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Medermycin compounds as well as preparation method and application thereof

A technology for metamycin and its compounds, which is applied in the field of metamycin compounds and their preparation, can solve the problems of high toxicity, no specificity of metamycin, and the inability to make medicines, etc., and achieve good kinase inhibition and inhibition The effect of growth

Active Publication Date: 2018-12-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] It has been more than 40 years since the discovery of Metamycin, but studies have found that Metamycin has no specificity. It not only acts on tumor cells, but also affects the proliferation and division of normal cells. undruggable

Method used

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  • Medermycin compounds as well as preparation method and application thereof
  • Medermycin compounds as well as preparation method and application thereof
  • Medermycin compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] 1. Fermentation of compounds

[0053] 1) Take an appropriate amount of actinomycetes from the original storage slant or glycerol tube, inoculate it on the solid medium of Gaoshi No. 1 plate, let it stand in an incubator at 28°C, and activate it for 4 days.

[0054] 2) Inoculate the single colony of actinomycetes activated in step 1) into a 500mL Erlenmeyer flask containing 250mL liquid medium, each bottle containing 250mL Gaoshi No. 1 liquid medium, in a shaker at 28°C Shake culture at 180rpm for 8 days to obtain fermentation broth.

[0055] 2. Preparation of compounds

[0056] (a) The fermentation broth was extracted three times with an equal volume of ethyl acetate, and the obtained extract was dried in vacuo to remove the ethyl acetate solvent. The obtained ethyl acetate fraction was subjected to silica gel column chromatography, and the dichloromethane-methanol system with a volume ratio of 100:1 to 0:1 was used for gradient elution. Fractions containing new compo...

Embodiment 2

[0065] The obtaining of fermented liquid is the same as in Example 1, the only difference is that in the preparation step (c) of the compound, the fractions containing the new compound are separated by reverse phase high performance liquid chromatography (Agilent Pursuit C-18 (10 μm, 21.2 × 250mm ) chromatographic column, the detection wavelength is 230nm, the mobile phase used is a methanol-water system with a methanol volume ratio of 10 to 100% containing 0.05% trifluoroacetic acid, and is eluted with a gradient of 20mL / min for 40 minutes, and the elution of 10 to 12 minutes is collected. The structure of the compound obtained by separation and purification was identified, and the molecular formula was calculated as C 25 h 32 NO 10 ([M+H] + m / z 506.2020), further based on nuclear magnetic resonance data, its specific structure is as follows, denoted as strepoxepinmycin B:

[0066]

[0067] The NMR data for this compound are listed in Table 2 below.

[0068] Table 2

...

Embodiment 3

[0072] The obtaining of fermented liquid is the same as in Example 1, the only difference is that in the preparation step (c) of the compound, the fractions containing the new compound are separated by reverse phase high performance liquid chromatography (Agilent Pursuit C-18 (10 μm, 21.2 × 250mm ) chromatographic column, the detection wavelength is 254nm, the mobile phase used is a methanol-water system with a methanol volume ratio of 10 to 100% containing 0.05% trifluoroacetic acid, and is eluted with a gradient of 20mL / min for 40 minutes, and the elution of 15 to 17 minutes is collected. The structure of the compound obtained by separation and purification was identified, and the molecular formula was calculated as C 25 h 34 NO 10 ([M+H] + m / z 508.2179), further based on nuclear magnetic resonance data, its specific structure is as follows, denoted as strepoxepinmycin C:

[0073]

[0074] The NMR data for this compound are listed in Table 3 below.

[0075] table 3

...

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Abstract

The invention discloses medermycin compounds. Structural formulas are as shown in the formula (I) to (IV) as shown in the description respectively. The medermycin compounds of novel structures are allnatural products obtained after actinomycetes are subjected to fermentation culture and purification, and the variety of medermycin analogues is greatly increased. (The formulas are shown in the description).

Description

technical field [0001] The invention relates to the field of preparing active compounds from secondary metabolites of actinomycetes, in particular to a class of metamycin compounds and their preparation methods and applications. Background technique [0002] Medermycin (medermycin, whose structural formula is as follows (1)) is an aromatic polyketide antibiotic belonging to the pyranoquinone family. It was first isolated from Streptomyces K73 by Japanese researchers in 1976. Studies have shown that metamycin has a good activity inhibitory effect on the overexpressed AKT kinase in some cancer cells. As a key component in the signaling pathway of tumor cells, AKT kinase has become an important target for anticancer drug screening; Daxamycin is also active against many Gram-positive bacteria, including staphylococci. Therefore, metamycin has potential anticancer and antibacterial effects. [0003] It has been more than 40 years since the discovery of Metamycin, but studies ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/14C07D493/04C07D311/92C12P17/18C12P17/06A61P35/00A61P31/04A61P35/02A61P31/18A61P25/28C12R1/465
CPCA61P25/28A61P31/04A61P31/18A61P35/00A61P35/02C07D311/92C07D493/04C07D493/14C12P17/06C12P17/181
Inventor 马忠俊蒋永俊丁婉婧李嘉琪
Owner ZHEJIANG UNIV
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