A Review on Dietary Antioxidants Dr. Suja C,, Shuhaib.B, Muhammed Abdurahman, Hunaida khathoom , Simi k Crescent College of Pharmaceutical Sciences, Madayipara, Payangadi R.S.(Post), Kannur, Kerala. Abstract: An antioxidant is a molecule stable enough to donate an electron to a rampaging free radical and neutralize it, thus reducing its capacity to damage. Mechanism of action of anti oxidant are a chain- breaking mechanism by which the primary antioxidant donates an electron to the free radical present in the systems and removal of ROS/reactive nitrogen species initiators by quenching chain-initiating catalyst. The article present a broad review on the dietary sources, several disease prevention by dietary anti oxidant .In this review study the cancer prevention, aspect of plant poly phenol as dietary anti oxidant in human health and the cardio protective effect, anti diabetic effect, anti aging effect , neuro protective effect are studied. From this review study we have come to the conclusion that dietary antioxidants are good for prevention of many of the lifestyle diseases, cancer etc as prevention is better than cure. Key word: Anti oxidant, Mechanism, Poly phenol etc Introduction: Free radicals A free radical can be defined as any molecular species capable of independent existence that contains an unpaired electron in an atomic orbital. The presence of an unpaired electron results in certain common properties that are shared by most radicals. Many radicals are unstable and highly reactive1. They can either donate an electron to or accept an electron from other molecules, therefore behaving as oxidants or reductants. Free radicals are derived either from normal essential metabolic processes in the human body or from external sources such as exposure to X-rays, ozone, cigarette smoking, air pollutants, and industrial chemicals. Free radical formation occurs continuously in the cells as a consequence of both enzymatic and nonenzymatic reactions. Enzymatic reactions, which serve as source of free radicals, include those involved in the respiratory chain, in phagocytosis, in prostaglandin synthesis, and in the cytochrome P-450 system. Free radicals can also be formed in nonenzymatic reactions of oxygen with organic compounds as well as those initiated by ionizing reactions. An antioxidant is a molecule stable enough to donate an electron to a rampaging free radical and neutralize it, thus reducing its capacity to damage. These antioxidants delay or inhibit cellular damage mainly through their free radical scavenging property. These low-molecular-weight antioxidants can safely interact with free radicals and terminate the chain reaction before vital molecules are damaged. Some of such antioxidants, including glutathione, ubiquinol, and uric acid, are produced during normal metabolism in the body2. Antioxidants act as radical scavenger, hydrogen donor, electron donor, peroxide decomposer, singlet oxygen quencher, enzyme inhibitor, synergist, and metal-chelating agents. Mechanism of action of antioxidants Two principle mechanisms of action have been proposed for antioxidants. The first is a chainbreaking mechanism by which the primary antioxidant donates an electron to the free radical present in the systems. The second mechanism involves removal of ROS/reactive nitrogen species initiators (secondary antioxidants) by quenching chain-initiating catalyst. Antioxidants may exert their effect on biological systems by different mechanisms including electron donation, metal ion chelation, co- antioxidants , or gene expression regulation3. Levels of antioxidant action The antioxidants acting in the defence systems act at different levels such as preventive, radical scavenging, repair, and the fourth line of defence, i.e., the adaptation.The first line of defence is the preventive antioxidants, which suppress the formation of free radicals. Although the precise mechanism and site of radical formation in vivo are not well elucidated yet, the metal-induced decompositions of hydro peroxides and hydrogen peroxide must be one of the important source. The second line of defence is the antioxidants that scavenge the active radicals to suppress chain initiation and/or break the chain propagation reactions. Various endogenous radical-scavenging antioxidants are known: some are hydrophilic and others are lipophilic. Vitamin C, uric acid, bilirubin, albumin, and thiols are hydrophilic, radical-scavenging antioxidants, while vitamin E and ubiquinol are lipophilic radical-scavenging antioxidants. Vitamin E is accepted as the most potent radical-scavenging lipophilic antioxidant4.The third line of defense is the repair antioxidants. The proteolytic enzymes, proteinases, proteases, and peptidases, present in the cytosol and in the mitochondria of mammalian cells, recognize, degrade, and remove oxidatively modified proteins and prevent the accumulation of oxidized proteins.5 Types of antioxidants Enzymatic Cells are protected against oxidative stress by an interacting network of antioxidant enzymes. Here, the superoxide released by processes such as oxidative phosphorylation is first converted to hydrogen peroxide and then further reduced to give water. This detoxification pathway is the result of multiple enzymes, with superoxide dismutase’s catalyzing the first step and then catalases and various peroxidases removing hydrogen peroxide. Superoxide dismutase Superoxide dismutases (SODs) are a class of closely related enzymes that catalyze the breakdown of the superoxide anion into oxygen and hydrogen peroxide.SOD enzymes are present in almost all aerobic cells and in extracellular fluids6. In humans three forms of superoxide dismutase are present. SOD1 is located in the cytoplasm, SOD2 in the mitochondria, and SOD3 is extracellular. The first is a dimer (consists of two units), while the others are tetramers (four subunits). SOD1 and SOD3 contain copper and zinc, while SOD2 has manganese in its reactive center7.Catalase is a common enzyme found in nearly all living organisms, which are exposed to oxygen, where it functions to catalyze the decomposition of hydrogen peroxide to water and oxygen. Hydrogen peroxide is a harmful by-product of many normal metabolic processes: to prevent damage, it must be quickly converted into other, less dangerous substances8. Glutathione systems include glutathione, glutathione reductase, glutathione peroxidases, and glutathione S-transferases. This system is found in animals, plants, and microorganisms. Glutathione peroxidase is an enzyme containing four selenium-cofactors that catalyze the breakdown of hydrogen peroxide and organic hydroperoxides Nonenzymatic Ascorbic acid------ or “vitamin C” is a monosaccharide anti oxidant found in both animals and plants. As it cannot be synthesized in humans and must be obtained from the diet, it is a vitamin. Most other animals are able to produce this compound in their bodies and do not require it in their diets. In cells, it is maintained in its reduced form by reaction with glutathione, which can be catalyzed by protein disulfide isomerase and glutaredoxins. Glutathione ------ is a cysteine-containing peptide found in most forms of aerobic life. It is not required in the diet and is instead synthesized in cells from its constituent amino acids. Glutathione has antioxidant properties since the thiol group in its cysteine moiety is a reducing agent and can be reversibly oxidized and reduced. Melatonin------also known chemically as N-acetyl-5-methoxytryptamine,is a naturally occurring hormone found in animals and in some other living organisms, including algae. Melatonin is a powerful antioxidant that can easily cross cell membranes and the blood–brain barrier. Unlike other antioxidants, melatonin does not undergo redox cycling, which is the ability of a molecule to undergo repeated reduction and oxidation 9 Tocopherols and tocotrienols------Vitamin E is the collective name for a set of eight related tocopherols and tocotrienols, which are fat-soluble vitamins with antioxidant properties. Of these, α-tocopherol has been most studied as it has the highest bioavailability, with the body preferentially absorbing and metabolizing this form. It has been claimed that the α-tocopherol form is the most important lipid-soluble antioxidant, and that it protects membranes from oxidation by reacting with lipid radicals produced in the lipid peroxidation chain reaction. Uric acid------ accounts for roughly half the antioxidant ability of plasma. In fact, uric acid may have substituted for ascorbate in human evolution. However, like ascorbate, uric acid can also mediate the production of active oxygen species Literature review Diet as a source of antioxidants Synthetic and natural food antioxidants are used routinely in foods and medicine especially those containing oils and fats to protect the food against oxidation. There are a number of synthetic phenolic antioxidants, butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA) being prominent examples. In view of increasing risk factors of human to various deadly diseases, there has been a global trend toward the use of natural substance present in medicinal plants and dietary plats as therapeutic antioxidants. It has been reported that there is an inverse relationship between the dietary intake of antioxidant-rich food and medicinal plants and incidence of human diseases. The use of natural antioxidants in food, cosmetic, and therapeutic industry would be promising alternative for synthetic antioxidants in respect of low cost, highly compatible with dietary intake and no harmful effects inside the human body. Many antioxidant compounds, naturally occurring in plant sources have been identified as free radical or active oxygen scavengers. Attempts have been made to study the antioxidant potential of a wide variety of vegetables like potato, spinach, tomatoes, and legumes. The commonly used dietary antioxidant includes (with common/ayurvedic names in brackets) Allium cepa (Onion), A. sativum (Garlic, Lahasuna),Amomum subulatum (Greater cardamom, Bari elachi), Andrographis paniculata (Kiryat), Azadirachta indica (Neem, Nimba), Bacopa monniera (Brahmi), Camellia sinensis (Green tea), Cinnamomum verum (Cinnamon),Curcma longa (Turmeric, Haridra), Emblica officinalis (Inhian gooseberry, Amlaki),Mangifera indica (Mango, Amra), Momordica charantia (Bitter gourd), Murraya koenigii (Curry leaf), Picrorrhiza kurroa (Katuka), Piper beetle and Zingiber officinalis (Ginger)10. Cancer chemoprevention through dietary antioxidants It was estimated that nearly one third of all cancer details in United States could be prevented through appropriate dietary modification. Various dietary antioxidants have shown considerable promise as effective agents for cancer prevention by reducing oxidative stress which has been implicated in the development of many diseases, including cancer. Therefore, for reducing the incidence of cancer, modifications in dietary habits, especially by increasing consumption of fruits and vegetables rich in antioxidants are increasingly advocated. This review presents an extensive analysis of the key findings from studies on the effects of dietary antioxidants such as, curcumin, lupeol, and pomegranate,against cancers of skin ,prostate,breast and liver .Cancer is a disease in which a series of cumulative and genetic changes that are initiated in a normal cell occur .Chemoprevention is a strategy to completely halt or slow the process of cancer development by intervening in the process of carcinogenesis.11 Curcumin Curcumin is a major yellow pigment in turmeric that impartsa yellow colour to food and is widely used as a spice. It is derived from the roots of plant Curcuma longa. In MCF-7 breast cancer cells, telomerase activity decreased with increasing concentrations of curcumin, may be due to downregulation of hTERT expression. Curcumin caused a steady decrease in the level of human telomerase reverse Transcriptase (hTERT) mRNA in MCF-7 cells12.Curcumin inhibited camptothecin, mechlorethamine, and using a in vivo model of human breast cancer, dietary supplementation with curcumin was found to significantly inhibit cyclophosphamide-induced tumor regression which was accompanied by a decrease in activation of apoptosis by cyclophosphamide and decreased JNK (JUN N TERMINAL KINASE) activation.13 Pomegranate The pomegranate (Punica granatum L.) fruit has been used for centuries in ancient cultures for its medicinal purposes. Pomegranate fruits are widely consumed in fresh and beverage forms as juice. Ellagic acid, caffeic acid, luteolin, and punicic acid, all important components of the aqueous compartments or oily compartment of pomegranate fruit were reported to inhibit invitro invasion of human PC-3 prostate cancer cells in an assay employing matrigel artificial membranes. It was shown that PFE treatment of human prostate cancer PC-3 cells resulted in a dose dependent inhibition of cell growth/cell viability and induction of apoptosis14. Lupeol Lup-20-en-3-ol (Lupeol), a triterpene found in fruits such as such as olive, mango, strawberry, grapes, and figs, in many vegetables, and in several medicinal plants, is used in the treatment of various diseases. It possesses strong anti-inflammatory, antiarthritic, antimutagenic, and antimalarial activity in vitro and in vivo systems. Lupeol has been shown to act as a potent inhibitor of protein kinases and serine proteases and to inhibit the activity of DNA topoisomerase II, a target for anticancer chemo therapy. It has also been reported to improve the epidermal tissue reconstitution and induces differentiation and inhibits the cell growth of melanoma cells.15Lupeol treatment resulted in significant inhibition of cell viability in a dose-dependent manner and caused apoptotic death of prostate cancer cells. Lupeol was found to induce the cleavage of PARP protein and degradation of acinus protein with a significant increase in the expression of FADD protein and Fas receptor.16 Plant polyphenols as dietary antioxidants in human health and disease Polyphenols are secondary metabolites of plants and are generally involved in defense against ultraviolet radiation or aggression by pathogens. In the last decade, there has been much interest in the potential health benefits of dietary plant polyphenols as antioxidant. Epidemiological studies and associated meta-analyses strongly suggest that long term consumption of diets rich in plant polyphenols offer protection against development of cancers, cardiovascular diseases, diabetes, and osteoporosis and neurodegenerative diseases Polyphenols are naturally occurring compounds found largely in the fruits, vegetables, cereals and beverages. Fruits like grapes, apple, pear, cherries and berries contains up to 200–300 mg polyphenols per 100 grams fresh weight. The products manufactured from these fruits, also contain polyphenols in significant amounts.1 7 Typically a glass of red wine or a cup of tea or coffee contains about 100 mg polyphenols. Cereals, dry legumes and chocolate also contribute to the polyphenolic intake.Polyphenols are secondary metabolites of plants and are generally involved in defense against ultraviolet radiation or aggression by pathogens. In food, polyphenols may contribute to the bitterness, astringency, color, flavor, odor and oxidative stability. Polyphenols and other food phenolics is the subject of increasing scientific interest because of their possible beneficial effects on human health. This review focuses on the present understanding of the biological effects of dietary polyphenols and their importance in human health and disease. Structure and classes of polyphenols 1. Phenolic acids: Phenolic acids are found abundantly in foods and divided into two classes:derivatives of benzoic acid and derivatives of cinnamic acid. The hydroxybenzoic acid content of edible plants is generally low, with the exception of certain red fruits, black radish and onions, which can have concentrations of several tens of milligrams per kilogram fresh weight. The hydroxycinnamic acids are more common than hydroxybenzoic acids and consists chiefly of p-coumaric, caffeic, ferulic and sinapic acids.18 2. Flavonoid : Flavonoids comprise the most studied group of polyphenols. This group has a common basic structure consisting of two aromatic rings bound together by three carbon atoms that form an oxygenated heterocycle . More than 4,000 varieties of flavonoids have been identified, many of which are responsible for the attractive colours of the flowers, fruits and leaves.Based on the variation in the type of heterocycle involved, flavonoids may be divided into six subclasses: flavonols, flavones, flavanones,flavanols,anthocyaninsand isoflavones . Individual differences within each group arise from the variation in number and arrangement of the hydroxyl groups and their extent of alkylation and/or glycosylation. Quercetin, myricetin, catechins etc. are some most common flavonoids. 19 3. Stilbenes: Stilbenes contain two phenyl moieties connected by a two-carbon methylene bridge. Occurrence of stilbenes in the human diet is quite low. Most stilbenes in plants act as antifungal phytoalexins, compounds that are synthesized only in response to infection or injury. One of the best studied, naturally occurring polyphenol stilbene is resveratrol (3,4',5 trihydroxystilbene), found largely in grapes. A product of grapes, red wine also contains significant amount of resveratrol.20 Stilbenes 4. Lignans: Lignans are diphenolic compounds that contain a 2,3-dibenzylbutane structure that is formed by the dimerization of two cinnamic acid residues . Several lignans, such as secoisolariciresinol, are considered to be phytoestrogens. The richest dietary source is linseed, which contains secoisolariciresinol (up to 3.7 g/kg dry weight) and low quantities of matairesinol.21 Poly phenols and human diseases Epidemiological studies have repeatedly shown an inverse association between the risk of chronic human diseases and the consumption of polyphenolic rich diet. The phenolic groups in polyphenols can accept an electron to form relatively stable phenoxyl radicals, thereby disrupting chain oxidation reactions in cellular components. It is well established that polyphenol-rich foods and beverages may increase plasma antioxidant capacity.22This increase in the antioxidative capacity of plasma following the consumption of polyphenol-rich food may be explained either by the presence of reducing polyphenols and their metabolites in plasma, by their effects upon concentrations of other reducing agents (sparing effects of polyphenols on other endogenous antioxidants), or by their effect on the absorption of pro-oxidative food components, such as iron. Consumption of antioxidants has been associated with reduced levels of oxidative damage to lymphocytic DNA. Similar observations have been made with plyphenol-rich food and beverages indicating the protective effects of polyphenol. Cardioprotectve effect Number of studies has demonstrated that consumption of polyphenols limits the incidence of coronary heart diseases. Atherosclerosis is a chronic inflammatory disease that develops in lesion-prone regions of medium-sized arteries. Atherosclerotic lesions may be present and clinically silent for decades beforebecoming active and producing pathological conditions such as acute myocardial infarction, unstable angina or sudden cardiac death. Polyphenols are potent inhibitors of this type of oxidation is considered to be a key mechanism in development of atherosclerosis. Other mechanisms by which polyphenols may be protective against cardiovascular diseases are antioxidant, anti-platelet, anti-inflammatory effects as well as increasing HDL, and improving endothelial function. Polyphenols may also contribute to stabilization of the atheroma Plaque.Quercetin, the abundant polyphenol in onion has been shown to be inversely associated with mortality from coronary heart disease by inhibiting the expression of metalloproteinase1 (MMP1), and the disruption of atherosclerotic plaques. Polyphenols may also exert antithrombotic effects by means of inhibiting platelet aggregation. Consumption of red wine or non-alcoholic wine reduces bleeding time and platelet aggregation. Thrombosis induced by stenosis of coronary artery is inhibited when red wine or grape juice is administrated.Polyphenols can improve endothelial dysfunction associated with different risk factors for atherosclerosis before the formation of plaque; its use as a prognostic tool for coronary heart diseases has also been proposed. Anti diabetic effect Impairment in glucose metabolism leads to physiological imbalance with the onset of the hyperglycemia and subsequently diabetes mellitus. There are two main categories of diabetes; type-1 and type-2. Studies have shown that several physiological parameters of the body get altered in the diabetic conditions. Long term effects of diabetes include progressive development of specific complements such as retinopathy, which affects eyes and lead to blindness; nephropathy in which the renal functions are altered or disturbed and neuropathy which is associated with the risks of amputations, foot ulcers and features of autonomic disturbance including sexual dysfunctions. Numerous studies report the antidiabetic effects of polyphenols. Tea catechins have been investigated for their antidiabetic potential. Polyphenols may affect glycemia through different mechanisms, including the inhibition of glucose absorption in the gut or of its uptake by peripheral tissues. The inhibition of intestinal glycosidases and glucose transporter by polyphenols has been studied. Individual polyphenols, such as (+)catechin, (-)epicatechin, (-)epigallocatechin, epicatechin gallate, isoflavones from soyabeans, tannic acid, glycyrrhizin from liquorice root, chlorogenic acid and saponins also decrease S-Glut-1 mediated intestinal transport of glucose. Saponins additionally delay the transfer of glucose from stomach to the small intestine.22 Anti-aging effect Aging is the accumulation process of diverse detrimental changes in the cells and tissues with advancing age, resulting in an increase in the risks of disease and death. Among many theories purposed for the explaining the mechanism of aging, free radical/oxidative stress theory is one of the most accepted one. Several researches suggest that the combination of antioxidant/anti- inflammatory polyphenolic compounds found in fruits and vegetables may show efficacy as antiaging compounds. Subset of the flavonoids known as anthocyanins, are particularly abundant in brightly colored fruits such as berry fruits and concord grapes and grape seeds. Anthocyanins are responsible for the colors in fruits, and they have been shown to have potent antioxidant/anti-inflammatory activities, as well as to inhibit lipid peroxidation and the inflammatory mediator’s cyclo-oxygenase (COX)1. Fruit and vegetable extracts that have high levels of flavonoids also display high total antioxidant activity such as spinach, strawberries and blueberries. It is reported that the dietary supplementations (for 8 weeks) with spinach, strawberry or blueberry extracts in a control diet were also effective in reversing age-related deficits in brain and behavioral function in aged rats.A recent study demonstrates that the tea catechins carry strong anti-aging activity and consuming green-tea rich in these catechins, may delay the onset of aging.23 Neuro protective effect Oxidative stress and damage to brain macromolecules is an important process in neurodegenerative diseases. polyphenols are highly antioxidative in nature, their consumption may provide protection in neurological diseases.It was observed that the people drinking three to four glasses of wine per day had 80% decreased incidence of dementia and Alzheimer’s disease compared to those who drank less or did not drink at all.Resveratrol, abundantly present in wine scavenges O2 and OH in vitro, as well as lipid hydroperoxyl free radicals, this efficient antioxidant activity is probably involved in the beneficial effect of the moderate consume of red wine against dementia in the elderly. It was found that the consumption of fruit and vegetable juices containing high concentrations of polyphenols, at least three times per week, may play an important role in delaying the onset of Alzheimer’s disease. Polyphenols from fruits and vegetables seem to be invaluable potential agents in neuroprotection by virtue of their ability to influence and modulate several cellular processes such as signaling, proliferation, apoptosis, redox balance and differentiation of Dopaminergic neurons in the substantia nigra zona compacta. Effect of dietary antioxidants on cardiovascular disease Antioxidant Intakes and CVD Intake of fruits and vegetables has long been associated with a lower risk for several chronic diseases mediated by oxidative stress, including CVD. Dietary Antioxidan t such as Vit E,Carotenoids, and polyphenols were thought to responsible for the cardiovascular protective effect through suppressing oxidative stress suggested by preclinical studies and epidemiological studies. Dietary Vitamin E The effects of dietary vitamin E intake on CVD risk have been investigated by several large cohort studies. An inverse association between dietary total vitamin E intake and heart disease risk was reported by several studies though; findings were controversial when a vitamin E supplement was used. The Nurses’ Health Study (NHS) conducted in 1980 involved more than 87,000 U.S. female nurses between 34 and 59 years old with no history of CVD to investigate the association between dietary vitamin E intake and CVD risk. After an 8-year follow-up, women in the top quartile of total vitamin E intake had a 34% lower risk (RR: 0.66; 95% CI: 0.50, 0.87) of coronary disease compared with those in the bottom quintile. Further analysis from the study showed that the inverse association was only attributable to vitamin E supplement intake rather than vitamin E from diet.antioxidants such as vitamin E, carotenoids, and polyphenols were thought to responsible for the cardiovascular protective effect through suppressing oxidative stress suggested by preclinical studies and epidemiological studies Dietary Vitamin C Although studies on plasma vitamin C were limited, dietary vitamin C intake has been widely studied in relation to CVD risk in several prospective cohort studies. Three out of eleven studies identified found significant protective association between dietary vitamin C intake and CVD outcomes. The most significant result was observed in the NHS, in which 85,118 nurses were followed for 16 years since 1980. Women in the top quartile of total vitamin C intake had a 27% lower risk (RR: 0.73; 95% CI: 0.57, 0.94) of nonfatal MI and fatal CHD compared with those in the bottom quintile. Further analysis from the study showed that the inverse association was only attributable to vitamin C supplement intake rather than vitamin C from diet. Dietary Carotenoids Among the cohort studies of dietary carotenoids, seven out of ten studies reported significant associations between dietary carotenoids and CVD outcomes in a protective direction, especially for dietary β-carotene intake. In the NHS cohort, 73,286 women had been followed up for 12 years since 1984. A study reported inverse associations between intakes of α-carotene, βcarotene and CAD, and no associations between intakes of lutein/zeaxanthin, lycopene, or βcryptoxanthin and CAD. In the HPFS (Health Professional Follow up Study) , smoking status was a significant effect modifier in the association between carotene intake nutrients. Antioxidant Vitamin Supplements Previously reviewed large cohort studies have suggested that antioxidant vitamins, especially vitamin E, vitamin C, and β-carotene may reduce CVD risk. Accordingly, these vitamin supplements were widely tested in several large-scale, randomized controlled trials to investigate their protective Polyphenols are widely distributed in the human diet, mainly derived from plant foods such as fruits, vegetables, nuts, seeds, tea, red wine, and cocoa. Polyphenols are characterized by having at least one aromatic ring with one or more hydroxyl groups attached and have been reported to have more than 8000 structures.24 Dietary TAC (total antioxidant capacity) Given the evidence that single antioxidant supplements showed no beneficial effects on preventing CVD, as well as the fact that diet high in antioxidants such as fruits, vegetables, and tea has been widely reported to have beneficial health effects, dietary TAC that considers all the antioxidants present in diet and the synergistic effects between them thus are drawing increasing attention. Dietary TAC has been found to be positively associated with several diet quality scores as well as typical individual antioxidants, indicating dietary TAC represents dietary quality and antioxidant status in these study populations. Conclusion An antioxidant is a molecule stable enough to donate an electron to a free radical and neutralise it, thus reducing its capacity to damage. These antioxidants delay or inhibit cellular damage mainly through the free radical scavenging property. Nowadays human beings are being affected by numerous diseases. Providing diets enriched with antioxidants is a critical tool against these diseases. Antioxidants are also an effective agent for cancer prevention as it reduces the oxidative stress which has been implicated in the development of cancer. Polyphenols are secondary metabolites of plants and are generally involved in defence against UV radiation or aggression by pathogen. 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