Ulleunganilines A-C, Trichostatin Analogues Bearing a Modified Side Chain from Streptomyces sp. 13F051

J Nat Prod. 2021 Sep 24;84(9):2420-2426. doi: 10.1021/acs.jnatprod.1c00324. Epub 2021 Aug 28.

Abstract

Three new trichostatin analogues, ulleunganilines A-C (1-3), and seven known trichostatins (4-10) were isolated from cultures of Streptomyces sp. 13F051. NMR, UV, and MS data indicated that the planar structures of 1-3 consisted of modified side chains in the trichostatic acid moiety. The absolute configuration of the 2,4-dimethyl-branched carbon chains in 1 and 2 was determined by the PGME method, while the amino acid group in 3 was identified by advanced Marfey's method. Based on the structure of the modified side chains, the origin of 1-3 is proposed. Further experiments indicated that 1 and 3 displayed moderate histone deacetylase inhibitory activity, suggesting that not only the hydroxamate group but also the N,N-dimethyl group were essential for the inhibitory activity.

MeSH terms

  • Cell Line, Tumor
  • Histone Deacetylase Inhibitors / isolation & purification
  • Histone Deacetylase Inhibitors / pharmacology*
  • Humans
  • Hydroxamic Acids / isolation & purification
  • Hydroxamic Acids / pharmacology*
  • Molecular Structure
  • Republic of Korea
  • Soil Microbiology
  • Streptomyces / chemistry

Substances

  • Histone Deacetylase Inhibitors
  • Hydroxamic Acids