2000
DOI: 10.1021/jf9913110
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Abstract: The antiradical activity of caffeic acid (1), dihydrocaffeic acid (5), and their corresponding n-alkyl esters was evaluated by using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(*)) method. Dihydrocaffeic acid (5) was the most potent compound, having an antiradical effect higher than that of (+/-)-alpha-tocopherol, whereas caffeic acid (1) was less efficient. Esterification of the carboxyl group of dihydrocaffeic acid (5) had a dramatic effect on its antiradical potency, but similar effects were not observe… Show more

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Cited by 345 publications
(241 citation statements)
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“…as antimicrobial agents that weaken the outer membrane of the cells, inducing changes on its permeability and, consequently, in the bacterial physicochemical characteristics. 63,64 It is possible that the antimicrobial activity of alkyl caffeates is associated with a fine balance between affinity for the lipid bilayers of cell membranes and the ability to cause disruption of the membrane, which visibly differs from Gram-positive to Gram-negative bacteria (due to their different cell wall structure and composition) and is dependent on the length of the alkyl ester side chain. Therefore, it is proposed that in Gram-negative bacteria, smaller length alkyl ester chains might have a better lipophilicity balance, and thus, be more effective in crossing the LPS layer of the outer membrane.…”
Section: Effects Of Caffeic Acid and Its Alkyl Esters On The Cell Memmentioning
confidence: 99%
“…as antimicrobial agents that weaken the outer membrane of the cells, inducing changes on its permeability and, consequently, in the bacterial physicochemical characteristics. 63,64 It is possible that the antimicrobial activity of alkyl caffeates is associated with a fine balance between affinity for the lipid bilayers of cell membranes and the ability to cause disruption of the membrane, which visibly differs from Gram-positive to Gram-negative bacteria (due to their different cell wall structure and composition) and is dependent on the length of the alkyl ester side chain. Therefore, it is proposed that in Gram-negative bacteria, smaller length alkyl ester chains might have a better lipophilicity balance, and thus, be more effective in crossing the LPS layer of the outer membrane.…”
Section: Effects Of Caffeic Acid and Its Alkyl Esters On The Cell Memmentioning
confidence: 99%
“…Several flavonoid compounds (Lewis & Mabrry, 1972;Williams, 1978;Williams & Harbone, 1988;Yano, 1998Yano, ,2003, anthocyanins (Saito & Harbone, 1983;Scogin, 1985), esters of arylpropanoid acid derivatives (Sutherland & Gortner, 1959;Takata & Scheuer, 1976;Rocha, 1999) have been related to Bromeliaceae species. These types of compounds are known as possessing antioxidant and antiradical activities (Graf, 1992;Cotelle et al, 1996;Rice-Evans et al, 1996, Pietta, 2000Silva et al, 2000). Antioxidant compounds protect the biological system against the potentially harmful effect of processes or reactions that cause excessive oxidation, involving reactive oxygen (and nitrogen) species (RONS).…”
Section: Introductionmentioning
confidence: 99%
“…However, the antioxidant activity of plant extracts may relate to the presence of some individual phenolic compounds and their structures [24]. In addition, the position and quantitation of hydroxyl groups are possibly one of the main factors [38]. If an additional hydroxyl group is added to ortho or para position of the benzen ring, the antioxidant activity will be significantly increased, principally the ortho position can create the intramolecular hydrogen bond, so such position is proposed more effective than para and meta one [39,40].…”
mentioning
confidence: 99%