CN102675298B - Method for extracting and preparing silymarin from polygonum capitatum herb - Google Patents
Method for extracting and preparing silymarin from polygonum capitatum herb Download PDFInfo
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- CN102675298B CN102675298B CN201210153125.9A CN201210153125A CN102675298B CN 102675298 B CN102675298 B CN 102675298B CN 201210153125 A CN201210153125 A CN 201210153125A CN 102675298 B CN102675298 B CN 102675298B
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Abstract
The invention discloses a method for extracting and preparing silymarin from polygonum capitatum herb, and belongs to the technical field of medicines.. The method comprises the following steps of: firstly extracting the polygonum capitatum herb with petroleum ether under refluxing by heating, and removing extracting solution; then soaking with high-concentration ethanol solution, percolating or extracting under refluxing by heating, and concentrating under reduced pressure to obtain fluid extract; adding water into the fluid extract for suspension, extracting with ethyl acetate, carrying out concentration and evaporation on the extracting solution under reduced pressure, then adopting silica gel column chromatography, firstly removing impurities by elution of eluent of petroleum ether and ethyl acetate at a ratio being 2:1, then eluting by using eluent of petroleum ether and ethyl acetate at a ratio being 1:1, and carrying out concentration and evaporation on the eluate under reduced pressure to obtain the light-green silymarin powder.. The method disclosed by the invention has the advantages of no toxicity, environment-friendly effect, no pollution to environment, simpleness in operation, low cost, higher yield and purity of the silymarin and easiness in popularization.
Description
Technical field
The present invention relates to a kind of extraction from Herba Polygoni Capitati herb and prepare the method for silymarin, belong to medical art.
Background technology
Silymarin (
silybum marianum(L.) Gaertn.), for composite family (
compositae) Silybum (
silybum) plant, have another name called water and fly pheasant, Milk Thistle, mouse muscle, annual or biennial herb, originate in and be distributed in Europe, Mediterranean Zone, north African and Central Asia, China is introducing culture.Achene is used as medicine, nature and flavor hardship is cool, there is clearing heat and detoxicating, hepatic cholagogic effect, be mainly used to treat liver and gall diseases, the history of existing two thousand years [Chinese Plants will editorial board of the Chinese Academy of Sciences compiles, Chinese Plants will, the 78th volume the 1st fascicle. Beijing: Science Press, 1987:161-162. Chinese Pharmacopoeia Commission compiles. Pharmacopoeia of People's Republic of China (one) .2005 version. and Beijing: Chemical Industry Press, 2005:56-56].Later 1960s, German scholar Wagner H etc. is studied the liver-protecting activity composition of Silymarin, causes the extensive attention of people.Its main active ingredient is the flavone lignan compound that extraction and isolation obtains from fruit, be called silymarin (silymarin), by silibinin (silibinin), Isosilybin (isosilybin), four kinds of isomerss such as Silychristin (silychristin) and Silydianin (silydianin) are formed, wherein silibinin content is the highest, active best [Kvasnic ka F, B í ba B, S evc í k R.Analysis of the active components of silymarin.Journal of Chromatography A, 2003, 990 (1-2), 239-245].
Modern pharmacological research shows, silibinin and silymarin have significantly protects and stablizes hepatocellular effect, be used for the treatment of acute, chronic hepatitis, liver cirrhosis, the diseases such as liver poisoning, to hepatitis symptom, liver function all improves significantly, there is the effect of stabilized cell and intracellular biological film, also there is certain radiation-resistant effect [K en V, Walterov á D.Silybin and silymarin-new effects and applications.Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia, 2005, 149 (1): 29-41].Because silibinin and silymarin are considered to the preferably anti-hepatopathy toxic agent that activity is good, drug effect is high, have no side effect in anti-hepatovirus and Hepatocyte protection; be widely used in, in the products such as medicine, healthcare products, foods and cosmetics, demonstrating good potentiality to be exploited.In recent years, make a general survey of Silymarin produce market, the cultivated area of external Silymarin is in minimizing, reinforcement [Xu Defeng is relied on to Chinese silymarin crude product, Zhang Weiming, history sturdy pines, etc. domestic Silymarin Resource Utilization and prospect. food research and development, 2007,28(2): 157-161].
Along with the widespread use of domestic and international Silymarin related products, supply falls short of demand for silymarin and silibinin product, and obtain silymarin and mainly contain two kinds of methods, and a kind of is chemosynthesis silibinin method, another kind ofly prepares silymarin method for extraction.At present, the silymarin of bibliographical information and the extraction preparation method of silibinin are and obtain from Silymarin: such as, patent [Wang Lin, Fan Ganbin. a kind of preparation method .CN 101759687A of silymarin, 2010.06.30. Di Feng pavilion. the method .CN 102219781A.2011.10.19. extracting silymarin in Silymarin seed coat opens man of virtue and ability dragon, Zhao Hongzhu, Zeng Weimin, Deng. a kind of method .CN 102225085A extracting silymarin from Silymarin stalk, 2011.10.26] be from Silymarin fruit, the method preparing silymarin is extracted in the different sites such as seed coat or straw, patent [Zhu Zhanyuan, Li Bin, Wang Chunjian. a kind of extracting method .CN 101260105.2008.09.10 of silibinin] be the method for extraction purification silibinin from silymarin.But, only extract from this kind of plant of Silymarin and prepare silymarin and silibinin is difficult to meet actual needs, therefore, be badly in need of expanding and exploitation silymarin extracts the new resources of preparation.There is no bibliographical information at present from other plant, extract the method preparing silymarin.
Herba Polygoni Capitati (
polygonum capitatumbuch.-Ham.
exd. Don), for polygonaceae (
polygonaceae) Polygonum (
polygonum) plant, have another name called Herba Polygoni Capitati, Herba Polygoni Capitati, red acid bar, solar grass, water silk ball, perennial herb, mainly originate from the ground such as China Jiangxi, Hunan, Hubei, Sichuan, Guizhou, be born in more the hillside of height above sea level 600 ~ 3500 meters, mountain valley, wetland [Chinese Plants will editorial board of the Chinese Academy of Sciences. Chinese Plants will, 25th volume the 1st fascicle. Beijing: Science Press, 1998:57-58].Herba Polygoni Capitati is the distinctive seedling medicine in Guizhou, all herbal medicine, bitter, pungent, cool in nature, returns kidney, urinary bladder channel, has clearing heat and promoting diuresis, removing toxic substances pain relieving and blood and to fall apart effect of the stasis of blood, inducing diuresis for treating stranguria syndrome; The diseases such as conventional herb among the people or on the ground site treatment urinary system infection, blood urine, eczema, pyelonephritis, urocystitis, lithangiuria, rheumatalgia, wound, mumps, sore, diarrhoea, dysentery [the new medical college in Jiangsu. Chinese medicine voluminous dictionary, the first volume. Shanghai: Shanghai science tech publishing house, 1986:611-611. medicine Surveillance Authority of Guizhou Province. Guizhou Province's Chinese medicinal materials, Ethnic crude drugs quality standard, 1st edition. Guizhou: Guizhou Science Press, 2003:147-147].
Herba Polygoni Capitati main chemical compositions is volatile oil, phenolic acids, flavonoid compound etc.Experiment shows that Herba Polygoni Capitati has anti-oxidant activity, antipyretic, analgesia, anti-inflammatory, anti-microbial effect.Clinical can be used for, treats pyelonephritis, promotes row's stone etc.With Herba Polygoni Capitati be raw material make Chinese patent medicine preparation " Relinqing capsules ", " Relinqing Granula "; selected as national Chinese medicine protection kind; within 2002, enter National essential drugs list, within 2004, enter national basic medical insurance catalogue, clinical application is extensive.The master thesis of the present inventor [Yang Yang. Salvia przewalskii and Herba Polygoni Capitati chemical constitution study. Shanghai: The 2nd Army Medical College, 2009] in reported first Herba Polygoni Capitati containing flavones gelation mechanism of lignin grouting compounds such as silibinins, but do not illustrate the concrete extraction preparation method of silymarin.
Summary of the invention
The invention provides a kind of extraction from Herba Polygoni Capitati herb and prepare the method for silymarin.
The present invention realizes with following technical scheme: a kind of extraction from Herba Polygoni Capitati herb prepares the method for silymarin, and concrete steps are as follows:
(1) Herba Polygoni Capitati fluid extract is prepared:after routinely dry for Herba Polygoni Capitati herb medicinal material coarse powder first being used sherwood oil heating and refluxing extraction 1-3 time of 5 times of volumes, discard extracting solution; Soak with aqueous ethanolic solution 2 times of volumes of 80%-90% volumetric concentration, 20 times of volume diacolations or 5 times of volume heating and refluxing extraction 1-3 time, extracting solution is evaporated to and obtains Herba Polygoni Capitati fluid extract without alcohol taste, and yield is 25.0% ~ 30.0% again;
(2) silymarin is prepared:above-mentioned obtained Herba Polygoni Capitati fluid extract is added the water suspendible of 3-4 times of volume, with the extraction into ethyl acetate of 10 times of volumes, carry out silica gel column chromatography after extraction liquid concentrating under reduced pressure evaporate to dryness, the column chromatography silica gel of use is 100-200 order, and silica gel consumption is 7-10 times of quality of upper prop sample.First use sherwood oil: the elution of ethyl acetate=2:1, removing low-pole impurity, then use sherwood oil: the elution of ethyl acetate=1:1, sherwood oil: its volume of the elutriant of ethyl acetate is all no less than the silica gel amount of 6 times.Namely obtain light green silymarin powder after elutriant concentrating under reduced pressure evaporate to dryness, yield is 0.4% ~ 0.6%.Chemical constitution study shows this silymarin powder mainly containing silibinin, and Isosilybin, 2, the flavones lignin compounds such as 3-dehydro-silibinin, Silychristin, 2,3-dehydrogenation Silychristins, also containing impurity such as a small amount of Progallin A, Quercetins.
When above-mentioned extracting solution, extraction liquid or elutriant concentrating under reduced pressure, temperature is all no more than 65 DEG C.
With silibinin standard substance for contrast, adopt ultraviolet spectrophotometry to carry out purity detecting to this silymarin powder, record flavones lignin compound purity and be greater than 80%; Adopt high performance liquid chromatography to carry out assay to this silymarin powder, recording silibinin content is 60-70%.
the invention has the beneficial effects as follows:1, Late Cambrian is from the plant beyond Silymarin, namely obtains the method for silymarin in Herba Polygoni Capitati, develops the new resources extracting and prepare silymarin; 2, sherwood oil, ethyl acetate, ethanol three kinds of organic solvents are only used, asepsis environment-protecting in extraction preparation process, free from environmental pollution; 3, only carry out a silica gel column chromatography, easy and simple to handle, with low cost, the yield of silymarin and purity are all higher, and method is easy to promote.
Accompanying drawing explanation
Fig. 1 is that the present invention extracts the silymarin of preparation and the uv absorption spectra of silibinin standard substance.
Fig. 2 is the high-efficient liquid phase chromatogram that the present invention extracts the silymarin of preparation.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but enforcement of the present invention is not limited in this.
embodiment 1:
Herba Polygoni Capitati dry herb medicinal material 2000g, segment, grinding and sieving, the meal sherwood oil heating and refluxing extraction 3 times of 5 times of volumes, each 1 hour, elimination petroleum ether extract.After remaining meal drying, soak 24 hours, 20 times of volume seepage pressure effects with aqueous ethanolic solution 2 times of volumes of concentration 80% volumetric concentration.Be evaporated to percolate 60 DEG C without alcohol taste, obtain Herba Polygoni Capitati fluid extract 524g, yield is 26.2%.
Make cumulative volume be 1000ml after above-mentioned obtained Herba Polygoni Capitati fluid extract is added the water suspendible of 3-4 times of volume, with the extraction into ethyl acetate of 10 times of volumes, extraction liquid 60 DEG C of concentrating under reduced pressure recycling design, obtain Ethyl acetate fraction 21.4g after evaporate to dryness.Ethyl acetate fraction carries out 100-200 order silica gel column chromatography, silica gel consumption 200g, first use 1200ml sherwood oil: the elution of ethyl acetate=2:1, use 1200ml sherwood oil again: the elution of ethyl acetate=1:1, namely obtain light green silymarin powder 9.4g after elutriant 60 DEG C of concentrating under reduced pressure evaporates to dryness, yield is 0.47%.
purity detecting and assay:with (the self-control of silibinin standard substance, adopting area normalization method to detect purity through high performance liquid chromatograph is 98.83%) be contrast, use Shimadzu UV-2550 UV detector to carry out purity detecting at 287nm place to this silymarin powder, recording its flavones lignin compound purity is 82.44%.The uv absorption spectra of silymarin and silibinin standard substance is shown in Fig. 1, and in figure, Sa is silymarin, and Sb is silibinin standard substance.
Use Agilent 1100 high performance liquid chromatograph to carry out assay to this silymarin powder, chromatographiccondition is: chromatographic column, Di Ma company diamonsil C18 post (5 μ, 250mm × 4.6mm); Moving phase, methanol-water-Glacial acetic acid=48:52:1; Determined wavelength, 287nm; Column temperature, 35 DEG C; Flow velocity, 1.0ml/min.Recording silibinin content is 67.35%.High-efficient liquid phase chromatogram is shown in Fig. 2, and in figure, peak A, B are respectively a pair diastereomer of silibinin.
embodiment 2:
Herba Polygoni Capitati dry herb medicinal material 2000g, segment, grinding and sieving, the meal sherwood oil heating and refluxing extraction 3 times of 5 times of volumes, each 1 hour, elimination petroleum ether extract.After remaining meal drying, soak 24 hours with aqueous ethanolic solution 2 times of volumes of concentration 85% volumetric concentration, 5 times of volume heating and refluxing extraction 3 times, each 1 hour, united extraction liquid 60 DEG C is evaporated to without alcohol taste, obtains Herba Polygoni Capitati fluid extract 582g, and yield is 29.1%.
Make cumulative volume be 1000ml after above-mentioned obtained Herba Polygoni Capitati fluid extract is added the water suspendible of 3-4 times of volume, with the extraction into ethyl acetate of 10 times of volumes, extraction liquid 60 DEG C of concentrating under reduced pressure recycling design, obtain Ethyl acetate fraction 26.0g after evaporate to dryness.Ethyl acetate fraction carries out 100-200 order silica gel column chromatography, silica gel consumption 200g, first use 1300ml sherwood oil: the elution of ethyl acetate=2:1, use 1300ml sherwood oil again: the elution of ethyl acetate=1:1, namely obtain light green silymarin powder 10.2g after elutriant 60 DEG C of concentrating under reduced pressure evaporates to dryness, yield is 0.51%.
purity detecting and assay:adopt
embodiment 1in ultraviolet spectrophotometry purity detecting is carried out to this silymarin powder, recording its flavones lignin compound purity is 81.36%.
Adopt
embodiment 1in high performance liquid chromatography purity detecting (areas of peak normalization method) is carried out to this powder, recording silibinin purity is 66.28%.
Claims (3)
1. from Herba Polygoni Capitati herb, extract the method preparing silymarin, comprise the steps:
(1) Herba Polygoni Capitati fluid extract is prepared: after routinely dry for Herba Polygoni Capitati herb medicinal material coarse powder first being used sherwood oil heating and refluxing extraction 1-3 time of 5 times of volumes, discard extracting solution; Soak with aqueous ethanolic solution 2 times of volumes of 80%-90% volumetric concentration, 20 times of volume diacolations or 5 times of volume heating and refluxing extraction 1-3 time, extracting solution is evaporated to and obtains Herba Polygoni Capitati fluid extract without alcohol taste again;
(2) silymarin is prepared: the water suspendible above-mentioned obtained Herba Polygoni Capitati fluid extract being added 3-4 times of volume, with the extraction into ethyl acetate of 10 times of volumes, silica gel column chromatography is carried out after extraction liquid concentrating under reduced pressure evaporate to dryness, first use sherwood oil: the elution of ethyl acetate=2:1, removing low-pole impurity, use sherwood oil again: the elution of ethyl acetate=1:1, after elutriant concentrating under reduced pressure evaporate to dryness, namely obtain light green silymarin powder;
When said extracted liquid, extraction liquid or elutriant concentrating under reduced pressure, temperature is all no more than 65 DEG C.
2. the method for silymarin is prepared in the extraction from Herba Polygoni Capitati herb according to claim l, and when it is characterized in that preparing silymarin, the column chromatography silica gel of use is 100-200 order, and silica gel consumption is 7-10 times of quality of upper prop sample.
3. the method for silymarin is prepared in the extraction from Herba Polygoni Capitati herb according to claim l, when it is characterized in that preparing silymarin, uses sherwood oil: its volume of the elutriant of ethyl acetate is all no less than the silica gel amount of 6 times.
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| Title |
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| 张熙瑞等.消化系用药.《临床药物速查》.山东科学技术出版社,2003,205-206. * |
| 甘西鼠尾草及头花蓼化学成分研究;杨阳;《中国优秀硕士学位论文全文数据库 医药卫生科技辑》;20091015;第35-39、43页 * |
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