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

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.