Constituents of the leaves and stem bark of Aglaia foveolata

Salim, Angela A., Chai, Hee-Byung, Rachman, Ismail, Riswan, Soedarsono, Kardono, Leonardus B.S., Farnsworth, Norman R., Carcache-Blanco, Esperanza J. and Kinghorn, A. Douglas (2007) Constituents of the leaves and stem bark of Aglaia foveolata. Tetrahedron, 63 33: 7926-7934. doi:10.1016/j.tet.2007.05.074


Author Salim, Angela A.
Chai, Hee-Byung
Rachman, Ismail
Riswan, Soedarsono
Kardono, Leonardus B.S.
Farnsworth, Norman R.
Carcache-Blanco, Esperanza J.
Kinghorn, A. Douglas
Title Constituents of the leaves and stem bark of Aglaia foveolata
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
Publication date 2007-08-13
Year available 2007
Sub-type Article (original research)
DOI 10.1016/j.tet.2007.05.074
Volume 63
Issue 33
Start page 7926
End page 7934
Total pages 9
Place of publication Oxford
Publisher Pergamon Press
Language eng
Subject 030401 Biologically Active Molecules
030502 Natural Products Chemistry
Abstract The previously known potent cytotoxic agent silvestrol (1) (0.002% w/w yield) and five new flavagline derivatives (2–6) were isolated from the leaves of Aglaia foveolata collected in Indonesia. The new compound 5 has an unprecedented cyclic amide moiety in its cyclopenta[b]benzopyran skeleton, while compound 6 is a novel benzo[b]oxepine derivative in which the oxepine ring is cleaved. Pyramidatine (7), a biogenetic precursor of the new flavaglines 2–6, was isolated from the leaf extract investigated. Silvestrol was also isolated from the stem bark of A. foveolata (yield of 0.02% w/w) along with a new baccharane-type triterpenoid (8). The structures of the new compounds were elucidated on the basis of their NMR and mass spectrometric data. All new compounds isolated were tested against a panel of cancer cell lines, but only compound 2 was cytotoxic (IC50 range=1.4–1.8 μM), and is the first member of the cyclopenta[b]benzopyran class found to exhibit this type of activity. Compound 2 also showed significant NF-κB inhibitory activity in an Elisa assay (IC50=0.37 μM).
Q-Index Code C1

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
School of Biological Sciences Publications
 
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