Heronamides A - C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp. A biosynthetic case for synchronized tandem electrocyclization

Ritesh Raju, Andrew M. Piggott, Melissa M. Conte, Robert J. Capon

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4682-4689
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number20
DOIs
Publication statusPublished - 21 Oct 2010
Externally publishedYes

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