CN102872127B - Application of Houttuynoid C in medicament for preventing or treating pancreatic fibrosis - Google Patents
Application of Houttuynoid C in medicament for preventing or treating pancreatic fibrosis Download PDFInfo
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- CN102872127B CN102872127B CN 201210419472 CN201210419472A CN102872127B CN 102872127 B CN102872127 B CN 102872127B CN 201210419472 CN201210419472 CN 201210419472 CN 201210419472 A CN201210419472 A CN 201210419472A CN 102872127 B CN102872127 B CN 102872127B
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- houttuynoid
- pancreatic fibrosis
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- medicament
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- 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 58
- 206010016654 Fibrosis Diseases 0.000 title claims abstract description 24
- 230000004761 fibrosis Effects 0.000 title claims abstract description 24
- 239000003814 drug Substances 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 210000004907 gland Anatomy 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 11
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 5
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims description 5
- 229960002591 hydroxyproline Drugs 0.000 claims description 5
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims description 5
- GGLZPLKKBSSKCX-UHFFFAOYSA-N S-ethylhomocysteine Chemical compound CCSCCC(N)C(O)=O GGLZPLKKBSSKCX-UHFFFAOYSA-N 0.000 claims description 2
- 230000002946 anti-pancreatic effect Effects 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 5
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 210000000496 pancreas Anatomy 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 208000009889 Herpes Simplex Diseases 0.000 description 4
- 241000700584 Simplexvirus Species 0.000 description 4
- 230000003602 anti-herpes Effects 0.000 description 4
- 240000000691 Houttuynia cordata Species 0.000 description 3
- 235000013719 Houttuynia cordata Nutrition 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 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
- 229930190556 houttuynoid Natural products 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 208000032843 Hemorrhage Diseases 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000010562 histological examination Methods 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000000386 microscopy Methods 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 1
- RSBNUWAVVQOBHL-UHFFFAOYSA-N C(CC)O.CC1=C(C(=O)O)C=CC=C1C(=O)O Chemical compound C(CC)O.CC1=C(C(=O)O)C=CC=C1C(=O)O RSBNUWAVVQOBHL-UHFFFAOYSA-N 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000004923 pancreatic tissue Anatomy 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses application of Houttuynoid C in preparing a medicament for preventing or treating pancreatic fibrosis. The use of Houttuynoid C in preparing the anti-pancreatic fibrosis medicament involved in the invention is disclosed for the first time; as the framework type of Houttuynoid C is a brand new framework type and Houttuynoid C has an unexpectedly high inhibition activity forthe pancreatic fibrosis without possibility of giving any implication by other compounds, Houttuynoid C has outstanding substantive features; and simultaneously, the application of Houttuynoid C for preventing the pancreatic fibrosis apparently has obvious progress.
Description
Technical field
The present invention relates to the application of Houttuynoid C in pharmacy, relate in particular to the application of Houttuynoid C in the medicine of preparation prevention or treatment pancreatic gland fibrosis.
Background technology
The present sickness rate of pancreatic gland fibrosis is more and more high, is badly in need of the anti-pancreatic gland fibrosis medicine of research and development high-efficiency low-toxicity.
The compound H outtuynoid C that the present invention relates to is one and delivered (Chen in 2012, S. D. et al., 2012. Houttuynoid C_E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata. Organic Letters 14 (7), 1772 – 1775.) new framework compound, this chemical compound has brand-new framework types, present purposes only relates to anti-herpes simplex virus activity (Chen, S. D. et al., 2012. Houttuynoid C_E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata. Organic Letters 14 (7), 1772 – 1775.), belong to open first for the purposes of the Houttuynoid C that the present invention relates in the anti-pancreatic gland fibrosis medicine of preparation, because framework types belongs to brand-new framework types, and it suppresses active unexpectedly strong for pancreatic gland fibrosis, there is not the possibility that is provided any enlightenment by other chemical compounds, possess outstanding substantive distinguishing features, be used for anti-pancreatic gland fibrosis simultaneously and obviously have obvious improvement.
Summary of the invention
Technical problem to be solved by this invention is by the designing animal experimental technique, the anti-pancreatic gland fibrosis effect of research Houttuynoid C.
Described compound H outtuynoid C-structure is shown in formula I:
Formula I
Therefore, the purpose of this invention is to provide the application of Houttuynoid C in the medicine of preparation prevention or treatment pancreatic gland fibrosis.
Positive progressive effect of the present invention is: Houttuynoid C has the effect of anti-pancreatic gland fibrosis, so the application of Houttuynoid C has good DEVELOPMENT PROSPECT.
The purposes of the Houttuynoid C that the present invention relates in the anti-pancreatic gland fibrosis medicine of preparation belongs to open first, because framework types belongs to brand-new framework types, and it suppresses active unexpectedly strong for pancreatic gland fibrosis, there is not the possibility that is provided any enlightenment by other chemical compounds, possess outstanding substantive distinguishing features, be used for anti-pancreatic gland fibrosis simultaneously and obviously have obvious improvement.
The specific embodiment
The preparation method of compound H outtuynoid C involved in the present invention is referring to document (Chen, S. D. et al., 2012. Houttuynoid C_E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons 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 subjected to any restriction of specific embodiment, but limited by claim.
Embodiment 1: the preparation of compound H outtuynoid C tablet involved in the present invention:
Get 20 and digest compound Houttuynoid C, add conventional adjuvant 180 grams of preparation tablet, mixing, conventional tablet machine are made 1000.
Embodiment 2: the preparation of compound H outtuynoid C capsule involved in the present invention:
Get 20 and digest compound Houttuynoid C, add conventional adjuvant such as starch 180 grams of preparation capsule, mixing is encapsulatedly made 1000.
Further specify its pharmaceutically active below by pharmacodynamic experiment.
Experimental example:
1 material
1.1 animal Wistar rat is male, body weight 180-200g.
1.2 Houttuynoid C dosage: 0.3mg/kg, 0.9mg/kg, three dosage of 2.7mg/kg.
2 experimental techniques
2.1 modeling method Wistar rat with lumbar injection dl-ethionine 250 mg/ days, continuous 2 months, the pancreas glandular cell can occur and reduce, adipocellular hypertrophy in the matter.
2.2 grouping and medication
Rat model is divided into model group at random, Houttuynoid C 0.3mg/kg, 0.9mg/kg, three dosage groups of 2.7mg/kg, and other establishes the blank group, begins back administration, oral continuous 30 days in modeling; Dissect animal in the time of 60 days.
2.3 detection index
Weigh 2.3.1 get pancreas when experiment finishes, calculate organ coefficient.
2.3.2 the pancreas hydroxyproline content is measured and got the homogenate in water of 100mg sample, hydrolysis is 20 hours among 110 ℃ of 10 N HCl.HCl volatilizees with nitrogen, and hydrolyzate filters with distilled water dissolving back.Getting 0.5ml liquid mixes with the 1M periodic acid that 3ml citric acid phosphate buffer (the 0.15M citric acid adds the 0.6M sodium hydrogen phosphate) and 0.5ml are dissolved in 9M phosphoric acid.Add 1.75ml extract buffer (5 parts of toluene: 5 parts of 2-methyl isophthalic acid-propanol: 2 parts of 1-propanol), concussion 30min, centrifugal.Organize phase (0.6ml) and Ehrlich
,The s reagent mix is placed 15min.Measure trap at 565nm, with 4-hydroxyl-1-proline production standard curve calculation concentration, content is with the expression of ug/g tissue.
2.3.3 histological examination pancreas tissue 10% formalin fixed, paraffin embedding, dyeing back microscopy.To inflammatory cell infiltration, interstitial edema, fibrosis, pancreas room necrocytosis and hemorrhage situation scoring (0-3 branch).
3 results
3.1 the influence of Houttuynoid C rat pancreas weight and organ coefficient
When experiment finishes, rat is put to death, dissects, weigh in and pancreas is heavy and calculate it and the ratio of body weight, the results are shown in Table 1.The influence of the pancreas organ coefficient of Houttuynoid C relatively has significant difference with model group.
Table 1
* represent p＜0.05, compare with model group
3.2 the pancreas hydroxyproline content is measured
During experimental result, each group rat is carried out pulmonary's hydroxyproline content measure result such as table 2.The influence of the hydroxyproline content of Houttuynoid C relatively has significant difference with model group.
Table 2
* represent p＜0.05, compare with model group
3.3 histological examination
When experiment finishes, rat is put to death, dissects; The conventional embedding of specimen, fixing, HE dyeing, microscopy.
Result: model group visible pancreas conduit serious inflammatory reaction on every side in the 60th day; Granulocyte karyolymph cellular infiltration in having a liking for, interstitial edema, the necrosis of hemorrhage and accidental pancreas cystencyte; Fibrosis appears between pancreas cystencyte disappearance position and pancreas bubble.
But Houttuynoid C dose dependent reduces inflammatory reaction, tissue edema and fibrosis.Appraisal result sees Table 3.Houttuynoid C relatively has significant difference to the influence of scoring with model group.
Table 3
* represent p＜0.05, compare with model group
Conclusion: the present invention has confirmed the effect that Houttuynoid C has anti-pancreatic gland fibrosis by the Fibrotic influence of the pancreas in rat of Houttuynoid C.Therefore, Houttuynoid C can be used as active component for the preparation of the medicine of anti-pancreatic gland fibrosis.
Claims (1)
1.Houttuynoid C reduces the application in the hydroxyproline content medicine in the pancreatic gland fibrosis that the dl-ethionine causes in preparation, described compound H outtuynoid C-structure as
Formula IShown in:
Formula I.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210419472 CN102872127B (en) | 2012-10-27 | 2012-10-27 | Application of Houttuynoid C in medicament for preventing or treating pancreatic fibrosis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210419472 CN102872127B (en) | 2012-10-27 | 2012-10-27 | Application of Houttuynoid C in medicament for preventing or treating pancreatic fibrosis |
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| Publication Number | Publication Date |
|---|---|
| CN102872127A CN102872127A (en) | 2013-01-16 |
| CN102872127B true CN102872127B (en) | 2013-07-17 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1136073A1 (en) * | 2000-03-22 | 2001-09-26 | N.V. Nutricia | Compositions suitable for the treatment of damage caused by ischemia/reperfusion or oxidative stress |
| CN1519236A (en) * | 2003-09-01 | 2004-08-11 | ƽ | Compound of flavonoid as well as application and dosage form of extract product of the compound |
| CN1705473A (en) * | 2002-10-22 | 2005-12-07 | 詹肯生物科学公司 | Chromones and chromone derivatives and uses thereof |
-
2012
- 2012-10-27 CN CN 201210419472 patent/CN102872127B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1136073A1 (en) * | 2000-03-22 | 2001-09-26 | N.V. Nutricia | Compositions suitable for the treatment of damage caused by ischemia/reperfusion or oxidative stress |
| CN1705473A (en) * | 2002-10-22 | 2005-12-07 | 詹肯生物科学公司 | Chromones and chromone derivatives and uses thereof |
| CN1519236A (en) * | 2003-09-01 | 2004-08-11 | ƽ | Compound of flavonoid as well as application and dosage form of extract product of the compound |
Non-Patent Citations (2)
| Title |
|---|
| Shao-Dan Chen,等.Houttuynoids A-E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata.《Organic Letters》.2012,第14卷(第7期),1772-1775. * |
| Shao-DanChen，等.HouttuynoidsA-E Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata.《Organic Letters》.2012 |
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| CN102872127A (en) | 2013-01-16 |
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