Heronamides A-C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp. A biosynthetic case
Ritesh Raju1, Andrew M Piggott, Melissa M Conte
1Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Queensland, Australia4072.
Abstract:
A Streptomyces sp. isolated from a shallow water sediment sample collected off Heron Island, Australia, afforded three new polyketide macrolactams, heronamides A-C (1-3). Structures were assigned to the heronamides on the basis of detailed spectroscopic analysis, chemical derivatization and biosynthetic considerations. A plausible biosynthetic pathway is proposed in which key carbocyclic ring transformations proceed via an unprecedented synchronized tandem electrocyclization. This biosynthesis provides a framework for the assignment of complete relative configurations across all heronamides, and inspires an attractive biomimetic strategy for future total syntheses. Heronamide C elicits a dramatic and reversible non-cytotoxic effect on mammalian cell morphology.
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