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Antimalarial ceramicines Q-T from Chisocheton ceramicus.

Alfarius Eko Nugroho¹, Chin Piow Wong¹, Yusuke Hirasawa²

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

Journal of Natural Medicines

|May 10, 2023

Summary

Four new limonoids, ceramicines Q-T, were identified from Malaysian Chisocheton ceramicus bark. Ceramicine R demonstrated significant antimalarial activity against Plasmodium falciparum.

Keywords:

Antimalarial activity Ceramicines Q–T Chisocheton ceramicus Limonoids Meliaceae

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Area of Science:

Natural Product Chemistry
Medicinal Chemistry
Pharmacology

Background:

Ceramicines are known limonoids with diverse biological activities.
These compounds are derived from the Malaysian plant Chisocheton ceramicus.
Previous studies have indicated various bioactivities of ceramicines.

Purpose of the Study:

To isolate and characterize new limonoids from Chisocheton ceramicus.
To investigate the structural features of these novel compounds.
To evaluate the biological activity, specifically antimalarial potential, of the isolated limonoids.

Main Methods:

Isolation of compounds from C. ceramicus bark.
Structure elucidation using 1D and 2D Nuclear Magnetic Resonance (NMR) analyses.
Comparison with calculated ¹³C chemical shift data for structural confirmation.

Main Results:

Four new limonoids, ceramicines Q-T (1-4), were successfully isolated.
Structures were determined, revealing a unique cyclopentanone[α]phenanthren ring system with a β-furyl ring at C-17.
Notably, these new compounds lack the tetrahydrofuran ring present in known ceramicines.
Ceramicine R (2) exhibited potent antimalarial activity against Plasmodium falciparum 3D7 with an IC₅₀ of 2.8 µM.

Conclusions:

Ceramicines Q-T represent a novel series of limonoids with distinct structural characteristics.
The findings expand the chemical diversity of ceramicines.
Ceramicine R shows promising antimalarial potential, warranting further investigation.