Amphidinins C-F, amphidinolide Q analogues from marine dinoflagellate Amphidinium sp

Org Lett. 2014 Nov 7;16(21):5624-7. doi: 10.1021/ol502685z. Epub 2014 Oct 27.

Abstract

Four new polyketides, amphidinins C-F (1-4), have been isolated from the culture broth of symbiotic dinoflagellate Amphidinium sp. The analysis of their spectral data revealed that amphidinins C-F (1-4) were 4,5-seco-analogues of amphidinolide Q (5). The absolute configurations of the new compounds were elucidated by the combination of J-based configuration analysis, modified Mosher's method, and chemical derivatization. Amphidinins D (2) and F (4) are the first glycosides related to amphidinolides. Amphidinins C-F (1-4) showed antimicrobial activity against bacteria and/or fungi.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / isolation & purification
  • Anti-Infective Agents / pharmacology
  • Dinoflagellida / chemistry*
  • Dinoflagellida / isolation & purification
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Macrolides / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Marine Toxins / chemistry*
  • Marine Toxins / isolation & purification
  • Marine Toxins / pharmacology*
  • Molecular Structure
  • Polyketides / chemistry*
  • Polyketides / isolation & purification
  • Stereoisomerism

Substances

  • Anti-Infective Agents
  • Macrolides
  • Marine Toxins
  • Polyketides
  • amphidinolide Q