Rhodozepinone, a new antitrypanosomal azepino-diindole alkaloid from the marine sponge-derived bacterium Rhodococcus sp. UA13
A new azepino-diindole alkaloid; rhodozepinone (1), along with five known compounds, including 2-amino-3-[2(1H)-quinolinon-4-yl]propionic acid (2), 3-hydroxy-2-methyl-4H-pyran-4-one (maltol) (3), phenyl acetic acid methyl ester (4), indole-3-acetic acid (5), and 2-amino-3-(1H-indol-3-yl) propanoic acid (tryptophan) (6) were isolated and identified from the broth culture of Rhodococcus sp. UA13, which had been previously recovered from the Red Sea sponge Callyspongia aff. Implexa. The structures of compounds (1–6) were determined by spectroscopic analyses, including 1D and 2D NMR experiments in combination with HR-ESI-MS, as well as comparison with the literature. All the characterized metabolites were firstly reported herein from this marine sponge-associated actinomycete, and among them, (3), (4), and (6) were characterized for the first time from the genus Rhodococcus, whereas this is the first report for isolation of compound (2) from a natural source. Moreover, both the antimicrobial and antitrypanosomal properties of the isolated metabolites (1–6) were evaluated, and only rhodozepinone (1) exhibited significant antibacterial and antitrypanosomal activities against Staphylococcus aureus NCTC 8325 (IC50 = 8.9 µg/ml) and Trypanosoma brucei brucei TC221 [IC50 = 16.3 (48 h) and 11.8 (72 h) µg/ml], respectively. These results totally reflected the potential of sponge-derived actinomycetes as a rich source of new natural products with interesting bioactivities, as well as their promising future contribution to drug discovery.
Publisher URL: https://link.springer.com/article/10.1007/s00044-017-1974-y
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