ABSTRACT Ferulic acid (FA) is a phenolic compound with well-known antioxidant potential that can be used as a promising anti-inflammatory and anti-cancer molecule. Furthermore, it has been reported to have neuroprotective activity. One of the main problems, which limit its clinical use, is its low bioavailability when administered orally. This limitation can be circumvented by changes in their structure and/or for preparing lipid-based formulations. The aim of this study was to synthesize a derivative of FA, the hexadecyl ferulate (HF). This compound would be more susceptible to pass through blood-brain barrier (BBB) due to its lipophilic character. The HF was obtained by Steglich esterification and yielded 76.77 ± 1.35%. Its structural characterization was performed by spectroscopic methods of Fourier-transformed infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR). FTIR spectrum of HF presented two typical bands of ester group, a C=O ester stretching band at 1725 cm-1 and a C-O stretching band at 1159 cm-1. The 1H and 13C spectral data confirmed the chemical structure of HF. Regarding the 13C NMR spectrum, HF showed a chemical shift at δ 167.39 ppm which corresponded to the carbonyl carbon of the ester group. Concerning the in vitro antioxidant potential, HF had equivalent or improved scavenger activity than FA leading to IC50 values of 0.083 ± 0.009 nmol.mL-1 and 0.027 ± 0.002 nmol.mL-1 in DPPH radical scavenging and ABTS radical cation decolorization assays, respectively. Further studies are required in order to investigate the antioxidant effect of HF in biological media.
Synadenium grantii Hook f., Euphorbiaceae, is popularly known as leitosinha or janaúba. The diluted latex (18 drops/L of water) is commonly used in the south of Brazil to treat gastric disturbances. This study evaluated phytochemical screening and toxicity using Artemia salina Leach of crude bark extract and also latex. The toxicity and the anti-ulcer activity of S. grantii latex were also tested in rats. Phytochemical results showed presence of tannins, terpenes, unsaponificable substances, coumarins and anthraquinones in the crude bark extract and terpenes in the latex. Gas chromatography-mass spectrometry (GC-MS) analysis demonstrated the presence of diterpene tigliane esters in the latex, identified as 12-deoxyphorbol-13-(2-metilpropionate) and phorbol 12,13,20-triacetate. The toxicity results using A. salina presented CL50 26.58μg/mL and CL50 778.66μg/mL, for the latex and the crude bark extract respectively. The toxicological hepatic parameters of the diluted latex were not different to the control group (p<0.05). The eosinophils cells showed an increase in both the diluted and pure latex groups. The pure latex showed gastric protection of 90% (p<0.05) and the diluted latex showed 6% compared to the negative control. Therefore, our data indicate that S. grantii latex, under research conditions presented gastric protection. Pure latex showed more toxicity than the diluted latex.