Isolation, Synthesis, and Biological Activity of Chlorinated Alkylresorcinols from Dictyostelium Cellular Slime Molds

J Nat Prod. 2017 Oct 27;80(10):2716-2722. doi: 10.1021/acs.jnatprod.7b00456. Epub 2017 Sep 18.

Abstract

Eight chlorinated alkylresorcinols, monochasiol A-H (1-8), were isolated from the fruiting bodies of Dictyostelium monochasioides. Compounds 1-8 were synthesized to confirm their structures and to obtain sufficient material for performing biological tests. Monochasiol A (1) selectively inhibited the concanavalin A-induced interleukin-2 production in Jurkat cells, a human T lymphocyte cell line. Monochasiols were biogenetically synthesized by the combination of biosynthetic enzymes relating to the principal polyketides, MPBD and DIF-1, produced by Dictyostelium discoideum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Survival / drug effects
  • Concanavalin A / pharmacology
  • Dictyosteliida / chemistry
  • Dictyostelium / chemistry*
  • HeLa Cells
  • Hexanones / metabolism
  • Humans
  • Hydrocarbons, Chlorinated* / chemistry
  • Hydrocarbons, Chlorinated* / isolation & purification
  • Hydrocarbons, Chlorinated* / pharmacology
  • Interleukin-2 / biosynthesis
  • Jurkat Cells
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyketides / metabolism
  • Resorcinols* / chemistry
  • Resorcinols* / isolation & purification
  • Resorcinols* / pharmacology

Substances

  • Hexanones
  • Hydrocarbons, Chlorinated
  • Interleukin-2
  • Polyketides
  • Resorcinols
  • monochasiol A
  • Concanavalin A
  • 1-((3,5-dichloro)-2,6-dihydroxy-4-methoxyphenyl)-1-hexanone