CN104557828B - Method and the application thereof separating 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is extracted from Radix Ligulariae Dentatae - Google Patents
Method and the application thereof separating 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is extracted from Radix Ligulariae Dentatae Download PDFInfo
- Publication number
- CN104557828B CN104557828B CN201510036344.2A CN201510036344A CN104557828B CN 104557828 B CN104557828 B CN 104557828B CN 201510036344 A CN201510036344 A CN 201510036344A CN 104557828 B CN104557828 B CN 104557828B
- Authority
- CN
- China
- Prior art keywords
- alkene
- dihydroxy
- airy
- fen
- lactone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses method and the application thereof extracting not fragrant 7 (11) alkene 12,8 lactones of separation 6,8 dihydroxy Airy from Radix Ligulariae Dentatae, belong to natural product chemistry technical field.The present invention discloses 6, the extracting method of not fragrant 7 (11) alkene 12,8 lactones of 8 dihydroxy Airies, including: 1) take Radix Ligulariae Dentatae medicinal material coarse powder, extract with 95% ethanol merceration, obtain ethanol extraction；2) by ethanol extraction first with petroleum ether (60 90 DEG C) surname extraction defat, then carry out surname extraction, recycling design with dichloromethane, prepare dichloromethane extract；3) dichloromethane extract is separated by silica gel column chromatography, collect the eluent of petroleum ether (60 90 DEG C) ethyl acetate (6: 1), stand, precipitate to brown color, white irregular prism-shaped crystallization is obtained after Jing Zhi, it is not fragrant 7 (11) alkene 12,8 lactones of 6,8 dihydroxy Airies through Structural Identification.The invention also discloses 6, the antiinflammatory action of not fragrant 7 (11) alkene 12,8 lactones of 8 dihydroxy Airies, thus can apply to prepare anti-inflammatory drug.
Description
Technical field
The invention belongs to natural product chemistry technical field, be specifically related to from Radix Ligulariae Dentatae extract separation 6,8-bis-
The method of hydroxyl-Airy Mo Fen-7 (11)-alkene-12,8-lactone and application thereof.
Background technology
Anti-inflammatory drug is the second largest class medicine being only second to anti-infectives, some active ingredient of Chinese herbs such as glycoside,
Alkaloids, flavonoid, terpenoid, volatile oil etc. all have good antiinflammatory action, and natural resources of Chinese medicinal materials is rich
Richness, pharmacological action is extensive, has antiinflammatory action, and the pharmacology such as immunomodulating, heat-clearing and toxic substances removing, activating blood circulation to dissipate blood stasis is made
With, current people increasingly pay attention to the research of anti-inflammatory drug in natural drug.
Radix Ligulariae Dentatae, also known as ligularia fischeri, rescue greatly, Folium Nelumbinis seven, mountain Radix Asteris, for feverfew renal lobe Farfugium kaemferi
Ligularia fischeri (Ledeb.) Turcz. herbaceos perennial, medicinal part is its root being dried and root
Stem.Radix Ligulariae Dentatae, warm in nature, sweet in the mouth is pungent.There is vital energy regualting and blood circulation-promoting, pain relieving, the function of eliminating phlegm and stopping cough.Main use
In diseases such as treatment traumatic injury, impairment caused by overstrain, lumbago and skelalgia, cough and asthmas.It is distributed in northeast, the Inner Mongol, mountain
The ground such as west, Shaanxi, Gansu and Sichuan.
Research report in recent years find in Radix Ligulariae Dentatae containing phenols, sesquiterpenoids, esters, organic acid,
The compound such as glycoside and volatile oil, and its ethanol extraction have analgesia and antiinflammatory action.Result of study is also
Display sesquiterpenoids has anticancer, antiinflammatory, anti-neurotoxicity, antiviral and blood fat reducing isoreactivity.
6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone belongs to sesquiterpenoids, has been reported that at present from greatly
This compound of isolated in my platymiscium of we in Huang Wu, wood, but have no and obtain from Radix Ligulariae Dentatae
The research report of this compound, also has no about 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12, and 8-lactone has
There is the research report of anti-inflammatory activity.
Summary of the invention
It is an object of the invention to provide one extraction separation 6,8-dihydroxy-Airy from Radix Ligulariae Dentatae the most fragrant
-7 (11)-alkene-12, the method for 8-lactone and application thereof, extraction conditions is gentle, easy and simple to handle, extraction ratio is high and becomes
This is low, and the compound anti-inflammatory activity prepared is high, thus contributes to playing a role during inflammation treatment.
The present invention is to be achieved through the following technical solutions:
Separation 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12, the method for 8-lactone, bag is extracted from Radix Ligulariae Dentatae
Include following steps:
1) take root and the rhizome coarse powder of Radix Ligulariae Dentatae, extract for several times with the ethanol merceration that volume fraction is 95%,
United extraction liquid, recycling design, prepare sepia ethanol extraction；
2) being mixed thoroughly by ethanol extraction kieselguhr, first is that extractant carries out rope with petroleum ether (60-90 DEG C)
Family name extracts, and discards extracting solution；Carry out surname extraction with dichloromethane for extractant again, reclaim dichloromethane molten
Agent, prepares dichloromethane extract；
3) by silica gel chromatographic column on dichloromethane extract, molten by petroleum ether (60-90 DEG C) ethyl acetate
Agent system carries out gradient elution, isolated 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone crude product.
Also include that the dihydroxy of the 6,8-to isolated-Airy Mo Fen-7 (11)-alkene-12,8-lactone crude product carries out weight
Crystallization treatment, prepared 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12, the irregular prism-shaped of white of 8-lactone
Crystallization.
It is by 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone crude product stone that described recrystallization processes
The mixed solvent recrystallization repeatedly of oil ether (60-90 DEG C) ethyl acetate (2: 1) processes.
Step 1) described in merceration extract specifically with the alcohol steep that volume fraction is 95% three times, three times
Add the volume (L) of ethanol and be respectively the root of Radix Ligulariae Dentatae and 6,4 and 4 times of rhizome meal quality (kg).
Step 3) described in petroleum ether (60-90 DEG C) ethyl acetate solvent system be by petroleum ether
(60-90 DEG C): ethyl acetate volume ratio be 20: 1～3: 1 ratio carry out gradient elution, to eluting
Liquid carries out inspection to be known, and collects the eluent of petroleum ether (60-90 DEG C) ethyl acetate (6: 1).
The eluent of petroleum ether (60-90 DEG C) ethyl acetate (6: 1) collected is carried out concentrating under reduced pressure,
Recycling design, carries out inspection by thin layer chromatography and knows, merge stream part that composition is essentially identical, stand to precipitating analysis
Go out, precipitation is filtered, obtains brown color 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone crude product.
6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12, the application in preparing anti-inflammatory drug of the 8-lactone, described
The structure such as following formula of 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone:
Compared with prior art, the present invention has a following useful technique effect:
The inventive method produce from Mount Taibai, Shaanxi first isolated 6,8-dihydroxy Radix Ligulariae Dentatae root and rhizome-
Airy Mo Fen-7 (11)-alkene-12,8-lactone.The inventive method use volume fraction be 95% ethanol be that solvent enters
Row extracts, and toxicity is little, reusable edible, low cost, is suitable for industrialized production；And use the mode of merceration
Extracting, device is simple, and extraction conditions is gentle, it is not necessary to heating, dissolution impurity is few；Carrying out Soxhlet
During extraction, it is first that solvent carries out defat with petroleum ether (60-90 DEG C), removes strong lipophilic contaminant, then use
Dichloromethane extraction, obtains dichloromethane extract；Use the mode of surname extraction, save solvent, operation
Easier, extraction efficiency is high；Then by dichloromethane extract loading silica gel chromatographic column, enter with solvent system
Row gradient elution, collects the eluent of petroleum ether (60-90 DEG C) ethyl acetate (6: 1), separates out palm fibre
Yellow mercury oxide, precipitation, through recrystallization repeatedly, is accredited as 6, and 8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12, in 8-
Ester.
The present invention is the most fragrant to 6,8-dihydroxy-Airy prepared in Radix Ligulariae Dentatae with antiinflammatory action for pharmacodynamic index
-7 (11)-alkene-12,8-lactone carries out activity research, by dimethylbenzene induced mice auricle edema inhibition test and angle
Fork dish glue induced mice foot swelling Inhibition test, it was demonstrated that in Radix Ligulariae Dentatae 6,8-dihydroxy-Airy Mo Fen-7 (11)-
Alkene-12,8-lactone has the effect of preferable antiinflammatory.Result shows: 6,8-dihydroxy-Airy Mo Fen-7 (11)-
Alkene-12,8-lactone anti-inflammatory activity is notable, is expected to become the drug candidate with antiinflammatory action；Also it is calabash simultaneously
The quality control of reed seven medical material, clinical rational drug use and further exploitation provide foundation.The present invention is first
Disclosing in Radix Ligulariae Dentatae 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone has antiinflammatory action, determines
It has the active component of antiinflammatory action for Radix Ligulariae Dentatae, such that it is able to be applied to prepare anti-inflammatory drug.
Accompanying drawing explanation
Fig. 1 is 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone TLC figure that the present invention prepares；
Fig. 2 is the ESI-MS of 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone that the present invention prepares
Figure；
The X-ray monocrystalline of 6,8-dihydroxy prepared by Fig. 3 present invention-Airy Mo Fen-7 (11)-alkene-12,8-lactone
Diffraction pattern.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described in further detail, described in the present invention
Explain rather than limit.
The invention discloses to extract from Radix Ligulariae Dentatae and separate in 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-
The method of ester, comprises the following steps:
1) merceration extracts: take root and the rhizome coarse powder of Radix Ligulariae Dentatae, is that 95% ethanol is cold by volume fraction respectively
Extraction peek time, filters, discards medicinal residues, united extraction liquid, recycling design, obtain sepia ethanol extraction.
2) dichloromethane surname extraction: after gained ethanol extraction and kieselguhr being mixed thoroughly, first use petroleum ether
(60-90 DEG C) surname extraction defat, removes strong lipophilic moieties, then carries out surname extraction with dichloromethane,
Recycling design obtains dichloromethane extract；
3) by dichloromethane extract through pillar layer separation, 6 are obtained, 8-dihydroxy-Airy Mo Fen-7 (11)-alkene
-12,8-lactone.
Described pillar layer separation step is as follows: takes after dichloromethane extract mixes sample and adds to silica gel chromatographic column
On, carry out gradient elution by petroleum ether (60-90 DEG C) ethyl acetate solvent system (20: 1～3: 1),
Collecting the eluent of wherein petroleum ether (60-90 DEG C) ethyl acetate (6: 1), recycling design, with thin
Layer chromatography inspection is known, and merges stream part that composition is essentially identical, places, has brown color crystallization, filters,
Obtain brown color precipitation.
4) column chromatography being divided isolated precipitation through re-crystallization step, obtains 6,8-dihydroxy-Airy is not
The crystallization of fragrant-7 (11)-alkene-12,8-lactones.Subtractive process, is that column chromatography is divided isolated precipitation oil
Ether (60-90 DEG C) ethyl acetate (2: 1) mixed solvent recrystallization repeatedly, obtains 6,8-dihydroxy-Chinese mugwort
The white irregular prism-shaped crystallization of Li Mofen-7 (11)-alkene-12,8-lactone.
Described Radix Ligulariae Dentatae is Qinling-Bashan mountainous area genuine medicinal materials, originates in Mount Taibai, Shaanxi.
In sum, the present invention proposes that a kind of extraction conditions is gentle, simple to operate, extraction ratio is high and cost
Low method, the method produces effective extraction 6,8-dihydroxy Radix Ligulariae Dentatae root and rhizome first from Mount Taibai, Shaanxi
-Airy Mo Fen-7 (11)-alkene-12,8-lactone.
Embodiment 1
The preparation of 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone
Take root and rhizome coarse powder 4kg that Radix Ligulariae Dentatae is dried, be that 95% ethanol merceration extracts three times by volume fraction,
The volume (L) that three times add is respectively the root of Radix Ligulariae Dentatae and 6,4 and 4 times of rhizome meal quality (kg),
Merceration three days, stirs three times, each 10 minutes every day every time.Filter, discard medicinal residues, united extraction liquid,
Recycling design, obtains sepia ethanol extraction 433.0g.
After gained ethanol extraction and kieselguhr are mixed thoroughly, first take off with petroleum ether (60-90 DEG C) surname extraction
Fat, removes strong lipophilic moieties, then gradation dichloromethane carries out surname extraction 18h as solvent, reclaims
Dichloromethane solvent, obtains dichloromethane extract, altogether 160.6g.
Take dichloromethane extract 55.0g, carry out pillar layer separation on a silica gel column, with petroleum ether (60-90 DEG C)
Ethyl acetate solvent system is as eluant, and 20: 1～3: 1 carry out gradient elution, at stone by volume
Oil ether (60-90 DEG C) and ethyl acetate volume ratio are respectively 20: 1,10: 1,6: 1 and 3: 1 conditions
Under, collecting stream part, every 250mL collects a stream part, collects 253 stream parts, concentrated and thin layer altogether
Chromatography inspection is known, and merges stream part that composition is essentially identical, places, has brown color crystallization, filters,
Brown color precipitates.
Column chromatography is separated and separates out precipitation by petroleum ether (60-90 DEG C) ethyl acetate (2: 1) repeatedly
Recrystallization, obtains the crystallization of white irregular prism-shaped, referred to as compound A, altogether 446.5mg (0.0326%).
The purity test of compound A uses TLC method, sees Fig. 1；Select petroleum ether (60-90 DEG C) the most respectively
Ethyl acetate (3: 2), 2. petroleum ether (60-90 DEG C) ethyl acetate hexane (2: 2: 3),
3. ethyl acetate methylene chloride (3: 1) and 4. ethyl acetate hexane (3: 2) be developing solvent, exhibition
Opening, take out, dry, spray, with 10% ethanol solution of sulfuric acid, after volatilizing solvent, is heated to speckle at 105 DEG C
Colour developing is clear, it is seen that in single punctation under light；Put inspection under uviol lamp (365nm) to know, aobvious single red
Color fluorescence speckle, it was demonstrated that compound A is single compound.
Compound A is carried out structural characterization, and analysis result is as follows:
Compound A be white irregular prism-shaped crystallization (petroleum ether (60-90 DEG C) ethyl acetate (2:
1)), fusing point: 208～210 DEG C.Molecular weight: 266.UVNm:218.9.IRcm-1:
3502 (-OH), 3442 (-OH), 2966,2933,1722 (-C=O), 1695 (-C=C), 1008
(C-O-C).ESI-MS m/z:248 [M-18]+, 140 [-C7H8O3]+, 124 [-C9H6]+, 109 [-C8H13]+,
95,81,67,55 [-C4H7]+；Through consulting reference literature, the crystal formation of discovery compound A, fusing point,
It is basically identical that UV, IR, MS data and document [1,2,3] are reported, therefore speculates that compound A is 6,8-
Dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone, then confirm to be defined as 6,8-through X-ray single facet spy instrument
Dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone, its structure is:
[1]Moriyama Y,Takahashi T.New sesquiterpene lactones of eremophilane-type
from Ligularia Fauriei(Fr.)Koidz[J].Bull Chem Soc Jpn,1976,49:3196-3199.
[2] Tan Aimin, Hong Xin. the chemical constitution study [J] of net arteries and veins Farfugium kaemferi. China Medicine University's journal, 2002,
33(2):104-106.
[3]Naya K,Kanazawa R,Sawada M.The photosensitized oxygenation of
furanoeremophilanes.I.The isomeric hydroperoxides from petasalbin and their
transformations to lactones[J].Bulletin of the Chemical Society of Japan,1975,
48(11):3220-3225.
The anti-inflammatory activity of prepared 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is verified:
1. the impact of xylol induced mice auricle edema
Choose body weight 18-22g Kunming mouse, male and female half and half, adaptability raise 1 day (ad lib and
Drinking-water) after, be randomly divided into 5 groups, often group 10, give respectively model group (5% Tween 80 solution),
Aspirin group (200mg/kg), 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is low, medium and high
Dosage group (2mg/kg, 4mg/kg and 8mg/kg), continuous gastric infusion 5d, 1 time/d, after last is administered
1h, is applied to mouse right ear exterior feature two sides 0.05mL by dimethylbenzene, and left ear is not coated with, and is taken off by mice cervical vertebra after 40min
Mortar is put to death, and cuts mice ears wide, takes off left and right ear with the card punch of diameter 8mm at the two same positions of ear
Sheet, weighs, and using left and right auricle weight difference as auricle swelling degree, is used for representing medicine anti-inflammatory effect, calculates
Suppression ratio, suppression ratio %=(administration group swelling-model control group swelling)/model control group swelling
×100.Experimental result is shown in Table 1:
The impact of the mice auricle swelling caused by table 16,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone xylol (N=10)
Note: each medication group mice auricle swelling degree compares with model control group,*P < 0.05,**P<0.01；
As can be seen from Table 1, sample low, medium and high dosage group (2mg/kg, 4mg/kg and 8mg/kg)
Compared with the auricle swelling degree of blank model group, all there is significant difference (P ＜ 0.01), Mice Auricle is swollen
Swollen significantly inhibit effect；And sample is to the suppression degree of mice auricle swelling and dosage positive correlation；Sample is high
The suppression ratio of dosage group (8mg/kg) is 67.10%, less than positive control aspirin group (200mg/kg)
Suppression ratio (73.81%), and the dosage of sample high dose group is well below aspirin group.This is real
Testing result to show, in Radix Ligulariae Dentatae 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone has the most anti-
Scorching effect.
2. the impact of Carrageenan induced mice foot swelling
Choose body weight 18-22g Kunming mouse, male and female half and half, adaptability raise 1 day (ad lib and
Drinking-water) after, be randomly divided into 5 groups, often group 10, give respectively model group (5% Tween 80 solution),
Aspirin group (200mg/kg), 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is low, medium and high
Dosage group (2mg/kg, 4mg/kg and 8mg/kg), 1 time/d of gastric infusion, continuous 4d, the 5th day in
Mice right metapedes lift hemostasis 1.0% carrageenin 50 μ L, causes acute toes swelling model, causes inflammation
After give relative medicine again 1 time, put to death mice next day, the double metapedes of clip, accurate weighing, with right sufficient matter
Amount deducts left sufficient quality and is foot sole of the foot inflammatory swelling degree, calculates mice pedal swelling suppression ratio, suppression ratio %=
(administration group swelling-model control group swelling)/model control group swelling × 100.Experimental result is shown in
Table 2.
The impact of the mice pedal swelling caused by table 26,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone Carrageenan (N=10)
Note: each medication group mice swelling degree of the paw compares with model control group,*P < 0.05,**P<0.01；
As can be seen from Table 2, sample low, medium and high dosage group (2mg/kg, 4mg/kg and 8mg/kg)
Compared with the swelling degree of the paw of blank model group, all there is significant difference (P ＜ 0.01), the mice foot sole of the foot is swollen
Swollen significantly inhibit effect；And sample is to the suppression degree of mice pedal swelling and dosage positive correlation；Sample is high
The suppression ratio of dosage group (8mg/kg) is 56.36%, less than positive control aspirin group (200mg/kg)
Suppression ratio (62.74%), and the dosage of sample high dose group is well below aspirin group.This is real
Testing result to show, in Radix Ligulariae Dentatae 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone has the most anti-
Scorching effect.
In sum, the present invention proposes that a kind of extraction conditions is gentle, simple to operate, the method for low cost,
It is the most fragrant that the method produces effectively extraction 6,8-dihydroxy-Airy Radix Ligulariae Dentatae root and rhizome first from Mount Taibai, Shaanxi
-7 (11)-alkene-12,8-lactones；And 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone, there is antiinflammatory
Effect, is expected to become the drug candidate with antiinflammatory action；Also be simultaneously Radix Ligulariae Dentatae medical material quality control,
Clinical rational drug use and further exploitation provide foundation.
Claims (4)
1. extraction separation 6 from Radix Ligulariae Dentatae, 8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12, the method for 8-lactone,
It is characterized in that, comprise the following steps:
1) take root and the rhizome coarse powder of Radix Ligulariae Dentatae, extract for several times with the ethanol merceration that volume fraction is 95%,
United extraction liquid, recycling design, prepare sepia ethanol extraction；
Described merceration extracts specifically with the alcohol steep that volume fraction is 95% three times, adds ethanol three times
Volume be respectively the root of Radix Ligulariae Dentatae and the 6 of rhizome meal quality, 4,4 times；Wherein, the volume list of ethanol
Position is L, and the mass unit of root and rhizome coarse powder is kg；
2) ethanol extraction kieselguhr is mixed thoroughly, first carry out surname extraction with petroleum ether for extractant, then
Carry out surname extraction, then recycling design with dichloromethane for extractant, prepare dichloromethane extract；
3) by silica gel chromatographic column on dichloromethane extract, ladder is carried out with petroleum ether-ethyl acetate solvent system
Degree eluting, isolated 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone crude product；
6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone crude product of isolated is carried out at recrystallization
Reason, prepares 6, and 8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12, the irregular prism-shaped of white of 8-lactone crystallizes；
It is by 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone crude product petroleum ether that recrystallization processes: acetic acid
Ethyl ester volume ratio is the mixed solvent recrystallization repeatedly process of 2: 1.
Extract from Radix Ligulariae Dentatae the most according to claim 1 separate 6,8-dihydroxy-Airy Mo Fen-7 (11)-
Alkene-12, the method for 8-lactone, it is characterised in that step 3) described in petroleum ether-ethyl acetate solvent system
In petroleum ether: ethyl acetate volume ratio be 20: 1～3: 1 ratio carry out gradient elution, to eluent
Carry out inspection to know, collect petroleum ether: ethyl acetate volume ratio is the eluent of 6: 1.
Extract from Radix Ligulariae Dentatae the most according to claim 2 separate 6,8-dihydroxy-Airy Mo Fen-7 (11)-
Alkene-12, the method for 8-lactone, it is characterised in that the petroleum ether that will collect: ethyl acetate volume ratio is 6: 1
Eluent carry out concentrating under reduced pressure, recycling design, carry out inspection by thin layer chromatography and know, merge eluent, quiet
Put to Precipitation, precipitation is filtered, obtains brown color 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-
Lactone crude product.
4. 6,8-dihydroxy-Airy Mo Fen-7 (11) that in claims 1 to 3, method described in any one prepares-
Alkene-12, the application in preparing anti-inflammatory drug of the 8-lactone, described 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene
The structure of-12,8-lactone such as following formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510036344.2A CN104557828B (en) | 2015-01-23 | 2015-01-23 | Method and the application thereof separating 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is extracted from Radix Ligulariae Dentatae |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510036344.2A CN104557828B (en) | 2015-01-23 | 2015-01-23 | Method and the application thereof separating 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is extracted from Radix Ligulariae Dentatae |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104557828A CN104557828A (en) | 2015-04-29 |
| CN104557828B true CN104557828B (en) | 2016-08-24 |
Family
ID=53075001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510036344.2A Expired - Fee Related CN104557828B (en) | 2015-01-23 | 2015-01-23 | Method and the application thereof separating 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is extracted from Radix Ligulariae Dentatae |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104557828B (en) |
-
2015
- 2015-01-23 CN CN201510036344.2A patent/CN104557828B/en not_active Expired - Fee Related
Non-Patent Citations (6)
| Title |
|---|
| Eremophilenolides from Ligularia fischeri;Wen-Shu Wang et al.;《Planta Med.》;20001231;第66卷;第189-191页 * |
| New Eremophilane Sesquiterpenes from the Roots of Ligularia fischeri;Meicai Deng et al.;《Helvetica Chimica Acta》;20091231;第92卷;第495-501页 * |
| Terpenoids from the Roots of Ligularia muliensis;Qiu-Hong Wu et al.;《Helvetica Chimica Acta》;20061231;第89卷;第915-922页 * |
| Two New Eremophilenolides from Ligularia fischeri;Wen Shu Wang et al.;《Chinese Chemical Letters》;19991231;第10卷(第7期);第571-572页 * |
| 五味子藤化学成分研究;叶丹丹等;《新乡医学院学报》;20130531;第30卷(第5期);第329-331、336页 * |
| 蹄叶橐吾乙醇提取物抗炎作用的实验研究;李丽波等;《中国中医药科技》;20040930;第11卷(第5期);第285-287页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104557828A (en) | 2015-04-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Azietaku et al. | A review of the ethnopharmacology, phytochemistry and pharmacology of Notopterygium incisum | |
| Orhan et al. | Appraisal of anti-inflammatory potential of the clubmoss, Lycopodium clavatum L. | |
| Mandal et al. | Antidiarrhoeal activity of carbazole alkaloids from Murraya koenigii Spreng (Rutaceae) seeds | |
| EP3461545A1 (en) | Flash distillation in a vacuum for enrichment of natural substances | |
| CN104825463A (en) | Metabolic-regulation and anti-hypoxia application of ganoderma leucocontextum extract | |
| CN104606184B (en) | The inflammatory applications and its extracting method of the not fragrant lactone of 7 (11) alkene 12,8 of 6 hydroxyl Airies in Radix Ligulariae Dentatae | |
| CN105294623A (en) | Sesquiterpene lactone compound, preparation method and application thereof | |
| CN101250207B (en) | Canton love-pea vine total flavone c-glycosides effective part, preparation method and use thereof | |
| CN106866609A (en) | A kind of preparation method and application of noval chemical compound in Sabia parviflora Wall.ex Roxb | |
| Gul et al. | Formulations, characterization, in vitro and ex vivo release of Ephedra extract from topical preparations using dialysis cellulose membrane and natural rabbit skin | |
| CN102670631B (en) | Olive total phenylethanoid glycoside composition and preparation and application thereof | |
| Shang et al. | An integrated approach to reveal the chemical changes of Ligustri Lucidi Fructus during wine steaming processing | |
| CN105017345A (en) | Method for simultaneously extracting four kinds of compounds from selfheal, and application of extracted compounds | |
| CN103599144B (en) | The preparation method of jatamans valeriana rhizome epoxy iridoid ester active component | |
| CN101856435A (en) | Preparation method and content measurement method of Daphne giraldii Nitsche total coumarin extract | |
| CN106631747A (en) | Application of novel compound in preparation of liver protection drugs or health care products | |
| CN104906212B (en) | Raisin tree seed extract and its extraction separation method with hepatoprotective effect and purposes | |
| CN106117302A (en) | Six kinds of novel flavone saponin meroterpenoids compounds in Herba Clinopodii Polycephali | |
| Okpako et al. | Phytochemical screening and gas chromatography-mass spectrometry analysis of Euphorbia ingens organic root extract | |
| CN104557828B (en) | Method and the application thereof separating 6,8-dihydroxy-Airy Mo Fen-7 (11)-alkene-12,8-lactone is extracted from Radix Ligulariae Dentatae | |
| CN104387362A (en) | Iridoid ester compounds, and preparation method and application thereof | |
| de Araujo et al. | Crinum L. species as a potential source of alkaloids: Extraction methods and relevance for medicinal and pharmacological applications | |
| Iyekowa et al. | GC-MS Analysis and antiasthmatic activity of hexane extract of Phyllanthus amarus (Chancapiedra) L in Guinea pig | |
| CN109575102A (en) | The application of trilliaceae total steroidal saponin and wherein steroid saponin compound in preparation treatment ulcerative colitis drug | |
| CN103893412A (en) | Anti-tumor callicarpa nudiflora extract and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160824 Termination date: 20210123 |