A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens

Mar Drugs. 2014 May 12;12(5):2748-59. doi: 10.3390/md12052748.

Abstract

Lyngbyatoxin A from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) is known as the causative agent of "swimmer's itch" with its highly inflammatory effect. A new toxic compound was isolated along with lyngbyatoxin A from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies revealed the isolated compound had the same planar structure with that of lyngbyatoxin A. The results of optical rotation and CD spectra indicated that the compound was a new lyngbyatoxin A derivative, 12-epi-lyngbyatoxin A (1). While 12-epi-lyngbyatoxin A showed comparable toxicities with lyngbyatoxin A in cytotoxicity and crustacean lethality tests, it showed more than 100 times lower affinity for protein kinase Cδ (PKCδ) using the PKCδ-C1B peptide when compared to lyngbyatoxin A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / pharmacology
  • Cyanobacteria / chemistry*
  • Hawaii
  • Humans
  • Lethal Dose 50
  • Leukemia L1210 / drug therapy
  • Lyngbya Toxins / chemistry*
  • Lyngbya Toxins / pharmacology*
  • Lyngbya Toxins / toxicity
  • Molecular Conformation
  • Palaemonidae
  • Protein Kinase C / antagonists & inhibitors
  • Protein Kinase C / metabolism

Substances

  • 12-epi-lyngbyatoxin A
  • Antineoplastic Agents
  • Lyngbya Toxins
  • Protein Kinase C