Prenylated Acetophenone Derivatives from the Leaves of Acronychia pedunculata and Their Anti-Proliferative Activities

Chem Biodivers. 2024 Nov;21(11):e202401027. doi: 10.1002/cbdv.202401027. Epub 2024 Sep 13.

Abstract

Four new prenylated acetophenone derivatives, including one acetophenone dimer [acronyrone D (1)] and three acetophenone monomers [acronyrones E-G (2-4)], along with seven known analogues (5-11) were obtained from the leaves of Acronychia pedunculata. Their structures and absolute configurations were established by analysis of HRMS and NMR data, single crystal X-ray diffraction studies and quantum chemical calculations. In addition, the isolates were tested for their anti-proliferative acivity against HCT-116, RKO and SW480 cancer cell lines. Compound 5 exhibited significant anti-proliferative effects on the three cell lines, with IC50 values ranging from 0.24-5.3 μM.

Keywords: Rutaceae Acronychia pedunculata Prenylated acetophenone Anti-proliferative activities.

MeSH terms

  • Acetophenones* / chemistry
  • Acetophenones* / isolation & purification
  • Acetophenones* / pharmacology
  • Antineoplastic Agents, Phytogenic* / chemistry
  • Antineoplastic Agents, Phytogenic* / isolation & purification
  • Antineoplastic Agents, Phytogenic* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation* / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor*
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Plant Leaves* / chemistry
  • Prenylation
  • Rutaceae / chemistry
  • Structure-Activity Relationship

Substances

  • Acetophenones
  • Antineoplastic Agents, Phytogenic
  • acetophenone