Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl‑oxo‑biseugenol, a New Oxidized Derivative of Biseugenol

Electrochemical procedures have emerged as a powerful tool for the synthesis of complex organic molecules including transformation natural products. In this study, electrosynthesis biseugenol in MeOH afforded one new oxidized derivative, which was characterized methoxyloxo-biseugenol (MOB) by nuclear magnetic resonance (NMR) and electrospray ionization-high resolution mass spectrometry (ESI-HRMS) analysis. Since previously described cytotoxic product, MOB also tested against tumoral cells B16F10-Nex2 (murine metastatic melanoma) SKMEL-25 (human well nontumoral MØ Raw 264.7 macrophage immortalized) HUVEC umbilical endothelium). As results, showed inhibitory concentration that affects 50% (IC50)values 9.5 ± 1.6 mg mL-1 (B16F10Nex2), 13.2 2.5 (SKMEL-25), 19.9 3.5 (MØ 264.7) 36.3 7.4 (HUVEC). Therefore, selectivity index (SI) values to B16F10Nex2 were calculated 2.1 2.8, respectively, higher than (1.4 1.7, respectively). Based on these superior activity comparison could be associated, at least part, presence non-aromatic ring conjugated carbonyl system instead phenol moiety.