CN103304490B - Method for separating and purifying five purine and pyrimidine bases from trichosanthes bark - Google Patents
Method for separating and purifying five purine and pyrimidine bases from trichosanthes bark Download PDFInfo
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Abstract
The invention relates to a method for separating and purifying five purine and pyrimidine bases (namely cytosine, uracil, hypoxanthine, guanine and xanthine) from trichosanthes bark. According to the method, five high-purity monomeric compounds, namely cytosine, uracil, hypoxanthine, guanine and xanthine, are obtained from the trichosanthes bark through the following steps of: (1) preparing a crude trichosanthes bark extract; (2) carrying out crude separation by using a macroporous adsorption resin column; and (3) carrying out separation and purification by using semi-preparative high-performance liquid chromatography: carrying out separation and purification on a sample 1 and a sample 2 by using the semi-preparative high-performance liquid chromatography, wherein the mobile phase is methanol-water. The method disclosed by the invention has the advantages that the process flow is environment-friendly, the damage to the environment is not serious, and the comprehensive cost is low.
Description
Technical field
The invention belongs to chemical field, specifically relate to a kind of method of separation and purification 5 kinds of purine and pyrimidine bases (cytosine(Cyt), uridylic, xanthoglobulin, guanine and xanthine) from Chinese medicine Snakegourd Peel.
Background technology
Snakegourd Peel be Curcurbitaceae Trichosanthes snakegourd (
trichosanthes kirilowiimarim.) or trichosanthes rosthornii Harms (
trichosanthes rosthorniiharms.) dry mature skin, belongs to conventional Chinese medicine, has the effect such as moistening the lung and resolving the phlegm, the wide chest of sharp gas, is widely used in the diseases such as treatment phlegm heat cough, the turbid Huang of phlegm are thick, pharyngalgia, pectoralgia, haematemesis, bleeding from five sense organs or subcutaneous tissue, constipation, carbuncle pyogenic infections from tumour or sore clinically.Modern pharmacology experiment and clinical practice show that Snakegourd Peel has coronary artery dilator, increases coronary flow, improves myocardial hypoxia tolerance, reduces serum cholesterol, the multiple pharmacological effect such as antibacterial, anticancer, especially have good therapeutic action to cardiovascular disorder.
Nucleic acid contains biological heredity information, purine, miazines Biological Base are the important component parts forming nucleic acid, the multiple vital movements such as wide participation heredity and metabolism, their metabolic disturbance often causes many serious diseases, as renal failure, gout and male sterility etc.Xanthoglobulin is a kind of very important biological purine bases, there is reducing blood pressure, relieving asthma, treat the pharmacologically actives such as gout, widely distributed in human body, can participate in regulating some the important physiological functions in human body, also can be used for treating the disease such as leukopenia, thrombocytopenia caused by a variety of causes, also report that the growth metabolism of xanthine, xanthoglobulin and tumour cell is in close relations abroad.
The now method of existing bibliographical information extraction purification purine and miazines Biological Base from Snakegourd Peel.Teng Yongrong [Snakegourd Peel and Pericarpium Trichosanthis injection chemical constitution study, Shandong Traditional Chinese Medicine University's master thesis, 2011] utilize repeatedly the chemical compositions of separation means to Snakegourd Peel such as silica gel column chromatography, macroporous adsorbent resin column chromatography and preparative high performance liquid chromatography to be studied, obtain 7 compounds altogether, comprising 3 gradient elutions (the different inosine of VITAMIN B4, guanosine-and 6-).Shi Yanpeng [research of snakegourd chemical composition and the assay (I) of hitodesterol thereof, herbal medicine, 1 phase in 2002] utilize repeatedly the chemical composition of silica gel column chromatography to snakegourd to be studied, be separated obtain 12 compounds from petroleum ether part, chloroform extract, n-butanol portion, wherein 10 obtain qualification, comprise a kind of gradient elution-uridylic.Liu Dailin [the platelet aggregation inhibitory activity composition Study of Snakegourd Fruit. herbal medicine, 12 phases in 2004] utilize the tracking activity method of platelet aggregation-against, adopt Sephadex LH-20 column chromatography and silica gel column chromatography separation repeatedly, be separated in Snakegourd Fruit and obtain 7 compounds, comprising a kind of gradient elution-adenosine.
The main Problems existing of aforesaid method is: separation process step is comparatively loaded down with trivial details, sometimes need to use chloroform for extraction agent or
Eluent, all has serious harm to human body and environment, and the kind of the purine obtained and pyrimidine bases is few, and the production cycle is longer, and production cost is higher.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, a kind of method of quick separation and purification purine and the pyrimidine bases from Chinese medicine Snakegourd Peel that provide easy and simple to handle, environmental protection, comprehensive cost low, with short production cycle.
The solution of the present invention is as follows:
From Chinese medicine Snakegourd Peel, the method for separation and purification purine and pyrimidine bases, the steps include:
(1) preparation of Snakegourd Peel crude extract: get the Snakegourd Peel medicinal material crushed, use water heating and refluxing extraction, extracting solution is about 1.2 through being evaporated to relative density, in concentrated solution, add 95% ethanol to the concentration of ethanol is about 70%, leave standstill 72 h, filter, get supernatant liquid, concentrating under reduced pressure obtains crude extract;
(2) macroporous adsorptive resins roughing out: by soluble in water for Snakegourd Peel crude extract, upper HPD826 type macroporous adsorptive resins carries out chromatography, first carry out wash-out with water, wash-out is carried out again with the ethanol-water solution that concentration is about 5%, collect the alcohol-water elutriant of water and about 5% respectively, the former concentrating under reduced pressure, obtains sample 1, the latter's concentrating under reduced pressure, obtains sample 2;
(3) the further separation and purification of sample 1: sample 1 Semipreparative chromatography is carried out separation and purification, chromatographic column is YMC ODS-AQ post, and moving phase is methanol-water, and determined wavelength is 254 nm;
(4) the further separation and purification of sample 2: sample 2 Semipreparative chromatography is carried out separation and purification, chromatographic column is YMC ODS-AQ post, and moving phase is methanol-water, and determined wavelength is 254 nm;
Collect target components cut, by the cut concentrating under reduced pressure obtained, namely obtain the monomeric compound that will be separated.
Foregoing method, preferred scheme is, during step (1) heating and refluxing extraction, extraction time is 1-3 hour, and extraction time is 2-6 time.More preferably, extraction time is 1.5-2.5 hour (preferably 2 hours), and extraction time is 3-5 time (preferably 4 times).
Foregoing method, preferred scheme is, step (3) moving phase is the methanol-water eluent (preferably 2%) of 0-5%, and eluent flow rate is 2.5-4.5 mL/min(preferably 3.5 mL/min).
Foregoing method, preferred scheme is, when step (4) carries out wash-out with methanol-water eluent, the mass concentration of methyl alcohol used is 2%-6%(preferably 4%).Eluent flow rate is 2.5-4.5 mL/min(preferably 3.5 mL/min).
Foregoing method, preferred scheme is, step (3) type of elution is methanol-water gradient elution/2% methanol-water isocratic elution/100% water isocratic elution/5% methanol-water isocratic elution, and preferably, eluent flow rate is 2.5-4.5 mL/min(preferably 3.5 mL/min).
Foregoing method, preferred scheme is, type of elution during step (4) separation and purification is 6% methanol-water isocratic elution/4% methanol-water isocratic elution/2% methanol-water isocratic elution/methanol-water gradient elution, preferably, eluent flow rate is 2.5-4.5 mL/min(preferably 3.5 mL/min).
The present invention relates to the method for separation and purification purine and pyrimidine bases from Chinese medicine Snakegourd Peel, step is: the preparation of (1) Snakegourd Peel crude extract: get the Snakegourd Peel medicinal material crushed, use water heating and refluxing extraction, extracting solution is about 1.2 through being evaporated to relative density, in concentrated solution, add 95% ethanol to the concentration of ethanol is about 70%, leaves standstill 72 h, filters, get supernatant liquid, concentrating under reduced pressure obtains crude extract.(2) macroporous adsorptive resins roughing out: by soluble in water for Snakegourd Peel crude extract, upper HPD826 type macroporous adsorptive resins carries out chromatography, first carry out wash-out with water, be that elutriant carries out wash-out with the alcohol-water that concentration is about 5% again, collect the alcohol-water elutriant of water and about 5% respectively, the former concentrating under reduced pressure, obtains sample 1, the latter's concentrating under reduced pressure, obtains sample 2.(3) the further separation and purification of sample 1: sample 1 Semipreparative chromatography is carried out separation and purification, chromatographic column is YMC ODS-AQ post (250 mm × 10 mm I. D., 10 μm, Shen, large Liaanjiang county is separated Science and Technology Ltd.), moving phase is methanol-water, and determined wavelength is 254 nm.(4) the further separation and purification of sample 2: sample 2 Semipreparative chromatography is carried out separation and purification, chromatographic column is YMC ODS-AQ post (250 mm × 10 mm I. D., 10 μm, Shen, large Liaanjiang county is separated Science and Technology Ltd.), moving phase is methanol-water, and determined wavelength is 254 nm.
The environmental protection of this technological process, to environment without serious harm, comprehensive cost is low.
The method of the present invention separation and purification 5 kinds of purine and pyrimidine bases from Chinese medicine Snakegourd Peel, first adopt macroporous adsorptive resins roughing out, then carry out separation and purification by Semipreparative chromatography method, gained target compound purity is high, foreign matter content is extremely low, and this point can be found out from Fig. 5-Fig. 9.In addition, also there is following advantage:
(1) extract can remove most impurity after macroporous adsorptive resins roughing out; the composition of mixture is simplified; can be that follow-up mask work reduces difficulty; and Semipreparative chromatography post can be protected not contaminated, effectively extend the work-ing life of chromatographic column.
(2) use twice separation and purification of Semipreparative chromatography method just can obtain cytosine(Cyt), uridylic, xanthoglobulin, guanine and xanthine 5 kinds of high-purity monomer compounds simultaneously, method is simple to operate, and efficiency is high, and process cycle is short, save reagent, reduce production cost.
(3) do not use in purge process organic solvents such as environment and the large chloroforms of harm, macroporous adsorbent resin can be reused repeatedly after regeneration, environmental protection.
(4) optimize the condition (composition of elutriant and flow velocity) of chromatography method, the purity of compound and efficiency are all greatly improved.
Accompanying drawing explanation
Fig. 1 is the high-efficient liquid phase chromatogram of sample 1.
Fig. 2 is the high-efficient liquid phase chromatogram of sample 2.
Fig. 3 is the Semipreparative chromatography figure of sample 1.
Fig. 4 is the Semipreparative chromatography figure of sample 2.
Fig. 5 is high-efficient liquid phase chromatogram and the ultraviolet spectrogram of cytosine(Cyt).
Fig. 6 is high-efficient liquid phase chromatogram and the ultraviolet spectrogram of uridylic.
Fig. 7 is hypoxanthic high-efficient liquid phase chromatogram and ultraviolet spectrogram.
Fig. 8 is high-efficient liquid phase chromatogram and the ultraviolet spectrogram of guanine.
Fig. 9 is xanthic high-efficient liquid phase chromatogram and ultraviolet spectrogram.
Embodiment
Describe technical scheme of the present invention in detail below in conjunction with embodiment and accompanying drawing, but protection domain is not by this restriction.In embodiment, equipment used or raw material all can obtain from market.Agents useful for same is all purchased from Jinan reagent head factory, and water used is deionized water.
embodiment:from Chinese medicine Snakegourd Peel, the method for separation and purification purine and pyrimidine bases, the steps include:
(1) preparation of Snakegourd Peel crude extract: Snakegourd Peel medicinal material after crushed, take water as solvothermal refluxing extraction 4 times, united extraction liquid, being evaporated to relative density is about 1.2, in concentrated solution, add 95% ethanol to the concentration of ethanol is about 70%, leaves standstill 72 h, filters, get supernatant liquid, concentrating under reduced pressure obtains crude extract.
(2) macroporous adsorptive resins roughing out: by soluble in water for Snakegourd Peel crude extract, upper HPD826 type macroporous adsorptive resins carries out chromatography, first carry out wash-out with water, wash-out is carried out again with the ethanol-water solution that concentration is about 5%, collect the alcohol-water elutriant of water and about 5% respectively, the former concentrating under reduced pressure, obtains sample 1, the latter's concentrating under reduced pressure, obtains sample 2.
(3) the further separation and purification of sample 1: sample 1 Semipreparative chromatography is carried out separation and purification, chromatographic column is YMC ODS-AQ post (250 mm × 10 mm I. D., 10 μm, Shen, large Liaanjiang county is separated Science and Technology Ltd.), moving phase is methanol-water, and determined wavelength is 254 nm.
(4) the further separation and purification of sample 2: sample 2 Semipreparative chromatography is carried out separation and purification, chromatographic column is YMC ODS-AQ post (250 mm × 10 mm I. D., 10 μm, Shen, large Liaanjiang county is separated Science and Technology Ltd.), moving phase is methanol-water, and determined wavelength is 254 nm.
Collect target components cut, by the cut concentrating under reduced pressure obtained, namely obtain the monomeric compound that will be separated.
Contriver makes moving phase by using the methyl alcohol of different concns, and adopt different types of elution, the flow velocity controlling elutriant is 2.5-4.5 mL/min(preferably 3.5 mL/min), optimized the purification condition realizing the object of the invention, regarding assay result is as follows:
The Semipreparative chromatography separation condition of table one sample 1
| Elutriant condition | |
| Embodiment 1 | 5% methanol-water isocratic elution |
| Embodiment 2 | 2% methanol-water isocratic elution |
| Embodiment 3 | 100% water isocratic elution |
| Embodiment 4 | Methanol-water gradient elution |
In embodiment 1, adopt 5% methanol-water to be elutriant isocratic elution, each composition elution time is shorter, but separating effect is not ideal enough each other, and gained material is lower.Adopt 2% methanol-water to be elutriant isocratic elution in embodiment 2, be separated good between each composition, disengaging time is also comparatively suitable.Adopt 100% water to be elutriant isocratic elution in embodiment 3, each component separating is good, but disengaging time is oversize.Embodiment 4 adopts methanol-water gradient elution, and each component separating is good, and disengaging time is also passable, but elutriant causes recycling to there is larger difficulty due to change in concentration.
Fig. 3 is the color atlas when selecting embodiment 2 system, and as seen from Figure 3, each component separating is good, and disengaging time is also comparatively suitable.Collect each peak component according to color atlas, after recycling design, corresponding high-purity compound can be obtained.Through high performance liquid chromatography area normalization method analytical test, the purity of each component that embodiment 2 obtains is very high, and all more than 98%, this point can be found out from Fig. 5-Fig. 6.
The Semipreparative chromatography separation condition of table two sample 2
| Elutriant condition | |
| Embodiment 5 | 6% methanol-water isocratic elution |
| Embodiment 6 | 4% methanol-water isocratic elution |
| Embodiment 7 | 2% methanol-water isocratic elution |
| Embodiment 8 | Methanol-water gradient elution |
In embodiment 5, adopt 6% methanol-water to be elutriant isocratic elution, each composition elution time is shorter, but separating effect is not ideal enough each other, and gained material is lower.Adopt 4% methanol-water to be elutriant isocratic elution in embodiment 6, be separated good between each composition, disengaging time is also comparatively suitable.Adopt 2% methanol-water to be elutriant isocratic elution in embodiment 7, each component separating is good, but disengaging time is oversize.Embodiment 8 adopts methanol-water gradient elution, and each component separating is good, and disengaging time is also passable, but elutriant causes recycling to there is larger difficulty due to change in concentration.
Fig. 4 is the color atlas when selecting embodiment 6 system, and as seen from Figure 4, each component separating is good, and disengaging time is also comparatively suitable.Collect each peak component according to color atlas, after recycling design, corresponding high-purity compound can be obtained.Through high performance liquid chromatography area normalization method analytical test, the purity of each component that embodiment 6 obtains is very high, and all more than 98%, this point can be found out from Fig. 7-Fig. 9.
According to the test that proton nmr spectra and carbon are composed, gained peak component is identified, obtains cytosine(Cyt), uridylic, xanthoglobulin, guanine and xanthine.The structural formula of 5 compounds obtained through Modern spectroscopy data acknowledgement institute extraction purification is as follows:
The qualification result of 5 kinds of compounds is as follows:
Compound I (cytosine(Cyt)):
1h-NMR(400 MHz, DMSO-d
6)
δppm:10.47(1H, br s, 1-H), 7.32(1H, d,
j=6.8 Hz, 6-H), 7.04(2H, br s, 4-NH
2), 5.57(1H, d,
j=6.8 Hz, 5-H).
13C-NMR（100 MHz，DMSO-d
6）
δppm：166.6（C-4），156.8（C-2），142.5（C-6），92.4（C-5）。
Compound II per (uridylic):
1h-NMR(400 MHz, DMSO-d
6)
δppm:10.48(2H, br s, 1-H, 3-H), 7.39(1H, d,
j=7.6 Hz, H-6), 5.44(1H, d,
j=7.6 Hz, H-5).
13C-NMR（100 MHz，DMSO-d
6）
δppm：164.1（C-4），151.4（C-2），142.1（C-6），100.0（C-5）。
Compound III (xanthoglobulin):
1h-NMR(400 MHz, DMSO-d
6)
δppm:13.20(1H, br s, 9-H), 12.29(1H, br s, 1-H), 8.18(1H, s, 2-H) and, 8.11(1H, s, H-8).
13C-NMR（100 MHz，DMSO-d
6）
δppm：155.6（C-6），153.7（C-4），152.7（C-8），144.1（C-2），119.5（C-5）。
Compound IV (guanine):
1h-NMR(400 MHz, D
2o)
δppm:7.34(1H, s, 8-H).
13C-NMR（100 MHz，D
2O）
δppm：155.8（C-6），149.1（C-4），147.2（C-2），136.7 （C-8），106.5（C-5）。
Compound V(xanthine):
1h-NMR(400 MHz, D
2o)
δppm:7.35(1H, s, 8-H).
13C-NMR（100 MHz，D
2O）
δppm：155.4（C-6），152.2（C-2），150.4（C-4），141.6（C-8），106.9（C-5）。
It should be pointed out that embodiment is the more representational example of the present invention, obvious technical scheme of the present invention is not limited to above-described embodiment.A lot of distortion can also be had.Those of ordinary skill in the art, mentions or associates disclosed in from then in file, all should think the claimed scope of this patent.
Claims (13)
1. the method for separation and purification purine and pyrimidine bases from Chinese medicine Snakegourd Peel, it is characterized in that, step is:
(1) preparation of Snakegourd Peel crude extract: get the Snakegourd Peel medicinal material crushed, use water heating and refluxing extraction, extracting solution is 1.2 through being evaporated to relative density, in concentrated solution, add 95% ethanol to the concentration of ethanol is 70%, leave standstill 72h, filter, get supernatant liquid, concentrating under reduced pressure obtains crude extract;
(2) macroporous adsorptive resins roughing out: by soluble in water for Snakegourd Peel crude extract, upper HPD826 type macroporous adsorptive resins carries out chromatography, first carry out wash-out with water, wash-out is carried out again with the ethanol-water solution that concentration is 5%, collect the alcohol-water elutriant of water and 5% respectively, the former concentrating under reduced pressure, obtains sample 1, the latter's concentrating under reduced pressure, obtains sample 2;
(3) the further separation and purification of sample 1: sample 1 Semipreparative chromatography is carried out separation and purification, chromatographic column is YMC ODS-AQ post, and moving phase is methanol-water, and determined wavelength is 254nm;
(4) the further separation and purification of sample 2: sample 2 Semipreparative chromatography is carried out separation and purification, chromatographic column is YMC ODS-AQ post, and moving phase is methanol-water, and determined wavelength is 254nm;
Collect target components cut, by the cut concentrating under reduced pressure obtained, namely obtain cytosine(Cyt), uridylic, xanthoglobulin, guanine and xanthine monomeric compound.
2. method according to claim 1, is characterized in that, during step (1) reflux, extraction time is 1-3 hour.
3. method according to claim 2, is characterized in that, step (1) extraction time is 1.5-2.5 hour.
4. method according to claim 3, is characterized in that, step (1) extraction time is 2 hours.
5. method according to claim 1, is characterized in that, step (1) extraction time is 2-6 time.
6. method according to claim 1, is characterized in that, step (1) extraction time is 3-5 time.
7. method according to claim 1, is characterized in that, step (1) extraction time is 4 times.
8. method according to claim 1, is characterized in that, step (3) type of elution is methanol-water gradient elution/2% methanol-water isocratic elution/100% water isocratic elution/5% methanol-water isocratic elution.
9. method according to claim 8, is characterized in that, eluent flow rate is 2.5-4.5mL/min.
10. method according to claim 8, is characterized in that, eluent flow rate is 3.5mL/min.
11. methods according to claim 1, is characterized in that, type of elution during step (4) separation and purification is 6% methanol-water isocratic elution/4% methanol-water isocratic elution/2% methanol-water isocratic elution/methanol-water gradient elution.
12. methods according to claim 11, is characterized in that, eluent flow rate is 2.5-4.5mL/min.
13. methods according to claim 12, is characterized in that, eluent flow rate is for selecting 3.5mL/min.
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Inventor after: Li Aifeng Inventor after: Sun Ailing Inventor after: Liu Renmin Inventor after: Zhang Yongqing Inventor after: Huang Zhenhui Inventor before: Li Aifeng Inventor before: Zhang Yongqing Inventor before: Liu Renmin Inventor before: Sun Ailing |
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Free format text: CORRECT: INVENTOR; FROM: LI AIFENG ZHANG YONGQING LIU RENMIN SUN AILING TO: LI AIFENG SUN AILING LIU RENMIN ZHANG YONGQING HUANG ZHENHUI Free format text: CORRECT: ADDRESS; FROM: 252059 LIAOCHENG, SHANDONG PROVINCE TO: 250300 JINAN, SHANDONG PROVINCE |
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Effective date of registration: 20150106 Address after: 250300, 4655, University Road, Changqing District, Shandong, Ji'nan Applicant after: Shandong University of Traditional Chinese Medicine Applicant after: Shanghai No.1 Biochemical & Pharmaceutical Co., Ltd. Applicant after: Liaocheng University Address before: 252059 Hunan Road, Dongchangfu, Shandong, No. 1, Applicant before: Liaocheng University |
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