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An Acad Bras Cienc ; 93(4): e20200443, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34495202


Phytochemical studies of Cespedesia spathulata (Ochnaceae) leaves using 1H, 13C NMR, and GC-MS have led to the isolation of some metabolites identified for the first time in these species such as cathechin, epicatechin, vitexin, orientin, 6''-O-acetyl-vitexin, sitosterol, stigmasterol, phytol, 4,5-dihydrovomifoliol and a mixture of aliphatic methyl esters, together with ochnaflavone, which was previously isolated from this plant. The modulating activity of some fractions and compounds from Cespedesia spathulata towards tyrosinase enzyme was assayed by spectroscopic and theoretical means/experiments. The dichloromethane fraction (133 µg mL-1) and ochnaflavone (333 µM) inhibited tyrosinase activity by 20 % and 2.0 %, respectively, whereas the ethyl acetate fraction (666 µg mL-1) and ±catechins (catechin and epicatechin - 800 µM) activated it by 104 % and 384 %, respectively. Quantum chemical calculations suggested that catechin and epicatechin are better activators than L-DOPA by interacting with Cu (II) ions. Molecular docking results suggested that hydrogen bonding and hydrophobic interactions are the main binding forces between each tyrosinase activator and the amino acid residues inside the active protein binding pocket.

Ochnaceae , Simulação de Acoplamento Molecular , Monofenol Mono-Oxigenase , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta
Rev. bras. farmacogn ; 26(3): 321-325, May-June 2016. tab, graf
Artigo em Inglês | LILACS-Express | LILACS | ID: lil-784288


Abstract The aim of the current study is to evaluate the effect of Acmella oleracea (L.) R.K. Jansen, Asteraceae, methanolic extract, hexane (84.28% spilanthol) and dichloromethane (approximately 100% spilanthol) fractions on the tyrosinase enzyme. The dehydrated jambu extract was obtained through maceration using methanol. The extract residue was solubilized in MeOH/H2O (8:2) and subjected to liq.–liq. partition in organic solvents. Both the extraction and the partition procedures were conducted with three replicates. The analyses were performed using GC–MS, 1H and 13C NMR. The hexane fraction provided samples containing 84.28, 82.91 and 62.83% spilanthol in repetitions 1, 2 and 3, respectively. The dichloromethane fraction showed 88.55% spilanthol in repetition 1, and approximately 100% spilanthol in repetitions 2 and 3. The jambu extract as well as the hexane fraction (84.28% spilanthol) were able to activate the oxidizing activity of the tyrosinase enzyme for L-DOPA. The dichloromethane fraction (approximately 100% spilanthol) showed stronger inhibition effect on the tyrosinase enzyme in the first 10 min. The results raise the interest in study in spilanthol formulations for topical use, since it may prevent and/or slow skin hyperpigmentation or depigmentation processes. Furthermore, spilanthol may be used to control the enzymatic browning in fruits and vegetables.

Rev. bras. farmacogn ; 21(3): 397-401, maio-jun. 2011. ilus
Artigo em Inglês | LILACS-Express | LILACS | ID: lil-593288


The phytochemical investigation of the roots of Piptadenia rigida Benth., Fabaceae, known as "angico", afforded sitosterol, lupeol, betuline, the chalcone isoliquiritigenin, the flavonoids, 7,4'-dihydroxyflavone, 7,3',4'-trihydroxyflavone, 7,8,3',4'-tetrahydroxyflavanone, 4-hydroxy-3,5-dimethoxybenzaldehyde and methyl-3,4-dihydroxy-benzoate. Both flavones were also isolated from the branches of this plant. Five derivatives of the aldehyde were obtained by diazomethane treatment. The structures of compounds were identified by IR, NMR and mass spectral data analysis of natural compounds and some derivatives, and by comparison with literature data.