CN112624928B - Anticoagulant peach blossom effective component and application thereof - Google Patents
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Abstract
The invention discloses an anticoagulant peach blossom effective component, which is obtained by extracting the following steps: extracting flos persicae with petroleum ether for defatting, filtering, recovering residue, extracting with ethanol at room temperature, filtering, and concentrating to obtain ethanol total extract; dispersing the ethanol total extract in a small amount of water to form a dispersion, sequentially extracting with solvents of petroleum ether, ethyl acetate and n-butanol, and recovering the solvents to obtain petroleum ether fraction, ethyl acetate fraction and n-butanol fraction; mixing n-butanol fraction with silica gel, subjecting to silica gel column chromatography, and gradient eluting with dichloromethane-methanol to obtain 8 components; mixing component 5 with silica gel, loading onto column, eluting with dichloromethane-ethyl acetate-methanol, detecting by thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure. The invention adopts a special method to separate 1 compound with anticoagulant activity from the n-butanol part of the peach blossom, and experimental results prove that the compound can be used as an anticoagulant reagent.
Description
Technical Field
The invention belongs to the technical field of plant extraction, and particularly relates to an anticoagulant peach blossom effective component and extraction application thereof.
Background
The flos Persicae is of Prunus of Rosaceae (Rosaceae)Amygdalus) Plant peaches (Amygdalus persica L. or mountain peach (Amygdalus davidiana) The flower of Chili has bitter taste and neutral nature, and has the effects of entering heart, liver and large intestine channels, facilitating water and relaxing bowels, and promoting blood circulation to remove blood stasis. At present, the chemical research on peach blossom is mostly focused on the extraction and purification process of polyphenol and the analysis of fat-soluble components, and the research results show that the peach blossom (peach blossom)Amygdalus persica) Benzaldehyde is identified in the volatile oil,α88 volatile components such as farnesene and hexadecanoic acid, and the peach blossom volatile oil is found to have strong inhibitory effect on 8 pathogenic bacteria such as salmonella typhi. However, peach (A)Amygdalus persica L) chemical composition of flowersAnd pharmacological effects remain uncertain without clear theoretical evidence.
Thrombosis involves local clotting of blood in the vascular system, often resulting in serious health-related diseases such as heart attack and stroke. Among the risk factors for thrombosis are abnormal hyperlipidemia, hyperglycemia, elevated plasma fibrinogen, hypertension and cancer, which have become the leading cause of death and the incidence of which is increasing every year. In recent decades, the aim of preventing and treating thrombus is achieved by using medicines such as heparin, warfarin and the like, but the heparin is easy to cause spontaneous bleeding which is manifested as various mucosal bleeding, joint bleeding, wound bleeding and the like. In addition, heparin-induced thrombocytopenia is drug-induced thrombocytopenia and is a serious complication of heparin therapy. Thus, these disadvantages have forced researchers to discover new antithrombotic and anticoagulant agents with fewer side effects than heparin.
The essence of blood coagulation is the process of converting water-soluble fibrinogen into water-insoluble solid fibrin, which is to generate prothrombin activator in the intrinsic and/or extrinsic coagulation pathway, generate thrombin by the action of coagulation factors, and finally convert fibrinogen into fibrin by the action of thrombin. PT mainly reflects the activity of coagulation factors I, II, V, VII and X in the extrinsic coagulation pathway; APTT mainly reflects the status of the intrinsic coagulation system and is related to the activity of intrinsic coagulation factors such as VIII, X, XI, XII and the like; the TT value is an important index mainly reflecting the degree of converting fibrinogen into fibrin; FIB mainly reflects fibrinogen content.
Disclosure of Invention
Based on the defects of the prior art, the invention aims to provide an anticoagulant peach blossom effective component, and provides an extraction and separation method and application of the anticoagulant peach blossom effective component.
In order to achieve the purpose, the invention adopts the technical scheme that:
an anticoagulant peach blossom effective component is obtained by the following steps:
1) Taking dried and crushed peach blossom as a raw material, leaching and degreasing with petroleum ether, filtering after the petroleum ether leaching is finished, recovering filter residue, leaching with ethanol at room temperature, filtering after the ethanol leaching is finished, and concentrating to obtain an ethanol total extract; dispersing the ethanol total extract in a small amount of water to form a dispersion, sequentially extracting with solvents of petroleum ether, ethyl acetate and n-butanol, and recovering the solvents to obtain petroleum ether fraction, ethyl acetate fraction and n-butanol fraction;
2) Mixing the n-butanol part obtained in the step 1) with silica gel, separating by 200-300 mesh silica gel column chromatography, performing gradient elution with dichloromethane-methanol, detecting and combining by silica gel thin layer chromatography to obtain 8 components, and sequentially marking as a component 1~8 according to the polarity of the obtained components from small to large;
3) Mixing component 5 with silica gel, separating by silica gel column chromatography, eluting with dichloromethane-ethyl acetate-methanol, detecting by silica gel thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain Fr.5.1;
4) Mixing Fr.5.1 obtained in step 3) with silica gel, loading onto column, separating with silica gel column chromatography, eluting with dichloromethane-methanol, detecting with silica gel thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain Fr.5.1.1;
5) Mixing Fr.5.1.1 obtained in the step 4) with silica gel, loading on a column, separating by silica gel column chromatography, eluting with dichloromethane-methanol, detecting by thin layer chromatography, mixing the same components, and recovering solvent under reduced pressure to obtain Fr.5.1.1.1; dissolving Fr.5.1.1.1 with methanol, purifying by Sephadex LH-20 gel column chromatography, eluting with methanol, detecting by thin layer chromatography, mixing the same components, recovering solvent under reduced pressure, and drying to obtain compound 1;
the compound 1 is the effective component of the anticoagulant peach blossom. Equivalently, the invention discloses a method for extracting and separating effective components of anticoagulant peach blossom.
Preferably, in the step 1), the dried and crushed peach blossom is extracted with petroleum ether which is 10-15 times of the weight of the peach blossom at room temperature for 2~4 times, 3 to 4 days each time; and then extracting the filter residue with ethanol (the addition amount of the ethanol is 10-15 times of the weight of the peach blossom) with the volume concentration of 70-80% at room temperature for 2~4 times (3-4 days each time), merging ethanol extract after the ethanol extraction is finished, filtering and concentrating to obtain the total ethanol extract.
Preferably, in the step 2), the n-butanol part is stirred and filled into a column by using 200 to 300-mesh silica gel according to the weight ratio of 1 to 1; the following components were eluted with a dichloromethane-methanol gradient of volume ratio 100.
Preferably, in the step 3), the component 5 is stirred and filled into a column by using 200 to 300-mesh silica gel according to a weight ratio of 1 to 29 to 1, and is eluted by using dichloromethane-ethyl acetate-methanol with a volume ratio of 15; in step 4), eluting with dichloromethane-methanol at a volume ratio of 20; in step 5), the mixture was eluted with dichloromethane-methanol at a volume ratio of 10.
The compound 1 of the anticoagulant peach blossom effective component is chlorogenic acid n-butyl ester, and the molecular formula is as follows: c 20 H 26 O 9 Molecular weight: 410, the structure is as follows:
the invention also provides application of the anticoagulant peach blossom effective component in preparation of anticoagulant drugs. The invention adopts a special method to separate 1 compound (chlorogenic acid n-butyl ester) with anticoagulant activity from the n-butyl alcohol part of the peach blossom, and the compound can be used as anticoagulant.
Compared with the prior art, the invention has the following beneficial effects:
the invention relates to peaches which are often used as ornamental fruits, discarded as wastes after flowering and not widely used (Amygdalus persica L.) flower is taken as a raw material, and anticoagulant active ingredients are extracted, so that the development and utilization value of the peach flower which is a medicinal plant is greatly expanded. The extraction method is simple, the raw material sources are rich, the cost is low, and the extracted compound has an anticoagulation effect and can be used as an anticoagulation reagent as proved by experiments; the solvent used in the extraction process can be recycled, the extraction amount is large, and the method can be used for industrial production.
Drawings
FIG. 1 shows that the compound chlorogenic acid n-butyl ester obtained by extraction in example 1 1 H-NMR spectrum;
FIG. 2 shows that the compound chlorogenic acid n-butyl ester extracted in example 1 13 C-NMR spectrum.
Detailed Description
In order to make the technical purpose, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention are further described with reference to specific examples, which are intended to explain the present invention and are not to be construed as limiting the present invention, and those who do not specify a specific technique or condition in the examples follow the techniques or conditions described in the literature in the art or follow the product specification.
In the following examples, peach blossom as a raw material was purchased from Anhui Yao Zhiyuan herbal pieces Limited, is prepared from Prunus persica (L.) Batsch. Of Prunus of Rosaceae)Amygdalus persica L.); the concentrations of the organic solvents such as ethanol, methanol, dichloromethane and the like are volume concentrations or volume ratios.
Example 1
The anticoagulant peach blossom effective component is obtained by extracting the following steps:
1) Taking dried and crushed 2000 g peach blossom as a raw material, leaching the peach blossom at room temperature by using petroleum ether with the weight of 12 times of the weight of the raw material of the peach blossom (leaching for 3 times and 3 days each time), filtering after the petroleum ether leaching is finished, and recovering filter residues. Then extracting with 70% ethanol 13 times the weight of the raw materials at room temperature (3 times, 3d each time), mixing ethanol extract after ethanol extraction, filtering, and concentrating to obtain 510 g ethanol total extract;
dispersing the ethanol extract in 50 mL water to form dispersion, sequentially extracting with petroleum ether (about 1 time volume of the dispersion), ethyl acetate (about 1 time volume of the dispersion) and n-butanol (about 1 time volume of the dispersion) for 3 times, respectively, recovering solvent to obtain petroleum ether fraction, ethyl acetate fraction and n-butanol fraction;
2) Dissolving the n-butanol part obtained in the step 1) by using 1:1 dichloromethane-methanol, stirring the solution by using 80-100 mesh silica gel, then performing gradient elution by using 200-300 mesh silica gel column chromatography according to a weight ratio of 1;
3) Dissolving the component 5 obtained in the step 2) by using 1:1 methylene chloride-methanol in volume ratio, mixing the solution with 80-100 mesh silica gel, then carrying out chromatographic separation on the mixture by using 200-300 mesh silica gel column according to the weight ratio of 1;
4) Mixing the Fr.5.1 obtained in the step 3) with silica gel, then loading the mixture on a column, performing silica gel column chromatographic separation, eluting with dichloromethane-methanol with the volume ratio of 20;
5) Mixing the Fr.5.1.1 obtained in the step 4) with silica gel, then loading the mixture on a column, separating by silica gel column chromatography, eluting with dichloromethane-methanol with the volume ratio of 10; dissolving Fr.5.1.1.1 with methanol, purifying by Sephadex LH-20 gel column chromatography, eluting with methanol, detecting by thin layer chromatography, mixing the same components, concentrating under reduced pressure, recovering solvent, and drying to obtain white powdered compound 1 (43 mg);
through identification, the compound 1 is chlorogenic acid n-butyl ester, and the structure is identified by using various spectroscopic techniques, which specifically comprise the following steps:
instrument materials: ultraviolet rays are measured by a UV-210A ultraviolet spectrum measuring instrument; 1 H-NMR、 13 the C-NMR spectrum was determined by a Bruker am-400 MHz NMR spectrometer, TMS was used as an internal standard, and the mass spectrum was determined by a VG.AUTO Spec-3000 type mass spectrometer.
The experimental results are as follows: compound 1, white powder (methanol), molecular formula C 20 H 26 O 9 ，ESI-MS m/z: 409 [M-H] - 。 1 H-NMR(400 MHz, DMSO-d 6 ) δ: 9.57(1H, s, -OH), 9.16(1H, s, -OH), 7.37(1H, d, J=15.9Hz, H-3′), 7.01(1H, d, J=1.9Hz, H-5′), 6.98(1H, dd, J=8.2Hz, 1.9Hz, H-9′), 6.78(1H, d, J=8.2Hz, H-8′), 6.12(1H, d, J=15.9Hz, H-2′), 5.03(1H, m, H-5), 3.97(2H, t, J=6.6, H-8), 3.92(1H, m, H-3), 3.58(1H, dd, J=5.7Hz, 3.0Hz, H-4), 2.11(2H, m, C 2 -αH, C 6 -αH), 1.95(1H, dd, J=13.6Hz, 3.5Hz, C 6 -βH), 1.76(1H, dd, J=12.6Hz, 9.4Hz, C 2 -βH), 1.49(2H, m, H-9), 1.25(2H, m, H-10), 0.82(3H, t, J=7.3Hz, H-11)。 13 C-NMR (100 MHz, DMSO-d 6 ) δ73.13 (C-1), 37.17 (C-2), 66.97 (C-3), 69.45 (C-4), 70.98 (C-5), 35.17 (C-6), 173.09 (C-7), 64.01 (C-8), 29.96 (C-9), 18.44 (C-10), 13.44 (C-11), 165.34 (C-1 '), 113.86 (C-2 '), 148.41 (C-3 '), 125.36 (C-4 '), 114.55 (C-5 '), 145.58 (C-6 '), 145.02 (C-7 '), 115.79 (C-8 '), 121.19 (C-9 '), see spectrogram 1 and 2 in detail.
Anticoagulant application test
The anticoagulant effect test is carried out on the active ingredient (namely the compound 1 chlorogenic acid n-butyl ester) of the anticoagulant peach blossom.
Instruments and reagents:
TGL-16gR high speed table refrigerated centrifuge (Shanghai' an Tingning scientific Instrument plant);
RAC-030 full automatic coagulation analyzer (denhan prescription medical devices ltd);
sodium chloride injection (chenxin pharmaceutical industry gmbh, 1603311336);
yunnan Baiyao (Yunnan Baiyao group GmbH, ZJA 1708);
breviscapine for injection (Kunming Longjin pharmaceutical industry Co., ltd., 20190813-1);
prothrombin Time (PT) assay kit (20191209M); activated Partial Thrombin Time (APTT) assay kit (20200319M); thrombin Time (TT) assay kit (20190821M); fibrinogen (FIB) content determination kits (20191120M) are all produced by Shenzhen Lei Du Life sciences GmbH.
Experimental animals: SD rats, SPF class, male, weight 180 to 200 g, supplied by the Experimental animals center of Henan province (SCXK 2017-0001).
Preparing a sample solution:
taking a compound 1 sample 3 mg, dissolving with 1000 mu L of solvent to prepare a solution with the concentration of 3 mg/mL;
preparing breviscapine 8 mg into solution with concentration of 13.33 mg/mL with 600 μ L solvent;
preparing Yunnan Baiyao 1 mg into solution with concentration of 40 mg/mL by using 25 μ L solvent;
solvents (also as blank solvents) were: absolute ethanol 1,2-propylene glycol sodium chloride injection =1: 1:3 (volume ratio).
Preparation of plasma: the rat is anesthetized by chloral hydrate, blood is taken from abdominal aorta, the abdominal aorta is placed in a disposable anticoagulation negative pressure vacuum tube, the mixture is gently inverted and mixed, the mixture is centrifuged at 3000 rpm for 15 min, and supernatant is taken for standby.
The specific test method comprises the following steps:
(1) Method for detecting APTT influence
Adding 25 μ L of each sample solution into different test cups, adding 50 μ L of plasma, placing into a blood coagulation instrument, automatically adding 25 μ L of APTT reagent, incubating at 37 deg.C, and adding 50 μ L of CaCl pre-warmed at 37 deg.C 2 And (5) recording the solidification time of the solution, namely the APTT value.
(2) Method for detecting influence on PT
And respectively adding 25 mu L of each sample solution into different test cups, adding 50 mu L of plasma, putting into a blood coagulation instrument, automatically adding 100 mu L of PT reagent, and recording the coagulation time to obtain the PT value.
(3) Method for detecting influence on TT
Respectively adding 25 mu L of each sample solution into different test cups, then adding 100 mu L of plasma, putting into a blood coagulation instrument, automatically adding 100 mu L of TT reagent, and recording the coagulation time, namely the TT value.
(4) Method for detecting impact on FIB
And respectively adding 25 mu L of each sample solution into different test cups, adding 50 mu L of plasma, placing into a blood coagulation instrument, automatically adding 100 mu L of FIB reagent, and recording the content of the fibrinogen.
And (3) test results:
the results are expressed as arithmetic mean and standard deviation, and the significance difference of the numerical statistics is compared by SPSS19.0 software One-Way ANOVA (One-Way ANOVA), and the measurement results are shown in Table 1.
TABLE 1 Effect of the Compounds on clotting time and fibrinogen content (x. + -. S) in rats
Note: data represent mean ± SD, N =4
Comparison with blank: ### p<0.001< ## p<0.01< # p<0.05；
compared with Yunnan Baiyao: △△△ p<0.001< △△ p <0.01< △ p <0.05；
comparing with breviscapine: *** p<0.001< ** p<0.01< * p<0.05。
as can be seen from Table 1, compared with the blank group, the anticoagulant peach blossom active ingredient compound 1 can remarkably prolong APTT (A)p<0.01 It is weaker than Breviscapine: (B)p<0.001 ); can prolong PT (p<0.05 It is weaker than Breviscapine: (B)p<0.01 ); can obviously reduce FIB content (p<0.001 Herb of common Breviscapine (Breviscapine) ((B))p<0.05). Therefore, the anticoagulant peach blossom effective component compound 1 can prolong APTT and PT time, reduce FIB content and prompt that the compound 1 has a certain anticoagulant effect and can be used as an anticoagulant reagent.
Claims (1)
1. Application of n-butyl chlorogenic acid in preparing anticoagulant medicine is provided.
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| 张武岗 等.白花檵木止血化学成分分析.2017,第23卷(第5期),第47-52页. * |
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