Coumarins from Creston apple seeds: Isolation, chemical modification, and cytotoxicity study

Abstract

In the present work, preliminary phytochemical screening tests were performed on extracts of Creston apple seeds. Extraction was performed using two methods, which are serial Soxhlet extraction and kinetic maceration utilizing water, methanol, chloroform, and n-hexane as extraction solvents. Three coumarin derivatives acquired from chloroform extract in the order of increasing polarity were isolated via column chromatography and one of them was chemically modified by esterification, Fries rearrangement, and methylation afforded three semisynthetic derivatives. Detection of physicochemical properties and analysis of FTIR, 1H-NMR and 13C-NMR spectra of the natural and semisynthetic coumarins were used to identify their structures. In vitro cytotoxic activity of the aforementioned coumarin derivatives was studied on three cancer cell lines, which are MCF-7, AMN3, and HeLa using MTT assay. The results indicated that compounds N3, S4, S5 and S6 have IC50 values lower than that of 5- fluorouracil against MCF-7 cell line and all compounds have higher IC50 values than that of 5-fluorouracil against AMN3 and HeLa cell lines.