Antimalarial ceramicines Q-T from Chisocheton ceramicus

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 determ...

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Autores principales: Nugroho, Alfarius Eko, Wong, Chin Piow, Hirasawa, Yusuke, Kaneda, Toshio, Tougan, Takahiro, Horii, Toshihiro, Hadi, A. Hamid A., Morita, Hiroshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Nature Singapore 2023
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10171166/
https://www.ncbi.nlm.nih.gov/pubmed/37162697
http://dx.doi.org/10.1007/s11418-023-01706-w
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author Nugroho, Alfarius Eko
Wong, Chin Piow
Hirasawa, Yusuke
Kaneda, Toshio
Tougan, Takahiro
Horii, Toshihiro
Hadi, A. Hamid A.
Morita, Hiroshi
author_facet Nugroho, Alfarius Eko
Wong, Chin Piow
Hirasawa, Yusuke
Kaneda, Toshio
Tougan, Takahiro
Horii, Toshihiro
Hadi, A. Hamid A.
Morita, Hiroshi
author_sort Nugroho, Alfarius Eko
collection PubMed
description 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 (13)C 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 IC(50) value of 2.8 µM. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11418-023-01706-w.
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spelling pubmed-101711662023-05-11 Antimalarial ceramicines Q-T from Chisocheton ceramicus Nugroho, Alfarius Eko Wong, Chin Piow Hirasawa, Yusuke Kaneda, Toshio Tougan, Takahiro Horii, Toshihiro Hadi, A. Hamid A. Morita, Hiroshi J Nat Med Original Paper 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 (13)C 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 IC(50) value of 2.8 µM. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11418-023-01706-w. Springer Nature Singapore 2023-05-10 2023 /pmc/articles/PMC10171166/ /pubmed/37162697 http://dx.doi.org/10.1007/s11418-023-01706-w Text en © The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.
spellingShingle Original Paper
Nugroho, Alfarius Eko
Wong, Chin Piow
Hirasawa, Yusuke
Kaneda, Toshio
Tougan, Takahiro
Horii, Toshihiro
Hadi, A. Hamid A.
Morita, Hiroshi
Antimalarial ceramicines Q-T from Chisocheton ceramicus
title Antimalarial ceramicines Q-T from Chisocheton ceramicus
title_full Antimalarial ceramicines Q-T from Chisocheton ceramicus
title_fullStr Antimalarial ceramicines Q-T from Chisocheton ceramicus
title_full_unstemmed Antimalarial ceramicines Q-T from Chisocheton ceramicus
title_short Antimalarial ceramicines Q-T from Chisocheton ceramicus
title_sort antimalarial ceramicines q-t from chisocheton ceramicus
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10171166/
https://www.ncbi.nlm.nih.gov/pubmed/37162697
http://dx.doi.org/10.1007/s11418-023-01706-w
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