Cytotoxic polyprenylated phloroglucinol derivatives from Hypericum elodeoides Choisy modulating the transactivation of RXRα

Bioorg Chem. 2021 Feb:107:104578. doi: 10.1016/j.bioorg.2020.104578. Epub 2020 Dec 23.

Abstract

Hyperelodione D (1), an undescribed polyprenylated phloroglucinol derivative possessing 6/6/5/5 fused tetracyclic core, together with hyperelodiones E-F (2-3), two unreported analogues bearing 6/5/5 fused tricyclic structure, were isolated from Hypericum elodeoides Choisy. Their planar structures were elucidated by spectroscopic analysis (HRESIMS, 1D and 2D NMR) and their absolute configurations were determined by comparison of experimental and calculated ECD data. The cytotoxicity and retinoid X receptor-α (RXRα) related activities of the isolates were evaluated and the plausible biogenetic pathways of 1-3 were proposed.

Keywords: Cytotoxicity; Hypericum elodeoides Choisy; Phloroglucinol; Retinoid X receptor-α (RXRα).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line
  • Cell Survival / drug effects
  • Density Functional Theory
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Hypericum / chemistry*
  • Molecular Structure
  • Phloroglucinol / chemistry
  • Phloroglucinol / isolation & purification
  • Phloroglucinol / pharmacology*
  • Retinoid X Receptor alpha / antagonists & inhibitors*
  • Retinoid X Receptor alpha / metabolism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Retinoid X Receptor alpha
  • Phloroglucinol