CN111362896B - Safflower yellow and its application in preparing medicine for treating cardiovascular and cerebrovascular diseases - Google Patents
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Abstract
The invention discloses safflower yellow and application thereof in preparing a medicament for treating cardiovascular and cerebrovascular diseases, wherein the novel safflower yellow is 2, 4-di-beta-D-glucose-3, 4, 5-trihydroxy-6- [ (2E) -3- (3, 4-dihydroxyphenyl) -1-ketone-2-propylene-1-yl ] -2, 5-cyclohexadiene-1-ketone (I-2). The novel safflower yellow of the invention has obvious pharmacological actions of free radical removal and platelet aggregation resistance, and the pharmacological action is superior to or equivalent to that of a clinical medicament, namely hydroxy safflower yellow A, and has important significance for developing anti-cardiovascular disease medicaments with stronger treatment effect, lower toxicity and wider adaptation diseases.
Description
Technical Field
The invention belongs to the field of pharmacy, and particularly relates to a novel safflower yellow and application thereof in preparing a medicament for treating cardiovascular and cerebrovascular diseases.
Background
The safflower yellow is one of main effective components of Carthami flos of Compositae, and is composed of chalcone compounds. The water-soluble hydroxyl safflower yellow A is the component with the highest content in the safflower yellow, has been successfully developed into clinical medicine-safflower yellow for injection, has the efficacies of promoting blood circulation by removing blood stasis, and dredging collaterals and relieving pain, and is used for treating I, II and III grade stable exertional angina caused by heart blood stasis.
The safflower yellow has the functions of inhibiting platelet aggregation and thrombosis, improving myocardial blood supply, resisting oxidation, lowering blood pressure, resisting inflammation, relieving pain and the like, and plays an important role in treating cardiovascular diseases and improving diseases. Antioxidation and antiplatelet aggregation are two important pharmacological functions of safflower yellow. On one hand, the carthamin yellow can remove a large amount of free radicals generated in the process of ischemia reperfusion injury and inflammatory reaction of coronary heart disease, and inhibit lipid peroxidation, thereby protecting cardiac muscle and nerve from being damaged. On the other hand, safflower yellow is an antagonist of Platelet Activating Factor (PAF) and is capable of inhibiting PAF-induced platelet aggregation and inflammatory reaction, and safflower yellow is also capable of inhibiting adenosine diphosphate sodium salt (ADP) -induced platelet aggregation, significantly prolonging coagulation time and prothrombin time, reducing fibrinogen content, and thereby inhibiting thrombosis.
At present, researches on safflower yellow in prevention and treatment of cardiovascular diseases mainly focus on hydroxysafflower yellow A, and other types of safflower yellow are only reported. However, the complexity of cardiovascular diseases and the disadvantages of the existing drugs also pose new challenges for the prevention and treatment of cardiovascular diseases, and therefore, the development of new therapeutic drugs is urgently needed.
Disclosure of Invention
The invention provides a novel safflower yellow and application thereof in preparing medicaments for treating cardiovascular and cerebrovascular diseases, and researches the pharmacological action of the novel safflower yellow in the aspects of oxidation resistance and platelet aggregation resistance.
A safflower yellow having one or more of the following structures:
wherein R is 1 Is beta-D-glucosyl or alpha-D-glucosyl; r 2 、R 3 Each independently is hydroxyl, hydrogen or beta-D-glucosyl or alpha-D-glucosyl; r 4 Hydrogen and hydroxyl; r 5 Hydrogen and hydroxyl; r 6 Is a hydroxyl group.
A safflower yellow having one or more of the following structures:
the method comprises the following steps:
a novel carthamus tinctorius yellow colour is one or more of the following compounds:
4- β -D-glucose-2, 4, 5-tetrahydroxy-6- [ (2E) -3- (4-hydroxyphenyl) -1-one-2-propen-1-yl ] -5-cyclohexene-1, 3-dione (I-1);
2, 4-di- β -D-glucose-3, 4, 5-trihydroxy-6- [ (2E) -3- (3, 4-dihydroxyphenyl) -1-one-2-propen-1-yl ] -2, 5-cyclohexadiene-1-one (I-2);
4-beta-D-glucose-4, 5-dihydroxy-6- [ (2E) -3- (4-hydroxyphenyl) -1-one-2-propen-1-yl ] -5-cyclohexene-1, 3-dione (I-3).
The structural formula is as follows:
the application of the novel safflower yellow in preparing the medicine for treating cardiovascular and cerebrovascular diseases is characterized in that the novel safflower yellow is one or more of the following compounds:
4- β -D-glucose-2, 4, 5-tetrahydroxy-6- [ (2E) -3- (4-hydroxyphenyl) -1-one-2-propen-1-yl ] -5-cyclohexene-1, 3-dione (I-1);
2, 4-di- β -D-glucose-3, 4, 5-trihydroxy-6- [ (2E) -3- (3, 4-dihydroxyphenyl) -1-one-2-propen-1-yl ] -2, 5-cyclohexadiene-1-one (I-2);
4-beta-D-glucose-4, 5-dihydroxy-6- [ (2E) -3- (4-hydroxyphenyl) -1-one-2-propen-1-yl ] -5-cyclohexene-1, 3-dione (I-3).
The structural formula is as follows:
preferably, the novel safflower yellow is one or more of 2, 4-di-beta-D-glucose-3, 4, 5-trihydroxy-6- [ (2E) -3- (3, 4-dihydroxyphenyl) -1-one-2-propen-1-yl ] -2, 5-cyclohexadiene-1-one (I-2), 4-beta-D-glucose-4, 5-dihydroxy-6- [ (2E) -3- (4-hydroxyphenyl) -1-one-2-propen-1-yl ] -5-cyclohexene-1, 3-dione (I-3).
Preferably, the cardiovascular disease treatment diseases of the anti-cardiovascular disease drug are cardiovascular diseases caused by free radical oxidation and platelet aggregation.
Preferably, the disease for which the anti-cardiovascular disease drug is used for treatment includes one or more of coronary heart disease, thrombosis, angina, pulmonary heart disease, atherosclerosis, hypertension, hyperlipidemia, and hyperglycemia.
The compound can be prepared by firstly concentrating and enriching by a water extraction method and then carrying out macroporous resin column chromatography, gel column chromatography, ODS reverse column chromatography and the like.
The free radical DPPH scavenging experiment and the free radical ABTS scavenging experiment show that the novel safflower yellow can effectively scavenge free radicals; the ADP-induced platelet aggregation inhibition experiment and the PAF-induced platelet aggregation inhibition experiment show that the novel safflower yellow can effectively inhibit platelet aggregation.
The invention has the beneficial effects that the safflower yellow is a natural active compound with a novel structure reported for the first time, has obvious pharmacological actions of free radical elimination and platelet aggregation resistance, is superior to or equivalent to the hydroxyl safflower yellow A used as a clinical medicament, and has important significance for developing cardiovascular disease resistant medicaments with stronger treatment effect, lower toxicity and wider adaptation diseases.
Detailed Description
The invention is further illustrated by the following examples, it being understood that these examples are intended in an illustrative rather than in a limiting sense.
Example 1: preparation method and structural representation of novel safflower yellow
The preparation of the novel safflower yellow refers to the patent documents (CN 106496172A, CN 102657691A) and the documents (Jinming, gooshu, lijinrong, etc. the preparation of the safflower yellow and the hydroxysafflower yellow A. Chinese herbal medicine, 2004,35 (1): 25-28) by macroporous resin column chromatography, firstly, crude safflower yellow is extracted from the Chinese medicinal material safflower by a water extraction method, and then the novel safflower yellow is separated and purified by macroporous resin column chromatography, gel column chromatography, ODS reverse column chromatography and other means.
The structural representation data of the prepared novel safflower yellow are as follows:
4-beta-D-glucose-2, 4, 5-tetrahydroxy-6- [ (2E) -3- (4-hydroxyphenyl) -1-one-2-propen-1-yl ] -5-cyclohexene-1, 3-dione (I-1)
FTIR(KBr)ν max cm -1 :3384,2931,1750,1683,1597,1513,1423,1260,1079,1008,942,832；
1 H NMR(500MHz,DMSO-d6)δ9.86(s,1H),7.90(d,J＝16.0Hz,1H),7.44(d,J＝8.5Hz,2H),7.38(d,J＝16.0Hz,1H),6.81(d,J＝9.0Hz,2H),5.99(s,1H),5.54(s,2H),5.24(s,1H),4.78(s,1H),3.73(m,2H),3.49(d,J＝10.5Hz,1H),3.38(m,2H),3.20(m,1H),2.95(t,J＝9.0Hz,1H)；
13 C NMR(500MHz,DMSO-d6)δ195.82,192.27,183.97,171.43,159.40,138.92,129.98,127.24,124.84,116.25,110.89,81.36,81.02,80.91,79.60,75.73,75.23,70.46,61.54；HRMS(ESI):m/z calcd for C 21 H 22 O 13 [M+H-H 2 O] + :465.1028,found:465.1031.
2, 4-Di-beta-D-glucose-3, 4, 5-Trihydroxyl-6- [ (2E) -3- (3, 4-dihydroxyphenyl) -1-one-2-propen-1-yl ] -2, 5-cyclohexadiene-1-one (I-2)
FTIR(KBr)ν max cm -1 :3383,2929,1598,1442,1407,1283,1078,1007,923,889,811；
1 H NMR(500MHz,DMSO-d6)δ7.37(d,J＝16.0Hz,1H),7.22(d,J＝16.0Hz,1H),6.97(d,J＝1.5Hz,1H),6.84(dd,J＝8.0,1.5Hz,1H),6.70(d,J＝8.0Hz,1H),4.20(d,J＝9.5Hz,1H),4.12(t,J＝9.5Hz,1H),3.61(m,3H),3.38(m,1H),3.31(m,2H),3.10(m,2H),3.06(m,1H),3.03(m,1H),2.95(m,1H),2.89(m,1H)；
13 C NMR(500MHz,DMSO-d6)δ195.34,189.29,182.91,179.35,147.67,145.67,136.57,127.32,122.64,120.48,115.55,114.04,105.75,99.28,85.54,85.12,80.57,80.18,79.15,78.13,73.86,70.88,69.85,68.69,61.49 61.09；HRMS(ESI):m/z calcd for C 27 H 32 O 17 [M+H] + :629.1712,found:629.1712.
4-beta-D-glucose-4, 5-dihydroxy-6- [ (2E) -3- (4-hydroxyphenyl) -1-one-2-propen-1-yl ] -5-cyclohexene-1, 3-dione (I-3)
FTIR(KBr)ν max cm -1 :3421,2926,1670,1627,1577,1514,1422,1262,1088,1016,990,826；
1 H NMR(500MHz,DMSO-d6)δ9.83(s,1H),7.98(d,J＝15.5Hz,1H),7.41(d,J＝8.5Hz,2H),7.33(d,J＝16.0Hz,1H),6.79(d,J＝8.5Hz,2H),5.91(s,1H),5.46(d,J＝4.5Hz,1H),5.04(d,J＝5.0Hz,1H),4.97(d,J＝5.5Hz,1H),4.53(t,J＝5.5Hz,1H),4.34(d,J＝9.5Hz,1H),3.65(m,1H),3.39(m,1H),3.29(m,1H),3.22(m,1H),3.12(m,1H),3.03(m,1H),2.68(d,J＝17.0Hz,1H),2.09(d,J＝17.0Hz,1H)；
13 C NMR(500MHz,DMSO-d6)δ207.58,198.50,196.93,183.21,158.58,137.64,129.22,126.90,124.55,115.63,111.33,84.30,81.62,78.02,77.62,71.20,70.06,61.15,46.16；HRMS(ESI):m/z calcd for C 21 H 22 O 11 [M+H] + :451.1235,found:451.1233.
Example 2: evaluation of the ability of novel safflor yellow to scavenge free radicals DPPH and ABTS the present invention evaluates the ability of test compounds to protect the cardiovascular system from free radical damage and oxidation by determining the ability of novel safflor yellow to scavenge free radicals DPPH and ABTS. The invention takes hydroxysafflor yellow A as a positive control, and the experimental result takes the clearance rate of free radicals as a parameter.
Evaluation method of radical DPPH scavenging ability: dissolving and diluting a sample to 100 mu g/ml by using a methanol solution (solvent is water) with the volume fraction of 70% to obtain a sample solution, adding 100 mu L of the sample solution into a 96-well enzyme label plate, adding 100 mu L of DPPH solution (0.15 mmol/L, solvent ethanol), fully mixing, then carrying out a dark reaction at room temperature for 30min, measuring the absorbance (As) at 517nm by using an enzyme label instrument, using the methanol solution with the volume fraction of 70% to replace the reaction of the sample As a blank (Ac), using the methanol solution with the volume fraction of 70% to replace the reaction of the DPPH solution As a sample blank (Ab), using hydroxysafflor yellow A As a positive control, and calculating the free radical scavenging rate according to the formula.
The evaluation method of the scavenging capacity of the free radical ABTS comprises the following steps: dissolving and diluting a sample to 100 mu g/ml by using a methanol solution with a volume fraction of 70% to obtain a sample solution, adding 25 mu L of the sample solution into a 96-hole enzyme label plate, adding 200 mu L of an ABTS solution (containing 7mmol/L of ABTS and 2.45mmol/L of potassium persulfate, and taking water As a solvent), fully mixing, then carrying out a dark reaction at room temperature for 6min, measuring the absorbance (As) at 734nm by using an enzyme label instrument, taking the reaction of replacing the sample by the methanol solution with the volume fraction of 70% As a blank (Ac), taking the reaction of replacing the ABTS solution by the methanol solution with the volume fraction of 70% As a blank (Ab) of the sample, taking hydroxysafflor yellow A As a positive control, and calculating the free radical clearance according to the formula.
Radical clearance = [ Ac- (As-Ab) ]/Ac × 100%
The radical scavenging ability of the test compound was classified into 4 classes, i.e. "+ + + +", according to the magnitude of the radical scavenging rate of the test compound: free radical scavenging ability (%) 75-100; mid-clear capability "+": free radical scavenging capacity (%) 50-75; low cleaning power "+": free radical scavenging capacity (%) 25-50; no scavenging ability "- -": free radical scavenging ability (%) of 25 or less. The results are shown in Table 1.
TABLE 1 free radical scavenging ability of novel safflor yellow
Experimental results show that the novel safflower yellow has certain free radical scavenging capacity, wherein the free radical scavenging capacity of the compound I-2 is superior to that of hydroxy safflower yellow A.
Example 3: evaluation of anti-platelet aggregation ability of novel safflor yellow
The invention evaluates the capabilities of the tested compound in prolonging the blood coagulation time, inhibiting the thrombosis and improving the myocardial blood supply by measuring the inhibition capability of the novel safflor yellow to platelet aggregation induced by ADP and PAF. The invention takes hydroxysafflor yellow A as a positive control, and the experimental result takes the platelet aggregation inhibition rate as a parameter.
Evaluation of inhibitory ability of ADP-induced platelet aggregation: SD rats were bred for one week in an adaptive manner, and randomly divided into 5 groups of 10 rats each, namely a normal control group (physiological saline), hydroxysafflor yellow A (60 mg/kg) and a drug administration group (60 mg/kg). The animals were anesthetized with ether after 7d intraperitoneal injections, overnight fasting on day 6, 2h after 7 days administration, and blood was taken from the abdominal aorta, 3.8% sodium citrate solution, at a volume of 1:9 anticoagulating, centrifuging at 1000rpm for 10min, collecting supernatant to obtain Platelet Rich Plasma (PRP), centrifuging the rest at 3000rpm for 10min, collecting supernatant to obtain Platelet Poor Plasma (PPP), and adjusting the number of platelets in PRP to (3-4) × 10 by using PPP 9 And L. Platelet aggregation in rats was induced with 20. Mu.L of ADP, and the maximum platelet aggregation rates (PAG) in the normal control group and the administered group were measured within 5min max %). The inhibition rate (IR%) of platelet aggregation by the administration group was calculated. IR% = (normal control PAG) max Administration group PAG max ) Normal control PAG max ×100％。
Evaluation of inhibitory ability of PAF-induced platelet aggregation: under the waking state, the white big-ear rabbits are locally anesthetized by lidocaine, the left common carotid artery is separated, the length of the common carotid artery is about 2-3 cm, and the blood is taken from the common carotid artery according to the volume ratio of 9: l and 3.8% sodium citrate, placing in plastic tube, centrifuging at 1000rpm for 10min to obtain supernatant as Platelet Rich Plasma (PRP); the remaining part was centrifuged at 3000rpm for 10min, and the supernatant fraction was obtained as Platelet Poor Plasma (PPP). Counting platelets with a fully automatic cytometer and adjusting PRP to a final platelet concentration of 3X 10 with PPP 5 and/mL. According to the Born method, the method of the present invention,placing PPP added with 500 μ L detection sample into PPP hole, adding 500 μ L PRP added with detection sample into PRP hole, incubating for 5min, adding 20 μ L absolute ethanol (final concentration of 9.26 ‰) into control group, adding safflower yellow 20 μ L (final concentration of 0.448 g/L) into test group, adding hydroxysafflower yellow A20 μ L (final concentration of 0.448 g/L) into positive control group. After 5min incubation, 20. Mu.L of PAF (final concentration of 725.63. Mu. Mol/mL) was added to each cuvette, and the rate of platelet aggregation was determined by the aggregation curve traced by a 570-VS platelet aggregometer, and the inhibition rate of the dosing group on platelet aggregation (IR%) was calculated. IR% = (aggregation rate of anhydrous alcohol group-aggregation rate of administered group)/aggregation rate of anhydrous alcohol group × 100%.
The ability of the test compound to inhibit platelet aggregation was classified into 4 classes, i.e., high inhibitory ability "+++": platelet aggregation inhibition (%) of 75-100; medium inhibitory capacity "+": platelet aggregation inhibition (%) of 50-75; low suppression capacity "+": platelet aggregation inhibition (%) of 25-50; no inhibitory activity "- -": the platelet aggregation inhibition rate (%) is 25 or less. The results are shown in Table 2.
TABLE 2 anti-platelet aggregation ability of novel safflor yellow
Experimental results show that the novel safflower yellow provided by the invention has certain platelet aggregation inhibiting capability, wherein the platelet aggregation inhibiting capability of the compound I-2 is superior to that of the hydroxysafflor yellow A, and the platelet aggregation inhibiting capability of the compound I-3 is equivalent to that of the hydroxysafflor yellow A.
Claims (6)
1. The safflower yellow is characterized by comprising the following components in percentage by weight:
2, 4-di-beta-D-glucose-3, 4, 5-trihydroxy-6- [ (2, 4-D-glucose)E) -3- (3, 4-dihydroxyphenyl) -1-keto-2-propen-1-yl]-2, 5-cyclohexadien-1-one.
2. The safflower yellow of claim 1, having the structure:
3. the safflower yellow of claim 1, having the structure:
4. use of safflower yellow in the preparation of a medicament for treating cardiovascular and cerebrovascular diseases, wherein the safflower yellow is the safflower yellow according to any one of claims 1 to 3.
5. The use of safflower yellow according to claim 4 for the manufacture of a medicament for the treatment of cardiovascular and cerebrovascular diseases, wherein said cardiovascular disease is cardiovascular disease caused by free radical oxidation and platelet aggregation.
6. The use of safflower yellow according to claim 4 in the manufacture of a medicament for the treatment of cardiovascular and cerebrovascular diseases wherein said cardiovascular disease is one or more of coronary heart disease, thrombotic disorders, angina pectoris, pulmonary heart disease, atherosclerosis, hypertension, hyperlipidemia.
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| CN1422616A (en) * | 2001-12-06 | 2003-06-11 | 长春三真实业有限公司 | Use of hydroxy saflor yellow pigment A in preparing medicine for treating and preventing cardiovascular and cerebrovascular disease |
| CN102657691A (en) * | 2012-06-02 | 2012-09-12 | 悦康药业集团安徽天然制药有限公司 | Extraction process of carthamin yellow |
| CN106496172A (en) * | 2016-10-21 | 2017-03-15 | 乌鲁木齐上善元生物科技有限公司 | A kind of method for extracting Carthamus yellow from Flos Carthami |
| WO2017219510A1 (en) * | 2016-06-24 | 2017-12-28 | 南京中医药大学 | Quinoid chalcone c-glycoside dimer compound having anti-tumor activity and anti-inflammatory activity and method for preparing same |
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| CN1264708A (en) * | 1998-11-24 | 2000-08-30 | 北京市心肺血管疾病研究所 | Total safflower yellow and its preparing process and application |
| CN101195647B (en) * | 2006-12-06 | 2010-08-18 | 山西华辉凯德制药有限公司 | Hydroxyl carthamus tinctorius yellow colour A, preparation method and application thereof |
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2018
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- 2018-12-25 CN CN202211320074.4A patent/CN115677638B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1422616A (en) * | 2001-12-06 | 2003-06-11 | 长春三真实业有限公司 | Use of hydroxy saflor yellow pigment A in preparing medicine for treating and preventing cardiovascular and cerebrovascular disease |
| CN102657691A (en) * | 2012-06-02 | 2012-09-12 | 悦康药业集团安徽天然制药有限公司 | Extraction process of carthamin yellow |
| WO2017219510A1 (en) * | 2016-06-24 | 2017-12-28 | 南京中医药大学 | Quinoid chalcone c-glycoside dimer compound having anti-tumor activity and anti-inflammatory activity and method for preparing same |
| CN106496172A (en) * | 2016-10-21 | 2017-03-15 | 乌鲁木齐上善元生物科技有限公司 | A kind of method for extracting Carthamus yellow from Flos Carthami |
Non-Patent Citations (1)
| Title |
|---|
| 红花黄色素化学成分及对心脑血管作用研究进展;武永刚 等;《齐鲁药事》;20111231;第30卷(第8期);第481-484页 * |
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| Publication number | Publication date |
|---|---|
| CN115677638A (en) | 2023-02-03 |
| CN115677638B (en) | 2023-11-14 |
| CN111362896A (en) | 2020-07-03 |
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