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Quercetin: a Versatile Flavonoid

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Quercetin: a Versatile Flavonoid Internet Journal of Medical Update, Vol. 2, No. 2, Jul-Dec 2007 Clinical Knowledge Quercetin: A Versatile Flavonoid Dr. Parul Lakhanpal*, MD and Dr. Deepak Kumar Rai†, MD *Reader, Department of Pharmacology, SSR Medical College, Mauritius †SMHO, Department of Pediatrics, Ministry of Health & Quality of Life, Mauritius (Received 04 January 2007 and accepted 29 March 2007) ABSTRACT: Associative evidence from observational and intervention studies in human subjects shows that a diet including plant foods (particularly fruit and vegetables rich in antioxidants) conveys health benefits. There is no evidence that any particular nutrient or class of bioactive substances makes a special contribution to these benefits. Flavonoids occur naturally in fruits, vegetables and beverages such as tea and wine. Quercetin is the major flavonoid which belongs to the class called flavonols. Quercetin is found in many common foods including apples, tea, onions, nuts, berries, cauliflower, cabbage and many other foods. Quercetin provides many health promoting benefits, including improvement of cardiovascular health, eye diseases, allergic disorders, arthritis, reducing risk for cancers and many more. The main aim of this review is to obtain a further understanding of the reported beneficial health effects of Quercetin, its pharmacological effects, clinical application and also to evaluate its safety. KEY WORDS: Quercetin, Flavonoid, Antioxidant, Health. INTRODUCTION: on the basis of their molecular structures (Figure Quercetin is a unique bioflavonoid that has been 1)4. extensively studied by researchers over the past Six-member ring condensed with the benzene 30 years. Bioflavonoids were first discovered by ring is either a-pyrone (flavonols and Nobel Prize laureate Albert Szent Gyorgyi in the flavonones) or its dihydroderivative (flavanols year 1930. Flavonoids belong to a group of and flavanones). The position of the benzenoid natural substances with variable phenolic substituent divides the flavonoid class into structure and are found in the fruits, vegetables, flavonoids (2-position) and isoflavonoids (3- grains, bark roots, stem, flowers, tea and wine1. position). Flavonols differ from flavonones by These natural products were known for their hydroxyl group the 3-position and C2-C3 double beneficial effects on health long before bonds5. Flavonoids are often hydroxylated in flavonoids were isolated as the effective position 3, 5, 7, 2’, 3’, 4’, 5’. Methylethers and compounds. More than 4000 varieties of acetylesters of the alcohol group are known to flavonoids have been identified, many of which occur in nature. When glycosides are formed, the are responsible for their attractive colors of glycosidic linkage is normally located in flowers, fruits and leaves2. positions 3 or 7 and the carbohydrate can be L- Flavonoids occur as aglycones, glycosides and rhamnose, D-glucose, glucor-hamnose, galactose methylated derivatives. The flavonoid aglycone or arabinose6. Flavonoids are mainly divided into consists of a benzene ring (A) condensed with a seven major groups (figure-2)7. One of the best six membered ring (C), which in the 2-position described flavonoids, Quercetin is a member of carries a phenyl ring (B) as a substituent3. The this group. Flavonoids can be divided into various classes Corresponding Author: Dr. Parul Lakhanpal, Reader, Department of Pharmacology, SSR Medical College, Belle-Rive, Mauritius, Email: [email protected] 22 Internet Journal of Medical Update, Vol. 2, No. 2, Jul-Dec 2007 Clinical Knowledge Figure 1: Structures of the major classes of Flavonoid4 Figure 2: Major classes of Flavonoids7 Quercetin is found in abundance in onions, are mainly found in green and black tea and in broccoli, apples and berries. The second group is red wine, whereas, anthocyanins are found in flavanones, which are mainly found in citrus strawberries, other berries, grapes, wines and fruits. An example of a Flavonoid in this group is tea2. Flavonoid contents of different foods are naringinin. Flavonoids belonging to the catechins shown in Table-1. 23 Internet Journal of Medical Update, Vol. 2, No. 2, Jul-Dec 2007 Clinical Knowledge Table 1: Main groups of flavonoids, compounds and food sources Groups Compounds Food sources Quercetin Yellow onion, Curly kale, Kaempferol Leek, Cherry tomato, Flavonols Myricetin Broccoli, Apple, Green and Isorhamnetin black tea, Black grapes, Querctagetin Blueberry. Tangeretin Parsley, Celery, Capsicum Heptamethoxyflavone pepper. Nobiletin Sinensetin Quercetogetin Flavones Chrysin Apegenin Luteolin Disometin Tricetin Naringenin Orange juice, Grapefruit Eriodictyol juice, Lemon juice. Hesperetin Flavanones Dihydroquercetin Dihydrofisetin Dihydrobinetin Silibinin Cocoa, Cocoa beverages, Silymarin Chocolates. Flavanols Taxifolin Pinobanksin (+) Catechin Chocolate, Beans, Apricot, Gallocatechin Cherry, Grapes, Peach, Red Catechins (-) Epicatechin wine, Cider, Green tea, Black (Proanthocyanidins) Epigallocatechin tea, Blackberry. Epicatechin 3-gallate Epigallocatechin 3-gallate Daidzein Soy cheese, Soy flour, Soy Isoflavones Genistein bean, Tofu. Glycitein Cyanidin Blue berry, Blackcurrant, Delphinidin Black grapes, Cherry, Malvidin Rhubarb, Plum, Strawberry, Anthocyanins Pelargonidin Red wine, Red cabbage. Peonidin Petunidin Quercetin, the most abundant of the flavonoids many other flavonoids including the citrus (the name comes from the Latin –quercetum, flavonoids like rutin, hesperidins, Naringenin meaning oak forest, quercus oak) consists of 3 and tangeritin. It is widely distributed in the rings and 5 hydroxyl groups (Figure-3)8. plant kingdom in rinds and barks. Quercetin Quercetin is a member of the class of flavonoids itself is an aglycon or aglucone that does not called flavonoles and forms the backbone for possess a carbohydrate moiety in its structure. 24 Internet Journal of Medical Update, Vol. 2, No. 2, Jul-Dec 2007 Clinical Knowledge Quercetin is typically found in plants as glycone reconstituting membranes. These include lipases, or carbohydrate conjugates. Quercetin glycone proteases, DNA repair enzymes and conjugates include rutin and thujin. Rutin is also transferases12. known as Quercetin-3-rutinoside.Thujin is also known as quercitrin, Quercetin-3-L-rhamnoside Direct radical scavenging action: and 3-rhannosyl qurcetin. Onions contain Free radical production in animal cells can either conjugates of Quercetin and carbohydrate iso be accidental or deliberate. With the increasing rhamnetin including Quercetin-3-4’-di-o-beta acceptance of free radicals as common place and glucoside, isorhamnetin-4’-o-beta glucoside and important biochemical intermediates, they have Quercetin-4’-o-beta glucoside. been implicated in a large number of human diseases13,14. Quercetin acting as free radical scavengers was shown to exert a protective effect in reperfusion ischemic tissue damage15,16,17. Quercetin prevents free radical induced tissue injury by various ways. One way is the direct scavenging of free radicals. By scavenging free radicals, Flavonoid; particularly Quercetin can inhibit LDL oxidation in vitro18. This action protects against atherosclerosis. Inducible nitric oxide syntheses Inhibitory action: Quercetin results in a reduction in ischemia – 8 Figure-2 Molecular structure Quercetin reperfusion injury by interfering with inducible nitric oxide synthase activity19. Nitric oxide is MECHANISM OF ACTION: produced by several different types of cells Anti-oxidative action: including endothelial cells and macrophages. The best described property of Quercetin is its Although the early release of nitric oxide through ability to act as antioxidant. Quercetin seems to the activity of constitutive nitric oxide synthase be the most powerful flavonoids for protecting is important in maintaining the dilatation of the body against reactive oxygen species, blood vessels20, the much higher concentration of produced during the normal oxygen metabolism nitric oxide produced by inducible nitric oxide or are induced by exogenous damage9,10. One of synthase in macrophages can result in oxidative the most important mechanisms and the damage. In these circumstances the activated sequence of events by which free radicals macrophages greatly increase their simultaneous interfere with the cellular functions seem to be production of both nitric oxide and superoxide the lipid peroxidation leading eventually the cell anions. Nitric oxide reacts with free radicals, death. To protect this cellular death to happen thereby producing high damaging peroxynitrite. from reactive oxygen species, living organisms Peroxynitrite can directly oxidize LDLs resulting have developed antioxidant line of defense in irreversible damage to cell membranes. systems11. These include enzymatic and non- Quercetin causes scavenging of free radicals; enzymatic antioxidants that keep in check therefore can no longer react with nitric oxide, ROS/RNS level and repair oxidative cellular resulting in less damage21. Nitric oxide damage. The major enzymes, constituting the interestingly can be viewed as radical itself and first line of defence, directly involved in the can directly be scavenged by Flavonoids22. neutralization of ROS/RNS are: superoxide dismutase (SOD), catalase (CAT) and Xanthine oxidase inhibitory action: glutathione peroxidase (GPx) The second line of The xanthine oxidase pathway has been defence is represented by radical scavenging implicated as an important route in the oxidative antioxidants such as vitamin C, vitamin A and injury
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