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

Happi, Gervais Mouthé ; Mouthe Kemayou, Guy Paulin ; Stammler, Hans Georg ; Neumann, Beate ; Ismail, Mohamed LU orcid ; Kouam, Simeon Fogue ; Wansi, Jean Duplex ; Tchouankeu, Jean Claude ; Frese, Marcel and Lenta, Bruno Ndjakou , et al. (2021) In Phytochemistry 181.
Abstract

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)... (More)

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 IC50 of 1.47 μM compared to the reference griseofulvin (IC50 = 17–21 μM). The results of the in silico docking of compound 4 supported and delivered further insights on its cytotoxicity.

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publishing date
type
Contribution to journal
publication status
published
keywords
Cytotoxicity, Encandollens C-E, Entandrophragma candollei, In silico docking, Meliaceae, Phragmalin-class limonoid
in
Phytochemistry
volume
181
article number
112537
publisher
Elsevier
external identifiers
  • pmid:33099226
  • scopus:85093648861
ISSN
0031-9422
DOI
10.1016/j.phytochem.2020.112537
language
English
LU publication?
no
id
09f1be5a-3c9c-4c81-b20d-96a9b56bf0e8
date added to LUP
2023-08-28 11:50:39
date last changed
2024-04-20 02:03:14
@article{09f1be5a-3c9c-4c81-b20d-96a9b56bf0e8,
  abstract     = {{<p>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<sub>50</sub> of 1.47 μM compared to the reference griseofulvin (IC<sub>50</sub> = 17–21 μM). The results of the in silico docking of compound 4 supported and delivered further insights on its cytotoxicity.</p>}},
  author       = {{Happi, Gervais Mouthé and Mouthe Kemayou, Guy Paulin and Stammler, Hans Georg and Neumann, Beate and Ismail, Mohamed and Kouam, Simeon Fogue and Wansi, Jean Duplex and Tchouankeu, Jean Claude and Frese, Marcel and Lenta, Bruno Ndjakou and Sewald, Norbert}},
  issn         = {{0031-9422}},
  keywords     = {{Cytotoxicity; Encandollens C-E; Entandrophragma candollei; In silico docking; Meliaceae; Phragmalin-class limonoid}},
  language     = {{eng}},
  publisher    = {{Elsevier}},
  series       = {{Phytochemistry}},
  title        = {{Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of <i>Entandrophragma candollei</i> (Meliaceae)}},
  url          = {{http://dx.doi.org/10.1016/j.phytochem.2020.112537}},
  doi          = {{10.1016/j.phytochem.2020.112537}},
  volume       = {{181}},
  year         = {{2021}},
}