We report a series of functionalized dienes as compounds of great potential in the treatment of Alzheimer’s disease due to their antioxidant activity and ability to inhibit the enzyme acetylcholinesterase. The dienes tested showed high enzymatic inhibition capacity and accentuated antioxidant activity, which are comparable to or higher than the standards tested. Molecular docking studies were performed to confirm the experimental results. We also describe the correlation values between the antioxidant activity and oxidation potentials. Predicted bioactivity scores and quantum studies were also determined.

Thiosemicarbazones are a class of compounds of interest for Medicinal Chemistry, as they are structurally diverse and have numerous biological activities reported in the literature. This study describes the synthesis of seventeen thiosemicarbazones, which were investigated as potential therapeutic agents for the treatment of Alzheimer's disease through antioxidant tests and an inhibitory assay of the acetylcholinesterase enzyme. All compounds showed excellent inhibition of acetylcholinesterase and exhibited excellent antioxidant action when compared to the standards. In addition, a quantum study was carried out, in which the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy values of each compound were obtained. From these theoretical data, chemical properties were calculated and correlated with the experimental data.

Two new synthetic melanin-like oligomers inspired by the synthesis of pheomelanin (cys-DOPA) were prepared using L-DOPA as a precursor and the amino acids serine (ser-DOPA) and threonine (thr-DOPA) for modifications. The products obtained exhibited appreciable antioxidant activity. The compounds were characterized by liquid chromatography-mass spectrometry (LC-MS), elemental analysis and infrared spectroscopy. The pKa values of the groups present in each melanin suspension were determined in aqueous solution by potentiometric and spectrophotometric titration. Cytotoxicity assays showed an IC50 > 500 mg L-1 resulting in non-toxic compounds for living cells. Finally, cys-DOPA, ser-DOPA and thr-DOPA exhibited antioxidant activity determined by the DPPH scavenging assay, with EC50 = 7.69, 1.02 and 27.60 mg L-1, respectively.

Uma investigação fitoquímica de Polygala molluginifolia (raiz, caule, folhas e flores) resultou no isolamento de quatro piranoisoflavonas das quais a isoflavona1é desconhecida na literatura. As isoflavonas 2-4: , embora sejam compostos sintéticos conhecidos são descritos neste trabalho como novos produtos naturais. Os compostos isolados foram avaliados em termos do seu efeito antioxidante e o potencial para inibir a enzima acetilcolinesterase. As isoflavonas 1 e 4 inibiram a acetilcolinesterase, exibindo valores de IC50 de 68 µmol L-1 e 84 µmol L-1, respectivamente. No ensaio de DPPH, os mesmos compostos e a rutina 5 apresentaram valores de EC50 de 61 µmol L-1, 55 µmol L-1 e 16 µmol L-1, respectivamente. Além disso, a permeabilidade das compostos 1-4 foi testada através do ensaio de permeabilidade em membrana artificial paralela (PAMPA) com as isoflavona 3 (9.25 × 10-6 cm s-1) e 4 (3.48 × 10-6 cm s-1) exibindo as maiores permeabilidades.

A phytochemical investigation of Polygala molluginifolia (root, stem, leaves and flowers) resulted in the isolation of four pyranoisoflavones, of which isoflavone 1 was previously unknown in the literature. Isoflavones 2-4: , although they are known synthetic compounds, are described in this work as new natural products. The isolated compounds were evaluated for their antioxidant effects and potential for inhibiting the acetylcholinesterase enzyme. Isoflavones 1 and 4 inhibited acetylcholinesterase, displaying IC50 values of 68 µmol L-1 and 84 µmol L-1, respectively. In the DPPH assay, the same compounds and rutin 5 exhibited EC50 values of 61 µmol L-1, 55 µmol L-1 and 16 µmol L-1, respectively. Moreover, the permeability of compounds 1-4: was evaluated using parallel artificial membrane permeability assay (PAMPA) with isoflavones 3 (9.25 × 10-6 cm s-1) and 4 (3.48 × 10-6 cm s-1) exhibiting the highest permeabilities.

The liquid-liquid partitioning of a crude hydroalcoholic extract of Averrhoa carambola L., Oxalidaceae, leaves led to the isolation of a sterol and three flavone C-glycosides. From the n-hexane fraction β-sitosterol was isolated and from the ethyl acetate fraction apigenin-6-C-β-L-fucopyranoside (1) and apigenin6-C-(2"-O-α-L-rhamnopyranosyl)-β-L-fucopyranoside (2) were obtained. Apigenin6-C-(2"-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (3) was isolated from the n-butanol fraction. Compound 3 is new, while 1 and 2 have been previously isolated from A. carambola. The antioxidant activity was measured using the DPPH radical scavenging assay and reducing power of iron (III) to iron (II) ions. The ethyl acetate and n-butanol fractions showed the most antioxidant activity. As evaluated by ability of the sample to scavenge DPPH the IC50 values were 90.92 and 124.48 µg/ mL, respectively. In the assay of reducing power these fractions presented 135.64 and 125.12 of ascorbic acid equivalents, respectively. The antioxidant activity exhibited a significant relationship with the phenolic content (r² = 0.997), but a poor relationship with the flavonoids content (r² = 0.424). The n-hexane fraction was the only fraction to present good toxicity using A. salina with LC50 800.2 µg/mL.