Constituents of the Leaves and Stem Bark of Aglaia foveolata.

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 (IC(50) range = 1.4-1.8 muM), and is the first member of the cyclopenta[b]benzopyran class found to exhibit this type of activity. Compound 2 also showed significant NF-kappaB inhibitory activity in an Elisa assay (IC(50) = 0.37 muM).

• Authors: Angela A Salim, Hee-Byung Chai, Ismail Rachman, Soedarsono Riswan, Leonardus B S Kardono, Norman R Farnsworth, Esperanza J Carcache-Blanco, A Douglas Kinghorn
• Journal: Tetrahedron (Tetrahedron) Vol. 63 Issue 33 Pg. 7926-7934 (Aug 13 2007) ISSN: 0040-4020 [Print] England
• PMID: 18698338 (Publication Type: Journal Article)