Does nature provide the best therapeutic options? Synthesis and anti-inflammatory activity of a naturally occurring homoisoflavanone and its enantiomer

The Hyacinthaceae family is one of the most important plant families across the eastern seaboard of Africa. The (R)-5 enantiomer of a homoisoflavanone with anti-inflammatory activity was previously isolated from members of this family, namely Drimiopsis burkei Bak. and Scilla nervosa (Burch.) Jessop. However, the activity of the (S)-5 enantiomer is unknown. In this paper, we report the synthesis and structural elucidation, in vivo anti-inflammatory activity and in vitro cytotoxic properties of both the (R)-5 and (S)-5 enantiomers and the racemate. The enantiomers and racemate exhibited a relatively short duration of action and activity similar to that of the known non-steroidal anti-inflammatory drug, diclofenac. The naturally occurring enantiomer exhibited the least cytotoxicity.