CN108191936B - A neoline J and K extracted from semen Lepidii, and its preparation method and application - Google Patents
A neoline J and K extracted from semen Lepidii, and its preparation method and application Download PDFInfo
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Abstract
The invention relates to semen lepidiiExtracting parched semen Lepidii with water, concentrating, precipitating with ethanol, separating the supernatant with Dianion HP-20 column, eluting with water and ethanol, collecting 60% ethanol eluate, drying, dissolving with water, centrifuging, dissolving the precipitate with methanol, mixing with silica gel, eluting with dichloromethane-methanol, mixing with dichloromethane-methanol 5:1, purifying with ODS column chromatography, eluting with water and methanol, collecting 60% methanol eluate, separating with semi-preparative HPLC, collecting tRPassing the flow of the extract for = 10-30 min through a Sephadex LH-20 column chromatography, eluting with methanol, collecting the flow of the extract at 8 ml/tube, combining the flow of the extract at 18-35 tubes, passing through a YMC-Pack ODS-AA chromatographic column, eluting with an acetonitrile-trifluoroacetic acid aqueous solution, collecting the fractions tRThe fraction of 20.5-21.5 min is obtained to obtain the neoline northern pepperweed J; collecting tRAnd (4) carrying out fractionation for 28.4-27.3 min to obtain the neoline K. The invention has the advantages of rich raw materials, easy operation, science and reasonability.
Description
Technical Field
The invention relates to medicine, in particular to a neoline northern Ting J and a neoline northern Ting K extracted from semen lepidii, a preparation method and application thereof.
Background
Ting Li Zi is a commonly used Chinese medicinal material, originally recorded in Shen nong Ben Cao Jing, listed as the lower-grade herb of Ming Dynasty, and it is pungent, bitter, cold in nature, entering lung and bladder meridians, and has the effects of dispersing obstruction of qi, relieving asthma, promoting diuresis and relieving swelling. The Lepidium seed recorded in the 'Chinese pharmacopoeia' of 2015 edition has north and south, wherein the dry mature seed of Lepidium apetalum Willd. of the crucifer Lepidium is commonly called 'northern Lepidium seed', and the dry mature seed of Descurainia Sophia (L.) Webbex Prantl. is commonly called 'southern Lepidium seed'. With the intensive research on the semen lepidii, the semen lepidii is found to have good medicinal value and contain various active ingredients with medicinal effects, but how to prepare different active ingredients from the semen lepidii and prepare medicines for treating different diseases is a technical problem which is hoped to be solved in the industry all the time.
Disclosure of Invention
In view of the above situation, in order to overcome the defects of the prior art, the present invention aims to provide a northern pepperweed alkaloid J and a northern pepperweed alkaloid K extracted from northern pepperweed seed, and a preparation method and an application thereof, which can effectively solve the preparation of active ingredients of the northern pepperweed seed and realize the application in the preparation of drugs for treating myocardial cell (H9c2) injury caused by Lipopolysaccharide (LPS).
The technical scheme for solving the problem is that the molecular structural formulas of the northern pepperweed alkaloid J and the northern pepperweed alkaloid K extracted from the northern pepperweed seed are respectively as follows:
the preparation method comprises the following steps: parching semen Lepidii at 240 deg.C for 5.5min, adding 10 times of water by weight of semen Lepidii each time, decocting and extracting for three times, each time for 1.5 hr, mixing the three extractive solutions, concentrating under reduced pressure to obtain extract with crude drug content of 2g/mL, precipitating the concentrated extract with 80% ethanol with 5 times of the extract volume at room temperature, standing for 1 hr, collecting supernatant, adding 80% ethanol with 5 times of the extract volume, repeating the above steps for 4 times, concentrating the supernatant until no ethanol smell exists, purifying with Dianion HP-20 column, gradually eluting with 20%, 40% and 60% ethanol, flowing at 6mL/min, and collecting 60% ethanol with flow rate of 10 times of the column volumeRemoving liquid, concentrating, drying to obtain component A, dissolving with 5 times of water of component A, centrifuging at 6000rpm at 20 deg.C for 15min, collecting supernatant as water soluble component B1, precipitating as water insoluble component B2, dissolving component B2 with methanol, dissolving component B2 methanol solution, mixing with silica gel, detecting component B2 methanol solution and silica gel at 1:1 ratio, gradient eluting with dichloromethane and methanol at flow rate of 10mL/min, gradient ratio of 100:0, 20:1, 10:1, 5:1, 1:1, every 200mL, detecting the end point of each gradient mobile phase with anisaldehyde-concentrated sulfuric acid thin layer chromatography, after 3D is finished, mixing dichloromethane and methanol at flow rate of 5:1, detecting component C4, dissolving component C567 with water, passing through ODS column, detecting with water, volume concentration of 10%, 20%, 30%, 60% methanol at flow rate of 3mL/min, detecting anisaldehyde at flow rate of 3-5: 1, detecting component C5, mixing with acetic acid at flow rate of 3525 mL-3525 mL, detecting acetic acid at 3525 mL, collecting eluate with acetic acid at 3525 mL, and detecting acetic acid by HPLC column chromatography, and collecting aqueous solution with acetic acid chromatography, and detecting acetic acid chromatography, wherein the flow rate of each gradient chromatography is equal to obtain acetic acid chromatography, and the concentration of each column is equal to obtain eluent, and the concentration of 10mL, and the concentration of acetic acid chromatography is equal to obtain eluent, and the concentration of 10mL, and the concentration of 10-20 mm, and the concentration of the concentrationR10-30 min fraction designated as component E1, passing fraction E1 through Sephadex LH-20 column chromatography, eluting with methanol at a flow rate of 1mL/min, taking the fraction from a test tube, taking each 8mL fraction as one tube, performing thin-layer detection on the fraction in the test tube by anisaldehyde-concentrated sulfuric acid to judge an elution end point, combining the fractions in 18-35 tubes designated as component F2, passing fraction F2 through semi-preparative HPLC, wherein the upper specification is 250 × 10mm, the particle size is 5 μm, and the pore size is 12nm, the mobile phase is acetonitrile, trifluoroacetic acid aqueous solution 11: 89, the flow rate is 2.5mL/min, and collecting the retention time tRConcentrating and drying the fraction of 20.5-21.5 min to obtain a compound, namely, norseselin J; collecting the retention time tRConcentrating and drying the fluid fraction of 28.4-27.3 min to obtain the compound of the neotame K.
Two novel uridine derivatives were isolated and identified from an aqueous extract of semen lepidii, namely: the neoline northern Ting J and the neoline northern Ting K have the functions of improving the cell activity of myocardial cell (H9c2) damage caused by Lipopolysaccharide (LPS) and potential myocardial protection, and can be effectively used for preparing the medicine for treating myocardial cell (H9c2) damage caused by Lipopolysaccharide (LPS).
The invention has rich raw materials, easy operation of the preparation method, and scientific and reasonable, can effectively solve the problem of extracting the northern pepperweed alkaloid J and the northern pepperweed alkaloid K from the northern pepperweed seed, realizes the application of the northern pepperweed alkaloid J and the northern pepperweed alkaloid K in the preparation of the cell viability medicament for causing the myocardial cell (H9c2) damage by Lipopolysaccharide (LPS), exploits the medicinal value and the commercial value of the northern pepperweed seed, and has obvious economic and social benefits.
Drawings
FIG. 1 is a molecular structural diagram of the present invention.
FIG. 2 is a drawing of the compound of the present invention, norsesamin J1H-NMR Spectroscopy (in CD)3OD) plot.
FIG. 3 is a drawing of a compound of the present invention, norsesamin J1H-1H COSY spectrum.
FIG. 4 is an HSQC spectrum of the compound of the present invention, northern pepperweed alkaloid J.
FIG. 5 is an HMBC spectrum of the compound of the invention, northern pepperweed base J.
FIG. 6 is a NOESY spectrum of the compound of the invention, northern pepperweed alkaloid J.
FIG. 7 is a HRESIMS spectrum of the compound of the invention, northern pepperweed alkaloid J.
FIG. 8 shows the preparation of the compound of northern pepperweed alkaloid K1H-NMR Spectroscopy (incD)3OD) plot.
FIG. 9 shows the preparation of the compound of northern pepperweed alkaloid K1H-1H COSY spectrum.
FIG. 10 is an HSQC spectrum of the compound of the present invention, northern pepperweed base K.
FIG. 11 is an HMBC spectrum of the compound of the invention, northern pepperweed base K.
FIG. 12 is a NOESY spectrum of the compound of the invention, northern pepperweed alkaloid K.
FIG. 13 is a HRESIMS spectrum of the compound of northern pepperweed alkaloid K of the present invention.
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 molecular structural formulas of the northern pepperweed alkaloid J and the northern pepperweed alkaloid K extracted from the northern pepperweed seed are respectively as follows:
the preparation method comprises parching semen Lepidii 10kg with clear parching method to 240 deg.C, parching for 5.5min, decocting with 100kg water for three times each for 1.5 hr, mixing extractive solutions, concentrating under reduced pressure to 5000mL extract, precipitating concentrated extract with 80% ethanol 25L at room temperature, standing for 1 hr, collecting supernatant, adding 80% ethanol 25L, precipitating with ethanol for 4 times, concentrating the supernatant to no ethanol smell, subjecting to Dianion HP-20 column, eluting with water, 20% ethanol 40% ethanol and 60% ethanol in sequence at flow rate of 6mL/min, collecting eluate with mobile phase 10 times of the column volume, concentrating, drying to obtain component A, dissolving component A in 5 times of water, centrifuging at 20 deg.C at 6000rpm for 15min, dissolving component A in 5 times of water, collecting insoluble component B2, dissolving component B2 with methanol, ODS, eluting with silica gel at flow rate of 3563% and 250% methanol, eluting with methanol at flow rate of 351-20% and 20% methanol, mixing with ethanol, eluting components A, eluting with ethanol of 3535-20% and 35% methanol, eluting with chromatography column at flow rate of 351-20% methanol, eluting 5 mm, and chromatography, detecting that the flow rate of chromatography column for 3520 mm, detecting that the eluent is 3520% methanol, and the flow rate of a chromatography column for 10mm, and the eluent for 10% methanol, and the flow rate of a chromatography column, and a chromatography of a chromatography column, and a chromatography ofAcetonitrile: aqueous trifluoroacetic acid solution 25: 75, flow rate of 5mL/min, collection retention time tR10-30 min fraction designated as component E1, passing fraction E1 through Sephadex LH-20 column chromatography, eluting with methanol at a flow rate of 1mL/min, taking fraction from a test tube, taking each 8mL fraction as one tube, performing thin-layer chromatography on the fraction in the test tube by anisaldehyde-concentrated sulfuric acid to judge an elution end point, combining the fractions in 18-35 tubes designated as component F2, passing fraction F2 through semi-preparative HPLC, wherein the upper specification is 250 × 10mm, the particle size is 5 μm, and the pore size is 12nm, the mobile phase is acetonitrile-trifluoroacetic acid aqueous solution 11: 89, the flow rate is 2.5mL/min, and collecting retention time tRConcentrating and drying the fraction of 20.5-21.5 min to obtain a compound of norcochine J, and collecting the retention time tRConcentrating and drying the fluid fraction of 28.4-27.3 min to obtain the compound of the neotame K.
The invention also extracts the neoline J and the neoline K from the semen lepidii with different quantities, which have the same or similar results and are not detailed in detail.
The method is stable and reliable, the extracts are identified as the northern pepperweed alkaloid J and the northern pepperweed alkaloid K, and have the myocardial protection effect, and experiments prove that the northern pepperweed alkaloid J and the northern pepperweed alkaloid K can obviously improve the cell activity of myocardial cell (H9c2) damage caused by Lipopolysaccharide (LPS), have the myocardial protection effect, are effectively used for preparing the medicine for improving the cell activity of myocardial cell (H9c2) damage caused by Lipopolysaccharide (LPS), develop the medicinal value and the commercial value of the northern pepperweed seed, and obtain very good beneficial technical effects through field experiments and applications, and the related data are as follows:
1 apparatus
Bruker AVANCE III 500 NMR Spectrometer (TMS internal standard) (Bruker), Nicolet is 10 Microscope Spectrometer for infrared spectroscopy (Thermo Scientific, USA), Bruker maxis HD mass Spectrometer for high-resolution mass spectroscopy, Shimadzu UV-2401PC appaatus for ultraviolet spectroscopy, Chirascan qCD for circular dichroism (Applied photophysis Ltd, Britain), Waters alliance 2695 series high performance liquid chromatography, diode array detector 2998 type, Empower3 datA workstation, LC50 type high pressure preparative liquid chromatography, UV200 type UV detector [ Beijing Shakun spectrA Ltd ], YMC-Pack ODS-A column (250X 10mm. D.S-5 mm,12mm) (YMC Co., Ltd.), and the rest are N-1000 ocean atmospheric distillation apparatus (Hitachi S1000 S.S.A., Ltd.), an N-1111 type freezing water circulation device (Shanghai Elang apparatus Co., Ltd.), an FDU-2110 type freezing dryer (Shanghai Elang apparatus Co., Ltd.), a DFZ-60508 type vacuum drying box (Shanghai Yingsheng Scientific apparatus Co., Ltd.), an AB 204-Nten thousandth precision analytical balance (METTLER TOLEDO), an iMARK type microplate reader (U.S. BIO-RAD), a carbon dioxide incubator (Shanghai STIK), an ultra-clean bench (Sujing group), an Arium 611VF super-combination type super water purifier (SARTORIUS), an inverted microscope (Nikon), a PB-10 acidimeter (Germany Sedoristi group), and a 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-.
H9C2 rat cardiac cell line (shanghai cell bank of chinese academy of sciences); lipopolysaccharide (Sigma company); astragalus mongholicus injection (Heilongjiang treasure island pharmaceutical products Co., Ltd.); DMEM high-glucose medium (Gibco), fetal bovine serum (zhejiang hang biotechnology limited), trypsin (Gibco), dmso (solarbio); ampicillin, Tris base (Sigma); EDTA, MTT and dmso (amresco); water is ultrapure water, PBS buffer solution and the like are prepared by self.
In 2014, the semen lepidii is collected from south-Henan Yang and is identified as dry mature seeds of Lepidium apetalum Willd.
2 structural characterization
Neoline J: colorless crystalline powder (DMSO-d)6). HR-ESI-MS gives the peak M/z of the excimer ion 618.1566[ M + Na ]]+(calcd.For C25H29N3O14Na 618.1547), and determining its molecular formula as C25H29N3O14Na；
(c 0.01,MeOH)；UV(MeOH)λmax:208(0.53),258(0.21)nm；CD(MeOH):265(Δ+11.08)nm,239 (Δ-19.19)nm；IR(iTR)νmaxcm-1：3288,2927,2856,1674,1201,1022cm-1. The structural formula and nuclear magnetic data are as follows:
neoline K: colorless crystalline powder (CD)3OD). HR-ESI-MS gives the peak M/z of the excimer ion 618.1566[ M + Na ]]+(calcd.For C25H29N3O14Na 618.1547), and determining its molecular formula as C25H29N3O14Na；
(c 0.01,MeOH)；UV(MeOH)λmax:206(0.99),257(0.37)nm；CD(MeOH):240(Δ+16.65)nm,216(Δ-14.08)nm；IR(iTR)νmaxcm-1：3366,2926,2853,1676,1202,1135,723cm-1. The structural formula and nuclear magnetic data are as follows:
TABLE 1 BeiTing New base J (in CD)3OD) and neoline K (in CD)3OD) NMR data
According to the nuclear magnetic data, the structural formulas of the northern pepperweed alkaloid J and the northern pepperweed alkaloid K are as follows:
the pattern identification is shown in FIGS. 2-13 and will not be described in detail.
3 Activity assay
H9c2 cells according to 2 × 104Seeded in 96-well plates. LPS 1mg was weighed, dissolved in 10. mu.l of vehicle DMSO, and added to 1mL of DMEM-containing medium with a stock concentration of 1mg/mL of LPS and a final concentration of 20. mu.g/mL in a 96-well plate. The cells were divided into normal group, model group and different groups of drugs. After 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, 150. mu.L of LDMSO was added to each well, and the mixture was shaken for 10 min to completely dissolve the crystals. The number and viability of the cells were monitored by zeroing with DMSO and measuring the absorbance (A) of each well at 490nm using a microplate reader.
4 Activity results
Compared with the group M at 10 mu M, the OD value of the northern pepperweed alkaloid J and the northern pepperweed alkaloid K is obviously increased (P is less than 0.05), which indicates that the northern pepperweed alkaloid J and the northern pepperweed alkaloid K obviously improve the cell activity of the H9c2 injury caused by LPS and have potential myocardial protection effect. See table 2.
TABLE 2 Effect of northern Tilapine J and northern Tilapine K on LPS stimulation of H9c2 cell proliferation ((
n＝4)
Note that P represents P in comparison with the normal group<0.05, represents P<0.01; in comparison to the group of M,#represents P<0.05，##Represents P<0.01。
The experiments clearly show that the northern pepperweed alkaloid J and the northern pepperweed alkaloid K extracted by the invention have the myocardial protection effect, can be effectively used for preparing the medicine for treating myocardial cell (H9c2) damage caused by Lipopolysaccharide (LPS), develops the medicinal value and the commercial value of the northern pepperweed seed, and has obvious economic and social benefits.
Claims (2)
1. A northern pepperweed alkaloid J and northern pepperweed alkaloid K extracted from northern pepperweed seed are characterized in that the molecular structural formulas are respectively as follows:
wherein the preparation method of the neoline J and the neoline K comprises parching semen Lepidii at 240 deg.C for 5.5min, adding 10 times of water by weight of semen Lepidii each time, decocting for three times, each time for 1.5 hr, mixing the three extractive solutions, concentrating under reduced pressure to obtain extract with crude drug content of 2g/mL, precipitating the concentrated extract with 5 times of ethanol with volume concentration of 80% at room temperature, standing for 1 hr, collecting supernatant, adding 5 times of ethanol with volume concentration of 80% to precipitate with ethanol with volume concentration of 5 times of extract, repeating the above steps for 4 times, concentrating the obtained supernatant until no ethanol smell exists, loading on Dianion HP-20 column, gradually eluting with water, 20% of volume concentration, 40% of ethanol with volume concentration, and 60% of ethanol with flow rate of 6mL/min, collecting eluate with volume concentration of 60% of ethanol with volume concentration of 10 times of each part, concentrating, drying, obtaining a component A; adding water 5 times the weight of component A to dissolve, centrifuging at 20 deg.C and 6000rpm for 15min to obtain supernatant as water soluble component B1, and precipitating as water insoluble component B2; dissolving component B2 with methanol, mixing silica gel, gradient eluting component B2 methanol solution and silica gel at a flow rate of 10mL/min with dichloromethane-methanol as mobile phase at a ratio of 100:0, 20:1, 10:1, 5:1 and 1:1, every 200mL, determining elution end point with anisaldehyde-concentrated sulfuric acid thin layer, combining the eluates at 3d, dissolving component C4 with water, performing ODS column chromatography, sequentially eluting with water, eluting with silica gel at a ratio of 1:1, and eluting with dichloromethane-methanol at a flow rate of 10mL/min with each gradient mobile phase at a ratio of 100:0, 20:1, 10:1, 5:1, and mixing the eluates at a ratio of 5:1, wherein component C4 is obtained, dissolving component C4 with water, sequentially eluting with water, eluting with concentrated sulfuric acid, eluting with water,gradient eluting with 10%, 20%, 30%, 60% methanol at flow rate of 3mL/min, determining elution end point by anisaldehyde-concentrated sulfuric acid thin layer chromatography, once every 20mL, after 2D elution, mixing 60% methanol elution component to obtain component D5, separating component D5 with semi-preparative HPLC, wherein the upper specification is 250 × 20mm, the particle size is 5 μm, the pore size is 12nm, the mobile phase is YMC-Pack ODS-AA chromatographic column, the ratio of acetonitrile-trifluoroacetic acid water solution is 25: 75, the trifluoroacetic acid water solution is prepared by adding 300 μ l trifluoroacetic acid into 1000mL water, mixing, the flow rate is 5mL/min, collecting retention time t, and collecting retention time tR10-30 min fraction designated as component E1, passing fraction E1 through Sephadex LH-20 column chromatography, eluting with methanol at a flow rate of 1mL/min, taking fraction from a test tube, taking each 8mL fraction as one tube, performing thin-layer chromatography on the fraction in the test tube by anisaldehyde-concentrated sulfuric acid to judge an elution end point, combining the fractions in 18-35 tubes designated as component F2, passing fraction F2 through semi-preparative HPLC, wherein the upper specification is 250 × 10mm, the particle size is 5 μm, and the pore size is 12nm, the mobile phase is acetonitrile-trifluoroacetic acid aqueous solution 11: 89, the flow rate is 2.5mL/min, and collecting retention time tRConcentrating and drying the fraction of 20.5-21.5 min to obtain a compound, namely, norseselin J; collecting the retention time tRConcentrating and drying the fluid fraction of 28.4-27.3 min to obtain the compound of the neotame K.
2. The use of the northern pepperweed alkaloid J and northern pepperweed alkaloid K extracted from northern pepperweed seed as claimed in claim 1 in the preparation of medicament for treating myocardial cell injury caused by lipopolysaccharide.
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