CN101020638A - 1'-acetoxy chavicol acetic ester - Google Patents
1'-acetoxy chavicol acetic ester Download PDFInfo
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- CN101020638A CN101020638A CNA2007100851649A CN200710085164A CN101020638A CN 101020638 A CN101020638 A CN 101020638A CN A2007100851649 A CNA2007100851649 A CN A2007100851649A CN 200710085164 A CN200710085164 A CN 200710085164A CN 101020638 A CN101020638 A CN 101020638A
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- acetoxychavicol acetate
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- 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
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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Abstract
The present invention discloses a supercritical CO2 extraction and silica gel column chromatographic process for extracting, separating and refining 1'-acetoxy chavicol acetic ester with activity of resisting tubercle bacillus infection from dried galangal rhizome as one kind of Zingiberaceae plant.
Description
Technical field
The present invention relates to a kind of application of extraction separation purified 1 '-acetoxychavicol acetate in preparation tubercule bacillus inhibitor from the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd. with supercritical carbon dioxide extraction and silica gel column chromatography production method.
Background technology
The English 1 '-acetoxychavicol acetate by name of 1 '-acetoxychavicol acetate, molecular formula is C
13H
14O
4, molecular weight is 234.25, structural formula is
On August 10th, 2006, Japanese Patent JP2006206541 discloses 1 '-acetoxychavicol acetate chemical synthesis process.On July 7th, 2005, Japanese Patent JP2005179201 discloses 1 '-acetoxychavicol acetate that separation obtains from the methanol extract of Rhizoma Alpiniae Galangae fruit and has had the duplicate effect of the HIV-1NL43 of inhibition in the MT-4 cell, and the MT-4 cell survival is not had influence, show the characteristics of tight security and the external migration of inhibition HIV Rev pyrenoids.Also have the research report show 1 '-acetoxychavicol acetate have antitumor (Moffatt J, A, et al.[J] .Carcinogenesis, 2000,21:2151-2157; Zheng Q et al.[J] .J Cancer Res Clin Oncol, 2002,128:539～546), antibacterium (Janssen A M, [J] .planta Med, 1985 (6): 507～511), antimycotic (Ficker C E, etal.[J] .J Ethnophamacal, 2003,85:589～593), antiulcer agent (Mitsuis, etal.[J] .Chem Pham Bull, 1976,24:2377～2382), anti-oxidant (Kubota K, etal.[J] .Spec Publ R Soc Chem, 2001,274:601～607), anti-inflammatory (NakamuraY, [J] .Cancer Res, 1998,58:4832～4839) biological activity such as, but do not see the research report of the refining 1 '-acetoxychavicol acetate of extraction separation from the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpiniagalanga Willd., do not see the report that 1 '-acetoxychavicol acetate is used yet in preparation tubercule bacillus inhibitor with supercritical carbon dioxide extraction and silica gel column chromatography production method.
Summary of the invention
The technical issues that need to address of the present invention are, provide a kind of with supercritical carbon dioxide extraction and the silica gel column chromatography production method that extraction separation is made with extra care 1 '-acetoxychavicol acetate from the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd., and the application of 1 '-acetoxychavicol acetate in preparation tubercule bacillus inhibitor.Technical scheme is as follows:
Get the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd., be dried to and contain moisture less than 10%, be ground into 10～60 order fine powders, put in the supercritical carbon dioxide extraction device, the extraction kettle temperature is 30 ℃～60 ℃, and pressure is 10Mpa～25Mpa; The separator column temperature is 30 ℃～60 ℃, and pressure is 8Mpa～20Mpa; The extraction-container temperature is 30 ℃～60 ℃, and pressure is 8Mpa～20Mpa; Carbon dioxide flow is 50～5000L/ hour; The extracting and separating time is 1～6 hour.
Get above-mentioned extracting and separating liquid cross silica gel column chromatography, with 5～10: normal hexane-eluent ethyl acetate of 1 is refining, collects the wash-out refined liquid, and the reduced vacuum drying promptly gets 1 '-acetoxychavicol acetate.Adopt the conventional formulation method, 1 '-acetoxychavicol acetate is made soft capsule, tablet, capsule, pill, granule, injection in medicine, use.
Adopt following method to detect beneficial effect of the present invention:
1. structural identification test: adopt the structure that ultimate analysis, ultra-violet absorption spectrum, infrared absorption spectrum, mass spectrum, nuclear magnetic resonance spectrum are resolved and conclusive evidence extraction separation of the present invention is made with extra care the compound that obtains.
2. purity testing
Measure according to high performance liquid chromatography (appendix VID of Chinese Pharmacopoeia version in 2005).
Chromatographic condition and system suitability test are weighting agent with the octadecylsilane chemically bonded silica; With methanol-water (50: 50) is moving phase; The detection wavelength is 254nm.Number of theoretical plate calculates by 1 '-acetoxychavicol acetate peak should be not less than 3000.
1 '-acetoxychavicol acetate reference substance 0.1g is got in the preparation of reference substance solution, the accurate title, decide, put in the 50ml measuring bottle, add methyl alcohol and be diluted to scale, shake up, precision is measured 0.1ml, put in the 10ml measuring bottle, add moving phase and be diluted to scale, shake up, promptly get (every 1ml contains 1 '-acetoxychavicol acetate, 20 μ g).
The about 0.1g of this product is got in the preparation of need testing solution, and accurate the title decides, and puts in the 50ml measuring bottle, adds methyl alcohol to scale, shakes up, and precision is measured 0.1ml, puts in the 10ml measuring bottle, adds moving phase and is diluted to scale, shakes up, and filters, and gets subsequent filtrate, promptly.
Accurate respectively reference substance and each the 20 μ l of need testing solution of drawing of assay method inject liquid chromatograph, measure, and calculate by external standard method, promptly.
3. tubercle bacillus resistant activity is measured
(1) minimal inhibitory concentration (MIC) is measured: get tubercule bacillus, Bacillus tuberculosis bovis, strong malicious Bacillus tuberculosis (H37RV) nutrient solution and be inoculated in the simple synthetic medium test tube of tubercule bacillus, the 1 '-acetoxychavicol acetate methanol solution that adds different concns, shake up, cultivated 14 days for 37 ℃, observe each duct ligation nuclear bacillus growing state, calculate the minimal inhibitory concentration (MIC) of 1 '-acetoxychavicol acetate each tubercule bacillus.
(2) 1 '-acetoxychavicol acetates are to infecting the provide protection of tubercule bacillus mouse: getting body weight is that 16～18g is through the negative mouse of tuberculosin test-results; male and female half and half; random packet behind every intravenous injection inoculation H37RV tubercule bacillus nutrient solution 0.2ml; mouse gives 1 '-acetoxychavicol acetate at the 3rd day beginning oral administration gavage that vein infects; every day 3 times; for three days on end, observe the death time T of half animal
50, and with physiological saline blank group and vazadrine positive controls relatively.
Embodiment
Embodiment 1
Get the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd., be dried to and moisturely be divided into 5.6%, be ground into 18 order fine powders, put in the supercritical carbon dioxide extraction device, the extraction kettle temperature is 33 ℃, and pressure is 15Mpa; The separator column temperature is 45 ℃, and pressure is 10Mpa; The extraction-container temperature is 36 ℃, and pressure is 8MPa; The carbonic acid gas instantaneous delivery is 200L/ hour; The extracting and separating time is 4 hours.Get above-mentioned extracting and separating liquid and cross silica gel column chromatography, refining with 10: 1 normal hexane-eluent ethyl acetates, collect the wash-out refined liquid, the reduced vacuum drying promptly gets compound 1 (1 '-acetoxychavicol acetate).Adopting the conventional formulation method that this compound (1 '-acetoxychavicol acetate) is made soft capsule, tablet, capsule, pill, granule, injection uses in medicine.
Embodiment 2
Get the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd., be dried to and moisturely be divided into 8.2%, be ground into 20 order fine powders, put in the supercritical carbon dioxide extraction device, the extraction kettle temperature is 38 ℃, and pressure is 20Mpa; The separator column temperature is 41 ℃, and pressure is 12Mpa; The extraction-container temperature is 32 ℃, and pressure is 10MPa; The carbonic acid gas instantaneous delivery is 250L/ hour; The extracting and separating time is 5 hours.Get above-mentioned extracting and separating liquid and cross silica gel column chromatography, refining with 10: 1 normal hexane-eluent ethyl acetates, collect the wash-out refined liquid, the reduced vacuum drying promptly gets compound 2 (1 '-acetoxychavicol acetate).Adopting the conventional formulation method that this compound (1 '-acetoxychavicol acetate) is made soft capsule, tablet, capsule, pill, granule, injection uses in medicine.
Embodiment 3
Get the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd., be dried to and moisturely be divided into 7.1%, be ground into 14 order fine powders, put in the supercritical carbon dioxide extraction device, the extraction kettle temperature is 40 ℃, and pressure is 10Mpa; The separator column temperature is 50 ℃, and pressure is 18Mpa; The extraction-container temperature is 45 ℃, and pressure is 15MPa; The carbonic acid gas instantaneous delivery is 150L/ hour; The extracting and separating time is 6 hours.Get above-mentioned extracting and separating liquid and cross silica gel column chromatography, refining with 10: 1 normal hexane-eluent ethyl acetates, collect the wash-out refined liquid, the reduced vacuum drying promptly gets compound 3 (1 '-acetoxychavicol acetate).Adopting the conventional formulation method that this compound (1 '-acetoxychavicol acetate) is made soft capsule, tablet, capsule, pill, granule, injection uses in medicine.
Embodiment 4
Get the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd., be dried to and moisturely be divided into 9.3%, be ground into 12 order fine powders, put in the supercritical carbon dioxide extraction device, the extraction kettle temperature is 45 ℃, and pressure is 25Mpa; The separator column temperature is 43 ℃, and pressure is 16Mpa; The extraction-container temperature is 38 ℃, and pressure is 12MPa; The carbonic acid gas instantaneous delivery is 500L/ hour; The extracting and separating time is 3 hours.Get above-mentioned extracting and separating liquid and cross silica gel column chromatography, refining with 5: 1 normal hexane-eluent ethyl acetates, collect the wash-out refined liquid, the reduced vacuum drying promptly gets compound 4 (1 '-acetoxychavicol acetate).Adopting the conventional formulation method that this compound (1 '-acetoxychavicol acetate) is made soft capsule, tablet, capsule, pill, granule, injection uses in medicine.
Embodiment 5
Get the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd., be dried to and moisturely be divided into 6.5%, be ground into 10 order fine powders, put in the supercritical carbon dioxide extraction device, the extraction kettle temperature is 55 ℃, and pressure is 18Mpa; The separator column temperature is 46 ℃, and pressure is 8Mpa; The extraction-container temperature is 55 ℃, and pressure is 14MPa; The carbonic acid gas instantaneous delivery is 1000L/ hour; The extracting and separating time is 2 hours.Get above-mentioned extracting and separating liquid and cross silica gel column chromatography, refining with 5: 1 normal hexane-eluent ethyl acetates, collect the wash-out refined liquid, the reduced vacuum drying promptly gets compound 5 (1 '-acetoxychavicol acetate).Adopting the conventional formulation method that this compound (1 '-acetoxychavicol acetate) is made soft capsule, tablet, capsule, pill, granule, injection uses in medicine.
Embodiment 6
Get the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd., be dried to and moisturely be divided into 4.1%, be ground into 40 order fine powders, put in the supercritical carbon dioxide extraction device, the extraction kettle temperature is 35 ℃, and pressure is 13Mpa; The separator column temperature is 40 ℃, and pressure is 14Mpa; The extraction-container temperature is 33 ℃, and pressure is 17MPa; The carbonoxide instantaneous delivery is 1500L/ hour; The extracting and separating time is 1 hour.Get above-mentioned extracting and separating liquid and cross silica gel column chromatography, refining with 5: 1 normal hexane-eluent ethyl acetates, collect the wash-out refined liquid, the reduced vacuum drying promptly gets compound 6 (1 '-acetoxychavicol acetate).Adopting the conventional formulation method that this compound (1 '-acetoxychavicol acetate) is made soft capsule, tablet, capsule, pill, granule, injection uses in medicine.
The beneficial effect that the present invention obtains:
1. structural identification test: the compound of getting above 6 embodiment preparation carries out the structural identification test, and the result is as follows:
1. ultimate analysis
Instrument model: German EAS Vario ELIII
Theoretical value: C%:66.67%, H:5.98%.
Detected value: 1) C%:66.92%, H%:6.27%
2)C％：66.87％，H％：6.29％
2. ultra-violet absorption spectrum
Instrument model: the UV-3400 of HIT
Detected value:
219.95nm:n the absorption peak that → π * transition produces is the uv-absorbing of ester group.
261.00nm: the absorption peak that π → π * transition produces is the absorption of phenyl ring.
3. infrared absorption spectrum
Instrument model: the NEXUS670 of U.S. Buddhist nun's high-tensile strength company
Detected value:
2933cm
-1C-Hst，1740cm
-1 C＝Ost，1644cm
-1 C＝Cst，
1234cm
-1 CO-Ostas，1205cm
-1 O-C-Cstas。
4. mass spectrum
Instrument model: the VARIAN2200 of U.S. Varian company
Detected value:
Obtain the fragment ion of following nucleo plasmic relation: 234,192,175,150,134.Wherein 234 is molions, sloughs nucleo plasmic relation and is 42 ethanoyl ion and obtain 192 fragment ion; It is that 59 acetate ion obtains 175 fragment ion that molion 234 is sloughed nucleo plasmic relation; It is that 42 ethanoyl ion obtains 150 fragment ion that molion 234 is sloughed 2 nucleo plasmic relations; It is that 16 oxonium ion obtains 134 fragment ion that 150 fragment ion is sloughed nucleo plasmic relation.
5. nuclear magnetic resonance spectrum
Instrument model: the AVANCE-400 of Switzerland Bruker company
Detected value:
1H-NMR(400MHz，CDCl
3)：7.390～7.368，7.099～7.078，6.287～6.272，6.010～5.953，5.333～5.239，2.283，2.104。
13C-NMR(400MHz，CDCl
3)：169.881，169.361，150.445，136.431，136.034，128.406，121.685，117.048，75.501，21.169，21.070。
Integration analysis: above test-results conclusive evidence the present invention extraction separation purified compound from the dry rhizome rhizome of Galanga Galangal of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd. is 1 '-acetoxychavicol acetate, and its molecular formula is C
13H
14O
4, molecular weight is 234.25, structural formula is
2.1 refining yield of '-acetoxychavicol acetate extraction separation and purity detecting result: 1 '-acetoxychavicol acetate of getting above 6 embodiment preparation detects, and the results are shown in Table 1.
Refining yield of table 11 '-acetoxychavicol acetate extraction separation and purity detecting result
3. tubercle bacillus resistant activity measurement result: 1 '-acetoxychavicol acetate of getting above 6 embodiment preparation carries out the tubercle bacillus resistant activity test.
(1) 1 '-acetoxychavicol acetate minimal inhibitory concentration (MIC) measurement result shows that 1 '-acetoxychavicol acetate all has remarkable restraining effect to three kinds of tubercule bacillus, sees Table 2.
Table 21 '-acetoxychavicol acetate MIC measurement result
| Bacterial classification | Tubercule bacillus | Bacillus tuberculosis (H 37Rv) | Bacillus tuberculosis bovis |
| MIC(μg/ml) | 20.1 | 82.3 | 132.4 |
(2) 1 '-acetoxychavicol acetates are to infecting the provide protection of tubercule bacillus mouse: the result shows that 1 '-acetoxychavicol acetate significant prolongation infects the death time of tubercule bacillus mouse, sees Table 3.
Table 31 '-acetoxychavicol acetate is to infecting the provide protection of tubercule bacillus mouse
| Group | Physiological saline blank group | The vazadrine positive controls | 1 '-acetoxychavicol acetate group |
| T 50(my god) | 15～20 | 45～50 | 50～62 |
Claims (5)
1.1 '-acetoxychavicol acetate is characterized in that having anti-active 1 '-acetoxychavicol acetate of nuclear coli infections short of money with supercritical carbon dioxide extraction and silica gel column chromatography production method extraction separation from rhizome of Galanga Galangal is refining.
2. the described 1 '-acetoxychavicol acetate of claim 1 is characterized in that using rhizome of Galanga Galangal, is dried to contain moisture less than 10%, be ground into 10～60 order fine powders, put in the supercritical carbon dioxide extraction device, the extraction kettle temperature is 30 ℃～60 ℃, and pressure is 10Mpa～25Mpa; The separator column temperature is 30 ℃～60 ℃, and pressure is 8Mpa～20Mpa; The extraction-container temperature is 30 ℃～60 ℃, and pressure is 8Mpa～20Mpa; Carbon dioxide flow is 50～5000L/ hour; The extracting and separating time is 1～6 hour; Get above-mentioned extracting and separating liquid cross silica gel column chromatography, with 5～10: normal hexane-eluent ethyl acetate of 1 is refining, collects the wash-out refined liquid, 1 '-acetoxychavicol acetate that reduced vacuum exsiccant method is produced.
3. the described 1 '-acetoxychavicol acetate of claim 1, the raw material rhizome of Galanga Galangal that it is characterized in that producing 1 '-acetoxychavicol acetate is the dry rhizome of Zingiber Zingiberaceae Alpinia plants Galanga Galangal Seed Alpinia galanga Willd..
4. the described 1 '-acetoxychavicol acetate of claim 1 is characterized in that the English of 1 '-acetoxychavicol acetate is called 1 '-acetoxychavicol acetate, and molecular formula is C
13H
14O
4, molecular weight is 234.25, structural formula is
5. the described 1 '-acetoxychavicol acetate of claim 1 is characterized in that soft capsule, tablet, capsule, pill, granule, the application of injection in preparation tubercule bacillus inhibitor made from 1 '-acetoxychavicol acetate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100851649A CN101020638A (en) | 2007-03-18 | 2007-03-18 | 1'-acetoxy chavicol acetic ester |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100851649A CN101020638A (en) | 2007-03-18 | 2007-03-18 | 1'-acetoxy chavicol acetic ester |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798266A (en) * | 2010-03-29 | 2010-08-11 | 南昌弘益科技有限公司 | Production method of 1'-acetoxyl chavicol acetic ester |
| CN104045553A (en) * | 2014-06-30 | 2014-09-17 | 苏州派腾生物医药科技有限公司 | Method for extracting 1'-acetoxychavicol acetate from Actinostemma tenerum Griff |
| CN104058963A (en) * | 2014-06-30 | 2014-09-24 | 苏州派腾生物医药科技有限公司 | Method for extracting 1'-acetoxychavicol acetate from alpinia chinensis |
| WO2022244691A1 (en) * | 2021-05-21 | 2022-11-24 | サントリーホールディングス株式会社 | Method for producing galangal extract containing 1'-acetoxychavicol acetate |
-
2007
- 2007-03-18 CN CNA2007100851649A patent/CN101020638A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798266A (en) * | 2010-03-29 | 2010-08-11 | 南昌弘益科技有限公司 | Production method of 1'-acetoxyl chavicol acetic ester |
| CN101798266B (en) * | 2010-03-29 | 2012-12-26 | 南昌弘益科技有限公司 | Production method of 1'-acetoxyl chavicol acetic ester |
| CN104045553A (en) * | 2014-06-30 | 2014-09-17 | 苏州派腾生物医药科技有限公司 | Method for extracting 1'-acetoxychavicol acetate from Actinostemma tenerum Griff |
| CN104058963A (en) * | 2014-06-30 | 2014-09-24 | 苏州派腾生物医药科技有限公司 | Method for extracting 1'-acetoxychavicol acetate from alpinia chinensis |
| CN104058963B (en) * | 2014-06-30 | 2016-05-11 | 苏州派腾生物医药科技有限公司 | A kind of method of extracting ACA from the ginger of the Huashan |
| CN104045553B (en) * | 2014-06-30 | 2016-05-11 | 苏州派腾生物医药科技有限公司 | A kind of method of extracting ACA from Lobed Actinostemma Herb |
| WO2022244691A1 (en) * | 2021-05-21 | 2022-11-24 | サントリーホールディングス株式会社 | Method for producing galangal extract containing 1'-acetoxychavicol acetate |
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