Chemoenzymatic Synthesis and Anti-Inflammatory Activity of Fatty Acid Amides Prepared from Bertholletia excelsa (Brazil Nut) Triglycerides

Pedro Barata,Irlon Ferreira,José Carlos Carvalho,Edilene Silva,Alex Rodrigues,Albenise Barros,Ícaro Sarquis,Helison Carvalho,Adan Galue-Parra

doi:10.21577/0103-5053.20200041

Abstract

This study reports the synthesis of fatty acid amides (FAA), analogous to anandamide, prepared from Brazil nut oil (BNO), using Amano lipase from Pseudomonas fluorescens as a catalyst of direct aminolysis, with a good yield (95-68%). The anti-inflammatory effects of BNO and FAA were evaluated by the carrageenan-induced paw edema method. Analysis of the formation of edema showed that these FAA, at all dose used, significantly reduced the development of edema.

Highlights

Anandamide derivatives are known as N-arachidonoyl ethanolamide or fatty acid amides (FAA) and were identified and characterized as neuromodulators of the endogenous endocannabinoid class.[1]
When the amidation reaction of the triglyceride from the Bertholletia excelsa oil was performed in the absence of lipase from Pseudomonas fluorescens (LPF) for 96 h with magnetic stirring (300 rpm; 40 °C), the amide product yield was 17%, after purification on a chromatographic column with silica gel (Table 1, entry 3)
The direct amidation reaction of Brazil nut oil (BNO), catalyzed by LPF, was performed in the presence of hexane (1.0 mL) (Table 1, entry 4), with the objective of comparing the yield for fatty amides obtained under solvent-free conditions

Summary

Introduction

Anandamide derivatives are known as N-arachidonoyl ethanolamide or fatty acid amides (FAA) and were identified and characterized as neuromodulators of the endogenous endocannabinoid class.[1]. Soc. transformation of triglycerides from Brazil nut oil (BNO) into fatty acid amides (FAA) set.

Results

Conclusion