrated into the 1/5~1/15 of original volume, room
Lower place to crystallization of temperature separates out, and filters to obtain coarse crystallization.
(4) coarse crystallization adds 80-90% ethanol to dissolve, and adds proper amount of active carbon to decolourize, and stands 1 hour, filtering, is concentrated into crystallization
Separate out, let cool crystallization, obtain podophyllotoxin sterling.
(5) the 80-90% ethanol solutions of lower floor's liquid in step (2) are dissolved, filtering, silicagel column on filtrate (200~
300 mesh), 20min is adsorbed, first carries out washing post with the water of 1-3BV column volumes, discards water elution, then with 5-8BV column volumes
80-90% ethanol solutions are eluted, and obtain eluent II；
(6) eluent II is concentrated under reduced pressure into the 1/5~1/10 of original volume at 50 DEG C~60 DEG C, crystallized, filtering, obtained golden
Silk peach glycosides.
Described to be filtered into ceramic membrane filter 1 time, fenestra pore size is 0.22 μm；BV refers to column volume.
70-90% ethanol solutions are added described in the step (1), are 10-15 by volume L/ Dysosma versipellis weight kg ratios:1.
1/5~1/8 that certain volume is original volume is concentrated into described in the step (3)；Ethanol and dichloro in eluent
The volume ratio of methane is 1-3:10.
The amount of 80-90% ethanol solutions is added described in the step (4), is 10- by volume L/ coarse crystallization weight kg ratios
15:1；The amount of activated carbon kg/ filtrate volumes L ratios by weight are 0.01-0.05:1；
The amount of 80-90% ethanol solutions is added described in the step (5), is 1- by volume L/ lower floors liquid volume L ratios
2:1。
Ethanol solution refers to the mixed liquor of ethanol and water in the step, and 90% ethanol solution refers to that 90mL ethanol adds
10ml water is mixed).
Technique effect
1st, extracted simultaneously by using Dysosma versipellis and obtain podophyllotoxin and the Hyperoside of high-purity, substantially increase anise
The utilization rate of lotus, improves added value；Podophyllotoxin and the production cost of Hyperoside are reduced simultaneously, saves Dysosma versipellis medicine
Use resource.
2nd, raw material of the present invention is extracted using alcohol reflux, while obtains podophyllotoxin and Hyperoside alcohol extract, is improved again
Recovery rate, while extraction time is shortened, energy consumption is greatlyd save again.
3rd, the method that the present invention is combined using silica gel column chromatography with crystalline phase, it is more simple to operate than macroporous absorbent resin, repeat
Property is good.
Embodiment
With reference to specific embodiment, the invention will be further described, following examples be intended to illustrate invention rather than
Limitation of the invention further.
Embodiment 1
Dysosma versipellis is crushed, 100 mesh sieves is crossed, weighs 5kg, adds 50L 70% ethanol solution refluxing extraction 2 times, 2 is small every time
When, ceramic membrane filter, merging filtrate, filtrate is concentrated under reduced pressure at 55 DEG C, obtains medicinal extract 10L；Medicinal extract plus 20L ether are extracted 2 times,
1 hour every time, merge ether extraction liquid, obtain ether solution and lower floor's liquid.Ether solution is concentrated into 8L, upper silica gel column chromatography (200
~300 mesh), after adsorbing 30min, with 40L ethanol-dichloromethane (2:10) mixed liquor elutes, and collects eluent I, is concentrated into
4L, place to crystallization separate out at room temperature, ceramic membrane filter obtains coarse crystallization 180g.Coarse crystallization adds 2L 90% ethanol to dissolve, and adds 40g
Activated carbon decolorizing, stand 1 hour, filtering, be concentrated into crystallization separate out, let cool crystallization, obtain podophyllotoxin sterling 150g.By lower floor
Liquid 10L 90% ethanol solution dissolves, ceramic membrane filter, silicagel column (200~300 mesh) on filtrate, adsorbs 20min, first
Carry out washing post with 40L water, discard water elution, then eluted with 100L 80% ethanol solution, obtain eluent II；Will
Eluent II is concentrated under reduced pressure into 10L at 50 DEG C, crystallization, obtains Hyperoside 12.5g.Detected by HPLC methods, the purity of podophyllotoxin
For 98.85%, the purity of Hyperoside is 99.21%.
Embodiment 2
Dysosma versipellis is crushed, 120 mesh sieves is crossed, weighs 10kg, adds 120L 80% ethanol solution refluxing extraction 2 times, 2 is small every time
When, ceramic membrane filter, merging filtrate, filtrate is concentrated under reduced pressure at 65 DEG C, obtains medicinal extract 30L；Medicinal extract plus 60L ether are extracted 2 times,
1 hour every time, merge ether extraction liquid, obtain ether solution and lower floor's liquid.Ether solution is concentrated into 20L, upper silica gel column chromatography
(200~300 mesh), after adsorbing 30min, with 120L ethanol-dichloromethane (3:10) mixed liquor elutes, and collects eluent I, dense
12L is reduced to, places to crystallization separate out at room temperature, ceramic membrane filter obtains coarse crystallization 400g.Coarse crystallization adds 5L 80% ethanol to dissolve,
Add 100g activated carbon decolorizing, stand 1 hour, filtering, be concentrated into crystallization and separate out, let cool crystallization, obtain podophyllotoxin sterling 320g.
Lower floor's liquid 30L 80% ethanol solution is dissolved, ceramic membrane filter, silicagel column (200~300 mesh) on filtrate, absorption
20min, first carry out washing post with 80L water, discard water elution, then eluted with 300L 80% ethanol solution, washed
De- liquid II；Eluent II is concentrated under reduced pressure into 30L at 50 DEG C, crystallizes, obtains Hyperoside 27.2g.Detected by HPLC methods, podophyllotoxin
The purity of element is 99.06%, and the purity of Hyperoside is 98.82%.
Embodiment 3
Dysosma versipellis is crushed, 80 mesh sieves is crossed, weighs 15kg, adds 200L 90% ethanol solution refluxing extraction 2 times, 2 is small every time
When, ceramic membrane filter, merging filtrate, filtrate is concentrated under reduced pressure at 60 DEG C, obtains medicinal extract 40L；Medicinal extract plus 80L ether are extracted 2 times,
1 hour every time, merge ether extraction liquid, obtain ether solution and lower floor's liquid.Ether solution is concentrated into 25L, upper silica gel column chromatography
(200~300 mesh), after adsorbing 30min, with 150L ethanol-dichloromethane (1:10) mixed liquor elutes, and collects eluent I, dense
10L is reduced to, places to crystallization separate out at room temperature, ceramic membrane filter obtains coarse crystallization 520g.Coarse crystallization adds 6L 90% ethanol to dissolve,
Add 150g activated carbon decolorizing, stand 1 hour, filtering, be concentrated into crystallization and separate out, let cool crystallization, obtain podophyllotoxin sterling 432g.
Lower floor's liquid 60L 90% ethanol solution is dissolved, ceramic membrane filter, silicagel column (200~300 mesh) on filtrate, absorption
20min, first carry out washing post with 150L water, discard water elution, then eluted with 400L 80% ethanol solution, washed
De- liquid II；Eluent II is concentrated under reduced pressure into 40L at 50 DEG C, crystallizes, obtains Hyperoside 42.6g.Detected by HPLC methods, podophyllotoxin
The purity of element is 99.47%, and the purity of Hyperoside is 98.63%.
Claims (5)
1. the present invention provides a kind of method that podophyllotoxin and Hyperoside are extracted from Dysosma versipellis, specific steps include as follows：
(1) Dysosma versipellis is crushed to the mesh of 80 mesh~120, adds 70~90% ethanol solution refluxing extraction 2 times, 2 hours every time, mistake
Filter, merging filtrate, filtrate are concentrated under reduced pressure at 55 DEG C~65 DEG C, obtain medicinal extract.
(2) add the ether of two volumes to extract 2 times medicinal extract, 1 hour every time, merge ether extraction liquid, obtain ether solution and lower floor
Liquid.
(3) ether solution is concentrated into certain volume, upper silica gel column chromatography (200~300 mesh), after adsorbing 30min, with 5-8BV
The ethanol of post liquid elutes with dichloromethane mixed liquor, collects eluent I, is concentrated into the 1/5~1/15 of original volume, room temperature decentralization
Put to crystallization and separate out, filter to obtain coarse crystallization.
(4) coarse crystallization adds 80-90% ethanol to dissolve, and adds proper amount of active carbon to decolourize, and stands 1 hour, filtering, is concentrated into crystallization analysis
Go out, let cool crystallization, obtain podophyllotoxin sterling.
(5) the 80-90% ethanol solutions of lower floor's liquid in step (2) are dissolved, filtering, silicagel column (200~300 on filtrate
Mesh), 20min is adsorbed, first carries out washing post with the water of 1-3BV column volumes, discards water elution, then the 80- with 5-8BV column volumes
90% ethanol solution is eluted, and obtains eluent II；
(6) eluent II is concentrated under reduced pressure into the 1/5~1/10 of original volume at 50 DEG C~60 DEG C, crystallized, filtering, obtain Hypericum Chinense
Glycosides.
2. the method for claim 1 wherein 70-90% ethanol solutions are added described in step (1), by volume L/ Dysosma versipellis weight
Kg ratios are 10-15:1.
3. the method for claim 1 wherein certain volume is concentrated into described in step (3) as the 1/5~1/8 of original volume；Elution
The volume ratio of ethanol and dichloromethane is 1-3 in liquid:10.
4. the method for claim 1 wherein the amount that 80-90% ethanol solutions are added described in step (4), by volume L/ coarse crystallization
Weight kg ratios are 10-15:1；The amount of activated carbon kg/ filtrate volumes L ratios by weight are 0.01-0.05:1.
5. the method for claim 1 wherein the amount that 80-90% ethanol solutions are added described in step (5), by volume L/ subnatants
Body volume L ratios are 1-2:1.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101974006A (en) * | 2010-10-19 | 2011-02-16 | 南京泽朗医药科技有限公司 | Method for extracting podophyllotoxin from umbrella leaf |
| CN101974008A (en) * | 2010-10-28 | 2011-02-16 | 中南大学 | Process for extracting and purifying podophyllotoxin from Dysosma difformis |
| CN102133255A (en) * | 2011-03-08 | 2011-07-27 | 暨南大学 | Antineoplastic podophyllum traditional Chinese medicine extract and preparation method and application thereof |
| CN102875563A (en) * | 2012-09-24 | 2013-01-16 | 南京正亮医药科技有限公司 | Method for extracting podophyllotoxin from dysosma versipellis |
-
2017
- 2017-07-17 CN CN201710581277.1A patent/CN107383041A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101974006A (en) * | 2010-10-19 | 2011-02-16 | 南京泽朗医药科技有限公司 | Method for extracting podophyllotoxin from umbrella leaf |
| CN101974008A (en) * | 2010-10-28 | 2011-02-16 | 中南大学 | Process for extracting and purifying podophyllotoxin from Dysosma difformis |
| CN102133255A (en) * | 2011-03-08 | 2011-07-27 | 暨南大学 | Antineoplastic podophyllum traditional Chinese medicine extract and preparation method and application thereof |
| CN102875563A (en) * | 2012-09-24 | 2013-01-16 | 南京正亮医药科技有限公司 | Method for extracting podophyllotoxin from dysosma versipellis |
Non-Patent Citations (7)
| Title |
|---|
| 姜飞等: "八角莲的化学成分研究", 《中草药》 * |
| 曾步兵等主编: "《药用天然产物全合成：合成路线精选》", 31 March 2016, 华东理工大学出版社 * |
| 李强等主编: "《新编常用中药有效成分手册》", 31 January 2008, 中国协和医科大学出版社 * |
| 王生新等: "大坂山杜鹃化学成分的研究 II.(+)-儿茶酸、金丝桃苷及毒性成分的分离鉴定", 《植物学报》 * |
| 王竹鑫等主编: "《袖珍中药安全速查手册》", 31 March 2008, 湖南科学技术出版社 * |
| 罗永明主编: "《中药化学成分提取分离技术与方法》", 31 January 2016, 上海科学技术出版社 * |
| 钟静芬主编: "《表面活性剂在药学中的应用》", 29 February 1996, 人民卫生出版社 * |
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