A new α-pyrone from Arthrinium pseudosinense culture medium and its estrogenic activity in MCF-7 cells

J Antibiot (Tokyo). 2021 Dec;74(12):893-897. doi: 10.1038/s41429-021-00473-8. Epub 2021 Sep 8.

Abstract

A new α-pyrone analog, arthrifuranone A (1) was isolated from an EtOAc-extract of Arthrinium pseudosinense culture medium. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The chemical structure of the new compound was elucidated using MS and NMR spectroscopic techniques, and the absolute configuration was established by the Mosher's method and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + analysis. The isolated compound was evaluated for its estrogenic activity using the MCF-7 estrogen responsive human breast cancer cells. Compound 1 showed estrogenic activity by increasing the proliferation of MCF-7 cells at the concentration of 3.125 μM via phosphorylation of estrogen receptor-α.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascomycota / metabolism*
  • Breast Neoplasms / metabolism
  • Cell Proliferation / drug effects
  • Estrogen Receptor alpha / drug effects*
  • Estrogen Receptor alpha / metabolism
  • Estrogens / chemistry
  • Estrogens / isolation & purification
  • Estrogens / pharmacology*
  • Female
  • Humans
  • MCF-7 Cells
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Pyrones / chemistry
  • Pyrones / isolation & purification
  • Pyrones / pharmacology*

Substances

  • Estrogen Receptor alpha
  • Estrogens
  • Pyrones

Supplementary concepts

  • Arthrinium pseudosinense