Three phragmalin-type limonoids orthoesters and the structure of odoratone isolated from the bark of Entandrophragma candollei (Meliaceae)
(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.
(Less)
- author
- publishing date
- 2021-01
- 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}}, }