Park, Kyoung JinMaier, SarahZhang, ChengqianDixon, Shelley A. H.Rusch, Douglas B.Pupo, Monica T.Angus, Steven P.Gerdt, Joseph P.2024-10-092024-10-092023Park KJ, Maier S, Zhang C, et al. Ravidomycin Analogs from Streptomyces sp. Exhibit Altered Antimicrobial and Cytotoxic Selectivity. J Nat Prod. 2023;86(8):1968-1979. doi:10.1021/acs.jnatprod.3c00381https://hdl.handle.net/1805/43837Six 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 (10-13) of 9 were also isolated. The structures were elucidated by combined spectroscopic and computational methods. We also found an inconsistency with the published [α]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.en-USPublisher PolicyAminoglycosidesAnti-bacterial agentsAntineoplastic agentsMolecular structureStreptomycesArticle