Structure-antioxidant activity relationship study of natural hydroxybenzaldehydes using in vitro assays

被引:45
作者
Bountagladou, Olga G. [1 ]
Ordoudi, Stella A. [1 ]
Tsunidou, Maria Z. [1 ]
机构
[1] Anstotle Univ Thessaloniki, Dept Chem, Lab Food Chem & Technol, Thessaloniki 54124, Greece
关键词
Hydroxybenzaldehydes; Structure-activity relationship; Phenolic antioxidants; CBA; DPPH; ABTS; Rancimat; SCAVENGING ACTIVITY; 2-SUBSTITUTED PHENOLS; ACID-DERIVATIVES; BENZOIC-ACIDS; INHIBITION; OXIDATION; ENTHALPIES; PARAMETERS; CONSTANTS; PRODUCTS;
D O I
10.1016/j.foodres.2010.05.021
中图分类号
TS2 [食品工业];
学科分类号
0832 ;
摘要
Structure-activity relationships (SARs) were sought among protocatechuic aldehyde 1 syringaldehyde 2 vanillin 3 p-hydroxybenzaldehyde 4 and salicylaldehyde 5 using various in vitro antioxidant assays (crocin bleaching assay ABTS DPPH Rancimat and liposomes) These aldehydes are known to contribute to the evolution of flavor during aging of alcoholic beverages in wood barrels and as natural preservatives Their acid counterparts (1'-5') were also studied for comparison The non-substituted hydroxybenzaldehydes (4 5) and the respective acids showed negligible activity under the CBA DPPH and the accelerated bulk oil oxidation conditions so that no SAR could be drawn The only compound that exhibited high antioxidant activity equal or even higher than 1 in all assay environments was 1 Syringaldehyde was found to possess exceptionally high activity in comparison to 2' only under the CBA conditions Moreover 1 and 2 were found to be strong inhibitors of bulk oil or of lecithin liposome oxidation Our findings add to knowledge about the antioxidant activity of the particular aldehydes apart from their flavoring and antibacterial properties (C) 2010 Elsevier Ltd All rights reserved
引用
收藏
页码:2014 / 2019
页数:6
相关论文
共 34 条
[1]   A critical appraisal of the use of the antioxidant capacity (TEAC) assay in defining optimal antioxidant structures [J].
Arts, MJTJ ;
Dallinga, JS ;
Voss, HP ;
Haenen, GRMM ;
Bast, A .
FOOD CHEMISTRY, 2003, 80 (03) :409-414
[2]  
Barberan FA, 2000, J SCI FOOD AGR, V80, P1024
[3]   Comparative evaluation of the antioxidant capacity of smoke flavouring phenols by crocin bleaching inhibition, DPPH radical scavenging and oxidation potential [J].
Bortolomeazzi, Renzo ;
Sebastianutto, Nerina ;
Toniolo, Rosanna ;
Pizzariello, Andrea .
FOOD CHEMISTRY, 2007, 100 (04) :1481-1489
[4]  
BRAND-WILLIAMS W, 1995, FOOD SCI TECHNOL-LEB, V28, P25
[5]  
BROTO P, 1984, EUR J MED CHEM, V19, P71
[6]   COMPARISON OF THE ANTIOXIDATIVE ACTIVITY OF SOME ACID-PHENOLS - STRUCTURE ACTIVITY RELATIONSHIP [J].
CUVELIER, ME ;
RICHARD, H ;
BERSET, C .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1992, 56 (02) :324-325
[7]   Inhibition of methyl linoleate autoxidation by phenolics and other related compounds under mild oxidative conditions [J].
Dávalos, A ;
Bartolomé, B ;
Gómez-Cordovés, C .
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 2004, 84 (07) :631-638
[8]   Structure-function analysis of the vanillin molecule and its antifungal properties [J].
Fitzgerald, DJ ;
Stratford, M ;
Gasson, MJ ;
Narbad, A .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (05) :1769-1775
[9]  
FRANKEL NE, 2007, ANTIOXIDANTS FOOD BI, P6
[10]   Antibacterial activities of phenolic benzaldehydes and benzoic acids against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica [J].
Friedman, M ;
Henika, PR ;
Mandrell, RE .
JOURNAL OF FOOD PROTECTION, 2003, 66 (10) :1811-1821