free radicals natural antioxidants and their reaction mechanisms

free radicals natural antioxidants and their reaction mechanisms

The other way of categorizing the antioxidants is based on their solubility in the water or lipids. The antioxidants can be categorized as water-soluble and lipid-soluble antioxidants. The water-soluble antioxidants e.

The lipid-soluble antioxidants e. The antioxidants can also be categorized according to their size, the small-molecule antioxidants and large-molecule antioxidants. The small-molecule antioxidants neutralize the ROS in a process called radical scavenging and carry them away. To understand the mechanism of action of antioxidants, it is necessary to understand the generation of free radicals and their damaging reactions. This review elaborates the generation and damages that free radicals create, mechanism of action of the natural antioxidant compounds and assays for the evaluation of their antioxidant properties.

The reaction mechanisms of the antioxidant assays are discussed. The scope of this article is limited to the natural antioxidants and the in vitro assays for evaluation of their antioxidant properties. These ROS can act by either of the two oxygen dependent mechanisms resulting in the destruction of the microorganism or other foreign matter.

The reactive species can also be generated by the myeloperoxidase—halide—H 2 O 2 system. The enzyme myeloperoxidase MPO is present in the neutrophil cytoplasmic granules.

In presence of the chloride ion, which is ubiquitous, H 2 O 2 is converted to hypochlorous HOCl, eqn 3 , a potent oxidant and antimicrobial agent. Peroxynitrite reacts with the aromatic amino acid residues in the enzyme resulting in the nitration of the aromatic amino acids. Such a change in the aminoacid residue can result in the enzyme inactivation. However, nitric oxide is an important cytotoxic effector molecule in the defense against tumor cells, various protozoa, fungi, helminthes, and mycobacteria.

The peroxyl radicals are the carriers of the chain reactions. Among them, at the physiological level, is a microvascular system with the function of maintaining the levels of O 2 in the tissues, and at a biochemical level, the antioxidant defense can be enzymatic or nonenzymatic, as well as being a system for repairing molecules.

SOD is the most important and most powerful detoxification enzyme in the cell. SOD is a metalloenzyme and, therefore, requires a metal as a cofactor for its activity. Depending on the type of metal ion required as a cofactor by SOD, there are several forms of the enzyme [ 12 , 13 ]. CAT uses iron or manganese as a cofactor and catalyzes the degradation or reduction of hydrogen peroxide H 2 O 2 to produce water and molecular oxygen, thus completing the detoxification process initiated by SOD [ 14 , 15 ].

CAT is highly efficient at breaking down millions of H 2 O 2 molecules in a second. CAT is mainly found in peroxisomes, and its main function is to eliminate the H 2 O 2 generated during the oxidation of fatty acids. GPx is an important intracellular enzyme that breaks down H 2 O 2 in water and lipid peroxides in their corresponding alcohols; this happens mainly in the mitochondria and sometimes in the cytosol [ 16 ].

The activity of GPx depends on selenium. Among glutathione peroxidases, GPx1 is the most abundant selenoperoxidase and is present in virtually all cells. The enzyme plays an important role in inhibiting the process of lipid peroxidation and, therefore, protects cells from oxidative stress [ 18 ].

Low GPx activity leads to oxidative damage of the functional proteins and the fatty acids of the cell membrane. GPx, particularly GPx1, has been implicated in the development and prevention of many diseases, such as cancer and cardiovascular diseases [ 19 ]. DT-diaphorase catalyzes the reduction of quinone to quinol and participates in the reduction of drugs of quinone structure [ 20 ]. DNA regulates the production of these enzymes in cells.

This system of antioxidants consists of antioxidants that trap FR. They capture FR to avoid the radical initiation reaction. Neutralize the radicals or capture them by donating electrons, and during this process, the antioxidants become free radicals, but they are less reactive than the initial FR. FR from antioxidants are easily neutralized by other antioxidants in this group. The flavonoids that are extracted from certain foods interact directly with the reactive species to produce stable complexes or complexes with less reactivity, while in other foods, the flavonoids perform the function of co-substrate in the catalytic action of some enzymes.

Enzymes that repair or eliminate the biomolecules that have been damaged by ROS, such as lipids, proteins, and DNA, constitute the repair systems. Common examples include systems of DNA repair enzymes polymerases, glycosylases, and nucleases and proteolytic enzymes proteinases, proteases, and peptidases found in both the cytosol and the mitochondria of mammalian cells.

These enzymes act as intermediaries in the repair process of the oxidative damage caused by the attack of excess ROS. Any environmental factor that inhibits or modifies a regular biological activity becomes a condition that favors the appearance or reinforcement of oxidative stress.

The main characteristic of a compound or antioxidant system is the prevention or detection of a chain of oxidative propagation, by stabilizing the generated radical, thus helping to reduce oxidative damage in the human body [ 21 ]. Gordon [ 22 ] provided a classification of antioxidants, mentioning that characteristic. There are two main types of antioxidants, the primary breaking the chain reaction, free radical scavengers and the secondary or preventive.

The secondary antioxidant mechanisms may include the deactivation of metals, inhibition of lipid hydroperoxides by interrupting the production of undesirable volatiles, the regeneration of primary antioxidants, and the elimination of singlet oxygen.

A compound that reduces in vitro radicals does not necessarily behave as an antioxidant in an in vivo system.

This is because FR diffuse and spread easily. Some have extremely short life spans, on the order of nanoseconds, so it is difficult for the antioxidant to be present at the time and place where oxidative damage is being generated.

Additionally, the reactions between antioxidants and FR are second order reactions. Therefore, they not only depend on the concentration of antioxidants and free radicals but are also dependent on factors related to the chemical structure of both reagents, the medium and the reaction conditions. The phenolic compounds constitute a wide group of chemical substances, with diverse chemical structures and different biological activities, encompassing more than different compounds which are a significant part of the human and animal diet [ 24 ].

The phenolic compounds are important components in the mechanism of signaling and defense of plants. Save to Library. Create Alert. Launch Research Feed. Three eras of vitamin C discovery. Subcell Biochem. Knight J. Free radicals: Their history and current status in aging and disease. Ann Clin Lab Sci. Wolf G. The discovery of the antioxidant function of vitamin E: The contribution of Henry A.

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Johnson F, Giulivi C. Superoxide dismutases and their impact upon human health. Mol Aspects Med. Crystal structure of nickel-containing superoxide dismutase reveals another type of active site. Peroxisomes as a source of reactive oxygen species and nitric oxide signal molecules in plant cells.

Trends Plant Sci. The expression of different superoxide dismutase forms is cell-type dependent in olive Olea europaea L. Plant Cell Physiol. J Biol Chem. Diversity of structures and properties among catalases. Cell Mol Life Sci. Predominant role of catalase in the disposal of hydrogen peroxide within human erythrocytes. Eisner T, Aneshansley DJ. Spray aiming in the bombardier beetle: Photographic evidence.

Meister A, Anderson M. Brigelius-Flohe R. Tissue-specific functions of individual glutathione peroxidases. Glutathione transferases. Annu Rev Pharmacol Toxicol. Smirnoff N. L-ascorbicacid biosynthesis. Vitam Horm. Meister A. Scheme 2 Reaction of hydroxyl radical with the sugar moiety of DNA. One unique reaction of the C50 -centered radical of the damage. This intra- and carbonyls. Thus, the oxidative purine -deoxynucleosides.

The reactions of carbon-centered damage to tissue results in the increased amount of oxidized sugar radicals result in the DNA strand breaks and base-free protein. A detailed review by Cooke et al. The amino acid's lysine, proline, histidine, and heart disease and cancer.

Modulation of free radicals by natural antioxidants Two types of antioxidants namely the enzymatic antioxidants and nonenzymatic antioxidants modulate the free radical reactions.

Body protects itself from ROS by using enzymatic antioxidant mechanisms. Examples of the enzymatic antioxidants Fig. This article is licensed under a Creative Commons Attribution 3. Vitamins Vitamin E 1,43 vitamin C 2,44 vitamin A 3. SOD's located in the cytosol and mitochondria, catalyti- cally convert the O2c into oxygen and H2O2 in presence of the metal ion cofactors such as copper Cu , zinc Zn , or manganese Mn.

It functions to inter- The enzymatic antioxidants and their mechanism of anti- cept lipid peroxyl radicals LOOc and to terminate the lipid oxidant activity has been explained in details in several review peroxidation chain reactions eqn Scheme 4 Mechanism of radical scavenging activity of ascorbic acid 2.

Moreover, it regenerates vitamin E in cell membranes in combination with GSH or compounds capable 4. The pairs of ascorbate radicals react rapidly to ols 12 e. Hence, dehydroascorbate is converted daidzein The last stage of the addition of two electrons to the dehy- droascorbate has been proposed to be carried out by oxidoreductase. Several reviews have appeared to outline the basic structural and metabolic characteristics of Scheme 5 Mechanism of radical scavenging activity of vitamin A 3.

Review RSC Adv. Three structural groups are important determi- nants of the radical-scavenging activity of anthocynidines 18— Second, the 2,3 double bond in conjugation. Third, the 4-oxofunction in the C-ring. Flavonoids form complexes with the metal ions by using the 3- or 5-hydroxyl and 4-keto- substituents or hydroxyl groups in ortho position in the B-ring.

In this process, the polyphenolic reducing agent changes to an aroxyl radical, which is comparatively more stable due to resonance than the free radical that it has reduced.

The overall result is the termination of damaging oxidative chain reactions. Scheme 6 Mechanism of superoxide anion radical scavenging activity of quercetin 5. Scheme 7 Mechanism of DNA damage induced by quercetin copper complex. Carotenoids75,76 The peroxyl i Carotines: lycopene 26, b-carotene 27, radicals generated in the process of lipid peroxidation can ii Xanthophyll: zeaxanthine 28, lutein Scavenging of peroxyl radicals Carotenoids are among the most common lipid soluble phy- tonutrients.

The long unsaturated alkyl chains in carotenoids make them highly lipophilic. Scheme 9 Mechanism of radical scavenging activity of cynidin Scheme 10 Biosynthetic pathway for the synthesis of carotenoids 26— Hydroxycinnamic acids 30—33 and their Lycopene 24, is the most potent antioxidant naturally conjugates prevent oxidative damage to the LDL. The high number of studies involving human LDL as the oxidizing substrate showed conjugated double bonds in lycopen endows it the singlet that the hydroxycinnamic acids have higher antioxidant activity oxygen quenching ability.

Lycopene demonstrate the strong as compared to the corresponding hydroxybenzoic acids. Other natural antioxidants p-coumaric acid They also suppress This article is licensed under a Creative Commons Attribution 3. DNA single-strand. Allicin is known interesting to notice that, the higher concentration of to possess various biological activities including the antibacte- piperine results in the increased production of the cOH.

Hence, this process can occur at room temperature. Allicin is known to undergo Cope elimination at room temperature to give 2-propenesulfenic acid and thioacrolein as shown in the Scheme The radical-scavenging activity of allicin involves H-atom transfer to a peroxyl radical from the methylene of the allyl group on the divalent sulfur.

Scheme 12b demonstrate an alternative mechanism, where the radical- scavenging activity of allicin can be accounted for 2-propene- sulfenic acid, which is produced from allicin by Cope elimina- tion. Subsequently, the hydroperoxide loses water comparable to that of the vitamin E. The free found that the copper complex of curcumin curcumin—Cu II radical can undergo electron transfer or abstract H-atom from show promising SOD activity, with improved antioxidant either of these two sites.

The methide radical another molecule of O2c , thereby regenerating the parent performs a 5-exo-cyclization with the double bond to give the complex.

However, in presence of the excess O2c , the phenolic results in the peroxyl radical. The peroxyl radical is then moiety undergoes oxidation resulting in the production of the reduced to the hydroperoxide by abstracting a hydrogen atom phenoxyl radicals. Then these phenoxyl radicals can generate Scheme 14 Mechanism of radical scavenging activity of curcumin 38 initiated by phenolic moiety.

Scheme 15 Mechanism of radical scavenging activity of curcumin—Cu II complex. However, it loses it's radical scavenging activity resulting in the regeneration of the complex. Physisological antioxidants note that the uric acid cannot scavenge the O2c. Moreover, uric Uric acid 39 in plasma, and GSH Neither of these antioxidants ascorbic acid, thiols alone can prevent reaction of peroxynitrite with tetrahydrobiopterin, which leads to uncoupling of nitric oxide NOc synthase.

GSH 40 in cell cytosol, together with its related enzymes, comprises a system that maintains the intracellular reducing environment, which acts as primary defense against excessive generation of harmful ROS. Uric acid 39 in plasma possesses strong radical scavenging However, the de nova synthesis of glutathione from its amino activity. It contributes for as much as as an adaptive response to oxidative stress. Scheme 16 Mechanism of radical scavenging activity of uric acid.

Fungal antioxidants and superoxide dismutase and nonenzymatic elements phenolic derivatives or polysaccharides. Cinnamic acid derivatives, 41, 42, system consisting of enzymatic peroxidases, laccase, catalase, melatonin 43, selegiline 44, are the few examples of the synthetic antioxidants. The decrease of absorbance at nm with antioxidant indicates the consumption of O2c in the reaction mixture.

The O2c scavenging activity can be measured as described by Robak and Gryglewski. Evaluation of the antioxidant activity of any compound can be carried out either by in vitro or in vivo models. Due to its odd electron, the methanolic solution of DPPH shows a strong absorption band at nm. As shown in the Scheme 19, the DPPH radical reacts with suitable reducing agent producing new bond, thus changing the color of solution.

The solution loses color with the increase in the concentration of antioxidant as the electrons taken up by DPPH radical from the antioxidant. However, the carbon-centered radicals usually 5.

Assay of superoxide anion radical scavenging activity predominate. The luminol ROS. The method for the evaluation of the O2c scavenging activity 5. In vitro antioxidant evaluation by phospholipids of antioxidants is explained here by using PMS—NADH—NBT peroxidation system, which is composed of N-methylphenazine methosul- Lipid peroxidation is an oxidative degradation of lipids. The tentative mechanism for this free radical chain reaction In general, the in vivo assays for testing potential antioxi- involved in the phospholipid peroxidation is depicted in the dants are more expensive because they require complex cellular Scheme The activity with an in vitro method in order to obtain information interference of the test drug with color development is deter- on some aspects like uptake, bioavailability, and metabolism.

In vitro antioxidant evaluation by deoxyribose assay assays for the evaluation of the antioxidant activities of natural antioxidants. There are several other reports, which elaborate The cOH in presence of ascorbic acid attack the sugar deoxyri- the advantages and disadvantages of various methods for the bose to generate the product that on heating with thiobarbituric evaluation of antioxidant activity.

Therefore, the deoxyribose assay can be used to detect cOH scavenging activity of test 6. Current trends and future compounds. Scheme 22 depicts the proposed the improvement of human health. Multiple studies have mechanism of chromogen formation from reaction of deoxyri- showed that the neuronal and behavioral changes occur with bose and cOH followed by reaction with TBARS.

Recent studies have found the association between the lower status of dietary antioxidants and decline in the cognitive function. The evidences from the experimental, clinical, and epidemiological studies indicate that the consumption of foods containing high levels of dietary antioxidants may prevent or reduce the risk of cognitive deterioration.

Tempol, an example of a new class of SOD mimetic drugs, alleviates acute and chronic pain. Scheme 21 Phospholipid peroxidation of unsaturated lipids. Conclusion ROS, the radical derivatives of oxygen are the most important physiological radical reactions and the mechanisms of the free radical in biological systems. Catalase EC 1.

It is present in nearly all animal cells as a protective enzyme. The highest levels of CAT activity are measured in the liver, kidney, and red blood cells. CAT enzyme reacts with H 2 O 2 to form water and molecular oxygen and with H donors such as methanol, ethanol, formic acid, or phenols with peroxidase activity. CAT protects cells from H 2 O 2 generated within them. Therefore, it has an essential role in the acquisition of tolerance to oxidative stress in the adaptive response of cells.

Various disease conditions and abnormalities are associated with the deficiency or mutation of CAT enzyme [ 30 , 31 ]. In the food industry, CAT enzyme is used to remove H 2 O 2 from milk prior to cheese production, and to prevent food from oxidizing in food wrappers. In addition, CAT enzyme is used in the textile industry for H 2 O 2 removal from fabrics, to make sure the material is peroxide free.

Recently, esthetics industries have begun to use CAT enzyme in facial masks, as the combination of CAT enzyme with H 2 O 2 on the face can be used to increase cellular oxygenation in the upper layers of the epidermis [ 3 ].

Glutathione peroxidase EC 1. In mammals, there are five GPx isoenzymes. Though their expression is ubiquitous, the level of each isoform differs depending on their tissue type. Mitochondrial and cytosolic glutathione peroxidase GPx1 or cGPx reduces fatty acid hydroperoxides and H 2 O 2 at the expense of glutathione [ 32 ].

GPx1 is the main ubiquitous selenoperoxidase present in most cells; found in the cytosolic, mitochondrial, and peroxisomal compartments. It is an important antioxidant enzyme required in the detoxification of H 2 O 2 and lipid hydroperoxides and preventing DNA, protein and lipids damage by harmful accumulation of intracellular H 2 O 2 [ 33 ].

Phospholipid hydroperoxidase glutathione PHGPX is found in most tissues and can directly reduce the phospholipid hydroperoxides, fatty acid hydroperoxides, and cholesterol hydroperoxides that are produced in peroxidized membranes and oxidized lipoproteins [ 30 ]. GPx4 is found in both the cytosol and the membrane fraction, and is highly expressed in renal epithelial cells and tests. Cytosolic GPx2 or extracellular GPx3 is inadequately found in nearly all tissues except for the gastrointestinal tract and kidney.

In recent, GPx5, a new kind, expressed particularly in mouse epididymis, is selenium independent [ 34 ]. Several studies underlined the clinical importance of GPx. In addition, GPx, especially GPx1, have been implicated in the progression and prevention of many frequent and complex diseases, including cancer and cardiovascular disease [ 34 , 35 ].

GPx is an important antioxidant enzyme in the body. GHS plays an essential role in red blood cells to remain intact and protects white blood cells, which are responsible for the immune system. In previous decades, there has been increasing evidence that large amounts of antioxidants present in our diet contribute to the antioxidant defense system by preventing oxidative stress and specific human diseases. Phytochemicals, the plant-derived compounds, are one of the classes of the dietary factors, which play an essential role in functions of the body.

Food materials contain a number of natural compounds reported to have antioxidant characteristics due to the presence of hydroxyl groups in their structure.

Synthetic and natural antioxidants prevent the oxidative damage to the most important macromolecules such as lipids, proteins, and nucleic acids found in human body through scavenging the free radicals formed in different biochemical processes [ 36 ]. Download Citation. RSC Adv. Author version available. Download author version PDF.

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Expert Opinion on Biological Therapy. Retrieved 13 June Archived from the original PDF on 29 December Retrieved 24 October Comparative Biochemistry and Physiology A. Impact of Processing on Food Safety. Advances in Experimental Medicine and Biology. Three eras of vitamin C discovery. Annals of Clinical and Laboratory Science. Halliwell, Barry. Butylated hydroxytoluene 2,6-Di- tert -butylphenol 1,2-Diaminopropane 2,4-Dimethyl tert -butylphenol Ethylenediamine.

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An free radicals natural antioxidants and their reaction mechanisms is a substance that at low concentrations delays or prevents oxidation of a substrate. Antioxidant compounds act through several chemical mechanisms: hydrogen atom transfer HATsingle electron transfer SETand the ability to chelate transition metals. The importance of antioxidant mechanisms is to understand the biological meaning of antioxidants, their possible uses, their production by organic synthesis or biotechnological methods, or for the standardization of the determination of free radicals natural antioxidants and their reaction mechanisms activity. In general, antioxidant molecules can react either by multiple mechanisms or by a predominant mechanism. The chemical structure of the antioxidant substance allows understanding of the antioxidant reaction mechanism. This chapter reviews the in vitro antioxidant reaction mechanisms of organic antiooxidants polyphenols, carotenoids, and vitamins C against free radicals FR and prooxidant compounds under diverse conditions, as well as the most commonly used methods to evaluate the antioxidant activity of these compounds according to the mechanism involved in the reaction with free radicals and the methods of in vitro antioxidant evaluation free radicals natural antioxidants and their reaction mechanisms are used frequently depending on the reaction mechanism of the antioxidant. Oxidative stress in biological systems is a complex process that is characterized by an imbalance between the production of free radicals FR and the ability of free radicals natural antioxidants and their reaction mechanisms body to eliminate these reactive species through the use of endogenous and exogenous antioxidants. A biological system in the presence of an excess of ROS can present different pathologies, from cardiovascular diseases to the promotion of cancer. Biological systems have antioxidant mechanisms to control damage of enzymatic and nonenzymatic natures that allow ROS to be inactivated. The endogenous antioxidants are enzymes, such as superoxide dismutase SODcatalase CATglutathione peroxidase, or non-enzymatic compounds, such as bilirubin and albumin. Dragon city free gems no hack an organism is exposed to a high concentration of ROS, the endogenous antioxidant system is compromised and, consequently, it fails to guarantee complete protection of the organism. To compensate this deficit of antioxidants, the body david lloyd free day pass 2018 use exogenous free radicals natural antioxidants and their reaction mechanisms best free webcam software windows 7 through food, nutritional supplements, or pharmaceuticals. Among the most important exogenous antioxidants are phenolic compounds carotenoids and vitamins C and some minerals such as selenium and zinc. In the study of antioxidant compounds and the mechanisms involved, it is important to distinguish between the concepts of antioxidant activity and capacity. Radiicals terms are often used interchangeably. However, antioxidant activity refers to the rate constant of a reaction between an antioxidant and an oxidant. The antioxidant capacity is a measure of the amount of a certain free radical captured by an antioxidant sample [ 1 ]. Therefore, during the selection of a method, the response parameter must be considered to evaluate the antioxidant properties of a sample, which may be a function of the concentration antioxjdants the substrate or concentration free radicals natural antioxidants and their reaction mechanisms the time required to inhibit a free radicals natural antioxidants and their reaction mechanisms concentration antoxidants the ROS. The reaction mechanisms of the antioxidant compounds are closely related to the reactivity and chemical structure antioxdants FR as well as the environment in which these reactive species are found. Therefore, it is very important to describe the ROS and, to a lesser degree, the reactive nitrogen species RNSwhich include both precursors and free radicals. free radicals natural antioxidants and their reaction mechanisms The antioxidant compounds react in one-electron reactions with free radicals in vivo/in vitro and prevent oxidative damage. Therefore, it is very. The antioxidant compounds react in one-electron reactions with free radicals in vivo / in vitro and prevent the oxidative damage. Therefore, it is. Thus, the search for effective, nontoxic natural compounds with antioxidative activity [7] Free radicals can also be formed in nonenzymatic reactions of oxygen with [21] The possible mechanisms by which vitamin C may affect carcinogenesis These antioxidants delay or inhibit cellular damage mainly through their free. Free radicals, natural antioxidants, and their reaction mechanisms The antioxidant compounds react in one-electron reactions with free radicals in vivo/​in vitro. The normal biochemical reactions in our body, increased exposure to the environment, and higher levels of dietary xenobiotic's result in the generation of. Therefore, it is very important to understand the reaction mechanism of antioxidants with the free radicals. This review elaborates the mechanism of action of the. This chapter reviews the in vitro antioxidant reaction mechanisms of organic paired in their respective molecular orbitals, known as maximum natural stability. due to their conversion into free radicals or their effect on the formation of FR. Carbohydrates free radical oxidation mechanisms are comparable to those of lipids. In addition, antioxidants act as free radical scavengers, by reacting with the reactive Based on their occurrence, antioxidants are categorized as natural or. Antioxidants are compounds that inhibit oxidation. Oxidation is a chemical reaction that can produce free radicals, thereby The free radical mechanism of lipid peroxidation. These preservatives include natural antioxidants such as ascorbic acid (AA, E) and tocopherols (E), as well as synthetic antioxidants such. This type of oxidative damage to DNA is highly correlated to the physiological conditions such as mutagenesis, carcinogenesis, and aging. Ficek, Reprod. Hwang, G. The synthetic antioxidants are the second type of nonenzymatic antioxidants. Plants and animals, as well as all other forms of life, have their own defenses against free radicals and oxidative damage. Nakayama and 63 T. Calliste, D. The reported chemical evidence suggests that the organism's health span. Historical Collection. Pang, A. Wright, Cancer. Escobar, S. GSH Glutathione 22 B. Damaging reactions of free radicals These ROS can act by either of the two oxygen dependent ROS Table 1 induced oxidative stress is associated with the mechanisms resulting in the destruction of the microorganism chronic diseases such as cancer, coronary heart disease CHD , or other foreign matter. free radicals natural antioxidants and their reaction mechanisms