Longisglucinols A-C, Structurally Intriguing Polycyclic Polyprenylated Acylphloroglucinols with Anti-inflammatory Activity from Hypericum longistylum

Org Lett. 2020 Oct 16;22(20):7926-7929. doi: 10.1021/acs.orglett.0c02853. Epub 2020 Oct 1.

Abstract

Longisglucinol A (1), a polycyclic polyprenylated acylphloroglucinol (PPAP) with a new skeleton, along with two new congeners, longisglucinols B (2) and C (3), were isolated from Hypericum longistylum. Compound 1 features an unparalleled 6/6/6/5 fused ring skeleton based on a unique 8-oxa-tetracyclo-[8.3.3.01,9.03,7]cetane core. Longisglucinol A showed remarkable anti-inflammatory activity by inducing macrophage M2 polarization through the suppression of NF-κB.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Hypericum / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors*
  • NF-kappa B / chemistry
  • NF-kappa B / metabolism

Substances

  • Anti-Inflammatory Agents
  • NF-kappa B