CN1473830A - Process for extracting matrine and sophoridine from sophora viciifolia or sophora moocroftiana - Google Patents
Process for extracting matrine and sophoridine from sophora viciifolia or sophora moocroftiana Download PDFInfo
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- CN1473830A CN1473830A CNA031370497A CN03137049A CN1473830A CN 1473830 A CN1473830 A CN 1473830A CN A031370497 A CNA031370497 A CN A031370497A CN 03137049 A CN03137049 A CN 03137049A CN 1473830 A CN1473830 A CN 1473830A
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Abstract
The process of extracting matrine and sophoridine from sophora viciifolia or sophork moocroftiana includes various steps in certain order. The present invention has the advantages of rich material source, simple technological process, and safe hydrogenation at normal temperature and normal pressure. The extracted matrine and sophoridine have the functions of killing bacteria, diminishing inflammation, resisting virus and resisting cancer.
Description
Technical field
The present invention relates to from natural phant, extract the technology of nitrogen-containing heterocycle compound, specifically relate to from Root of Vetchleaf Sophora or Sophora moocroftiana(Wall, extract the technology of matrine, sophorine.
Background technology
Root of Vetchleaf Sophora S.viciifolia or sand are given birth to alkali S.moorcroftiana two kind of plant and are all originated in western China, especially western desert region is Sophora pulse family wild plant, and complete stool all contains Radix Sophorae Flavescentis alkaloid, owing to sand fixation is arranged, can only get its over-ground part and do technology production.
Root of Vetchleaf Sophora contains alkaloid: sophocarpine, Sophocarpidin, sophoramine, neosophoramine alkali, sophor-anol, matrine, Oxymatyine, sophorine etc.
Sophora moocroftiana(Wall contains alkaloid: matrine, Oxymatyine, sophocarpine, Sophocarpidin etc.
Sophocarpine, Sophocarpidin, sophor-anol, sophoramine, dehydrogenation matrine with the matrine structural similitude are referred to as kuh-seng alkene alkali.On the D ring, all have duplex structure, open, be converted into matrine by hydride process.
With Root of Vetchleaf Sophora, the contained alkaloid structure of Sophora moocroftiana(Wall and molecular formula, division is as follows.Matrine matrine C
15H
24N
2O 74-76 ℃
Sophoramine (Sophoiamine) neosophoramine alkali (New-Sophoiamme)
Above-mentioned several, can pass through chemical reaction phase co-conversion.In sepn process, the matrine that alkalescence is more weak is easy to therefrom separate.Though the sophorine structure is similar with matrine, it is trans three-dimensional arrangement, is difficult to hydrogenating reduction.
Sophorine sophocarine C
15H
24N
2O 106-108 molecular weight 248
Contain more following four kinds in Root of Vetchleaf Sophora and the Sophora moocroftiana(Wall:
Matrine Oxymatyine Sophocarpidin sophorine sophocarpine sophocarpine C
15H
22N
2O 51-54 ℃
Sophocarpidin N-oxy sophocarine C
15H
22N
2O
2209 ℃
These alkaloids have antisepsis and anti-inflammation, antiviral, mycoplasma, anti-chlamydial effect.And sophorine has more anti-multiple virus, and is better to treatment gland cancer effect, and very big DEVELOPMENT PROSPECT is arranged.
These wild Chinese scholartrees mainly originate in the desert region, and root has sand fixation, and over-ground part can only burn material usefulness for the peasant does.Output is many, and low price produces great social benefit if make full use of, and is one of problem anxious to be solved at present, and is utilizing Root of Vetchleaf Sophora, Sophora moocroftiana(Wall to carry out the production of industrially scalable, and is still few at present.
Summary of the invention
The objective of the invention is to remedy above-mentioned the deficiencies in the prior art part, and a kind of technology of extracting matrine, sophorine from Root of Vetchleaf Sophora or Sophora moocroftiana(Wall of industrially scalable is provided.
The present invention seeks to realize by following measure:
A kind of technology of extracting matrine, sophorine from Root of Vetchleaf Sophora or Sophora moocroftiana(Wall is that in the following order step is carried out:
From Root of Vetchleaf Sophora or Sophora moocroftiana(Wall, extract and make sophocarpidine; The centrifugation sophocarpidine makes kuh-seng alkene alkali and matrine, through hydrogenation, makes thick matrine; Recrystallization makes refining matrine; Handle water, make refining sophorine;
Root of Vetchleaf Sophora or Sophora moocroftiana(Wall are extracted through 2-3% salt acid soak, refluxing toluene, boil, add 6 ‰ reductive agent S-WATs, extraction adds acid, makes sophocarpidine;
In sophocarpidine, add 30% sodium hydroxide, accent PH8-10, the toluene extraction, centrifugal, get most of kuh-seng alkene alkali and a small amount of matrine, through hydrogenation, centrifugation gets thick matrine;
After the sophocarpidine centrifugation, from aqueous solution mother liquor, add 30% sodium hydroxide, transfer PH9-11, chloroform extraction reclaims solvent, and centrifugation gets thick matrine; Thick matrine makes refining matrine through the sherwood oil recrystallization;
At described processing aqueous phase, add 20% sodium hydroxide, transfer PH12-13, toluene extraction 5 times, centrifugation, the sherwood oil recrystallization must be made with extra care sophorine;
Do not contain sophorine in the Sophora moocroftiana(Wall.
The present invention carries out gradient separations with different pH values, extracts in Root of Vetchleaf Sophora or the Sophora moocroftiana(Wall to contain different alkaloids.
Matrine monomer pH value is 9.5;
Kuh-seng alkene alkali contain several at quinoline on the western pyridine D ring 13-14 position all contain two keys, can hydrogenation, open and form matrine.But the Lehmannine alkali that in sophocarpine, also contains minute quantity, and its two keys are 12-13 positions on the D ring, two keys are opened in general difficult hydrogenation, need dual hydrogenation just can be reduced into matrine, because content is few, and uncomfortable industrial production.
During separating matrine, transfer PH8-10, purpose is that the alkaloid of this section is all extracted, and also contains a spot of matrine certainly.Key is also to contain the small part Oxymatyine, and PH hangs down about 7, becomes matrine through the hydrogenation Restore All.During separating matrine, PH10-11, purpose does not influence the separation of sophorine.
When separating sophorine, PH12-13, purpose is all separated the alkaloid of this section, and key is PH13, and sophorine is whole precipitate and separate.
The present invention has following advantage compared to existing technology: raw material of the present invention is grown in western desert region, raw material sources are abundant, the peasant is used for burning the ground prepared using of material, the matrine that therefrom makes, sophorine have antisepsis and anti-inflammation, antiviral, mycoplasma, anti-chlamydial effect.In addition, with the kuh-seng alkene alkali of matrine structural similitude, at quinoline in western pyridine D have several alkaloids of two keys on the ring, through hydrogenation, open two keys and form matrine, improved yield, can reach the finished product of 32-36%, technology is simple, the normal temperature and pressure hydrogenation is fool proof.
Description of drawings:
Fig. 1: the technology of from Root of Vetchleaf Sophora or Sophora moocroftiana(Wall, extracting sophocarpidine
Fig. 2: the technology of from sophocarpidine, extracting matrine, sophorine
Embodiment:
Enumerate an embodiment below, the present invention is further specified.
Embodiment 1
Concrete preparation method is as follows: (one) sophocarpidine extraction process A, pulverizing
Exsiccant Root of Vetchleaf Sophora or Sophora moocroftiana(Wall over-ground part are ground into sheet, in the metal trough of packing into, add the 2-3% hydrochloric acid solution, and the add-on material is 1: 0.5 with 2-3% hydrochloric acid liquid measure ratio, fully stirs, and is wetting, with the plastic cloth sealing, in case loss of moist lasts 8 hours.B, cold soaking
Wetting material is added in the maceration jar, add 2-3% hydrochloric acid, its amount is the 25-35% of weight of material, cold soaking 48 hours.
Material after cold soaking finishes is put into reactor, adds 2-5 times of toluene organic solvent of weight of material simultaneously.C, refluxing extraction
Stirring heating 80-100 ℃, refluxing extraction alkaloid totally 8 times lasts 2-3 hour at every turn, till the lifeless matter alkali reaction, extracts and finishes in material, discards the material slag, combining extraction liquid.D, recovery toluene
Temperature is higher slightly, but is no more than 100 ℃, promptly finishes in 2-3 hour.E, boil
After reclaiming solvent, begin to boil, add certain water gaging earlier, contract because of soup after reclaiming solvent thickens, general per kilogram stays and adds about 0.6 liter in water in the reduction of feed volume, adds 20% sulfuric acid, transfers PH3-4, adds 6 ‰ reductive agent S-WATs, stirs.Boiled 2 hours, temperature is controlled at the liquid homogeneity has small bubbles to get final product.
The purpose that adds reductive agent makes Oxymatyine be reduced into matrine, because of the PH of Oxymatyine is lower than
Kuh-seng alkene alkali.F, cooling
After having boiled, be cooled to below 10 ℃, add the water stirring and wash waste 3-4 time.Liquid can be put into and boil jar (an increase yield) for the second time.
Cooling fluid is separated with whizzer or eight layers of filtration filtered through gauze.G, abstraction impurity removal matter
In extractor, add a certain amount of acid solution after filtering, adding toluene amount is that 50% (acid solution: toluene is 2: 1) of acid solution stirred 10-20 minute, and about 40 minutes of standing demix is emitted lower floor's acid solution (staying methylbenzene extraction one time), emit toluene liquid again, extract so repeatedly three times.H, the extraction of alkalization toluene
Get and acid add 40% caustic lye of soda down through the stripped acid solution of toluene, transfer pH value to 12, with toluene continuous extraction 5 times (liquid 2, toluene 1), combining methylbenzene extracting solution, alkali lye can be drained during lifeless matter alkali on inspection.I, add the sophocarpidine after acid transition
To add 10% sulfuric acid in the methylbenzene extraction liquid, per kilogram adds 10% sulfuric acid liquid 50m1.Stirred 10-20 minute, the accent pH value is 4-5, preferably reaches 5, promptly.If pH value is had any problem to 4-5 by 12, needn't add more acid, can return strike-on and go in the extractor to stir, leave standstill.The alkali lye of emitting lifeless matter alkali discards, and the alkaloid in the acid solution is increased.(i.e. Radix Sophorae Flavescentis total alkaloids acid solution after the transition) (two) separate kuh-seng alkene alkali
A, sophocarpidine acid solution are put into still, use 30% caustic lye of soda, transfer PH 8-10, with toluene liquid extraction three times, (1: 1～2), extraction liquid is merged, reclaim solvent, fully stir, staticly settled 24 hours, with the throw out centrifugation, obtain big portion kuh-seng alkene alkali and a small amount of matrine and aqueous solution mother liquor.
B, the mixture of kuh-seng alkene alkali and a small amount of matrine is put into reactor, add the less water dissolving, add the nickel acetate catalyzer, consumption and kuh-seng alkene alkali weight ratio are 1: 8～10, and the envelope still feeds nitrogen and gets rid of air in the still, feeding 0.5～0.8～Kg/cm
2The hydrogen of pressure lasts 3-4 days, till thin-layer chromatography does not have kuh-seng alkene alkali, stops hydrogenation in reactant.Through centrifugation, decompression, concentrated solvent-free in reactant, promptly obtain the matrine of crude product, and the renewable repeated use of catalyst metal nickel.(3) separating matrine
A, the aqueous solution mother liquor in (two) A item is put into still, use 30% caustic lye of soda, after transferring PH9-11, with chloroform extraction totally 6 times, the 1-2 that each trichloromethane consumption is a mother liquor doubly, combining extraction liquid, through decompression, reclaim solvent, get the rough matrine of solid, it is standby that water gives over to the separation sophorine.
B, the matrine crude product in (two) B and (three) A binomial is merged, adds 8-10 times of sherwood oil, recrystallization obtains making with extra care the matrine crystal.(4) separation and Extraction of sophorine
(3) A is reclaimed the water that solvent and centrifugation go out gained merge, use 20% caustic lye of soda, accent PH12-13, fully stir, left standstill 24 hours, water layer is discarded, use methylbenzene extraction 5 times, the 1-2 of the about water of toluene consumption doubly, combining methylbenzene liquid, toluene is reclaimed in decompression, the centrifugation crystallization, the white, needle-shaped crystals of rough sophorine.Crude product with 8-10 times of sherwood oil recrystallization, is got the purified sophorine.
The material ratio is weight ratio among the present invention.
Differentiate that with thin layer chromatography the result is as follows:
74-76 ℃ of matrine white rib shape crystallization mp
105-107 ℃ of sophorine white, needle-shaped crystals mp
Metallic nickel catalyzer of the present invention has four kinds of nickelous acetates, nickelous chloride, single nickel salt, nickelous nitrate, can choose any one kind of them.
Nickel salt reacts the product that obtains with the ethanolic soln of dissolve with ethanol adding 1M sodium borohydride (potassium).The catalyzer that obtains is separated in the reaction back, can add less water, adds the ethanolic soln of 1M sodium borohydride (potassium) again, and reaction regeneration is reusable.
The compound of benzene has three kinds of benzene,toluene,xylenes, chooses any one kind of them, and generally uses toluene for well.
Haloalkane is two kinds of ethylene dichloride, trichloromethanes (chloroform), and it is good generally using chloroform.
Alkali lye is three kinds in sodium hydroxide, potassium hydroxide, yellow soda ash, preferably without potassium hydroxide.
Acid solution is sulfuric acid or hydrochloric acid, the most handy sulfuric acid.
Matrine of the present invention adopts thin layer chromatography to measure.Its method is as follows:
Get hydrogenation reaction testing sample and matrine standard model, be made into 5 ‰ with dehydrated alcohol respectively, get 10 microlitres, different positions o'clock on 1% carboxymethyl cellulose, 200 order silica gel G chromatoplates respectively, use the inclination ascending method, with benzene: acetone: diethylamine (5: 2: 0.2) mixture launches, and with rare Dragendorff's reagent colour developing, kuh-seng alkene alkali colour developing spot must not be arranged after the reduction.
After the present invention transition the sophocarpidine acid solution evaluation and content assaying method one, identify
1, get 2 test tubes of acid solution 5ml packing, splash into 1 of potassium mercuric iodide respectively, it is heavy to produce white
Form sediment.Another test tube drips 1 of iodine bismuth potassium test solution, produces brown precipitate.
2, get on the acid solution trace point 1% carboxymethyl cellulose 200 order silica gel g thin-layer plates, with tilting
Ascending method, with benzene: acetone: diethylamine (5: 2: 0.2) developping agent, taking-up is dried,
Spray shows to contain several pale brown color spot points with rare bismuth iodide developer.Two, assay
Adopt dry weight method method:
20g is in beaker for the precision weighing acid solution, with methylbenzene extraction 5 times, combining methylbenzene liquid, reclaims toluene, evaporate to dryness in water-bath, again in loft drier inner drying 5 hours to weight, precision is weighed once more, calculates the percentage ratio that contains Radix Sophorae Flavescentis total alkaloids.
Claims (6)
1, a kind of technology of extracting matrine, sophorine from Root of Vetchleaf Sophora or Sophora moocroftiana(Wall is characterized in that it is that in the following order step is carried out:
From Root of Vetchleaf Sophora or Sophora moocroftiana(Wall, extract and make sophocarpidine; The centrifugation sophocarpidine makes kuh-seng alkene alkali and matrine, through hydrogenation, makes thick matrine; Recrystallization makes refining matrine; Handle water, make refining sophorine.
2, extraction process according to claim 1 is characterized in that Root of Vetchleaf Sophora or Sophora moocroftiana(Wall are extracted through 2-3% salt acid soak, refluxing toluene, boils, and adds 6 ‰ reductive agent S-WATs, and extraction adds acid, makes sophocarpidine.
3, extraction process according to claim 1 is characterized in that in sophocarpidine, adds 30% sodium hydroxide, accent PH8-10, and the toluene extraction, centrifugal, get most of kuh-seng alkene alkali and a small amount of matrine, through hydrogenation, centrifugation gets thick matrine.
4, extraction process according to claim 1 is characterized in that thick matrine through the sherwood oil recrystallization, makes refining matrine.
5, extraction process according to claim 1 is characterized in that adding 20% sodium hydroxide at described processing aqueous phase, transfers PH12-13, toluene extraction 5 times, and centrifugation, the sherwood oil recrystallization must be made with extra care sophorine.
6, extraction process according to claim 1 is characterized in that not containing in the Sophora moocroftiana(Wall sophorine.
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| Application Number | Priority Date | Filing Date | Title |
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| CNA031370497A CN1473830A (en) | 2003-06-02 | 2003-06-02 | Process for extracting matrine and sophoridine from sophora viciifolia or sophora moocroftiana |
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| CNA031370497A CN1473830A (en) | 2003-06-02 | 2003-06-02 | Process for extracting matrine and sophoridine from sophora viciifolia or sophora moocroftiana |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101336958B (en) * | 2008-02-15 | 2013-01-16 | 上海海天医药科技开发有限公司 | Use of alkaloids extracted from sophora flavescens in preparing medicine for treating diseased induced by mycoplasma, chlamydia and fungus |
| CN106831778A (en) * | 2017-03-20 | 2017-06-13 | 刘煜华 | A kind of method that N-Oxysophocarpine is extracted in the tattooing from wolf's fang |
| CN108935779A (en) * | 2018-09-25 | 2018-12-07 | 红河卫生职业学院 | A kind of Sophora viciifolia health protection tea and preparation method thereof |
| CN111138433A (en) * | 2020-01-16 | 2020-05-12 | 西藏德康生物科技有限公司 | Method for extracting and purifying matrine from sophora moorcroftianain |
-
2003
- 2003-06-02 CN CNA031370497A patent/CN1473830A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101336958B (en) * | 2008-02-15 | 2013-01-16 | 上海海天医药科技开发有限公司 | Use of alkaloids extracted from sophora flavescens in preparing medicine for treating diseased induced by mycoplasma, chlamydia and fungus |
| CN106831778A (en) * | 2017-03-20 | 2017-06-13 | 刘煜华 | A kind of method that N-Oxysophocarpine is extracted in the tattooing from wolf's fang |
| CN108935779A (en) * | 2018-09-25 | 2018-12-07 | 红河卫生职业学院 | A kind of Sophora viciifolia health protection tea and preparation method thereof |
| CN108935779B (en) * | 2018-09-25 | 2021-07-30 | 红河卫生职业学院 | Nitraria tangutorum bobr health-care tea and preparation method thereof |
| CN111138433A (en) * | 2020-01-16 | 2020-05-12 | 西藏德康生物科技有限公司 | Method for extracting and purifying matrine from sophora moorcroftianain |
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