Ulongapeptin, a cytotoxic cyclic depsipeptide from a Palauan marine cyanobacterium Lyngbya sp

J Nat Prod. 2003 May;66(5):651-4. doi: 10.1021/np030050s.

Abstract

Ulongapeptin (1), a cyclic depsipeptide, was isolated from a Palauan marine cyanobacterium Lyngbya sp. The gross structure was elucidated through one-dimensional TOCSY experiments and other spectroscopic techniques. The absolute and relative stereochemistry of the beta-amino acid, 3-amino-2-methyl-7-octynoic acid (AMO), in 1 was determined by synthesis of the saturated alpha-alkyl-beta-amino acid and Marfey's analysis of the acid hydrolysate of tetrahydro-1. Ulongapeptin (1) was cytotoxic against KB cells at an IC(50) value of 0.63 microM.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cyanobacteria / chemistry*
  • Depsipeptides*
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • KB Cells / drug effects
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Palau
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology
  • Stereoisomerism
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Depsipeptides
  • Peptides, Cyclic
  • ulongapeptin