Farnesyl-α-nitropyrroles from a marine-derived bacterium within the actinomycete family Streptomycetaceae

Farnesyl-α-nitropyrroles from a marine-derived bacterium within the actinomycete family Streptomycetaceae
권학철A.P D.M. Espondola박진수A. Prieto-DavoM RoseP. R. JensenW. Fenical
marine actinomycete; nitropyrrolin; α-nitropyrrole
Issue Date
The 13th International Symposium on Marine Natural Products
As part as our continuing interest in the chemistry and biomedical potential of sediment-derived marine actinomycetes, we have isolated a variety of new actinomycete taxa, which show the capacity to produce unique secondary metabolites. One of new marine-derived actinomycetes, designated the MAR 4 group, is proving to be of significant chemical interest. To date, at least 19 strains have been isolated from a diversity of marine sediments. previous chemical studies of cultured MAR 4 strains led to the discovery of polyketide-terpenoid secondary metabolites including marinone,^5 compounds of the napyradiomycin series^6 and azamerone.^7 Further chemical analysis of a cultured MAR4 strain (our strain # CNQ-509), isolated from a marine sediment sample collected in La Jolla, has also showm the production of polyketide-terpenoid metabolites, composed of sesquiterpenoid and α-nitropyrroles components. The structures of these compounds, nitropyrrolins A-E 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 full stereostructures and absolute configurations of these compounds. Several of the nitropyrrolins, nitropyrrolin D in particular, are cutotoxic toward HT-116 human colon carcinoma cells, but show weak to little antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA).
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