nteraction of isolinderanolide E obtained from Nectandra oppositifolia with biomembrane model

Author(s)

Rosa, Matheus Elias ^[1] ; Alves Conserva, Geanne A. ^[2] ; Lago, Joao Henrique G. ^[2] ; Caseli, Luciano ^[1]

Affiliation

^[1] Univ Fed Sao Paulo, Dept Chem, Diadema, SP - Brazil

^[2] Fed Univ ABC, Ctr Nat & Human Sci, Santo Andre, SP - Brazil

• Document type: Journal article
• Source: BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES; v. 1863, n. 10 OCT 2021.
• Web of Science Citations: 0

Abstract

A long-tail lactone, named isolinderanolide E, was obtained from Nectandra oppositifolia and incorporated in Langmuir monolayers of dipalmitoyl-phosphoethanolamine (DPPE) as a model of microbial membranes. The compound was dissolved in chloroform and mixed with DPPE to provide mixed solutions spread on the air-water interface. After solvent evaporation, mixed monolayers were formed, and surface pressure-area isotherms, dilatational rheology, Brewster angle microscopy (BAM), and infrared spectroscopy were employed to characterize the prodrug-membrane interactions. Isolinderanolide E expanded DPPE monolayers, denoting repulsive interactions. At 30 mN/m, the monolayer presented higher viscoelastic and in-plane elasticity parameters and an increased ratio of all-trans/gauche conformers of the alkyl chains, confirming molecular order. Morphology of the monolayer was analyzed by BAM, which revealed a more homogeneous distribution of Isolinderanolide E along the DPPE monolayer than the prodrug directly spread at the interface, which tends to aggregate. A molecular model proposing the molecular orientation of the amphiphilic drug is presented and explained by the distortion of the alkyl chains as well as by viscoelastic changes. In conclusion, the prodrug changes the thermodynamic, rheological, morphological, and structural properties of the DPPE monolayer, which may be essential to understand, at the molecular level, the action of bioactives in selected membrane models. (AU)

• FAPESP's process: 19/03239-0 - Nanostructured interfaces for the investigation of bioactive substances in cell membrane models and for the construction of optoelectronic devices
• Grantee: Luciano Caseli
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/20633-6 - Bioactive metabolites from Nectandra oppositifolia Nees & Mart. (Lauraceae): molecular characterization, in vitro and in vivo antiparasitic potential evaluation and determination of mechanism of action
• Grantee: Geanne Alexsandra Alves Conserva
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 18/22214-6 - Towards a convergence of technologies: from sensing and biosensing to information visualization and machine learning for data analysis in clinical diagnosis
• Grantee: Osvaldo Novais de Oliveira Junior
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 19/04407-4 - Study of the surface activity of alkylated lactones and their interaction in cell membrane models
• Grantee: Matheus Elias Rosa
• Support Opportunities: Scholarships in Brazil - Scientific Initiation