CN113912484A - 1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compound and application thereof in preparation of bacteriostatic agent - Google Patents
1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compound and application thereof in preparation of bacteriostatic agent Download PDFInfo
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- CN113912484A CN113912484A CN202110675730.1A CN202110675730A CN113912484A CN 113912484 A CN113912484 A CN 113912484A CN 202110675730 A CN202110675730 A CN 202110675730A CN 113912484 A CN113912484 A CN 113912484A
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- 229940076442 9,10-anthraquinone Drugs 0.000 title claims abstract description 11
- 239000000022 bacteriostatic agent Substances 0.000 title abstract description 4
- 241000194021 Streptococcus suis Species 0.000 claims abstract description 14
- 241000186810 Erysipelothrix rhusiopathiae Species 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 34
- 241000191967 Staphylococcus aureus Species 0.000 claims description 12
- -1 pentylcarboxy Chemical group 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 3
- 241000186811 Erysipelothrix Species 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 12
- 241000191940 Staphylococcus Species 0.000 abstract 1
- 239000000273 veterinary drug Substances 0.000 abstract 1
- 229940124350 antibacterial drug Drugs 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 208000022362 bacterial infectious disease Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 208000035143 Bacterial infection Diseases 0.000 description 3
- 201000000297 Erysipelas Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000187180 Streptomyces sp. Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000011482 antibacterial activity assay Methods 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 206010048282 zoonosis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/16—Quinones the quinoid structure being part of a condensed ring system containing three rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to the technical field of medicinal chemistry, and particularly discloses a 1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compound and application thereof in preparation of a bacteriostatic agent, wherein an antibacterial activity test shows that the 1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compound can remarkably inhibit staphylococcus aureusStaphylococcus aureus) Erysipelothrix rhusiopathiae (II)Erysipelothrix rhusiopathiae) And Streptococcus suis (Streptococcus suis) Has the application of preparing a novel antibacterial veterinary drug.
Description
Technical Field
The invention belongs to the technical field of pharmaceutical chemistry, and particularly relates to a 1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compound and application thereof in preparation of a bacteriostatic agent.
Background
Bacterial infections have been a significant threat to human and animal health. Streptococcus suis (Streptococcus suis) is an important bacterial infectious disease pathogen, has the characteristics of wide prevalence and strong pathogenicity, is an important zoonosis infectious disease pathogen, can cause various diseases of various animals including human and pigs, causes infection and even death, and seriously influences the development of pig industry and human health. Erysipelas suis (erysipelothrix rhusiopathiae) is a pathogenic bacterium of erysipelas suis, which occasionally causes infections of humans, birds, lambs, etc., and erysipelas-like occurs after human infection. Antibiotics play an important role in controlling bacterial infection, and the emergence of clinical multi-drug-resistant strains and super-drug-resistant bacteria all suggest that the existing antibacterial drugs can not meet the requirements of preventing and controlling bacterial infection of animals and human beings, so that the research of new antibacterial drugs is urgently needed.
The applicant obtained 8 1,4, 6-trihydroxy-8-branched Anthraquinone compounds (compounds 1-8) in the past, and found that this series of compounds have better antitumor activity [ Wu Mega et al, anticancer analytes from a Soil activating microorganisms sp.WS-13394and the same biological activities. Natural Product Research,2018,32(4): 412-) -417; wu Mega, et al, New Cytoxic Alkylated Anthraquinone antibodies from a Soil activating Streptomyces sp.WS-13394, Chemical & Pharmaceutical Bulletin,2014,62(1): 118-.
On the basis of the structures of the compounds 1-8, the applicant further obtains the compounds 9-11, and finds that the compounds 1-11 have obvious growth inhibition effects on bacteria, particularly staphylococcus aureus, erysipelothrix rhusiopathiae and streptococcus suis, and the compounds are not reported in domestic and foreign documents.
Disclosure of Invention
The invention aims to provide a 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound, which has the following structural formula:
wherein R is: propyl, butyl, isoamyl, pentyl, pentylcarboxy, 2 ' -carbonylpentyl, 2 ' -carbonylhexyl, hexyl, 2 ' -hydroxypropyl, 4 ' -hydroxyisopentyl or 2 ' -hydroxypentyl.
The invention also aims to provide application of the 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound in preparation of bacterial bacteriostat.
In order to achieve the purpose, the invention adopts the following technical measures:
1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compounds, the structural formula of the compounds is as follows:
wherein R is: propyl, butyl, isoamyl, pentyl, pentylcarboxy, 2 ' -carbonylpentyl, 2 ' -carbonylhexyl, hexyl, 2 ' -hydroxypropyl, 4 ' -hydroxyisopentyl or 2 ' -hydroxypentyl.
When the above R is different groups, the compounds are named as compounds 1 to 11 in sequence, and specifically, the structural formulas of the compounds 1 to 11 are as follows:
the protection scope of the invention also includes: the 1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compound is applied to the preparation of a bacterial inhibitor.
In the above applications, preferably, the bacteria are Staphylococcus aureus (Staphylococcus aureus), erysipelothrix rhusiopathiae (erysipelothrix rhusiopathiae), and/or Streptococcus suis (Streptococcus suis).
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. currently, the antibacterial drugs used clinically are mainly cyclic peptides, macrolides and penicillins. The related structure of the invention is completely different from the skeleton type of the antibacterial drugs used clinically at present, and the related structure is a 1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compound. Antibacterial drugs further developed based on the compounds can completely avoid the existing drug patents on the market, and provide more choices for the market.
2. The invention discovers 9-11 novel compounds and discovers that 1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compounds have activity of resisting staphylococcus aureus, streptococcus suis and erysipelothrix rhusiopathiae for the first time.
3. The results of antibacterial experiments show that the compounds 1, 2, 4, 5, 8 and 10 have significant antibacterial activity (MIC <0.78 mu g/mL) on Staphylococcus aureus, and the compounds 3, 6, 9 and 11 also have stronger antibacterial activity (MIC is 6.25, 1.56, 0.78 and 1.56 mu g/mL respectively) on Staphylococcus aureus; the compounds 3, 9 and 10 have stronger antibacterial activity to erysipelothrix rhusiopathiae (MIC is 3.125, 6.25 and 3.125 mu g/mL respectively); compounds 1, 2, 3, 4and 8 have potent antibacterial activity against Streptococcus suis (MICs of 6.25, 3.125, 6.25, 3.125 and 1.56. mu.g/mL, respectively). Therefore, the 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound has potential application in preparing novel antibacterial drugs.
Detailed Description
The present invention is further described in detail below with reference to specific examples, which are provided for illustration only and are not intended to limit the scope of the present invention. The test methods used in the following examples are all conventional methods unless otherwise specified; the materials, reagents and the like used are, unless otherwise specified, commercially available reagents and materials.
Example 1:
1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compounds, the structural formula of the compounds is as follows:
wherein R is: propyl, butyl, isoamyl, pentyl, pentylcarboxy, 2 ' -carbonylpentyl, 2 ' -carbonylhexyl, hexyl, 2 ' -hydroxypropyl, 4 ' -hydroxyisopentyl or 2 ' -hydroxypentyl.
When the above R is different groups, the compounds are named as compounds 1 to 11 in sequence, and specifically, the structural formulas of the compounds 1 to 11 are as follows:
among these, the applicants of compounds 1 to 8 have reported that the structure-identified UV, HR-ESI-MS and NMR spectra of compounds 9 to 11 are as follows:
compounds 9-11 were all red powders and the common UV absorption spectrum (466, 277, 225nm) indicated that these compounds all had a common 1,4,6, 8-substituted anthraquinone backbone.
HR-ESI-MS data: compound 9(M/z337.0688, [ M + Na ]]+) The molecular formula is deduced to be C17H14O6. Compound 10(M/z365.0994, [ M + Na ]]+) The molecular formula is deduced to be C19H18O6(ii) a Compound 11(M/z365.0994, [ M + Na ]]+) The molecular formula is deduced to be C19H18O6。
The NMR data are as follows:
TABLE 1 preparation of compounds 9-11(DMSO-d6)1H-NMR (500MHz) data (. delta.)H,J Hz)
TABLE 2 preparation of compounds 9-11(DMSO-d6)13C-NMR data (125MHz) data
Example 2:
compounds 1-11 antibacterial activity assay:
the method comprises the steps of selecting Staphylococcus aureus (Staphylococcus aureus), erysipelothrix rhusiopathiae (erysipelothrix rhusiopathiae), Streptococcus suis (Streptococcus suis), Escherichia coli (Escherichia coli) and Pseudomonas aeruginosa (Pseudomonas aeruginosa) strains, carrying out subculture on a nutrient agar slant culture medium for 1 time, inoculating the strains into a nutrient broth culture medium, culturing at 37 ℃ for 6-12 hours, and placing the culture medium in a refrigerator for later use. Taking a sample to be tested and positive controls (streptomycin and penicillin), sequentially diluting the sample to be tested and the positive controls to 100 mu g/mL, 50 mu g/mL, 25 mu g/mL, 12.5 mu g/mL, 6.25 mu g/mL, 3.125 mu g/mL, 1.56 mu g/mL and 0.78 mu g/mL by using a culture solution, shaking and mixing the samples, taking 1mL to transfer the samples to a 96-well plate, taking a culture medium as a blank control, selecting 3 repetitions of blank and each concentration, repeating the experiment for 3 times, culturing the samples at 37 ℃ for 12-18 h, measuring the absorbance by using a microplate reader at 630nm, and determining the MIC value.
As a result: compounds 1, 2, 4, 5, 8 and 10 had significant antibacterial activity against staphylococcus aureus (MIC <0.78 μ g/mL), compounds 3, 6, 9 and 11 also had stronger antibacterial activity against staphylococcus aureus (MIC of 6.25, 1.56, 0.78 and 1.56 μ g/mL, respectively); the compounds 3, 9 and 10 have stronger antibacterial activity to erysipelothrix rhusiopathiae (MIC is 3.125, 6.25 and 3.125 mu g/mL respectively); compounds 1, 2, 3, 4and 8 have potent antibacterial activity against Streptococcus suis (MICs of 6.25, 3.125, 6.25, 3.125 and 1.56. mu.g/mL, respectively).
TABLE 3 inhibitory Effect of Compounds 1-11 on three bacteria (MIC. mu.g/ml)
"-" indicates no antibacterial activity at a drug concentration of 100. mu.g/ml or less
The above examples are for illustration only and are not intended to limit the scope of the present invention. Various changes and modifications can be made by one skilled in the art, and such equivalent changes and modifications are also intended to be included within the scope of the invention as defined in the appended claims.
Claims (2)
1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compounds, the structural formula of which is as follows:
wherein R is: 2 ' -hydroxypropyl, 4 ' -hydroxyisopentyl or 2 ' -hydroxypentyl.
2.1,4, 6-trihydroxy-8-branched-chain-9, 10-anthraquinone compound is applied to the preparation of bacterial bacteriostat;
the structural formula of the compound is as follows:
wherein R is: propyl, butyl, isoamyl, pentyl, pentylcarboxy, 2 ' -carbonylpentyl, 2 ' -carbonylhexyl, hexyl, 2 ' -hydroxypropyl, 4 ' -hydroxyisopentyl or 2 ' -hydroxypentyl;
the bacteria are: staphylococcus aureus (Staphylococcus aureus), erysipelothrix rhusiopathiae (Erysipelothrix) and/or Streptococcus suis (Streptococcus suis).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110675730.1A CN113912484B (en) | 2021-06-18 | 2021-06-18 | 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound and application thereof in preparation of bacteriostat |
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| CN202110675730.1A CN113912484B (en) | 2021-06-18 | 2021-06-18 | 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound and application thereof in preparation of bacteriostat |
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| CN113912484B CN113912484B (en) | 2024-01-26 |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0769872A (en) * | 1993-09-02 | 1995-03-14 | Gifu Seratsuku Seizosho:Kk | Anti-methicilin resistant staphylococcus agent |
| KR20070065456A (en) * | 2005-06-13 | 2007-06-25 | 재단법인서울대학교산학협력재단 | Antibacterial compositions comprising extracts from genus tabebuia |
| CN102603525A (en) * | 2012-01-05 | 2012-07-25 | 中国海洋大学 | Anthraquinone derivative, as well as preparation method and application of anthraquinone derivative serving as antibacterial agent |
| CN104306364A (en) * | 2014-09-24 | 2015-01-28 | 李艳华 | Use of rheum officinale monomer in preparation of medicines for inhibiting Streptococcus suis or intervening Streptococcus suis biofilm |
| CN108003002A (en) * | 2017-11-27 | 2018-05-08 | 浙江工商大学 | Rheum emodin type anthraquinone Hedyanthraquinone A and its preparation method and application |
| CN109320409A (en) * | 2018-11-13 | 2019-02-12 | 河南中医药大学 | A kind of preparation method and applications with antimycotic and anti-tumor activity anthraquinone dimer class compound |
| CN111548954A (en) * | 2020-04-23 | 2020-08-18 | 安徽农业大学 | Four anthraquinone compounds and preparation method and application thereof |
-
2021
- 2021-06-18 CN CN202110675730.1A patent/CN113912484B/en active Active
Patent Citations (7)
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|---|---|---|---|---|
| JPH0769872A (en) * | 1993-09-02 | 1995-03-14 | Gifu Seratsuku Seizosho:Kk | Anti-methicilin resistant staphylococcus agent |
| KR20070065456A (en) * | 2005-06-13 | 2007-06-25 | 재단법인서울대학교산학협력재단 | Antibacterial compositions comprising extracts from genus tabebuia |
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| CN108003002A (en) * | 2017-11-27 | 2018-05-08 | 浙江工商大学 | Rheum emodin type anthraquinone Hedyanthraquinone A and its preparation method and application |
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Non-Patent Citations (4)
| Title |
|---|
| WU ZHAOYUAN等: "New Cytotoxic Alkylated Anthraquinone Analogues from a Soil Actinomycete Streptomyces sp. WS-13394", 《CHEMICAL AND PHARMACEUTICAL BULLETIN》, vol. 62, no. 1, pages 118 - 121 * |
| ZHAOYUAN WU等: "Four new anthraquinones from a soil actinomycete Streptomyces sp. WS-13394 and their bioactivities", 《NATURAL PRODUCT RESEARCH》, vol. 32, no. 4, pages 412 - 417 * |
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