RESUMO
The enzyme tyrosinase is involved in the biosynthesis of melanin and the enzymatic browning of fruits and vegetables, and therefore, its inhibitors have potential to treat hyperpigmentary disorders or to function as food antibrowning agents. The use of hydrazine monohydrate as a reagent to prepare chemically engineered extracts can lead to semisynthetic compounds that contain the portion N-N, a fragment rarely found in natural products and present in some tyrosinase inhibitors. Here, we report the tyrosinase inhibition screening of a series of chemically engineered extracts that are diversified by reaction with hydrazine. LC-MS was used to evaluate the change in composition produced by the reaction. Bioguided fractionation of the most active chemically engineered extract, prepared from Matricaria recutita L., led to the discovery of a pyrazole that inhibits tyrosinase with an IC50 value of 28.20 ± 1.13 µM. This compound was produced by a one-pot double chemical transformation of its natural precursor, which includes an unexpected selective removal of one -OH group.
Assuntos
Inibidores Enzimáticos/química , Hidrazinas/química , Matricaria/química , Extratos Vegetais/química , Engenharia Química , Desenho de Fármacos , Flavonas/química , Melaninas/química , Melaninas/metabolismo , Estrutura Molecular , Monofenol Mono-Oxigenase/antagonistas & inibidores , Pirazóis/química , Relação Estrutura-AtividadeRESUMO
This paper focuses on environmental concerns regarding used antifreeze. It shows the results of laboratory respirometric tests conducted to evaluate the potential impact of antifreeze on activated sludge. In this first step of the study, only the components of virgin antifreeze were addressed, i.e. ethylene glycol, and antifoaming and corrosion inhibitory substances. The plateau resulting from oxygen uptake rate measurements of mixed liquor taken at the end of an aeration tank is used as a reference to evaluate the response of biomass to pulse injection of increasing dosages of new antifreeze, compared to that of formaldehyde, a known toxic compound. While 200 mg/L of formaldehyde steadily decreased the biomass activity (7 mg O2/Lh), there were no toxicity effects for doses up to 5000 mg/L of ethylene glycol from new antifreeze coolant (23 mg O2/Lh, compared to the initial 15 mg O2/Lh for the mixed liquor). It is estimated that ethylene glycol concentration in municipal wastewaters should be several order of magnitude lower then the 1000 mg/L shown to be tolerated by the biomass in this work, but at the present stage, the research does not provide enough information to recommend a definitive management scheme for antifreeze discharge. Many other management issues for used antifreeze must be addressed in future studies before any decision on tolerating sewer discharge in Mexico, as a transitory management option that will conciliate the actual practices with legality, can be made.