Members of the Annonaceae have the particularity to elaborate a broad spectrum of natural products that display anti-bacterial, antifungal, and anti-protozoal effects and have been used for treating skin diseases, intestinal worms, inflammation of the eyes, HIV, and cancer. These pharmacological aspects and the variety of secondary metabolites make the Annonaceae unique from other similar families in the Magnoliales and the Angiosperms in general. As part of our research interest on the discovery of novel constituents from Philippine endemic Annonaceae species, we hereby present the structure identification of two unusual C-benzylated chalcone-derived b-triketones � uvarenol A (1 ) and uvarenol B (2 ) and a novel cyclopentenone benzylated ester, valdemarrenone (3 ) from a new Philippines Annonaceae species, Uvaria valderramensis sp. nov. The isolation of 1 -3  entails extraction of the ground dried leaf samples with DCM-MeOH (1:1), fractionation by polarity and a series of silica gel column chromatography. Their structures were established from UV, IR, MS and NMR spectroscopic data. The relative stereochemistry of 1  and 2  was assigned through 2D NOESY, CD-ORD and X-ray experiments. The biogenetic origin of these metabolites is also proposed. Antimycobacterial susceptibility testing of uvarenol A (1 ) and valdemarrenone (3 ) using the colorimetric MABA assay show moderate to strong inhibitory activity against Mycobacterium tuberculosis H37Rv (MIC = 10 mg/mL for 1 ; 32 mg/mL for 3 ). Compounds 1  and 3  also demonstrated promising anti-proliferative activity against Hela, leukemia and HUVEC cell lines.

Discovery of new antituberculosis and anticancer aromatic metabolites from the new Philippine Annonaceae species, <i>Uvaria valderramensis</i>

245th National Meeting (2013)

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Discovery of new antituberculosis and anticancer aromatic metabolites from the new Philippine Annonaceae species, Uvaria valderramensis