Antiradical and reductant activities of anthocyanidins and anthocyanins, structure-activity relationship and synthesis

被引:109
作者
Ali, Hussein M. [1 ]
Almagribi, Wafaa [2 ]
Al-Rashidi, Mona N. [2 ]
机构
[1] Ain Shams Univ, Fac Agr, Dept Agr Biochem, Cairo, Egypt
[2] Dammam Univ, Dept Chem, Fac Sci Girls, Dammam, Saudi Arabia
关键词
Anthocyanins; Antioxidants; SAR; Radical stabilization; Semiquinone resonance; ANTIOXIDANT ACTIVITY; PHENOLIC-COMPOUNDS; HYDROXYL; CAPACITY; ENTHALPIES; CHEMISTRY;
D O I
10.1016/j.foodchem.2015.09.003
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Eight anthocyanidins, seven anthocyanins and two synthesized 4'-hydroxy flavyliums were examined as hydrogen donors to DPPH, ABTS and hydroxyl radicals, and as electron donors in the FRAP assay. Most compounds gave better activities than trolox and catechol. A structure-activity relationship (SAR) study showed that, in the absence of the 3-OH group, radicals of the 4, 5 or 7-OH groups can only be stabilized by resonance through pyrylium oxygen, while 3-OH group improved hydrogen atom donation because of the stabilization by anthocyanidin semiquinone-like resonance. Electron donation was also enhanced by the 3-OH group. Both anthocyanidins and their respective anthocyanins showed similar trends and close activities. Different types of sugar unit bonded to the 3-OH group or counter ion had minor effect on activities. The catechol structure improved both hydrogen and electron donation. Compounds lacking the catechol structure had a decreasing order of H-atom and electron donation (Mv > Pn > Pg > Ap > 4'-OH-flavylium) consistent with the decreasing number of their hydroxyl and/or methoxy groups. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1275 / 1282
页数:8
相关论文
共 31 条
[1]   QSAR and mechanisms of radical scavenging activity of phenolic and anilinic compounds using structural, electronic, kinetic, and thermodynamic parameters [J].
Ali, Hussein M. ;
Ali, Isra H. .
MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (03) :987-998
[2]   Structural features, kinetics and SAR study of radical scavenging and antioxidant activities of phenolic and anilinic compounds [J].
Ali, Hussein M. ;
Abo-Shady, Ahmed ;
Eldeen, Hany A. Sharaf ;
Soror, Hany A. ;
Shousha, Wafaa G. ;
Abdel-Barry, Osama A. ;
Saleh, Ahmed M. .
CHEMISTRY CENTRAL JOURNAL, 2013, 7
[3]   The hydrophilic and lipophilic contribution to total antioxidant activity [J].
Arnao, MB ;
Cano, A ;
Acosta, M .
FOOD CHEMISTRY, 2001, 73 (02) :239-244
[4]   Antioxidant properties of anthocyanidins, anthocyanidin-3-glucosides and respective portisins [J].
Azevedo, Joana ;
Fernandes, Iva ;
Faria, Ana ;
Oliveira, Joana ;
Fernandes, Ana ;
de Freitas, Victor ;
Mateus, Nuno .
FOOD CHEMISTRY, 2010, 119 (02) :518-523
[5]   Phenolic compounds in plants and agri-industrial by-products: Antioxidant activity, occurrence, and potential uses [J].
Balasundram, Nagendran ;
Sundram, Kalyana ;
Samman, Samir .
FOOD CHEMISTRY, 2006, 99 (01) :191-203
[6]  
Bendary E., 2013, Annals of Agricultural Science (Cairo), V58, P173, DOI 10.1016/j.aoas.2013.07.002
[7]   The ferric reducing ability of plasma (FRAP) as a measure of ''antioxidant power'': The FRAP assay [J].
Benzie, IFF ;
Strain, JJ .
ANALYTICAL BIOCHEMISTRY, 1996, 239 (01) :70-76
[8]   Antioxidant capacity of a 3-deoxyanthocyanidin from soybean [J].
Boveris, AD ;
Galatro, A ;
Sambrotta, L ;
Ricco, R ;
Gurni, AA ;
Puntarulo, S .
PHYTOCHEMISTRY, 2001, 58 (07) :1097-1105
[9]  
BRAND-WILLIAMS W, 1995, FOOD SCI TECHNOL-LEB, V28, P25
[10]   Chemical studies of anthocyanins: A review [J].
Castaneda-Ovando, Araceli ;
de Lourdes Pacheco-Hernandez, Ma ;
Elena Paez-Hernandez, Ma. ;
Rodriguez, Jose A. ;
Andres Galan-Vidal, Carlos .
FOOD CHEMISTRY, 2009, 113 (04) :859-871