CN110066303B - Method for preparing chrysanthemum new alkyne A from Huai chrysanthemum and application thereof - Google Patents
Method for preparing chrysanthemum new alkyne A from Huai chrysanthemum and application thereof Download PDFInfo
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Abstract
The invention relates to a method for preparing chrysanthemum new alkyne A from Huai chrysanthemum and application thereof, which can effectively solve the problems of extracting chrysanthemum new alkyne A from Huai chrysanthemum and realizing the application of the chrysanthemum new alkyne A as a unique active ingredient in preparing anti-inflammatory drugs, wherein the Huai chrysanthemum is subjected to tissue crushing and extraction by using an acetone aqueous solution, an extracting solution is subjected to reduced pressure concentration to obtain an extract, the extract is dispersed by using water, petroleum ether, ethyl acetate and n-butyl alcohol are sequentially used for extraction, a silica gel column is arranged on an ethyl acetate part, and dichloromethane-methanol gradient elution is used for obtaining fraction Fr.1-4; dissolving fraction Fr.3 with methanol, centrifuging, filtering to remove insoluble substances, concentrating the obtained sub-fraction Fr.3.1 under reduced pressure, loading on MCI column, sequentially gradient-eluting with water and methanol, spray-detecting with anisaldehyde-concentrated sulfuric acid, separating the obtained sub-fraction Fr.3.1.1 with semi-preparative HPLC, and collecting retention time tRAnd (3) concentrating and drying the fraction of which the speed is 25.0-27.0 min to obtain the compound chrysanthemum new alkyne A. The preparation method is easy to operate, scientific and reasonable, and develops a new way of anti-inflammatory drugs, thereby improving the medicinal value and the commercial value of the Huai chrysanthemum.
Description
Technical Field
The invention relates to medicine, in particular to a method for preparing chrysanthemum new alkyne A from Huai chrysanthemum and application thereof.
Background
Chrysanthemum morifolium Ramat is the dried capitate inflorescence of Compositae Chrysanthemum, which is listed as the first product in Shen nong Ben Cao Jing. It is sweet and bitter in taste, cool in nature, mainly entering lung and liver meridians, and has effects of dispelling wind and heat, suppressing hyperactive liver, improving eyesight, clearing heat and detoxicating. The new Huai chrysanthemum in 2015 edition of Chinese pharmacopoeia is used as chrysanthemum together with Bo chrysanthemum, Chu chrysanthemum, tribute chrysanthemum and Hangzhou chrysanthemum, thus confirming the medicinal status of Huai chrysanthemum. Huai chrysanthemum (Dendranthema morifolium (Ramat.) kitam) is one of four Huai nationalities, mainly produced in Wu 38495, Wen county areas in Henan, and has a long planting history, and is one of medicinal materials in the southern river. Huai Ju Hua has the functions of clearing away heat and toxic material, dispelling wind and heat, calming the liver and improving eyesight, wherein Bai Ju Hua is good at calming the liver and improving eyesight, while Huang Ju Hua is mostly used for dispelling wind and clearing heat. 1 new diepoxy lignanoid compound, namely chrysanthemum new alkyne A, is separated and identified from the Huai chrysanthemum. The experimental result shows that the chrysanthemum new alkyne A can remarkably reduce NO released by RAW264.7 cells induced by LPS and has a good anti-inflammatory effect, but NO public report is found so far.
Disclosure of Invention
In view of the above situation, in order to overcome the defects of the prior art, the invention aims to provide a method for preparing chrysanthemum new alkyne A from Huai chrysanthemum and application thereof, which can effectively solve the problem of extracting chrysanthemum new alkyne A from Huai chrysanthemum and realizing application of chrysanthemum new alkyne A as a unique active ingredient in preparing anti-inflammatory drugs.
The technical scheme for solving the problem is that the method for preparing chrysanthemum new alkyne A from Huai chrysanthemum, which is an active component extracted from Huai chrysanthemum and has a molecular structural formula as follows:
the preparation method comprises the following steps: crushing and extracting flos Chrysanthemi with acetone water solution, concentrating the extractive solution under reduced pressure to obtain extract, dispersing the extract with water, sequentially extracting with petroleum ether, ethyl acetate and n-butanol to obtain petroleum ether fraction, ethyl acetate fraction, n-butanol fraction and water fraction; putting the ethyl acetate part on a silica gel column, and performing gradient elution by using dichloromethane-methanol to obtain four fractions Fr.1-4;
dissolving fraction Fr.3 with methanol, centrifuging, and filtering to remove insoluble substances to obtain fraction Fr.3.1; concentrating the sub-fraction Fr.3.1 under reduced pressure, loading onto MCI column, sequentially eluting with water and methanol, spray-identifying with anisaldehyde-concentrated sulfuric acid, identifying once per 100mL, and mixing the same fractions to obtain sub-fraction Fr.3.1.1-Fr.3.1.7; subfraction fr.3.1.1 was separated by semi-preparative HPLC with the above specification numbers: 250X 10mm, particle size 5 μm, pore size 12nm YMC-Pack ODS-AA chromatographic column, mobile phase acetonitrile: the mass concentration of the trifluoroacetic acid aqueous solution is two ten-thousandth, the flow rate is 3ml/min, and the collection retention time t is 23: 77RConcentrating and drying the part which is 25.0-27.0 min to obtain the compound chrysanthemum new alkyne A.
The preparation method is easy to operate, scientific and reasonable, the prepared chrysanthemum new alkyne A remarkably reduces LPS (low-cholesterol) induced RAW264.7 cells to release NO, is effectively used for preparing the anti-inflammatory drug, realizes the application of the chrysanthemum new alkyne A as the only active component in preparing the anti-inflammatory drug, develops a new way of the anti-inflammatory drug, improves the medicinal value and the commercial value of the Huai chrysanthemum and has remarkable economic and social benefits.
Drawings
FIG. 1 shows the preparation of the compound chrysanthemumeneyne A1H-NMR Spectroscopy (in CD)3OD) plot.
FIG. 2 shows the preparation of the compound chrysanthemumeneyne A13C-NMR Spectroscopy (in CD)3OD) plot.
FIG. 3 is the DEPT 135 spectrum (in CD) of the compound chrysanthemum new alkyne A of the present invention3OD) plot.
FIG. 4 shows chrysanthemum new alkyne A of the compound of the present invention1H-1H COSY spectra (in CD)3OD) plot.
FIG. 5 shows the HSQC spectra (in CD) of the compound chrysanthemumeneyne A of the present invention3OD) plot.
FIG. 6 shows the HMBC spectra (in CD) of the compound chrysanthemumeneyne A of the present invention3OD) plot.
FIG. 7 is a NOESY spectrum (in CD) of the compound chrysanthemumeneyne A of the present invention3OD) plot.
FIG. 8 is the HR-ESI-MS spectrum (in CD) of the compound chrysanthemum new alkyne A of the present invention3OD) plot.
FIG. 9 shows the IR spectrum (in CD) of the compound chrysanthemumeneyne A of the present invention3OD) plot.
FIG. 10 shows the UV spectrum (in CD) of the compound chrysanthemumeneyne A of the present invention3OD) plot.
Detailed Description
The following detailed description of the embodiments of the present invention refers to the accompanying drawings.
In specific implementation, the invention relates to a method for preparing chrysanthemum new alkyne A from Huai chrysanthemum, wherein the chrysanthemum new alkyne A is an active component extracted from Huai chrysanthemum, and the preparation method comprises the following steps: 11.2kg of Huai chrysanthemum, crushing and extracting for 2 times by using acetone aqueous solution with volume concentration of 50%, wherein the dosage of acetone is 120L each time, combining 2 extracting solutions, and concentrating under reduced pressure to obtain 1.8kg of extract; dispersing the extract with 9L water, sequentially extracting with 5 × 10L petroleum ether, 5 × 10L ethyl acetate, and 5 × 10L n-butanol to obtain petroleum ether fraction, ethyl acetate fraction, n-butanol fraction, and water fraction; subjecting the ethyl acetate part to a 1000g silica gel column, and performing gradient elution by using dichloromethane-methanol 50:1, 30:1, 20:1 and 5:1 to obtain four corresponding fractions Fr.1-4;
dissolving fraction Fr.3 with 50mL of methanol, centrifuging at 6000 rpm for 15min at 20 deg.C, and centrifuging to remove insoluble substances to obtain fraction Fr.3.1; concentrating the sub-fraction Fr.3.1 under reduced pressure to 20mL, loading on MCI column, sequentially eluting with water, 10% volume concentration, 20% volume concentration, 30% volume concentration, 40% volume concentration, and 100% volume concentration methanol, wherein each elution part is 10 times of column volume, flow rate is 3mL/min, and spraying anisaldehyde-concentrated sulfuric acidFog identification, wherein the identification is carried out once per 100mL, and the same fractions are combined to obtain a sub-stream fraction Fr.3.1.1-Fr.3.1.7; subfraction fr.3.1.1 was separated by semi-preparative HPLC with the above specification numbers: 250X 10mm, particle size 5 μm, pore size 12nm YMC-Pack ODS-AA chromatographic column, mobile phase acetonitrile: the mass concentration of the trifluoroacetic acid aqueous solution is two ten-thousandth, the flow rate is 3ml/min, and the collection retention time t is 23: 77RConcentrating and drying the part which is 25.0-27.0 min to obtain the compound chrysanthemum new alkyne A.
The compound chrysanthemum new alkyne A has the advantages of remarkably reducing NO released by RAW264.7 cells induced by LPS, being effectively used for preparing anti-inflammatory drugs and realizing the application of chrysanthemum new alkyne A as the only active component in preparing anti-inflammatory drugs.
The method obtains the same or similar results after repeated trial, which shows that the method is stable and reliable and has good practical application value, the prepared compound chrysanthemum new alkyne A has the advantages of remarkably reducing NO released by RAW264.7 cells induced by LPS, having good anti-inflammatory effect, and obtaining very good effective technical effect through experiments, and the related data are as follows:
1 Instrument and reagent
Bruker AVANCE III 500 NMR Spectrometer (TMS internal standard) (Bruker), Nicolet is 10Microscope Spectrometer for IR spectroscopy (Thermo Scientific, USA), Bruker maxis HD mass Spectrometer for high-resolution mass spectroscopy, Shimadzu UV-2401PC appaatus for UV spectroscopy, Waters Alliance series 2695 HPLC system for HPLC equipped with 2998 type diode array detector, Empower3 datA workstation, LC50 type HPLC, UV200 type UV detector [ Sekikuri (Beijing technology limited) ], YMC-Pack-A column (250X 10mm. D.S-5mm,12mm) (YMC limited), and N-1100 type rotary evaporator (Shanghai Langlan apparatus, A-1000 type water flow machine (Shanghai Langlan apparatus, Ltd.), N-1111 type refrigerating apparatus (Shanghai Liang air extractor), FDU-2110 type freeze dryer (Shanghai Elang instruments Co., Ltd.), DFZ-60508 type vacuum drying oven (Shanghai Hengscientific instruments Co., Ltd.), AB 204-Nten thousandth precision analytical balance (METTLER TOLEDO), iMARK type enzyme-labeling instrument (U.S. BIO-RAD), carbon dioxide incubator (Shanghai STIK), ultra-clean bench (Sujing group), Arium 611VF ultra-combined ultra-pure water device (SARTORIUS), inverted microscope (Nikon), PB-10 acidimeter (Cetorula, Germany), SORVALL ST16R Centrifuge high-speed low-temperature freezing Centrifuge (Thermo Fisher Scientific Co., Ltd.); microplate reader (BIO-RAD 680); clean bench (Jiangsu Sujing group); 90-3 magnetic stirrers (Shanghai Shajie laboratory Equipment, Inc.); RD-7080 full-automatic new air-blast drying oven (Shanghai Zhicheng analytical instruments manufacturing Co., Ltd.); microsampler (Nichipet EX PLUS); AB204-N electronic reading analytical balance (product of Metler-Tollido instruments, Inc.; Shanghai); 10cm petri dish, 96-well plate, cryopreservation tube (Corning); common surgical instruments.
The column chromatography packing materials are Diaion HP-20, MCI Gel CHP-20 (Mitsubishi chemical company, Japan), Toyopearl HW-40 (TOSOH company, Japan), Sephadex LH-20 (Parmacea Biotech company), silica Gel H (160-.
Mouse macrophages (RAW264.7) were purchased from shanghai cell bank, china academy of sciences; DMEM high glucose medium (Gibco); fetal bovine serum ((Gibco); trypsin (Gibco), DMSO (solarbio); MTT (Biosharp); ampicillin, Tris base (Sigma); Griess reagent (Sigma); iNOS primary antibody (CST), Cox2 primary antibody (CST); water was ultrapure water, PBS buffer, etc. were self-prepared.
The Huai chrysanthemum selected by the invention is purchased from Jiaozuo of Henan, is identified as the dried capitula inflorescence of Dendranthema morifolium (Ramat.) motif of Huai chrysanthemum of Compositae by Chen & Daizhizu of Henan university of traditional Chinese medicine and professor, and the compound chrysanthemum new alkyne A is prepared according to the preparation method provided by the invention.
2 structural characterization
Chrysanthemum new alkyne A: white powder (CH)3OH), anisaldehyde-concentrated sulfuric acid spray orange color. HR-ESI-MS gives the peak m/z of the excimer ion:495.1834[M+Na]+(calcd.For C22H32O11Na 495.1842), and determining its molecular formula as C22H32O11；UV(MeOH)λmax:207(2.83),212(2.98),239(0.78),252(1.13),266(1.53),281(1.20)nm；IR(KBr)νmaxcm-1：3340,2924,1434,1371,1201,1134,1072,1031cm-1。
TABLE 1 NMR spectroscopic data (in CD) of Chrysanthemum noryne A3OD)
3 Activity assay
Culturing RAW264.7 cells in DMEM medium containing fetal calf serum (10%) for 1 week, selecting cells in logarithmic growth phase, washing with PBS once, adding DMEM medium, and beating uniformly at 5 × 104The cells were plated in 96-well plates at a concentration of one/mL, and the total volume of culture per well was 100. mu.L. After the cells are cultured for 24h and adhered, the cells are divided into a normal group (Con), a model group (LPS 1 mu g/mL) and a chrysanthemum new alkyne A group (50 mu M + LPS 1 mu g/mL) for continuous culture. 37 ℃ and 5% CO2After 24h of incubation, 20. mu.L of MTT solution (5mg/mL) was added to each well, incubation was continued for 4h at 37 ℃ and the culture was carefully aspirated, 100. mu.L of LDMSO was added to each well and shaken for 5-10min to completely dissolve the purple crystals. And (3) measuring the absorbance value (A) of each hole at the wavelength of 570-630nm by using a microplate reader, and calculating the average A value and the cell activity. The experiment was repeated in triplicate. Cell viability-OD value of each group/OD value of normal group.
Selecting RAW264.7 cells in logarithmic growth phase at 3 × 105The cells were plated in 96-well plates at a concentration of one/mL, and the total volume of culture per well was 100. mu.L. Culturing for 24h until the cells are attached to the wall, and dividing the cells into positive cellsThe normal group (Con), the model group (LPS 1. mu.g/mL), and the chrysanthemum new alkyne A group (50. mu.M + LPS 1. mu.g/mL) were cultured. 37 ℃ and 5% CO2After 24h of culture, 50. mu.L of cell supernatant was aspirated from each well, 50. mu.L of Griess reagent was added, and after a 5min dark reaction, the absorbance value (A) of each well was measured at 540nm, and the average A value and NO release amount were calculated. The experiment was repeated in triplicate. NO release was OD value of each group/OD value of normal group.
Selecting RAW264.7 cells in logarithmic growth phase at 1 × 105The cells were plated in 6-well plates at a concentration of one/mL, and the total volume of culture per well was 1 mL. After the cells are cultured for 24h and adhered, the cells are divided into a normal group (Con), a model group (LPS 1 mu g/mL) and a chrysanthemum new alkyne A group (50 mu M + LPS 1 mu g/mL) for continuous culture. 37 ℃ and 5% CO2After 24h of culture, total protein was extracted by careful manipulation according to the kit instructions (Beijing Sorleibao technologies, Inc.). The final concentration of total protein was determined by carefully measuring the total protein according to the BCA protein quantitation kit (Beijing Solebao technologies Co., Ltd.), adding 4 parts of Load Buffer to the remaining protein sample, boiling at 100 ℃ for 5min for denaturation, adjusting the loading protein concentration according to the total protein concentration, separating by SDS-PAGE electrophoresis, transferring to PVDF membrane, sealing with 5% skimmed milk powder at room temperature for 1.5h, and adding anti-iNOS (1:1500), COX2(1:1500), and beta-actin (1: 2000). Incubating at 4 ℃ overnight, adding a rabbit-derived fluorescent secondary antibody (1:20000), incubating at 37 ℃ for 1h, collecting protein bands by a near-infrared two-color imaging system (Odysi), and quantitatively analyzing the protein bands by using Image Studio software.
4 Activity results
MTT and Griess results show that 1 mug/mL LPS can induce RAW264.7 cell proliferation and increase NO release, but chrysanthemum new alkyne A (50 muM) can reduce NO release; the western bolt result shows that 1 mu g/mL LPS can enable the RAW264.7 cells to excessively express iNOS and Cox2 proteins, but the iNOS and Cox2 protein expression of the RAW264.7 cells is remarkably reduced by chrysanthemum new alkyne A (50 mu M), and the result shows that the chrysanthemum new alkyne A has a good anti-inflammatory effect, is used as a unique active ingredient to remarkably reduce the release of NO by LPS induced RAW264.7 cells, is effectively used for preparing anti-inflammatory drugs, develops a new way of the anti-inflammatory drugs and new application and commercial value of Huai chrysanthemum, and has remarkable economic and social benefits.
Claims (1)
1. A method for preparing chrysanthemum new alkyne A from Huai chrysanthemum is characterized in that the chrysanthemum new alkyne A is an active component extracted from Huai chrysanthemum and has a molecular structural formula as follows:
the preparation method comprises the following steps: 11.2kg of Huai chrysanthemum, crushing and extracting for 2 times by using acetone aqueous solution with volume concentration of 50%, wherein the dosage of acetone is 120L each time, combining 2 extracting solutions, and concentrating under reduced pressure to obtain 1.8kg of extract; dispersing the extract with 9L water, sequentially extracting with 5 × 10L petroleum ether, 5 × 10L ethyl acetate, and 5 × 10L n-butanol to obtain petroleum ether fraction, ethyl acetate fraction, n-butanol fraction, and water fraction; subjecting the ethyl acetate part to a 1000g silica gel column, and performing gradient elution by using dichloromethane-methanol 50:1, 30:1, 20:1 and 5:1 to obtain four corresponding fractions Fr.1-4;
dissolving fraction Fr.3 with 50mL of methanol, centrifuging at 6000 rpm for 15min at 20 deg.C, and centrifuging to remove insoluble substances to obtain fraction Fr.3.1; concentrating the sub-fraction Fr.3.1 under reduced pressure to 20mL, loading on MCI column, eluting with water, 10% volume concentration, 20% volume concentration, 30% volume concentration, 40% volume concentration and 100% volume concentration methanol sequentially, wherein the amount of each eluting part is 10 times of the column volume, the flow rate is 3mL/min, performing spray identification by anisaldehyde-concentrated sulfuric acid, performing identification once per 100mL, and combining the same fractions to obtain sub-fraction Fr.3.1.1-Fr.3.1.7; subfraction fr.3.1.1 was separated by semi-preparative HPLC with the above specification numbers: 250X 10mm, particle size 5 μm, pore size 12nm YMC-Pack ODS-AA chromatographic column, mobile phase acetonitrile: 23: 77, the mass concentration of the trifluoroacetic acid aqueous solution is two ten-thousandth, the flow rate is 3mL/min, and the collection retention time tRAnd concentrating and drying the fraction of 25.0-27.0 min to obtain the compound chrysanthemum new alkyne A.
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| "Antiallergic Agents from Natural Sources. 3. Structures and Inhibitory Effects on Nitric Oxide Production and Histamine Release of Five Novel Polyacetylene Glucosides from Bidens parvifloraWILLD";Naili Wang等;《Chem. Pharm. Bull.》;20011231;第49卷(第8期);全文 * |
| "LIGNAN AND ACETYLENIC GLYCOSIDES FROM ASTER AURICULATUS";Chang Zeng Wang等;《Phytochemistry》;19981231;第48卷(第4期);全文 * |
| "New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities";Jun He等;《Carbohydrate Research》;20111231;第346卷(第13期);第1906页右栏第1段、图1 * |
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