CN109988206B - Method for preparing chrysanthemum neolignan A from Huai chrysanthemum and application of method - Google Patents

Method for preparing chrysanthemum neolignan A from Huai chrysanthemum and application of method Download PDF

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CN109988206B
CN109988206B CN201910364966.6A CN201910364966A CN109988206B CN 109988206 B CN109988206 B CN 109988206B CN 201910364966 A CN201910364966 A CN 201910364966A CN 109988206 B CN109988206 B CN 109988206B
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李孟
曾梦楠
张靖柯
石静亚
吕锦锦
王洋洋
郑晓珂
冯卫生
孙彦君
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Henan University of Traditional Chinese Medicine HUTCM
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Abstract

The invention relates to a method for preparing chrysanthemum neolignan A from Huai chrysanthemum and application thereof, which effectively solves the problems of extracting chrysanthemum neolignan A from Huai chrysanthemum and realizing the application of the chrysanthemum neolignan A as a unique active ingredient in the preparation of anti-inflammatory drugs, 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 sub-fraction Fr.3.1 under reduced pressure, loading on MCI column, gradient eluting with water and methanol to obtain sub-fraction Fr.3.1.6, subjecting to Toyopearl HW-40 column chromatography, eluting with methanol, spray-identifying with anisaldehyde-concentrated sulfuric acid, mixing the same fractions to obtain sub-fraction Fr.3.1.6.2, separating with semi-preparative HPLC, loading on chromatographic column, and collecting retention time tRAnd (3) concentrating and drying the fraction of which the speed is 61.0-63.0 min to obtain the compound chrysanthemum neolignan A.

Description

Method for preparing chrysanthemum neolignan A from Huai chrysanthemum and application of method
Technical Field
The invention relates to medicine, in particular to a method for preparing chrysanthemum neolignan 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 enters lung and liver channels, and has effects of dispelling wind and heat, suppressing hyperactive liver, improving eyesight, clearing heat and detoxicating[1,2]. 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. Chrysanthemum morifolium (Dendranthema morifolium (Ramat.) kitam)]As one of the four major Huai drugs, the traditional Chinese medicine is mainly produced in Wu\38495in Henan, Wen county and has a long planting history, and is one of medicinal materials in the south China of the 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 neolignanoid A, is separated and identified from the Huai chrysanthemum. Experimental results show that the chrysanthemum neolignanoid 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 neolignan A from Huai chrysanthemum and application thereof, which can effectively solve the problems of extracting chrysanthemum neolignan A from Huai chrysanthemum and realizing application of chrysanthemum neolignan A as a unique active ingredient in preparing anti-inflammatory drugs.
The technical scheme for solving the problem is that the method for preparing the chrysanthemum neolignan A from the Huai chrysanthemum is an active ingredient extracted from the Huai chrysanthemum, and the molecular structural formula is as follows:
Figure BDA0002047882800000011
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; subjecting the sub-fraction Fr.3.1.6 to Toyopearl HW-40 column chromatography, eluting with methanol, spray-detecting with anisaldehyde-concentrated sulfuric acid once per 10mL, and mixing the same fractions to obtain sub-fraction Fr.3.1.6.1-Fr.3.1.6.2; separating the sub-fraction Fr.3.1.6.2 by semi-preparative HPLC, subjecting to chromatographic column with acetonitrile: trifluoroacetic acid water solution as mobile phase, and collecting retention time tRConcentrating and drying the fluid parts of 61.0-63.0 min to obtain the compound chrysanthemum neolignan A.
The compound, namely the chrysanthemum neolignan 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 the chrysanthemum neolignan A as a unique active ingredient in preparing the anti-inflammatory drugs.
The preparation method is easy to operate, scientific and reasonable, the prepared chrysanthemum neolignan A has the advantages that NO release of RAW264.7 cells induced by LPS is remarkably reduced, the chrysanthemum neolignan A is effectively used for preparing the anti-inflammatory drug, the application of the chrysanthemum neolignan A serving as the only active component in preparing the anti-inflammatory drug is realized, a new approach of the anti-inflammatory drug is developed, the medicinal value and the commercial value of the Huai chrysanthemum are improved, and the method has remarkable economic and social benefits.
Drawings
FIG. 1 shows the preparation of the compound chrysanthemum neolignan A1H-NMR Spectroscopy (in CD)3OD) plot.
FIG. 2 shows the preparation of the compound chrysanthemum neolignan A13C-NMR Spectroscopy (in CD)3OD) plot.
FIG. 3 is DEPT 135 spectrum (in CD) of the compound of the present invention, chrysanthemum neolignan A3OD) plot.
FIG. 4 shows the preparation of the compound chrysanthemum neolignan A1H-1H COSY spectra (in CD)3OD) plot.
FIG. 5 shows the HSQC spectrum (in CD) of the compound chrysanthemum neolignan A of the present invention3OD) plot.
FIG. 6 shows the HMBC (in CD) spectrum of the compound of the present invention, chrysanthemumneolignan A3OD) plot.
FIG. 7 shows NOESY spectra (in CD) of the compound of the present invention, chrysanthemumsinolignan A3OD) plot.
FIG. 8 is the HR-ESI-MS spectrum (in CD) of the compound chrysanthemum neolignan A of the present invention3OD) plot.
FIG. 9 shows the IR spectrum (in CD) of the compound of the present invention, chrysanthemumneolignan A3OD) plot.
FIG. 10 shows the UV spectrum (in CD) of the compound of the present invention, chrysanthemumlignan A3OD) plot.
Detailed Description
The following detailed description of the embodiments of the present invention refers to the accompanying drawings.
In the specific implementation of the invention, the method for preparing the chrysanthemum neolignan A from the Huai chrysanthemum is an active component extracted from the 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 adding water, 10% volume concentration and 20% volume concentrationEluting with% methanol, 30% methanol, 40% methanol and 100% methanol, wherein the amount of each eluting part is 10 times of the column volume, the flow rate is 3mL/min, spray-identifying with anisaldehyde-concentrated sulfuric acid, identifying once per 100mL, and mixing the same fractions to obtain a sub-fraction Fr.3.1.1-Fr.3.1.7; subjecting the sub-fraction Fr.3.1.6 to Toyopearl HW-40 column chromatography, eluting with 70% methanol by volume concentration, spray-identifying with anisaldehyde-concentrated sulfuric acid once per 10mL, and mixing the same fractions to obtain sub-fraction Fr.3.1.6.1-Fr.3.1.6.2; subfraction fr.3.1.6.2 was separated by semi-preparative HPLC with the above specification numbers: 250 x 10mm, particle size of 5 μm, and pore size of 12nm, wherein the mobile phase is acetonitrile: trifluoroacetic acid aqueous solution (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 t isRConcentrating and drying the fluid parts of 61.0-63.0 min to obtain the compound chrysanthemum neolignan A.
The compound, namely the chrysanthemum neolignan 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 the chrysanthemum neolignan A as a unique active ingredient in preparing the 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 neolignan 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.) kitam of Compositae by Cheng & Daizhizu Dai of Henan university of traditional Chinese medicine, and the compound chrysanthemum neolignanoid A is prepared according to the preparation method provided by the invention.
2 structural characterization
Chrysanthemum neolignan a: pale yellow crystalline powder (CH)3OH), anisaldehyde-concentrated sulfuric acid spray developing pink. HR-ESI-MS gives the peak M/z of the excimer ion 571.1771[ M + Na ]]+(calcd.For C27H32O12Na 571.1791), and determining its molecular formula as C27H32O12；UV(MeOH)λmax:206(2.42),228(0.59),284(0.23)nm；IR(KBr)νmaxcm-1：3361,2925,1674,1597,1443,1201,1123,1036cm-1。
Figure BDA0002047882800000041
Chrysanthemum neolignan A
TABLE 1 NMR spectroscopic data (in CD) of Chrysanthemum neolignan A3OD)
Figure BDA0002047882800000042
Figure BDA0002047882800000051
Activity detection
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 neolignan A group (50 mu M + LPS 1 mu g/mL) for further culture. 37 ℃ and 5% CO2After 24h incubation, 20. mu.L of MTT solution (5mg/mL) was added to each well, incubation was continued at 37 ℃ for 4h, the medium was carefully aspirated, and 100. mu.L of LDMS was added to each wellAnd O, shaking 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. 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 neolignan A group (50 mu M + LPS 1 mu g/mL) for further culture. 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 neolignan A group (50 mu M + LPS 1 mu g/mL) for further 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.
Active results
MTT and Griess results show that 1 mug/mL LPS can induce RAW264.7 cell proliferation and increase NO release, but chrysanthemum neolignan A (50 muM) can reduce NO release and does not kill RAW264.7 cells; 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 neolignanoid A (50 mu M), and the result shows that the chrysanthemum neolignanoid A has a good anti-inflammatory effect, is used as a unique active ingredient for remarkably reducing the release of NO by the RAW264.7 cells induced by the LPS, is effectively used for preparing anti-inflammatory drugs, develops a new way of the anti-inflammatory drugs and new application and commercial value of the Huai chrysanthemum, and has remarkable economic and social benefits.

Claims (1)

1. A method for preparing chrysanthemum neolignan A from Huai chrysanthemum is characterized in that the chrysanthemum neolignan A is an active ingredient extracted from Huai chrysanthemum and has a molecular structural formula as follows:
Figure FDA0003301498540000011
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; subjecting the sub-fraction Fr.3.1.6 to Toyopearl HW-40 column chromatography, eluting with 70% methanol by volume concentration, spray-identifying with anisaldehyde-concentrated sulfuric acid once per 10mL, and mixing the same fractions to obtain sub-fraction Fr.3.1.6.1-Fr.3.1.6.2; subfraction fr.3.1.6.2 was separated by semi-preparative HPLC with the above specification numbers: 250 multiplied by 10mm, a particle size of 5 mu m and a pore size of 12nm, wherein the mobile phase is acetonitrile: trifluoroacetic acid aqueous solution (23: 77), the mass concentration of the trifluoroacetic acid aqueous solution is two ten-thousandth, the flow rate is 3mL/min, fractions with retention time tR of 61.0-63.0 min are collected, and the fractions are concentrated and dried to obtain the compound chrysanthemum neolignan A.
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"Anti-inflammatory Lignans from the Fruits of Acanthopanax sessiliflorus";Dae-Young Lee等;《Molecules》;20131231;第18卷(第1期);第41-49页 *
"Sesamin Catechol Glucuronides Exert Anti-inflammatory Effects by Suppressing Interferon β and Inducible Nitric Oxide Synthase Expression through Deconjugation in Macrophage-like J774.1 Cells";Naomi Abe-Kanoh等;《J.Agric. Food Chem.》;20190405;第67卷(第27期);第7640-7649页 *

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