New malyngamides from the Hawaiian cyanobacterium Lyngbya majuscula

J Nat Prod. 2000 Dec;63(12):1599-602. doi: 10.1021/np000250t.

Abstract

Isomalyngamides A and B (1, 2) were isolated and characterized from a collection of the cyanobacterium Lyngbya majuscula from Hawaiian waters. These compounds represent a new type of malyngamide, similar to malyngamides Q and R, in which the conformation of the chloromethylene group is opposite from the majority of previously reported malyngamides. The geometry of the chloromethylene moiety was elucidated from the long-range coupling constants ((3)J(C)(-)(H)) obtained from editing-HETLOC and phase-sensitive HMBC experiments. Isomalyngamides A and B (1, 2) showed lethal toxicity to crayfish.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amides / isolation & purification*
  • Amides / toxicity
  • Animals
  • Astacoidea
  • Cyanobacteria / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification*
  • Pyrroles / toxicity

Substances

  • Amides
  • Pyrroles
  • isomalyngamide A
  • isomalyngamide B