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 observed for caffeic acid (1) derivatives. The n-alkyl esters of both phenolic series had similar potencies, and their antiradical activities were independent of the alkyl chain length. Dose-dependent scavenger effects were found in both series. Acid-base properties of the compounds, evaluated by using potentiometry and spectrophotometry, showed that the catechol moiety had pK(a2) and pK(a3) values of 9. 24-9.02 and 11.38-10.99 in the dihydrocaffeic series and 8.48-8.24 and 11.38-11.07 in the caffeic series, respectively. Antiradical activity and pK(a) values of the compounds were not related.
Recebido em 21/11/97; aceito em 17/4/98 METHODS FOR THE EVALUATION OF THE DEGREE OF LIPID OXIDATION AND THEANTIOXIDANT ACTIVITY. In this work several methods for evaluation of the degree of lipid oxidation and antioxidant activity are reviewed. Some aspects related to the recent advances mentioned in the literature are also reported.Keywords: lipid oxidation; antioxidant activity; analytical methods. REVISÃO INTRODUÇÃOOs lipídios desempenham um importante papel no que respeita à qualidade de certos produtos alimentares, particularmente em relação às propriedades organolépticas que os tornam desejáveis (e.g. flavor, cor, textura). Por outro lado, conferem valor nutritivo aos alimentos, constituindo uma fonte de energia metabólica, de ácidos graxos essenciais (e.g. ácidos linoleíco, linolênico e araquidónico) e de vitaminas lipossolú-veis (e.g. A, D, E e K) 2 .A oxidação lipídica é um fenômeno espontâneo e inevitá-vel, com uma implicação direta no valor comercial quer dos corpos graxos, quer de todos os produtos que a partir deles são formulados (e.g. alimentos , cosméticos, medicamentos).A peroxidação lipídica constitui a principal causa de deterioração dos corpos graxos (lipídios e matérias graxas). Afastados do seu contexto de proteção natural, os corpos graxos sofrem, no decurso de processos de transformação e armazenamento, alterações do tipo oxidativo, as quais tem como principal conseqüência a modificação do flavor original e o aparecimento de odores e gostos característicos do ranço, o qual representa para o consumidor, ou para o transformador industrial, uma importante causa de depreciação ou rejeição 3 .Nos últimos anos, a preocupação constante de proporcionar aos consumidores produtos de alta qualidade levou à adoção de medidas que permitem limitar o fenômeno de oxidação durante as fases de processamento e armazenagem dos produtos (e.g. escolha de processos que limitem as operações de arejamento e o tratamento térmico; utilização de matérias-primas refinadas, com baixos teores de água e isentas de pró-oxidantes; armazenamento a baixas temperaturas e em atmosfera inerte; adição de compostos antioxidantes; utilização de embalagens estanques e opacas à radiação UV, etc.). Deste conjunto de ações, a adição de compostos antioxidantes é, sem dúvida, uma prática corrente, razão que justifica o atual interesse pela pesquisa de novos compostos com capacidade antioxidante. O baixo custo de obtenção, facilidade de emprego, eficácia, termo-resistência, "neutralidade" organoléptica e ausência reconhecida de toxicidade, são premissas para a sua seleção e utilização a nível industrial 3 . Neste contexto, torna-se necessário, por um lado controlar a qualidade dos corpos graxos, através da determinação do seu grau de oxidação e, por outro avaliar, a capacidade antioxidante de novos compostos. A grande diversidade de métodos analíticos (químicos, físicos e/ou físico-químicos) propostos na literatura para a avaliação do grau de oxidação lipídica e da capacidade antioxidante coloca, na prática, algumas dificuldades de sele...
The oxidative stability of refined sunflower oil in the presence and in the absence of propyl caffeate (PC), propyl hydrocaffeate (PHC), propyl ferulate (PF), and propyl isoferulate (PI) has been evaluated according to the Rancimat method. The antioxidant activity of the phenolic derivatives was compared with that obtained with native [alpha-tocopherol (alpha-TOH)] and synthetic [propyl gallate (PG)] antioxidants. The results allow the establishment of a decreasing order of antioxidant power: PG > PHC > PC >> alpha-TOH > PI > PF. The oxidative stability was improved neither by the addition of PF nor by a supplement of alpha-TOH. Moreover, a positive antioxidant effect was obtained for PC that was placed between those of alpha-TOH and PG. The antioxidant activity of PHC was higher than that of its analogue (PC). A dose-dependent effect was observed for PG, PHC, and PC. A chain-breaking mechanism was proposed for the antioxidant activity of propyl phenolic esters because the same ranking order of efficacy was obtained for their antiradical activities evaluated by using the 2,2-diphenyl-1-picrylhydrazyl radical method.
Fifty-nine xanthones ( 9H-xanthen-9-ones) of natural or synthetic origin were investigated for their inhibitory activity toward monoamine-oxidase A (MAO-A) and MAO-B. The compounds demonstrated reversible, time-independent activities, with selectivity toward MAO-A. The most active inhibitor had an IC 50 of 40 nm. Electron absorption spectroscopy revealed the formation of a 1 : 1 charge-transfer complex between lumiflavine and xanthones. 3D-QSAR Studies according to the CoMFA/GOLPE procedure provided information on the relationship between steric and electrostatic fields and MAO-A inhibition. The ALMOND procedure yielded additional topographical information on structural factors favoring activity.
In recent years, much attention has been given to dietary antioxidants, especially polyphenols. Several peptides derived from protein molecules have also been found to show antioxidant capacity along with other biological properties and thus there is an increasing interest in these compounds as health promoters. This review summarizes and discusses the main sources of antioxidative peptides with focus on food-derived peptides (animal, plant and marine sources), methods of preparation, antioxidant capacity evaluation as well as their proposed mechanisms of action. A discussion of the potential health effects and comments on the different applications for these antioxidants and their potential research interest are also subject of this review.
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