CN102010392A - Method for separating coumarin compound by using high-speed countercurrent chromatography - Google Patents
Method for separating coumarin compound by using high-speed countercurrent chromatography Download PDFInfo
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Abstract
The invention discloses a method for separating a coumarin compound by using high-speed countercurrent chromatography, which comprises the following steps of: fully mixing normal heptane, ethyl acetate, methanol and water for standing and demixing to form an upper phase which is a mobile phase and a lower phase which is a stationary phase, dissolving the primary extract of willowleaf winter-sweet into the lower phase to form a sample, filling the stationary phase into a multi-layer coil separation column, injecting the mobile phase at the rotating speed of 500 to 1,000 r/min and the flow velocity of 0.1 to 3 ml/min, performing detection by using an ultraviolet detector with the wavelength of 60 to 400 nm, feeding the sample when the mobile phase obviously flows out, simultaneously collecting effluent by using an automatic fraction collector, performing high performance liquid chromatography (HPLC) detection, mixing eluent with retention time the same as that of standard 6,7-dimethoxy coumarin and the purity of over 98 percent, and recycling a solvent by using a rotary evaporator to obtain the 6,7-dimethoxy coumarin. The method provided by the invention ensures good separation effect, low pollutions, high extraction efficiency, high purity of product, short time and fixed conditions, is convenient to operate and easy to repeat and can realize industrial production.
Description
(1) technical field
The present invention relates to medicine and biological field,, be specifically related to a kind of method of utilizing high speed adverse current chromatogram from willow leaf calyx canthus, to extract and separate coumarin kind compound about the extraction of effective components of willow leaf calyx canthus.
(2) technical background
The She nationality, distributed over Fujian, Zhejiang, Jiangxi and Guangdong's medicine is one of China's national characters medicine, and long applicating history is arranged in the She.The regional common people of the She in Zhejiang south are mainly used in epigastric fullness and chronic gastritis, the gastric and duodenal ulcer gasteremphraxis that cause, stomachache, pantothenic acid etc. of treatment due to getting ill from overeating.The bright leaf of willow leaf calyx canthus can be made tea by tealeaves fried green technology and brew and drink, and also can refine volatile oil and make tablet, dripping pill, is used for antibechic, relievings asthma, anti-curing cold and influenza.Antibiotic, anti-inflammatory, antiviral that willow leaf calyx canthus has strengthens functions such as body immunity, has no side effect, and its market and economic benefit prospect are very good.
Coumarin kind compound is extensively approval in the application aspect medical, particularly 6,7-escoparone (as shown in Equation 1), claim Scoparone, dimethoxycoumarin, escoparone, escoparone and dimethoxycoumarin again, have significant hypotensive effect and cholagogic, anti-inflammatory, analgesia, reducing blood-fat, relieving asthma, effect such as anti-freezing.Be mainly used in diseases such as treatment stenocardia, irregular pulse, bronchial asthma clinically.
Yet very few to the chemical constitution study of willow leaf calyx canthus both at home and abroad at present, isolating report when more not seeing about above-claimed cpd.Traditional separation method such as general post separation is not only consuming time, and effort, and high pollution are expensive, excessive risk.
(3) summary of the invention
The objective of the invention is to yet there are no report, and avoiding on the shortcoming basis of traditional technology and the separation method of a kind of coumarin kind compound of setting up at the extraction of the effective constituent of present willow leaf calyx canthus.
For achieving the above object, the technical solution used in the present invention is:
A kind of method of using high speed adverse current chromatogram separation coumarin kind compound, described method is: the primary extract of getting willow leaf calyx canthus is a raw material, with the high-speed countercurrent chromatography separation and Extraction, getting volume ratio is 0.1～2: 1.2: 0.5～1.5: 1.2 normal heptane, ethyl acetate, methyl alcohol, water is formed the high-speed counter-current solvent system, leave standstill after mixing fully, two-phase separately about pressing, get and be moving phase mutually, be stationary phase mutually down, ultrasonic degas, get the primary extract of willow leaf calyx canthus, be dissolved in down mutually in as trial-product, the primary extract of described willow leaf calyx canthus is 1g: 20～80ml with time mutually mass volume ratio; Stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, the setting high-speed counter current chromatograph, under 500～1000r/min rotating speed, flow velocity with 0.1～3ml/min injects moving phase, UV-detector with wavelength 60～400nm detects, when obviously having moving phase to flow out, begin to get trial-product as the sample solution sample introduction, begin simultaneously to collect effluent liquid with automatic Fraction Collector, the effluent liquid that collection is obtained detects with high performance liquid chromatography, will be with 6,7-escoparone standard substance retention time is identical and 6, and 7-escoparone purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtain 6, the 7-escoparone.
The effluent liquid that described collection obtains detects with high performance liquid chromatography, will be with 6,7, and 8-trimethoxy tonka bean camphor standard substance retention time is identical and 6,7,8-trimethoxy tonka bean camphor purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtain 6,7,8-trimethoxy tonka bean camphor.
The primary extract of described willow leaf calyx canthus is the dry thing of the sonicated extract of weak polar solvent, described institute polar solvent is one or more the mixing in water, methyl alcohol, ethanol or the ethyl acetate, and the volume ratio of the quality of the willow leaf calyx canthus primary extract that contains in the described sample solution and the multilayer coil separator column of high-speed counter-current chromatograph is 0.1～0.5: 350g/ml.
More specifically, described method comprises the steps:
(1) crosses in the willow leaf calyx canthus limb powder adding weak polar solvent of 20 mesh sieves, under frequency 20～300kHz ultrasonication, extracted 0.5～2 hour, filter then, get filtrate and be concentrated into the quality no change, drying obtains the willow leaf calyx canthus primary extract, and described weak polar solvent is one or more the mixing in water, methyl alcohol, ethanol or the ethyl acetate; The consumption of described weak polar solvent is counted 20～80mL/g with the quality of willow leaf calyx canthus limb powder;
(2) getting volume ratio is 0.1～2: 1.2: 0.5～1.5: 1.2 normal heptane, ethyl acetate, methyl alcohol, water are formed the high-speed counter-current solvent system, leave standstill after the mixing, two-phase separately about pressing, get and be moving phase mutually, be stationary phase mutually down, behind the ultrasonic degas, step (1) is obtained the willow leaf calyx canthus primary extract be dissolved in as trial-product, the primary extract of described willow leaf calyx canthus is 1g: 20～80ml with following mass volume ratio mutually;
(3) stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, the setting high-speed counter current chromatograph, under 500～1000r/min rotating speed, (preferred 0.8～3ml/min) flow velocity injects moving phase with 0.1～3ml/min, when obviously having moving phase to flow out, get trial-product as the sample solution sample introduction, begin simultaneously to collect effluent liquid with automatic Fraction Collector, the volume ratio of the quality of the willow leaf calyx canthus primary extract that contains in the described sample solution and the multilayer coil separator column of high-speed counter-current chromatograph is 0.1～0.5: 350g/mL, (preferred 210～320nm) UV-detector detects with wavelength 60～400nm, the effluent liquid that collection is obtained detects with high performance liquid chromatography, will be with 6,7-escoparone standard substance retention time is identical and 6,7-escoparone purity merges greater than 98% elutriant, reclaim solvent with Rotary Evaporators, obtain 6, the 7-escoparone; Will be with 6,7,8-trimethoxy tonka bean camphor standard substance retention time is identical and 6,7, and 8-trimethoxy tonka bean camphor purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtains 6,7,8-trimethoxy tonka bean camphor.
The concentration of willow leaf calyx canthus primary extract is preferably 0.017～0.025g/mL in the middle trial-product of described step (2).
Weak polar solvent in the described step (1) is preferably the methanol aqueous solution of volumn concentration 40～60% or the aqueous ethanolic solution of volumn concentration 40～60%.
The condition of high performance liquid chromatography is in the described step (3): chromatographic column is Agilent EclipseXDB-C18 (5um * 4.6 * 150mm).Moving phase: methyl alcohol: water (45: 55, v/v), isocratic elution.Flow velocity: 1ml/min.Column temperature: 30 ℃.Detect wavelength: 326nm.Sample size 10 μ l.
The contriver separates from willow leaf calyx canthus first and obtains natural compounds 6,7-escoparone (shown in the formula 1) and 6,7, and 8-trimethoxy tonka bean camphor (shown in the formula 2) has been filled up in the present willow leaf calyx canthus the mainly blank of coumarin kind compound extraction separation.The high speed adverse current chromatogram that the present invention utilizes adopts the liquid liquid distribution chromatography technology of on-fixed phase carrier, has good separating effect with respect to traditional separation method, pollutes little, extraction yield height, product purity height, advantage such as the time lacks, and is easy to operate.Condition of the present invention is fixed, and is easy to repetition, thereby can carry out suitability for industrialized production.Development and utilization to willow leaf calyx canthus has important use value, can effectively promote the She nationality, distributed over Fujian, Zhejiang, Jiangxi and Guangdong's medicine conservation of resources and Sustainable development to utilize again.
(4) description of drawings
Fig. 1: 6, the high performance liquid chromatography of 7-escoparone detects spectrogram.
Fig. 2: 6,7, the high performance liquid chromatography of 8-trimethoxy tonka bean camphor detects spectrogram.
(5) embodiment
With specific embodiment the present invention program is described further below, but protection scope of the present invention is not limited thereto.
Get the exsiccant willow leaf calyx canthus limb crushed material of capacity and cross 20 mesh sieves.Accurate weighing crushed material 1g adds the 20ml concentration expressed in percentage by volume and is 40% methanol aqueous solution and carries out supersound extraction, and ultrasonic time is 1h, and frequency is 20KHz.Gained solution filters, and gets filtrate and is concentrated into the quality no change, and the room temperature primary extract of placing dry willow leaf calyx canthus that ventilates is standby.
The separation and Extraction of high speed adverse current chromatogram, (volume ratio is 0.1: 1.2: 1.5: 1.2), left standstill 4 hours after mixing fully to add normal heptane, ethyl acetate, methyl alcohol, water in separating funnel, two-phase separately about pressing, on be moving phase mutually, is stationary phase mutually down, 20KHz ultrasonic degas 20min.Take by weighing the primary extract 0.1g of willow leaf calyx canthus, be dissolved under the 8ml mutually, obtain trial-product, as sample solution.
Stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, the column volume of separator column is 350ml, the setting high-speed counter current chromatograph, when instrument reaches balance with stable rotation of 500r/min and two-phase, pump into moving phase with 3ml/min, when obviously having moving phase to flow out, inject sample solution, begin simultaneously to collect effluent liquid with automatic Fraction Collector, gathering speed is 3min/tube, the detection wavelength of UV-detector is 210nm, the effluent liquid that collection is obtained detects with high performance liquid chromatography, will be with 6, and 7-escoparone standard substance retention time (3.77min) are identical and 6,7-escoparone purity merges greater than 98% elutriant, reclaim solvent with Rotary Evaporators, obtain 6,7-escoparone 5.53mg, purity is 98%, and the rate of recovery is 92%; Will be with 6,7,8-trimethoxy tonka bean camphor standard substance retention time (5.15min) are identical and 6,7,8-trimethoxy tonka bean camphor purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtains 6,7,8-trimethoxy tonka bean camphor 3.33mg, purity is 98%, the rate of recovery is 90%.
High-efficient liquid phase chromatogram condition: chromatographic column is Agilent Eclipse
XDB-C18(5um×4.6×150mm)。Moving phase: methyl alcohol: water (45: 55), isocratic elution.Flow velocity: 1ml/min.Column temperature: 30 ℃.Detect wavelength: 326nm.Sample size 10 μ l.
Get the exsiccant willow leaf calyx canthus limb crushed material of capacity and cross 20 mesh sieves.Accurate weighing crushed material 1g adds the 30ml concentration expressed in percentage by volume and is 60% aqueous ethanolic solution and carries out supersound extraction, and ultrasonic time is 0.5h, and frequency is 300KHz.Gained solution filters, and gets filtrate and is concentrated into the quality no change, and the room temperature primary extract of placing dry willow leaf calyx canthus that ventilates is standby.
The separation and Extraction of high speed adverse current chromatogram, (volume ratio is 2: 1.2: 0.5: 1.2), left standstill 3 hours after mixing fully to add normal heptane, ethyl acetate, methyl alcohol, water in separating funnel, two-phase separately about pressing, on be moving phase mutually, is stationary phase mutually down, 300KHz ultrasonic degas 20min.Take by weighing the primary extract 0.4g of willow leaf calyx canthus, be dissolved under the 15ml mutually, obtain trial-product, as sample solution.
Stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, the column volume of separator column is 350ml, the setting high-speed counter current chromatograph, when instrument reaches balance with stable rotation of 1000r/min and two-phase, pump into moving phase with 0.8ml/min, when obviously having moving phase to flow out, inject sample solution, begin simultaneously to collect effluent liquid with automatic Fraction Collector, gathering speed is 5min/tube, the detection wavelength of UV-detector is 260nm, the effluent liquid that collection is obtained detects with high performance liquid chromatography, will be with 6, and 7-escoparone standard substance retention time (3.77min) are identical and 6,7-escoparone purity merges greater than 98% elutriant, reclaim solvent with Rotary Evaporators, obtain 6,7-escoparone 22mg, purity is 98%, and the rate of recovery is 89%; Will be with 6,7,8-trimethoxy tonka bean camphor standard substance retention time (5.15min) are identical and 6,7,8-trimethoxy tonka bean camphor purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtains 6,7,8-trimethoxy tonka bean camphor 13.2mg, purity is 98%, the rate of recovery is 91%.
High-efficient liquid phase chromatogram condition: chromatographic column is Agilent Eclipse
XDB-C18(5um×4.6×150mm)。Moving phase: methyl alcohol: water (45: 55), isocratic elution.Flow velocity: 1ml/min.Column temperature: 30 ℃.Detect wavelength: 326nm.Sample size 10 μ l.
Embodiment 3
Get the exsiccant willow leaf calyx canthus limb crushed material of capacity and cross 20 mesh sieves.Accurate weighing crushed material 1g adds the 50ml concentration expressed in percentage by volume and is 55% methanol aqueous solution and carries out supersound extraction, and ultrasonic time is 2h, and frequency is 60KHz.Gained solution filters, and gets filtrate and is concentrated into the quality no change, and the room temperature primary extract of placing dry willow leaf calyx canthus that ventilates is standby.
The separation and Extraction of high speed adverse current chromatogram, (volume ratio is 1: 1.2: 0.6: 1.2), left standstill 6 hours after mixing fully to add normal heptane, ethyl acetate, methyl alcohol, water in separating funnel, two-phase separately about pressing, on be moving phase mutually, is stationary phase mutually down, 60KHz ultrasonic degas 20min.Take by weighing the primary extract 0.3g of willow leaf calyx canthus, be dissolved under the 13ml mutually, obtain trial-product, as sample solution.
Stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, the column volume of separator column is 350ml, the setting high-speed counter current chromatograph, when instrument reaches balance with stable rotation of 900r/min and two-phase, pump into moving phase with 2ml/min, when obviously having moving phase to flow out, inject sample solution, begin simultaneously to collect effluent liquid with automatic Fraction Collector, gathering speed is 2min/tube, the detection wavelength of UV-detector is 320nm, the effluent liquid that collection is obtained detects with high performance liquid chromatography, will be with 6, and 7-escoparone standard substance retention time (3.77min) are identical and 6,7-escoparone purity merges greater than 98% elutriant, reclaim solvent with Rotary Evaporators, obtain 6,7-escoparone 16.6mg, purity is 98%, and the rate of recovery is 88%; Will be with 6,7,8-trimethoxy tonka bean camphor standard substance retention time (5.15min) are identical and 6,7,8-trimethoxy tonka bean camphor purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtains 6,7,8-trimethoxy tonka bean camphor 10.5mg, purity is 98%, the rate of recovery is 91%.
High-efficient liquid phase chromatogram condition: chromatographic column is Agilent Eclipse
XDB-C18(5um×4.6×150mm)。Moving phase: methyl alcohol: water (45: 55), isocratic elution.Flow velocity: 1ml/min.Column temperature: 30 ℃.Detect wavelength: 326nm.Sample size 10 μ l.
Claims (6)
1. use the method that high speed adverse current chromatogram separates coumarin kind compound for one kind, it is characterized in that described method is: the primary extract of getting willow leaf calyx canthus is a raw material, with the high-speed countercurrent chromatography separation and Extraction, get the normal heptane that volume ratio is 0.1～2:1.2:0.5～1.5:1.2, ethyl acetate, methyl alcohol, water is formed the high-speed counter-current solvent system, leave standstill after mixing fully, two-phase separately about pressing, get and be moving phase mutually, be stationary phase mutually down, ultrasonic degas, get the primary extract of willow leaf calyx canthus, be dissolved in down mutually in as trial-product, the primary extract of described willow leaf calyx canthus is 1g:20～80 ml with time mutually mass volume ratio; Stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, the setting high-speed counter current chromatograph, under 500～1000r/min rotating speed, flow velocity with 0.1～3ml/min injects moving phase, UV-detector with wavelength 60～400nm detects, when obviously having moving phase to flow out, begin to get trial-product as the sample solution sample introduction, begin simultaneously to collect effluent liquid with automatic Fraction Collector, the effluent liquid that collection is obtained detects with high performance liquid chromatography, will be with 6,7-escoparone standard substance retention time is identical and 6, and 7-escoparone purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtain 6, the 7-escoparone;
The primary extract of described willow leaf calyx canthus is the dry thing of the sonicated extract of weak polar solvent, described institute polar solvent is one or more the mixing in water, methyl alcohol, ethanol or the ethyl acetate, and the volume ratio of the quality of the willow leaf calyx canthus primary extract that contains in the described sample solution and the multilayer coil separator column of high-speed counter-current chromatograph is 0.1～0.5:350g/ml.
2. the method for claim 1, it is characterized in that the effluent liquid that described collection obtains detects with high performance liquid chromatography, will be with 6,7,8-trimethoxy tonka bean camphor standard substance retention time is identical and 6,7,8-trimethoxy tonka bean camphor purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtains 6,7,8-trimethoxy tonka bean camphor.
3. high speed adverse current chromatogram as claimed in claim 1 or 2 separates the method for coumarin kind compound, it is characterized in that described method comprises the steps:
(1) crosses in the willow leaf calyx canthus limb powder adding weak polar solvent of 20 mesh sieves, under frequency 20 ~ 300kHz ultrasonication, extracted 0.5 ~ 2 hour, filter then, get filtrate and be concentrated into the quality no change, drying obtains the willow leaf calyx canthus primary extract, and described weak polar solvent is one or more the mixing in water, methyl alcohol, ethanol or the ethyl acetate; The consumption of described weak polar solvent is counted 20 ~ 80mL/g with the quality of willow leaf calyx canthus limb powder;
(2) get normal heptane, ethyl acetate, methyl alcohol, the water that volume ratio is 0.1～2:1.2:0.5～1.5:1.2 and form the high-speed counter-current solvent system, leave standstill after the mixing, two-phase separately about pressing, get and be moving phase mutually, be stationary phase mutually down, behind the ultrasonic degas, step (1) is obtained the willow leaf calyx canthus primary extract be dissolved in part down as trial-product, the primary extract of described willow leaf calyx canthus is 1g:20～80 ml with following mass volume ratio mutually;
(3) stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, the setting high-speed counter current chromatograph, under 500～1000r/min rotating speed, flow velocity with 0.1～3ml/min injects moving phase, when obviously having moving phase to flow out, get trial-product as the sample solution sample introduction, begin simultaneously to collect effluent liquid with automatic Fraction Collector, the volume ratio of the quality of the willow leaf calyx canthus primary extract that contains in the described sample solution and the multilayer coil separator column of high-speed counter-current chromatograph is 0.1～0.5:350 g/mL, UV-detector with wavelength 60～400nm detects, the effluent liquid that collection is obtained detects with high performance liquid chromatography, will be with 6,7-escoparone standard substance retention time is identical and 6,7-escoparone purity merges greater than 98% elutriant, reclaim solvent with Rotary Evaporators, obtain 6, the 7-escoparone; Will be with 6,7,8-trimethoxy tonka bean camphor standard substance retention time is identical and 6,7, and 8-trimethoxy tonka bean camphor purity merges greater than 98% elutriant, reclaims solvent with Rotary Evaporators, obtains 6,7,8-trimethoxy tonka bean camphor.
4. method as claimed in claim 3 is characterized in that the concentration of willow leaf calyx canthus primary extract in the middle trial-product of described step (2) is 0.017 ~ 0.025g/mL.
5. method as claimed in claim 3 is characterized in that the weak polar solvent in the described step (1) is the methanol aqueous solution of volumn concentration 40 ~ 60% or the aqueous ethanolic solution of volumn concentration 40 ~ 60%.
6. method as claimed in claim 3, it is characterized in that the condition of high performance liquid chromatography in the described step (3) is: chromatographic column is Agilent Eclipse XDB-C18 (5um * 4.6 * 150mm); Moving phase: methyl alcohol: water (45:55, v/v); Isocratic elution; Flow velocity: 1ml/min; Column temperature: 30 ℃; Detect wavelength: 326nm; Sample size 10 μ l.
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| CN102584761A (en) * | 2011-12-29 | 2012-07-18 | 浙江工业大学 | Method for extracting total coumarins compound from chimonanthus salicifolius |
| CN112898258A (en) * | 2021-03-05 | 2021-06-04 | 中国科学院兰州化学物理研究所 | Separation preparation method of high-purity hyoscyamine |
| CN114456138A (en) * | 2022-03-07 | 2022-05-10 | 金华高等研究院(金华理工学院筹建工作领导小组办公室) | Method for separating three coumarin compounds from fingered citron extract |
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| CN101735187A (en) * | 2009-12-25 | 2010-06-16 | 浙江工业大学 | Method for extracting coumarin compound from willow leaf calyx canthus |
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| CN101735187A (en) * | 2009-12-25 | 2010-06-16 | 浙江工业大学 | Method for extracting coumarin compound from willow leaf calyx canthus |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584761A (en) * | 2011-12-29 | 2012-07-18 | 浙江工业大学 | Method for extracting total coumarins compound from chimonanthus salicifolius |
| CN112898258A (en) * | 2021-03-05 | 2021-06-04 | 中国科学院兰州化学物理研究所 | Separation preparation method of high-purity hyoscyamine |
| CN112898258B (en) * | 2021-03-05 | 2023-01-03 | 中国科学院兰州化学物理研究所 | Separation preparation method of high-purity hyoscyamine |
| CN114456138A (en) * | 2022-03-07 | 2022-05-10 | 金华高等研究院(金华理工学院筹建工作领导小组办公室) | Method for separating three coumarin compounds from fingered citron extract |
| CN114456138B (en) * | 2022-03-07 | 2024-06-04 | 金华高等研究院(金华理工学院筹建工作领导小组办公室) | Method for separating three coumarin compounds from fingered citron extract |
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