| Full text | |
| Author(s): |
Park, Kyoung Jin
;
Maier, Sarah
;
Zhang, Chengqian
;
Dixon, Shelley A. H.
;
Rusch, Douglas B.
;
Pupo, Monica T.
;
Angus, Steven P.
;
Gerdt, Joseph P.
Total Authors: 8
|
| Document type: | Journal article |
| Source: | Journal of Natural Products; v. N/A, p. 12-pg., 2023-08-02. |
| Abstract | |
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) | |
| FAPESP's process: | 13/50954-0 - Novel therapeutic agents from the bacterial symbionts of Brazilian invertebrates |
| Grantee: | Mônica Tallarico Pupo |
| Support Opportunities: | BIOTA-FAPESP Program - Thematic Grants |