Compounds in Apricot-scented Rabbit-ear Wind and their preparation methods and applications

Abstract

The present application belongs to the field of medical technology, and discloses compounds in Apricot-scented Rabbit Ear Wind and its preparation method and application. The compound is compound 1 or compound 2. Apricot-scented Rabbit Ear Wind is extracted with alcohol, and petroleum ether, dichloromethane, ethyl acetate, and water are added for extraction respectively. The water-extracted part is first separated by resin, and then separated by silica gel column chromatography. The fractions from different parts are separated by preparative high-performance liquid chromatography to obtain the target compound 1 or compound 2. The preparation method of the compound of the present invention is simple to operate, and the compound in the Apricot-scented Rabbit Ear Wind can be separated. Experiments show that the compound of the present invention can effectively improve the death of AC16 human cardiomyocytes induced by doxorubicin and the disorder of GSH and inflammatory factor IL6. The present invention provides that the compound has a good protective effect on myocardial damage, has little toxic side effects, and can be used for the preparation of anti-myocarditis drugs.

Description

Technical Field

[0001] The invention belongs to the technical field of medicine, and in particular relates to a compound in apricot-scented rabbit ear herb and a preparation method and application thereof. Background Art

[0002] With the development of medical technology, malignant tumors, as one of the serious fatal diseases, have been prevented and treated to a certain extent. However, the resulting cardiotoxicity problem has become increasingly prominent. Epidemiological studies have shown that cardiovascular disease has become the main cause of death in elderly patients with malignant tumors undergoing chemotherapy. Currently, anthracyclines are widely used anti-tumor drugs in clinical practice, but the cardiotoxicity caused by these drugs has become the main obstacle to their clinical application. Studies have found that some Chinese medicines can not only prevent and treat cardiotoxicity, but also reduce the heart damage caused by anthracycline treatment. In terms of myocardial protection, Chinese medicine reduces myocardial ischemia-reperfusion injury, resists oxidative stress, improves myocardial remodeling and regulates cell apoptosis. These effects not only provide new treatment options for patients with heart disease, but also open up broader prospects for the application of traditional Chinese medicine in the treatment of malignant tumors.

[0003] Apricot scented rabbit ear wind Ainsliaea fragrans Champ. It is a perennial herb of the genus Rhizoma in the Asteraceae family. It has the effects of clearing away heat and detoxifying, eliminating accumulation and dispersing knots, relieving cough and stopping bleeding. Summary of the invention

[0004] The purpose of the present invention is to conduct in-depth research on the chemical components of apricot-scented rabbit ear wind, provide compounds in apricot-scented rabbit ear wind and their preparation methods and applications. The research found that the compounds of the present invention have a good protective effect on myocardial injury.

[0005] The technical solution of the present invention is as follows:

[0006] The compound in Ainslinine is compound 1 (named Ainslinine C) or compound 2 (named Ainslinine D), and its chemical structure is as follows:

[0007] .

[0008] The present invention also provides a method for preparing the compounds in the apricot-scented rabbit ear wind, comprising the following steps:

[0009] (1) Take the whole herb of Psoralea corylifolia and add ethanol solution for extraction to obtain an extract;

[0010] (2) Concentrate the extract until it has no alcohol taste, and then add petroleum ether, dichloromethane, ethyl acetate, and water to extract the extracts to obtain the extracts;

[0011] (3) The water extraction fraction obtained in step (2) was dissolved in methanol, separated by DAION HP20 resin, and eluted with water, 30% ethanol aqueous solution, 60% ethanol aqueous solution, and 90% ethanol aqueous solution in sequence to obtain corresponding fractions;

[0012] (4) taking the fraction eluted with 30% ethanol aqueous solution in step (3), dissolving it with methanol, dry-mixing it with silica gel (100-200 mesh), loading it onto a pre-filled silica gel (100-200 mesh) column, performing column chromatography separation, gradient eluting with dichloromethane-methanol (volume ratio of 100:0, 85:1, 50:1, 25:1, 10:1, 5:1, 0:100), and detecting it with high performance liquid chromatography, combining the fractions with similar liquid phase spectra to obtain 15 fractions 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15;

[0013] (5) The fraction 13 obtained in step (4) was dissolved in methanol and separated by preparative high performance liquid chromatography using acetonitrile-0.1% formic acid aqueous solution (volume ratio 22:78) as the mobile phase and isocratic elution at a flow rate of 10 ml / min with a retention time of 38 min to obtain the target compound 1;

[0014] (6) Fraction 14 from step (4) was dissolved in methanol and separated by preparative HPLC using acetonitrile-0.1% formic acid aqueous solution (volume ratio 25:75) as the mobile phase. Isocratic elution was performed at a flow rate of 10 ml / min with a retention time of 45 min to obtain the target compound 2.

[0015] Preferably, the extraction method in step (1) is cold soaking, percolation, microwave extraction, ultrasonic extraction or reflux extraction. More preferably, reflux extraction is performed twice, each time for 2 hours, and the extraction temperature is 70-90°C.

[0016] Preferably, the ethanol solution used in step (1) is an ethanol aqueous solution with a volume concentration of 5% to 95%, more preferably a 65% ethanol aqueous solution. The amount of ethanol aqueous solution added during extraction is 5 to 50 times the volume of the medicinal material, more preferably 15 times.

[0017] Preferably, in step (4), the mass ratio of the fraction obtained from the 30% ethanol aqueous solution elution portion to the silica gel used for sample mixing is 1:2.2.

[0018] The present invention also provides the use of the compound in the apricot-scented radix scutellariae in preparing a drug for preventing myocardial injury.

[0019] The invention also provides a pharmaceutical composition, comprising the compounds in the apricot-scented radix scutellariae.

[0020] The present invention also provides a pharmaceutical preparation, comprising a therapeutically effective amount of a compound in the herb Herba Lysimachiae and a pharmaceutically acceptable carrier or adjuvant thereof.

[0021] Those skilled in the art can directly or indirectly add the compound to various commonly used pharmaceutically acceptable excipients required for preparing different dosage forms, such as fillers, disintegrants, lubricants, adhesives, etc., and prepare commonly used oral preparations or injection preparations using conventional pharmaceutical preparation methods.

[0022] Preferably, the oral preparation is a tablet, a capsule, a granule, a fat emulsion, a microcapsule, or a pill.

[0023] Preferably, the injection preparation is an injection solution or a powder injection.

[0024] The beneficial effects of the present invention are:

[0025] The preparation method of the compound of the present invention is simple to operate, and can separate and obtain the compounds Ainslinine C and Ainslinine D in the apricot-scented radix scutellariae.

[0026] Experiments show that the compound of the present invention can effectively improve the vitality and GSH level of human AC16 cardiomyocyte damage induced by adriamycin and inhibit the level of inflammatory factor IL6, and has an anti-myocardial injury effect. The present invention provides that the compound has a good protective effect on myocardial injury, has little toxic side effects, and can be used for the preparation of anti-myocarditis drugs. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 is the chemical structural formula of the compound of the present invention;

[0028] Figure 2 is the mass spectrum of compound 1 of the present invention;

[0029] Figure 3 is the mass spectrum of compound 2 of the present invention;

[0030] Figure 4 The compound 1 of the present invention 1 H-NMR spectrum;

[0031] Figure 5 The compound 1 of the present invention 13 C-NMR spectrum;

[0032] Figure 6 is the DEPT spectrum of compound 1 of the present invention;

[0033] Figure 7 is the HSQC spectrum of compound 1 of the present invention;

[0034] Figure 8is the HMBC spectrum of compound 1 of the present invention;

[0035] Figure 9 The compound 1 of the present invention 1 H- 1 H COSY spectrum;

[0036] Figure 10 is the NOESY spectrum of compound 1 of the present invention;

[0037] Figure 11 The compound 2 of the present invention 1 H-NMR spectrum;

[0038] Figure 12 The compound 2 of the present invention 13 C-NMR spectrum;

[0039] Figure 13 is the DEPT spectrum of compound 2 of the present invention;

[0040] Figure 14 is the HSQC spectrum of compound 2 of the present invention;

[0041] Figure 15 is the HMBC spectrum of compound 2 of the present invention;

[0042] Figure 16 The compound 2 of the present invention 1 H- 1 H COSY spectrum;

[0043] Figure 17 It is the NOESY spectrum of compound 2 of the present invention. DETAILED DESCRIPTION

[0044] The technical solutions in the embodiments of the present invention are described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0045] Unless otherwise specified, the reagents involved in the embodiments of the present invention are all commercially available products and can be purchased through commercial channels.

[0046] Example 1 Preparation of Compounds

[0047] This example provides a method for preparing a compound in Apricot-scented Tuerfeng, the steps are:

[0048] (1) Take the whole herb of Psoralea corylifolia, add 15 times the volume of 65% ethanol solution, reflux and extract twice, each time for 2 hours, to obtain the extract;

[0049] (2) Concentrate the extract until it has no alcohol taste, and then add petroleum ether, dichloromethane, ethyl acetate, and water to extract the extracts to obtain the extracts;

[0050] (3) The water extraction fraction obtained in step (2) was dissolved in methanol, separated by DAION HP20 macroporous adsorption resin, and eluted with water, 30% ethanol aqueous solution, 60% ethanol aqueous solution, and 90% ethanol aqueous solution in sequence to obtain corresponding fractions;

[0051] (4) taking the fraction eluted with 30% ethanol aqueous solution in step (3), dissolving it with methanol, dry-mixing it with silica gel (100-200 mesh), loading it onto a pre-filled silica gel (100-200 mesh) column, performing column chromatography separation, gradient eluting with dichloromethane-methanol (volume ratio of 100:0, 85:1, 50:1, 25:1, 10:1, 5:1, 0:100), and detecting it with high performance liquid chromatography, combining the fractions with similar liquid phase spectra to obtain 15 fractions 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15;

[0052] (5) The fraction 13 obtained in step (4) was dissolved in methanol and separated by preparative high performance liquid chromatography using acetonitrile-0.1% formic acid aqueous solution (volume ratio 22:78) as the mobile phase and isocratic elution at a flow rate of 10 ml / min with a retention time of 38 min to obtain the target compound 1;

[0053] (6) Fraction 14 from step (4) was dissolved in methanol and separated by preparative HPLC using acetonitrile-0.1% formic acid aqueous solution (volume ratio 25:75) as the mobile phase. Isocratic elution was performed at a flow rate of 10 ml / min with a retention time of 45 min to obtain the target compound 2.

[0054] 1. Structural analysis and identification of compounds

[0055] Structural analysis of compounds: mainly using spectroscopy techniques, including mass spectrometry, nuclear magnetic resonance ( 1 H-NMR, 13 C-NMR, 2D-NMR) to identify its structure, the specific spectrum is as follows Figure 2~Figure 17 As shown, the spectral data and analysis process are as follows:

[0056] 1. Compound 1

[0057] (1) Compound 1 is a white powder. ESI-MS m / z 604.2232 [M+HCOO] - , whose molecular formula is C 26H 33 N5O9, its unsaturation is calculated to be 13.

[0058] Comprehensive analysis 1 H-NMR, 13 C-NMR shows that the compound has a glucose carbon signal (δc103.1, δc 77.3, δc 77.3, δc 74.0, δc 70.6, δc 61.6); 4 methylene groups (δc 42.5, δc 37.3, δc35.1, δc 31.5); 6 methylene groups (δc 83.5, δc 79.7, δc 49.2, δc 46.6, δc 45.6, δc 43.5), 2 carbonyl groups ( d c 175.9, d c 157.4), 8 unsaturated double bond carbons ( d c 154.4, d c 150.6, d c 152.0, d c149.4, d c 137.9, d c 116.8, d c 113.3, d c 111.0). 1 sugar terminal hydrogen signal [ d H : 4.26, m, 1H;], 2 oxymethylene hydrogen signals [ d H : 4.44, t, 1H; 4.12, t, 1H]. Then, the planar structure of the compound was determined by combining two-dimensional NMR spectroscopy data such as HMBC, DEPT and HSQC spectra. The structural formula is as follows: Figure 1 The compound was named Ainslinine C.

[0059] (2) The spectral data are as follows:

[0060] 1 H-NMR (700 MHz, DMSO- d 6 ) d H 7.60 (1H, s, H-8'), 6.66 (2H, s, H-10'), 5.36 (1H, s, H a -15), 5.13 (1H, s, H b -15), 4.82 (1H, s, H a -14), 4.79 (1H, s,H b-14), 4.44 (1H, t, J = 7.6, 15.3, H-3), 4.26 (1H, m, H-1′′), 4.12 (1H, t, J = 10.4, 20.2, H-6), 3.67 (2H, s, H-13), 3.66 (1H, s, H a -6′′), 3.44 (1H, s, H b -6′′), 2.99 - 3.16 (4H, m, H-2′′ ~ H-5′′), 3.01 (1H, m, H-11), 2.78 (1H, m, H-1), 2.61 (1H, t, J = 9.5, 19.1 Hz, H-5), 2.25 (1H, m, H-7), 2.21 (1H, m, H a -9), 2.16, (1H, m, H a -2), 1.85 (1H, m, H b -9), 1.70 (1H, m, H b -2), 1.67 (1H, m, H b -8), 1.23 (1H, m, H a -8).

[0061] 13 C-NMR (176 MHz, DMSO- d 6 ) d C 175.9 (C-12), 157.4 (C-6′), 154.4 (C-2′), 152.0 (C-4′), 150.6 (C-4), 149.4 (C-10), 137.9 (C-8′), 116.8 (C-5′), 113.3 (C-14), 111.0 (C-15), 103.1 (C-1′′), 83.5 (C-6), 79.7 (C-3), 77.3 (C-3′′), 77.3 (C-5′′), 74.0 (C-2′′), 70.6 (C-4′′), 61.6 (C-6′′), 49.2 (C-5), 46.6 (C-11), 45.6 (C-7), 43.5 (C-1), 42.5 (C-13), 37.3 (C-2), 35.1 (C-9), 31.5 (C-8).

[0062] 2. Compound 2

[0063] (1) Compound 2, white powder. ESI-MS m / z 588.2303 [M+HCOO] - , whose molecular formula is C 26 H 33 N5O8, its unsaturation is calculated to be 13. Comprehensive analysis 1 H-NMR, 13 C-NMR, it can be concluded that the compound structure has a group of glucose carbon signals ( d c 102.7, d c 76.9, d c 76.9, d c 73.6, d c 70.2, d c 61.2); 4 methylene groups ( d c 41.7, d c36.8, d c 35.2, d c 31.3); 6 methylene groups ( d c 83.0, d c 79.3, d c 48.6, d c 46.3, d c 45.2, d c43.0); 1 carbonyl d c 175.6; 9 unsaturated double bond carbons ( d c 156.0, d c 152.7, d c151.4, d c 150.2, d c149.0, d c 141.1, d c 118.5, d c 112.9, d c 110.5). 1 sugar terminal hydrogen signal [ d H : 4.26, d, 1H;], 2 oxymethylene hydrogen signals [ d H : 4.45, t, 1H; 4.12, t, 1H]. Then, the planar structure of the compound was determined by combining two-dimensional NMR spectroscopy data such as HMBC, DEPT and HSQC spectra. The structural formula is as follows: Figure 1 The compound was named Ainslinine D.

[0064] (2) The spectral data are as follows:

[0065] 1 H-NMR (700 MHz, DMSO- d 6 ) d H 8.16 (1H, s, H-2’), 8.06 (1H, s, H-8’),7.25 (2H, s, H-9’), 5.36 (1H, s, H a -8), 5.12 (1H, s, H b -8), 4.82 (1H, s, H a -14), 4.78(1H, s, H b -14), 4.45 (1H, t, J= 6.1, 12.5, H-3), 4.38 (2H, m,H-13),4.26 (1H, d, J =7.7, H-1′′), 4.12 (1H, t, J= 9.7, 19.5, H-6), 3.67 (1H, dd, J =5.9,11.6, 6′′ a ), 3.42 (1H, s, 6′′ b ), 2.98~3.15 (4H, m, H-2′′~ H-5′′), 3.02(1H, m, H-11), 2.75 (1H, m, H-1), 2.62(1H, t, J =9.8, 19.4 Hz, H-5), 2.28(1H,m, H-7), 2.22 (1H, m, H a -9), 2.17, (1H, m, H a -2), 1.82(1H, m, H b -9), 1.71 (1H,m, H b -2), 1.69(1H, m, H b -8), 1.30(1H, m, H a -8)。

[0066] 13 C-NMR (176 MHz, DMSO- d 6 ) d C175.6 (C-12), 156.0 (C-6′), 152.7(C-2′),151.4(C-4′),150.2(C-4),149.0(C-10),141.1(C-8′),118.5(C-5′),112.9(C-14),110.5(C-15), 102.7 (C-1′′), 83.0 (C-6), 79.3(C-3), 76.9 (C-3′′), 76.9 (C-5′′),73.6 (C-2′′), 70.2 (C-4′′), 61.2(C-6′′),48.6(C-5),46.3 (C-11), 45.2(C-7),43.0 (C-1), 41.7(C-13), 36.8(C-2), 35.2(C-9), 31.3(C-8).

[0067] 2. Experimental study of drug activity

[0068] 1. Experimental Materials and Animals

[0069] 1. Drugs and reagents

[0070] Compound 1 and compound 2 prepared in Example 1 (self-extracted, purity above 98%); DMEM / F12 high glucose medium (Suzhou Haixing Biotechnology Co., Ltd.), CCK-8 cell proliferation and toxicity detection kit (Beijing Solebold Technology Co., Ltd.), AC16 cells (Suzhou Haixing Biotechnology Co., Ltd.), fetal bovine serum (Beijing Solebold Technology Co., Ltd.), doxorubicin (DOX, MedChemExpress), SteadyPure rapid RNA extraction kit (Hunan Aikerui Biotechnology Co., Ltd.), Hifair AdvanceFast 1st Strand cDNA Synthesis SuperMix for qPCR (Yisheng Biotechnology Co., Ltd.), SYBR Green Premix Pro Taq HS qPCR Kit (Hunan Aikerui Biotechnology Co., Ltd.), mRNA primers (Hunan Aikerui Biotechnology Co., Ltd.).

[0071] 2. Experimental instruments

[0072] Inverted electron microscope (OLYMPUS, Japan: CKX41), microplate reader (Molecular Devices, USA: SpectraMax i3), MCV-B161S (T) clean bench (SANYO, Japan), MCO-20ACI CO2 constant temperature incubator (Thermo, USA), BS125S 1 / 10,000 balance (Mettler-Toledo, Switzerland), TDL-5C desktop microcentrifuge (Eppendorf, Germany), qTOWER3 real-time fluorescence quantitative PCR instrument (Jena).

[0073] 2. Experimental methods

[0074] 1. Cytotoxicity test of the compound prepared in Example 1

[0075] First, add the cell suspension containing AC16 cells into the culture flask, and then add 10 mL of DMEM / F12 high-glucose medium containing 10% fetal bovine serum that has been prepared in advance. Place it in an incubator at 37°C and 5% CO2, and operate aseptically throughout the process. Observe the cell morphology and growth closely every day. After the cell density is qualified under the microscope, take the AC16 cells in the logarithmic growth phase and incubate them at 5×10 4 The cells were inoculated at a density of 1.5 cells / well in a 96-well plate and administered after culturing for 24 hours, namely, a blank group and a drug-administered group (100µM and 200µM compound). After culturing for another 24 hours, the culture medium was discarded and 100µl of DMEM / F12 solution containing 10% CCK-8 was added to each well. After culturing for another 2 hours, the absorbance was detected at a wavelength of 450nm on a microplate reader and the cell survival rate was calculated.

[0076] 2. Study on the effect of the compound prepared in Example 1 on AC16 cell damage induced by doxorubicin (DOX)

[0077] First, add the cell suspension containing AC16 cells into the culture flask, and then add 10 mL of DMEM / F12 high-glucose medium containing 10% fetal bovine serum that has been prepared in advance. Place it in an incubator at 37°C and 5% CO2, and operate aseptically throughout the process. Observe the cell morphology and growth closely every day. After the cell density is qualified under the microscope, take AC16 cells in the logarithmic growth phase and culture them at 5×10 4 / well were inoculated in a 24-well plate. After culturing for 24 hours, the cells were divided into blank group, model group and drug-treated group. Different concentrations of compounds (100µM, 200µM) were added to the drug-treated group, and the same amount of culture medium was added to the blank group. After 2 hours, except for the blank group, appropriate amount of DOX was added to the other groups to make the final concentration of 1µM. After culturing for another 24 hours, the culture medium was discarded, and 100µl of DMEM / F12 high-glucose culture medium containing 10% CCK-8 was added to each well. After culturing for another 2 hours, the absorbance was detected at a wavelength of 450nm on a microplate reader and the cell survival rate was calculated.

[0078] 3. Study on the effect of the compound prepared in Example 1 on the GSH level in AC16 cells induced by doxorubicin (DOX)

[0079] First, add the cell suspension containing AC16 cells into the culture flask, and then add 10 mL of DMEM / F12 high-glucose medium containing 10% fetal bovine serum that has been prepared in advance. Place it in an incubator at 37°C and 5% CO2, and operate aseptically throughout the process. Observe the cell morphology and growth closely every day. After the cell density is qualified under the microscope, take AC16 cells in the logarithmic growth phase and culture them at 5×10 4 / well were inoculated in a 24-well plate. After culturing for 24 hours, the cells were divided into blank group, model group and drug-treated group. Different concentrations of compounds (100µM, 200µM) were added to the drug-treated group, and the same amount of culture medium was added to the blank group. After 2 hours, except for the blank group, appropriate amount of DOX was added to the other groups to make the final concentration of 1µM. After culturing for another 24 hours, the culture medium was discarded, and 100µl of DMEM / F12 high-glucose culture medium containing 10% CCK-8 was added to each well. After culturing for another 2 hours, the absorbance was detected at a wavelength of 450nm on a microplate reader and the cell survival rate was calculated.

[0080] 4. Study on the effect of the compound prepared in Example 1 on the IL-6 mRNA level in AC16 cells induced by doxorubicin (DOX)

[0081] First, add 5 mL of DMEM / F12 high-glucose medium containing 10% fetal bovine serum into a T75 culture flask, and then add the cell suspension of AC16 cells. Place the flask in an incubator at 37°C and 5% CO2, and culture it under aseptic conditions throughout the process. Observe the cell morphology and growth until the cell density is appropriate. Then, take AC16 cells in the logarithmic growth phase and seed them into 24 wells, with 1×10 cells per well. 5cells, and the drug was administered when about 80% of the cells were cultured. The cells were divided into a blank group, a model group, and a drug group. The drug group was added with 1 mL of medium containing the compound (100µM, 200µM), and the blank group was added with an equal amount of medium. After 2 h, except for the blank group, the remaining groups were added with an appropriate amount of AC16 to make the final concentration 1 μM. After 24 h of continuous culture, the cell RNA was extracted using the SteadyPure Rapid RNA Extraction Kit, and then the RNA was reverse transcribed into cDNA using the Hifair AdvanceFast 1st Strand cDNA Synthesis SuperMix forqPCR. The SYBR Green PremixPro Taq HS qPCR Kit reagent was used for quantification, the qPCR reaction system was configured, and the PCR reaction program was set. After the reaction was completed, the data was copied to an Excel spreadsheet for data processing, and the data were statistically analyzed using Graghpad Prism 8.

[0082] (III) Experimental results

[0083] 1. It can be seen from Table 1 and Table 2 that Compound 1 and Compound 2 prepared in Example 1 have no obvious toxicity to AC16 cells and have a protective effect on the death of AC16 cells induced by DOX.

[0084] Table 1 Results of cytotoxicity test of compound 1 and compound 2 on AC16 cells

[0085]

[0086] Table 2 Effects of Compound 1 and Compound 2 on the viability of AC16 cells induced by DOX

[0087]

[0088] 2. Effects of Compound 1 and Compound 2 prepared in Example 1 on the IL-6 gene expression level of AC16 cells induced by DOX. The results are shown in Table 3, which show that the prepared Compound 1 and Compound 2 had no obvious growth inhibitory effect on AC16 cells.

[0089] Table 3 Effects of Compound 1 and Compound 2 on IL-6 mRNA levels in AC16 cells induced by DOX

[0090]

[0091] 3. Effects of Compound 1 and Compound 2 prepared in Example 1 on the GSH level of AC16 cells induced by DOX. The results are shown in Table 4, which shows that the prepared Compound 1 and Compound 2 have a significant protective effect on the DOX-induced AC16 cell myocardial injury model, and have an inhibitory effect on IL-6 mRNA expression and an increasing effect on GSH levels, suggesting that they have an anti-myocardial injury effect.

[0092] Table 4 Effects of Compound 1 and Compound 2 on GSH levels in AC16 cells induced by DOX

[0093]

[0094] Finally, it should be noted that the above is only a preferred embodiment of the present invention and is not intended to limit the present invention. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art can still modify the technical solutions described in the aforementioned embodiments or replace some of the technical features therein by equivalents. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. The compound in the apricot-scented rabbit ear wind is characterized by: The compound is compound 1 or compound 2, and its chemical structure is as follows: 。 2. A method for preparing the compound in the apricot-scented rabbit ear wind according to claim 1, characterized in that: The following steps are involved: (1) Take the whole herb of Psoralea corylifolia and add ethanol solution for extraction to obtain an extract; (2) Concentrate the extract until it has no alcohol taste, and then add petroleum ether, dichloromethane, ethyl acetate, and water to extract the extracts to obtain the extracts; (3) dissolving the water extraction fraction obtained in step (2) with methanol, separating it with a macroporous adsorption resin, and eluting it with water, 30% ethanol aqueous solution, 60% ethanol aqueous solution, and 90% ethanol aqueous solution in sequence to obtain corresponding fractions; (4) Take the fraction eluted with 30% ethanol aqueous solution in step (3), dissolve it with methanol, mix it with silica gel dry method, load it into a pre-filled silica gel column, separate it by column chromatography, and use dichloromethane-methanol gradient elution with volume ratio of 100:0, 85:1, 50:1, 25:1, 10:1, 5:1, 0:100 to obtain 15 fractions 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15; (5) The fraction 13 obtained in step (4) was dissolved in methanol and separated by preparative high performance liquid chromatography using acetonitrile-0.1% formic acid aqueous solution in a volume ratio of 22:78 as the mobile phase for elution with a retention time of 38 min to obtain the target compound 1; (6) Fraction 14 obtained in step (4) was dissolved in methanol and separated by preparative HPLC using acetonitrile-0.1% formic acid aqueous solution in a volume ratio of 25:75 as the mobile phase with a retention time of 45 min to obtain the target compound 2.

3. The method for preparing the compound in the apricot-scented rabbit ear wind according to claim 2, characterized in that: In step (3), the macroporous adsorption resin is DAION HP20 resin.

4. The method for preparing the compound in the apricot-scented rabbit ear wind according to claim 2, characterized in that: In step (4), the silica gel used for sample mixing is 100-200 mesh, and the silica gel used in the silica gel column is 100-200 mesh.

5. The method for preparing the compound in the apricot-scented rabbit ear wind according to claim 2, characterized in that: In step (5) and step (6), the elution flow rate is 10 ml / min.

6. Use of the compound in the herb of claim 1 in the preparation of drugs for preventing myocardial injury.

7. A pharmaceutical composition, characterized in that: Comprising the compound described in claim 1.

8. A pharmaceutical preparation, characterized in that: The invention comprises a therapeutically effective amount of the compound according to claim 1 and a pharmaceutically acceptable carrier or auxiliary material.

9. The pharmaceutical preparation according to claim 8, characterized in that: The pharmaceutical preparation is an oral preparation or an injection preparation.

Images