Synthesis of Bioactive Diarylheptanoids from Alpinia officinarum and Their Mechanism of Action for Anticancer Properties in Breast Cancer Cells

Synthesis of Bioactive Diarylheptanoids from Alpinia officinarum and Their Mechanism of Action for Anticancer Properties in Breast Cancer Cells

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...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2021-02, Vol.84 (2), p.352-363
Hauptverfasser: Gamre, Sunita, Tyagi, Mrityunjay, Chatterjee, Sucheta, Patro, Birija S, Chattopadhyay, Subrata, Goswami, Dibakar
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container_issue 2
container_start_page 352
container_title Journal of natural products (Washington, D.C.)
container_volume 84
creator Gamre, Sunita
Tyagi, Mrityunjay
Chatterjee, Sucheta
Patro, Birija S
Chattopadhyay, Subrata
Goswami, Dibakar
description 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.
doi_str_mv 10.1021/acs.jnatprod.0c01012
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title Synthesis of Bioactive Diarylheptanoids from Alpinia officinarum and Their Mechanism of Action for Anticancer Properties in Breast Cancer Cells
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