Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery.

ABSTRACT: The heronapyrroles A-C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A-C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists

SUBMITTER: Schmidt J 

PROVIDER: S-EPMC4077399 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature