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

Happi GM, Mouthe Kemayou GP, Stammler H-G, Neumann B, Ismail M, Kouam SF, Wansi JD, Tchouankeu JC, Frese M, Lenta BN, Sewald N (2020)
Phytochemistry 181: 112537.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Happi, Gervais Mouthe; Mouthe Kemayou, Guy Paulin; Stammler, Hans-GeorgUniBi; Neumann, BeateUniBi; Ismail, MohamedUniBi; Kouam, Simeon Fogue; Wansi, Jean Duplex; Tchouankeu, Jean Claude; Frese, MarcelUniBi ; Lenta, Bruno Ndjakou; Sewald, NorbertUniBi
Abstract / Bemerkung
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 23R,24S-dihydroxy-22S,25-epoxytirucall-7-en-3-one (5) based on its NMR and SC-XRD data. Prieurianin (4) exhibited high cytotoxic activity on KB3-1cell lines with an IC50 of 1.47muM compared to the reference griseofulvin (IC50=17-21muM). 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.
Erscheinungsjahr
2020
Zeitschriftentitel
Phytochemistry
Band
181
Art.-Nr.
112537
eISSN
1873-3700
Page URI
https://pub.uni-bielefeld.de/record/2948413

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Happi GM, Mouthe Kemayou GP, Stammler H-G, et al. Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae). Phytochemistry. 2020;181: 112537.
Happi, G. M., Mouthe Kemayou, G. P., Stammler, H. - G., Neumann, B., Ismail, M., Kouam, S. F., Wansi, J. D., et al. (2020). Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae). Phytochemistry, 181, 112537. doi:10.1016/j.phytochem.2020.112537
Happi, G. M., Mouthe Kemayou, G. P., Stammler, H. - G., Neumann, B., Ismail, M., Kouam, S. F., Wansi, J. D., Tchouankeu, J. C., Frese, M., Lenta, B. N., et al. (2020). Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae). Phytochemistry 181:112537.
Happi, G.M., et al., 2020. Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae). Phytochemistry, 181: 112537.
G.M. Happi, et al., “Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae)”, Phytochemistry, vol. 181, 2020, : 112537.
Happi, G.M., Mouthe Kemayou, G.P., Stammler, H.-G., Neumann, B., Ismail, M., Kouam, S.F., Wansi, J.D., Tchouankeu, J.C., Frese, M., Lenta, B.N., Sewald, N.: Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae). Phytochemistry. 181, : 112537 (2020).
Happi, Gervais Mouthe, Mouthe Kemayou, Guy Paulin, Stammler, Hans-Georg, Neumann, Beate, Ismail, Mohamed, Kouam, Simeon Fogue, Wansi, Jean Duplex, Tchouankeu, Jean Claude, Frese, Marcel, Lenta, Bruno Ndjakou, and Sewald, Norbert. “Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae)”. Phytochemistry 181 (2020): 112537.

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