Aerucyclamides A and B: isolation and synthesis of toxic ribosomal heterocyclic peptides from the cyanobacterium Microcystis aeruginosa PCC 7806

Cyril Portmann; Judith F Blom; Karl Gademann; Friedrich Jüttner

doi:10.1021/np800118g

Aerucyclamides A and B: isolation and synthesis of toxic ribosomal heterocyclic peptides from the cyanobacterium Microcystis aeruginosa PCC 7806

J Nat Prod. 2008 Jul;71(7):1193-6. doi: 10.1021/np800118g. Epub 2008 Jun 18.

Authors

Cyril Portmann¹, Judith F Blom, Karl Gademann, Friedrich Jüttner

Affiliation

¹ Chemical Synthesis Laboratory, SB-ISIC-LSYNC, Swiss Federal Institute of Technology, EPFL, CH-1015 Lausanne, Switzerland.

PMID: 18558743
DOI: 10.1021/np800118g

Abstract

Two new modified hexacyclopeptides, aerucyclamides A and B, were isolated from the toxic freshwater cyanobacterium Microcystis aeruginosa PCC 7806. The constitution was assigned by spectroscopic methods, and the configuration determined by chemical degradation and analysis by Marfey's method combined with chemical synthesis. Synthetic aerucyclamide B was obtained through oxidation of aerucyclamide A (MnO2, benzene). The aerucyclamides were found to be toxic to the freshwater crustacean Thamnocephalus platyurus, exhibiting LC50 values for congeners A and B of 30.5 and 33.8 microM, respectively.

MeSH terms

Animals
Crustacea / drug effects*
Fresh Water / microbiology
Microcystis / chemistry*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peptides, Cyclic* / chemical synthesis
Peptides, Cyclic* / chemistry
Peptides, Cyclic* / isolation & purification
Peptides, Cyclic* / toxicity

Substances

Peptides, Cyclic
aerucyclamide A
aerucyclamide B