Antitrypanosomal activity of epi-polygodial from Drimys brasiliensis and its effects in cellular membrane models at the air-water interface

Author(s)

Guimaraes Goncalves, Giulia Elisa ^[1] ; Morais, Thiago Rahal ^[1] ; Gomes, Kaio de Souza ^[2] ; Costa-Silva, Thais Alves ^[2] ; Tempone, Andre Gustavo ^[3] ; Ghilardi Lago, Joao Henrique ^[2] ; Caseli, Luciano ^[1]

Affiliation

^[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Sao Paulo - Brazil

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

^[3] Adolfo Lutz Inst, Ctr Parasitol & Micol, Sao Paulo - Brazil

• Document type: Journal article
• Source: BIOORGANIC CHEMISTRY; v. 84, p. 186-191, MAR 2019.
• Web of Science Citations: 0

Abstract

Epi-polygodial, a drimane sesquiterpene was isolated from Drimys brasiliensis (Winteraceae). This compound demonstrated high parasite selectivity towards Trypanosoma cruzi trypomastigotes (IC50 = 5.01 mu M) with a selectivity index higher than 40. These results were correlated with the effects observed when this compound was incorporated in cellular membrane models of protozoans, represented by Langmuir monolayers of dipalmitoylphosphoethanolamine (DPPE). Surface pressure-area isotherms showed that epi-polygodial expands DPPE monolayers at higher areas and condenses them at lower areas, which was attributed to the preferential interaction with the polar heads of the lipid. This mechanism of action could be corroborated with Polarization-Modulation Reflection-Absorption Spectroscopy and Brewster Angle Microscopy. These results pointed to the fact that the interaction of epi-polygodial with DPPE monolayers at the air-water interface affects the physical chemical properties of the mixed film, which may be important to comprehend the interaction of this drug with cellular membranes at the molecular level. (AU)

• FAPESP's process: 15/23446-0 - Smart surfaces: nanostructured and bioinspired systems for the investigation of molecular interactions in membrane models and for the production of devices for biosensors and environmental analysis
• Grantee: Luciano Caseli
• Support type: Regular Research Grants
• FAPESP's process: 13/14262-7 - Nanostructured films from biologically-relevant materials
• Grantee: Osvaldo Novais de Oliveira Junior
• Support type: Research Projects - Thematic 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 type: BIOTA-FAPESP Program - Regular Research Grants
• FAPESP's process: 15/23403-9 - Rational Pre-Clinical Study of New Drug Candidates Against Neglected Protozoan Diseases Using Pharmacokinetic Approaches
• Grantee: André Gustavo Tempone Cardoso
• Support type: Regular Research Grants