Flavonols from Pterogyne nitens and their evaluation as myeloperoxidase inhibitors.
A myeloperoxidase inhibitory kaempferol derivative, namely pterogynoside (1), was isolated from fruits of Pterogyne nitens, along with six known flavonols, kaempferol, afzelin, kaempferitrin, quercetin, isoquercetrin and rutin. The structures of all compounds were elucidated primarily from 1D and 2D NMR spectroscopic analyses, as well as by high resolution mass spectrometry. All flavonols were screened to identify secondary metabolites as potential myeloperoxidase (MPO) inhibitors, and at concentrations of 0.50-50nM, quercetin (5), isoquercitrin (6) and rutin (7) exhibited strong inhibitory effects with IC50 values of 1.22+/-0.01, 3.75+/-0.02 and 3.60+/-0.02, respectively. The MPO activity detected for the new derivative 1 was markedly decreased (IC(50) 10.3+/-0.03) when compared with known flavonols 5-7, and interestingly increased when tested against ABTS scavenging activity.
Regasini
Luis Octávio
LO
Universidade Estadual Paulista, Instituto de Química, NuBBE - Núcleo de Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais, Araraquara, SP, CP 355, CEP 14801-970, Brazil.
Vellosa
José Carlos Rebuglio
JC
Silva
Dulce Helena Siqueira
DH
Furlan
Maysa
M
de Oliveira
Olga Maria Mascarenhas
OM
Khalil
Najeh Maissar
NM
Brunetti
Iguatemy Lourenço
IL
Young
Maria Claudia Marx
MC
Barreiro
Eliezer Jesus
EJ
Bolzani
Vanderlan Silva
VS
D004353:Drug Evaluation, Preclinical; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D007887:Fabaceae / Q000737:chemistry*; D044948:Flavonols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009195:Peroxidase / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D044948:Flavonols; C531205:pterogynoside; D009195:Peroxidase