Bioassay-Guided Fractionation and Dereplication Studies of Sesame oil: Isolation of 8-Acetoxypinoresinol as an Anti-Proliferative Metabolite and Prediction of Target

Abstract

Sesamum indicum is a plant cultivated mainly in South Asia. It is rich in lignans and dietary fatty acids. The lignans of furofuran class are reported to display many pharmacological activities; therefore, the source of dietary sesame oil was used as biological material for investigation. Bioassay-guided fractionation followed by Liquid Chromatography-Mass Spectroscopy and Dictionary of Natural Products based dereplication strategy led to the identification and isolation of a tetrahydrofurofuran lignan. The pure compound was isolated by regular column and High performance liquid chromatography and it was characterized as 8-acetoxypinoresinol based on 2D NMR (Nuclear Magnetic Resonance). Hitherto, this compound has not been isolated from genus Sesamum; hence, this is first report of isolation of 8-acetoxypinoresinol from sesame oil. 2D NMR established the complete structure including relative configuration and compound was found to be cytotoxic with IC50: 9, 14, 18, 17, 22 µg/mL on HL-60, MCF-7, MIA-PaCa2, PC-3 and A549, respectively. It further displayed anti-cancer activity with Matrix mettaloproteases loss and induced DNA content cell cycle arrest. Further, computational studies helped to predict JNK 1 as probable pharmacological target. This study supports medicinal value of the sesame seed oil. © 2022, The National Academy of Sciences, India.