Prooxidant activity of caffeic acid, dietary non‐flavonoid phenolic acid, on Cu<sup>2+</sup>‐induced low density lipoprotein oxidation

Yamanaka, Naoaki; Oda, Osamu; Nagao, Seiji

doi:10.1016/s0014-5793(97)00185-3

Cited by 101 publications

(54 citation statements)

References 28 publications

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“…Redox cycling of HCAs can be catalyzed by transition metals in the presence of oxygen, producing organic radicals along with ROS that may damage biological macromolecules [160].…”

Section: Pro-oxidant Effects Of Hydroxycinnamic Acidsmentioning

confidence: 99%

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

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Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxi-dant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the car-boxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activ-ity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimiza-tion of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be use-ful for management of oxidative stress-related diseases.Keywords: Antioxidant, hydroxycinnamic acids, in vitro, ROS, structure-activity relationships. OXIDATIVE STRESS AND ANTIOXIDANTSReactive oxygen species (ROS) are oxygen derived molecules that readily react with other compounds and macromolecules and oxidize them. Some representative exam-ples of these species include superoxide (O2•-), hydroxy (HO • ) and peroxy (ROO • ) radicals, hydrogen peroxide (H2O2) and singletROS are involved in important physiological processes such as immune response, gene expression, signal transduc-tion and growth regulation [5,6]; however if they are not kept under tight control by physiological antioxidant systems they will be able to oxidize and damage various biological molecules leading to a condition called oxidative stress [1,7,8]. In this regard, oxidative stress has been reported to be in-volved in the pathogenesis of diseases such as cancer [9], neurodegenerative diseases [10], stroke [11], and others [12,13].Since an important source of ROS comes from environment [14], with the industrial development and the change in life style, oxidative stress related diseases need a special attention [15].Antioxidants operate by preventing or slowing the progression of oxidative damage reactions [16,17]. An antioxidant has been defined as "any substance that delays, p...

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“…Redox cycling of HCAs can be catalyzed by transition metals in the presence of oxygen, producing organic radicals along with ROS that may damage biological macromolecules [160].…”

Section: Pro-oxidant Effects Of Hydroxycinnamic Acidsmentioning

confidence: 99%

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

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“…The phytoestrogens and their metabolites have many potent hormonal and non-hormonal activities that may explain some of the biological effects of diets rich in isoflavones (Mazur et al, 1998;Setchell, 1998;Song et al, 1999;Ren et al, 2001;Arjmandi & Smith, 2002). On the other hand, depending on the concentration and hydroxyl substituent pattern, phenolic compounds can also act as pro-oxidants (Laughton et al, 1989;Yamanaka et al, 1997;Metodiewa et al, 1999). Other negative physiological effects of flavonoids (mutagenicity, genotoxicity, cytotoxicity) have also been described (MacGregor & Jurd, 1978;Brown & Dietrich, 1979;Brown, 1980;Rueff et al, 1992;Yamanaka et al, 1997;Metodiewa et al, 1999;Hodek et al, 2002).…”

Section: Structure Classification Distribution Of Phenols In Plant mentioning

confidence: 99%

“…On the other hand, depending on the concentration and hydroxyl substituent pattern, phenolic compounds can also act as pro-oxidants (Laughton et al, 1989;Yamanaka et al, 1997;Metodiewa et al, 1999). Other negative physiological effects of flavonoids (mutagenicity, genotoxicity, cytotoxicity) have also been described (MacGregor & Jurd, 1978;Brown & Dietrich, 1979;Brown, 1980;Rueff et al, 1992;Yamanaka et al, 1997;Metodiewa et al, 1999;Hodek et al, 2002). Most of these physiological effects are based on either in vitro models, cell/tissue culture studies, animal experiments or epidemiological data.…”

Section: Structure Classification Distribution Of Phenols In Plant mentioning

confidence: 99%

Reactions of Plant Phenolics with Food Proteins and Enzymes under Special Consideration of Covalent Bonds

Kröll

Rawel

Rohn

2003

FSTR

336

273

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Secondary plant metabolites are important native food components, which are becoming more and more interesting due to their physiological effects on human beings. One of the largest groups of these compounds is represented by plant phenols. This review summarizes the structure, classification and distribution of the phenolic compounds in plant foods, their chemistry and signification with regard to food processing and -storage as well as their physiological effects. This work focuses mainly on such reactions of the phenolic substances with proteins and enzymes that lead to covalent bonds. The derivatives formed have been characterized in terms of changes in their physicochemical and structural properties. The effect on the proteolytic in vitro digestion has been also illustrated. Further aspects reported include the influence on enzyme activity and -kinetic parameters. The different aspects of the nutritional-physiological consequences of such reactions in food and body, especially considering their significance to food science and technology are discussed.

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“…It is not known whether this mechanism can occur with other classical antioxidants, such as uric acid, although evidence has been obtained indicating that free radical metabolites originate from the oxidation of uric acid [17] and that the combination of Cu(II) and uric acid may promote oxidative DNA breakage [18]. Moreover, studies performed with other water-soluble antioxidants, such as Trolox C [19], ascorbic acid [20], caffeic acid [21] and green tea cathechins [22], have revealed that these compound may act either as antioxidants or pro-oxidants during copper-mediated LDL oxidation.…”

Section: Introductionmentioning

confidence: 99%

When and why a water-soluble antioxidant becomes pro-oxidant during copper-induced low-density lipoprotein oxidation: a study using uric acid

Bagnati

Perugini

Cau

et al. 1999

Biochemical Journal

135

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The inclusion of uric acid in the incubation medium during copper-induced low-density lipoprotein (LDL) oxidation exerted either an antioxidant or pro-oxidant effect. The pro-oxidant effect, as mirrored by an enhanced formation of conjugated dienes, lipid peroxides, thiobarbituric acid-reactive substances and increase in negative charge, occurred when uric acid was added late during the inhibitory or lag phase and during the subsequent extensive propagation phase of copper-stimulated LDL oxidation. The pro-oxidant effect of uric acid was specific for copper-induced LDL oxidation and required the presence of copper as either Cu(I) or Cu(II). In addition, it became much more evident when the copper to LDL molar ratio was below a threshold value of approx. 50. In native LDL, the shift between the antioxidant and the pro-oxidant activities was related to the availability of lipid hydroperoxides formed during the early phases of copper-promoted LDL oxidation. The artificial enrichment of isolated LDL with α-tocopherol delayed the onset of the pro-oxidant activity of uric acid and also decreased the rate of stimulated lipid peroxidation. However, previous depletion of α-tocopherol was not a prerequisite for unmasking the pro-oxidant activity of uric acid, since this became apparent even when α-tocopherol was still present in significant amounts (more than 50% of the original values) in LDL. These results suggest, irrespective of the levels of endogenous α-tocopherol, that uric acid may enhance LDL oxidation by reducing Cu(II) to Cu(I), thus making more Cu(I) available for subsequent radical decomposition of lipid peroxides and propagation reactions.

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Prooxidant activity of caffeic acid, dietary non‐flavonoid phenolic acid, on Cu²⁺‐induced low density lipoprotein oxidation

Abstract: © 1997 Federation of European Biochemical Societies.

Cited by 101 publications

References 28 publications

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Reactions of Plant Phenolics with Food Proteins and Enzymes under Special Consideration of Covalent Bonds

When and why a water-soluble antioxidant becomes pro-oxidant during copper-induced low-density lipoprotein oxidation: a study using uric acid

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Prooxidant activity of caffeic acid, dietary non‐flavonoid phenolic acid, on Cu2+‐induced low density lipoprotein oxidation

Abstract: © 1997 Federation of European Biochemical Societies.

Cited by 101 publications

References 28 publications

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Reactions of Plant Phenolics with Food Proteins and Enzymes under Special Consideration of Covalent Bonds

When and why a water-soluble antioxidant becomes pro-oxidant during copper-induced low-density lipoprotein oxidation: a study using uric acid

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Prooxidant activity of caffeic acid, dietary non‐flavonoid phenolic acid, on Cu²⁺‐induced low density lipoprotein oxidation