Continuing studies on the cyanobacterium Lyngbya sp.: isolation and structure determination of 15-norlyngbyapeptin A and lyngbyabellin D

J Nat Prod. 2003 May;66(5):595-8. doi: 10.1021/np030011g.

Abstract

Re-collections of the cyanobacterium Lyngbya sp. have yielded two more members of the lyngbyapeptin and lyngbyabellin families. The gross structures of 15-norlyngbyapeptin A (1) and lyngbyabellin D (3) were deduced through standard 2D NMR techniques, with the absolute configuration of both elucidated through degradation and comparison with commercially available and synthetic standards. Degradation to the alpha-amino acid and NOE correlations determined the absolute and relative configuration of the 4-amino-3-hydroxy-5-methylhexanoic acid unit in 3. Lyngbyabellin D (3) displayed an IC(50) value of 0.1 microM against the KB cell line.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cyanobacteria / chemistry*
  • Drug Screening Assays, Antitumor
  • Guam
  • Humans
  • Inhibitory Concentration 50
  • KB Cells
  • Lyngbya Toxins / chemistry
  • Lyngbya Toxins / isolation & purification*
  • Lyngbya Toxins / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Thiazoles / chemistry
  • Thiazoles / isolation & purification*
  • Thiazoles / pharmacology

Substances

  • 15-norlyngbyapeptin A
  • Antineoplastic Agents
  • Lyngbya Toxins
  • Thiazoles
  • lyngbyabellin D