Polyketide 13 [=2-hydroxy-5-((6-hydroxy-4-oxo-4H-pyran-2-yl)methyl)-2-propylchroman-4-one] and three related known compounds 7, 9 and 11 were obtained and structurally characterized from Streptomyces sundarbansensis strain, an endophytic actinomycete isolated from the Algerian marine brown algae Fucus sp. Compound 13 was obtained as the major metabolite from optimized culture conditions, by using Agar state fermentation. Due to tautomeric equilibrium, Compound 13 in CD3OD solution was able to incorporate five deuterium atoms, as deduced by NMR and ESI-MS/MS analysis. The 2-hydroxy-γ-pyrone form was established for these metabolites based on the comparison of their experimental IR spectra with the DFT calculated ones, for both the corresponding 4-hydroxy-α-pyrone and 2-hydroxy-γ- pyrone forms. During antibacterial evaluation, compound 13 stood out as the most active of the series, showing a selective activity against the Gram positive pathogenic methicillin-resistant S. aureus (MRSA, MIC = 6 μΜ), with a bacteriostatic effect.
Scheda prodotto non validato
I dati visualizzati non sono stati ancora sottoposti a validazione formale da parte dello Staff di IRIS, ma sono stati ugualmente trasmessi al Sito Docente Cineca (Loginmiur).
|Titolo:||Antibacterial polyketide from the marine alga-derived endophitic Streptomyces sundarbansensis: a study on hydroxypyrone tautomerism|
|Autori:||Mouloud, Kecha; Ibtissem, Djinni; Defant, Andrea; Mancini, Ines|
|Autore/i del libro:||Eureka conference inc|
|Titolo del volume contenente il saggio:||Drug discovery and Therapy world congress 2015 : Abstracts|
|Luogo di edizione:||Boston, MA USA|
|Casa editrice:||Euroconference Inc|
|Anno di pubblicazione:||2015|
|Appare nelle tipologie:||04.2 Abstract in atti di convegno (Abstract in Proceedings)|