Electronic supplementary material
Antioxidant and free radical scavenging activity of purpurin
Svetlana R. Jeremić1, Sefedin Šehović2, Nedeljko T. Manojlović3, and Zoran S. Marković1
1Svetlana R. Jeremić, Department of Biochemical and Medical Sciences, State University of Novi Pazar, Novi Pazar 36300, Serbia, e-mail: sjeremic@ kg.ac.rs
2 Sefedin Šehović, Teacher Training Faculty, University of Belgrade, Vuka Karadžića bb, Novi Pazar 36300, Serbia, e-mail: ufbgonp@ yahoo.com
3 Nedeljko T. Manojlović, Department of Pharmacy, Medical Faculty, University of Kragujevac, 34000 Kragujevac, Serbia, e-mail:
1 Zoran S. Marković* (*), Department of Biochemical and Medical Sciences, State University of Novi Pazar, Novi Pazar 36300, Serbia, e-mail:
Bond angles for purpurin (1), the most stable radical and anion in both gas and water solution.
A(C1-C2-C3) / 120.612 / 120.717 / 122.809 / 122.663 / 115.241 / 116.377
A(C2-C3-C4) / 120.188 / 120.015 / 118.464 / 118.558 / 122.841 / 121.972
A(C3-C4-C12) / 120.206 / 120.570 / 121.766 / 121.867 / 121.802 / 121.740
A(C4-C12-C10) / 119.954 / 120.144 / 117.873 / 118.253 / 119.872 / 120.309
A(C12-C10-C13) / 118.107 / 118.527 / 118.735 / 118.865 / 117.431 / 118.374
A(C10-C13-C5) / 118.998 / 119.287 / 119.325 / 119.520 / 119.178 / 119.545
A(C13-C5-C6) / 119.844 / 119.953 / 119.584 / 119.703 / 120.317 / 120.167
A(C5-C6-C7) / 120.327 / 120.237 / 120.099 / 120.089 / 120.323 / 120.284
A(C6-C7-C8) / 120.125 / 120.122 / 120.391 / 120.318 / 119.788 / 119.949
A(C7-C8-C14) / 119.749 / 119.897 / 119.803 / 119.908 / 120.173 / 120.065
A(C8-C14-C9) / 119.161 / 119.335 / 118.666 / 119.100 / 119.299 / 119.383
A(C13-C14-C9) / 120.677 / 120.662 / 121.590 / 121.213 / 120.566 / 120.580
A(C10-C13-C14) / 121.208 / 120.926 / 120.296 / 120.186 / 121.557 / 120.958
A(C14-C9-C11) / 117.988 / 118.306 / 117.144 / 117.879 / 117.353 / 118.070
A(C9-C11-C12) / 121.155 / 120.736 / 120.675 / 120.401 / 120.842 / 120.276
A(C1-C11-C9) / 120.200 / 120.179 / 119.904 / 120.031 / 118.641 / 119.353
A(C11-C12-C4) / 119.181 / 119.012 / 120.567 / 120.291 / 117.877 / 117.949
A(C11-C1-C2) / 119.613 / 119.508 / 116.974 / 117.053 / 121.722 / 121.592
A(O1-C1-C2) / 115.667 / 115.878 / 115.669 / 116.308 / 115.925 / 115.280
A(O2-C2-C3) / 120.782 / 119.942 / 122.934 / 121.862 / 125.228 / 124.214
A(O4-C4-C3) / 117.411 / 117.191 / 117.462 / 117.367 / 119.755 / 118.453
A(O10-C10-C12) / 122.170 / 121.641 / 121.151 / 120.822 / 124.212 / 122.657
A(O9-C9-C11) / 121.378 / 121.158 / 122.700 / 122.190 / 123.033 / 121.775
The optimized geometries of purpurin and some stable radicals and anions.
Purpurin structure 1
0 1
C -3.19100900 1.14618400 0.00003600
C -2.89977800 -1.62070000 -0.00002900
C -4.16124400 -1.05504200 0.00004000
C -4.30586000 0.32725800 0.00007300
H -3.27986600 2.22167200 0.00005800
H -2.75989900 -2.69075300 -0.00007100
H -5.03563000 -1.68880200 0.00006100
H -5.29318100 0.76442200 0.00012300
C 1.98468300 -1.09804000 0.00001500
C 3.12642900 -0.25919900 0.00001900
C 0.72668200 -0.53576700 -0.00005200
C 2.99079800 1.10150100 0.00001600
C 0.57542400 0.87565100 -0.00002600
C 1.71527700 1.68266200 0.00002000
H 3.86331300 1.73640700 0.00005000
C -1.77754500 -0.80238200 -0.00005900
C -1.92181400 0.58489800 -0.00002000
C -0.43598400 -1.42057100 -0.00020200
C -0.73848100 1.48130400 -0.00006300
O -0.30973700 -2.64354800 -0.00014900
O -0.89759900 2.70275100 -0.00010700
O 2.23226100 -2.41612900 0.00015500
H 1.35348300 -2.86680000 0.00030400
O 4.34045400 -0.82762200 0.00006700
H 4.23046500 -1.78723000 0.00006300
O 1.64761200 3.01111900 0.00010800
H 0.69191900 3.25196800 0.00019800
E=-914.501482
Purpurin structure 1 in water
0 1
C 3.19299100 1.14758100 0.00008600
C 2.90393100 -1.61778900 -0.00005000
C 4.16629000 -1.05112600 0.00000000
C 4.31020800 0.33035500 0.00007800
H 3.29756200 2.22141600 0.00010400
H 2.78117700 -2.68974300 -0.00007100
H 5.04027100 -1.68535300 -0.00000500
H 5.29653100 0.76948000 0.00011200
C -1.98921000 -1.10171700 -0.00000100
C -3.12691700 -0.25876800 0.00000100
C -0.72819700 -0.54141500 -0.00001100
C -2.98827000 1.10177400 0.00000100
C -0.57430700 0.87008800 -0.00006100
C -1.71339300 1.67463900 -0.00003700
H -3.86198900 1.73664200 -0.00000600
C 1.77939000 -0.80291800 -0.00000900
C 1.92354500 0.58604700 0.00000400
C 0.43970600 -1.42014000 0.00012900
C 0.74055400 1.47268900 -0.00018400
O 0.31512700 -2.64673500 -0.00041400
O 0.89187300 2.70172100 0.00046300
O -2.23781500 -2.42281900 0.00012300
H -1.36407700 -2.87790700 0.00026000
O -4.35586200 -0.80911300 0.00003600
H -4.28380700 -1.77435000 0.00004400
O -1.64322800 3.01614800 -0.00017300
H -0.68434800 3.25040100 -0.00038000
E=-914.517389
O1R
0 2
C -3.17900600 1.17054100 -0.00006800
C -2.94180100 -1.60232800 0.00020700
C -4.19030700 -1.00794700 0.00034000
C -4.30990700 0.37772100 0.00019500
H -3.24481600 2.24758000 -0.00018000
H -2.82373700 -2.67502500 0.00027200
H -5.07773900 -1.62363700 0.00053800
H -5.28804500 0.83456900 0.00029000
C 2.04682500 -1.18615200 -0.00003500
C 3.19642500 -0.24884000 0.00006500
C 0.72670900 -0.60297500 -0.00015800
C 3.04562800 1.09921600 0.00007800
C 0.59113800 0.78307400 -0.00018100
C 1.74563200 1.62659000 0.00000300
H 3.89000100 1.77025600 0.00021300
C -1.80143600 -0.81155300 -0.00005700
C -1.92257900 0.57439100 -0.00017300
C -0.46782300 -1.47921700 -0.00035500
C -0.72317500 1.42335100 -0.00042800
O -0.39276100 -2.68504600 0.00024600
O -0.83459800 2.65294700 -0.00064800
O 2.33458000 -2.38267700 0.00011100
O 4.37344200 -0.83699900 0.00014700
H 4.18282700 -1.79738000 0.00008300
O 1.62292100 2.92925300 0.00033200
H 0.63489200 3.12859300 0.00068000
E=-913.8597484
O1RW
0 2
C -3.18061500 1.17100700 -0.00000700
C -2.94261300 -1.60024100 0.00016200
C -4.19325100 -1.00703000 0.00024100
C -4.31294400 0.37721900 0.00015500
H -3.26115300 2.24692200 -0.00009100
H -2.84306700 -2.67443300 0.00023300
H -5.07922100 -1.62454500 0.00037100
H -5.29060000 0.83484400 0.00021200
C 2.04371900 -1.18629400 -0.00010500
C 3.19298800 -0.25848400 0.00006500
C 0.72507100 -0.59828000 -0.00009400
C 3.04537900 1.08901600 0.00006400
C 0.59116200 0.78344600 -0.00013600
C 1.75037500 1.62031100 -0.00003900
H 3.89591400 1.75358100 0.00016300
C -1.80186600 -0.80988800 0.00001800
C -1.92397800 0.57793000 -0.00008000
C -0.47022400 -1.46468400 -0.00001000
C -0.72588600 1.42354700 -0.00030900
O -0.39059000 -2.68083100 -0.00025900
O -0.83148600 2.65477600 -0.00027300
O 2.31391900 -2.39450500 0.00019900
O 4.38548200 -0.83009800 0.00015300
H 4.24795400 -1.79637400 0.00008600
O 1.63458400 2.92784400 0.00008900
H 0.65099700 3.13706100 0.00019400
E=-913.881364
O2AW
-1 1
C 3.12753300 1.18410500 -0.00007200
C 2.89164700 -1.58376700 0.00005700
C 4.14333200 -0.99631300 0.00003400
C 4.25980200 0.38858300 -0.00003500
H 3.21308400 2.25956500 -0.00011200
H 2.78826000 -2.65791900 0.00009500
H 5.02914600 -1.61401800 0.00006200
H 5.23752200 0.84696200 -0.00005300
C -2.00231600 -1.14790600 0.00003000
C -3.21903900 -0.33131700 0.00010500
C -0.75131100 -0.57671100 0.00002300
C -3.03607800 1.06027000 0.00002200
C -0.60568700 0.84948400 0.00002700
C -1.77751800 1.63333800 0.00002600
H -3.90761300 1.69941200 -0.00000300
C 1.74978600 -0.79036400 0.00001100
C 1.86568000 0.60261200 -0.00003500
C 0.42234700 -1.43275600 -0.00003100
C 0.66417800 1.46642400 -0.00001900
O 0.32864700 -2.66976700 0.00020000
O 0.81231200 2.71889900 -0.00025500
O -1.68432700 2.97579100 0.00010600
H -0.70217800 3.17610000 0.00030600
O -2.20230400 -2.47226700 -0.00006800
H -1.30464100 -2.88860500 -0.00018300
O -4.34779500 -0.89960300 -0.00010500
E=-914.073473