Hypersonins A-D, Polycyclic Polyprenylated Acylphloroglucinols with a 1,2- seco-Homoadamantane Architecture from Hypericum wilsonii

J Nat Prod. 2020 Jun 26;83(6):1804-1809. doi: 10.1021/acs.jnatprod.9b01187. Epub 2020 Jun 16.

Abstract

Hypersonins A-D (1-4), four 1,2-seco-homoadamantane type polycyclic polyprenylated acylphloroglucinols (PPAPs) possessing a new bicyclo[4.3.1]decane-3-methoxycarbonyl architecture, were obtained from Hypericum wilsonii. The structures of hypersonins A-D were identified by spectroscopic data, electronic circular dichroism comparison, and X-ray crystallographic data. Hypersonins A-D are the first seco-homoadamantane-type PPAPs with cleavage at the C-1-C-2 bond. Hypersonin A (1) showed moderate inhibitory activity to anti-CD3/anti-CD28 monoclonal antibody-induced proliferation of murine splenocytes, with an IC50 value of 8.3 ± 0.2 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antibodies, Blocking
  • Antineoplastic Agents, Phytogenic / chemistry
  • CD28 Antigens / antagonists & inhibitors
  • CD3 Complex / antagonists & inhibitors
  • Cell Proliferation / drug effects
  • Circular Dichroism
  • Hypericum / chemistry*
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Molecular Structure
  • Polycyclic Compounds / chemistry
  • Polycyclic Compounds / pharmacology*
  • Spleen / cytology
  • X-Ray Diffraction

Substances

  • Antibodies, Blocking
  • Antineoplastic Agents, Phytogenic
  • CD28 Antigens
  • CD3 Complex
  • Polycyclic Compounds