CN101973937B - Double extracting process of ricinine idiotoxin - Google Patents
Double extracting process of ricinine idiotoxin Download PDFInfo
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- CN101973937B CN101973937B CN201010512828A CN201010512828A CN101973937B CN 101973937 B CN101973937 B CN 101973937B CN 201010512828 A CN201010512828 A CN 201010512828A CN 201010512828 A CN201010512828 A CN 201010512828A CN 101973937 B CN101973937 B CN 101973937B
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Abstract
The invention relates to a castor detoxification method, which is a double extracting process of ricinine idiotoxin. The method is characterized by comprising the following steps of: soaking castor bean meal in water or a mixed solution of water and ethanol to obtain the mixed solution of ricinine and idiotoxin; then condensing the mixed solution, and adding ethanol to ensure that the concentration of ethanol in the solution reaches 90% above; placing precipitate and collecting ricinine in the filtrate; collecting idiotoxin in the precipitate and separating the filtrate from the precipitate to obtain ricinine and idiotoxin simultaneously. The beneficial effect of the invention is that under effect of high concentration ethanol solvent, separation of ricinine and idiotoxin is realized and effect of extracting ricinine and idiotoxin simultaneously is realized by accident, the operation is simple and the cost is low, in particular the production efficiency is improved by the ultrasonic extraction technology, thereby providing conditions for large scale industrial production for extraction of castor meal toxins and utilization of castor meal protein.
Description
Technical field
The present invention relates to a kind of Ricin process for extracting, the two technologies of putting forward of promptly a kind of ricinine allergen.
Background technology
Castor-oil plant is Euphorbiaceae Ricinus plant, and the Viscotrol C content of its seed is up to 45%.Viscotrol C is an important chemical material, is widely used in departments such as chemical industry, weaving, light industry, medicine, mainly produces senior lubricant, paint, coating, soap, printing ink, dyeing auxiliaries, softening agent, emulsifying agent etc.In addition, castor seeds also contains rich in protein, and wherein crude protein content reaches 33%-35%, is 3 times of food crop.The above-mentioned albumen in castor seeds oil expression back is present in the castor-oil plant dregs of rice, and castor-oil plant dregs of rice crude protein content is up to 46%.Contain sphaeroprotein 60% in the ricin, gluten 20%, white protein 16% does not contain or contains the prolamine that a small amount of animal is difficult to absorb, and the overwhelming majority all can be digested and absorbed by animal, is valuable livestock and poultry protein feed resources.
, in the castor-oil plant dregs of rice, contain a large amount of toxin, limited the development and use of ricin matter.Ricin comprises toxalbumin, lectin, ricinine and allergen.Toxalbumin and lectin in the hot moulding process pyrolysis totally, but ricinine and allergen are still stayed in the castor-oil plant dregs of rice.Ricinine (Ricinine) adjoins the ketone of muttering for N-methyl-3-cyanic acid-4-methoxyl group-2-, accounts for the heavy 0.15%-0.2% of seed, in the degreasing grouts, accounts for 0.3%-0.4%, and excessive vomiting, respiration inhibition, liver and the kidney that can cause animal taken is impaired etc.Allergen (Anatoxin) accounts for the heavy 0.4%--0.5% of seed, irritated activity of tool intensive and antigenicity.Therefore, can not directly be used for mixed feed without the castor-oil plant dregs of rice of detoxification, have to be used for the farmland by as fertilizer sources, added value is very low, and is very unfortunate.
Big quantity research proves that Ricin is an objectionable impurities, also is useful matter, particularly in the development of anticarcinogen and biological pesticide, has important effect.Therefore, no matter be that the extraction of Ricin all has great importance for the utilization of ricin or the utilization of Ricin itself.
Recent decades, domestic and international many experts are devoted to the research of castor-oil plant dregs of rice detoxification technology, successively invent multiple poison-removing method.Spray swollen quick-fried detoxicity method, extruding puffing detoxicity method, biological chemistry detoxifying agent detoxicity method, microbial fermentation detoxicity method etc. like heat.Particularly under the situation that hot moulding technology is relatively popularized, become the emphasis of paying close attention in the industry for ricinine and allergenic extraction., existing achievement in research can only be extracted ricinine or allergen respectively, thereby cost is higher, and suitable for mass production does not still rest on laboratory stage so far.
Summary of the invention
The purpose of this invention is to provide the castor-oil plant dregs of rice detoxification process that a kind of technology is simple, with low cost, be suitable for scale operation.
Above-mentioned purpose is realized by following technical scheme: provide that a kind of ricinine allergen is two puies forward technology, be characterized in: the castor-oil plant dregs of rice are dipped in the mixed solvent of water or second alcohol and water, obtain ricinine and allergenic mixed solution; Again above-mentioned mixed solution is concentrated, add ethanol and the alcohol concn in the solution is reached more than 90%, place deposition; Ricinine combines in the solution; Allergen combines in the throw out, and solution is separated with throw out, can obtain ricinine, allergen simultaneously.
If the oleaginousness of the said castor-oil plant dregs of rice exceeds standard, can with sherwood oil or ether residual oil in the castor-oil plant dregs of rice of hot pressed oil be removed earlier.
The solvent of the said castor-oil plant dregs of rice is water and ethanol, ethanol and water volume ratio=and 1: 1; Optimum extraction temperature: 60 ℃; Optimum extraction total time: 120-240 minute; Optimum extraction number of times: 4 times; Optimum solvent ratio: 1.0: 6.0.
The solvent of the said castor-oil plant dregs of rice is a water, extracts 60 ℃ of temperature; Extract each time 2-3 hour 4 times.
Said placement deposition needs 20-24h, the post precipitation spinning, and throw out washed repeatedly with ethanol and precipitate twice, get the filtrating and the throw out that contain ricinine respectively.
The purification of ricinine: contain ricinine filtrating with above-mentioned, be concentrated under 50 ℃ of constant temperature with Rotary Evaporators thick, with trichloromethane refluxing extraction 0.5 hour under agitation; Repeat 2 times, merging filtrate steams trichloromethane and under 30 ℃ of vacuum, is concentrated into dried; Used methanol extraction again 0.5 hour; Repeat 2 times, activated carbon decolorizing steams methyl alcohol.With acetonitrile refluxing extraction 0.5 hour under agitation, repeat 2 times, merging filtrate, will filtrate with Rotary Evaporators be concentrated under 30 ℃ of constant temperature do after, all dissolve with ethanol, room temperature is placed, ethanol evaporation gets pure ricinine white needle-like crystals.
Allergenic purification: with the allergen deposition that obtains, use 25% dissolve with ethanol, add 10% monobasic lead acetate and stirred 0.5 hour, centrifugal, inclining supernatant, centrifugal with stirring 20 minutes behind the 10% sodium carbonate solution accent pH9.5, removes deposition.Use hydrochloric acid to dissolve to modulate pH night to be 6.0-6.5, under 50 ℃, be decompressed to finite concentration with Rotary Evaporators then, 95% ethanol sedimentation is used in ultrafiltration, and is centrifugal, and deposition is used 25% dissolve with ethanol again, and clear liquid steams ethanol and promptly gets micro white powder castor-oil plant allergen.
In said leaching process, solvent is carried out HF oscillation.
Described HF oscillation is ultra-sonic oscillation, is in the leaching process of water and alcohol mixed solution at solvent, ultra-sonic oscillation 180002-5000HZ, 25-30 minute; Extract twice.
Described HF oscillation is ultra-sonic oscillation, is being in the leaching process of solvent with water, and ultra-sonic oscillation 20000-25000HZ 28-35 minute, extracts twice.
The invention has the beneficial effects as follows: under the effect of high concentration ethanol solvent; Realized that ricinine separates with allergenic; Obtained the windfall effect that extracts two kinds of Ricins simultaneously; And have characteristics such as simple to operate, with low cost,, thereby have higher use value and good market outlook for the extraction of castor-oil plant dregs of rice toxin and the utilization of castor-oil plant cake protein provide the condition of large-scale industrial production.
Description of drawings
Fig. 1 is the ricinine allergen extraction process schema of first kind of embodiment;
Fig. 2 is the ricinine purifying technique schema of first kind of embodiment;
Fig. 3 is the allergen purifying technique schema of first kind of embodiment;
Fig. 4 is the technological process of production figure of second kind of embodiment;
Fig. 5 is the technological process of production figure of the third embodiment;
Fig. 6 is the technological process of production figure of the 4th kind of embodiment;
Fig. 7 is the ricinine uv atlas;
Fig. 8 is the infrared spectrum of ricinine;
The mass spectrum of Fig. 9 ricinine;
Figure 10 is the structural formula of ricinine;
Figure 11 is allergenic uv atlas;
Figure 12 is allergenic infrared spectrum.
Embodiment
One, description of test
In order to inquire into the method for castor-oil plant detoxification, done a large amount of experiments with regard to indexs such as different solvents, temperature, times, obtain to draw a conclusion:
1. when using ethanol as solvent, ethanol can only extract ricinine, and can not extract allergen.
2. when water is solvent, extract 60 ℃ of temperature; One time extraction time 2-3 hour, to extract four times, ricinine and allergenic yield are higher.
3. when using the second alcohol and water as solvent, the extraction yield of ricinine was high when ethanol content was 70-50%, and allergenic extraction yield was high when ethanol content was 20-10%, had only ethanol content at 50% o'clock, just can reach ricinine and the allergen good effect of extraction yield simultaneously.
4. it is little to allergenic extraction yield influence to extract temperature, but big slightly to the influence of ricinine, raises with temperature, and the extraction yield of ricinine improves gradually, reach 60 ℃ after, extraction yield reduces gradually, explains that optimum temps should select 60 ℃.
5. be in the leaching process of solvent adopting water or second alcohol and water, apply HF oscillation such as UW and can significantly improve efficient, shorten working hours significantly.
6. when using the second alcohol and water as solvent, there is very big influence extraction time to ricinine and allergenic extraction yield.Increase extraction yield in time increases gradually, and extraction yield reduced gradually after ultrasonic time reached 25-30 minute, explain that extraction time is unsuitable long when filtration does not renew solvent, otherwise ricinine has sex change.
7. when water is solvent, extract twice, use supersound extraction 28-35 minute at every turn, ricinine and allergenic yield are higher.
8. ethanol: water=1: 1, extracting temperature is 60 ℃, extracts total time 2-4 hour, divides four extraction ricinines and allergen yield higher.
9. ethanol: water=1: 1, extracting temperature is 60 ℃, extracts twice, each sonic oscillation 25-30 minute, ricinine and allergen yield were higher.
10. raw material and solvent ratio are to the influence of ricinine and allergen extraction yield: in ethanol: the ratio of water=1: 1 adds in the extractor, and raw material and solvent ratio are better at 1: 6 o'clock extraction yield, can satisfy the high requirement of ricinine and allergen while extraction yield.
11. with water is that solvent adds in the supersound extraction device, raw material and solvent ratio are better at 1.0: 8.0 o'clock extraction yields, can satisfy the high requirement of extraction yield simultaneously of ricinine and allergen.
Based on above-mentioned experiment conclusion, total design below the formation: high concentration ethanol can dissolve ricinine, and the indissoluble allergen; Therefore; Castor-oil plant dregs of rice leachable is carried out high concentration ethanol handle, can impel ricinine to combine in the solution, allergen combines in the deposition; Can obtain ricinine and two kinds of Ricins of allergen simultaneously through separating, and then accomplish the detoxification operation of the castor-oil plant dregs of rice.
Two, embodiment
First kind of embodiment: adopting the second alcohol and water is solvent, and the castor-oil plant dregs of rice are carried out detoxification treatment.Its technical process is as shown in Figure 1.Below in conjunction with Fig. 1 this technology is further described:
1. bullion extracts: the castor-oil plant dregs of rice are pulverized the extractor of packing into, if the hot moulding castor-oil plant dregs of rice are then removed oil residual in the castor-oil plant dregs of rice with sherwood oil or ether earlier.Added the second alcohol and water then in by volume 1: 1, the adjustment castor-oil plant dregs of rice and solvent ratio are 1: 6, extract 60 ℃ of temperature, through four circulation extraction; Accomplished in 120-240 minute, ricinine that obtains and allergenic mixed solution concentrate the back to mixed solution again and add ethanol, and the concentration of ethanol in solution is reached more than 90%; Place 20-24h, promptly produce deposition, ricinine is dissolved in the supernatant; Allergen is in throw out, and filtrating and throw out are collected in spinning respectively; Wash the deposition secondary repeatedly with ethanol, and collect filtrating and throw out respectively, promptly get ricinine, allergen bullion.
2. the purification of ricinine: as shown in Figure 2, the above-mentioned ricinine that contains is filtrated, under 50 ℃ of constant temperature, be concentrated into thick with Rotary Evaporators; With trichloromethane refluxing extraction 0.5 hour under agitation, repeat merging filtrate 2 times; Steam trichloromethane and under 30 ℃ of vacuum, be concentrated into driedly, used methanol extraction again 0.5 hour, repeat 2 times; Activated carbon decolorizing steams methyl alcohol.With acetonitrile refluxing extraction 0.5 hour under agitation, repeat 2 times, merging filtrate, will filtrate with Rotary Evaporators be concentrated under 30 ℃ of constant temperature do after, all dissolve with ethanol, room temperature is placed, ethanol evaporation gets pure ricinine white needle-like crystals.It is identical with the spectrogram that document provides that pure ricinine is made the spectrogram that ir spectra and mass spectroscopy obtain.
3. allergenic purification: as shown in Figure 3, with the allergen deposition that obtains, use 25% dissolve with ethanol, add 10% monobasic lead acetate and stirred 0.5 hour, centrifugal, inclining supernatant, centrifugal with stirring 20 minutes behind the 10% sodium carbonate solution accent pH9.5, removes deposition.Use hydrochloric acid to dissolve to modulate pH night to be 6.0-6.5, under 50 ℃, be decompressed to finite concentration with Rotary Evaporators then, 95% ethanol sedimentation is used in ultrafiltration, and is centrifugal, and deposition is used 25% dissolve with ethanol again, and clear liquid steams ethanol and promptly gets white powder castor-oil plant allergen.
For the hot moulding castor-oil plant dregs of rice, the gained castor-oil plant dregs of rice are exactly the detoxification product after extracting ricinine and allergen, can be as the protein raw materials of feed.
Second kind of embodiment: as shown in Figure 4; Also be to be solvent with the second alcohol and water, its technical process and first kind of embodiment are basic identical, just when the second alcohol and water is solvent extraction; Solution has been carried out HF oscillation; This example recommends to adopt ultra-sonic oscillation, is about to the castor-oil plant dregs of rice and pulverizes the supersound extraction jar of packing into, if the hot moulding castor-oil plant dregs of rice are then removed oil residual in the castor-oil plant dregs of rice with sherwood oil or ether earlier.Added the second alcohol and water then in by volume 1: 1; Adjustment the castor-oil plant dregs of rice and solvent ratio are 1: 6, and 60 ℃ of extraction temperature are under the 20000-25000HZ sonic oscillation 25-30 minute the time; Filter; Add novel solvent in the filter residue, repeat to extract completion in twice total time 50-60 minute, obtain ricinine and allergenic mixed solution.Again mixed solution is carried out adding ethanol behind the concentrating under reduced pressure, and the concentration of ethanol in solution is reached more than 90%, place 20-24h; Promptly produce deposition, ricinine is dissolved in the filtrating, and allergen is a throw out; Filtrating and throw out are collected in spinning respectively, wash the deposition secondary repeatedly with ethanol; And collect filtrating and throw out respectively, promptly get ricinine, allergen bullion.Its purification process is identical with first kind of embodiment.
The third embodiment: adopting water is the solvent of the castor-oil plant dregs of rice, and technical process is as shown in Figure 5.Castor-oil plant dregs of rice water soaked 2-3 hour down at 60 ℃, added novel solvent in the filter residue, repeated to extract completion in 3 times total time 6-10 hour, and ricinine and allergen yield are higher.Soak repeatedly and extract, collect and extrude liquid, become ricinine and the allergenic mixture of castor-oil plant through evaporation concentration.In mixture, add ethanol, and alcohol concn transferred to more than 90% handle, precipitate and separate can occur, ricinine is in supernatant, and allergen is in throw out.Through spinning, can obtain ricinine and allergenic bullion respectively again, get final product through purifying again two kinds of pure article.Extrude dry-matter and be nontoxic castor-oil plant dregs of rice product.
The 4th kind of embodiment: water is the additional ultrasonication of solvent, and its technical process is as shown in Figure 6, and the castor-oil plant dregs of rice are pulverized the supersound extraction jar of packing into, if the hot moulding castor-oil plant dregs of rice are then removed oil residual in the castor-oil plant dregs of rice with sherwood oil or ether earlier.Add entry then, the adjustment castor-oil plant dregs of rice and solvent ratio are 1: 8, extract 60 ℃ of temperature, extract through 2 circulating ultrasonics, each 28-35 minute, accomplish ricinine that obtains and allergenic mixed solution in total 56-70 minute.Again mixed solution is carried out adding ethanol behind the concentrating under reduced pressure, and the concentration of ethanol in solution is reached more than 90%, place 20-24h; Promptly produce deposition, ricinine is dissolved in the filtrating, and allergen is a throw out; Filtrating and throw out are collected in spinning respectively, wash the deposition secondary repeatedly with ethanol; And collect filtrating and throw out respectively, promptly get ricinine, allergen bullion.Its purification process is identical with first kind of embodiment.
Three. the structure elucidation of ricinine
1. using UVS, is between the 200-600nm at wavelength, and the castor-oil plant allergen is scanned, and sees that the allergenic uv atlas of Fig. 7 castor-oil plant shows a peak, explains to have obtained purer allergen.
2. the drafting of infrared spectrum: get the pure article of ricinine a little, fully grind mixing with KBr, compressing tablet is measured infrared spectrogram, the infrared spectrum of ricinine is seen Fig. 8.
From Fig. 8, can see 3042cm
-1The absorption peak that possibly cause for the unsaturated carbon C-H stretching vibration on the unsaturated ring.2226cm
-1For typically-absorption peak that the stretching vibration of CN triple bond causes.Since the unsaturated link(age) conjugation makes with encircling upward-the C-O stretching vibration is to the displacement of lower wave number direction, and the result appears at 1653cm
-1The absorption peak that causes for the stretching vibration of C=O.1492cm
-1Can be summed up as the absorption peak that the C-C stretching vibration causes on the monocycle.1355cm
-1For-CH stretching vibration absorption peak, 1135cm
-1Be the absorption peak that the C-O stretching vibration causes, 947cm
-1Be summed up as-C-H rocking vibration 776,687cm
-1Can be summed up as the absorption peak that the formation vibration of unsaturated substitution in ring base causes.From its result of spectrum analysis, meet ricinine structure shown in Figure 6 basically, thereby confirm that the crystal that draws is a ricinine.
3. the drafting of the mass spectrum of ricinine:
From the mass-to-charge ratio (z/m) at the visible climax of Fig. 9 is 164.85, should be the mass-to-charge ratio of ricinine positive ion, and the ricinine molecular formula is C
8H
8N
2O
2, its structure such as Figure 10, molar mass is 163.85g/mol.
4. the allergenic UV spectrum of castor-oil plant
Using UVS, is between the 200-600nm at wavelength, and the castor-oil plant allergen is scanned, and sees that the allergenic uv atlas of Figure 11 castor-oil plant shows a peak, explains to have obtained purer allergen.
5. the analysis of the allergenic ir spectra of castor-oil plant:
Get the pure article of castor-oil plant allergen a little, fully grind mixing with KBr, compressing tablet is measured infrared spectrogram, the infrared spectrum of ricinine is seen Figure 12, allergenic infrared spectrum has shown the charateristic avsorption band that document is introduced, and explains to have obtained purer allergen.
From Figure 12, can see 3406.9cm
-1The absorption peak that possibly cause for the N-HC-H stretching vibration of CONH.2959.0 and 2930.0cm
-1The peak at place is CH
3And CH
2The absorption peak that stretching vibration causes.Appear at 1653cm
-1The absorption peak that causes for the stretching vibration of C=O.1080.2cm
-1For-absorption peak that the O--stretching vibration causes, its result also explains from spectrum analysis, what obtain is purer castor-oil plant allergenic prod.
Five. the technical indicator of product
1. the technical indicator of the castor-oil plant dregs of rice:
Table 1 detoxification castor-oil plant dregs of rice technical indicator
These parameters explanation: realized the thorough detoxification of the castor-oil plant dregs of rice with this kind method, and can protect at utmost that useful composition is without prejudice in the castor-oil plant dregs of rice.The detoxification castor-oil plant dregs of rice can be done protein feed sale efficiently, and quality product has reached the standard of national requirements.Ricinine, the allergen that extracts can be made biological pesticide and use.
Claims (9)
1. a ricinine allergen is two puies forward technology, it is characterized in that: the castor-oil plant dregs of rice are dipped in the mixed solvent of water or 1: 1 second alcohol and water of volume ratio, obtain ricinine and allergenic mixed solution; Again above-mentioned mixed solution is concentrated, add ethanol and the alcohol concn in the solution is reached more than 90%, place deposition; Ricinine combines in the solution; Allergen combines in the throw out, and solution is separated with throw out, promptly obtains two kinds of materials of ricinine and allergen simultaneously.
2. ricinine allergen according to claim 1 is two puies forward technology, it is characterized in that: the said castor-oil plant dregs of rice and solvent ratio 1: 6; Extract 60 ℃ of temperature; Extraction time 4 times; Total extraction time 120-240 minute.
3. ricinine allergen according to claim 1 is two puies forward technology, and it is characterized in that: the solvent of the said castor-oil plant dregs of rice is a water, extracts 60 ℃ of temperature; Extraction time 4 times; Each extraction time 2-3 hour, the castor-oil plant dregs of rice and solvent ratio 1: 8.
4. the two technologies of carrying of ricinine allergen according to claim 1; It is characterized in that: said placement deposition needs 20-24h; The post precipitation spinning, and throw out washed repeatedly with ethanol and precipitate twice, the filtrating and the throw out that contain ricinine got respectively.
5. ricinine allergen according to claim 1 is two puies forward technology, and it is characterized in that: said ricinine is purified by following method: ricinine filtrate be concentrated under 50 ℃ of constant temperature with Rotary Evaporators thick, with trichloromethane refluxing extraction 0.5 hour under agitation; Repeat 2 times, merging filtrate steams trichloromethane and under 30 ℃ of vacuum, is concentrated into dried; Use methanol extraction again 0.5 hour, and repeated activated carbon decolorizing 2 times; Steam methyl alcohol,, repeat 2 times with acetonitrile refluxing extraction 0.5 hour under agitation; Merging filtrate, will filtrate with Rotary Evaporators be concentrated under 30 ℃ of constant temperature do after, all dissolve with ethanol; Room temperature is placed, and ethanol evaporation gets pure ricinine white needle-like crystals.
6. ricinine allergen according to claim 1 is two puies forward technology, and it is characterized in that: said allergen is purified by following method: the allergen deposition is used 25% dissolve with ethanol, add 10% monobasic lead acetate and stirred 0.5 hour; Centrifugal, inclining supernatant, with stirring 20 minutes behind the 10% sodium carbonate solution accent pH9.5; Centrifugal, remove deposition, use hydrochloric acid that solution is modulated pH and be 6.0-6.5; Under 50 ℃, be decompressed to finite concentration with Rotary Evaporators then, 95% ethanol sedimentation is used in ultrafiltration; Centrifugal, deposition is used 25% dissolve with ethanol again, clear liquid steams ethanol and promptly gets micro white powder castor-oil plant allergen.
7. ricinine allergen according to claim 1 is two puies forward technology, it is characterized in that: in said leaching process, solvent is carried out HF oscillation.
8. ricinine allergen according to claim 7 is two puies forward technology, and it is characterized in that: described HF oscillation is ultra-sonic oscillation, and the second alcohol and water is in the leaching process of solvent, extracts twice, each ultra-sonic oscillation 25-30 minute.
9. ricinine allergen according to claim 7 is two puies forward technology, and it is characterized in that: described HF oscillation is ultra-sonic oscillation, is being in the leaching process of solvent with water, extracts twice, each ultra-sonic oscillation 28-35 minute.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1060764A (en) * | 1991-10-08 | 1992-05-06 | 太原机械学院 | Method for extracting toxin from process water for preparing nontoxic protein by separating castor cake |
| CN101129365A (en) * | 2007-09-12 | 2008-02-27 | 首都医科大学 | Analgesics use of ricinine |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1060764A (en) * | 1991-10-08 | 1992-05-06 | 太原机械学院 | Method for extracting toxin from process water for preparing nontoxic protein by separating castor cake |
| CN101129365A (en) * | 2007-09-12 | 2008-02-27 | 首都医科大学 | Analgesics use of ricinine |
Non-Patent Citations (1)
| Title |
|---|
| 梁新宇 等.蓖麻毒素的分离提取.《粮食与油脂》.1999,(第4期),第22－23页. * |
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