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| Research article summary (published 24 Nov 2008): |
New lipophilic tyrosyl esters. Comparative antioxidant evaluation with hydroxytyrosyl esters.
Full Abstract
New lipophilic esters of tyrosol, a naturally occurring phenol with interesting biological properties, have been synthesized in good yields by a chemoselective procedure, using lipase from Candida antarctica or p-toluenesulfonic acid as catalysts. Their antioxidant activities have been evaluated by the Rancimat test in lipophilic food matrices, as well as by FRAP and ABTS assays in methanolic solutions, and compared with those of previously synthesized hydroxytyrosyl esters. Free tyrosol, hydroxytyrosol, butylhydroxytoluene, and alpha-tocopherol were used as standards. All methods used for the antioxidant activity evaluation emphasized the high influence of the ortho-diphenolic structure on the antioxidant capacity, tyrosol and its derivatives being less active than hydroxytyrosol and its analogues and even less than BHT and alpha-tocopherol. In addition, the Rancimat test revealed a lower activity for ester derivatives than for their respective reference compounds (HTy or Ty), in agreement with the polar paradox. On the other hand, FRAP and ABTS methods reported an opposite behavior between the synthetic esters and their respective references. Thus, hydroxytyrosyl esters were more active than HTy, whereas tyrosyl esters were less active than Ty. The length and nature of the acyl side chain did not seem to play an important role in the antioxidant activity of either the hydroxytyrosyl or tyrosyl ester series, since no significant differences were observed among them.
Author information
Author/s: Mateos, Raquel (R); Trujillo, Mariana (M); Pereira-Caro, Gema (G); Madrona, Andrés (A); Cert, Arturo (A); Espartero, José Luis (JL);
Affiliation: IFAPA, Centro Venta de Llano, Mengibar, Jaen, Spain. mariar.mateos(-atsign-)juntadeandalucia.es
Journal and publication information
Publication Type: Comparative Study; Journal Article; Research Support, Non-U.S. Gov't
Journal: Journal of agricultural and food chemistry (J Agric Food Chem), published in United States. (Language: eng)
Reference: 2008-Nov; vol 56 (issue 22) : pp 10960-6
Dates: Created 2009/02/20; Completed 2009/04/03;
PMID: 18983160, status: MEDLINE (last retrieved date: 4/3/2009)
Sourced from the National Library of Medicine. Abstract text and other information may be subject to copyright.
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Associated Chemicals: Antioxidants (0) ; Benzenesulfonates (0) ; Benzothiazoles (0) ; Esters (0) ; Ferric Compounds (0) ; Sulfonic Acids (0) ; 4-toluenesulfonic acid (104-15-4) ; 3,4-dihydroxyphenylethanol (10597-60-1) ; 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid (28752-68-3) ; 4-hydroxyphenylethanol (501-94-0) ; Phenylethyl Alcohol (60-12-8) ; Lipase (EC 3.1.1.3)Related articles
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