RESUMEN
The organic compound niacin or nicotinic acid, also known as vitamin B3 (VitB3), is essential for human nutrition and metabolic regulation. However, in high doses, it can provoke side effects, such as hyperglycemia, liver damage, and flushing. Development of a controlled release system that slowly releases VitB3 into the organism would avoid high dosing peaks, thus contributing to decrease the occurrence of side effects in nutritional supplementation. Here, we show that the slow and controlled release of VitB3 in an acid environment can be achieved via its intercalation in layered double hydroxides (LDHs). The synthesis of a ZnAl-VitB3 system is shown, in which VitB3 is intercalated in a ZnAl LDH. The presence of VitB3 in the ZnAl-VitB3 system was confirmed by elemental analysis, infrared (FTIR) and NMR spectroscopy, while successful intercalation in the LDHs was revealed by powder X-ray diffraction (PXRD). In vitro release tests were carried out in a concentrated HCl solution of pH 1.5, a pH similar to the human stomach environment. The results showed a steady release of VitB3 from the LDH host, with 90% of the vitamin liberated in the first 60 min after the suspension of the LDH in the acidic solution.
RESUMEN
Betaxanthins are natural products with high antioxidant and anti-inflammatory properties. Here, we describe the semisynthesis of twenty-one betaxanthins derived from proteinogenic amino acids, including the elusive betaxanthin of l-cysteine and two betaxanthins derived from l-lysine, and rationalize their antioxidant properties in mechanistic terms. The antioxidant capacity and redox potential of these betaxanthins were compared to those of model betaxanthins derived from dopamine, l-DOPA (L-3,4-dihydroxyphenylalanine), and pyrrolidine and structure-property relationships were established by using matched molecular pair analysis and a model developed using a genetic algorithm. Either a phenol or indole moiety enhance the antioxidant capacity of betaxanthins, which is overall much higher than that of their amino acid precursors and standard antioxidants, except for the cysteine-betaxanthin. The one-electron oxidation of amino acid betaxanthins produces radicals stabilized in multiple centers, as demonstrated by quantum chemical calculations.