CN103381182B - The application of Houttuynoid C in preparation treatment myocardial ischemia drug - Google Patents
The application of Houttuynoid C in preparation treatment myocardial ischemia drug Download PDFInfo
- Publication number
- CN103381182B CN103381182B CN201310253924.8A CN201310253924A CN103381182B CN 103381182 B CN103381182 B CN 103381182B CN 201310253924 A CN201310253924 A CN 201310253924A CN 103381182 B CN103381182 B CN 103381182B
- Authority
- CN
- China
- Prior art keywords
- myocardial ischemia
- houttuynoid
- application
- preparation treatment
- control group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- FCUIRBQXJWMGLZ-YLUJEXTNSA-N 2-(3-decanoyl-7-hydroxy-1-benzofuran-4-yl)-5,7-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Chemical compound C=12C(C(=O)CCCCCCCCC)=COC2=C(O)C=CC=1C=1OC2=CC(O)=CC(O)=C2C(=O)C=1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O FCUIRBQXJWMGLZ-YLUJEXTNSA-N 0.000 title claims abstract description 38
- 208000031225 myocardial ischemia Diseases 0.000 title claims abstract description 23
- 239000003814 drug Substances 0.000 title claims abstract description 22
- 229940079593 drug Drugs 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 230000002265 prevention Effects 0.000 claims abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- 238000002474 experimental method Methods 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 238000003304 gavage Methods 0.000 description 7
- 210000004165 myocardium Anatomy 0.000 description 7
- JLTCWSBVQSZVLT-CDIPANDDSA-N (2s)-n-[(2s)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosan Chemical compound NCCCC[C@@H](C(=O)NCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](N)CSSC1.C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 JLTCWSBVQSZVLT-CDIPANDDSA-N 0.000 description 6
- 102000005320 Posterior Pituitary Hormones Human genes 0.000 description 6
- 108010070873 Posterior Pituitary Hormones Proteins 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 208000009889 Herpes Simplex Diseases 0.000 description 4
- 241000700584 Simplexvirus Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000003602 anti-herpes Effects 0.000 description 4
- 229930190556 houttuynoid Natural products 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 240000000691 Houttuynia cordata Species 0.000 description 3
- 235000013719 Houttuynia cordata Nutrition 0.000 description 3
- 206010063837 Reperfusion injury Diseases 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000003203 everyday effect Effects 0.000 description 3
- 229930003935 flavonoid Natural products 0.000 description 3
- 150000002215 flavonoids Chemical class 0.000 description 3
- 235000017173 flavonoids Nutrition 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000004 hemodynamic effect Effects 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- 229940011964 pentobarbital sodium 30 mg Drugs 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- 241000237970 Conus <genus> Species 0.000 description 1
- 206010011086 Coronary artery occlusion Diseases 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 208000007201 Myocardial reperfusion injury Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000001168 carotid artery common Anatomy 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 210000003017 ductus arteriosus Anatomy 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 229940079448 nitroglycerin 5 mg Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention provides the application of Houttuynoid C in preparation treatment or prevention myocardial ischemia drug.The Houttuynoid C that the present invention relates to belongs to first public preparing the purposes in medicaments for resisting myocardial ischemia, because framework types belongs to brand-new framework types, and its inhibit activities for myocardial ischemia is unexpectedly strong, there is not the possibility being provided any enlightenment by other compounds, possessing outstanding substantive distinguishing features, for resisting myocardial ischemia, obviously there is significant progress simultaneously.
Description
Technical field
The present invention relates to the application of Houttuynoid C in preparation treatment or prevention myocardial ischemia drug.
Background technology
The present inventor is found by a large amount of experiments, and Houttuynoid C has the/pharmacological action of reperfusion injury that resists myocardial ischemia, and has the medical usage of prevention or treatment myocardial ischemia disease.
The compound H outtuynoid C that the present invention relates to is one and delivers (Chen in 2012, S.D.et al., 2012.Houttuynoid A-E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletonsfrom Houttuynia cordata.Organic Letters 14 (7), 1772 – 1775.) New skeleton compound, this compound has brand-new framework types, current purposes only relates to anti-herpes simplex virus activity (Chen, S.D.et al., 2012.Houttuynoid A-E, Anti-Herpes Simplex Virus Active Flavonoids withNovel Skeletons from Houttuynia cordata.Organic Letters 14 (7), 1772 – 1775.), the Houttuynoid C that the present invention relates to is belonged to first public preparing the purposes in medicaments for resisting myocardial ischemia, because framework types belongs to brand-new framework types, and its inhibit activities for myocardial ischemia is unexpectedly strong, there is not the possibility being provided any enlightenment by other compounds, possesses outstanding substantive distinguishing features, for resisting myocardial ischemia, obviously there is significant progress simultaneously.
Summary of the invention
The invention provides Houttuynoid C to prepare treatment or prevent the application in the medicine of Ischemic/reperfusion.
The present inventor demonstrates by the experiment in detailed description of the invention the effect that Houttuynoid C has treatment or prevention myocardial ischemia drug disease.
Described compound H outtuynoid C-structure is as shown in formula I:
The Houttuynoid C that the present invention relates to belongs to first public preparing the purposes in medicaments for resisting myocardial ischemia, because framework types belongs to brand-new framework types, and its inhibit activities for myocardial ischemia is unexpectedly strong, there is not the possibility being provided any enlightenment by other compounds, possessing outstanding substantive distinguishing features, for resisting myocardial ischemia, obviously there is significant progress simultaneously.
Detailed description of the invention
The preparation method of compound H outtuynoid C involved in the present invention is see document (Chen, S.D.et al., 2012.Houttuynoid A-E, Anti-Herpes Simplex Virus Active Flavonoids with NovelSkeletons from Houttuynia cordata.Organic Letters 14 (7), 1772 – 1775.).
The present invention is further detailed explanation by the following examples, but protection scope of the present invention is not by any restriction of specific embodiment, but be limited by claim.
Embodiment 1: the preparation of compound H outtuynoid C tablet involved in the present invention:
Get 20 g of compound Houttuynoid C, add the customary adjuvant 180 grams preparing tablet, mixing, conventional tablet presses makes 1000.
Embodiment 2: the preparation of compound H outtuynoid C capsule involved in the present invention:
Get 20 g of compound Houttuynoid C, add prepare capsule customary adjuvant as starch 180 grams, mixing, encapsulatedly makes 1000.
Its pharmaceutically active is further illustrated below by pharmacodynamic experiment.
Experimental example: Houttuynoid C is on the impact of myocardial ischemia/reperfusion injury in rats
(1) experiment material: SD rat, male and female dual-purpose, body weight 190 ~ 210g.
(2) method and result
1) experimental technique
The acute myocardial ischemia experiment of pituitrin induction: rat is divided into 5 groups at random: positive drug control group, model control group, administration group 3 groups, often organizes 8.Administration group gastric infusion, positive drug control group and model control group give the distilled water gavage of consubstantiality accumulated amount every day, the continuous gavage 7d of each group.All after the 7th day gavage, 1.5 ~ 2.0h lumbar injection pentobarbital sodium 30mg/kg anaesthetizes, and adopts MS2302 multimedia biological signal collecting analytical system to continue record standard II lead electrocardiogram.The Electrocardiographic change of record 15min continuously after positive drug control group, model control group and administration group sublingual vein injection of pituitrin 5IU/kg (complete in 5s, positive drug control group is 10min lumbar injection nitroglycerin 5mg/kg before injection of pituitrin) 10min.If there is one of following change in electrocardiogram: T ripple is low flat, two-way, and be inverted, ST section level moves down >=0.05mV, gives note 1 point.Finally analyze the total score of every rat, as reduced after medication score, prompting myocardial ischemia is improved.The impact of medicine on heart rate is represented with changes in heart rate percentage rate before and after injection of pituitrin.
Cardiac muscle ischemia resisting reperfusion injury experiment: rat is divided into 5 groups at random: positive drug control group, model control group, administration group 3 groups, often organizes 8.Administration group gastric infusion, positive drug control group and model control group give the distilled water gavage of consubstantiality accumulated amount every day, the continuous gavage 7d of each group.Record standard II lead electrocardiogram after rats by intraperitoneal injection pentobarbital sodium 30mg/kg anaesthetizes.Tracheal intubation, meets artificial respirator (1.0mlg
-1min
-1), thoracic cavity is opened at 4th ~ 5 intercostals, expose heart, at pulmonary conus left border, left auricle lower edge 1mm place is with 320 silk thread ligation ramus descendens anterior arteriae coronariae sinistraes (positive drug control group 3min sublingual vein before following coronary artery occlusion injects Propranolol 1.0mg/kg).After ligation 30min, cut off ligature, fill with 30min again.Quick taking-up heart, rinses well with 0.9% sodium chloride.Myocardium sheet is placed in the TTC solution of 1%, in 37 DEG C of hatching 5min.Rinse with water immediately after dyeing and remove dyestuff unnecessary on myocardium sheet.Cut off the non-infarcted region cardiac muscle that each myocardium sheet is colored, undyed infarcted myocardium and ischemic myocardium are weighed.
Hemodynamics is tested: rat is divided into 5 groups at random: positive drug control group, model control group, administration group 3 groups, often organizes 8.Administration group gastric infusion, positive drug control group and model control group give the distilled water gavage of consubstantiality accumulated amount every day, the continuous gavage 5d of each group.Within 6th day, lumbar injection urethane 10mg/kg anaesthetizes.Record standard II lead electrocardiogram.Longitudinally cut right skin of neck, be separated right common carotid artery, insert the left ventricular catheter being full of heparin 0.9% sodium chloride, conduit is slowly inserted left ventricular cavity.Cut left lower extremity inside skin, be separated femoral artery, insert ductus arteriosus.Cut-in pressure transducer, transports to multimedia bio signal monitor signal and observes.After balance 30min, each hemodynamic index before record administration.
So data all represent with x ± s, experimental group and the matched group data analysis sided t of two sample averages are checked.
2) result
Ischemia/reperfusion injury experimental result shows, under administration group, positive drug control group, model control group myocardial infarction and ligature, myocardial Mass Measured percentage ratio is respectively in table 1.
Table 1 Houttuynoid C is on the impact of scheming weight ratio under myocardial infarction and ligature
Compare with model comparison, * * p<0.01, * p<0.05
Houttuynoid C on the impact of the acute myocardial ischemia that pituitrin causes in table 2.
Table 2 Houttuynoid C is on the impact of the acute myocardial ischemia that pituitrin causes
Compare with model comparison, * * p<0.01, * p<0.05
Conclusion: Houttuynoid CA can reduce the generation of myocardial infarction, Houttuynoid C obviously can change the change of electrocardio degree, does not change heart rate.More than experiment can illustrate, Houttuynoid C can prevention and therapy myocardial ischemia.
Claims (1)
1.Houttuynoid C preparation treatment or prevention myocardial ischemia drug in application, described compound H outtuynoid C-structure as
formula Ishown in:
formula I.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310253924.8A CN103381182B (en) | 2013-06-24 | 2013-06-24 | The application of Houttuynoid C in preparation treatment myocardial ischemia drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310253924.8A CN103381182B (en) | 2013-06-24 | 2013-06-24 | The application of Houttuynoid C in preparation treatment myocardial ischemia drug |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103381182A CN103381182A (en) | 2013-11-06 |
| CN103381182B true CN103381182B (en) | 2015-09-16 |
Family
ID=49489249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310253924.8A Active CN103381182B (en) | 2013-06-24 | 2013-06-24 | The application of Houttuynoid C in preparation treatment myocardial ischemia drug |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103381182B (en) |
-
2013
- 2013-06-24 CN CN201310253924.8A patent/CN103381182B/en active Active
Non-Patent Citations (1)
| Title |
|---|
| Chen,S.D.et al..Houttuynoid A-E,Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata.《Organic Letters》.2012,第14卷(第7期),第1772–1775页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103381182A (en) | 2013-11-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103638012B (en) | Application of Myrtucommuacetalone in medicine for treatment of myocardial ischemia | |
| CN108245502A (en) | Purposes of the rheum emodin succinyl ester type compound in medicaments for resisting myocardial ischemia is prepared | |
| CN102423308A (en) | Two bromophenol compounds and application of pharmaceutically-acceptable salts of two bromophenol compounds in preparation of protection drug | |
| CN103768051B (en) | The application of Eryngiolide A in preparation treatment myocardial ischemia drug | |
| CN103381182B (en) | The application of Houttuynoid C in preparation treatment myocardial ischemia drug | |
| CN103520170B (en) | Kadcoccitones A application in preparation treatment myocardial ischemia drug | |
| CN103393703B (en) | The application of Houttuynoid B in preparation treatment myocardial ischemia drug | |
| CN103356681B (en) | The application of Houttuynoid A in preparation treatment myocardial ischemia drug | |
| CN103356647B (en) | The application of Chukrasone A in preparation treatment myocardial ischemia drug | |
| CN103356595B (en) | The application of Chukrasone B in preparation treatment myocardial ischemia drug | |
| CN105412073A (en) | Application of Spirooliganone B in preparation of myocardial ischemia treatment drug | |
| CN103751182B (en) | The application of a kind of compound in treatment myocardial ischemia drug | |
| CN103479609A (en) | Application of Scopariusins in preparation of myocardial ischemia treatment medicines | |
| CN105412068A (en) | Application of Rearranged abietane diterpenoid in preparation of drugs for treating myocardial ischemia | |
| CN105250269A (en) | Application of Nagelamides X in preparation of drug for treating myocardial ischemia | |
| CN105380940A (en) | Use of Rhodomicranols B in preparation of drug for treating myocardial ischemia | |
| CN102988351A (en) | Application of Aphanamixoid A for preparing medicine for treating myocardial ischemia | |
| CN102861035B (en) | Application of Gypensapogenin B in medicine for treating myocardial ischemia | |
| CN105168207A (en) | Medicine for treating myocardial ischemia and application thereof | |
| CN106344579A (en) | Application of Fistulains A in drugs for myocardial ischemia treatment | |
| CN103381178A (en) | Application of Houttuynoid D in drug for treatment of myocardial ischemia | |
| CN103356676A (en) | Application of Houttuynoid E in medicine for treating myocardial ischemia | |
| CN103340886A (en) | Application of Polyflavanostilbene A in preparation of medicine for treating myocardial ischemia | |
| CN103479620A (en) | Application of Neonectrolide A to in preparation of medicament for treating myocardial ischemia | |
| CN103610678B (en) | The application of Trigolutesins A in treatment myocardial ischemia drug |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20171106 Address after: 401120 Chongqing Yubei District Food City Avenue 18 Chongqing advertising industrial park office space Patentee after: Chongqing San Mou science and Technology Development Co., Ltd. Address before: 210009 Gulou District, Jiangsu, Nanjing Gu Ping Kong, No. 4 Patentee before: Ding Shengyu |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20201223 Address after: 224200 No.88 Gangcheng Avenue, Dongtai coastal economic zone, Yancheng City, Jiangsu Province Patentee after: Dongtai Haibin science and Technology Pioneer Park Management Co., Ltd Address before: 401120 office building of Chongqing advertising industrial park, No.18, shifucheng Avenue, Yubei District, Chongqing Patentee before: CHONGQING SUMARTE TECHNOLOGY DEVELOPMENT Co.,Ltd. |