1´-S-1´-Acetoxychavicol Acetate

1'-(S)-1'-Acetoxychavicol acetate (galangal acetate) displays a wide variety of beneficial properties, including antioxidative, anti-obesity, antibacterial, anti-parasitic, chemopreventative, and chemotherapeutic activities. This compound is best known for its ability to inhibit xanthine oxidase, but also activates transient receptor potential cation channel A1 (TRPA1), an ion channel involved in pain and cold signaling. In vitro, 1'-(S)-1'-Acetoxychavicol acetate decreases GPDH activity and downregulates PPARgamma, C/EBPalpha, and phosphorylated AMPK, inhibiting adipogenesis. Additionally, 1'-(S)-1'-Acetoxychavicol acetate decreases visceral fat mass in animal models. 1'-(S)-1'-Acetoxychavicol acetate displays activity against both gram negative and gram positive bacteria in vitro and anti-parasitic activity against Leishmania donovani. In vitro, 1'-(S)-1'-Acetoxychavicol acetate displays chemopreventive activity, inhibiting development of azoxymethane-induced colon carcinogenesis. In vivo, this compound upregulates Nrf2 and induces expression of glutathione and NADPH quinone oxidoreductase 1. 1'-(S)-1'-Acetoxychavicol acetate also increases caspase-3 activity, inducing apoptosis and cell death in cellular models of glioblastoma and oral carcinoma. SMILES: CC(=O)OC1=CC=C(C=C1)C(C=C)OC(=O)C