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We report the isolation and characterization of three new nybomycins (nybomycins B-D, 1 - 3 ) and six known compounds (nybomycin, 4 ; deoxynyboquinone, 5 ; α-rubromycin, 6 ; β-rubromycin, 7 ; γ-rubromycin, 8 ; and [2α(1 E ,3 E ),4β]-2-(1,3-pentadienyl)-4-piperidinol, 9 ) from the Rock Creek (McCreary County, KY) underground coal mine acid reclamation site isolate Streptomyces sp. AD-3-6. Nybomycin D ( 3 ) and deoxynyboquinone ( 5 ) displayed moderate ( 3 ) to potent ( 5 ) cancer cell line cytotoxicity and displayed weak to moderate anti-Gram-(+) bacterial activity, whereas rubromycins 6 - 8 displayed little to no cancer cell line cytotoxicity but moderate to potent anti-Gram-(+) bacterial and antifungal activity. Assessment of the impact of 3 or 5 cancer cell line treatment on 4E-BP1 phosphorylation, a predictive marker of ROS-mediated control of cap-dependent translation, also revealed deoxynyboquinone ( 5 )-mediated downstream inhibition of 4E-BP1p. Evaluation of 1 - 9 in a recently established axolotl embryo tail regeneration assay also highlighted the prototypical telomerase inhibitor γ-rubromycin ( 8 ) as a new inhibitor of tail regeneration. Cumulatively, this work highlights an alternative nybomycin production strain, a small set of new nybomycin metabolites, and previously unknown functions of rubromycins (antifungal activity and inhibition of tail regeneration) and also provides a basis for revision of the previously proposed nybomycin biosynthetic pathway.

journal of natural products

Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated <i>Streptomyces</i>

Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated Streptomyces