CN1634875A - Process for rapid preparation of high pure pharmaceutical matters from patrinia villosa juss - Google Patents
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- CN1634875A CN1634875A CN 200410068016 CN200410068016A CN1634875A CN 1634875 A CN1634875 A CN 1634875A CN 200410068016 CN200410068016 CN 200410068016 CN 200410068016 A CN200410068016 A CN 200410068016A CN 1634875 A CN1634875 A CN 1634875A
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- saponaretin
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Abstract
The invention provides a rapid preparation method of some high pure pharmaceutical matter of patrinia villosa juss. The process comprises : (1) extraction of medical materials; (2) preparation of crude extract; (3) separation and purification of obtained crude extract by high-speed countercurrent chromatography, comprising solvent system for stationary phase and mobile phase, filling stationary phase in countercurrent chromatographic column, running the column, pumping the mobile phase into column, injecting sample via injection valve, and receiving the demanded components according to the detection spectrogram, wherein, the said two phase solvent system is composed of n-hexane, ethyl acetate, methanol, water and ethyl acetate, n-butyl alcohol, water.
Description
Technical field
The separation purification method of pharmaceutically active ingredient in the present invention relates to, more particularly, that the present invention relates to is the golden acid amides alcohol ester of high purity, Lutonaretin and Saponaretin high speed adverse current chromatogram sharp separation preparation method in the patrima villosa grass.
Background technology
Patrima villosa grass (Patrinia Villosa Juss) has another name called bitter dish, bitter vegetarian, deer intestines, is the Valerianaceae per nnial herb, is distributed in China East China, Central China, south China and southwestern various places.Contain useful compositions such as multiple amino acids, VITAMIN and mineral substance because of it extensively edible by people, it also is a kind of conventional Chinese medicine, beginning is stated from " Dragon Lord book on Chinese herbal medicine warp ", after again by " Chinese pharmacopoeia (1977 editions) is recorded, have clearing heat and promoting diuresis, detoxify and drain pus, promoting blood circulation and removing blood stasis, clearing away the heart fire and tranquillizing, promotion liver cell regeneration, improve liver function, strengthen effects such as antibacterial and antiviral, be usually used in treating diseases such as ecphyaditis, dysentery, hepatitis, tonsillitis, mumps, carbuncle is swollen clinically.Modern study shows that the patrima villosa grass mainly contains triterpenes and iridoid such as villosolside (villosolside), villosol (villosol), Semen Momordicae glucoside (loganin), Morroniside (morroniside), villoside (villoside) etc., also has volatile oil in addition based on patrinene and isopatrinene, lactone, tonka bean camphor etc., but much do not see bibliographical information, do not see relevant patent yet, more do not see to have and separate the golden acid amides alcohol ester that obtains having multiple pharmacologically active from the patrima villosa grass, Lutonaretin and Saponaretin [F.U.Afifi, E.Khalil, S.Abdalla, Journal of Ethnopharmacology, 65 (1999), 173-177; Didem Deliorman Orhan, Mustafa Alsan, Goknur Aktay ect, LifeScience, 72 (2003), 2273-2283.] report, their structural formula is as follows:
Golden acid amides alcohol ester
Lutonaretin
Saponaretin
Adopt the effective monomer in traditional method for separating and preparing separating plant such as column chromatography and recrystallization, waste time and energy, contaminate environment [C.L Ky, M.Noirot, S.Hamon, J.Agric.Food.Chem.1997,45:786; W.M.Yan, Acta Botanica Sinica, 1979,20:54; J.J Liu, G.L.Zhao, H.Wang, X.H.Zhang, J.Cent.South.Univ.T.2002,9:246], and used stationary phase has weak points such as non-reversibility adsorption to sample.
Summary of the invention
Therefore, people solve the problems referred to above to the isolation technique that adopts better effects and if have demand.
The purpose of this invention is to provide a kind of from the patrima villosa grass method of the golden acid amides alcohol ester of separating and purifying high-purity, Lutonaretin and Saponaretin, to overcome the above-mentioned problems in the prior art.
High speed adverse current chromatogram (High-speed counter-current chromatography HSCCC) is a kind of newer liquid liquid distribution chromatography technology, it need not any solid support or carrier and overcome the non-reversibility adsorption of traditional separation method to sample, thereby sample recovery rate height, also have advantages such as applied range, instrumentation is simple, fractional dose is big simultaneously, therefore be widely used in the middle of the separation preparation of natural product.
Provided by the invention from the patrima villosa grass the golden acid amides alcohol ester of separating and purifying high-purity, the method of Lutonaretin and Saponaretin specifically comprises: medicinal material extract, the separation and purification three process of crude extract preparation and crude extract, it is characterized in that operation (1) adopts Different concentrations of alcohol to extract medicinal material successively and obtains extract, operation (2) adopts organic solvent that extract stage extraction and binding silica gel column chromatography are obtained crude extract, operation (3) adopts high-speed countercurrent chromatography that crude extract is carried out separation and purification, it comprises that preparation constitutes stationary phase, the solvent system of moving phase, make in the counter current chromatograph pillar and be full of stationary phase, pillar is rotated, again moving phase is pumped in the post, enter the crude extract sample for preparing by sampling valve, according to detecting collection of illustrative plates receiving target component.
1. medicinal material extract
After getting the suitable pulverizing of patrima villosa medicinal material, use 40% alcohol reflux earlier, the dregs of a decoction after the filtration are used 95% alcohol reflux again, united extraction liquid, and being evaporated to does not have pure the flavor.
2. the position obtains
Get and extract gained medicinal extract, add the suitable quantity of water suspendible after, use petroleum ether extraction earlier, static branch is got petroleum ether layer, adds n-butanol extraction again in water layer, static back branch is got n-butanol layer, concentrating under reduced pressure sherwood oil and n-butyl alcohol extract, vacuum-drying.
Get petroleum ether extract and carry out silica gel column chromatography,, receive sherwood oil with petroleum ether-ethyl acetate tonsure wash-out: ethyl acetate (5: 1) wash-out stream part, as further separation and purification sample.
3. the separation and purification at position
Use the high speed adverse current chromatogram separation and purification, it comprises that step (1) preparation constitutes the solvent system of stationary phase, moving phase, make in the counter current chromatograph pillar and be full of stationary phase, pillar is rotated, again moving phase is pumped in the post, by the sampling valve sample introduction, according to detecting spectrogram receiving target composition, (2) silicagel column of petroleum ether extract just divides thing solvent for use system to be made up of normal hexane, ethyl acetate, methyl alcohol, water, and (3) n-butyl alcohol extract solvent for use system is made up of ethyl acetate, propyl carbinol, water.
Wherein the amount ratio of normal hexane, ethyl acetate, methyl alcohol, water is 1: 1: 1: 1, and the amount ratio of ethyl acetate, propyl carbinol, water is 2: 1: 3.
4. the purity detecting of isolate and structure are identified
Adopt high performance liquid chromatography to carry out purity detecting (peak area normalization method) to getting component, volatilize carry out behind the solvent MS,
1HNMR and
13CNMR analyzes, and carries out structural confirmation according to the gained data.
The present invention adopts high speed adverse current chromatogram that the Chinese medicine crude extract is carried out separation and purification, and is easy, quick, also avoided sample loss simultaneously.Overcome shortcomings such as traditional preparation process method complex operation, separation cycle be long, and have that preparation amount is big, separation efficiency is high, good product purity, advantage such as simple and easy to do, be easy to promote the use of.
Description of drawings
Fig. 1 is the color atlas of half countercurrent chromatography (HSCCC) of petroleum ether extract
Fig. 2 is the color atlas of half countercurrent chromatography (HSCCC) of n-butyl alcohol extract
Fig. 3 is for being the color atlas of the high performance liquid chromatography (HPLC) of sherwood oil and propyl carbinol crude extract and each separate part
Embodiment
The present invention will be described below in conjunction with specific embodiment and accompanying drawing
Embodiment 1:
1. take by weighing patrima villosa herbal medicine material meal 6.0kg, with 10 times of amount 40% alcohol reflux twice, each 1.5h, filter, in filter residue, add 8 times of amount 95% ethanol refluxing extraction 2 times once more, each 1.5h, filter, merging filtrate is evaporated to the about 2000ml of medicinal extract.
2. get the medicinal extract after concentrating, add 1000ml water suspendible after, place the 5000ml separating funnel, add static layering behind the sherwood oil 1000ml shake well, divide and get petroleum ether layer, so extract three times, merge petroleum ether extraction liquid.Add the 1000ml propyl carbinol again in water layer, static layering behind the shake well is divided and is got n-butanol layer, so extracts three times, merges butanol extraction liquid.Concentrating under reduced pressure extraction liquid (thickening temperature 60 degree) back drying under reduced pressure gets petroleum ether extract 150g, n-butyl alcohol extract 25g.
3. get petroleum ether extract 150g and carry out silica gel column chromatography (8.0 * 120cm, silica gel amount 2500g, the 200-300 order), use sherwood oil successively: ethyl acetate (20: 1-1: 1) tonsure wash-out, receive sherwood oil: ethyl acetate (5: 1) elutriant, behind the concentrating under reduced pressure, vacuum-drying (60 ℃) gets amount of solid 600mg.
4. the silicagel column of using high speed adverse current chromatogram (Shenzhen is with the biochemical company limited in field) separation and purification petroleum ether extract just divides thing and n-butyl alcohol extract.
(1) silicagel column of petroleum ether extract just divides the high speed adverse current chromatogram separation and purification of thing
Solvent system and consumption volume ratio are normal hexane: ethyl acetate: methyl alcohol: water=1: 1: 1: 1, the adverse current chromatogram column volume is 300ml, applied sample amount 600mg, rotating speed 800rpm, on be stationary phase mutually, is moving phase mutually down, flow velocity 2.0ml/min, stationary phase retention rate 54% detects wavelength 254nm, and Ji Lu color atlas is seen Fig. 1 in the case.
Concrete operation steps is: than the preparation solvent system, static layering behind the shake well in separating funnel is divided and is got phase up and down by above-mentioned solvent volume, on be stationary phase mutually, under be moving phase mutually.Make earlier in the counter current chromatograph pillar to be full of stationary phase, main frame is rotated, pump into moving phase again, by the sampling valve sample introduction, according to detector spectrogram receiving target composition, result's separation obtains 1 part, i.e. stream part " I ".
This part is carried out high-efficient liquid phase analysis show that " I " is single chromatographic peak, peak purity is 99.2%.
(2) the high speed adverse current chromatogram separation and purification of n-butyl alcohol extract
Solvent system and consumption volume ratio are ethyl acetate: propyl carbinol: water=2: 1: 3, the adverse current chromatogram column volume is 300ml, applied sample amount 250mg, rotating speed 800rpm, on be stationary phase mutually, is moving phase mutually down, flow velocity 2.0ml/min, stationary phase retention rate 49% detects wavelength 254nm, and Ji Lu color atlas is seen Fig. 2 in the case.
Concrete operation steps is with (1), and result's separation obtains 2 parts, i.e. " II " and " III ".
These two portions are carried out high-efficient liquid phase analysis show that " II " and " III " is single chromatographic peak, peak purity is respectively 98.3% and 99.1%.
HPLC analysis condition: chromatographic column Lichrospher C18 (6.0 * 150mmi.d.5 μ m),
The silicagel column of petroleum ether extract just divides thing: moving phase is CH
3CN: H
2O: HAC=70: 30: 1, flow velocity 1.0ml/min detected wavelength 254mn, and the silicagel column of petroleum ether extract just divides thing and HSCCC separate part color atlas to see Fig. 3 with this understanding.N-butyl alcohol extract: moving phase is CH
3CN: H
2O: HAC=20: 80: 1, flow velocity 1.0ml/min detected wavelength 254nm, and the color atlas of n-butyl alcohol extract and each separate part is seen Fig. 3 with this understanding.Wherein Fig. 3-1 looks for spectrogram for the silicagel column of petroleum ether extract first the branch, Fig. 3-2 just divides HSCCC separate part (the golden acid amides alcohol ester) color atlas of thing for the silicagel column of petroleum ether extract, Fig. 3-3 is the n-butyl alcohol extract color atlas, Fig. 3-4 is the Lutonaretin color atlas, Fig. 3-5 is the Saponaretin color atlas, peak 1 is golden acid amides alcohol ester, and peak 2 is a Lutonaretin, and peak 3 is a Saponaretin.
Structure is identified: golden acid amides alcohol ester, Lutonaretin and Saponaretin that separation is obtained carry out on VarianINOVA-500 type nuclear magnetic resonance analyser and Varian MAT-212 type mass spectrograph
1HNMR,
13CNMR and MS analyze, and the gained data are as follows.
Golden acid amides alcohol ester white, needle-shaped crystals (ethyl acetate), UV λ max (nmMeOH): 254nm.TOF-MS：467.16[M+Na]
+，911.29[2M+Na]。HR-TOF/MS:444.1947, molecular formula is C
27H
28N
2O
4 13CNMR (500MHz, DMSO-d
6) δ: 166.03,170.14,171.05 is three carbonyl carbon signals, three quaternary carbon signals (138.21,137.92,134.01), 15 are in low and symmetric methyne signal (131.16～126.11), two methine carbon signals (54.76,49.06) that are in high field, three mesomethylene carbon signals (64.54,37.16,36.52), a methyl carbon signal (20.50).
1HNMR (500MHz, DMSO-d
6) in, δ 8.25 (d, J=8.5Hz) and 7.91 (d, J=8.1Hz) the H signal for connecting on the N atom, δ 7.87～7.12 is 15 symmetric aryl proton signals, δ 4.82 and 4.30 is two methine protons signals, and δ 3.15,3.09,4.55,3.98,2.84 is a proton signal on the mesomethylene carbon.
The Lutonaretin yellow powder, UV λ max (nm MeOH): 348,270,255.TOF-MS：447[M+1]
-，895[2M-1]
-，471[M+Na]
+，919[2?M+Na]
+，449[M+1]
+，487[M+K]
+。
1HNMR(500MHz，DMSO-d
6)δ：13.55(1H，brs，5-OH)，7.44(1H，dd，J＝2.5Hz，9.0Hz，6′-H)，7.38(1H，d，J＝2.5Hz，2′-H)，6.90(1H，d，J＝9.0Hz，5′-H)，6.64(1H，S，3-H)，4.58(1H，d，J＝10.0Hz，1″-H)。
13CNMR(500MHz，DMSO-d
6)δ：163.44(C-2)，102.38(C-3)，181.45(C-4)，160.59(C-5)，108.88(C-6)，163.44(C-7)，93.73(C-8)，156.27(C-9)，102.79(C-10)，121.56(C-1′)，112.92(C-2′)，145.95(C-3′)，150.44(C-4′)，116.00(C-5′)，118.82(C-6′)，73.18(C-1″)，70.50(C-2″)，78.95(C-3″)，70.19(C-4″)，81.35(C-5″)，61.34(C-6″)。
The Saponaretin yellow powder, UV λ max (nm MeOH): 334,270,302i.TOF-MS：455[M+Na]
+，433[M+1]
+，471[M+K]
+，887[2M+Na]
+，903[2M+K]
+。
1HNMR(500MHz，DMSO-d
6)δ：13.46(1H，brs，5-OH)，7.85(2H，d，J＝8.5Hz，3′，5′-H)，6.94(2H，d，J＝8.4Hz，2′，6′-H)，6.71(1H，s，3-H)，6.42(1H，s，8-H)，4.56(1H，d，J＝9.8Hz，1″-H)。
13CNMR(500MHz，DMSO-d
6)δ：163.32(C-2)，102.60(C-3)，181.73(C-4)，160.64(C-5)，108.95(C-6)，163.32(C-7)，93.79(C-8)，156.31(C-9)，102.95(C-10)，121.00(C-1′)，128.35(C-2′，6′)，116.01(C-3′，5′)，161.32(C-4′)，73.13(C-1″)，70.52(C-2″)，78.93(C-3″)，70.20(C-4″)，81.38(C-5″)，61.37(C-6″)。
Claims (8)
1. golden acid amides alcohol ester of separating and purifying high-purity from the patrima villosa grass, the method of Lutonaretin and Saponaretin, specifically comprise: medicinal material extract, the separation and purification three process of crude extract preparation and crude extract, it is characterized in that operation (1) adopts Different concentrations of alcohol to extract medicinal material successively and obtains extract, operation (2) adopts organic solvent that extract stage extraction and binding silica gel column chromatography are obtained crude extract, operation (3) adopts high-speed countercurrent chromatography that crude extract is carried out separation and purification, it comprises that preparation constitutes stationary phase, the solvent system of moving phase, make in the counter current chromatograph pillar and be full of stationary phase, pillar is rotated, again moving phase is pumped in the post, enter the crude extract sample for preparing by sampling valve, according to detecting collection of illustrative plates receiving target component.
According to claim 1 described a kind of from the patrima villosa grass method of the golden acid amides alcohol ester of separating and purifying high-purity, Lutonaretin and Saponaretin, it is characterized in that the middle different concentration ethanol of operation (1) is 40% and 95% medicinal alcohol, earlier with using 95% extraction using alcohol again behind the 40% extraction using alcohol medicinal material, united extraction liquid is evaporated to medicinal extract
According to claim 1 described a kind of from the patrima villosa grass method of the golden acid amides alcohol ester of separating and purifying high-purity, Lutonaretin and Saponaretin, it is characterized in that the used organic solvent of extracting solution extraction is sherwood oil (60-90 ℃) and propyl carbinol in the operation (2), use earlier petroleum ether extraction, use n-butanol extraction again, obtain sherwood oil and n-butyl alcohol extract.
According to claim 1 or 3 described a kind of from the patrima villosa grass method of the golden acid amides alcohol ester of separating and purifying high-purity, Lutonaretin and Saponaretin, it is characterized in that petroleum ether extract at first carries out silicagel column and just divides, with petroleum ether-ethyl acetate tonsure wash-out, receive sherwood oil: ethyl acetate (5: 1) wash-out stream part, as further separation and purification sample.
According to claim 1 described a kind of from the patrima villosa grass method of the golden acid amides alcohol ester of separating and purifying high-purity, Lutonaretin and Saponaretin, it is characterized in that adopting high-speed countercurrent chromatography that the gained crude extract is carried out separation and purification, used two-phase solvent system is a normal hexane in the high-speed countercurrent chromatography of the silicagel column isolate of petroleum ether extract: ethyl acetate: methyl alcohol: water.
According to claim 1 or 5 described a kind of from the patrima villosa grass method of the golden acid amides alcohol ester of separating and purifying high-purity, Lutonaretin and Saponaretin, it is characterized in that solvent for use system normal hexane in the high-speed countercurrent chromatography: ethyl acetate: methyl alcohol: the best proportioning of water is 1: 1: 1: 1, on be stationary phase mutually, is moving phase mutually down.
According to claim 1 or 3 described a kind of from the patrima villosa grass method of the golden acid amides alcohol ester of separating and purifying high-purity, Lutonaretin and Saponaretin, it is characterized in that it is ethyl acetate that high-speed countercurrent chromatography to the n-butanol portion crude extract carries out the used two-phase solvent system of separation and purification: propyl carbinol: water.
According to claim 1 or 7 described a kind of from the patrima villosa grass method of the golden acid amides alcohol ester of separating and purifying high-purity, Lutonaretin and Saponaretin, it is characterized in that used two-phase solvent system ethyl acetate in the high-speed countercurrent chromatography: propyl carbinol: the best proportioning of water is 2: 1: 3, on be stationary phase mutually, is moving phase mutually down.
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| CN100434135C (en) * | 2005-09-23 | 2008-11-19 | 中国科学院过程工程研究所 | Method for separating and purifying natural product using three-phase counter current chromatograph |
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| CN105859700A (en) * | 2016-04-26 | 2016-08-17 | 中国广州分析测试中心 | Method for extracting and preparing isovitexin from patrinia villosa juss |
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| CN103508922B (en) * | 2012-06-25 | 2015-06-17 | 复旦大学 | Dipeptide compound and use of the same in preparation of anti-complement drugs |
| CN103417589A (en) * | 2013-08-26 | 2013-12-04 | 重庆工商大学 | Preparation method and application of patrinia villosa root extractive |
| CN103405484A (en) * | 2013-08-26 | 2013-11-27 | 重庆工商大学 | Preparation method of patrinia villosa root anti-oxidization preparation |
| CN104592798A (en) * | 2014-12-29 | 2015-05-06 | 岭南师范学院 | Application of aurantiamide acetate in preventing and removing marine fouling organisms |
| CN105859700A (en) * | 2016-04-26 | 2016-08-17 | 中国广州分析测试中心 | Method for extracting and preparing isovitexin from patrinia villosa juss |
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| CN109053835A (en) * | 2018-08-13 | 2018-12-21 | 黄斌 | A kind of extraction of sowthistle-leaf ixeris seedling flavonoid glycoside and its purification process |
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