Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae).

Autor: Happi GM; Department of Chemistry, Higher Teacher Training College, University of Bamenda, P.O Box 39, Bambili, Cameroon; Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany; Department of Chemistry, Higher Teacher Training College, University of Yaounde I, P. O. Box 47, Yaounde, Cameroon. Electronic address: gervais20022003@yahoo.fr., Mouthe Kemayou GP; Department of Chemistry, Higher Teacher Training College, University of Yaounde I, P. O. Box 47, Yaounde, Cameroon., Stammler HG; Inorganic and Structural Chemistry, Department of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany., Neumann B; Inorganic and Structural Chemistry, Department of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany., Ismail M; Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany; Department of Microbiology, Faculty of Science, Helwan University, Ain Helwan, 11795, Cairo, Egypt., Kouam SF; Department of Chemistry, Higher Teacher Training College, University of Yaounde I, P. O. Box 47, Yaounde, Cameroon., Wansi JD; Department of Chemistry, University of Douala, Faculty of Sciences, 24157, Douala, Cameroon., Tchouankeu JC; Department of Organic Chemistry, Faculty of Sciences, University of Yaounde I, 812, Yaounde, Cameroon., Frese M; Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany., Lenta BN; Department of Chemistry, Higher Teacher Training College, University of Yaounde I, P. O. Box 47, Yaounde, Cameroon., Sewald N; Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany.
Jazyk: angličtina
Zdroj: Phytochemistry [Phytochemistry] 2021 Jan; Vol. 181, pp. 112537. Date of Electronic Publication: 2020 Oct 21.
DOI: 10.1016/j.phytochem.2020.112537
Abstrakt: The phytochemical exploration of the Entandrophragma candollei stem bark extract led to the isolation and identification of twenty compounds including three undescribed phragmalin-class limonoids named encandollens C-E (1-3), the undescribed protolimonoid 5 together with sixteen known compounds. The structures of all the isolated compounds were determined by interpretation of their spectroscopic and spectrometric data including HRMS, 1D and 2D NMR analyses. The assignment of the absolute and relative stereochemistry of the undescribed compounds was achieved using SC-XRD analyses as well as NOESY experiments. The previously reported structure of odoratone (5a) was corrected as 23 R,24 S-dihydroxy-22 S,25-epoxytirucall-7-en-3-one (5) based on its NMR and SC-XRD data. Prieurianin (4) exhibited high cytotoxic activity on KB3-1 cell lines with an IC 50 of 1.47 μM compared to the reference griseofulvin (IC 50  = 17-21 μM). The results of the in silico docking of compound 4 supported and delivered further insights on its cytotoxicity.
(Copyright © 2020 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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