Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium

J Nat Prod. 2016 Jul 22;79(7):1862-6. doi: 10.1021/acs.jnatprod.6b00171. Epub 2016 Jun 30.

Abstract

Janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Cyanobacteria / chemistry*
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology
  • Polyketides / chemistry
  • Polyketides / isolation & purification*
  • Polyketides / pharmacology
  • Trypanosoma / drug effects*
  • Trypanosoma brucei brucei / drug effects

Substances

  • Peptides, Cyclic
  • Polyketides
  • janadolide