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Antioxidant Properties of Phenolic Compounas Catherine A° R,Ceoevans, N,Cho,As J° @,,,Er and George Paganga

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Antioxidant Properties of Phenolic Compounas Catherine A° R,Ceoevans, N,Cho,As J° @,,,Er and George Paganga ] ~|||L'{I] [~ i[1[:]1 reviews Antioxidant properties of phenolic compounas Catherine A° R,ceoEvans, N,cho,as J° @,,,er and George Paganga There is currently much interest in phytochemicals as bioactive components of food. The roles of fruit, vegetables and red wine in disease prevention have been attrib- uted, in part, to the antioxidant properties of their constituent polyphenols (vitamins E and C, and the carotenoids). Recent studies have shown that many dietary polyphenolic constituents derived from plants are more effective antioxidants in vitro than vitamins E or C, and thus might contribute significantly to the protective effects in vivo. It is now possible to establish the antioxidant activities of plant- derived flavonoids in the aqueous and lipophilic phases, and to assess the extent to which the total antioxidant potentials of wine and tea can be accounted for by the activities of individual polyphenols. tudies on the free radical-scavenging properties of properties, including: vitamins C and E; selenium and flavonoids have permitted characterization of the ma- other mineral micronutrients; carotenoids; phytoestrogens; S jor phenolic components of naturally occurring phyto- allium compounds; glucosinolates and indoles; dithiol- chemicals as antioxidants. Furthermore, the commercial thiones; isothiocyanates; protease inhibitors; fibre; and development of plants as sources of antioxidants that can folic acid. These compounds may act independently or in be used to enhance the properties of foods, for both nu- combination as anti-cancer or cardioprotective agents by a tritional purposes and for preservation, is currently of variety of mechanisms. One such protective mechanism, major interest. Numerous epidemiological surveys have attributed to vitamins C and E and the carotenoids, is shown an inverse relationship between the intake of fruit, antioxidant (radical-scavenging) activity. vegetables and cereals and the incidence of coronary heart Recent work is also beginning to highlight the potential disease and certain cancers. Many constituents of these role of other phytochemical components, including the dietary components may contribute to their protective flavonoids, phenylpropanoids and phenolic acids, as im- portant contributing factors to the antioxidant activity of the diet (Ref. 1; see Table 1). The flavonoids are a Flavonol Flavone large class of compounds, ubiquitous in plants, and usually occurring as gly- cosides. They contain several phenolic hydroxyl functions attached to ring structures, designated A, B and C (Fig. 1). Structural variations within the rings subdivide the flavonoids into OH 0 OH 0 several families: • Flavonols (e.g. quercetin and kaempferol), with the 3-hydroxy pyran-4-one C ring. • Flavones (e.g. luteolin, apigenin and Flavan-3-ol Isoflavone chrysin), lacking the 3-hydroxyl group. • Flavanols (e.g. catechin), lacking the 2,3-double bond and the 4-one structure. • Isoflavones (e.g. genistein), in which OH 0 ~L~ the B ring is located in the 3 position on the C ring. OH These flavonoids often occur as gly- cosides, glycosylation rendering the Fig. 1. Structures of the flavonoids. The basic structure consists of the fused A and molecule less reactive towards free C rings, with the phenyl B ring attached through its 1' position to the 2-position radicals and more water-soluble, so of the C ring (numbered from the pyran oxygen). Types shown include: flavonols permitting storage in the vacuole. (3-hydroxyflavones) [e.g. quercetin (3,5,7,3',4'-hydroxyl) and kaempferol (3,5,7,4'- Common glycosylation positions are: hydroxyl)]; flavones [e.g. luteolin (5,7,3',4'-hydroxyl), apigenin (5,7,4'-hydroxyl) and the 7-hydroxyl in flavones, isoflavones chrysin (5,7,-hydroxyl)]; flavan-3-ols [e.g. catechin (3,5,7,3',4'-hydroxyl)]; and and dihydroflavones; the 3- and 7- isoflavones [e.g. genistein (5,7,4'-hydroxyl)]. hydroxyl in flavonols and dihydro- flavonols; and the 3- and 5-hydroxyl in 1 52 April 1997,Vol. 2, No. 4 © 1997 ElsevierScience Ltd PII S1360-1385(97)01018-2 reviews anthocyanidins2. The sugar most usually involved in the glycoside formation is glucose, although galactose, rhamnose, xylose and arab;nose also occur2, as well as disaccharides such as rutose. Antioxidant Sources ~tioxidant The flavonoid variants are all activity ~ related by a common biosyn- (mM) thetic pathway (Fig. 2), incorpo- rating precursors from both the shikimate and the acetate-mal- Vitamin E onate pathways 2. Further modi- fication occurs at various stages, resulting in alteration in the Anthocyanidins extent of hydroxylation, methy- Oenin Blac]~ grapes/red wine~ 1.8±0.02 lation, isoprenylation, dimeriza- Cyanidi~ Grapes, raspberries and strawberries. 4.4±0.12 tion and glycosylation (producing DeIphfnidin Aubergine skin: 4.4±0.11 O- or C-glycosides)3-6. F t~3.OIs Querce~in Onion, apple ski~, berries, black grapes, 4.7±0.10 Relationships between the tea and broccoli. structure and antioxidant Kaempferol EndiVe; leek, broccoli,grapefruit and tea 1.3±0.08 activity of phenols The chemical activities of Flavones polyphenols in terms of their Rnti~ Onion, apple skin; berries, black grapes, 2.4±0.12 reducing properties as hydrogen- teaandbroccoli. or electron-donating agents pre- Lute61~ Lemon, oIive, celery and red pepper. 2.1 + 0.05 dicts their potential for action as Chrysin Fruit Skin: 1.4 + 0.07 Apigenin Celery and parSIey, free-radical scavengers (ant;oxi- 1.5 _+ 0.08 dants). The activity of an Flavan.3-ols ant;oxidant is determined by: (Epi)catecl)m:~ BI~ck grapes/red wine 2.4 _+ 0.02 • Its reactivity as a hydrogen- Epigall0ca~c}/i~ Teas~ 3.8 +- 0.06 or electron-donating agent Epigallbcateehin gattate Teas: &8 +_ 0.06 (which relates to its reduction 4.9 ± 0.02 potential). • The fate of the resulting ant;oxidant-derived radical, Taxifolin Citrus fi'uit. 1.9 ± 0.03 which is governed by its ability Nat;turin Ci~rus fruit. 0.8 u 0.5 (n~iringenim7-rutinoside} to stabilize and delocalize the Naringenin Citrus fruit. li5 • 0;05 unpaired electron 7. Hesperidi~ Orange juice. t.0~ 0.03 • Its reactivity with other ant;oxidants. L4 } 0:08 • The transition metal-chelating potential. Theaflavins Polyphenols possess ideal struc- ~eaflavin. Blacktea. 2.9 ± 0.08 tural chemistry for free 4.7 _+ 0.16 radical-scavenging activities, and 4.8 + 0.19 have been shown to be more effec- TheaflaVin digallate Black tea. 6.2 +_ 0.43 tive ant;oxidants in vitro than vit- Hydr0xye ares " amins E and C on a molar basis s'9. acid White grapes, olive, cabbage and asparagus 1.3 + 0.01 This is exemplified by studies Ch ic acid Apple, pear, cherry, tomato and peach. 1.3 _+ 0.02 using pulse radiolysis to investi- Ferulie acid Grains, tomato, cabbage and asparagus 1.9 + 0.02 gate the interactions of the p-Coumarie acid ~ite grapes, tomato, cabbage and 2.2 ± 0.06 hydroxyl radical ('OH), azide radi- asparagus. cal (N3'), superoxide anion (O2"-), lipid peroxyl radical (LO0") and ~Measured as the TEAC (Trolox equivalent antioxidant activity) - the concentration of Trolox with model t-butyl alkoxyl radicals the equivalent anti0xidant activity of a 1 mM concentration of the experimental substance, (tBuO') with polyphenols, the rate constants of the reactions and the stability of the ant;oxidant radical 1°. In addition, the propen- the relative abilities of the compounds to scavenge free sity for metal chelation, particularly iron and copper, supports radicals. This can be assessed 12'13 by applying the chromo- the role ofpolyphenols as preventative ant;oxidants in terms of genic redox indicator ABTS "+, the radical cation of 2,2'- inhibiting transition metal-catalysed free radical formationn. azinobis(3-ethylbenzothiazoline-6-sulphonic acid). The anti° There is a hierarchy of flavonoid and isoflavonoid anti- oxidant activities (Table 1) relative to Trolox, the oxidant activities that is dependent on structure and defines water-soluble vitamin E analogue, are entirely consistent April 1997, VoL 2, No, 4 1 53 reviews of contributing hydroxyl groups by glycosylation Acetate-malonate ~O ~-....~/OH/ Shikimate pathway ~.....------~ _pat hway decreases the antioxidant activity. • For metal chelation, the two points of attachment of c JI C',nnh,s ' - Lignin transition metal ions to the flavonoid molecule are the TM H °H o-diphenolic groups in the 3',4'-dihydroxy positions in HO~..~ the B ring, and the ketol structures 4-keto, 3- hydroxy or 4-keto and 5- OH O / OH O hydroxy in the C ring of the OH O flavonols. However, it is Ohalcone likely that metals differ Dihydrochalcone with regard to chelation by polyphenols. Glycosylation HO~OH at all of these crucial hydroxyl positions influ- ences the antioxidant activ- ity of the flavonoids. This OH O is important when con- Flavone sidering the relationship between the antioxidant activity of the naturally H ~-~.~OH ~ HO. -.¢'..- .0. abundant glycosides and that of the aglycones. The half peak reduction potential (Ep/2) has also o- \ ,erocarpan been ascribed as a suitable (+)'Dihydr°flav°no°/ ~ ~ parameter for representing the scavenging activity of the flavonoids TM. This was rationalized on the basis .o.r o \ \ that both electrochemical oxidation and hydrogen- o. \ \ Ro,eno,d donating free radical-scav- enging involve the break- ing of the same phenolic / \ bond between oxygen and hydrogen, producing the phenoxyl radical and H', which consists of an elec- tron and an H ÷ ion. Thus a OH OH OH O flavonoid with a low value (-)-Epicatechin Anthocyanidin Flavonol for half peak reduction potential (i.e. <0.2 mV) is a Fig. 2. Inter-relationships between flavonoid classes=. Arrows indicate the principal biosynthetic good scavenger. The half routes. peak reduction potentials can be compared with the total antioxidant activity, with their structures. The structural arrangements im- measured as the Trolox Equivalent Antioxidant Capacity parting greatest antioxidant activity as determined from (TEAC), by applying the ABTS "÷ radical cation scavenging these studies are: assay.
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