CN103142690A - Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as antithrombotic agent - Google Patents
Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as antithrombotic agent Download PDFInfo
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Abstract
The invention relates to rabdosia rubescens stem aqueous extract and its preparation method and finger-prints, wherein the rabdosia rubescens stem aqueous extract is extracted from rabdosia rubescens stems by distilled water at a temperature of 80DEG C and the finger-prints comprise a HPLC-(-)ESI-Q-TOF-MS/MS finger-print and a HPLC-(+)ESI-Q-TOF-MS/MS finger-print. The invention also relates to the antithrombotic activity of the rabdosia rubescens stem aqueous extract in a rat thrombosis model and a use of the rabdosia rubescens stem aqueous extract as an antithrombotic agent.
Description
Invention field
The present invention relates to the Rabdosia rubescens stem with 80 ℃ of distilled water extract the preparation water extracts, relate to this water extract HPLC-(-) ESI-Q-TOF-MS/MS finger printing, relate to HPLC-(+) the ESI-Q-TOF-MS/MS finger printing of this water extract, further relate to this water extract on the rat suppository formation model antithrombotic acitivity and as the application of antithrombotic agents.The invention belongs to biomedicine field.
Background technology
Thrombotic disease is a kind of common cardiovascular and cerebrovascular disease, often shows as myocardial infarction, Ischemic Cerebral Infarction, venous thromboembolism etc.Just there is 1～3 people that multi-form thrombotic disease occurs among annual each thousand people.Thrombotic disease seriously affects human health.Antithrombotic is the important topic of human society face prison.Supervise at present bed thromboembolism preventing medicine antithrombotic commonly used.Because these medicines all exist such or such shortcoming.For example can cause bleeding, thrombosis bounce-back after liver injury, damage gastric mucosa and drug withdrawal.Seek safety, effectively, without hemorrhage reaction, the thromboembolism preventing medicine of liver injury and gastric mucosa is not the important directions of new drug research.
Rabdosia rubescens (DLC) is the crack rice herb of fork Rabdosia rubescens (Hemsl.) Hara of Labiatae Rabdosia plant.Rabdosia rubescens is herbaceos perennial, is distributed widely in the Yangtze river basin, China the Yellow River, main product in the Jiyuan, Henan Taihang Mountain, Wangwu Shan Mountain district one band.Because having heat-clearing and toxic substances removing, pharynx-clearing throat-benefiting and a reducing swelling and alleviating pain function, among the peoplely the Rabdosia rubescens leaf is used as that Folium Camelliae sinensis is to boil water to be drunk throughout the year.
In in the past more than 30 year, the chemical composition of Rabdosia rubescens and pharmacological research mainly concentrate on the fatty contents of leaf, and representative composition is rubescensine A and rubescensine B.Be seen in document without any the research relevant to the chemical composition of Rabdosia rubescens stem and pharmacological action so far.Compare with leaf, although Rabdosia rubescens stem shared ratio in herb is high a lot, the Rabdosia rubescens stem is not effectively applied to the mankind's healthy cause.
By long-term antithrombotic reagent research accumulation, the inventor locks phenolic acid and diterpene is the structure type with antithrombotic acitivity.Predict by the Analyzing Source of Students inventor and contain abundant phenolic acid and diterpene in the Rabdosia rubescens stem.According to these understanding, the inventor proposes the present invention, and use HPLC-(-) ESI-Q-TOF-MS/MS finger printing and HPLC-(+) ESI-Q-TOF-MS/MS finger printing disclose the chemical composition of Rabdosia rubescens stem water extract, the anti thrombotic action that use rat suppository formation model discloses Rabdosia rubescens stem water extract.
Summary of the invention
First technical problem to be solved by this invention is to provide a kind of method for preparing Rabdosia rubescens stem water extract.
Second technical problem to be solved by this invention is to set up HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS analytical method, obtains the finger printing of Rabdosia rubescens stem water extract in order to control the quality of Rabdosia rubescens stem water extract.
The 3rd technical problem to be solved by this invention is to estimate the anti thrombotic action of Rabdosia rubescens stem water extract with the rat suppository formation model, for the prevention thrombotic disease provides Rabdosia rubescens stem water extract as the high material that has no side effect of antithrombotic acitivity.
The present invention relates to the preparation technology of Rabdosia rubescens stem water extract, this technique comprise the Rabdosia rubescens stem with hot water extraction, water extract filter, filtrate decompression be concentrated into dried, the dry powder that obtains with HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS analyze finger printing, the dry powder that obtains with the anti thrombotic action of rat suppository formation model evaluation Rabdosia rubescens stem water extract.
In order further to set forth the present invention, the below provides a series of embodiment.These embodiment are illustrative fully, and they only are used for the present invention is specifically described, and not should be understood to limitation of the present invention.
Description of drawings
The ion flow finger printing that Fig. 1 a Rabdosia rubescens stem water extract detects at (-) ESI-Q-OF-MS
The ion flow finger printing that Fig. 1 b Rabdosia rubescens stem water extract detects at (+) ESI-Q-TOF-MS
The specific embodiment
The preparation of embodiment 1 Rabdosia rubescens stem water extract
The dried Rabdosia rubescens stem of 40g tap water is cleaned, airing, to be cut into the long stem section of about 1cm, to add the 1000-1800mL temperature be the hot distilled water diafiltration of 70-90 ℃, preferably adds the 1200mL temperature and be the hot distilled water diafiltration of 80 ℃.The speed that percolate flows out is 10-30mL/ minute, preferred 20mL/ minute.Effluent is preferable over 50 ℃ of concentrating under reduced pressure in 40-60 ℃ of concentrating under reduced pressure, obtains 3g Rabdosia rubescens stem water extract, is faint yellow solid.Pulverize is for the research of back.
HPLC-(-) ESI-Q-TOF-MS/MS of embodiment 2 Rabdosia rubescens stem water extracts and HPLC-(+) ESI-Q-TOF-MS/MS finger printing
HPLC：Waters?2795Separations?Module；
Detector：Waters?2489Dual?absorbance?detector；
Kromasil C
18(Dikma) reversed-phase column (5_ μ m, 250_mm_ * _ 4.6_mm);
Guard column (5_ μ m, 10_mm_ * _ 4.6_mm);
Mobile phase: acetonitrile/water (containing 0.5% and 0.05% glacial acetic acid);
Flow rate of mobile phase: 0.3ml/min;
Sample size: 50 μ l;
Type of elution: gradient elution (concrete gradient sees Table 1).
Table 1 Rabdosia rubescens stem water extract HPLC-analyzes the eluent gradient table
a
aThe A=acetonitrile, (contain 0.05% glacial acetic acid, v/v), C=water (contains 0.5% glacial acetic acid, v/v) to B=water
The ion flow finger printing of Rabdosia rubescens stem water extract under HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS detection: Fig. 1 a and Fig. 1 b once analyze 22 peaks;
(-) ESI-Q-TOF-MS ion flow finger printing of embodiment 3 Rabdosia rubescens stem water extracts
(-) ESI-Q-TOF-MS: adopt one to optimize good small molecule analysis method, design parameter is a) Source Type:ESI; B) Ion Polarity:Negative; C) Scan begin:50m/z; D) Scan begin:1500m/z; E) Set Capillary:3500V; F) Set Nebulizer:0.8Bar; G) Set Dry Heater:200 ℃; H) Set Dry Gas:8.0ml/min; I) Funnel 1RF:300Vpp; J) Funnel2RF:300Vpp; K) ISCID Energy:0eV; L) Hexapole RF:200Vpp; M) IonEnergy:5eV; N) Low Mass:200m/z; O) Collision Energy:14eV; P) Collision RF:140Vpp; Q) Transfer Time:110.8 μ S; R) Pre Puls Storage:8.7 μ S; S) Source:1400v, 2nA; T) adopt sodium formate that mass spectrograph is proofreaied and correct before each the analysis.
Use high-efficient liquid phase chromatogram condition and the good mass spectrum condition of system optimization of having groped, adopting negative ion mode is that (-) ESI carries out (-) ESI-Q-TOF-MS analysis to Rabdosia rubescens stem water extract.Its one-level mass spectrum ion flow is seen Fig. 1 a.Can find out single injected sampling from Fig. 1 a, analysis time, 350min, detected 22 peaks altogether from the one-level mass spectrum.
(+) ESI-Q-TOF-MS ion flow finger printing of embodiment 4 Rabdosia rubescens stem water extracts
(+) ESI-Q-TOF-MS: adopt one to optimize good small molecule analysis method, design parameter is a) SourceType:ESI; B) Ion Polarity:Negative; C) Scan begin:50m/z; D) Scan begin:1500m/z; E) Set Capillary:3500V; F) Set Nebulizer:0.8Bar; G) Set Dry Heater:200 ℃; H) Set Dry Gas:8.0ml/min; I) Funnel 1RF:300Vpp; J) Funnel2RF:300Vpp; K) ISCID Energy:0eV; L) Hexapole RF:200Vpp; M) Ion Energy:5eV; N) Low Mass:200m/z; O) Collision Energy:14eV; P) Collision RF:140Vpp; Q) Transfer Time:110.8 μ S; R) Pre Puls Storage:8.7 μ S; S) Source:1400v, 2nA; T) adopt sodium formate that mass spectrograph is proofreaied and correct before each the analysis.
Use high-efficient liquid phase chromatogram condition and the good mass spectrum condition of system optimization of having groped, adopting positive ion mode is that (+) ESI carries out (+) ESI-Q-TOF-MS analysis to Rabdosia rubescens stem water extract.Its one-level mass spectrum ion flow is seen Fig. 1 b.Can find out single injected sampling from Fig. 1 b, analysis time, 350min, detected 22 peaks equally from the one-level mass spectrum.
Phenolic acid and diterpene in embodiment 5 HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS spectrum definition Rabdosia rubescens stem water extract
With the second order ms data of Rabdosia rubescens stem water extract and the second order ms data contrast of standard substance, perhaps with the second order ms data contrast of the compound of bibliographical information, perhaps utilize compound cracking rule to derive, the present invention confirmed corresponding to, the peak 1 of Fig. 1 a, 10,11,14,15 and 17 totally 6 phenolic acid, the peak 16,19,20 and 21 of Fig. 1 b is totally 4 diterpene.
(-) ESI-Q-TOF-MS at peak 1 provides [M-H]
-/ 197 and the daughter ion that provides of [2M-H]-/395. second order ms [M-H-H is arranged
2O]
-/ 179 and [M-H-H
2O-CO
2]
-/ 135.These second order mses with the danshensu standard substance are consistent, and peak 1 is danshensu.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 17 provides [M-H]
-/ 717,, [2M-H]
-/ 1435, [M+H]
+/ 719, [M+Na]
+/ 741, [2M+H]
+/ 1437and[2M+Na]
+/ 1459. second order mses provide m/z 197, [M-H-198]
-/ 519, [M-H-180]
-/ 537, [M-H-180-18-44]
-/ 475, [M-H-198-180]
-/ 339 and [M-H-198-198]
-/ 321 these second order mses with salvianolic acid B are consistent, and peak 17 is salvianolic acid Bs.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 10 provides [M-H]
-/ 537, [2M-H]
-/ 1075, [M+H]
+/ 539 and [M+Na]
+/ 561.Second order ms provides m/z/197, [M-H-44-198]
-/ 295, [M-H-180]
-/ 357, [M-H-44]
-/ 493, [M-H-180-44]
-/ 313 and [M-H-180-44 * 2]
-/ 269.These daughter ions 17 are also observed at the peak.Because the molecular ion at peak 10 and peak 17 differs the mass number of a danshensu residue just, so 5-(2-carboxyvinyl)-2 is appointed as at peak 10,3-dihydro-7-hydroxy-2-(3,4-dihydroxyphenyl) benzofuran-3-carboxylic acid1-carboxy-2-(3,4-dihydroxyphenyl)-ethyl ester.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 11 provides [M-H]
-/ 537, [2M-H]
-/ 1075, [M+H]
+/ 539 and [M+Na]
+/ 561.Second order ms provides m/z/197, [M-H-44-198]
-/ 295, [M-H-180]
-/ 357, [M-H-44]
-/ 493, [M-H-180-44]
-/ 313 and [M-H-180-44 * 2]
-/ 269.These are consistent with peak 10, and just the retention time of HPLC is different, so the isomer at peak 10 is appointed as at peak 11.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 14 provides [M-H]
-/ 715, [M+H]
+/ 717 and [M+Na]
+/ 739. because the daughter ion m/z/537 that the second order ms at peak 14 provides, m/z/519, m/z/493, m/z/339, m/z/295, m/z/267 lacks 2 with m/z/197 with the consistent just molecular weight of daughter ion that the second order ms of salvianolic acid B provides, so the product that salvianolic acid B takes off a part hydrogen is appointed as at peak 14.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 15 provides [M-H]
-/ 715, [M+H]
+/ 717 and [M+Na]
+/ 739. because the daughter ion m/z/537 that the second order ms at peak 15 provides, m/z/519, and m/z/493, m/z/339, m/z/295, m/z/267 is consistent with peak 14 with m/z/197, and the retention time of HPLC difference just is so the isomer at peak 14 is appointed as at peak 15.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 16 provides [M-H]
-/ 363 and [M+H]
+/ 365.Second order ms provides daughter ion [M-H-H
2O]
-/ 345, [M-H-2H
2O]
-/ 327, [M-H-3H2O]
-/ 309, [M-H-H
2O-CH
2O]
-/ 315, [M-H-2H
2O-CO
2]
-/ 283, [M-H-2H
2O-CO]
-/ 299 and [M-H-CH
2O-2H
2O]
-/ 297.These ions are consistent with the ion of Amethystonoic acid.Amethystonoic acid is appointed as at peak 16 like this.
(-) ESI-Q-TOF-MS at peak 19 and (+) ESI-Q-TOF-MS provide [M-H]
-/ 363, [2M-H]
-/ 727, [M+H]
+/ 365, [M+Na]
+/ 387, [2M+H]
+/ 729 and [2M+Na]
+/ 751.Second order ms provides daughter ion [M-H-H
2O]
-/ 345, [M-H-CH
2O]
-/ 333, [M-H-2H
2O]
-/ 327, [M-H-CH
2O-H
2O]
-/ 315, [M-H-3H
2O]
-/ 309, [M-H-4H
2O]
-/ 291 and [M-H-CH
2O-2H
2O]
-/ 297.These ions are consistent with the ion of oridonin.Oridonin is appointed as at peak 16 like this.
(-) ESI-Q-TOF-MS at peak 20 and (+) ESI-Q-TOF-MS provide [M-H]
-/ 407, [M+H]
+/ 409, [M+Na]
+/ 431, [2M+H]
+/ 817 and [2M+Na]
+/ 839.Second order ms provides daughter ion [M-H-CH
3CO
2H]
-/ 347, [M-H-CH
3CO
2H-H
2O]
-/ 329, [M-H-CH
3CO
2H-2H
2O]
-/ 311, [M-H-CH
3CO
2H-CH
2O]
-/ 317, [M-H-CH
3CO
2H-CO
2]
-/ 303, [M-H-CH
3CO
2H-CH
2O-H
2O]
-/ 299 and [M-H-CH
3CO
2H-2H
2O-CH
2O]
-/ 281.These ions are consistent with the ion of rabdoternin D.Rabdoternin D is appointed as at peak 16 like this.
(-) ESI-Q-TOF-MS at peak 21 and (+) ESI-Q-TOF-MS provide [M-H]
-/ 361, [2M-H]
-/ 723, [M+H]
+/ 363, [M+Na]
+/ 385 and [2M+Na]
+/ 747.Second order ms provides daughter ion [M-H-H
2O]
-/ 343, [M-H-2H
2O]
-/ 325, [M-H-H
2O-CO
2]
-/ 299 and [M-H-H
2O-CO
2-CO]
-/ 271.These ions are consistent with the ion of ponicidin.Ponicidin is appointed as at peak 21 like this.
The content of phenolic acid and diterpene in embodiment 6 Rabdosia rubescens stem water extracts
Ion flow under HPLC-(+) ESI-Q-TOF-MS/MS detects is corresponding has confirmed that 6 kinds of phenolic acid of structure and the peak area of 4 kinds of diterpene (corresponding to peak 1,10,11,14,15,16,17,19,20 and 21) account for 72.81% of 22 peaks.
The platelet aggregation inhibitory activity evaluation of embodiment 7 Rabdosia rubescens stem water extracts
Pig carotid artery is got blood, with 3.8% sodium citrate (V
Sodium citrate: V
Whole blood=1: 9) anticoagulant.Centrifugal 10 minutes of 1000g/min platelet rich plasma (PRP), then with 3000g/min centrifugal 10 minutes, get platelet poor plasma (PPP).(derive from SIGMA company) induced platelet is assembled take collagen, platelet activating factor, thrombin and arachidonic acid as derivant.Rabdosia rubescens stem water extract physiological saline solution.The parallel survey of each data 6 times.
Table 1 is that Rabdosia rubescens stem water extract is to the suppression ratio of the platelet aggregation of collagen, platelet activating factor, thrombin and arachidonic acid-induction.Data show that Rabdosia rubescens stem water extract causes to four kinds the platelet aggregation that poly-agent causes obvious inhibitory action is arranged.
The IC of table 1 Rabdosia rubescens stem water extract anticoagulant
50(n=6)
The antithrombotic acitivity evaluation of embodiment 8 Rabdosia rubescens stem water extracts
With the front normal saline solution that Rabdosia rubescens stem water extract is made into three kinds of concentration, the dosage that is used in body is 5mg/kg, 25mg/kg and 100mg/kg.Positive drug Asprin is made into the 10g/L normal saline solution, i.e. the solution of 55.5mM (mM, be concentration unit), and the dosage that is used in body is 30mg/kg.Blank is normal saline, and anticoagulant is heparin sodium 0.42mg/ml normal saline solution.Body weight is approximately 250g SD male rat random packet, n=10, the volume of rat oral gavage is 3ml/kg, gavage is used urethane (20g/100ml after 30 minutes, 7ml/kg) anesthesia separates right carotid and left jugular vein, contains the prior polyethylene tube of the silk thread of precise weighing of 6cm with one and is full of the heparin sodium normal saline solution, one end inserts left jugular vein, and an end inserts right carotid.Blood flow flows into the left side vein from the right side tremulous pulse through polyethylene tube, takes out silk thread after 15 minutes and records wet weight of thrombus, and result is as shown in table 2
The oral Rabdosia rubescens stem of table 2 water extract is on the thrombotic impact of SD male rat
Result shows that Rabdosia rubescens stem water extract has obvious anti thrombotic action, is outstanding antithrombotic agents.
Claims (9)
1. the preparation technology of Rabdosia rubescens stem water extract, this technique comprises cleans chopping afterwards with dried Rabdosia rubescens stem with tap water, use the hot water diafiltration of 70-90 ℃ in the ratio of 1: 40 (g/mL), the speed that percolate flows out is 10-30mL/ minute, effluent obtains Rabdosia rubescens stem water extract dry powder in 40-60 ℃ of concentrating under reduced pressure.
2. method according to claim 1, wherein dried Rabdosia rubescens stem is 1: 30 (g/mL) with the ratio of the hot water that is used for diafiltration.
3. method according to claim 1, the temperature that wherein is used for the hot water of diafiltration is 80 ℃.
4. method according to claim 1, wherein the speed that flows out of percolate is 20mL/ minute.
5. method according to claim 1, wherein the temperature of effluent concentrating under reduced pressure is 50 ℃.
6. the Rabdosia rubescens stem water extract for preparing of the either method of claim 1-6, is characterized in that the dry powder that this Rabdosia rubescens stem water extract concentrating under reduced pressure obtains is faint yellow solid.
7. HPLC-PAD/ (-) the ESI-MS-MS finger printing of Rabdosia rubescens stem water extract.
8. HPLC-PAD/ (+) the ESI-MS-MS finger printing of Rabdosia rubescens stem water extract.
9. Rabdosia rubescens stem water extract is as the application of antithrombotic agents.
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| CN103142688A (en) * | 2011-12-07 | 2013-06-12 | 彭莉 | Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as anti-inflammatory agent |
| CN103142689A (en) * | 2011-12-07 | 2013-06-12 | 彭莉 | Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as free-radical scavenger |
| CN110698444A (en) * | 2019-10-30 | 2020-01-17 | 福建省中科生物股份有限公司 | Phenylpropanoid compound and preparation method thereof |
| CN110711189A (en) * | 2019-10-30 | 2020-01-21 | 福建省中科生物股份有限公司 | Application of compound in medicine |
| CN110698444B (en) * | 2019-10-30 | 2021-03-23 | 福建省中科生物股份有限公司 | Phenylpropanoid compound and preparation method thereof |
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