European Food Research and Technology

Antioxidant and antimalarial properties of butein and homobutein based on their ability to chelate iron (II and III) cations: A DFT study in vacuo and in solution

European Food Research and Technology,

Kemoabetswe. R. N. Serobatseand Mwadham. M. Kabanda*,

Department of Chemistry, Faculty of Agriculture, Science and Technology, School of Mathematical and Physical Science, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa*

0.000 (0.000) 6.995 (3.402) 11.405 (3.011) 22.660 (6.979) 34.607 (11.700)

B-an-1 B-an-2 B-an-3 B-an-4 B-an-5

0.000 (2.323) 1.180 (0.000) 24.343 (8.530)

hB-an-1 hB-an-2 hB-an-3

Fig. S1 The deprotonated species of butein and homobutein, B3LYP/6-31+G(d,p) results in vacuo and in solution. Relative energy values (kcal/mol) are shown below each structure with the relative energy in water solution reported in brackets. The charges on the atoms are shown in blue colour while the hydrogen bond length (Å) formed after deprotonation are shown in red colour.

Antioxidant and antimalarial properties of butein and homobutein based on their ability to chelate iron (II and III) cations: A DFT study in vacuo and in solution

European Food Research and Technology

Kemoabetswe. R. N. Serobatseand Mwadham. M. Kabanda*

Department of Chemistry, Faculty of Agriculture, Science and Technology, School of Mathematical and Physical Science, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa*

Table S1 Bond critical point data for the ligandFen+ complexes, UB3LYP/6-31+G(d,p) results inwater solution

Complex / Bond type / 
eÅ3 / 2
eÅ5 / V
Hartree / G
Hartree / H
Hartree / / atomic-atomic spin density
B-Fe(II)-1 / O2∙∙∙Fe / 0.044 / 0.242 / 0.056 / 0.058 / 0.0023 / 0.961 / 0.044
O9∙∙∙Fe / 0.072 / 0.379 / 0.101 / 0.098 / 0.0032 / 1.032 / 0.027
B-Fe(II)-2 / O3∙∙∙Fe / 0.042 / 0.220 / 0.051 / 0.053 / 0.0020 / 0.963 / 0.034
O4∙∙∙Fe / 0.044 / 0.243 / 0.056 / 0.058 / 0.0022 / 0.962 / 0.034
B-Fe(II)-1-an / O2∙∙∙Fe / 0.090 / 0.478 / 0.141 / 0.130 / 0.0105 / 1.081 / 0.039
O9∙∙∙Fe / 0.075 / 0.393 / 0.107 / 0.103 / 0.0043 / 1.042 / 0.064
B-Fe(II)-2-an-a / O3∙∙∙Fe / 0.037 / 0.165 / 0.040 / 0.041 / 0.0008 / 0.981 / 0.051
O4∙∙∙Fe / 0.083 / 0.432 / 0.124 / 0.116 / 0.0079 / 1.069 / 0.016
B-Fe(II)-2-an-b / O3∙∙∙Fe / 0.092 / 0.471 / 0.141 / 0.129 / 0.0117 / 1.091 / 0.012
O4∙∙∙Fe / 0.030 / 0.150 / 0.035 / 0.036 / 0.0013 / 0.964 / 0.052
B-Fe(III)-1 / O2∙∙∙Fe / 0.049 / 0.261 / 0.060 / 0.063 / 0.0024 / 0.962 / 0.054
O9∙∙∙Fe / 0.074 / 0.424 / 0.112 / 0.109 / 0.0029 / 1.027 / 0.033
B-Fe(III)-2 / O3∙∙∙Fe / 0.021 / 0.080 / 0.021 / 0.020 / 0.0004 / 1.022 / 0.016
O4∙∙∙Fe / 0.023 / 0.095 / 0.024 / 0.024 / 7.00x 10-5 / 0.997 / 0.018
B-Fe(III)-3 / C5∙∙∙Fe / 0.019 / 0.044 / 0.015 / 0.013 / 0.0019 / 1.148 / 0.042
B-Fe(III)-1-an / O2∙∙∙Fe / 0.111 / 0.584 / 0.191 / 0.169 / 0.0226 / 1.134 / 0.082
O9∙∙∙Fe / 0.090 / 0.439 / 0.132 / 0.121 / 0.0110 / 1.091 / 0.070
B-Fe(III)-2-an-a / O3∙∙∙Fe / 0.031 / 0.146 / 0.033 / 0.035 / 0.0017 / 0.952 / 0.040
O4∙∙∙Fe / 0.067 / 0.374 / 0.097 / 0.095 / 0.0017 / 1.018 / 0.032
B-Fe(III)-2-an-b / O3∙∙∙Fe / 0.077 / 0.414 / 0.112 / 0.108 / 0.0042 / 1.039 / 0.038
hB-Fe(II)-3new / O2∙∙∙Fe / 0.046 / 0.257 / 0.059 / 0.062 / 0.0025 / 0.960 / 0.047
O9∙∙∙Fe / 0.069 / 0.370 / 0.097 / 0.947 / 0.8498 / 0.102 / 0.031
hB-Fe(II)-1new / O3∙∙∙Fe / 0.043 / 0.225 / 0.053 / 0.054 / 0.0017 / 0.969 / 0.037
O4∙∙∙Fe / 0.046 / 0.256 / 0.059 / 0.062 / 0.0023 / 0.963 / 0.034
hB-Fe(II)-5 / C5∙∙∙Fe / 0.022 / 0.054 / 0.018 / 0.016 / 0.0023 / 1.148 / 0.013
hB-Fe(II)-3-an / O2∙∙∙Fe / 0.087 / 0.463 / 0.134 / 0.125 / 0.0090 / 1.073 / 0.038
O9∙∙∙Fe / 0.070 / 0.405 / 0.106 / 0.103 / 0.0023 / 1.022 / 0.060
hB-Fe(II)-1-an / O3∙∙∙Fe / 0.040 / 0.210 / 0.049 / 0.051 / 0.0018 / 0.964 / 0.063
O4∙∙∙Fe / 0.083 / 0.420 / 0.121 / 0.113 / 0.0080 / 1.071 / 0.007
hB-Fe(III)-3new / O2∙∙∙Fe / 0.047 / 0.238 / 0.055 / 0.057 / 0.0022 / 0.961 / 0.047
O9∙∙∙Fe / 0.070 / 0.396 / 0.103 / 0.101 / 0.0018 / 1.018 / 0.032
hB-Fe(III)-1new / O3∙∙∙Fe / 0.033 / 0.154 / 0.036 / 0.037 / 0.0010 / 0.974 / 0.028
O4∙∙∙Fe / 0.031 / 0.148 / 0.035 / 0.036 / 0.0012 / 0.966 / 0.025
hB-Fe(III)-6 / C5∙∙∙Fe / 0.005 / 0.017 / 0.003 / 0.004 / 0.0004 / 0.898 / 7 x 10-4
hB-Fe(III)-3-an / O2∙∙∙Fe / 0.109 / 0.573 / 0.186 / 0.165 / 0.0213 / 1.129 / 0.081
O9∙∙∙Fe / 0.090 / 0.437 / 0.131 / 0.120 / 0.0109 / 1.091 / 0.067
hB-Fe(III)-1-an / O4∙∙∙Fe / 0.070 / 0.413 / 0.107 / 0.105 / 0.0017 / 1.016 / 0.029

Antioxidant and antimalarial properties of butein and homobutein based on their ability to chelate iron (II and III) cations: A DFT study in vacuo and in solution

European Food Research and Technology

Kemoabetswe. R. N. Serobatseand Mwadham. M. Kabanda*

Department of Chemistry, Faculty of Agriculture, Science and Technology, School of Mathematical and Physical Science, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa*

Table S2 B3LYP/6-31+G(d,p) results of the study in vacuo on the natural atomic orbital occupancies of some valence orbitals in the isolated Fen+cations and in a number of complexes with butien and homobutein

Isolated and Fe complex / Orbitals and the corresponding natural atomic orbital occupancies
S (4s) / dxy (3d) / dxz (3d) / dyz (3d) / dx2-y2 (3d) / dz2 (3d)
Fe(II) / 0.00001 / 1.99800 / 0.99980 / 0.99980 / 0.99996 / 0.99974
B-Fe(II)-1 / 0.10010 / 1.18779 / 1.24566 / 1.44790 / 1.49406 / 1.14068
B-Fe(II)-2 / 0.16355 / 1.23997 / 1.70612 / 1.19653 / 1.49096 / 1.25766
B-Fe(II)-3 / 0.08836 / 1.31997 / 1.50432 / 1.57800 / 1.41589 / 1.09770
B-Fe(II)-4 / 0.09112 / 1.23180 / 1.29626 / 1.56841 / 1.54379 / 1.28508
B-Fe(II)-1-an / 0.14003 / 1.19793 / 1.30628 / 1.82717 / 1.04403 / 1.02299
B-Fe(II)-2-an-a / 0.11986 / 1.04593 / 1.82323 / 1.03694 / 1.40543 / 1.36537
B-Fe(II)-2-an-b / 0.13113 / 1.09894 / 1.06096 / 1.15407 / 1.44109 / 1.83041
hB-Fe(II)-1 / 0.09925 / 1.54538 / 1.21950 / 1.34782 / 1.21467 / 1.21616
hB-Fe(II)-2 / 0.06508 / 1.13215 / 1.08783 / 1.20978 / 1.77214 / 1.72818
hB-Fe(II)-3 / 0.08836 / 1.27675 / 1.53776 / 1.53170 / 1.46640 / 1.10559
hB-Fe(II)-4 / 0.09106 / 1.18649 / 1.41423 / 1.67623 / 1.53548 / 1.11193
hB-Fe(II)-1-an / 0.13888 / 1.20178 / 1.83597 / 1.07831 / 1.15492 / 1.11436
hB-Fe(II)-2-an / 0.13091 / 1.23034 / 1.35018 / 1.78170 / 1.13416 / 1.17425
Fe(III) / 0.00002 / 1.00000 / 1.00000 / 1.00000 / 1.00000 / 1.00000
B-Fe(III)-1 / 0.09218 / 1.43397 / 1.13733 / 1.24028 / 1.38099 / 1.14817
B-Fe(III)-2 / 0.04976 / 1.16599 / 1.10134 / 1.28033 / 1.62952 / 1.45257
B-Fe(III)-3 / 0.13340 / 1.08332 / 1.83198 / 1.13446 / 1.33858 / 1.10191
B-Fe(III)-4 / 0.15379 / 1.14479 / 1.61265 / 1.11117 / 1.35224 / 1.38832
B-Fe(III)-1-an / 0.11768 / 1.18176 / 1.59874 / 1.50775 / 1.05931 / 1.02420
B-Fe(III)-2-an-a / 0.12238 / 1.06881 / 1.06570 / 1.36150 / 1.66987 / 1.27994
B-Fe(III)-2-an-b / 0.10773 / 1.46872 / 1.28563 / 1.14807 / 1.15753 / 1.39077
hB-Fe(III)-1 / 0.09388 / 1.73570 / 1.04492 / 1.25541 / 1.11507 / 1.18868
hB-Fe(III)-2 / 0.05821 / 1.11926 / 1.07666 / 1.23349 / 1.70756 / 1.48332
hB-Fe(III)-4 / 0.15836 / 1.16666 / 1.60826 / 1.07622 / 1.34789 / 1.41682
hB-Fe(III)-3 / 0.13074 / 1.10227 / 1.82742 / 1.15820 / 1.32347 / 1.08662
hB-Fe(III)-1-an / 0.17296 / 1.08586 / 1.14939 / 1.43047 / 1.54615 / 1.12937
hB-Fe(III)-2-an / 0.13372 / 1.35636 / 1.14334 / 1.17081 / 1.07797 / 1.70683