CN102872090A - Application of Houttuynoid D in anti-bacterial agents - Google Patents
Application of Houttuynoid D in anti-bacterial agents Download PDFInfo
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- CN102872090A CN102872090A CN2012104186782A CN201210418678A CN102872090A CN 102872090 A CN102872090 A CN 102872090A CN 2012104186782 A CN2012104186782 A CN 2012104186782A CN 201210418678 A CN201210418678 A CN 201210418678A CN 102872090 A CN102872090 A CN 102872090A
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- houttuynoid
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- bacterial
- bacterial agents
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- 239000003242 anti bacterial agent Substances 0.000 title abstract 3
- ROCYDQPSKYPRJK-KXDBBDCJSA-N 2-[3,4-dihydroxy-2-(2-oxoundecyl)phenyl]-5,7-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Chemical compound CCCCCCCCCC(=O)CC1=C(O)C(O)=CC=C1C1=C(O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 ROCYDQPSKYPRJK-KXDBBDCJSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 229940124350 antibacterial drug Drugs 0.000 claims description 6
- 229930190556 houttuynoid Natural products 0.000 claims description 4
- OXBQNNYXKZSXES-RDHYKQKTSA-N 5,7-dihydroxy-2-(7-hydroxy-2-nonyl-1-benzofuran-4-yl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Chemical compound C1=CC(O)=C2OC(CCCCCCCCC)=CC2=C1C=1OC2=CC(O)=CC(O)=C2C(=O)C=1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O OXBQNNYXKZSXES-RDHYKQKTSA-N 0.000 abstract description 38
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 14
- 239000003814 drug Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 241000588724 Escherichia coli Species 0.000 abstract description 3
- 241000588769 Proteus <enterobacteria> Species 0.000 abstract description 3
- 230000001580 bacterial effect Effects 0.000 abstract description 2
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 2
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- 201000007336 Cryptococcosis Diseases 0.000 abstract 1
- 241000221204 Cryptococcus neoformans Species 0.000 abstract 1
- 241000589540 Pseudomonas fluorescens Species 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- 229940088710 antibiotic agent Drugs 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
- 208000015181 infectious disease Diseases 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000009707 neogenesis Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 1
- YWMSSKBMOFPBDM-UHFFFAOYSA-N 4-carbamoylbenzenesulfonyl chloride Chemical compound NC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 YWMSSKBMOFPBDM-UHFFFAOYSA-N 0.000 description 1
- 229930183010 Amphotericin Natural products 0.000 description 1
- QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229960004821 amikacin Drugs 0.000 description 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
- 229960001656 amikacin sulfate Drugs 0.000 description 1
- 229940009444 amphotericin Drugs 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229960004130 itraconazole Drugs 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000013641 positive control Substances 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
- 239000000126 substance Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to an application of Houttuynoid B in preparing anti-bacterial agents, and belongs to the field of medicines. Houttuynoid B has great inhibition effect on escherichia coli, pseudomonas fluorescence, staphyloccocus aureus, proteus and cryptococcus neoformans, and therefore can be used as an antibacterial compound and is expected to be applied in relevant medicines. The application of Houttuynoid B in preparing anti-bacterial agents is disclosed for the first time, has extremely high bacterial inhibitory activity as the skeleton type belongs to a completely novel skeleton type, has prominent substantive features and no any possibility for other compounds to give any inspiration, and simultaneously has remarkable progress when used for preventing and treating bacterial infection.
Description
Technical field
The present invention relates to the purposes of Houttuynoid B, relate in particular to the application of Houttuynoid B in the preparation anti-bacterial drug.
Background technology
Human health and lives in the diffusion of pathogenic bacterium and chemical sproof enhancing serious threat thereof, antibacterials are widely used in acquired immune deficiency syndrome (AIDS) as routine administration, organ transplantation and Chronic consumptions are (such as cancer, diabetes, uremia etc.) treatment, although the antimicrobial agent of using clinically at present is (such as ketoconazole, amikacin, gentamycin, voriconazole, itraconazole, terbinafine, amphotericin, fluconazol etc.) better to the curative effect of skin and superficial place infection, but the cumulative toxicity of these antibacterials is stronger, usually cause lesions of liver and kidney, digestive tract stimulates, dizzy, irritated etc., become one of focus of current medicament research and development so seek the novel antibacterial medicine of mechanism of action uniqueness.
The compound H outtuynoid B that the present invention relates to is one and delivered (Chen in 2012, S. D. et al., 2012. Houttuynoid B_E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata. Organic Letters 14 (7), 1772 – 1775.) New skeleton 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 B_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 B that the present invention relates in the preparation anti-bacterial drug, because framework types belongs to brand-new framework types, and it is active unexpectedly strong for bacteriostatic, there is not the possibility that is provided any enlightenment by other chemical compounds, possess outstanding substantive distinguishing features, the control that is used for simultaneously the antibacterial infection obviously has significant progress.
Summary of the invention
The object of the invention is to:
The application of a kind of Houttuynoid B of the present invention in the preparation anti-bacterial drug is provided.
Described compound H outtuynoid B structure is shown in formula I:
Formula I
Houttuynoid B has the effect of very strong inhibition escherichia coli, fluorescent pseudomonas, Staphylococcus aureus, Bacillus proteus, neogenesis cryptococcus, so Houttuynoid B can be used as the chemical compound with antibacterial action, and be expected in the preparation antibacterials, be applied.
The purposes of Houttuynoid B in the preparation anti-bacterial drug belongs to open first, because framework types belongs to brand-new framework types, and it is active unexpectedly strong for bacteriostatic, there is not the possibility that is provided any enlightenment by other chemical compounds, possess outstanding substantive distinguishing features, the control that is used for simultaneously the antibacterial infection obviously has significant progress.
The specific embodiment
The preparation method of compound H outtuynoid B involved in the present invention is referring to document (Chen, S. D. et al., 2012. Houttuynoid B_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 B tablet involved in the present invention:
Get 20 and digest compound Houttuynoid B, add conventional adjuvant 180 grams of preparation tablet, mixing, conventional tablet machine are made 1000.
Embodiment 2: the preparation of compound H outtuynoid B capsule involved in the present invention:
Get 20 and digest compound Houttuynoid B, 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: Houttuynoid B antibacterial activity
Antibacterial activity test is to adopt the method for concentration dilution, measures triplicate at every turn, and the test pathogen has escherichia coli, fluorescent pseudomonas, Staphylococcus aureus, Bacillus proteus, neogenesis cryptococcus, and bacterial concentration is 10
5Individual/mL.Houttuynoid B initial concentration is 50.0 μ g/mL(5% dimethyl sulfoxide DMSO), gradient dilution to 0.098 μ g/mL, the bacterium liquid of equivalent volumes and specimen Mixed culture are in 96 orifice plates, the antibacterial culturing temperature is respectively 37 ℃, observe behind the incubation time 24h, if discovery is the sample lowest concentration of antimicrobial when not having bacterium colony to form, i.e. the MIC value.This experiment positive control is amikacin sulfate, and Houttuynoid B the anti-bacterial result sees Table 1.
The antibiotic MIC value of table 1 Houttuynoid B (μ g/mL)
Conclusion: Houttuynoid B has very strong antibacterial activity, and therefore Houttuynoid B of the present invention is expected to be used to prepare the novel antibacterial medicine.
Claims (1)
1.Houttuynoid the application of B in anti-bacterial drug, described compound H outtuynoid B structure as
Formula IShown in:
Formula I.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104186782A CN102872090B (en) | 2012-10-27 | 2012-10-27 | Application of Houttuynoid D in anti-bacterial agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104186782A CN102872090B (en) | 2012-10-27 | 2012-10-27 | Application of Houttuynoid D in anti-bacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102872090A true CN102872090A (en) | 2013-01-16 |
| CN102872090B CN102872090B (en) | 2013-10-23 |
Family
ID=47473761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012104186782A Expired - Fee Related CN102872090B (en) | 2012-10-27 | 2012-10-27 | Application of Houttuynoid D in anti-bacterial agents |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102872090B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103027907A (en) * | 2012-11-19 | 2013-04-10 | 何晓涛 | Application of Aphanamixoid A in preparation of antibacterial drugs |
-
2012
- 2012-10-27 CN CN2012104186782A patent/CN102872090B/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| SHAO-DAN CHEN ET AL: "Houttuynoids A-E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata", 《ORG. LETT.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103027907A (en) * | 2012-11-19 | 2013-04-10 | 何晓涛 | Application of Aphanamixoid A in preparation of antibacterial drugs |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102872090B (en) | 2013-10-23 |
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Owner name: JIANGSU KANGHENG CHEMICAL CO., LTD. Free format text: FORMER OWNER: WU JUNHUA Effective date: 20141126 |
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Free format text: CORRECT: ADDRESS; FROM: 210009 NANJING, JIANGSU PROVINCE TO: 226500 NANTONG, JIANGSU PROVINCE |
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| TR01 | Transfer of patent right |
Effective date of registration: 20141126 Address after: 226500, Jiangsu, Rugao town (Rugao port area) 8 West Hong Kong Road (Fine Chemical Industry Park) Patentee after: Jiangsu Kangheng Chemical Co., Ltd. Address before: 210009 No. 22, Hankou Road, Gulou District, Jiangsu, Nanjing Patentee before: Wu Junhua |
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| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20131023 Termination date: 20191027 |
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| CF01 | Termination of patent right due to non-payment of annual fee |