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Application of 3,4,8,9,10-pentahydroxyl dibenzotriazole[b,d]pyran-6-actone in preparing antibacterial drug

A technology of pentahydroxydiphenyl and antibacterial drugs, which is applied in the field of natural medicinal chemistry and pharmaceutical applications, and can solve the problem that there is no report on the material basis of drug effects

Active Publication Date: 2018-08-24
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As a medicinal plant, Terminalia citrina (Gaertn) Roxb is widely used in Myanmar to treat gastrointestinal discomfort and dysentery, but there is no report on the pharmacodynamic material basis of its action

Method used

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  • Application of 3,4,8,9,10-pentahydroxyl dibenzotriazole[b,d]pyran-6-actone in preparing antibacterial drug
  • Application of 3,4,8,9,10-pentahydroxyl dibenzotriazole[b,d]pyran-6-actone in preparing antibacterial drug
  • Application of 3,4,8,9,10-pentahydroxyl dibenzotriazole[b,d]pyran-6-actone in preparing antibacterial drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1. Separation of Compound 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one

[0025] Compound 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one is isolated from the ripe fruit of Myrobalan, and the separation method is as follows:

[0026] (1) Weigh 1.0 kg of myrobalan, soak and extract three times at room temperature with a mixed solvent of ethyl acetate and methanol at a volume ratio of 4:1, combine the extracts, and concentrate to dryness at 40 ° C under reduced pressure to obtain a crude extract;

[0027] (2) The crude extract was dissolved in water, extracted and degreased with petroleum ether multiple times; the aqueous phase was extracted with ethyl acetate multiple times, and the organic phase was concentrated to dryness at 40°C under reduced pressure to obtain 22.0 g of EA extract;

[0028] (3) The EA extract was firstly separated by 180g reversed-phase C18 silica gel column chromatography, and eluted with water, 30%, 50%, 70%, and 100% methanol in sequence, ...

Embodiment 2

[0029] Example 2. Structural identification of compound 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one

[0030] The quasi-molecular ion peak of the compound measured by ESI-MS is m / z 277.03[M+H] + . 1 H and 13 C NMR shows that the compound structure contains a total of 13 carbon atoms (see Table 1), including 3 sp 2 Hybrid olefinic carbon (δ H / δ C 7.39 / 108.9d, 6.78 / 113.2d, 8.46 / 119.9d, 10 sp 2 Hybridized quaternary carbon (δ C 112.8s, 119.3s, 133.6s, 134.1s, 141.8s, 144.8s, 147.6s, 147.2s, 142.7s, 164.6s). A set of mutually coupled proton signals δ H 6.78 (d, 9.04), and 8.46 (d, 9.04) indicate that there is a 1,2,3,4-tetrasubstituted benzene ring structure in the compound, according to HMBC (H-1 [8.46 (d, 9.04)] and C-10a, C-1a, C-4a, C-3, H-2[δ H 6.78(d,9.04)] Long-range correlation with C-4, C-1a, C-4, C-3, determined the structure of some fragments. According to the singlet proton H-7[(δ H 7.39 (s)] and the long-range correlation of C-6a, C-10a, C-8, C-9, C...

Embodiment 3

[0034] Example 3. Compound 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one in vitro on Salmonella type III secretion system toxic protein secretion SipA, B, C and D inhibition

[0035] (See literature Hudson DL, et.al.Antimicrobial Agents Chemotherapy, 2007,51:2631-2635 and Li JF, et al.Antimicrobial Agents and Chemotherapy 2013,57(5):2191-2198)

[0036] Test principle: The type III secretion system is a very important virulence factor in the pathogenic process of Gram-negative bacteria. It uses the type III secretion system to secrete toxic proteins to promote the invasion of host cells and the propagation and diffusion in host cells . Therefore, blocking the secretion of toxic proteins can inhibit the invasion of host cells by Gram-negative pathogens. In this experiment, Salmonella typhimurium UK-1 (χ8956) was used as the research object. Through the method of temperature induction, Salmonella typhimurium was induced to secrete toxic proteins into the cultured bacterial liq...

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Abstract

The invention relates to an application of a compound 3,4,8,9,10-pentahydroxyl dibenzotriazole[b,d]pyran-6-actone in preparing an antibacterial drug. The compound is firstly separated from mature fruits of Burma terminalia citrina (Gaertin) Roxb. According to the experiment, the compound has relatively good inhibition effect on secretion of toxic proteins SipA, B, C and D of salmonella T3SS, doesnot have inhibition effect on growth of salmonella, and inhibits invasion, on HeLa cells, of salmonella by inhibiting transfer of toxic proteins. Therefore, the compound 3,4,8,9,10-pentahydroxyl dibenzotriazole[b,d]pyran-6-actone can be used for preparing the antibacterial drug, especially can be used for preparing a gram-negative pathogenic drug.

Description

technical field [0001] The present invention relates to the application of a novel bacterial virulence factor inhibitor, in particular to the application of compound 3,4,8,9,10-pentahydroxydibenzo[b,d]pyran-6-one in the preparation of antibacterial drugs The invention belongs to the technical field of natural medicine chemistry and medicine application. Background technique [0002] At present, with the widespread use of antibiotics, the drug resistance of pathogenic bacteria has gradually become a major issue facing human beings. The continuous emergence of multi-drug resistant bacteria also makes people face the same problems as the era of lack of antibiotics. Therefore, finding new drugs that inhibit bacterial virulence factors has become an urgent problem to be solved. Among the multidrug-resistant bacteria, most of them are opportunistic pathogens, among which Gram-negative bacilli account for a large proportion, such as Escherichia coli, Shigella, Salmonella, and Pseu...

Claims

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Application Information

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IPC IPC(8): A61K31/37A61K45/06A61P31/04C07D311/80
CPCA61K31/37A61K45/06A61P31/04C07D311/80Y02A50/30
Inventor 鲁春华沈月毛李天红
Owner SHANDONG UNIV
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