%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 (1−5), 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