Journal Article

Synthesis of the Natural Product 1,3-Dibehenyl-2-ferulyl Glyceride (Aquilaria malaccensis) and Its Derivatives

Nieto-Camacho, Antonio, Chávez-Riveros, Alejandra, Sánchez-Esparza, Alexis de Jesús, Ortega-Ruiz, Miguel Ángel, Cantú-Reyes, Margarita, Osorio-Godínez, Oscar Yael, Fragoso-Medina, Amira Jalil, Contreras-Cruz, David Atahualpa, Cuevas, Gabriel

2026

Overview

The first optimal and suitable synthetic route was developed to obtain the natural product 1,3-dibehenyl-2-ferulyl glyceride (1) in four reaction steps with an overall yield of 23%. Additionally, a collection of ten derivatives of the natural product was prepared with similar reaction yields. Compound 19 showed potent antioxidant activity through the DPPH assay with an inhibition higher than 95% (IC50 17.58 ± 0.45 µM). Furthermore, its characterization using 1H NMR, 13C NMR, IR and MS techniques is presented. This work is relevant because it addresses the need for a natural product with very low availability and that comes from an endangered species. The compounds feature a conjugated lipid–drug structure, with cinnamic, caffeic and ferulic acids in the pharmacologically active portion, making its evaluation in biological tests of great interest.

• Publisher: MDPI AG,Multidisciplinary Digital Publishing Institute (MDPI)
• Subject: 1,3-dibenhenyl-2-ferulyl glyceride / Antioxidants / Antioxidants - chemical synthesis / Antioxidants - chemistry / Antioxidants - pharmacology / Aquilaria malaccensis / Biological Products - chemical synthesis / Biological Products - chemistry / Cancer / Catalysis / cosmetical industry / Cosmetics / Coumaric Acids - chemistry / Endangered & extinct species / Endangered species / Equilibrium / Fatty acids / Glycerides - chemical synthesis / Glycerides - chemistry / Glycerides - pharmacology / Glycerol / Lipids / Metabolism / Metabolites / Molecular Structure / Monoglycerides / natural product / Natural products / Product introduction / Reagents / synthesis