CN105884722B - A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis - Google Patents

A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis Download PDF

Info

Publication number
CN105884722B
CN105884722B CN201610267846.0A CN201610267846A CN105884722B CN 105884722 B CN105884722 B CN 105884722B CN 201610267846 A CN201610267846 A CN 201610267846A CN 105884722 B CN105884722 B CN 105884722B
Authority
CN
China
Prior art keywords
methanol
carbon dioxide
chromatographic column
herba andrographitis
supercritical carbon
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.)
Active
Application number
CN201610267846.0A
Other languages
Chinese (zh)
Other versions
CN105884722A (en
Inventor
秦秀秀
孙爱玲
李爱峰
王延翠
柳仁民
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Liaocheng University
Original Assignee
Liaocheng University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Liaocheng University filed Critical Liaocheng University
Priority to CN201610267846.0A priority Critical patent/CN105884722B/en
Publication of CN105884722A publication Critical patent/CN105884722A/en
Application granted granted Critical
Publication of CN105884722B publication Critical patent/CN105884722B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • 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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/58—One oxygen atom, e.g. butenolide
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Abstract

The invention belongs to chemical industry and pharmaceutical field, is related to a kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Andrographis Paniculata.Herba Andrographitis pulverizing medicinal materials, absolute methanol refluxing extraction is added, extract solution is filtered, be concentrated under reduced pressure to obtain medicinal extract.Creat extract again with methanol is dissolved, after filtering, carries out supercritical fluid chromatography separation, chromatographic column SpherigelC18Chromatographic column, mobile phase are supercritical fluid, and modifying agent is methanol.Supercritical carbon dioxide is used in purge process of the present invention, without using the organic solvent for having harm to environment, production process is green, products obtained therefrom unharmful substance residual.

Description

A kind of andrographolide and Dehydro and drographolide of being isolated and purified from Herba Andrographitis Method
Technical field
The invention belongs to chemical industry and pharmaceutical field, is specifically related to one kind and Herba Andrographitis is isolated and purified from Andrographis Paniculata The supercritical fluid chromatography method of lactone and Dehydro and drographolide.
Background technology
Herba Andrographitis is acanthaceous plant Herba Andrographitis Andrographis paniculata (Burm.f.) Nees. drying Aerial part, there is clearing heat and detoxicating, cool blood, detumescence and other effects, be usually used in treating the diseases such as cold, fever, abscess of throat.In addition, wear Heart lotus is clinically mainly used in treating the diseases such as respiratory tract infection, acute bacillary dysentery, enterogastritis, also has and prevents and treats cardiovascular disease The multi-efficiency such as sick, antitumor, hepatic cholagogic, immunological regulation.
At present, silica gel column chromatography or macroreticular resin mainly are used to isolating and purifying for Diterpenes constituents in Herba Andrographitis Isolate and purify method.Silica gel column chromatography technical maturity, but it is cumbersome；Macroreticular resin isolates and purifies method and macroreticular resin need to be carried out Pretreatment, complex operation.In addition, silica gel column chromatography and macroreticular resin isolate and purify method, to be required to consumption substantial amounts of organic molten Agent, organic solvent cost recovery is high, and recycling is more difficult, and organic reagent residual is serious in product.
The content of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide one kind is easy to operate, fractional dose is big, integrated cost The method that low, green fast purifying prepares andrographolide and Dehydro and drographolide, isolated and purified i.e. by a step High-purity andrographolide and Dehydro and drographolide monomeric compound can be obtained from Andrographis Paniculata.
The solution of the present invention is as follows：
A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis, step are as follows：
Step 1：Herba Andrographitis pulverizing medicinal materials, absolute methanol refluxing extraction is added, extract solution is filtered, be concentrated under reduced pressure to obtain punching Lotus medicinal extract.
Step 2：Creat extract is dissolved with methanol, after filtering, carries out supercritical fluid chromatography separation, chromatographic column point Wei not SpherigelC18Chromatographic column, KromasilNH2Chromatographic column and glycol-based chromatographic column, mobile phase are supercritical fluid, modified Agent is organic solvent.Separation process is detected by UV-detector, and target components cut is collected according to detection signal.
Foregoing method, preferable scheme are that the ratio of absolute methanol refluxing extraction ethanol and medicinal material is in step 1 5：1~20：1, optimal is 10：1；The number of extraction is 3 times, and return time is 0.5-2 hours.
Foregoing method, preferable scheme are that filter membrane used in filtering is 0.45 μm of filter membrane in step 2.
Foregoing method, preferable scheme are that the species of chromatographic column is SpherigelC in step 218Chromatographic column, KromasilNH2Chromatographic column and glycol-based chromatographic column, optimal is SpherigelC18Chromatographic column.
Foregoing method, preferable scheme are that the species of modifying agent is methanol, ethanol, isopropanol and second in step 2 Nitrile, optimal is methanol.
Foregoing method, preferable scheme are that the ratio of modifying agent methanol is 4% ~ 6% in step 2, optimal to be 5.5%。
Foregoing method, preferable scheme are that supercritical fluid is supercritical carbon dioxide in step 2, overcritical The pressure of carbon dioxide is 11 ~ 15MPa, and optimal is 12MPa；The flow velocity of supercritical carbon dioxide is 1-10 times of column volume/minute, Optimal is 3 times of column volume/minutes.
Foregoing method, preferable scheme are that chromatogram column temperature is 30 ~ 50 °C in step 2, and optimal is 45 °C.
A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Andrographis Paniculata of the present invention, tool There is following advantage：
（1）Active constituent content is high in resulting Andrographis Paniculata（As can be seen from Figure 1）.
（2）Separating for several times purifying need not be carried out to sample as prior art, it is only necessary to a separating step Two kinds of high-purity compounds are obtained, is isolated and purified by a step and can be obtained by andrographolide and Dehydro and drographolide.
（3）Supercritical carbon dioxide is used in purge process, without using the organic solvent for having harm to environment, production process It is green, products obtained therefrom unharmful substance residual.
（4）Carbon dioxide recovery is using easily, and energy consumption is low, and production cost is low.
（5）Method is simple to operate, is easy to Automated condtrol, efficiency high, and process cycle is short.
Brief description of the drawings
Fig. 1 is the supercritical fluid chromatography figure of embodiment 1.
Embodiment
Technical scheme is described in detail with reference to embodiment and accompanying drawing, but protection domain is not limited by this.It is real Applying device therefor or raw material in example can all obtain from market.Agents useful for same is that analysis is pure, used purchased from the factory of Tianjin reagent four Carbon dioxide is high-purity carbon dioxide.
Embodiment 1
200 grams of Herba Andrographitis is weighed, is crushed, is put into glass container with pulverizer, the backflow of 2000ml absolute methanols is added and carries Take 0.5 hour, extract 3 times, extract solution is filtered, be concentrated under reduced pressure to obtain medicinal extract.
Creat extract is dissolved with methanol, after filtering, carries out supercritical fluid chromatography separation, chromatographic column is SpherigelC18Chromatographic column, chromatogram column temperature are 45 °C.Mobile phase is supercritical carbon dioxide, flow velocity be 3 times of column volumes/point Clock, pressure 12MPa.Modifying agent is methanol, and its ratio is 5.5%.Separation process is detected by UV-detector, and Detection wavelength is 225nm, target components cut is collected according to detection signal, respectively obtains andrographolide and Dehydro and drographolide.
Embodiment 2
200 grams of Herba Andrographitis is weighed, is crushed, is put into glass container with pulverizer, the backflow of 1000ml absolute methanols is added and carries Take 1 hour, extract 3 times, extract solution is filtered, be concentrated under reduced pressure to obtain medicinal extract.
Creat extract is dissolved with methanol, after filtering, carries out supercritical fluid chromatography separation, chromatographic column is SpherigelC18Chromatographic column, chromatogram column temperature are 40 °C.Mobile phase is supercritical carbon dioxide, flow velocity be 2 times of column volumes/point Clock, pressure 11MPa.Modifying agent is methanol, and its ratio is 4%.Separation process is detected by UV-detector, and Detection wavelength is 225nm, target components cut is collected according to detection signal, respectively obtains andrographolide and Dehydro and drographolide.
Embodiment 3
200 grams of Herba Andrographitis is weighed, is crushed, is put into glass container with pulverizer, the backflow of 3000ml absolute methanols is added and carries Take 2 hours, extract 3 times, extract solution is filtered, be concentrated under reduced pressure to obtain medicinal extract.
Creat extract is dissolved with methanol, after filtering, carries out supercritical fluid chromatography separation, chromatographic column is SpherigelC18Chromatographic column, chromatogram column temperature are 50 °C.Mobile phase is supercritical carbon dioxide, flow velocity be 2 times of column volumes/point Clock, pressure 13MPa.Modifying agent is methanol, and its ratio is 4.5%.Separation process is detected by UV-detector, and Detection wavelength is 225nm, target components cut is collected according to detection signal, respectively obtains andrographolide and Dehydro and drographolide.
Analyze and test through HPLC area normalization methods, the purity of each component obtained by embodiment 1-3 is very high, exists More than 98%.
Identified through NMR, MS, A is Dehydro and drographolide in Fig. 1, and B is andrographolide, and its chemical constitution is as follows：

Claims (7)

1. a kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis, it is characterized in that, step is such as Under：
Step 1：Herba Andrographitis pulverizing medicinal materials, absolute methanol refluxing extraction is added, extract solution is filtered, be concentrated under reduced pressure to obtain Herba Andrographitis leaching Cream；The ratio of absolute methanol and medicinal material is 5：1~20：1；The number of extraction is 3 times, and return time is 0.5-2 hours；
Step 2：Creat extract is dissolved with methanol, after filtering, filter membrane used in filtering is 0.45 μm of filter membrane, carries out super face Boundary's Fluid Chromatography separation, chromatographic column SpherigelC18Chromatographic column, mobile phase are supercritical fluid, and modifying agent is methanol；Separation Process is detected by UV-detector, and target components cut is collected according to detection signal；Supercritical fluid is supercritical carbon dioxide, The pressure of supercritical carbon dioxide is 11 ~ 15MPa；The flow velocity of supercritical carbon dioxide is 1-10 times of column volume/minute；Chromatographic column Temperature is 30 ~ 50 °C.
2. according to the method for claim 1, it is characterized in that, the ratio of absolute methanol and medicinal material is 10 in step 1：1.
3. according to the method for claim 1, it is characterized in that, the ratio of modifying agent methanol is 4% ~ 6% in step 2.
4. according to the method for claim 1, it is characterized in that, the ratio of modifying agent methanol is 5.5% in step 2.
5. according to the method for claim 1, it is characterized in that, the pressure of supercritical carbon dioxide is 12MPa in step 2.
6. according to the method for claim 1, it is characterized in that, the flow velocity of supercritical carbon dioxide is 3 times of cylinders in step 2 Product/minute.
7. according to the method for claim 1, it is characterized in that, chromatogram column temperature is 45 DEG C in step 2.
CN201610267846.0A 2016-04-27 2016-04-27 A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis Active CN105884722B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610267846.0A CN105884722B (en) 2016-04-27 2016-04-27 A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610267846.0A CN105884722B (en) 2016-04-27 2016-04-27 A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis

Publications (2)

Publication Number Publication Date
CN105884722A CN105884722A (en) 2016-08-24
CN105884722B true CN105884722B (en) 2018-03-13

Family

ID=56705301

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610267846.0A Active CN105884722B (en) 2016-04-27 2016-04-27 A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis

Country Status (1)

Country Link
CN (1) CN105884722B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108663454B (en) * 2018-06-11 2021-04-16 梧州市食品药品检验所 Rapid detection method capable of simultaneously quantifying gallic acid, andrographolide and dehydroandrographolide in compound andrographis tablet
CN113209194B (en) * 2021-06-10 2022-05-24 甘肃扶正药业科技股份有限公司 Composition for treating chronic gastritis and preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101168537A (en) * 2007-07-06 2008-04-30 中国热带农业科学院热带生物技术研究所 Method for simultaneously preparing andrographolide and dehydrated andrographolide
WO2009059158A1 (en) * 2007-11-02 2009-05-07 Hutchison Medipharma Enterprises Limited Andrographis paniculata extract
CN101671322A (en) * 2009-09-30 2010-03-17 合肥工业大学 Method for separating and purifying andrograholide
CN104311515A (en) * 2014-09-04 2015-01-28 桂林甙元生物科技有限公司 Separation and extraction technology of andrographolide and dehydroandrographolide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101168537A (en) * 2007-07-06 2008-04-30 中国热带农业科学院热带生物技术研究所 Method for simultaneously preparing andrographolide and dehydrated andrographolide
WO2009059158A1 (en) * 2007-11-02 2009-05-07 Hutchison Medipharma Enterprises Limited Andrographis paniculata extract
CN101671322A (en) * 2009-09-30 2010-03-17 合肥工业大学 Method for separating and purifying andrograholide
CN104311515A (en) * 2014-09-04 2015-01-28 桂林甙元生物科技有限公司 Separation and extraction technology of andrographolide and dehydroandrographolide

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Isolation of Plant Products by Supercritical-fluid Extraction;Andrew P. Jarvis et al;《PHYTOCHEMICAL ANALYSIS》;19971231;第8卷;第217-222页 *
SFC分离技术及其在分离纯化领域中的应用;蔡锦源等;《轻工科技》;20121231(第12期);第24-25页 *
丹参和穿心莲的超临界二氧化碳萃取应用研究;龚春晖等;《中国药学杂志》;20001130;第35卷;第43-56页 *
制备型超临界流体色谱及其进展;姚渭溪等;《第三届全国超临界流体技术学术及应用研讨会论文集》;20070816;第363-366页 *
超临界流体色谱及其应用研究进展;成亮等;《中草药》;20071231;第38卷;第295-298页 *
超临界流体色谱的研究进展;陈青等;《分析化学》;20040825;第32卷(第8期);第1104-1109页 *

Also Published As

Publication number Publication date
CN105884722A (en) 2016-08-24

Similar Documents

Publication Publication Date Title
CN107337586B (en) Method for extracting and purifying cannabidiol from China hemp
CN109942380B (en) Method for preparing cannabidiol by high-speed counter-current chromatography separation and purification
CN101508715B (en) Extraction and purification process for cordycepin in cordyceps militaris link
CN103145677B (en) Method for separating active ingredients from aquilaria sinensis lamina by utilizing high-speed countercurrent chromatography
CN107216228B (en) Eutectic solvent and method for extracting anthraquinone in rheum officinale
CN102976909A (en) Method for extracting and purifying 6-gingerol from ginger
CN104402950B (en) A kind of picroside Ⅰ crystallization preparation method
CN107628959A (en) Choline eutectic solvent, preparation method and the application in trollflower flavone c-glycoside is extracted
CN112010738B (en) Industrial method for producing cannabinoid compound by utilizing chromatographic separation
CN105884722B (en) A kind of method that andrographolide and Dehydro and drographolide are isolated and purified from Herba Andrographitis
CN1935798B (en) Method for preparing and rographalide
CN104817445B (en) A kind of isolated and purified physcione and method of rheum emodin from Rhizoma Polygoni Cuspidati
CN101525328B (en) Method for extracting alpha-mangostin from mangosteen fruit peel
CN103265536A (en) Preparation method of swertisin
CN103772460B (en) The extraction process of cordycepin in silkworm Chinese caterpillar fungus
CN106496292A (en) A kind of method for preparing 6 iridoid glycoside constituents from Fructus Gardeniae simultaneously
CN105859715A (en) Critical fluid chromatographic method for separating and purifying evodiamine and rutaecarpine from fructus evodiae
CN105837546B (en) A kind of method that alnusenone, pinocembrin, cardamomin, Alpinetin are isolated and purified from one's early teens
CN102617674B (en) Preparation method of scopolin monomer in anisodus tanguticus root
CN104447668A (en) Method for preparing high-purity EGCG from hydrogen-bonded macroporous resin
CN104844550B (en) A kind of method that osthole and imperatorin are isolated and purified from Fructus Cnidii
CN105906687B (en) A kind of method that a variety of tanshinone monomer components are isolated and purified from the red sage root
CN104961716A (en) Method for separating high-purity lactone type lovastatin from fermentum rubrum powder
CN1994995A (en) Method for extracting and purifying sequoyitol
CN103275054A (en) Method for preparing bellidifolin

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant