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. 2023 Jun;77(3):596-603.
doi: 10.1007/s11418-023-01706-w. Epub 2023 May 10.

Antimalarial ceramicines Q-T from Chisocheton ceramicus

Alfarius Eko Nugroho  1 , Chin Piow Wong  1 , Yusuke Hirasawa  2 , Toshio Kaneda  1 , Takahiro Tougan  3 , Toshihiro Horii  4 , A Hamid A Hadi  5 , Hiroshi Morita  6
Affiliations

Antimalarial ceramicines Q-T from Chisocheton ceramicus

Alfarius Eko Nugroho et al. J Nat Med. 2023 Jun.

Abstract

Ceramicines are a series of limonoids that were isolated from the bark of Malaysian Chisocheton ceramicus (Meliaceae) and were known to show various biological activity. Four new limonoids, ceramicines Q-T (1-4) were isolated from the barks of C. ceramicus, and their structures were determined on the basis of the 1D and 2D NMR analyses in combination with calculated 13C chemical shift data. Ceramicines Q-T (1-4) were established to be new limonoids with a cyclopentanone[α]phenanthren ring system with a β-furyl ring at C-17, and without a tetrahydrofuran ring like ceramicine B, which is characteristic of known ceramicines. Ceramicine R (2) exhibited potent antimalarial activity against Plasmodium falciparum 3D7 strain with IC50 value of 2.8 µM.

Keywords: Antimalarial activity; Ceramicines Q–T; Chisocheton ceramicus; Limonoids; Meliaceae.

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Figures

Fig. 1
Fig. 1
Structures of 1–4
Fig. 2
Fig. 2
Selected 2D NMR correlations of 1
Fig. 3
Fig. 3
Selected 2D NMR correlations of 2
Fig. 4
Fig. 4
Structures of the lowest-energy conformation of the two possible isomers (2a and 2b) of ceramicine R (2)
Fig. 5
Fig. 5
Parts per million difference between the calculated 13C NMR shifts for the two possible isomers (2a and 2b) and the experimental data of ceramicine R (2)
See this image and copyright information in PMC

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