Details

Autor(en) / Beteiligte

• MARKOVIC, Zoran
• MILENKOVIC, Dejan
• OROVIC, Jelena D
• DIMITRIC MARKOVIC, Jasmina M
• STEPANIC, Višnja
• LUCIC, Bono
• AMIC, Dragan

Titel

PM6 and DFT study of free radical scavenging activity of morin

Ist Teil von

• Food chemistry, 2012-10, Vol.134 (4), p.1754-1760

Ort / Verlag

Kidlington: Elsevier Ltd

Erscheinungsjahr

2012

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• ► Conformational analysis of flavonoid morin is performed. ► Antioxidant action energetics related to radical scavenging mechanisms is examined. ► The 3-OH group is the most favored site for radical inactivation. ► HAT mechanism is thermodynamically preferred in gas-phase. ► The most probable free radical scavenging mechanism in water is SPLET. Flavonoids have long been recognised for their general health-promoting properties, of which their antioxidant activity may play an important role. In this work, we have studied the properties of flavonoid morin using semiempirical and density functional theory (DFT) methods in order to validate the application of the recently developed parametric method 6 (PM6). Reaction enthalpies related to mechanisms of free radical scavenging by flavonoid morin were calculated by DFT and PM6 methods in gas-phase, water, DMSO and benzene. It has been shown that fast semiempirical PM6 method can mimic results obtained by means of more accurate time consuming DFT calculations. Thermodynamically favoured mechanism depends on reaction medium: SPLET (sequential proton loss electron transfer) is preferred in water and DMSO, and HAT (hydrogen atom transfer) is predominant in gas-phase. In benzene these two mechanisms are competitive.