%0 Journal Article %A Kwon, Hak Cheol %A Paula D. M. Espindola, Ana %A Park, Jin-Soo %A Prieto-Davó, Alejandra %A Rose, Mickea %A Jensen, Paul R. %A Fenical, William %D 2010 %T Nitropyrrolins A−E, Cytotoxic Farnesyl-α-nitropyrroles from a Marine-Derived Bacterium within the Actinomycete Family Streptomycetaceae %U https://acs.figshare.com/articles/journal_contribution/Nitropyrrolins_A_E_Cytotoxic_Farnesyl_nitropyrroles_from_a_Marine_Derived_Bacterium_within_the_Actinomycete_Family_i_Streptomycetaceae_i_/2702503 %R 10.1021/np1006229.s001 %2 https://acs.figshare.com/ndownloader/files/4378450 %K saline culture %K acetonide formation %K functionalized farnesyl groups %K MRSA %K HCT %K nitropyrrolin D %K Mosher method %K Actinomycete Family StreptomycetaceaeFive %K CNQ %K MAR %K compound %K strain %K colon carcinoma cells %K marine actinomycetes %X Five new farnesyl-α-nitropyrroles, nitropyrrolins A−E (15), were isolated from the saline culture of the marine actinomycete strain CNQ-509. This strain belongs to the “MAR4” group of marine actinomycetes, which have been demonstrated to be a rich source of hybrid isoprenoid secondary metabolites. The structures of the nitropyrrolins are composed of α-nitropyrroles with functionalized farnesyl groups at the C-4 position. These compounds are the first examples of naturally occurring terpenyl-α-nitropyrroles. Chemical modifications, including one-step acetonide formation from an epoxide, and application of the modified Mosher method provided the full stereostructures and absolute configurations of these compounds. Several of the nitropyrrolins, nitropyrrolin D in particular, are cytotoxic toward HCT-116 human colon carcinoma cells, but show weak to little antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). %I ACS Publications