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Ceramicines U-Z from Chisocheton ceramicus and structure-antimalarial activity relationship study.

Alfarius Eko Nugroho1, Tomoyuki Komuro1, Takuya Kawaguchi1

  • 1Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-Ku, Tokyo, 142-8501, Japan.

Journal of Natural Medicines
|September 10, 2023
PubMed
Summary
This summary is machine-generated.

Six new limonoids, ceramicines U-Z, were isolated from Malaysian Chisocheton ceramicus. Ceramicine W demonstrated potent antimalarial activity, with structure-activity relationships highlighting key features for enhanced efficacy.

Keywords:
Antimalarial activityCeramicines U–ZChisocheton ceramicusLimonoidsMeliaceaeStructure–antimalarial activity relationship

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Area of Science:

  • Natural Product Chemistry
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Ceramicines, a class of limonoids from Chisocheton ceramicus, possess known biological activities.
  • The Malaysian plant Chisocheton ceramicus is a source of diverse limonoid compounds.

Purpose of the Study:

  • To isolate and characterize new ceramicine limonoids from Chisocheton ceramicus barks.
  • To evaluate the antimalarial activity of novel ceramicines against Plasmodium falciparum.
  • To investigate the structure-activity relationships (SAR) of ceramicines for antimalarial efficacy.

Main Methods:

  • Isolation and purification of limonoids using chromatographic techniques.
  • Structure elucidation of new compounds via 1D and 2D Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Determination of absolute configurations using Circular Dichroism (CD) spectroscopy.
  • In vitro antimalarial activity assay against Plasmodium falciparum (3D7 strain).

Main Results:

  • Six new limonoids, ceramicines U-Z (1-6), were identified, featuring a cyclopentanone[α]phenanthrene ring system with a β-furyl moiety.
  • Ceramicine W (3) exhibited significant antimalarial activity with an IC50 value of 1.2 µM against Plasmodium falciparum 3D7.
  • Structure-activity relationship analysis indicated that the B ring and adjacent functional groups are crucial for antimalarial potency.
  • Bulky, equatorially oriented ester substituents at C-7 and C-12 positions were found to substantially enhance antimalarial activity.

Conclusions:

  • The study successfully identified novel ceramicine limonoids with potent antimalarial properties.
  • Ceramicine W represents a promising lead compound for further antimalarial drug development.
  • Understanding the SAR of ceramicines provides valuable insights for designing more effective antimalarial agents targeting Plasmodium falciparum.