An efficient synthesis of the Alpinia officinarum-derived diarylheptanoids, viz., enantiomers of a β-hydroxyketone ( 1 ) and an α, β-unsaturated ketone (2) was developed starting from commercially available eugenol.  Among these, compound 2    showed a superior antiproliferative effect against human breast adenocarcinoma MCF-7 cells. Besides reducing clonogenic   cell survival, compound 2 dose-dependently increased the sub G1 cell population and arrested the G2-phase of the cell  cycle, as revealed by flow cytometry. Mechanistically, compound 2 acts as an intracellular pro-oxidant by generating copious  amounts of reactive oxygen species.  Compound 2 also induced both loss of mitochondrial membrane potential (MMP) as  well as lysosomal membrane permeabilization (LMP) in the MCF-7 cells. The impaired mitochondrial and lysosomal functions  due to reactive oxygen species (ROS)-generation by compound 2 may contribute to its apoptotic property.