Incorporation of dehydrodieugenol, a neolignan isolated from Nectandra leucantha (Lauraceae), in lipid Langmuir monolayers as biomembrane models

Autor(es)

Goncalves, Giulia Elisa G. ; Umehara, Eric ; Lago, Joao Henrique G. ; Caseli, Luciano

• Tipo de documento: Artigo Científico
• Fonte: BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES; v. 1864, n. 11, p. 10-pg., 2022-08-18.

Resumo

Dehydrodieugenol, a neolignan isolated from the Brazilian plant Nectandra leucantha (Lauraceae) with reported antiprotozoal and anticancer activity, was incorporated in Langmuir monolayers of selected lipids as cell membrane models, aiming to comprehend its action mechanism at the molecular level. The interaction of this compound with the lipids dipalmitoylphosphatidylcholine (DPPC), dipalmitoylphosphatidylethanolamine (DPPE), dipalmitoylphosphatidylserine (DPPS), and dipalmitoylphosphatidylglycerol (DPPG) was inferred through tensiometry, infrared spectroscopy, and Brewster angle microscopy. The interactions had different ef-fects depending on the chemical nature of the lipid polar head, with expansion for DPPC monolayers, conden-sation for DPPE, and expansion (at low surface pressures) followed by the overlap of the isotherms (at high surface pressure values) for DPPS and DPPG. Effects caused by dehydrodieugenol in the negatively charged lipids were distinctive, which was also reflected in the hysteresis assays, surface potential-area isotherms, and rheo-logical measurements. Infrared spectroscopy indicated that the drug interaction with the monolayer affects not only the polar groups, but also the acyl lipid chains for all lipids. These results pointed to the fact that the interaction of the drug with lipid monolayers at the air-water interface is modulated by the lipid composition, mainly considering the polar head of the lipids, as well as the hydrophobicity of the lipids and the drug. As negatively charged lipids pointed to distinctive interaction, we believe this can be related to the antiprotozoal and anticancer properties of the compound. (AU)

• Processo FAPESP: 19/03239-0 - Interfaces nanoestruturadas para a investigação de substâncias bioativas em modelos de membrana celular e para a construção de dispositivos optoeletrônicos enzimáticos
• Beneficiário: Luciano Caseli
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 21/02391-3 - Desenvolvimento e Manutenção da Infraestrutura para pesquisa do Instituto de Física de São Carlos - Universidade de São Paulo - 2021
• Beneficiário: Osvaldo Novais de Oliveira Junior
• Modalidade de apoio: Auxílio à Pesquisa - Reserva Técnica para Infraestrutura Institucional de Pesquisa
• Processo FAPESP: 21/02789-7 - Busca de metabólitos bioativos com ação antiparasitária em espécies vegetais de regiões de Mata Atlântica e Cerrado - uma abordagem química, fenotípica e metabolômica
• Beneficiário: João Henrique Ghilardi Lago
• Modalidade de apoio: Auxílio à Pesquisa - Programa BIOTA - Regular