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

Author(s)

da Silva, Flavia T. ^[1] ; Gomes, Kaio S. ^[2] ; Machado, Fabricio C. ^[3] ; Loureiro, Leticia L. ^[3] ; Travassos, Luiz R. ^[3] ; Martins, Tereza S. ^[1] ; Lago, Joao Henrique G. ^[2] ; Camilo, Fernanda F. ^[1]

Affiliation

^[1] Univ Fed Sao Paulo, Dept Quim, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP - Brazil

^[2] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210580 Santo Andre, SP - Brazil

^[3] Univ Fed Sao Paulo, Dept Microbiol Imunol & Parasitol, Unidade Oncol Expt, BR-04021001 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 32, n. 5, p. 1002-1008, MAY 2021.
• Web of Science Citations: 0

Abstract

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

• FAPESP's process: 18/20826-4 - SYNTHESIS AND PROPERTIES EVALUATION OF NANOPARTICLES SUPPORTED ON NON-MODIFIED CELLULOSE FILMS
• Grantee: Fernanda Ferraz Camilo
• Support Opportunities: Regular Research Grants
• FAPESP's process: 18/07885-1 - Biomolecules from plant species of remnant areas of the Atlantic Forest and Cerrado to treat neglected tropical diseases - chemical and pharmacological aspects
• Grantee: João Henrique Ghilardi Lago
• Support Opportunities: BIOTA-FAPESP Program - Regular Research Grants