Malyngamide H, an ichthyotoxic amide possessing a new carbon skeleton from the Caribbean cyanobacterium Lyngbya majuscula

J Nat Prod. 1995 May;58(5):764-8. doi: 10.1021/np50119a019.

Abstract

Guided by ichthyotoxic activity against goldfish, a new lipopeptide, malyngamide H [1], and its corresponding free acid, 7-methoxytetradec-4(E)-enoic acid [2], have been isolated from the tropical marine cyanobacterium Lyngbya majuscula. The structure of the new carbon skeleton borne by malyngamide H was elucidated on the basis of spectroscopic analysis, mainly 2D nmr. The absolute stereochemistry of the cyclohexenone moiety of malyngamide H [1] was deduced by a combination of 2D NOESY and exciton chirality circular dichroism spectroscopy.

Publication types

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

MeSH terms

  • Animals
  • Chromatography, Ion Exchange
  • Circular Dichroism
  • Cyanobacteria / chemistry*
  • Cyclohexanones / chemistry*
  • Cyclohexanones / isolation & purification
  • Cyclohexanones / toxicity
  • Fatty Acids, Monounsaturated / chemistry*
  • Fatty Acids, Monounsaturated / isolation & purification
  • Fatty Acids, Monounsaturated / toxicity
  • Goldfish
  • Magnetic Resonance Spectroscopy
  • Stereoisomerism
  • Toxins, Biological / chemistry*
  • Toxins, Biological / isolation & purification
  • Toxins, Biological / toxicity

Substances

  • Cyclohexanones
  • Fatty Acids, Monounsaturated
  • Toxins, Biological
  • malyngamide H