CN115057770A - Preparation method of triterpenic acid compound in black tiger pericarp - Google Patents
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Abstract
A method for preparing triterpenic acid compound from black tiger pericarp comprises drying black tiger pericarp, pulverizing, ultrasonic extracting with ethanol, evaporating filtrate, concentrating to obtain paste, and removing water soluble part to obtain water insoluble extract; and then carrying out high-speed counter-current chromatography separation, and collecting target components to obtain compounds Seco-neolcadsaranic acid A and Neokadsuranic acid A with the purity of more than 95%. The method is simple, convenient, rapid and good in reproducibility, is suitable for mass preparation, and lays a material foundation for further activity research of triterpenoid.
Description
Technical Field
The invention relates to a method for extracting a triterpenic acid compound from plants, in particular to a method for separating and preparing the triterpenic acid compound from black cutworm pericarp.
Background
Black tiger (Kadsura coccinea (Lem.) a.c. smith) is called clod and bufena, etc., is a plant of Kadsura of schisandra, the root of which is a commonly used traditional Chinese medicine with warm nature, pungent taste and slight bitter taste, has the efficacies of promoting qi circulation, relieving pain, dispelling wind, activating collaterals, dispersing nodules of the spleen and reducing swelling, and is commonly used for treating stomach, duodenal ulcer, chronic gastritis, acute gastroenteritis, rheumatic arthritis, traumatic swelling and pain, dysmenorrhea, blood stasis and abdominal pain, etc. in folk.
In recent years, researchers at home and abroad mainly separate more than five hundred chemical components from schisandra plants by using a traditional silica gel column chromatography method, wherein lignans are more than three hundred and triterpenes are nearly two hundred, and the components have activities in aspects of anti-HIV activity, anti-platelet aggregation, anti-tumor, anti-hepatitis B virus and the like, so that the search and discovery of a new structure and new activity from the schisandra plants become research hotspots.
According to the literature, the triterpenoid is mainly obtained from roots and prepared by combining repeated silica gel column chromatography or silica gel column chromatography, so that the method has the defects of complex operation, poor reproducibility, long time consumption, irreversible adsorption of the compound and the like.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for separating and preparing a triterpenic acid compound from black tiger pericarp by adopting high-speed countercurrent chromatography.
In order to achieve the purpose, the invention adopts the technical scheme that: a method for preparing a triterpenic acid compound in black cutworm pericarp comprises the following steps:
A. drying and pulverizing Tiger pericarp, performing ultrasonic extraction with ethanol at room temperature to obtain crude extract, evaporating and concentrating the crude extract to obtain paste, performing ultrasonic extraction with distilled water to remove water soluble part, dissolving with methanol, and volatilizing methanol in water bath to obtain water insoluble extract;
the above-mentioned ultrasonic extraction with ethanol at room temperature means that 0.8L of 60-80% ethanol is added into 100g of black tiger pericarp powder, ethanol is added into the black tiger pericarp powder, ultrasonic extraction is carried out for 55-65min at room temperature, suction filtration is carried out, filter residue is subjected to ultrasonic extraction for several times at room temperature by using 60-80% ethanol at room temperature, each extraction is carried out for 25-35min, suction filtration is carried out, and filtrate is combined to obtain crude extract. Wherein, when the residue is subjected to ultrasonic extraction, the dosage of ethanol can be reduced with the increase of extraction times, such as 0.4L for the 1 st time, and 0.1L for the next time.
The ultrasonic extraction with distilled water to remove water soluble part refers to adding distilled water into the paste obtained by evaporation and concentration, performing ultrasonic extraction at room temperature, performing suction filtration, adding distilled water into the filter residue, performing ultrasonic extraction at room temperature, performing suction filtration, discarding the filtrate, and keeping the filter residue for later use; wherein the addition amount of distilled water is 10-15 times of the paste mass during each extraction.
Preferably, the drying temperature of the black tiger pericarp is 55-65 ℃; the water bath temperature when the methanol is volatilized to dryness is 90-100 ℃.
B. Selecting a solvent system of high-speed counter-current chromatography: mixing petroleum ether, ethyl acetate, methanol and distilled water according to a volume ratio of 9:3:6: 1; wherein, the upper phase of the solvent system is a stationary phase, and the lower phase is a mobile phase.
C. B, ultrasonically dissolving the water-insoluble extract obtained in the step A by using a lower phase of a high-speed counter-current chromatography solvent system, performing high-speed counter-current chromatography separation, collecting fractions within the peak time of 110min-125min to obtain a compound Seco-neolcadsaranic acid A, and collecting fractions within the peak time of 175min-190min to obtain a compound Neokadsuranic acid A; wherein, the high-speed counter-current chromatography separation conditions are as follows: the flow rate is 2mL/min, the rotation speed of a main machine is 850rpm, the temperature is 20 ℃, and the detection wavelength is 254 nm.
The invention establishes a method for separating and preparing triterpenic acid chemical components from black cutworm pericarp by high-speed countercurrent chromatography, and obtains two triterpenic acid compounds with purity of more than 95%, namely, Seco-neolcadsaranic acid A and Neokadsuranic acid A, wherein the Neokadsuranic acid A is firstly found in the black cutworm, and both are cycloartenane triterpenoids, and the components have various pharmacological activities such as anti-HIV activity, anti-cancer activity and the like. The method is simple, convenient, rapid and good in reproducibility, is suitable for mass preparation, and lays a material foundation for further activity research of triterpenoids.
Drawings
FIG. 1 is an HPLC chart of a methanol-dissolved solution of the water-insoluble part of the ethanol extract of the pericarp of Kadsura coccinea.
FIG. 2 is a graph of HSCCC separation of the target compound from the pericarp of black tiger (254 nm).
FIG. 3 is an HPLC chart of Compound 1.
FIG. 4 is an HPLC chart of Compound 2.
Detailed Description
Example 1
Taking mature black tiger fruits, removing pulp, drying peel in an oven at 60 ℃, and crushing. Taking 500g of kadsura coccinea peel powder, performing ultrasonic extraction for 60min at room temperature by using 4L of 70% ethanol by mass fraction, performing suction filtration, performing ultrasonic extraction on filter residues for 30min by using 2L of ethanol with the same concentration, filtering, performing ultrasonic extraction on the filter residues for 30min by using 0.5L of ethanol with the same concentration again, performing suction filtration, combining filtrates, concentrating the mixture in a rotary evaporator to obtain an extract, adding 100ml of distilled water for ultrasonic extraction, performing suction filtration to obtain filter residues, adding 100ml of distilled water into the filter residues for ultrasonic extraction, removing the filtrate, dissolving and transferring the filter residues in methanol, placing the filter residues in an evaporating dish, volatilizing the methanol in a water bath kettle at 90-100 ℃ to obtain 9.5g of an extract, and performing high performance liquid chromatography (the conditions are shown in the following table) as shown in figure 1, wherein peak 1 and peak 2 are separation target components.
The conditions of the high performance liquid chromatography are as follows: the chromatographic column adopts GL Science Wondasil TM C18 column (4.6X 250mm, 5 μm internal diameter), mobile phase A: 0.2% phosphoric acid water, B: and (3) acetonitrile. Isocratic elution, 0-45 min: 85%, flow rate of 1mL/min, column temperature of 30 ℃, DAD detector, output wavelength of 210nm and 254 nm.
Selection of two-phase solvent system: a plurality of lipophilic component separation systems are screened, the K values of petroleum ether-ethyl acetate-methanol-water systems are found to be relatively proper, the K value measurement results of different solvent ratios are shown in a table 1, and the K values of two compounds in the system 3 are relatively good, so that the system is selected for on-machine operation separation. The retention of machine operation on system 3 was 86%.
TABLE 1 HSCCC solvent system K value screening Table
In proportion 9:3:6: 1(v/v) mixing 900ml of petroleum ether, 300ml of ethyl acetate, 600ml of methanol and 100ml of distilled water, shaking, fully mixing uniformly, and standing overnight; separating the upper phase from the lower phase, removing bubbles by ultrasonic wave for 10min, taking the upper phase as a stationary phase, pumping the upper phase into the pipeline at a flow rate of 20mL/min, taking the lower phase as a mobile phase, performing high-speed countercurrent chromatography at a flow rate of 2mL/min, rotating the main machine at 850rpm, and detecting the wavelength at 254 nm. After the system is balanced, dissolving 600mg of the prepared water-insoluble extract by using 20mL of lower phase ultrasound, sampling, collecting a chromatogram after sampling, and collecting according to a chromatogram flow chart. Collecting fraction I for 110-125 min to obtain compound 1, and collecting fraction II for 175-190 min to obtain compound 2.
The HSCCC separation spectrum is shown in figure 2, and HPLC analysis (high performance liquid chromatography conditions are the same as above) of fraction I and fraction II shows that, by combining the graph shown in figure 3 and figure 4, the fraction I is a peak 1 compound, the purity is 98% by an area normalization method, the fraction II is a peak 2 compound, and the purity is 95% by the area normalization method.
Concentrating the effluent of fraction I and fraction II, dissolving with a small amount of methanol, transferring into a drying bottle, adding 4-5 times of pure water, freezing at-20 deg.C in a refrigerator, and freeze-drying in a freeze-drying machine to obtain dry powder. In total, 110mg of Compound 1 and 70mg of Compound 2 were prepared from 500g of starting material.
The structure of the compound is identified by nuclear magnetic resonance as follows: compound 1Seco-neolcadsaranic acid A, Compound 2Neokadsuranic acid A, the specific data are as follows:
compound 1: 467.3145 1 H-NMR(CD 3 OD,500MHz)'H-NMR(DMSO):δ0.78(3H,d,J＝8.0Hz,C-21H),0.93(6H,d,J＝7.0Hz,C-19H,C-28H),1.70(3H,s,C-29H),1.79(3H,s,C-27H),2.90(1H,s,C-12H),4.66,(2H,s,C-18H),4.75(1H,d,J＝3.5Hz,C-30H),4.86(1H,s,C-30H),4.94(1H,s,C-11H),5.89(1H, t, J ═ 11.0Hz, C-24H); 13C-NMR (DMSO,125MHz) delta 31.42(C-1),28.72(C-2),175.49(C-3),141.91(C-4),56.63(C-5),24.30(C-6),28.26(C-7),49.04(C-8),152.38(C-9),40.97(C-10),122.06(C-11),58.33(C-12),149.96(C-13),43.69(C-14),33.49(C-15),29.19(C-16),54.18(C-17),114.19(C-18),17.99(C-19),32.21(C-20),17.86(C-21),33.60(C-22),26.62(C-23),146.69(C-24),127.96(C-25),169.32(C-26),21.14(C-27),20.85(C-28),23.68(C-29),112.65 (C-30). Determining that the compound 1 is Seco-neo lcadsarac acid A, and the molecular formula is as follows: c 30 H 44 O 4 The structural formula is shown in the following,
compound 2: 451.3212 1 H-NMR(CD3OD,500MHz)'H-NMR(DMSO):δ0.77(3H,d,J＝8.0Hz,C-21H),1.17(3H,s,C-19H),0.91(3H,s,C-28H),1.78(3H,s,C-27H),2.86(1H,s,C-12H),4.63(1H,d,J＝3.0Hz,C-18H),4.75(1H,d,J＝3.5Hz,C-18H),4.85(1H,s,C-11H),5.80(1H,t,J＝8.0Hz,C-24H),0.96(3H,d,J＝8.5Hz,C-29H),0.96(3H,d,J＝8.5Hz,C-30H)； 13 C-NMR (DMSO,125MHz) delta 35.28(C-1),34.73(C-2),215.23(C-3),47.67(C-4),54.81(C-5),23.01(C-6),29.37(C-7),53.49(C-8),154.87(C-9),37.51(C-10),119.56(C-11),59.59(C-12),149.88(C-13),43.18(C-14),34.50(C-15),24.27(C-16),48.61(C-17),112.92(C-18),18.18(C-19),33.10(C-20),18.08(C-21),33.46(C-22),26.53(C-23),141.41(C-24),128.24(C-25),169.23(C-26),21.31(C-27),22.17(C-28),24.28(C-29),21.62 (C-30). Determining the compound as Neokadsuranic acid A, wherein the molecular formula is as follows: c 30 H 44 O 3 The structural formula is shown as follows:
Claims (8)
1. a method for preparing a triterpenic acid compound in black cutworm pericarp is characterized by comprising the following steps:
A. drying and pulverizing Tiger pericarp, performing ultrasonic extraction with ethanol at room temperature to obtain crude extract, evaporating and concentrating the crude extract to obtain paste, performing ultrasonic extraction with distilled water to remove water soluble part, dissolving with methanol, and volatilizing methanol in water bath to obtain water insoluble extract;
B. selecting a solvent system of high-speed counter-current chromatography: mixing petroleum ether, ethyl acetate, methanol and distilled water according to a volume ratio of 9:3:6: 1;
C. ultrasonically dissolving the water-insoluble extract obtained in the step A by using a lower phase of a high-speed countercurrent chromatography solvent system, carrying out high-speed countercurrent chromatography separation, and respectively collecting fractions within 110-125 min and 175-190 min of peak time to obtain a compound Seco-neolcadsaranic acid A and a compound Neokadsuranic acid A; wherein, the separation conditions are as follows: the flow rate is 2mL/min, the rotation speed of a main machine is 850rpm, the temperature is 20 ℃, and the detection wavelength is 254 nm.
2. The method for preparing triterpenic acid compounds from black tiger pericarp as claimed in claim 1, wherein the ultrasonic extraction with ethanol at room temperature in step A is that 100g of black tiger pericarp powder is added with 0.8L of 60-80% ethanol, ethanol is added into black tiger pericarp powder, ultrasonic extraction is carried out at room temperature for 55-65min, suction filtration is carried out, filter residue is subjected to ultrasonic extraction with 60-80% ethanol at room temperature for several times, each time for 25-35min, suction filtration is carried out, and filtrate is combined to obtain crude extract.
3. The method for preparing the triterpenic acid compound from the black cutworm pericarp as claimed in claim 1, wherein the ultrasonic extraction with distilled water to remove the water-soluble part in the step A is to add distilled water into the paste obtained by evaporation and concentration, perform ultrasonic extraction at room temperature, perform suction filtration, add distilled water into the filter residue, perform ultrasonic extraction at room temperature, perform suction filtration, discard the filtrate, and leave the filter residue for use; wherein the addition amount of distilled water is 10-15 times of the paste material amount during each extraction.
4. The method of claim 1, wherein the solvent system of step B is a stationary phase and a mobile phase.
5. The method of claim 1, wherein the drying temperature of the pericarp of black cutworm in step A is 55-65 ℃.
6. The method of claim 1, wherein said aqueous bath temperature in step a is between about 90 ℃ and about 100 ℃.
7. The method of claim 1, wherein said compound Seco-neolcadsaranic acid a is 98% pure.
8. The method of claim 1, wherein said compound Neokadsuranic acid A is 95% pure.
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