Structures of Nahuoic Acids B-E Produced in Culture by a Streptomyces sp. Isolated from a Marine Sediment and Evidence for the Inhibition of the Histone Methyl Transferase SETD8 in Human Cancer Cells by Nahuoic Acid A

J Org Chem. 2016 Feb 19;81(4):1324-32. doi: 10.1021/acs.joc.5b02569. Epub 2016 Feb 1.

Abstract

Nahuoic acids A-E (1-5) have been isolated from laboratory cultures of a Streptomyces sp. obtained from a tropical marine sediment. The structures of the new polyketides 2-5 were elucidated by analysis of spectroscopic data of the natural products and the chemical derivatives 6 and 7. Nahuoic acids 1-5 are in vitro inhibitors of the histone methyltransferase SETD8, and nahuoic acid A (1) and its pentaacetate derivative 8 inhibit the proliferation of several cancer cells lines in vitro with modest potency. At the IC50 for cancer cell proliferation, nahuoic acid A (1) showed selective inhibition of SETD8 in U2OS osteosarcoma cells that reflect its selectivity against a panel of pure histone methyl transferases. A cell cycle analysis revealed that the cellular toxicity of nahuoic acid A (1) is likely linked to its ability to inhibit SETD8 activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Line
  • Cell Proliferation
  • Geologic Sediments
  • Histone Methyltransferases
  • Histone-Lysine N-Methyltransferase / antagonists & inhibitors*
  • Histone-Lysine N-Methyltransferase / chemistry
  • Histones / chemistry*
  • Humans
  • Molecular Structure
  • Polyketides / chemistry*
  • Polyketides / isolation & purification
  • Polyketides / pharmacology*
  • Streptomyces / chemistry*

Substances

  • Antineoplastic Agents
  • Histones
  • Polyketides
  • nahuoic acid A
  • Histone Methyltransferases
  • Histone-Lysine N-Methyltransferase