CN102060835A - Method for preparing rubimaillin - Google Patents
Method for preparing rubimaillin Download PDFInfo
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- CN102060835A CN102060835A CN2010106039990A CN201010603999A CN102060835A CN 102060835 A CN102060835 A CN 102060835A CN 2010106039990 A CN2010106039990 A CN 2010106039990A CN 201010603999 A CN201010603999 A CN 201010603999A CN 102060835 A CN102060835 A CN 102060835A
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- rubimaillin
- madder
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Abstract
The invention relates to a method for preparing rubimaillin. The method comprises the following steps of: drying madder and pulverizing; extracting with an organic solvent; concentrating; suspending with water; continuously separating and purifying with macroporous absorption resin and silicagel column chromatography; concentrating eluent; crystallizing with dichloromethane-acetone to obtain pure rubimaillin. The entire separation process has low requirements on the environment, and the method has low cost, is convenient to operate, easy to control and suitable for industrialized production.
Description
Technical field:
The present invention relates to a kind of preparation method of rubimaillin, belong to natural medicine field, be specifically related to a kind of macroporous resin and silica gel column chromatography technology utilized, from madder, extract the method for purifying rubimaillin.
Background technology:
Madder is dry root and the rhizome of madder wort madder Rubia cordifolia L..Beginning is stated from Shennong's Herbal, has cool blood, a stasis of blood of dispelling, the effect of stopping blooding, stimulating the menstrual flow, be used for haematemesis, bleeding from five sense organs or subcutaneous tissue, uterine bleeding, traumatic hemorrhage, silt resistance through close, arthralgia, tumbling and swelling.The madder main product in the weinan, ground such as Songxian County, Henan, Anhui, Jiangsu, Shandong.At present, contain multiple anthraquinone component, naphthoquinones constituents, ring six peptide component in the known madder, wherein the naphthoquinones constituents is the characteristic chemical constituent of madder class medicinal material.Madder has significant hemostasis, antibacterial, antiinflammation, rubimaillin is one of its main effective constituent, experiment in vitro shows that rubican all has significant inhibitory effect to streptococcus aureus, Bacillus proteus, colon bacillus, Pseudomonas aeruginosa, Salmonellas and klebsiella etc.Liu Guang etc. find that the rubimaillin in the methanol solution is unstable under illumination, measure its content and answer the lucifuge operation.It is pseudo-ginseng, the hemorrhage main efficient part of madder treatment palace ring that Tan Chaoyang found through experiments Radix Notoginseng total arasaponins, dencichine, rubimaillin, and Radix Notoginseng total arasaponins, dencichine, rubimaillin all can make tame rabbit uterus homogenate 6-K-PGF
1a/ TXB
2Ratio obviously reduces, and pseudo-ginseng, the madder residuum after extracting does not have a little less than respective action or the effect.The experiment discovery SQ reorganization compound of You Zhaoling etc. can improve puts Cu-IUD rabbit blood vessels of endometrium endotheliocyte and smooth muscle cell plastosome oedema and cavity change, the foam sample that improves mesenchymal cell becomes, experiment in vitro shows, active principle rubimaillin wherein is to arachidonic acid, collagen-induced rabbit platelet is assembled stronger restraining effect, platelet activating factor inductive platelet aggregation also there is restraining effect, in another group experiment, find the model group rabbit hematocrit value in the experiment, whole blood viscosity (low cutting, in cut, height is cut), the blood plasma viscosity all significantly improves, with blank group difference significance (P＜0.01) is arranged, respectively through Radix Notoginseng total arasaponins, dencichine, all can reduce above index after rubimaillin and the indomethacin treatment, and Radix Notoginseng total arasaponins, dencichine, rubimaillin and positive controls medicine make the index of surveying reach normally equally, all have therapeutic action; Therefore, Radix Notoginseng total arasaponins, dencichine, rubimaillin are the SQ compound effective components, by regulating hemorheological property, reach the anastalsis of eliminate blood stasis and promote tissue regeneration.
At present domestic less to rubimaillin extraction and purification process research aspect document, Tan Chaoyang, Liu Qian, Peng Liang etc. all adopt alcohol reflux, this method only to obtain the madder crude extract, can't obtain high-load rubimaillin.
Summary of the invention:
The object of the present invention is to provide a kind of preparation method of rubimaillin, can obtain high-load rubimaillin.This method is not high to environmental requirement, and cost is low, and is simple to operate, is easy to control, is suitable for from madder preparation of industrialization and extracts this compound.
The objective of the invention is to be achieved through the following technical solutions:
A kind of preparation method of rubimaillin comprises the following steps:
A. the madder root and rhizome is pulverized, added organic solvent and extract, extract twice, filter, keep filtrate, concentrate;
B. use aqueous suspension, add macroporous adsorptive resins absorption, 80-100% methyl alcohol or ethanol elution are collected elutriant, are evaporated to dried;
C. above-mentioned enriched material adopts silica gel column chromatography separating purification, and petroleum ether-ethyl acetate, sherwood oil-methyl alcohol or normal hexane-ethyl acetate gradient elution is collected flow point, according to the TLC tracking monitor same stream is divided to merge;
D. with rubimaillin flow point reclaim under reduced pressure reagent, be concentrated into driedly, methylene dichloride-acetone recrystallization obtains the pure product of rubimaillin.
Organic solvent is selected from one or more in acetone, ethanol, ethyl acetate, the methyl alcohol among the described step a..
The optional microwave extraction of extracting method among the described step a., supersound extraction, heating and refluxing extraction, diacolation extract or a kind of in extracting of Soxhlet.
Nonpolar or low-pole resins such as the optional XSD-1 of macroporous resin, D101, AB-8, HPD100 among the described step b..
The eluent volume ratio is 49 in the described step c: 1-2: 1.
Preparation method of the present invention is simple, and cost is low, select resin absorption for use, and enriching quantity is big, good impurity removing effect, and energy consumption is low, avoids the high temperature recurring structure to change; Adopt the silicagel column good separating effect.
Embodiment:
The following examples can illustrate in greater detail the present invention, but do not limit the present invention in any form.
Embodiment 1:
Producing madder with Shaanxi is raw material, gets 10kg, extracts with 90% acetone Soxhlet, filters, and gets filtrate, the dregs of a decoction is repeated aforesaid operations again extract once, merges filtrate twice, concentrated madder medicinal extract; With the medicinal extract aqueous suspension, adding D101 macroporous adsorptive resins adsorbs, and the first water wash-out impurity in absorption back again with 80% ethanol elution, is collected elutriant, and decompression recycling ethanol is again with the extremely approaching no moisture of anhydrous sodium sulfate dehydration; Adopt silica gel column chromatography to separate, petroleum ether-ethyl acetate carries out gradient elution for system's solvent, the effluent volume proportioning is 49: 1,19: 1,9: 1,2: 1, collects elutriant, and every 500ml is a flow point, according to the TLC tracking monitor, merge identical flow point, concentrating under reduced pressure rubimaillin flow point is used acetone recrystallization again, vacuum-drying gets the 43.2g rubimaillin, and content is 90.36%.
Embodiment 2:
Producing madder with Shaanxi is raw material, gets 10kg, extracts with the methyl alcohol Soxhlet, filters, and gets filtrate, the dregs of a decoction is repeated aforesaid operations again extract once, merges filtrate twice, concentrate madder medicinal extract; With the medicinal extract aqueous suspension, the adding macroporous adsorptive resins adsorbs, and the first water wash-out impurity in absorption back again with 80% ethanol elution, is collected elutriant, and decompression recycling ethanol is again with the extremely approaching no moisture of anhydrous sodium sulfate dehydration; Adopt silica gel column chromatography to separate, sherwood oil-chloroform carries out gradient elution for system's solvent, the effluent volume proportioning is 49: 1,19: 1,9: 1,2: 1, collects elutriant, and every 500ml is a flow point, according to the TLC tracking monitor, merge identical flow point, concentrating under reduced pressure rubimaillin flow point is used acetone recrystallization again, vacuum-drying gets the 57.2g rubimaillin, and content is 91.45%.
Embodiment 3:
Producing madder with Shaanxi is raw material, gets 20kg, extracts with 90% alcohol heating reflux, filters, and gets filtrate, the dregs of a decoction is repeated aforesaid operations again extract once, merges filtrate twice, concentrated madder medicinal extract; With the medicinal extract aqueous suspension, adding HPD100 macroporous adsorptive resins adsorbs, and the first water wash-out impurity in absorption back again with 90% methanol-eluted fractions, is collected elutriant, and decompression recycling ethanol is again with the extremely approaching no moisture of anhydrous sodium sulfate dehydration; Adopt silica gel column chromatography to separate, sherwood oil-chloroform carries out gradient elution for system's solvent, the effluent volume proportioning is 49: 1,19: 1,9: 1,2: 1, collects elutriant, and every 500ml is a flow point, according to the TLC tracking monitor, merge identical flow point, concentrating under reduced pressure rubimaillin flow point is used acetone recrystallization again, vacuum-drying gets the 76.3g rubimaillin, and content is 92.43%.
Embodiment 4:
Producing madder with Shaanxi is raw material, gets 20kg, with 60% ethyl acetate heating and refluxing extraction, filters, and gets filtrate, the dregs of a decoction is repeated aforesaid operations again extract once, merges filtrate twice, concentrated madder medicinal extract; With the medicinal extract aqueous suspension, adding AB-8 macroporous adsorptive resins adsorbs, and the first water wash-out impurity in absorption back again with 95% methanol-eluted fractions, is collected elutriant, and decompression recycling ethanol is again with the extremely approaching no moisture of anhydrous sodium sulfate dehydration; Adopt silica gel column chromatography to separate, petroleum ether-ethyl acetate carries out gradient elution for system's solvent, the effluent volume proportioning is 49: 1,19: 1,9: 1,2: 1, collects elutriant, and every 500ml is a flow point, according to the TLC tracking monitor, merge identical flow point, concentrating under reduced pressure rubimaillin flow point is used acetone recrystallization again, vacuum-drying gets the 78.4g rubimaillin, and content is 94.26%.
Embodiment 5:
Producing madder with Shaanxi is raw material, gets 30kg, with 90% methyl alcohol microwave extraction, filters, and gets filtrate, the dregs of a decoction is repeated aforesaid operations again extract once, merges filtrate twice, concentrated madder medicinal extract; With the medicinal extract aqueous suspension, adding XSD-1 macroporous adsorptive resins adsorbs, and the first water wash-out impurity in absorption back again with 85% methanol-eluted fractions, is collected elutriant, and decompression recycling ethanol is again with the extremely approaching no moisture of anhydrous sodium sulfate dehydration; Adopt silica gel column chromatography to separate, normal hexane-ethyl acetate is carried out gradient elution for system's solvent, the effluent volume proportioning is 49: 1,19: 1,9: 1,2: 1, collects elutriant, and every 500ml is a flow point, according to the TLC tracking monitor, merge identical flow point, concentrating under reduced pressure rubimaillin flow point is used acetone recrystallization again, vacuum-drying gets the 112.5g rubimaillin, and content is 95.12%.
Embodiment 6:
Producing madder with Shaanxi is raw material, gets 30kg, use 70% ethanol Soxhlet extraction, filters, and gets filtrate, the dregs of a decoction is repeated aforesaid operations again extract once, merges filtrate twice, concentrated madder medicinal extract; With the medicinal extract aqueous suspension, adding D101 macroporous adsorptive resins adsorbs, and the first water wash-out impurity in absorption back again with 90% ethanol elution, is collected elutriant, and decompression recycling ethanol is again with the extremely approaching no moisture of anhydrous sodium sulfate dehydration; Adopt silica gel column chromatography to separate, sherwood oil-methyl alcohol carries out gradient elution for system's solvent, the effluent volume proportioning is 49: 1,19: 1,9: 1,2: 1, collects elutriant, and every 500ml is a flow point, according to the TLC tracking monitor, merge identical flow point, concentrating under reduced pressure rubimaillin flow point is used acetone recrystallization again, vacuum-drying gets the 104.6g rubimaillin, and content is 93.37%.
Embodiment 7:
Producing madder with Shaanxi is raw material, gets 50kg, with 95% methyl alcohol supersound extraction, filters, and gets filtrate, the dregs of a decoction is repeated aforesaid operations again extract once, merges filtrate twice, concentrated madder medicinal extract; With the medicinal extract aqueous suspension, adding AB-8 macroporous adsorptive resins adsorbs, and the first water wash-out impurity in absorption back again with 90% methanol-eluted fractions, is collected elutriant, and decompression recycling ethanol is again with the extremely approaching no moisture of anhydrous sodium sulfate dehydration; Adopt silica gel column chromatography to separate, petroleum ether-ethyl acetate carries out gradient elution for system's solvent, the effluent volume proportioning is 49: 1,19: 1,9: 1,2: 1, collects elutriant, and every 500ml is a flow point, according to the TLC tracking monitor, merge identical flow point, concentrating under reduced pressure rubimaillin flow point is used acetone recrystallization again, vacuum-drying gets the 184.0g rubimaillin, and content is 92.33%.
Claims (6)
1. the preparation method of a rubimaillin comprises the following steps:
A. the madder root and rhizome is pulverized, added organic solvent and extract, extract twice, filter, keep filtrate, concentrate;
B. use aqueous suspension, add macroporous adsorptive resins absorption, 80-100% methyl alcohol or ethanol elution are collected elutriant, are evaporated to dried;
C. above-mentioned enriched material adopts silica gel column chromatography separating purification, and petroleum ether-ethyl acetate, sherwood oil-chloroform or normal hexane-ethyl acetate gradient elution is collected flow point, according to the TLC tracking monitor same stream is divided to merge;
D. with rubimaillin flow point reclaim under reduced pressure reagent, be concentrated into driedly, methylene dichloride-acetone recrystallization obtains the pure product of rubimaillin.
2. according to the preparation method of the described rubimaillin of claim 1, it is characterized in that used crude drug madder is that madder is produced in Shaanxi among the described step a..
3. according to the preparation method of the described rubimaillin of claim 1, it is characterized in that organic solvent among the described step a. is selected from one or more in acetone, ethanol, ethyl acetate, the methyl alcohol.
4. according to the preparation method of the described rubimaillin of claim 1, it is characterized in that the optional microwave extraction of extracting method among the described step a., supersound extraction, heating and refluxing extraction, diacolation extract or a kind of in extracting of Soxhlet.
5. according to the preparation method of the described rubimaillin of claim 1, it is characterized in that nonpolar or low-pole resins such as the optional XSD-1 of macroporous resin, D101, AB-8, HPD100 among the described step b..
6. according to the preparation method of the described rubimaillin of claim 1, it is characterized in that the eluent volume ratio is 49 in the described step c: 1-2: 1.
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| CN2010106039990A CN102060835A (en) | 2010-12-24 | 2010-12-24 | Method for preparing rubimaillin |
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| CN2010106039990A CN102060835A (en) | 2010-12-24 | 2010-12-24 | Method for preparing rubimaillin |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102875517A (en) * | 2012-10-08 | 2013-01-16 | 河南大学 | Mollugin and preparation method and application thereof |
| CN103040984A (en) * | 2012-12-13 | 2013-04-17 | 大兴安岭林格贝有机食品有限责任公司 | Novel technology method for extracting madder pigment from wild madder |
| CN103054976A (en) * | 2011-10-21 | 2013-04-24 | 上海中医药大学 | Chinese medicinal composition for treating thrombopenia as well as preparation method and application of composition |
| CN111235186A (en) * | 2020-03-19 | 2020-06-05 | 杭州彩润科技有限公司 | Method for extracting plant dye by microbial transformation of rubia hexapetala |
| CN115141172A (en) * | 2022-07-27 | 2022-10-04 | 江阴天江药业有限公司 | Method for preparing active monomer rubiadin from madder |
-
2010
- 2010-12-24 CN CN2010106039990A patent/CN102060835A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103054976A (en) * | 2011-10-21 | 2013-04-24 | 上海中医药大学 | Chinese medicinal composition for treating thrombopenia as well as preparation method and application of composition |
| CN102875517A (en) * | 2012-10-08 | 2013-01-16 | 河南大学 | Mollugin and preparation method and application thereof |
| CN103040984A (en) * | 2012-12-13 | 2013-04-17 | 大兴安岭林格贝有机食品有限责任公司 | Novel technology method for extracting madder pigment from wild madder |
| CN103040984B (en) * | 2012-12-13 | 2016-05-25 | 大兴安岭林格贝寒带生物科技股份有限公司 | A kind of process of extracting madder color from wild madder |
| CN111235186A (en) * | 2020-03-19 | 2020-06-05 | 杭州彩润科技有限公司 | Method for extracting plant dye by microbial transformation of rubia hexapetala |
| CN115141172A (en) * | 2022-07-27 | 2022-10-04 | 江阴天江药业有限公司 | Method for preparing active monomer rubiadin from madder |
| CN115141172B (en) * | 2022-07-27 | 2024-02-23 | 江阴天江药业有限公司 | Method for preparing active monomer alizarin from madder |
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Application publication date: 20110518 |