Characterization of nitrated phenolic compounds for their anti-oxidant, pro-oxidant, and nitration activities

Iwasaki, Yusuke; Nomoto, Maki; Oda, Momoko; Mochizuki, Kimihiro; Nakano, Yüki; Ishii, Yuji; Ito, Rie; Saito, Koichi; Umemura, Takashi; Nishikawa, Akiyoshi; Nakazawa, Hiroyuki

doi:10.1016/j.abb.2011.06.009

Cited by 7 publications

(9 citation statements)

References 28 publications

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“…Iwasaki et al [132] synthesized a nitrated chlorogenic acid (CGA) and demonstrated that it had stronger antioxidant activity than non-nitrated CGA. The observed effects were attributed to the higher ability of nitrocatechol derivatives in sequestering chelated iron compared to catechol.…”

Section: Introduction Of Electron Withdrawing Substituentsmentioning

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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Section: Introduction Of Electron Withdrawing Substituentsmentioning

confidence: 99%

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

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

View full text Add to dashboard Cite

show abstract

“…In order to prevent the formation of oxidative by-products during DNA isolation, DNA was digested by using a slightly modification of our previous method 3), 4) . Calf thymus DNA (2 mg/mL, 0.4 mL) was incubated at 40 for 30 min after addition of 0.05 mL of antioxidant Table 1.…”

Section: Dna Digestion and Determination Of Dg And 8-ohdgmentioning

confidence: 99%

“…The ESR method was used for the determination of hydroxyl radicals ( • OH) 3), 4) . 3 was carried out with an ESR spectrometer (JES-RE1X, JEOL Co., Tokyo, Japan).…”

Section: Electron Spin Resonance Measurement Of Hydroxyl Radicalmentioning

confidence: 99%

“…The modified DPPH method was used for determination of antioxidant activity 3), 4) . DPPH radical solution were calculated from the inhibition percentage.…”

Section: Dpph Radical-scavenging Activitymentioning

confidence: 99%

“…Caffeic acid (CaA), a phenolic compound, reacted with sodium nitrite in artificial gastric juice, forming new products via generation of reactive nitrogen species (RNS) 4) . Antioxidants are added to many foods to prevent the degradation of food components and degradation or fading of food colors.…”

Section: Introductionmentioning

confidence: 99%

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Generation of Reactive Oxygen Species by Interaction between Antioxidants Used as Food Additive and Metal Ions

Iwasaki

Oda²,

Tsukuda³

et al. 2014

Journal of the Food Hygienics Society of Japan

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Food additives, such as preservatives, sweeteners, coloring agents, and flavoring agents, are widely used in food manufacturing. However, their combined effects on the human body are not known. The purpose of this study was to examine whether combinations of antioxidants and metal ions generate reactive oxygen species (ROS) under in vitro conditions using electron spin resonance (ESR). Among the metal ions examined, only iron and copper generated ROS in the presence of antioxidants. Moreover, certain phenolic antioxidants having pro-oxidant activity induced DNA oxidation and degradation via the generation of high levels of ROS in the presence of copper ion, resulting in complete degradation of DNA in vitro.

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Combined use of a probiotic culture and citrus fiber in a traditional sausage ‘Longaniza de Pascua’

et al. 2012

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Characterization of nitrated phenolic compounds for their anti-oxidant, pro-oxidant, and nitration activities

Cited by 7 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

Generation of Reactive Oxygen Species by Interaction between Antioxidants Used as Food Additive and Metal Ions

Combined use of a probiotic culture and citrus fiber in a traditional sausage ‘Longaniza de Pascua’

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