Structure and relative potency of several karlotoxins from Karlodinium veneficum

J Nat Prod. 2010 Aug 27;73(8):1360-5. doi: 10.1021/np100158r.

Abstract

The karlotoxins are a family of amphidinol-like compounds that play roles in avoiding predation and in prey capture for the toxic dinoflagellate Karlodinium veneficum. The first member of the toxin group to be reported was KmTx 1 (1), and here we report an additional five new members of this family (3-7) from the same strain. Of these additional compounds, KmTx 3 (3) differs from KmTx 1 (1) in having one less methylene group in the saturated portion of its lipophilic arm. In addition, 64-E-chloro-KmTx 3 (4) and 10-O-sulfo-KmTx 3 (5) were identified. Likewise, 65-E-chloro-KmTx 1 (6) and 10-O-sulfo-KmTx 1 (7) were also isolated. Comparison of the hemolytic activities of the newly isolated compounds to that of KmTx 1 shows that potency correlates positively with the length of the lipophilic arm and is disrupted by sulfonation of the polyol arm.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Dinoflagellida / chemistry*
  • Erythrocytes / drug effects
  • Hemolytic Agents / chemistry
  • Hemolytic Agents / isolation & purification*
  • Hemolytic Agents / pharmacology*
  • Humans
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology*
  • Marine Toxins / chemistry
  • Marine Toxins / isolation & purification*
  • Marine Toxins / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyenes / chemistry
  • Polyenes / isolation & purification*
  • Polyenes / pharmacology*
  • Polyketides
  • Pyrans / chemistry
  • Pyrans / isolation & purification*
  • Pyrans / pharmacology*

Substances

  • Hemolytic Agents
  • Macrolides
  • Marine Toxins
  • Polyenes
  • Polyketides
  • Pyrans
  • karlotoxin 1
  • karlotoxin 3