CN104292291A - Preparation method of acetyl lantanolic acid - Google Patents
Preparation method of acetyl lantanolic acid Download PDFInfo
- Publication number
- CN104292291A CN104292291A CN201410465998.2A CN201410465998A CN104292291A CN 104292291 A CN104292291 A CN 104292291A CN 201410465998 A CN201410465998 A CN 201410465998A CN 104292291 A CN104292291 A CN 104292291A
- Authority
- CN
- China
- Prior art keywords
- acetyl
- lantanolic
- ethanol
- preparation
- lantanolic acid
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a preparation method of acetyl lantanolic acid. The preparation method is characterized by comprising the steps such as supercritical extraction, polyamide column chromatography, aluminum oxide column chromatography and recrystallization. The preparation method disclosed by the invention is mild in condition, reasonable in process, capable of avoiding the adverse effect of a local high temperature on the product activity in the conventional method, and capable of realizing quick extracting, separating and purifying, and is a method suitable for large-scale production.
Description
Technical field
The invention belongs to natural medicine field, be specifically related to a kind of preparation method of acetyl lantanolic acid.
Background technology
Acetyl lantanolic acid (Camarinic acid), colorless needles, mp.204-205 DEG C, molecular formula is C
32h
48o
6, molecular weight is 528.73, and structural formula is:
Acetyl lantanolic acid is separated to obtain a kind of triterpene compound from Verbenaceae (Verbenaceae) Lantana camara Lantana camara Linn. over-ground part.Pharmacological research shows, acetyl lantanolic acid has anti-microbial effect, has anti-microbial activity to streptococcus aureus and Salmonella typhi; There is high antimutagenicity.
In prior art, there is not yet the production technique report of preparation acetyl lantanolic acid.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of acetyl lantanolic acid, adopt supercritical CO
2the steps such as extraction, polyamide column chromatography, alumina column chromatography and recrystallization, from the over-ground part of Lantana camara be separated obtain crying highly purified acetyl lantanolic acid, the method extraction acetyl lantanolic acid purity high, be produced on a large scale.
The present invention is achieved by the following technical solutions:
A preparation method for acetyl lantanolic acid, is characterized in that comprising the following steps:
1) supercritical extraction: the over-ground part pulverizing medicinal materials of getting Lantana camara, puts into supercritical CO
2in extraction kettle, then add appropriate organic solvent as entrainment agent, pass into CO
2, at extracting pressure 20-35MPa, extract under extraction temperature 30-50 DEG C of condition, CO
2flow velocity is 10-30L/h, carries out extraction 1-3h, collects extract;
2) polyamide column chromatography: extract is added in polyamide resin column, coutroi velocity 0.5-1.5BV/h, first washes with water to colourless, use 30-90% ethanol gradient elution again, collect elutriant, be concentrated into relative density 1.08-1.12, obtain acetyl lantanolic acid crude extract;
3) alumina column chromatography: the acidic alumina of acetyl lantanolic acid crude extract by 3-4 times amount is adsorbed, less than 50 DEG C oven drying at low temperatures, dry column-packing, organic solvent gradient elution, collects the flow point containing high-content acetyl lantanolic acid, is evaporated to small volume, crystallization, obtains coarse-grain;
4) recrystallization: coarse-grain is used methanol aqueous solution recrystallization, obtains highly purified acetyl lantanolic acid monomeric compound.
Step (1) described entrainment agent is ethanol or the acetone soln of 60-90%, and add-on is the 5-15% being equivalent to raw material weight.
Organic solvent described in step (3) is ethyl acetate-ethanol, ethanol, and ethyl acetate-ethanol volume ratio is 1:2.
Feature of the present invention is: the inventive method adopts supercritical fluid extraction; mild condition, avoids the disadvantageous effect of traditional method localized hyperthermia to Product Activity, rational technology; can realize rapid extraction, separation, purifying, be a kind of method being suitable for large-scale production.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, and the following example is intended to citing and describes the present invention, instead of limits the present invention by any way.
Embodiment 1:
By the over-ground part pulverizing medicinal materials of Lantana camara, get 5kg and drop in supercritical extraction tank, add volume percent be the ethanolic soln of 80% as entrainment agent, add-on is 6% of 0.3kg(raw material weight), at extracting pressure 25MPa, extraction temperature 45 DEG C, CO
22h is extracted under flow 18L/h condition, obtain the over-ground part extract of Lantana camara, extract hot water disperses, upper polyamide resin column, flow velocity 1.0BV/h, first wash with water to water lotion colourless, use 30% ethanol elution again, finally use 80% ethanol elution, collect 80% ethanol eluate, elutriant being evaporated to relative density is 1.08, obtain acetyl lantanolic acid crude extract, by acetyl lantanolic acid crude extract dissolve with methanol, mix with the acidic alumina of 3 times amount, in 50 DEG C of oven drying at low temperatures, dry method upper prop, use ethyl acetate-ethanol (1:2) successively, ethanol elution, thin-layer chromatography checks, collect high-content acetyl lantanolic acid flow point, be evaporated to small volume, crystallization, by coarse-grain 80% methanol aqueous solution recrystallization, obtain 532mg acetyl lantanolic acid monomeric compound, its content is 98.7%.
Embodiment 2:
By the over-ground part pulverizing medicinal materials of Lantana camara, get 5kg and drop in supercritical extraction tank, add volume percent be the ethanolic soln of 70% as entrainment agent, add-on is 12% of 0.6kg(raw material weight), at extracting pressure 20MPa, extraction temperature 35 DEG C, CO
21h is extracted under flow 20L/h condition, obtain the over-ground part extract of Lantana camara, extract hot water disperses, upper polyamide resin column, flow velocity 1.5BV/h, first wash with water to water lotion colourless, use 30% ethanol elution again, finally use 90% ethanol elution, collect 90% ethanol eluate, elutriant being evaporated to relative density is 1.10, obtain acetyl lantanolic acid crude extract, by acetyl lantanolic acid crude extract dissolve with methanol, mix with the acidic alumina of 3 times amount, in 45 DEG C of oven drying at low temperatures, dry method upper prop, with using ethyl acetate-ethanol (1:2) successively, ethanol elution, thin-layer chromatography checks, collect high-content acetyl lantanolic acid flow point, be evaporated to small volume, crystallization, by coarse-grain 80% methanol aqueous solution recrystallization, obtain 529mg acetyl lantanolic acid monomeric compound, its content is 98.0%.
Embodiment 3:
By the over-ground part pulverizing medicinal materials of Lantana camara, get 5kg and drop in supercritical extraction tank, add volume percent be the acetone soln of 90% as entrainment agent, add-on is 15% of 0.75kg(raw material weight), at extracting pressure 32MPa, extraction temperature 30 DEG C, CO
23h is extracted under flow 10L/h condition, obtain the over-ground part extract of Lantana camara, extract hot water disperses, upper polyamide resin column, flow velocity 1.2BV/h, first wash with water to water lotion colourless, use 30% ethanol elution again, finally use 70% ethanol elution, collect 70% ethanol eluate, elutriant being evaporated to relative density is 1.12, obtain acetyl lantanolic acid crude extract, by acetyl lantanolic acid crude extract dissolve with methanol, mix with the acidic alumina of 3 times amount, in 40 DEG C of oven drying at low temperatures, dry method upper prop, use ethyl acetate-ethanol (1:2) successively, ethanol elution, thin-layer chromatography checks, collect high-content acetyl lantanolic acid flow point, be evaporated to small volume, crystallization, by coarse-grain 80% methanol aqueous solution recrystallization, obtain 533mg acetyl lantanolic acid monomeric compound, its content is 98.2%.
Embodiment 4:
By the over-ground part pulverizing medicinal materials of Lantana camara, get 5kg and drop in supercritical extraction tank, add volume percent be the acetone soln of 60% as entrainment agent, add-on is 10% of 0.5kg(raw material weight), at extracting pressure 35MPa, extraction temperature 50 DEG C, CO
22h is extracted under flow 30L/h condition, obtain the over-ground part extract of Lantana camara, extract hot water disperses, upper polyamide resin column, flow velocity 0.5BV/h, first wash with water to water lotion colourless, use 40% ethanol elution again, finally use 90% ethanol elution, collect 90% ethanol eluate, elutriant being evaporated to relative density is 1.11, obtain acetyl lantanolic acid crude extract, by acetyl lantanolic acid crude extract dissolve with methanol, mix with the acidic alumina of 4 times amount, in 45 DEG C of oven drying at low temperatures, dry method upper prop, use ethyl acetate-ethanol (1:2) successively, ethanol elution, thin-layer chromatography checks, collect high-content acetyl lantanolic acid flow point, be evaporated to small volume, crystallization, by coarse-grain 80% methanol aqueous solution recrystallization, obtain 509mg acetyl lantanolic acid monomeric compound, its content is 97.8%.
Claims (3)
1. a preparation method for acetyl lantanolic acid, is characterized in that comprising the following steps:
1) supercritical extraction: the over-ground part pulverizing medicinal materials of getting Lantana camara, puts into supercritical CO
2in extraction kettle, then add appropriate organic solvent as entrainment agent, pass into CO
2, at extracting pressure 20-35MPa, extract under extraction temperature 30-50 DEG C of condition, CO
2flow velocity is 10-30L/h, carries out extraction 1-3h, collects extract;
2) polyamide column chromatography: extract is added in polyamide resin column, coutroi velocity 0.5-1.5BV/h, first washes with water to colourless, use 30-90% ethanol gradient elution again, collect elutriant, be concentrated into relative density 1.08-1.12, obtain acetyl lantanolic acid crude extract;
3) alumina column chromatography: the acidic alumina of acetyl lantanolic acid crude extract by 3-4 times amount is adsorbed, less than 50 DEG C oven drying at low temperatures, dry column-packing, organic solvent gradient elution, collects the flow point containing high-content acetyl lantanolic acid, is evaporated to small volume, crystallization, obtains coarse-grain;
4) recrystallization: coarse-grain is used methanol aqueous solution recrystallization, obtains highly purified acetyl lantanolic acid monomeric compound.
2. the preparation method of a kind of acetyl lantanolic acid according to claim 1, is characterized in that, step (1) described entrainment agent is ethanol or the acetone soln of 60-90%, and add-on is the 5-15% being equivalent to raw material weight.
3. the preparation method of a kind of acetyl lantanolic acid according to claim 1, is characterized in that, the organic solvent described in step (3) is ethyl acetate-ethanol, ethanol, and ethyl acetate-ethanol volume ratio is 1:2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410465998.2A CN104292291A (en) | 2014-09-15 | 2014-09-15 | Preparation method of acetyl lantanolic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410465998.2A CN104292291A (en) | 2014-09-15 | 2014-09-15 | Preparation method of acetyl lantanolic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104292291A true CN104292291A (en) | 2015-01-21 |
Family
ID=52312271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410465998.2A Pending CN104292291A (en) | 2014-09-15 | 2014-09-15 | Preparation method of acetyl lantanolic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104292291A (en) |
-
2014
- 2014-09-15 CN CN201410465998.2A patent/CN104292291A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101033244B (en) | Method of purifying and preparing momordica grosvenori alcohol | |
| CN102633861A (en) | Preparation method of physalin B | |
| CN112209979B (en) | Production process for jointly separating high-purity glycyrrhizin, debitterized glycyrrhizin and total flavonoids from monoammonium glycyrrhizinate mother liquor | |
| CN102276665A (en) | Method of extracting flax lignin from flax seed cake | |
| CN103467539B (en) | A kind of method extracting Rosavin from rose-red red-spotted stonecrop | |
| CN103265521A (en) | Preparation method of demethylated beilidifolin | |
| CN104231011B (en) | Preparation method of verbascoside | |
| CN104292291A (en) | Preparation method of acetyl lantanolic acid | |
| CN102504007A (en) | Method for separation and purification of ruscogenin monomer | |
| CN101967505A (en) | Method for preparing dihydro quercetin | |
| CN104072375A (en) | Preparation method of thamnolic acid | |
| CN103467558A (en) | Method for preparing pomolic acid | |
| CN106279301B (en) | A method of recycling aurantiamarin methyl chalcone from hesperidin methyl mother liquor | |
| CN102241656A (en) | Preparation method of tricin | |
| CN102373248A (en) | Method for purifying biochanin A | |
| CN102233073A (en) | Preparation method of flavonoid extract of rhizoma arisaematis | |
| CN104072472A (en) | Preparation method of plagiochin E | |
| CN102627540A (en) | Alnustone purification method | |
| CN103435630A (en) | Preparation method of liatrin | |
| CN102320959A (en) | The preparation method of a kind of chrysanthemumic acid B that goes to the field | |
| CN114014828B (en) | Method for recovering quercetin from stevioside extraction residues and application of quercetin | |
| CN102603764A (en) | Extraction method of columbin | |
| CN101775419A (en) | Method for extracting suquassine from Lespedeza kunmingensis of Leguminosae | |
| CN104292081A (en) | Method for extracting batatasin from plant Chinese yam | |
| CN104910244A (en) | Bemeuxin preparation method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20150121 |