Structure and Stereochemistry of Amphidinolide N Congeners from Marine Dinoflagellate Amphidinium Species

Chem Pharm Bull (Tokyo). 2021;69(1):141-149. doi: 10.1248/cpb.c20-00745.

Abstract

Two highly potent cytotoxic 26-membered macrolides, isocaribenolide-I (1) and a chlorohydrin 2, together with known amphidinolide N (3), have been isolated from a free-swimming dinoflagellate Amphidinium species (KCA09053 and KCA09056 strains) collected off Iriomote Island, Japan. The structures of 1 and 2 were determined to be a congener of 3 with an isobutyl terminus and the chlorohydrin form of 3, respectively, by detailed analyses of spectroscopic data. The relative stereochemistries of 1 and 2 were elucidated by the conformational analyses based on NMR data.

Keywords: Amphidinium; cytotoxic activity; dinoflagellate; macrolide.

MeSH terms

  • Cell Survival / drug effects
  • Dinoflagellida / chemistry*
  • Dose-Response Relationship, Drug
  • HeLa Cells
  • Humans
  • Macrolides / chemistry
  • Macrolides / isolation & purification
  • Macrolides / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Macrolides
  • amphidinolide N