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A Quest for Staunch Effects of Flavonoids Arabian Journal of Chemistry (2012) xxx, xxx–xxx King Saud University Arabian Journal of Chemistry www.ksu.edu.sa www.sciencedirect.com REVIEW A quest for staunch effects of flavonoids: Utopian protection against hepatic ailments Anju Dhiman a,*, Arun Nanda a, Sayeed Ahmad b a Department of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, Haryana, India b Bioactive Natural Product Laboratory, Department of Pharmacognosy & Phytochemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi 110062, India Received 2 September 2011; accepted 15 May 2012 KEYWORDS Abstract The role of flavonoids as the major red, blue and purple pigments in plants has gained Antioxidant; these secondary products a great deal of attention over the years. Flavonoids are polyphenols Flavonoids; and occur as aglycones, glycosides and methylated derivatives. Flavonoids are the main compo- Hepatoprotection; nents of a healthy diet containing fruits and vegetables and are concentrated especially in tea, apples Phenolic compounds and onions. Till date, more than 6000 flavonoids have been discovered, out of which 500 are found in free state. They are abundant in polygonaceae, rutaceae, leguminosae, umbelliferae and compos- itae. Flavonoids are powerful antioxidants. In addition to their role in nutrition, flavonoids possess many types of pharmacological activities, including anti-inflammatory, antioxidative, hepatoprotec- tive, vasorelaxant, antiviral and anticarcinogenic effects. The present review is focused on flavo- noids derived from natural products that have shown a wise way to get a true and potentially rich source of drug candidates against liver ailments. The present review initially highlights the cur- rent status of flavonoids and their pharmaceutical significance, role of flavonoids in hepatoprotec- tion, therapeutic options available in herbal medicines and in later section, summarizes flavonoids as lead molecules, which have shown significant hepatoprotective activities. ª 2012 King Saud University. Production and hosting by Elsevier B.V. All rights reserved. * Corresponding author. Address: Department of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, India. Tel.: +91 1262 393232; mobile: +91 9896436152. E-mail address: [email protected] (A. Dhiman). Peer review under responsibility of King Saud University. Production and hosting by Elsevier 1878-5352 ª 2012 King Saud University. Production and hosting by Elsevier B.V. All rights reserved. http://dx.doi.org/10.1016/j.arabjc.2012.05.001 Please cite this article in press as: Dhiman, A. et al., A quest for staunch effects of flavonoids: Utopian protection against hepatic ailments. Arabian Journal of Chemistry (2012), http://dx.doi.org/10.1016/j.arabjc.2012.05.001 2 A. Dhiman et al. Contents 1. Introduction . 00 2. Biochemical pathway for flavonoid biosynthesis . 00 3. Flavonoids in pharmaceuticals . 00 3.1. Flavonoids as anticancer agents . 00 3.2. Flavonoids as antibacterial agents . 00 3.3. Flavonoids as antiprotozoans. 00 3.4. Flavonoids as anti ulcer and gastroprotective agents . 00 3.5. Flavonoids as hepatoprotective . 00 3.6. Flavonoids on cardiovascular system: vasorelaxing effect . 00 3.7. Flavonoids as neuroprotective agents . 00 3.8. Flavonoids as anti-inflammatory . 00 3.9. Flavonoids as anti-diabetic agents . 00 3.10. Flavonoids as antioxidants. 00 4. Role of flavonoids in hepatoprotection . 00 5. List of different medicinal plants containing flavonoids reported for hepatoprotection. 00 6. Important flavonoids reported for hepatoprotection . 00 7. Conclusion . 00 References. 00 1. Introduction their structural patterns. However, laboratory and epidemiol- ogic studies have focused on six flavonoid subgroups: flavones, The flavonoids are a diverse group of polyphenolic compounds flavonols, flavan-3-ols (catechins), procyanidins, flavanones, widely distributed in the plant kingdom (Harborne and Wil- and isoflavones (Theodoratou et al., 2007). They also have liams, 2000). Flavonoids are nearly ubiquitous in plants and important roles in plant growth, reproduction, and pathogen are recognized as the pigments responsible for the colors of and predator resistance (Harborne and Williams, 2000). These leaves, especially in autumn (Saraf et al., 2007). Flavonoids are formed in plants and participate in the light-dependent contribute to the flavor and pigmentation of the fruits and veg- phase of photosynthesis during which they catalyze electron etables in the human diet (Timberlake and Henry, 1986). More transport (Middleton et al., 2000). than 6000 plant flavonoids have been described, and they have Flavonoids are present in plants either as aglycones or as gly- been classified into at least 10 chemical groups according to coside conjugates. Attached sugar moieties include D-glucose, 3' 5' 1 2' 8 4' 6' O 4' 2 8 1 1 7 O 8 2 1' O+ 2' 7 5' 2 3' 1' 7 1' 6 3 3' 2' 4 6' 5 6 3 4 OH 6 O 4' 5 3 OH 6' 5 4 5' O Anthocyanidins Isoflavones Dihydroflavanols 3 3' 1 2' 4' 2 4 8 O 2 8 1 3' 7 1 O 2 5' 5 1' 4' 2' 2' 7 6 6' 6 1' 3' 4 3 5' 1' 5 6 3 5 4 OH 6' O 6' 4' O 5' O Isoflavones Chalcones Dihydroflavonols Figure 1 Basic structure of various flavonoids and related compounds. Please cite this article in press as: Dhiman, A. et al., A quest for staunch effects of flavonoids: Utopian protection against hepatic ailments. Arabian Journal of Chemistry (2012), http://dx.doi.org/10.1016/j.arabjc.2012.05.001 A quest for staunch effects of flavonoids: Utopian protection 3 OH OH 4CL COOH PA C4H + 3H2C L CoSCoA HOOC NH2 malonyl-CoA HOOC HOOC CoSCoA 4-coumaryl-CoA phenylalanine cinnamic acid p-coumaric acid CHI geranyl phenylpropanoid pathway CHI OH OH HO R OH HO OH OH HO OH resveratrol HO O tetrahydrochalcone OH O stilbene OH trihydrochalcone OH H O OH flavan-4-ols HO O R chalcone chalcone CH2 OH R CHI OH OH CHI OH O HO O HO O OH aurones OH R' HO O HO O F3'H OH OHO eriodictyol OH R liquiritigenin OH H O OHO O F3H R R' naringenin flavanone IFS OH R OH OH F3H HO O IFS OH R' HO HO O R' HO O F3'H OH HO O OHO F3'5'H OH dihydrokaempferol OH OHO R=H, R'=OH: dihydroquercetin R=OH, R'=OH: dihydromyrcetin phlobaphenes R O 3-OH-flavanones OH (dihydroflavonols) Isoflavone FLS R=H: daidzein FLS R=OH: genistein R R R=H, R'=H: kaempferol OH OH IOMT R=H, R'=OH: quercetin R=OH, R'=OH: myrecetin HO O a-ORh O DFR R' DFR R' HO O OH OHO O-Glc-O-Rha flavonols Glc-OO R O flavonol glycosides OCH3 R OH R R OH OH 12'H HO O R 1 HO O HO O R' LCR R' HO O OH H O OHOH OH flavones OH R O flavan-3-ols OCH3 Flavan-3,4,-diols HO (leucoanthocyanidins) R IFR LDOX OH R HO O HO O OH R' HO O OH R O + R' OH OCH3 R HO OH OH OH 2'-hydroxy isoflavanone 3-OH-anthocyanidins HO O R' VR OH R OH DMID OCH3 OH OH HO O HO O c-OGl O R' OCH3 O O-Glc-O-Rha OH OCH3 O-Glc medicarpin OH condensed tannins anthocyanins isoflavonoids (proanthocyanidins) Figure 2 The major branch pathways of flavonoid biosynthesis. L-rhamnose, glucorhamnose, galactose, lignin, and arabinose protects against cancer and cardiovascular diseases (Hollman, (Ross and Kasum, 2002). The basic structure of various flavo- 2004). In addition to their role in nutrition, flavonoids possess noids and their related compounds are given in Fig. 1. They many types of pharmacological activities, including anti-inflam- are prominent components of citrus fruits (Kefford and Chan- matory, antioxidative, hepatoprotective, antiviral and anticar- dler, 1970) and other food sources (Herrmann, 1976) and are cinogenic effects (Chen et al., 2007). This class of compounds consumed regularly with the human diet. It is generally recog- has become increasingly popular in terms of health protection nized that an increased consumption of vegetables and fruits because they possess a remarkable spectrum of biochemical Please cite this article in press as: Dhiman, A. et al., A quest for staunch effects of flavonoids: Utopian protection against hepatic ailments. Arabian Journal of Chemistry (2012), http://dx.doi.org/10.1016/j.arabjc.2012.05.001 4 A. Dhiman et al. and pharmacologic activities (Watjen et al., 2005). Perhaps the chronically biliary obstruction (Mandal et al., 2007). Green most active area of flavonoid research at the present time is the tea, especially its major polyphenolic constituent, epigallocate- possible medicinal contribution that flavonoids make to human chin-3-gallate, has received much attention as a potential can- health (Stipcevic et al., 2006). The present review is focused to cer chemopreventive agent (Phosrithong and Ungwitayatorn, cover the current status of flavonoids and their pharmaceutical 2009). Medicinally important flavonoids, along with their significance, role of flavonoids in hepatoprotection, therapeutic pharmaceutical significance are discussed as follows: options available in herbal medicines containing flavonoids and phenolic compounds and chemically defined flavonoid mole- 3.1. Flavonoids as anticancer agents cules reported for hepatoprotection. Flavonoid and its derivatives possessing p-glycoprotein inhib- 2. Biochemical pathway for flavonoid biosynthesis itory effects may become candidates of effective agents in can- cer chemotherapy. The important mechanism by which Flavonoids constitute a relatively diverse family of aromatic flavonoids exert their in vivo chemoprotective effects is through molecules that are derived from phenyl and malonyl-coenzyme their inhibition of efflux transporters and metabolizing en- A, CoA; via the fatty acid pathway (Shirley, 2001). zymes, such as CYP i.e., cytochrome P-450 (Bansal et al., In the early steps of flavonoid biosynthesis elucidated by 2009). Detailed studies have revealed that quercetin exerted a Woo et al. (2005) with slight modifications, in Fig. 2, phenyl- dose-dependent inhibition of growth and colony formation.
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