Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure-Activity Relationships

J Nat Prod. 2017 Nov 22;80(11):2883-2888. doi: 10.1021/acs.jnatprod.7b00345. Epub 2017 Nov 9.

Abstract

Amphidinols are polyketide metabolites produced by marine dinoflagellates and are chiefly composed of a long linear chain with polyol groups and polyolefins. Two new homologues, amphidinols 20 (AM20, 1) and 21 (AM21, 2), were isolated from Amphidinium carterae collected in Korea. Their structures were elucidated by detailed NMR analyses as amphidinol 6-type compounds with remarkably long polyol chains. Amphidinol 21 (2) has the longest linear structure among the amphidinol homologues reported so far. The congeners, particularly amphidinol 21 (2), showed weaker activity in hemolysis and antifungal assays compared to known amphidinols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Animals
  • Antifungal Agents / pharmacology
  • Dinoflagellida / chemistry*
  • Drugs, Chinese Herbal / chemistry*
  • Hemolysis
  • Japan
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyketides / chemistry*
  • Polyketides / isolation & purification*
  • Pyrans / chemistry
  • Structure-Activity Relationship

Substances

  • Alkenes
  • Antifungal Agents
  • Drugs, Chinese Herbal
  • Polyketides
  • Pyrans