Elucidation of hydroxyl groups-antioxidant relationship in mono- and dihydroxyflavones based on O-H bond dissociation enthalpies
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| 024 | 7 | 0 | |a 10.1007/s00894-015-2669-2 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2669-2 | ||
| 245 | 0 | 0 | |a Elucidation of hydroxyl groups-antioxidant relationship in mono- and dihydroxyflavones based on O-H bond dissociation enthalpies |h [Elektronische Daten] |c [Witcha Treesuwan, Songwut Suramitr, Supa Hannongbua] |
| 520 | 3 | |a Radical scavenging potential is the key to anti-oxidation of hydroxyflavones which generally found in fruits and vegetables. The objective of this work was to investigate the influence of hydroxyl group on the O-H bond dissociation enthalpies (BDE) from a series of mono- and dihydroxyflavones. Calculation at the B3LYP/6-31G(d,p) level reveals the important roles of an additional one hydroxyl group to boost the BDE of hydroxyflavones that were a stabilization of the generated radicals through attractive H-bond interactions, an ortho- and para-dihydroxyl effect, and a presence of the 3-OH in dihydroxyflavones. On the other hand, the meta-dihydroxyl effect and range-hydroxyl effect especially associated with the either 5-OH or 8-OH promoted greater BDE. Results did not only confirm that dihydroxyflavones had lower BDE than monohydroxyflavones but also suggest the selective potent hydroxyflavone molecules that are the 6′-hydroxyflavone (for monohydroxyflavone) and the 5′,6′-, 7,8- and 3′,4′-dihydroxyflavone which the corresponding radical preferable generated at C6′-O•, C8-O• and C4′-O•, respectively. Electron distribution was limited only over the two connected rings of hydroxyflavones while the expansion distribution into C-ring could be enhanced if the radical was formed especially for the 2′,3′- and 5′,6′dihydroxyflavone radicals. The delocalized bonds were strengthened after radical was generated. However the 5-O• in 5,6-dihydroxyflavone and the 3-O• in 3,6′-dihydroxyflavone increased the bond order at C4-O11 which might interrupt the conjugated delocalized bonds at the keto group. Graphical Abstract This work suggests that a preferable region of the catechol group in dihydroxyflavones was selective. The 5′,6′-, 7,8-, and 3′,4′-dihydroxyflavone, which had the corresponding radical at C6′-O•, C8-O• and C4′-O•, shows higher potential of H-atom donation than others. | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a Functional food |2 nationallicence | |
| 690 | 7 | |a Antioxidant |2 nationallicence | |
| 690 | 7 | |a Hydroxyflavone |2 nationallicence | |
| 690 | 7 | |a DFT |2 nationallicence | |
| 690 | 7 | |a Bond dissociation enthalpy |2 nationallicence | |
| 700 | 1 | |a Treesuwan |D Witcha |u Institute of Food Research and Product Development, Kasetsart University, 10900, Bangkok, Thailand |4 aut | |
| 700 | 1 | |a Suramitr |D Songwut |u Department of Chemistry, Faculty of Science, Kasetsart University, 10900, Bangkok, Thailand |4 aut | |
| 700 | 1 | |a Hannongbua |D Supa |u Department of Chemistry, Faculty of Science, Kasetsart University, 10900, Bangkok, Thailand |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/6(2015-06-01), 1-10 |x 1610-2940 |q 21:6<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2669-2 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2669-2 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Treesuwan |D Witcha |u Institute of Food Research and Product Development, Kasetsart University, 10900, Bangkok, Thailand |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Suramitr |D Songwut |u Department of Chemistry, Faculty of Science, Kasetsart University, 10900, Bangkok, Thailand |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Hannongbua |D Supa |u Department of Chemistry, Faculty of Science, Kasetsart University, 10900, Bangkok, Thailand |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/6(2015-06-01), 1-10 |x 1610-2940 |q 21:6<1 |1 2015 |2 21 |o 894 | ||