title: Nitropyrrolins A-E, cytotoxic farnesyl-α-nitropyrroles from a marine-derived bacterium within the actinomycete family Streptomycetaceae.
abstract: 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).
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California at San Diego, La Jolla, CA 92093-0204, USA.
authors.forename: Hak Cheol
authors.initials: HC
authors.lastname: Kwon
authors.forename: Ana Paula D M
authors.initials: AP
authors.lastname: Espindola
authors.forename: Jin-Soo
authors.initials: JS
authors.lastname: Park
authors.forename: Alejandra
authors.initials: A
authors.lastname: Prieto-Davó
authors.forename: Mickea
authors.initials: M
authors.lastname: Rose
authors.forename: Paul R
authors.initials: PR
authors.lastname: Jensen
authors.forename: William
authors.initials: W
authors.lastname: Fenical
mesh_terms: D039903:Actinobacteria / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D006801:Humans; D008386:Marine Biology; D016106:Methicillin Resistance / Q000187:drug effects; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D009574:Nitro Compounds; D011758:Pyrroles; D013729:Terpenes