Accramycin A, a New Aromatic Polyketide, from the Soil Bacterium, Streptomyces sp. MA37
| Autor: | Valentin Leman, Qing Fang, Kwaku Kyeremeh, Rainer Ebel, Hai Deng, Sylvia Soldatou, Fleurdeliz Maglangit |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Group B Streptococcus
Stereochemistry Pharmaceutical Science 010402 general chemistry 01 natural sciences Streptomyces Analytical Chemistry lcsh:QD241-441 Polyketide Minimum inhibitory concentration chemistry.chemical_compound Biosynthesis lcsh:Organic chemistry Drug Discovery naphthacene Streptomyces sp. MA37 Physical and Theoretical Chemistry Natural product biology 010405 organic chemistry Drug discovery Chemistry Organic Chemistry accramycin biology.organism_classification 0104 chemical sciences type II polyketide Chemistry (miscellaneous) Molecular Medicine Pharmacophore Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Molecules Volume 24 Issue 18 Molecules, Vol 24, Iss 18, p 3384 (2019) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules24183384 |
| Popis: | Drug-like molecules are known to contain many different building blocks with great potential as pharmacophores for drug discovery. The continued search for unique scaffolds in our laboratory led to the isolation of a novel Ghanaian soil bacterium, Streptomyces sp. MA37. This strain produces many bioactive molecules, most of which belong to carbazoles, pyrrolizidines, and fluorinated metabolites. Further probing of the metabolites of MA37 has led to the discovery of a new naphthacene-type aromatic natural product, which we have named accramycin A 1. This molecule was isolated using an HPLC-photodiode array (PDA) guided isolation process and MS/MS molecular networking. The structure of 1 was characterized by detailed analysis of LC-MS, UV, 1D, and 2D NMR data. Preliminary studies on the antibacterial properties of 1 using Group B Streptococcus (GBS) produced a minimum inhibitory concentration (MIC) of 27 µ g/mL. This represents the first report of such bioactivity amongst the naphthacene-type aromatic polyketides, and also suggests the possibility for the further development of potent molecules against GBS based on the accramycin scaffold. A putative acc biosynthetic pathway for accramycin, featuring a tridecaketide-specific type II polyketide synthase, was proposed. |
| Databáze: | OpenAIRE |
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