Ravidomycin Analogs from Streptomyces sp. Exhibit Altered Antimicrobial and Cytotoxic Selectivity

Autor(es)

Park, Kyoung Jin ; Maier, Sarah ; Zhang, Chengqian ; Dixon, Shelley A. H. ; Rusch, Douglas B. ; Pupo, Monica T. ; Angus, Steven P. ; Gerdt, Joseph P.

• Tipo de documento: Artigo Científico
• Fonte: Journal of Natural Products; v. N/A, p. 12-pg., 2023-08-02.

Resumo

Six new ravidomycin analogs (1-4, 6, and 7) were isolated from Streptomyces sp. Am59 using UV- and LCMS-guided separation based on Global Natural Products Social (GNPS) molecular networking analysis. Furthermore, we isolated fucomycin V (9), which possesses the same chromophore as ravidomycin but features a D-fucopyranose instead of D-ravidosamine. This is the first report of 9 as a natural product. Four new analogs (1013) of 9 were also isolated. The structures were elucidated by combined spectroscopic and computational methods. We also found an inconsistency with the published [a] D25 of deacetylravidomycin, which is reported to have a (-) sign. Instead, we observed a (+) specific rotation for the reported absolute configuration of deacetylravidomycin (containing D-ravidosamine). We confirmed the positive sign by reisolating deacetylravidomycin from S. ravidus and by deacetylating ravidomycin. Finally, antibacterial, antifungal, and cytotoxicity activities were determined for the compounds. Compared to deacetylravidomycin, the compounds 4-6, 9, 11, and 12 exhibited greater antibacterial selectivity. (AU)

• Processo FAPESP: 13/50954-0 - Novos agentes terapêuticos obtidos de bactérias simbiontes de invertebrados brasileiros
• Beneficiário: Mônica Tallarico Pupo
• Modalidade de apoio: Auxílio à Pesquisa - Programa BIOTA - Temático