M. Gonta et al./Chem.J.Mold. 2008, 3 (1), 118-126(d) (e) (f)Fig. 2. The kinetic curves <strong>of</strong> DPPH˙ consumption at the interaction with: (a)-Resv; (b)-ENOXIL; (c)-Eneox;(d)- DFH 4; (e)-EDMD; (f)-Qu; in alcoholic solutions <strong>of</strong> 75%; [DPPH˙]=5·10 -5 MThe data obtained for CE 50are presented in Tab.2. Based on the empirical results, we noticed that the lowestCE 50was characteristic for Eneox (CE 50Eneox=0,14) while the highest - for Resv (CE 50Rezv=1,7). Another more distinctivepeculiarity <strong>of</strong> the antiradical activity <strong>of</strong> the reducers is the antiradical power (ARP), which is to be determined as theopposite mass <strong>of</strong> CE 50(1/CE 50). According to the data displayed in Tab. 2, ARP vary between 2,0 – 12,5, for the studiedantioxidants. The lowest ARP was established for Resv (2,0), and the highest is peculiar for Eneox (12,5). ENX extracthas an ARP Enxequal to 6,7.DPPH', %100806040[DPPH'], %1008060402020(a)00 0.2 0.4 0.6 0.8 1[Red]/[DPPH'](+)-Ct Cv Rezv DFH4 EDMD(b)00 1 2 3 4[Red]/[DPPH']ENXEneoxFig.3. DPPH˙ Concentration Dependence (%) on the molar report [Red]/[DPPH˙]:(a) (+)-Ct, Qu, Resv, DFH4, EDMD; (b) ENX, EneoxThe stoichiometric value equal to CE 100, determined via CE 50multiplication by two, forms the efficientconcentration needed to reduce one 100% <strong>of</strong> DPPH˙. In this case, the classification <strong>of</strong> the antiradical efficiency will beincorrect, for the compounds that have a slow kinetic behaviour, because the reaction might not reach the end.The stoichiometric value that varies within 0.2-1.0 limits is presented in Tab.2 for all the studied reducers. Wealso calculated the opposite amount <strong>of</strong> CE 100(1/CE 100), that determines the number <strong>of</strong> DPPH˙ molls from which 1 moll<strong>of</strong> reducer can be cut.Table 2Classification <strong>of</strong> the antiradical efficiency, in compliance with the kinetic behaviourKinetic Behaviour Compounds Efficient CE 50ConcentrationFast Kinetic Behaviour(1 min)Intermediary KineticBehaviour (5-30 min)Slow Kinetic BehaviourCE 50x2StoichiometricValueARP(1/CE 50)Nr. <strong>of</strong> mollsDPPH˙ reduced(1/ CE 100)Resveratrol 0,5 1,0 2,0 1,0ENX 0,15 0,3 6,7 3,3Eneox 0,08 0,16 12,5 6,25Quercitine 0,1 0,2 10,0 5,0(+)-Catechin 0,1 0,2 10,0 5,0DFH 40,1 0,2 10,0 5,0EDMD 0,15 0,3 6,7 3,3123
M. Gonta et al./Chem.J.Mold. 2008, 3 (1), 118-126According to the data obtained in Tab.2 for the compounds that have an intermediary kinetic behaviour, 1/CE 100coincides with the number <strong>of</strong> hydrogens or hydroxyl groups, available for donation. For quercitine, (+)-catechin, 1/CE 100is approximately 2; thus, a molecule <strong>of</strong> (+)-catechin reduces 2 molecules <strong>of</strong> DPPH˙, fact that corresponds to thenumber <strong>of</strong> hydroxyl groups participating in the reduction process, shown in the scheme below.We calculated 1/CE 100for resveratrol, and we established that three molecules <strong>of</strong> Resv reduce one molecule <strong>of</strong>DPPH˙. Taking into consideration the structure formula <strong>of</strong> the Resv, we might state that dihydroxy-grouping is lacking,i.e. there are no neighbouring dihydroxylic groups. Hence, in this case, the mechanism <strong>of</strong> radicals’ removal is differentfrom the compound that contains dihydroxylic or trihydroxylic groups. The antiradical activity <strong>of</strong> (+)-catechin is lowerthan that <strong>of</strong> the quercitine.The stoichiometric value calculated for DFH 4is 0,8, while the number <strong>of</strong> DPPH˙ molls reduced by a molecule<strong>of</strong> DFH 4is equal to 1,25, though the number <strong>of</strong> hydroxylic groupings is two.We established the degree <strong>of</strong> inhibition (%) <strong>of</strong> DPPH˙ - radical, according to the formula [29]: ID=[A control–A test]100/A control, where A control– is control absorbance (solution <strong>of</strong> DPPH˙ without reducer) and A test– is the absorbance<strong>of</strong> the tested sample (solution <strong>of</strong> DPPH˙ and reducer).124Fig. 4. ID at t=30 min depending on the concentration <strong>of</strong> the studied inhibitorsWe found out that the inhibition degree (ID) increases together with the augmentation <strong>of</strong> the reducers’concentration within the interval <strong>of</strong> 2*10 -5 – 5*10 -4 M.In case <strong>of</strong> the interaction between DPPH˙ radical and DFH 4, Qu, (+)-Ct, for the interval <strong>of</strong> concentrations2*10 -5 – 1*10 -4 M, there is a higher variation <strong>of</strong> the ID (~30-90%), and when [Red]o increases > 1*10 -4. M, the ID variesinsignificantly.Dimethylic ester <strong>of</strong> dihydroxyfumaric acid and ENX (enotanin oxidized extract <strong>of</strong> grapes seeds) interacts slowerwith DPPH˙ and ID varies from ~20% to ~70% for the interval 2*10 -5 – 1*10 -4 M, and due to ongoing increase <strong>of</strong>[Red] oto 5*10 -4 M, ID reaches ~90% in respect to the control. For resveratrol, the augmentation <strong>of</strong> ID during the firstinterval <strong>of</strong> concentrations <strong>of</strong> Red, is the most insignificant (~20-35%), and further on at 5*10 -4 M reaches 90%. In thecase <strong>of</strong> Eneox (enotanin non-oxidized extract from grapes seeds), DPPH˙ radical, in small quantities is wasted mostrapidly. For C red=2*10 -5 M there is an ID=50%. ID correlates positively with 1/CE 100calculated for these reducers(Tab. 2).The greatest number <strong>of</strong> DPPH molecules is reduced by Eneox (6.25), further on Qu (+)-Ct, DFH 4has 1/CE 100equal to 5, EDMD and ENX – 3.3, and Resv reduces the smallest number <strong>of</strong> DPPF molecules (1,0).
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