Amphidinolides H2-H5, G2, and G3, new cytotoxic 26- and 27-membered macrolides from dinoflagellate Amphidinium sp

J Org Chem. 2002 Sep 20;67(19):6585-92. doi: 10.1021/jo016222c.

Abstract

Six new macrolides, amphidinolides H2 (5), H3 (6), H4 (7), H5 (8), G2 (9), and G3 (10), have been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42). Cytotoxicity of five derivatives (11-15) of amphidinolide H (1) in addition to 10 amphidinolides (1-10) containing amphidinolides H (1), G (2), B (3), and D (4) was examined, and it was found that the presence of an allyl epoxide, an S-cis-diene moiety, and the ketone at C-20 was important for the cytotoxicity of amphidinolide H (1)-type macrolides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Survival / drug effects
  • Dinoflagellida / chemistry*
  • Drug Screening Assays, Antitumor
  • Humans
  • Japan
  • KB Cells / drug effects
  • Leukemia
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Marine Toxins / chemistry
  • Marine Toxins / isolation & purification*
  • Marine Toxins / pharmacology
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured / drug effects

Substances

  • Macrolides
  • Marine Toxins
  • amphidinolide H