CN103550215A - Applications of peptides compound in rhizome sparganii - Google Patents
Applications of peptides compound in rhizome sparganii Download PDFInfo
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- CN103550215A CN103550215A CN201310486948.8A CN201310486948A CN103550215A CN 103550215 A CN103550215 A CN 103550215A CN 201310486948 A CN201310486948 A CN 201310486948A CN 103550215 A CN103550215 A CN 103550215A
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Abstract
The invention discloses peptides in a kind of trigone to prepare the application in anticoagulation and/or antithrombotic reagent, shown in the peptides structural formula such as formula (I). The present invention provides for the first time to be isolated and purified to obtain the peptides from trigone and provides its application, the compound has the effect of extension trend to prothrombin time (PT), active partial thromboplastin time (APTT) and thrombin time (TT), with good anticoagulant active, provided a strong basis for the exploitation of antithrombotic natural drug.
(I).
Description
Technical field
The present invention relates to medical technical field, more specifically, relate to a kind of
threethe application of peptides in rib.
Background technology
Sparganium stoloniferum is Sparganiaceae plant rhizoma scirpi
sparganium stoloniferumthe dry tuber of Buch.-Ham, head is loaded in < < Bencao Shiyi > >, now for < < Chinese Pharmacopoeia > >, record, its bitter in the mouth, property are put down, enter liver, spleen channel, there is the functions such as removing blood stasis circulation of qi promoting, removing food stagnancy pain relieving.The traditional Chinese medical science is except alone raw product, vinegar goods, and Chang Peiwu Rhizoma Curcumae, the Radix Astragali etc. heighten the effect of a treatment.
Modern pharmacological research shows, in the middle of 35 kinds of conventional drug for invigorating blood circulation and eliminating stasis, the action intensity of Rhizoma Sparganii occupies first 10, and is widely used in cardiovascular and cerebrovascular disease, the treatment of tumor and gynecological's various diseases.Particularly, for Gynecological stubborn diseases such as hysteromyoma, endometriosis, Rhizoma Sparganii has shown the stronger dispelling the stagnated QI of invigorating blood circulation, the tired lame therapeutical effect that dissipates, and shows that the extensive exploitation of the aspects such as Liao Qi gynecological, tumor, hepatopathy and cardiovascular and cerebrovascular disease utilizes prospect.
But, the complex chemical composition of Rhizoma Sparganii, contain the compounds such as flavone and flavonoid glycoside, Phenylpropanoid Glycosides glycosides, steroidal and glycosides, organic acid, although modern chemistry and pharmacological research part have been illustrated the contact between chemical composition and clinical practice, but also have a lot of active component not found, a lot of pharmacological researches also only rest on the extract stage, have limited further applying of Rhizoma Sparganii compound.Therefore further disclose the contacting between applying with clinical medicine of chemical composition in Rhizoma Sparganii, for instructing clinical application and new drug development to have very important meaning.
Summary of the invention
The technical problem to be solved in the present invention is to fill up the deficiency of existing Rhizoma Sparganii compound application technology, provides
threethe application of peptides in rib.
Goal of the invention of the present invention is achieved by the following technical programs:
The application of peptides in preparing anticoagulation and/or antithrombotic reagent in a kind of Rhizoma Sparganii is provided, the structural formula of described compound as shown in the formula (I):
（Ⅰ）。
In described Rhizoma Sparganii, peptides comprises enantiomer, tautomer, physiology functional derivatives or the pharmaceutically acceptable salt of compound shown in formula I.
Further preferably, described compound is ring-(phenylalanine-tyrosine) [cyclo-(Phe-Tyr)].
Described compound can adopt the method for chemosynthesis to obtain.The present invention provides a kind of method for extraction and purification to prepare the compound of structure shown in formula I simultaneously, comprises the following steps:
S1. take Rhizoma Sparganii medical material, pulverize, add ethanol extraction, after extracting solution decompression and solvent recovery, obtain ethanol extract; Through the present invention continuous experimental summary, obtain, adopt 60%(v/v) ethanol the highest to the extraction ratio of Rhizoma Sparganii medicinal material extract, preferably adopt 60%(v/v) ethanol;
S2. by ethanol extract aqueous dispersion, be extracted with ethyl acetate, combined ethyl acetate part, after decompression and solvent recovery, obtains ethyl acetate extract;
S3. adopt silica gel chromatographic column to carry out separation to ethyl acetate extract, with chloroform-methanol solvent system, carry out gradient elution, Fr38-40 merges, after reclaiming solvent, use dissolve with methanol, room temperature is placed, and obtains white, needle-shaped crystals, obtains compound ring-(phenylalanine-tyrosine);
Fr41-43 merges, and through silica gel column chromatography segmentation, with chloroform-methanol solvent system (25:1,20:1,10:1), carries out gradient elution, and Fr2-4 merges, and room temperature is separated out white, needle-shaped crystals after placing, and obtains compound ring-(phenylalanine-tyrosine).
The compound that the present invention adopts said extracted purification process to prepare has good anticoagulant active, can be advantageously applied to and prepare antithrombotic reagent aspect.
The present invention has following beneficial effect:
The present invention has summed up the process conditions of science through great many of experiments, adopt the separation first from Sparganium stoloniferum of suitable method to obtain a kind of CYCLIC DIPEPTIDES compounds, and confirmed that through great many of experiments it is to prothrombin time (prothrombin time, PT), activated partial thromboplastin time (activated partial thrombop lastintime, APTT) and thrombin time (thrombin time, TT) there is prolongation trend, there is good anticoagulant active, filled up prior art blank, for the exploitation of antithrombotic natural drug provides new foundation.
Accompanying drawing explanation
Fig. 1 is the extraction route map of Rhizoma Sparganii effective site.
Fig. 2 is the rough segmentation flow chart of ethyl acetate extract.
Fig. 3 is the segmentation flow chart of Fr41-43 section.
Fig. 4 the compounds of this invention
13c-NMR spectrogram.
Fig. 5 the compounds of this invention
1h-NMR spectrogram.
Fig. 6 the compounds of this invention affects result figure to prothrombin time.
Fig. 7 the compounds of this invention affects result figure to activated partial prothrombin time.
Fig. 8 the compounds of this invention affects result figure to thrombin time.
The specific embodiment
Below in conjunction with the drawings and specific embodiments, further illustrate the present invention, the reagent that the embodiment of the present invention adopts is unless stated otherwise conventional commercial reagent, and unless stated otherwise, the equipment of employing and method are equipment and the method for the art routine.But therefore do not limit the present invention.
embodiment 1the extraction of compound shown in formula I, separation and purification and Structural Identification
1, experiment material:
(1) medical material
Rhizoma Sparganii medical material is write pharmaceutcal corporation, Ltd purchased from Guangzhou, and lot number is that 090301 professor Li Shuyuan of TCD identification teaching and research room of Chinese medicine institute of ，Jing Guangdong Pharmaceutical University is accredited as Sparganiaceae Sparganium plant rhizoma scirpi
sparganium stoloniferumthe prune dry tuber of crust of Buch.-Ham.
(2) reagent and filler
Chloroform (analytical pure, Tianjin Fu Yu Fine Chemical Co., Ltd);
Methanol (analytical pure, Tianjin Fu Yu Fine Chemical Co., Ltd);
Vanillin (Guang Lianjin chemical plant, Guangzhou);
Silica gel for column chromatography (80-100 order, 100-200 order, 200-300 Mu， Haiyang Chemical Plant, Qingdao);
Tlc silica gel (silica gel G, Qingdao Marine Chemical Co., Ltd.);
Sulphuric acid (analytical pure, Shanghai Shen Xiang chemical reagent company limited);
Sodium carboxymethyl cellulose CMC-Na(Shanghai Condar Chemical Engineering Technology service department).
(3) experimental apparatus
6202 miniature high-speed pulverizers (Beijing Huan Ya Tianyuan Mechanical Technology Inc.);
EC-1500/VC-600 type extracts thickener (Taiwan unit becomes mechanical limited company) automatically;
AGX1-2001-P type Ai Kepu (Aquapro) ultra-pure water system (Chongqing Yi Yang enterprise development company limited);
RE-52A type Rotary Evaporators (Shanghai Yarong Biochemical Instrument Plant);
SHZ-D type circulating water type vacuum pump (Gongyi City, Henan Ying Yu instrument plant);
GZX digital display air dry oven (Shanghai Bo Xun Medical Equipment Plant);
DLSB type low-temperature cooling fluid circulating pump (Zhengzhou Greatwall Scientific Industrial & Trading Co., Ltd.);
KQ-100 type ultrasonic cleaner (Kunshan Ultrasonic Instruments Co., Ltd.);
Japan Yanaco MP-S3 type micro melting point apparatus;
Electric-heated thermostatic water bath (HHS type, Shanghai Medical Equipment Plant of Bo Xun Industrial Co., Ltd.);
Thin layer automatic coating device (YOKO-BF, Wuhan Yao Ke new technology development company);
Superconduction pulse fourier transform nmr spectrogrph: Bruker AVANCE AV 500;
Superconduction pulse fourier transform nmr spectrogrph: Varian UNITY INOVA 500.
2, the extraction of medical material:
Extraction process route map as shown in Figure 1.The dry tuber 14kg that gets Sparganium stoloniferum, is ground into coarse powder, puts in multi-function extractor, with 60%(v/v) alcohol heating reflux extracts three times, and each two hours, filter, merge subsequent filtrate, reclaim ethanol, dry, obtain total extractum 752g.Total extractum is suspended in water, and ultrasonic 20min, uses petroleum ether, chloroform, ethyl acetate, n-butanol extraction three times successively, merge each extract, reclaim under reduced pressure, obtains petroleum ether part extractum 26g, chloroform extract extractum 34g, ethyl acetate extract extractum 11.5g, n-butanol portion extractum 42g.
3, the separation and purification of composition:
By gained ethyl acetate extract 11.5g extractum, use about 50ml acetic acid ethyl dissolution sample, dry method is mixed sample, through silica gel (200～300 order) column chromatography rough segmentation, to carry out gradient (100:1 with chloroform-methanol solvent system, 20:1,10:1,5:1, volume ratio) eluting, TLC inspects, and merges thin layer behavior phase homogeneous turbulence part.The attached rough segmentation flow chart that Figure 2 shows that ethyl acetate extract.In accompanying drawing 2, in square frame, alphabetical A represents the compounds of this invention.
(1) Fr38-40 merges, and uses Rotary Evaporators to concentrate, then uses dissolve with methanol, and room temperature is placed, and obtains white, needle-shaped crystals, obtains described compound.
(2) stream part Fr41-43 being merged, concentrating under reduced pressure, dissolves with appropriate chloroform, and dry method is mixed sample, through silica gel (200～300 order) column chromatography, segment, with chloroform-methanol solvent system (25:1,20:1,10:1, volume ratio), carry out gradient elution, TLC inspects, merge phase homogeneous turbulence part, Fr2-4 is merged, and room temperature is separated out white, needle-shaped crystals after placing, and obtains described compound.The attached segmentation flow chart that Figure 3 shows that Fr41-43 section, in square frame, alphabetical A represents the compounds of this invention.
The Structural Identification of the compound that said method separation obtains:
Colourless acicular crystal (methanol), m.p.301 ~ 303 ℃,
1in H-NMR (500MHz, DMSO) spectrum, δ 7.27 (2H, m), δ 7.20 (1H, m), δ 7.05 (2H, t, J=8.28Hz), show in molecule and have monosubstituted phenyl, according to its chemical shift, substituent group can only be alkane etc., and can not be remarkable electron-donating group or electron withdraw group; δ 6.84 (2H, d, J=8.40Hz), δ 6.67 (2H, d, J=8.4Hz), shows in molecule and has para-orientation phenyl structure fragment, its chemical shift prompting may have hydroxyl coupled; High field region also shows δ 3.94 (1H, brt.), δ 3.88 (1H, brd.), and δ 2.58 (2H, m) and δ 2.21 (2H, m), be the H signal in saturated carbon.
13c-NMR (500MHz, DMSO) spectrum provides 18 carbon signals.
By right
13the careful analysis of C-NMR can find, has 3 pairs of extremely approaching signals in number in molecule, is respectively δ 166.2 and δ 166.1, δ 55.7 and δ 55.4, and δ 39.9 and δ 39.3, corresponding group is 2 amide groups, 2 CH, 2 CH2; Infer thus, these former molecular structure fragments should be symmetrical structure, and its data difference comes from different that phenyl that 2 ends connect affects its chemical shift with p-hydroxybenzene.
This compound structure attribution data is as follows:
1 h-NMR (500MHz, DMSO):δ 9.22 (1H, s, OH), 7.86 (2H, s, CONH), 7.27 (2H, t,
j=7.0Hz, Phe-3 ', 5 '), 7.20 (1H, t,
j=7.5Hz, Phe-4 '), 7.05 (2H, t, Phe-2 ', 6 '), 6.84 (2H, d, J=8.4Hz, Tyr-2 ', 6 '), 6.67 (2H, d, J=8.40Hz, Tyr-3 ', 5 '), 3.94 (1H, brt, Tyr-α), 3.88 (1H, brd, Phe-α), 2.58 (2H, m, Phe-β) and 2.21 (2H, m, Tyr-β).
13 ，DMSO)：δ166.2(Tyr-co)，166.1(Phe-co)，156.1(Tyr-4′)，?136.6(Phe-1′)，130.7(Tyr-2′，6′)，129.7(Phe-3′，5′)，128.2(Phe-2′，6′)，126.4(Phe-4′?and?Tyr-1′)，115.0(Tyr-3′，5′)，55.7(Tyr-α)，55.4(Phe-α)，39.9(Tyr-β)，39.3(Phe-β)。
As shown in accompanying drawing 4 and accompanying drawing 5.According to above-mentioned spectral data, and contrast the nuclear magnetic data of having reported, thereby determined that the structure of this compound is ring-(phenylalanine-tyrosine).
The structural formula of described compound is as shown in the formula (I):
（Ⅰ）。
embodiment 2compound anticoagulant functions test of the present invention
1, experiment material
(1) medicine
(2) laboratory animal
SD rat, body weight 180～250g ，You Traditional Chinese Medicine University Of Guangzhou Experimental Animal Center provides.
(3) reagent
Heparin (sigma, lot number: 20120509);
Chloral hydrate (Guangzhou Si Le biochemical reagents company limited);
(Bioengineering Research Institute is built up in Nanjing to prothrombin time PT test kit, lot number: 20130314);
(Bioengineering Research Institute is built up in Nanjing to activated partial thromboplastin time APTT test kit, lot number: 20130201);
(Bioengineering Research Institute is built up in Nanjing to thrombin time TT test kit, lot number: 20130314);
Normal saline (world, Guizhou pharmaceutcal corporation, Ltd, lot number A13011209);
Dimethyl sulfoxide (DMSO) (analytical pure, Guangzhou Chemical Reagent Factory);
Sodium citrate (analytical pure, Tianjin Chemical Co., Ltd.'s all generations, lot number: 0110).
(4) experimental apparatus
Desk centrifuge (Beijing Medical Centrifugal Machine Factory);
Electric-heated thermostatic water bath (HHS type, Shanghai Medical Equipment Plant of Bo Xun Industrial Co., Ltd.);
FA1104 type electronic analytical balance (Shanghai balance equipment factory);
Stopwatch (upper Asterias amurensis Lutken is bored stopwatch company limited);
EP manages (Shanghai Shen Xiang chemical reagent company limited);
Liquid-transfering gun (Beijing China Correspondent development in science and technology company limited);
Syringe (Shanghai Chu setting analysis Instrument Ltd.).
2, experimental technique:
(1) blood plasma preparation
10% chloral hydrate for rat (350mg/kg) intraperitoneal injection of anesthesia, abdominal aortic blood, is sub-packed in containing 0.4ml, the plastic centrifuge tube of 109mmol/L sodium citrate anti-freezing liquid, every pipe 3.6mL, puts upside down and mixes gently immediately.The centrifugal 15min of 3000rpm, collects supernatant, obtains platelet poor plasma (PPP), test, or-20 ℃ frozen standby in 2 hours.
(2) anticoagulating active is measured
Carry out compound on prothrombin time, activated partial thromboplastin time and the impact experiment that affects thrombin time.Specific experiment operation operates according to prothrombin time PT test kit, activated partial thromboplastin time APTT test kit and the explanation of thrombin time TT test kit respectively.
(3) outcome record
Add corresponding reagent to mix immediately and start stopwatch, test tube is still dipped in water-bath, during to about 10s, take out,
Every 2s, upwards provoke to generating solid filament and stop timing, repeat above operation 3 times, get average and obtain PT, APTT or TT time.
3, experimental result and evaluation:
The results are shown in Table 1 and accompanying drawing 6～8 shown in.
Table 1
Result shows, aspect coagulation function, more blank group of the PT of test-compound group, APTT and TT value all have prolongation trend, illustrate that the compounds of this invention has anticoagulant effect.
The present invention's separated compound obtaining from Sparganium stoloniferum has prolongation trend to prothrombin time (PT), activated partial thromboplastin time (APTT) and thrombin time (TT), there is good anticoagulant active, for the exploitation of antithrombotic natural drug provides strong foundation.
Claims (4)
1. the application of peptides in preparing anticoagulation and/or antithrombotic reagent in Rhizoma Sparganii, the structural formula of described compound as shown in the formula (I):
（Ⅰ）。
2. application according to claim 1, is characterized in that, in described Rhizoma Sparganii, peptides comprises enantiomer, tautomer, physiology functional derivatives or the pharmaceutically acceptable salt of compound shown in formula I.
3. application according to claim 1, is characterized in that, in described Rhizoma Sparganii, peptides is ring-(phenylalanine-tyrosine).
4. application according to claim 3, is characterized in that, described ring-(phenylalanine-tyrosine) is by following steps, to extract purification to obtain:
S1. take Rhizoma Sparganii medical material, pulverize, add 60% ethanol extraction, after extracting solution decompression and solvent recovery, obtain ethanol extract;
S2. by ethanol extract aqueous dispersion, be extracted with ethyl acetate, combined ethyl acetate part, after decompression and solvent recovery, obtains ethyl acetate extract;
S3. adopt silica gel chromatographic column to carry out separation to ethyl acetate extract, with chloroform-methanol solvent system, carry out gradient elution, Fr38-40 merges, after reclaiming solvent, use dissolve with methanol, room temperature is placed, and obtains white, needle-shaped crystals, obtains compound ring-(phenylalanine-tyrosine);
Or Fr41-43 is merged, through silica gel column chromatography segmentation, with chloroform-methanol solvent 25:1,20:1,10:1 system, carrying out gradient elution, Fr2-4 merges, and room temperature is separated out white, needle-shaped crystals after placing, and obtains compound ring-(phenylalanine-tyrosine).
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108904502A (en) * | 2018-08-24 | 2018-11-30 | 广东药科大学 | The anti-syndrome of blood stasis application of scirpusin ingredient B in trigone |
| CN108926566A (en) * | 2018-08-24 | 2018-12-04 | 广东药科大学 | The anti-syndrome of blood stasis application of scirpusin ingredient A in trigone |
| CN109172577A (en) * | 2018-08-24 | 2019-01-11 | 广东药科大学 | The anti-syndrome of blood stasis application of scirpusin ingredient C in trigone |
| CN113694066A (en) * | 2021-08-13 | 2021-11-26 | 广东药科大学 | Application of scirpusin C in preparation of medicine for treating cerebral ischemic stroke |
-
2013
- 2013-10-17 CN CN201310486948.8A patent/CN103550215B/en active Active
Non-Patent Citations (3)
| Title |
|---|
| 胡旭光等: "不同三棱提取物药理活性的比较研究", 《陕西中医》 * |
| 董学等: "三棱的化学成分", 《药学学报》 * |
| 董学等: "中药三棱的化学成分及药理研究进展", 《齐鲁药事》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108904502A (en) * | 2018-08-24 | 2018-11-30 | 广东药科大学 | The anti-syndrome of blood stasis application of scirpusin ingredient B in trigone |
| CN108926566A (en) * | 2018-08-24 | 2018-12-04 | 广东药科大学 | The anti-syndrome of blood stasis application of scirpusin ingredient A in trigone |
| CN109172577A (en) * | 2018-08-24 | 2019-01-11 | 广东药科大学 | The anti-syndrome of blood stasis application of scirpusin ingredient C in trigone |
| CN109172577B (en) * | 2018-08-24 | 2021-03-16 | 广东药科大学 | Application of burreed tuber component C in rhizoma sparganii in preparation of anti-blood stasis medicine |
| CN108904502B (en) * | 2018-08-24 | 2021-03-16 | 广东药科大学 | Application of burreed tuber component B in rhizoma sparganii in preparation of anti-blood stasis medicine |
| CN113694066A (en) * | 2021-08-13 | 2021-11-26 | 广东药科大学 | Application of scirpusin C in preparation of medicine for treating cerebral ischemic stroke |
| CN113694066B (en) * | 2021-08-13 | 2023-02-17 | 广东药科大学 | Application of scirpusin C in preparation of medicine for treating cerebral ischemic stroke |
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