CN1865232A - Method for extracting notoginseng essence from notoginseng - Google Patents
Method for extracting notoginseng essence from notoginseng Download PDFInfo
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- CN1865232A CN1865232A CN 200610027962 CN200610027962A CN1865232A CN 1865232 A CN1865232 A CN 1865232A CN 200610027962 CN200610027962 CN 200610027962 CN 200610027962 A CN200610027962 A CN 200610027962A CN 1865232 A CN1865232 A CN 1865232A
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Abstract
This invention discloses a method for extracting dencichine from Panax notoginseng, belonging to the medicine technology field, comprising: alcohol extraction, water extraction, add ethanol to the water to produce precipitant, remove the impurities by filtration, then extract the water solution with butanol, combine the water phases, remove the sugar components and phychrome by using the ion-exchange resin(e.g. D001 type ion-exchange resin) which is polymerized by phenylethene and diethyl benzene monomers, precipitate the elution with acetone, and then obtain the high-purity dencichine by recrystallization. This invention is characterized of safety and low cost, which is much qualified for industrial production.
Description
Technical field
The present invention relates to a kind of method of technical field of pharmaceuticals, specifically is a kind of method of extracting dencichine from pseudo-ginseng.
Background technology
That rare Chinese medicine " pseudo-ginseng " has is promoting blood circulation and removing blood stasis, subduing swelling and relieving pain, function such as regulate channels and activate collateral, and wherein is celebrated with hemostatic function especially.Compendium of Material Medica claims " analgesic therapy of pseudo-ginseng styptic powder blood ", and pseudo-ginseng has the good name of " stasis of blood is not stayed in hemostasis, and stagnation resolvation is not just hindered ", is the key medicine of regulating blood condition in fact.Ancient Chinese medicine doctor is top grade as hemostasis with pseudo-ginseng, is widely used in internal and external haemorrhage diseases such as wound, hemorrhage due to internal injury.The water soluble component dencichine of pseudo-ginseng is isolating a kind of special amino acid from Radix Notoginseng, and it can shorten the clotting time of mouse, and platelet counts is significantly increased, but does not also have the production and the use of dencichine preparation at present.
The extraction process bibliographical information of dencichine and existing patent all adopt alcohol extracting in the pseudo-ginseng, the residue water extraction filters, concentrates n-butanol extraction, resin chromatography on the water extract, as the Zheng Yinan of China, Li Xianggao, Shandong fork, Zheng Lu, the tall and erect husband of the little villous themeda of Japan, Chinese patent CN 1267665A, Chinese patent CN 1166679C etc.Basically identical on these report technologies particularly all adopted Sephadex LH-20 and CM Sephadex C-25 resin column in extraction process, and the equal price costliness of these two kinds of resins, cost is higher, and it is consuming time to handle sample, is unfavorable for industrial production.
Therefore to obtain hemostatic compositions dencichine in the pseudo-ginseng in order extracting, and to make technology can be used for suitability for industrialized production, the dencichine preparation is used for clinical, be necessary to improve above-mentioned traditional production technique.
Summary of the invention
The objective of the invention is to overcome the defective of prior art, a kind of method of extracting dencichine from pseudo-ginseng is provided.The present invention be a kind of have simple, be applicable to suitability for industrialized production, and the novel process of hemostasis effective constituent dencichine in the low extraction purifying pseudo-ginseng of cost, and can be used for developing agent for stanching.
The present invention is achieved by the following technical solutions:
The present invention adopts alcoholic solution to extract, flooding is handled then, water extract ethanol sedimentation, n-butanol extraction, merging the direct mistake of water is the ion exchange resin (as D001 type ion exchange resin) of monomer polymerization with vinylbenzene and divinylbenzene, the ammonia solution wash-out, acetone precipitation carries out recrystallization at last and just can obtain the higher dencichine of purity.
Specific implementation step of the present invention is as follows:
(1) be 95% ethanolic soln with pseudo-ginseng with 5-15 volume ratio doubly, the ethanolic soln of 10 times of amounts preferably, alcohol extracting 10-20h, preferably 12h; Be 95% ethanol again with 2-10 volume ratio doubly, the ethanolic soln of 5 times of amounts preferably, alcohol extracting 4-10h, best 6h, the extraction temperature is a room temperature;
(2) merge twice alcohol extract, reserve for other use.Residue is dried, add the flooding that 10-20 doubly measures, preferably 10 times, extract 10-20h, preferably 12h; The flooding of doubly measuring with 2-10 again, best 5 times, extract 4-10h, best 6h, the extraction temperature is a room temperature;
(3) filter, filtrate is concentrated into a certain amount of, and adding ethanol, to regulate determining alcohol be 50-90%, and preferably 75%, stir, leave standstill 0.5-2h, preferably 1h;
(4) filter, filtrate is used the equal-volume n-butanol extraction again, merges water;
(5) with vinylbenzene and divinylbenzene ion exchange resin (as the D001 type ion exchange resin) post of monomer polymerization with merging the direct mistake of the aqueous solution in (4), the most of plant pigments of elder generation's water flush away, use the ammonia soln wash-out of 0.05M-0.2M again, the ammonia soln of 0.1M preferably, effect is better;
(6) will cross ion exchange resin column liquid and be evaporated to driedly, be dissolved in water, use acetone precipitation, add the acetone that the 10-50 of aqueous solution volume doubly measures, preferably 30 times of amounts;
(7) throw out is filtered, water-acetone recrystallization filters the back and is washed till white with small amount of acetone, obtains purity and be the dencichine more than 99%.
Have following remarkable advantage and progress on the technology of the present invention: 1) the inventive method is increased in behind the water extraction, adopts the method for ethanol sedimentation, removes a part of impurity, can tentatively improve the purity of product.2) adopting with vinylbenzene and divinylbenzene is ion exchange resin (as the D001 type ion exchange resin) column technology of monomer polymerization, use Sephadex LH-20 and CM Sephadex C-25 resin have been avoided, promptly reduced cost, accelerate treatment capacity again, can largely improve product purity simultaneously.3) separate out dencichine with acetone precipitation, method is easy, processing ease.4) can obtain the higher dencichine of content (can up to 99.5%).
Description of drawings
Fig. 1 is that gained dencichine reference substance of the present invention and sample thin-layer chromatogram compare;
Fig. 2 is a gained dencichine sample HPLC test result of the present invention;
Fig. 3 is that gained dencichine sample of the present invention and reference substance HPLC figure compare.
Embodiment
Below in conjunction with embodiment and accompanying drawing the present invention is further specified.
Is that 95% ethanolic soln extracts 10h with pseudo-ginseng with 5 times volume ratio, is 95% ethanol again with 2 times volume ratio, extraction 4h, and the extraction temperature is a room temperature; Merge alcohol extract twice, reserve for other use.Residue is dried, add the flooding 12h of 10 times of amounts; Use the flooding 4h of 2 times of amounts again, the extraction temperature is a room temperature; Filter, filtrate is concentrated into 3 times of amounts, and adding ethanol adjusting determining alcohol is 50%, stirs, and leaves standstill 0.5h; Filter, filtrate is used the equal-volume n-butanol extraction again, merges water; With merging the direct mistake of the aqueous solution is the D001 ion exchange resin column of monomer polymerization with vinylbenzene and divinylbenzene, the most of plant pigments of elder generation's water flush away, use the ammonia soln wash-out of 0.05M again, to cross ion exchange resin column liquid is evaporated to dried, be dissolved in water, use acetone precipitation, add the acetone of 10 times of amounts of aqueous solution volume; Throw out is filtered, and water-acetone recrystallization filters the back and is washed till white with small amount of acetone, obtains purity and be 99.15% dencichine.
Is that 95% ethanolic soln extracts 15h with pseudo-ginseng with 10 times volume ratio, is 95% ethanol again with 6 times volume ratio, extraction 6h, and the extraction temperature is a room temperature; Merge alcohol extract twice, reserve for other use.Residue is dried, add the flooding 15h of 15 times of amounts; Use the flooding 6h of 6 times of amounts again, the extraction temperature is a room temperature; Filter, filtrate is concentrated into 3 times of amounts, and adding ethanol adjusting determining alcohol is 75%, stirs, and leaves standstill 1h; Filter, filtrate is used the equal-volume n-butanol extraction again, merges water; With merging the direct mistake of the aqueous solution is the D001 ion exchange resin column of monomer polymerization with vinylbenzene and divinylbenzene, the most of plant pigments of elder generation's water flush away, use the ammonia soln wash-out of 0.1M again, to cross ion exchange resin column liquid is evaporated to dried, be dissolved in water, use acetone precipitation, add the acetone of 30 times of amounts of aqueous solution volume; Throw out is filtered, and water-acetone recrystallization filters the back and is washed till white with small amount of acetone, obtains purity and be 99.50% dencichine.
Is that 95% ethanolic soln extracts 20h with pseudo-ginseng with 15 times volume ratio, is 95% ethanol again with 10 times volume ratio, extraction 10h, and the extraction temperature is a room temperature; Merge alcohol extract twice, reserve for other use.Residue is dried, add the flooding 20h of 20 times of amounts; Use the flooding 10h of 10 times of amounts again, the extraction temperature is a room temperature; Filter, filtrate is concentrated into 3 times of amounts, and adding ethanol adjusting determining alcohol is 90%, stirs, and leaves standstill 2h; Filter, filtrate is used the equal-volume n-butanol extraction again, merges water; With merging the direct mistake of the aqueous solution is the D001 ion exchange resin column of monomer polymerization with vinylbenzene and divinylbenzene, the most of plant pigments of elder generation's water flush away, use the ammonia soln wash-out of 0.2M again, to cross ion exchange resin column liquid is evaporated to dried, be dissolved in water, use acetone precipitation, add the acetone of 50 times of amounts of aqueous solution volume; Throw out is filtered, and water-acetone recrystallization filters the back and is washed till white with small amount of acetone, obtains purity and be 99.38% dencichine.
Thin layer chromatography analysis with the dissolving of dencichine reference substance and samples with water after, point sample on same chromatographic paper, use propyl carbinol: water: acetate: dehydrated alcohol, 4: 2: 1: 1 (V/V) launched, and taking-up is dried, and spray is with 0.2% ninhydrin solution, 105 ℃ of colour developings, sample has identical Rf value (seeing accompanying drawing 1) with reference substance, and presents same red-purple spot, inclusion-free spot in the sample.
HPLC analyzes after dencichine reference substance and the samples with water dissolving, and sample introduction under identical conditions obtains identical color atlas, and retention time is identical, and peak shape is also identical.See accompanying drawing 2 and 3.
The mensuration infrared spectra λ of NMR and IR
Max KBrCm
-1: 3420,3520 (hydroxyl peak); 3040,1619,1545 (amino acid I, II bands); 3300,1545,1250 (secondary amide I, II, III bands); 2620,2500 (serial small peaks); 2800,1440 (CH
2-peak); 1380 places do not have the expression of absorption nothing-CH
3
The dencichine structural formula
Nuclear magnetic resonance spectrum (
1H NMR and
13C NMR) spectrum peak ownership is listed in the table below
| H | δ( 1H) | C | δ( 13C) |
| 2 3 3 | 4.24(1H，dd，J＝6.8，4.2Hz) 3.87(1H，ABd，J＝15.0，4.15 Hz，) 3.96(1H，ABd，J＝15.0，4.15 HZ) | 1 2 3 4 5 | 166.737 56.314 42.075 173.207 167.012 |
MS detects the mass spectroscopy API-ES of this compound, m/e:175 (M-1
+, C
5H
8N
2O
5) (100%), 176.Be dencichine by analysis.
HPLC,
1H NMR,
13C NMR, IR, MS analyze:
NMR, IR, MS check and analysis are dencichine, and are consistent with bibliographical information, product is carried out HPLC detect, and the results are shown in accompanying drawing 2.
Pharmacological evaluation
1. bleeding time: get 30 of body weight 18-22g healthy mices, the male and female dual-purpose is divided into 3 groups at random: positive control " aminomethylbenzoic acid injection " group; The dencichine group; Blank group.Except that the blank group, the equal abdominal injection of medicine three days, 30min after last administration, in order to cutting the horizontal end with mouse tail point 0.5cm place, blood flows out the back timing voluntarily respectively, inhales to dehematize with filter paper every 15s and drips once, naturally stop until blood, calculate the bleeding time, the results are shown in Table 1.
2. coagulation time test: get 30 of 18-22g healthy mices, the male and female dual-purpose is divided into 3 groups at random, and group is the same.Except that the blank group, the equal abdominal injection of medicine is that the glass-tube kapillary of 1mm inserts mouse angular vein clump and gets blood with internal diameter behind the 1h, and the blood post reaches 5cm. to the capillary glass-tube.Every fracture one section of capillary glass-tube of 30s, check to have or not the blood clotting silk to occur.Calculating is taken a blood sample to from the capillary glass-tube and the time of blood clotting silk occurred, is the clotting time, the results are shown in Table 1.
3. platelet count: get 30 of body weight 18-22g healthy mices, the male and female dual-purpose is divided into 7 groups immediately, and group is the same.Except that the blank group, the equal abdominal injection of medicine three days is got mouse tail vein blood 20ul, is blown into and fills 0.38ml thrombocyte diluent in vitro, abundant mixing, microscopically counting.Total number of blood platelet in 5 medium squares of blood cell counting plate be multiply by 1000, promptly get the platelet counts in the 1ul blood, the results are shown in Table 1.
Table 1 dencichine hemostasis experimental result
| Group | Blank group | Control group | The dencichine group |
| Clotting time in bleeding time platelet count (* 10 3) | 33.95±16.08 2.49±0.63 572.50±164.64 | 7.95±6.09** 1.22±0.50** 798.36±194.90* | 4.80±2.85** 1.06±0.64** 949.30±204.57** |
Annotate: compare with control group: * P＜0.05, compare with control group: * * P＜0.01
Table 1 The pharmacological results shows that all dencichine has tangible haemostatic effect.
Claims (9)
1, a kind of method of extracting dencichine from pseudo-ginseng is characterized in that, comprises the steps:
(1) be 95% ethanolic soln with pseudo-ginseng with 5-15 volume ratio doubly, alcohol extracting 10-20h; Be 95% ethanol again with 2-10 volume ratio doubly, alcohol extracting 4-10h;
(2) merge twice alcohol extract, residue is dried, add the flooding that 10-20 doubly measures, extract 10-20h, the flooding of doubly measuring with 2-10 is extracted 4-10h again, and the extraction temperature is a room temperature;
(3) filter, filtrate concentrates, and adding ethanol adjusting determining alcohol is 50-90%, stirs, and leaves standstill 0.5-2h;
(4) filter, filtrate is used the equal-volume n-butanol extraction again, merges water;
(5) be the ion exchange resin column of monomer polymerization with merging the direct mistake of the aqueous solution in (4) with vinylbenzene and divinylbenzene, the ammonia soln wash-out is used in first water flushing again, and ammonia soln concentration is 0.05M-0.2M;
(6) will cross ion exchange resin column liquid and be evaporated to driedly, be dissolved in water, use acetone precipitation, amounts of acetone be aqueous solution volume 10-50 doubly;
(7) throw out is filtered, recrystallization filters the back and is washed till white with acetone, obtains purity and be the dencichine more than 99%.
2, the method for extracting dencichine from pseudo-ginseng as claimed in claim 1 is characterized in that, in the step (1), and the ethanolic soln of 10 times of amounts of pure drawings for the first time, the ethanolic soln of 5 times of amounts of pure drawings for the second time.
3, the method for extracting dencichine from pseudo-ginseng as claimed in claim 1 or 2 is characterized in that, in the step (1), the alcohol extracting time is 12h for the first time, and the alcohol extracting time is 6h for the second time, and the extraction temperature is a room temperature.
4, the method for extracting dencichine from pseudo-ginseng as claimed in claim 1 is characterized in that, in the step (2), flooding is with the water of 10 times of amounts for the first time, and the second time, flooding was with the water of 5 times of amounts.
5, as claim 1 or the 4 described methods of extracting dencichine from pseudo-ginseng, it is characterized in that in the step (2), the flooding time is 12h for the first time, the flooding time is 6h for the second time.
6, the method for extracting dencichine from pseudo-ginseng as claimed in claim 1 is characterized in that, in the step (3), adding ethanol adjusting determining alcohol is 75%, leaves standstill 1h.
7, the method for extracting dencichine from pseudo-ginseng as claimed in claim 1 is characterized in that in the step (5), ammonia soln concentration is 0.1M.
8, the method for extracting dencichine from pseudo-ginseng as claimed in claim 1 is characterized in that, in the step (6), when adding acetone precipitation, amounts of acetone is 30 times of aqueous solution volume.
9, the method for extracting dencichine from pseudo-ginseng as claimed in claim 1 is characterized in that, in the step (7), adopts the mixed solution of water and acetone during recrystallization.
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| CN103230617A (en) * | 2013-04-24 | 2013-08-07 | 四川大学 | Collagen/chitosan micro-nano fiber composite hemostatic membrane material and preparation method thereof |
| CN103566020A (en) * | 2013-08-30 | 2014-02-12 | 贵阳新天药业股份有限公司 | Traditional Chinese medicinal composition for preventing and treating female climacteric syndrome |
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| CN107162926A (en) * | 2017-06-16 | 2017-09-15 | 云南多糖生物科技有限公司 | The extracting method of dencichine and its application and the extracting method of pseudo-ginseng amino acid |
| CN107970265A (en) * | 2017-12-28 | 2018-05-01 | 云南汉德生物技术有限公司 | A kind of method for extracting Folium Notoginseng glycoside |
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Family Cites Families (2)
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| CN1267665A (en) * | 1999-03-19 | 2000-09-27 | 蓝桂华 | Preparation of notoginseng essence as efficient hemostatic material |
| CN1166679C (en) * | 2001-10-26 | 2004-09-15 | 香港生物科技研究院 | Method for extracting and separating notoginsenoside R1, panaxcoside Re, pseudo-ginseng element from pseudo-ginseng crude powder |
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2006
- 2006-06-22 CN CNB2006100279621A patent/CN100336801C/en not_active Expired - Fee Related
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| CN103566020A (en) * | 2013-08-30 | 2014-02-12 | 贵阳新天药业股份有限公司 | Traditional Chinese medicinal composition for preventing and treating female climacteric syndrome |
| CN107162926A (en) * | 2017-06-16 | 2017-09-15 | 云南多糖生物科技有限公司 | The extracting method of dencichine and its application and the extracting method of pseudo-ginseng amino acid |
| CN107970265A (en) * | 2017-12-28 | 2018-05-01 | 云南汉德生物技术有限公司 | A kind of method for extracting Folium Notoginseng glycoside |
| CN107970265B (en) * | 2017-12-28 | 2021-05-04 | 云南汉德生物技术有限公司 | Method for extracting sanchinoside |
| CN108675939A (en) * | 2018-07-10 | 2018-10-19 | 山东端信堂大禹药业有限公司 | A kind of device and its extracting method extracting dencichine from Radix Notoginseng |
| CN109078115A (en) * | 2018-09-25 | 2018-12-25 | 宁波森果医药科技有限公司 | A kind of Chinese materia medica preparation and preparation method thereof for hemorrhage of digestive tract |
| CN112979489A (en) * | 2021-02-23 | 2021-06-18 | 云南三七科技有限公司 | Method for preparing amino acid from notoginseng flower |
| CN112979489B (en) * | 2021-02-23 | 2023-05-02 | 云南三七科技有限公司 | Method for preparing amino acid from pseudo-ginseng flowers |
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