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2015 | 13 | 1 |
Tytuł artykułu

A theoretical antioxidant pharmacophore for natural hydroxycinnamic acids

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The structure-activity relationship analysis has been performed for trans- and cis-hydroxycinnamic acids, to determine their theoretical antioxidant pharmacophore. Based on the detailed conformational studies, the most stable rotamers have been selected. We have analyzed the descriptors of four antioxidant mechanisms important in free radical scavenging: hydrogen atom transfer, sequential proton loss electron transfer, single electron transfer - proton transfer and transition metal chelation, based on the B3LYP/6-311++G(2d,2p) calculations in vacuum and polar media. The results explain the activity difference between cinnamic acid and its derivatives. The descending order of antioxidant potential is as follows: caffeic > sinapinic ~ ferulic > p-coumaric > o-coumaric > m-coumaric ~ phenol. The results have shown that transisomers indicate higher reactivity than cis- and may be considered as good antioxidants. It has been determined that the highest antioxidant ability is related to the hydroxyl group in para position, supported by planar structure and stability of radical forms. π-Type delocalization of unpaired electron on aromatic ring, double bond and para O-atom is the key to radical stabilization. The ortho-dihydroxy substitution in benzene ring positively influences the ability to neutralize free radicals and makes caffeic acid the antioxidant pharmacophore of hydroxycinnamic acids.
EN
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
13
Numer
1
Opis fizyczny
Daty
wydano
2015-01-01
otrzymano
2014-02-02
zaakceptowano
2014-04-15
online
2014-10-28
Twórcy
  • Department of Human Molecular Genetics, Faculty of Biology, Adam Mickiewicz University, 61-614 Poznań, Poland
  • Department of Bioorganic Chemistry, Faculty of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland, au50380@st.amu.edu.pl
  • Department of Human Molecular Genetics, Faculty of Biology, Adam Mickiewicz University, 61-614 Poznań, Poland
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_1515_chem-2015-0001
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