CN101768200B - Process for preparing 3-epibetulinic acid by extracting from rhizoma nelumbinis and charred rhizoma nelumbinis - Google Patents
Process for preparing 3-epibetulinic acid by extracting from rhizoma nelumbinis and charred rhizoma nelumbinis Download PDFInfo
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- CN101768200B CN101768200B CN2009102565710A CN200910256571A CN101768200B CN 101768200 B CN101768200 B CN 101768200B CN 2009102565710 A CN2009102565710 A CN 2009102565710A CN 200910256571 A CN200910256571 A CN 200910256571A CN 101768200 B CN101768200 B CN 101768200B
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Abstract
The invention relates to a process for preparing 3-epibetulinic acid by extracting from rhizoma nelumbinis and charred rhizoma nelumbinis, comprising the following steps of: reflowing and extracting rhizoma nelumbinis and charred rhizoma nelumbinis with petroleum ether; extracting the rhizoma nelumbinis and charred rhizoma nelumbinis with 85-100 percent ethanol; stirring silica gel into an ethanol extract and drying; then heating and extracting the dried mixture with ethyl acetate; re-crystallizing ethyl acetate; or extracting the rhizoma nelumbinis and the charred rhizoma nelumbinis with 85-100 percent ethanol; stirring the silica gel into the ethanol extract and drying; extracting with the petroleum ether; then heating and extracting with the ethyl acetate; and re-crystallizing the ethyl acetate. The process for preparing the 3-epibetulinic acid has the extraction rate up to 28 percent which is improved by 120 times as comparison with the prior art and the purity more than 98 percent which is similar to the prior art. The technology is not subjected to column chromatography, so that the process is relatively simple as comparison with the prior art; and the toxicity of used solvent is lower, while the toxicity of solvent used in the prior art is higher.
Description
Technical field:
The present invention relates to a kind of preparation technology of compound, particularly a kind of technology of from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extracting preparation 3-epi-Betulinic acid.
Background technology:
Rhizoma nelumbinis is the dry root stipes portion of nymphaeaceae plant lotus (Nelumbo Nucifera Gaertn.), is the traditional Chinese medicine of China, has hemostasis, and the effect of the stasis of blood that disappears is used for the treatment of haematemesis, spitting of blood, hematuria, bleeding from five sense organs or subcutaneous tissue, uterine bleeding.Record in going through version " one one of Chinese pharmacopoeia.Charred Nodus Nelumbinis Rhizomatis is that the rhizoma nelumbinis process of preparing Chinese medicine processes.Contain chemical ingredientss such as tannin and l-asparagine in the rhizoma nelumbinis, contain triterpene substance 3-epi-Betulinic acid (3-epibutulinic acid) simultaneously, structure is as follows:
Bibliographical information its preparation method: after the rhizoma nelumbinis pulverizing, use extraction using alcohol, reclaim ethanol, mix diatomite and silica gel in medicinal extract, dry, grind, put in the apparatus,Soxhlet's, with sherwood oil, benzene, ether, chloroform and ethyl acetate extraction, benzene extraction is partly added benzene make sample liquid respectively, carry out silica gel column chromatography, carry out wash-out with chloroform-acetone (6.5: 1), benzene-acetone (5: 1) respectively, the ethyl acetate recrystallization gets white crystal (brilliant I) and light yellow crystal (brilliant II), and white crystal (brilliant I) is the 3-epi-Betulinic acid.This kind method must be measured lower (the 15kg rhizoma nelumbinis obtains the 107mg3-epi-Betulinic acid), and through column chromatography, technology is loaded down with trivial details, and solvent for use benzene, chloroform toxicity are bigger.
Summary of the invention
The purpose of this invention is to provide a kind of technology of extracting preparation 3-epi-Betulinic acid from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, this kind process yield, purity are higher, and technology is simple, and solvent for use toxicity is less.
The technical scheme that the present invention takes is:
From rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extract the technology of preparation 3-epi-Betulinic acid, comprise the steps:
(1) gets rhizoma nelumbinis or charred Nodus Nelumbinis Rhizomatis and use earlier the sherwood oil refluxing extraction, to extract after residue volatilization removes sherwood oil, with 85%-100% (v/v) ethanol 40-100 ℃ extracts down again, perhaps gets rhizoma nelumbinis or charred Nodus Nelumbinis Rhizomatis and directly extracts down with ethanol 40-100 ℃ of 85%-100% (v/v);
(2) merge ethanol extract behind the extraction using alcohol, reclaim ethanol, obtain ethanol extraction medicinal extract;
(3) the ethanol extraction medicinal extract that obtains is admixed silica gel, mix drying after, with ethyl acetate 40-100 ℃ down heating extract, perhaps use earlier the sherwood oil refluxing extraction, again with ethyl acetate 40-100 ℃ of heating extraction down;
(4) ethyl acetate in the recovery said extracted liquid will be separated out solid filtering and go out, and use the re-crystallizing in ethyl acetate purifying, get compound 3-epi-Betulinic acid.
The described sherwood oil refluxing extraction of above-mentioned steps (1) is 1-3 time, each 0.5-3h, and the amount that adds sherwood oil altogether is rhizoma nelumbinis or charred Nodus Nelumbinis Rhizomatis 4-20 a times.
Described rhizoma nelumbinis of step (1) or charred Nodus Nelumbinis Rhizomatis are pulverized particles or medicine materical crude slice.
The described extraction using alcohol of above-mentioned steps (1) 1-4 time extracts 1-3h at every turn, and the amount of alcohol that adds 85%-100% altogether is rhizoma nelumbinis or charred Nodus Nelumbinis Rhizomatis quality 4-20 a times.
The preferred 95%-100% of the described ethanol of step (1).
The described silica gel consumption of above-mentioned steps (3) is 1-5 a times of ethanol extraction medicinal extract quality, and described ethyl acetate heating is extracted 1-3 time, and the consumption that amounts to ethyl acetate is admixed 2-18 times of silica gel after drying amount for ethanol extraction medicinal extract.
The described sherwood oil refluxing extraction of above-mentioned steps (3) is 1-3 time, each 0.5-3h, and the amount that adds sherwood oil is altogether admixed 4-20 times of silica gel after drying amount for ethanol extraction medicinal extract.
The described re-crystallizing in ethyl acetate of above-mentioned steps (4) 1-5 time.
The present invention prepares the technology extraction rate reached 28% of 3-epi-Betulinic acid, improve 120 times than prior art, purity is greater than 98%, and directly use silica gel and ethyl acetate, without column chromatography, technology is simple, solvent for use toxicity is less, prior art solvent for use toxicity is bigger, and loaded down with trivial details through column chromatography technology, and yield is lower.
Description of drawings
Fig. 1 makes the mass spectrum of compound for the present invention;
Fig. 2 makes the hydrogen nuclear magnetic resonance spectrogram (a) of compound for the present invention;
Fig. 3 makes the hydrogen nuclear magnetic resonance spectrogram (b) of compound for the present invention;
Fig. 4 makes the hydrogen nuclear magnetic resonance spectrogram (c) of compound for the present invention;
Fig. 5 makes the hydrogen nuclear magnetic resonance spectrogram (d) of compound for the present invention;
Fig. 6 makes the carbon-13 nmr spectra figure (a) of compound for the present invention;
Fig. 7 makes the carbon-13 nmr spectra figure (b) of compound for the present invention;
Fig. 8 makes the purity check figure of compound for the present invention.
Embodiment
From charred Nodus Nelumbinis Rhizomatis, extract the technology of preparation 3-epi-Betulinic acid:
Get the 15kg charred Nodus Nelumbinis Rhizomatis, be ground into particle, with the sherwood oil of 12 times of its quality, refluxing extraction 3 times, each 1h.To extract after residue volatilization removes sherwood oil, extract 4 times for 70 ℃, extract 3h at every turn, add 95% amount of alcohol altogether and be 16 times of charred Nodus Nelumbinis Rhizomatis quality, merge ethanol extract, reclaim ethanol, obtain ethanol extraction medicinal extract with 95% ethanol.Admix the silica gel of 2.5 times of ethanol extraction medicinal extract quality, mix drying after, with 60 ℃ of heating and refluxing extraction of ethyl acetate 2 times, the amount that adds ethyl acetate is altogether admixed 10 times of silica dehydrator amount for its medicinal extract.Reclaim the ethyl acetate in the said extracted liquid, will separate out solid filtering and go out,, get compound 3-epi-Betulinic acid 18g with 4 purifying of re-crystallizing in ethyl acetate, extraction rate reached 28.57%, purity is greater than 98%.The compound 3-epi-Betulinic acid that obtains, the Molish reaction negative, the L-B reaction is positive.ESI-MS[M-H]
+455.6。
1HNMR composes (600MHz, DMSO-d
6): 4.688 (1H, d, J=1.2Hz) and 4.559 (1H br.s) is 29 two olefinic proton signals; 4.278 (1H br.s) is 3-β-H signal; 2.964 (2H m) is 13-H and 18-H signal; 2.217 (1H ddd) is 22-α-H signal; 1.787 (3H s) is 30-CH
3Signal; All the other 5 methyl signals all are unimodal and appear at 0.929,0.868,0.864,0.760,0.647.
13CNMR (150MHz, DMSO-d
6) signal such as following table.
Table 1 carbon-13 nmr spectra data (ppm)
Gained compound mass spectrum such as accompanying drawing 1, nuclear magnetic resonance spectrum such as accompanying drawing 2-7.
Purity check result (as accompanying drawing 8) sees Table 2:
Table 2 chromatographic peak result
| Name | Retention time | Area | Peak height | Content | Unit | The % |
|
| 1 | Peak 1 | 16.136 | 12421519 | 458433 | 98.57 | ||
| 2 | Peak 2 | 17.908 | 158452 | 6080 | 1.26 | ||
| 3 | Peak 3 | 20.347 | 21494 | 890 | 0.17 |
From rhizoma nelumbinis, extract the technology of preparation 3-epi-Betulinic acid:
Get the 15kg rhizoma nelumbinis, be ground into particle, with the sherwood oil of 12 times of its quality, refluxing extraction 3 times, each 1h.To extract after residue volatilization removes sherwood oil, extract 4 times for 70 ℃, extract 3h at every turn, add 95% amount of alcohol altogether and be 16 times of rhizoma nelumbinis quality, merge ethanol extract, reclaim ethanol, obtain ethanol extraction medicinal extract with 95% ethanol.Admix the silica gel of 2.5 times of ethanol extraction medicinal extract quality, mix drying after, with 60 ℃ of heating and refluxing extraction of ethyl acetate 2 times, the amount that adds ethyl acetate is altogether admixed 10 times of silica dehydrator amount for its medicinal extract.Reclaim the ethyl acetate in the said extracted liquid, will separate out solid filtering and go out,, get compound 3-epi-Betulinic acid 16.82g with 4 purifying of re-crystallizing in ethyl acetate, extraction rate reached 28.23%, purity is greater than 98%.
From charred Nodus Nelumbinis Rhizomatis, extract the technology of preparation 3-epi-Betulinic acid:
Get the 15kg charred Nodus Nelumbinis Rhizomatis, be ground into particle, extract 4 times, extract 3h at every turn, add 95% amount of alcohol altogether and be 16 times of charred Nodus Nelumbinis Rhizomatis quality, merge ethanol extract, reclaim ethanol, obtain ethanol extraction medicinal extract with 80 ℃ of 95% ethanol.Admix the silica gel of 2.5 times of ethanol extraction medicinal extract quality, mix drying after, with sherwood oil refluxing extraction 3 times, the amount that adds sherwood oil is altogether admixed 12 times of silica dehydrator amount for its medicinal extract.With 60 ℃ of heating and refluxing extraction of ethyl acetate 2 times, the amount that adds ethyl acetate is altogether admixed 10 times of silica dehydrator amount for its medicinal extract again.Reclaim the ethyl acetate in the said extracted liquid, will separate out solid filtering and go out,, get compound 3-epi-Betulinic acid 17.62g with 4 purifying of re-crystallizing in ethyl acetate, extraction rate reached 28.3%, purity is greater than 98%.
Embodiment 4
From rhizoma nelumbinis, extract the technology of preparation 3-epi-Betulinic acid:
Get the 15kg rhizoma nelumbinis, be ground into particle, extract 4 times, extract 3h at every turn, add 95% amount of alcohol altogether and be 16 times of rhizoma nelumbinis quality, merge ethanol extract, reclaim ethanol, obtain ethanol extraction medicinal extract with 80 ℃ of 95% ethanol.Admix the silica gel of 2.5 times of ethanol extraction medicinal extract quality, mix drying after, with sherwood oil refluxing extraction 3 times, the amount that adds sherwood oil is altogether admixed 12 times of silica dehydrator amount for its medicinal extract.Extract 2 times with 60 ℃ of heating of ethyl acetate, the amount that adds ethyl acetate is altogether admixed 10 times of silica dehydrator amount for its medicinal extract again.Reclaim the ethyl acetate in the said extracted liquid, will separate out solid filtering and go out,, get compound 3-epi-Betulinic acid 17.0g with 4 purifying of re-crystallizing in ethyl acetate, extraction rate reached 28.5%, purity is greater than 98%.
Claims (8)
1. from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extract the technology of preparation 3-epi-Betulinic acid, it is characterized in that comprising the steps:
(1) gets rhizoma nelumbinis or charred Nodus Nelumbinis Rhizomatis and use earlier the sherwood oil refluxing extraction, to extract after residue volatilization removes sherwood oil, with volumetric concentration 85%-100% ethanol 40-100 ℃ extracts down again, perhaps gets rhizoma nelumbinis or charred Nodus Nelumbinis Rhizomatis and directly extracts down with ethanol 40-100 ℃ of volumetric concentration 85%-100%;
(2) merge ethanol extract behind the extraction using alcohol, reclaim ethanol, obtain ethanol extraction medicinal extract;
(3) the ethanol extraction medicinal extract that obtains is admixed silica gel, mix drying after, with ethyl acetate 40-100 ℃ of following heating and refluxing extraction, perhaps earlier use the sherwood oil refluxing extraction, again with ethyl acetate 40-100 ℃ of following heating and refluxing extraction;
(4) ethyl acetate in the recovery said extracted liquid will be separated out solid filtering and go out, and use the re-crystallizing in ethyl acetate purifying, get compound 3-epi-Betulinic acid.
2. according to the described technology of from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extracting preparation 3-epi-Betulinic acid of claim 1, it is characterized in that, the described sherwood oil refluxing extraction of step (1) is 1-3 time, each 0.5-3h, and the amount that adds sherwood oil altogether is rhizoma nelumbinis or charred Nodus Nelumbinis Rhizomatis quality 4-20 a times.
3. according to the described technology of from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extracting preparation 3-epi-Betulinic acid of claim 1, it is characterized in that, the described extraction using alcohol of step (1) 1-4 time extracts 1-3h at every turn, and the amount of alcohol that adds volumetric concentration 85%-100% altogether is rhizoma nelumbinis or charred Nodus Nelumbinis Rhizomatis quality 4-20 a times.
4. according to claim 1 or the 3 described technologies of from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extracting preparation 3-epi-Betulinic acid, it is characterized in that the described ethanol volumetric concentration of step (1) is 95%-100%.
5. according to the described technology of from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extracting preparation 3-epi-Betulinic acid of claim 1, it is characterized in that the described silica gel consumption of step (3) is 1-5 a times of ethanol extraction medicinal extract quality.
6. according to the described technology of from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extracting preparation 3-epi-Betulinic acid of claim 1, it is characterized in that, the described ethyl acetate heating of step (3) is extracted as 1-3 time, and the consumption that amounts to ethyl acetate is 2-18 a times that ethanol extract is admixed silica gel after drying amount.
7. according to the described technology of from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extracting preparation 3-epi-Betulinic acid of claim 1, it is characterized in that, the described sherwood oil refluxing extraction of step (3) is 1-3 time, each 0.5-3h, the amount that adds sherwood oil is altogether admixed 4-20 times of silica gel after drying amount for ethanol extraction medicinal extract.
8. according to the described technology of from rhizoma nelumbinis, charred Nodus Nelumbinis Rhizomatis, extracting preparation 3-epi-Betulinic acid of claim 1, it is characterized in that the described re-crystallizing in ethyl acetate of step (4) 1-5 time.
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|---|---|---|---|---|
| CN1279950A (en) * | 1999-03-01 | 2001-01-17 | 中国科学院成都生物研究所 | Sigma-receptor acting medicine with triterpene compound structure |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1279950A (en) * | 1999-03-01 | 2001-01-17 | 中国科学院成都生物研究所 | Sigma-receptor acting medicine with triterpene compound structure |
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| 赵贞贞.2009102565710.《STN检索记录》.2011, * |
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