Dioleate and trioleate epoxides from palm oil as anticancer agents through in vitro and molecular docking studies

Dioleate and trioleate epoxides were successfully obtained from palm oil through several steps and evaluated as anticancer agent potential via in vitro assays and studies of their binding to the FASN protein. At first, fatty acid methyl esters (FAMEs) were isolated through the transesterification reaction from palm oil. Next, the methyl oleate from FAME was purified through urea inclusion method and then hydrolyzed into oleic acid. The oleic acid was further reacted with 1,2-propanediol and glycerol to produce 1,2-propanеdiol dioleate (dioleate) and glyceryl-1,2,3-trioleate (trioleate) derivatives, respectively. The dioleate and trioleate compounds were epoxidized with performic acid reagent to yield dioleate and trioleate epoxides, respectively. Trioleate epoxide generated a more potent anticancer activity against T47D and WiDr cancer cells with IC50 values of 27.40 and 32.41 mg L^{-1} , respectively. In comparison, the IC50 values of dioleate epoxide against T47D and WiDr cancer cells are 35.66 and 38.25 mg L^{-1} . Trioleate epoxide and dioleate epoxide were non-toxic for normal cells with selectivity index values of 9.19-10.87 and 7.60-8.16, respectively. The molecular docking showed that dioleate and trioleate epoxides could inhibit the function of the FASN enzyme with binding affinity values of -27.11 and -27.61 kJ mol^{-1} , respectively.