Iriomoteolides-10a and 12a, Cytotoxic Macrolides from Marine Dinoflagellate Amphidinium Species

Chem Pharm Bull (Tokyo). 2016;64(7):1019-23. doi: 10.1248/cpb.c16-00026.

Abstract

Two new macrolides, iriomoteolides-10a (1) and -12a (2), have been isolated from a marine dinoflagellate Amphidinium sp. (KCA09053 strain), and their structures were elucidated on the basis of a detailed two dimensional (2D)-NMR analysis. Compound 1 is a novel 21-membered Amphidinium macrolide, which contains one tetrahydrofuran ring, two ketone carbonyls, two hydroxyl groups, and six one-carbon branches. Compound 2 is a new 12-membered macrolide related to amphidinolide Q. Compound 1 exhibited cytotoxic activity against human cervix adenocarcinoma HeLa and murine hepatocellular carcinoma MH134 cells.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dinoflagellida / chemistry*
  • Dose-Response Relationship, Drug
  • HeLa Cells
  • Humans
  • Macrolides / chemistry
  • Macrolides / isolation & purification
  • Macrolides / pharmacology*
  • Mice
  • Molecular Conformation
  • Structure-Activity Relationship

Substances

  • Macrolides
  • iriomoteolide-10a
  • iriomoteolide-12a