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Summary

Phenolic compounds are secondary metabolites widely found in fruits, mostly represented by flavonoids and phenolic acids. The growing interest in these substances is mainly because of their antioxidant potential and the association between their consumption and the prevention of some diseases. The health benefits of these phytochemicals are directly linked to a regular intake and their bioavailability. Studies have shown the importance of the regular consumption of fruits, especially for preventing diseases associated with oxidative stress. In the present review, the most recent articles dealing with polyphenols in fruits are reviewed, focusing on their occurrence, main methods of extraction, quantification and antioxidant assays. In addition, the health benefits and bioaccessibility bioavailability of phenolic compounds in fruits are addressed.

Introduction
Phenolic compounds comprise a diverse group of molecules classified as secondary metabolites in plants that have a large range of structures and functions. They can be classified into water!soluble compounds "phenolic acids, phenylpropanoids, flavonoids and quinones# and water!insoluble compounds "condensed tannins, lignins and cell!wall bound hydroxycinammic acids# "$ispail et al., %&&'#. Phenolic compounds have been considered the most important, numerous and ubiquitous groups of compounds in the plant kingdom "(ac)k * Shahidi, %&&+#. These substances are synthesised during the normal development of the plant, as well as in response to different situations, such as stress and ,- radiation, among others "(ac)k * Shahidi, %&&+#. Phenolic compounds have an aromatic ring bearing one or more hydroxyl groups and their structure may vary from that of a simple phenolic molecule to that of a complex high!molecular mass polymer ".alasundram et al., %&&/#. These antioxidant compounds donate an electron to the free radical and convert it into an innocuous molecule. 0xidative stress can cause a series of degenerative illnesses in humans, such as cancer, multiple sclerosis, autoimmune disease and Parkinson1s disease, to name a few "Theriault et al., %&&/#. Studies have suggested that a diet rich in phenolic compounds could avoid the oxidative damage that leads to ageing and age!related diseases by scavenging the free radicals from cell metabolism "2urosumiet al., %&&3#. $egarding their biological effects "antioxidant, antiviral, antimicrobial, anti!tumour and antibacterial activities#, polyphenols are known to participate in protection against the harmful actions of reactive oxygen species "4uo et al., %&55#. The antioxidants present in fruits, such as phenolic acids, flavonoids, anthocyanins and tannins, among others, have been frequently associated with health benefits "6u et al., %&55#. 7istorically, 8fruits have been considered a rich source of some essential dietary micronutrients and fibres, and more recently they were recognised as being an important source of a wide array of phytochemicals that individually, or in combination may benefit health1 "9ahia, %&&:#. This review focuses on presenting recent studies about phenolic compounds in fruits. ; brief overview of the research on polyphenols in fruits is presented. Their occurrence, their main methods of analyses and an evaluation of their antioxidant properties using different in vitro and in vivo techniques are addressed. 6inally, the health benefits and the bioavailability bioaccessibility of the phenolic compounds in the human body are discussed.

Research on phenolic compounds in fruits

The research on phenolic compounds in fruits has evolved considerably over the last %& years "6ig. 5#. The role of phenolic compounds in foods, especially in fruits, has drawn the attention of researchers all over the world, and a large number of reviews and books have been published about this topic "$obards et al., 5:::< 2aur * 2apoor, %&&5< .alasundram et al., %&&/< ;ndr=s!4acueva et al., %&&:< .elit) et al., %&&:< >l ?harras, %&&:< Ignat et al., %&55#. ;pproximately, @%++ articles on the topic of phenolic compounds in fruits were published from 5::5 to %&55.

Figure 1. (umber of publications on the topic of phenolic compounds in fruits produced in two decades "database searched %& 6ebruary %&5%#. Aata SourceB certain data included herein are derived from the Ceb of Science
D

prepared by Thomson $eutersD, Inc. "ThomsonD#, Philadelphia, P;, ,S;BEFopyright Thomson $eutersD %&5%. ;ll

rights reserved "out of a total of @%++ articles#. The progressive increase in the number of publications "+&!fold from 5::5 to %&55# evaluating polyphenols in fruits as the main topic mostly reflects the great interest in studying these compounds worldwide. The ,nited States, Spain, Italy, Fhina and .ra)il stand out as the top five countries around the world where research on polyphenols in fruits has become prominent "6ig. %#. The research is mainly focused onB "i# determination of total phenolic, flavonoid and anthocyanin contents, "ii# evaluation of different types of extraction "liquidGliquid, solidG liquid and supercritical fluid, "iii# investigation of the biological activity of polyphenols against some key diseases and microorganisms, "iv# evaluation of their total antioxidant capacity using several different chemical methodsB "5,5!diphenyl!%!picrylhydra)yl radical "APP7H#, oxygen radical absorbance capacity "0$;F#, %,%I!;)ino!bis"@! ethylben)othia)oline!/!sulphonic acid# ";.TS#, ferric reducing antioxidant power "6$;P#, trolox equivalent antioxidant capacity "T>;F#, J!carotene linoleic acid, etc.#, "v# the quantification and identification of polyphenols by spectrophotometric methods and high efficiency liquid chromatography "7P4F# using different detectors ",- -is, KS, >4SA, etc.#, and "iv# study of bioaccessibility and bioavailability of polyphenols.

Figure 2. Share of publications about phenolic compounds in fruits among the top ten countries to publish such studies "database searched %& 6ebruary %&5%#. Aata SourceB certain data included herein are derived from the Ceb of ScienceD prepared by Thomson $eutersD, Inc. "ThomsonD#, Philadelphia, P;, ,S;B EFopyright Thomson $eutersD %&5%. ;ll rights reserved.

Classification and chemical structure of phenolic compounds

Phenolic compounds make up a large and fascinating family of substances "-ermerris * (icholson, %&&/#. 6ruits contain considerable levels of bioactive compounds that impart health benefits beyond basic nutrition "2aur * 2apoor, %&&5#. The amount of phenolic compounds in fruits is strongly dependent on the degree of ripeness, variety, climate, soil composition, geographic location and storage conditions, among other factors ".elit) et al., %&&:#. They are mainly classified according to the number of phenol rings they contain "phenolic acids, stilbenes, flavonoids, lignans and tannins#. ;ll these substances have one or more hydroxyl groups directly linked to an aromatic ring characterising thus the phenolic structure "-ermerris * (icholson, %&&/#. In the case of the flavonoids group, when they are linked to one or more sugar molecules they are known as flavonoid glycosides, and when they are not connected to a sugar molecule they are called aglycones "Cilliamson, %&&+#. The degree of glycosylation directly affects the antioxidant capacity of flavonoids. ,sually, the aglycone forms of myricetin and quercetin are more active than the glycoside form "7opia * 7einonen, 5:::< 2aur * 2apoor, %&&5#. The flavonoids are the main bioactive compounds found in fruits and are distributed into six subclassesB flavonols, flavanones, isoflavones, flavan!@!ols, flavones and anthocyanins. 6lavonoids account for approximately two!thirds of the dietary phenols "$obbins, %&&@# and they are mostly present as glycosides, and partly as esters, rather than as free compounds "-ermerris * (icholson, %&&/< .elit) et al., %&&:#. The per capita consumption of the six flavonoid subclasses in the ,nited States is estimated to be 5L:.3 mg dayM5, being mainly flavan!@!ols "Fhun et al., %&&3#. 6lavonoids or bioflavonoids are widely distributed in fruits and they are recognised as being natural antioxidants< over '&&& flavonoids have been identified to date "4ampila et al., %&&:#. These substances have apparent roles in plant stress defence, such as in the protection against damage caused by pathogens, wounding or excess ,light "Cinkel!Shirley, %&&%#. The term flavonoid is usually used to describe a broad collection of natural products that include a F/!F@!F/ carbon framework or, more precisely, phenylben)opyran functionality "Karais et al., %&&/#, and they constitute most of the yellow, red and blue colours in fruits "4ampila et al., %&&:#. These phytochemicals were found to be very effective scavengers of free radicals in in vitro tests and they are important antioxidants because of their high redox potential and their ability to chelate metals "Tsao * 9ang, %&&@< >l ?harras, %&&:< Ignat et al., %&55#. The second most important group of phytochemicals comprises the phenolic acids, which account for almost the remaining third of the dietary polyphenols, and which are present in fruits in a bound form. These substances are divided into two subgroupsB hydroxyben)oic and hydroxycinnamic acids. In contrast to other phenolic compounds, the hydroxyben)oic and hydroxycinnamic acids present an acidic character owing to the presence of one carboxylic group in the molecule ";nnie * Nean!Nacques, %&&@#. 7ydroxycinnamic acid compounds are mainly present as derivatives, having a F/!F@ skeleton. 6erulic acid, p-coumaric acid and caffeic acid are some examples of this class. 7ydroxyben)oic acids "F/!F5# are found in various fruits and mostly occur as esters. The most common phenolic acids found in fruits in this category are gallic, vanillic, ellagic and syringic acids. Tannins are the third class of polyphenols that are found in fruits and are mostly present as phenolic polymers. Tannins are astringent and bitter substances of different molecular weights, and some of them, especially the hydrolysable tannins, are soluble in water. They are a group of polyhydroxy!flavan!@!ol oligomers and polymers with carbonGcarbon linkages between flavanol subunits "Schofield et al., %&&5#. Tannins have the ability to

precipitate proteins. The two main types of tannins are condensed and hydrolysable. ?allotannin or tannic acid is a type of hydrolysable tannin found in fruits. Fondensed tannins "proanthocyanidins# are the maOor phenolic compounds found in grapes. Proanthocyanidins, when in contact with salivary proteins, are responsible for the astringency of fruits ">l ?harras, %&&:#. Stilbenes are a group of phenylpropanoid!derived compounds characterised by a 5,%!diphenylethylene backbone "F/!F%!F/# "?oyal et al., %&5%#. 4ow quantities of stilbenes are present in the human diet, and their main representative is resveratrol, mostly in the glycosylated form "Aelmas et al., %&&/< Ignat et al., %&55#. $esveratrol is a phytoalexin. This substance is mainly produced in grapevines in response to inOury and fungal infection ";tanackoviPet al., %&5%#, and the main dietary source of resveratrol in fruits is found in red grape skins. Several studies have indicated that resveratrol has the ability to prevent cancer and coronary, neurological and degenerative diseases ";nekonda, %&&/< Saiko et al., %&&L< Aas * Aas, %&5&< ?resele et al., %&55#. $esveratrol present in red wine is directly linked to the 6rench paradox, in which 6rench people suffer a relatively low incidence of coronary heart disease even though they have a diet relatively rich in saturated fats "6erriQres, %&&+#. 6urthermore, the incidence of heart infarction in 6rance is about +&R lower than in the rest of >urope "$enaud * Aelorgeril, 5::%< Saiko et al., %&&L#. It is believed that the continuous and moderated ingestion of grape!derived products, especially red wine, plays a key role in preventing heart disease. The fifth group of polyphenols comprises the lignans, a large variety of individual structures mostly consisting of two phenylpropanoid moieties connected via their side chain FL carbons "Aavin * 4ewis, %&&@< ;ehle et al., %&55#, usually occurring as glycosides. 4ignans are one of the maOor classes of phytoestrogens, which are oestrogen!like chemicals. In the gastrointestinal tract, these molecules are converted into compounds "enterodiol and enterolactone# that have both oestrogenic and anti!oestrogenic properties "Keagher * .eecher, %&&&#. 6ruits are not the main dietary source of lignans in food and low concentrations are found in strawberries and cranberries "Keagher * .eecher, %&&&#. The highest amount of these chemical compounds is found in flaxseed. ;ccording to data from the 6ood Fomposition Panel of the Spanish Kinistry of >nvironment and $ural and Karine ;ffairs, the average intake of lignans from fruits and vegetables is estimated to be %@@./ Sg dayM5 "Koreno! 6ranco et al., %&55#. The composition of phenolic compounds in fruits varies considerably. 6ruits are a particularly rich source of flavonoids "especially flavonols, flavan!@!ols and anthocyanins# and hydroxycinnamic and hydroxyben)oic acids. ;s previously stated, a large amount of scientific evidence shows that the regular consumption of fruit is directly linked to the prevention of various diseases, and the maOority of polyphenols that might account for this are shown in Table 5. Table 1. Main dietary source of polyphenols in fruits

E traction of polyphenols
The extraction of phenolic compounds is influenced by several parameters, and the initial step of a preliminary experiment is to select the most appropriate extraction conditions. Sample preparation plays an important role in the quantification of phytochemicals from plant material, and it is the first and usually the most important process, which greatly influences the repeatability and accuracy of the analysis "Thao et al., %&55#. To achieve maximum extraction, it is recommended that several different parameters are tested, such as the solvent, agitation, extraction time, solute solvent ratio, temperature, efficiency of mass transfer and particle si)e, for example "4uthria, %&&L<7urtado!6ernande) et al., %&5&< 7aminiuk et al., %&55< 9ang et al., %&55#. Ideally, the extraction of polyphenols should be performed using fresh fruit samples. 7owever, because of seasonality, perishability, shelf! life and quality, many researchers have used free)ing and drying processes to preserve the plant material. These processes are often a necessary step for preserving the fruit sample against different types of degradation, for avoiding microorganisms and for concentrating the antioxidant compounds. Some authors have reported that the free)ing process and long!term fro)en storage cause important losses in the amount of phenolic compounds and vitamins found in fruits "de ;ncos et al., %&&&< Fhaovanalikit * Crolstad, %&&+< Turkben et al., %&5&#. Aifferent techniques are available to preserve plant material, and in the last few years, lyophilisation has been widely used. 4yophilisation is a process that removes the water from materials such as foods, drugs and biological samples, and it has been recognised as an important and well!established technique for improving the long!term stability of a product "2asper * 6riess, %&55#. In the literature, several authors have reported the use of lyophilisation as a drying technique for preserving fruit samples "Karques et al., %&&3, %&&:<7urtado! 6ernande) et al., %&5&< de Torres et al., %&5&< Ignat et al., %&55< 2otikova et al., %&55< $ockenbach et al., %&55#. The utilisation of finely powdered plant material enhances the extraction of phenolic compounds by increasing the surface area of the sample and promoting disruption of the plant cell wall "2im * 4ee, %&&5#. Chen the fruit sample is obtained "fresh, fro)en, dried or lyophilised#, the next stage is extraction, per se. The most commonly used step for extracting phenolic compounds in fruits is the use of organic solvents. The choice of the most appropriate solvent depends on its selectivity, miscibility, density, recovery, price, vapour pressure, viscosity and chemical and thermal stability. -arious solvents and conditions have been used to achieve optimal extraction. The application of acidified methanol, ethanol, acetone and ethyl acetate, and the combination of these solvents with water, has been widely reported in the literature "4uthria * Pastor!Forrales, %&&/<Aurling et al., %&&3< 4uthria, %&&L< Cang et al., %&&La< $ussell et al., %&&:a< ;nnegowda et al., %&5%< 7aminiuk et al., %&55< Prasad et al., %&55< $amful et al., %&55#. SolidGliquid extraction "S4># is an important, simple and efficient technique of mass transfer used for the recovery of polyphenols from fruit tissues. It allows soluble components to be removed from the plant matrix and these compounds migrate into the solvent up to the point of equilibrium "Forrales et al., %&&:#. This process can be improved by changing the concentration gradients, the boundary layer and diffusion coefficients "Forrales et al., %&&:< Ignat et al., %&55#. In addition, to enhance the extraction process, some authors have combined the S4> technique with ultrasound. This method has been successfully used to extract bioactive compounds "7errera * de Fastro, %&&'< Ka et al., %&&:< Fasa))a et al., %&5&< Prasad et al., %&5&< Cang * Tuo, %&55#.

,ltrasound!assisted extraction is a quick and efficient method for extracting phenolic compounds from fruits "2im * 4ee, %&&5#, being an effective way of extracting analytes from different matrices in a shorter time than other extraction techniques "7errera * de Fastro, %&&'#. The increase in polyphenol extraction by this technique is because of the disruption of cell walls, a reduction in particle si)e and enhancement of the mass transfer of cell contents to the solvent, caused by the collapse of the bubbles produced by cavitation "Paniwnyket al., %&&5< $odrigues * Pinto, %&&3#. 0ne of the disadvantages of the solid!extraction process is the co!extraction of substances such as proteins, sugars and organic acids "Ignat et al., %&55# that might interfere in the quantification of polyphenols, especially with the 6olin!Fiocalteu method. To remove these interferences, the use of F5L Sep!Pak cartridges is highly recommended. This purification technique separates the non!polyphenolic substances from the polyphenolic extract of the fruit, producing more accurate results. In the last decade, the use of supercritical fluid extraction "S6># of bioactive compounds in fruits has been investigated and is gaining popularity. Farbon dioxide is the most commonly used fluid in S6> "Uuitain et al., %&&/#. This type of extraction is considered an emerging technology "Fasas et al., %&&:# and it presents some advantages over classic solvent extraction methods, because it is a more selective and less toxic technique ";lpendurada, %&&@#. 0ther advantages of S6> include free!solvent products and the prevention of oxidation during processing "-atai et al., %&&:< 7errero et al., %&5&#. 0ne disadvantage of this technique is the need for expensive equipment and high pressures, which increase the costs compared with conventional liquid extraction. Therefore, S6> will only be used when significant advantages overcome these disadvantages. -atai et al. "%&&:# showed that the pre!treatment of fruit samples with carbon dioxide "F0%# removed the non! polar substances, making the polar polyphenols more accessible in grapes and elderberries. 7owever, the amount of extracted anthocyanins in these fruits was not significantly influenced by S6>. In another study, S6> with F0% >t07 showed similar results for the total phenolic compounds "TPF# in guava seeds compared with the Soxhlet S4> method "Fastro!-argas et al., %&5&#. Supercritical carbon dioxide was successfully used to extract resveratrol from grape pomace by Fasas et al. "%&5&#. In this study, S6> with F0% >t07 "+&& bar and @' VF# presented the highest resveratrol recovery "+:.5& mg per 5&& g of dry sample# when compared with conventional extraction Wmethanol 7Fl "&.5R# for @& min in an ultrasonic bathX, where @.5& mg of resveratrol per 5&& g of dry sample was obtained.

!uantification of phenolic compounds by spectrophotometric techni"ues


6ruits are an important source of polyphenols in the human diet and the proper quantification of these substances is of fundamental importance. The main methodologies used to quantify the bioactive compounds in fruits, which are widely described in the literature, are the colorimetric method of 6olin!Fiocalteu that estimates the total polyphenols "TPF#, the aluminium chloride colorimetric assay that quantifies the total flavonoids "T6# and total anthocyanins "T;# estimated by the p7 differential method, which is based on the structural change of the anthocyanin chromophore between p7 values of 5.& and +.' "?ranato et al., %&5&< 7aminiuk et al., %&55#. Table % shows a brief summary of the total polyphenols, total flavonoids and T; in different fruits. Table 2. Summary of total phenolic compounds# fla$onoids and anthocyanins of different fruits as "uantified by spectrophotometric measurements

Fruit material

Sample

Sol$ent

Total phenolics Total fla$onoids Total anthocyanins

References

5. %. @. +. '. 6.
3. ;YaZ ;cerola .anana

mg ?;> 5&& gM5 of fresh weight. mg 5&& gM5 of fresh weight "expressed as cyanidin @!glucoside or malvidin!@!glucoside#.

mg F;> 5&& gM5 of fresh weight. mg of U> 5&& gM5 of fresh weight. mg ?;> lM5 of fresh weigh.

mg F> 5&& gM5 of fresh weight.

?;>, gallic acid equivalent< F;>, chlorogenic acid equivalent< U>, quercetin equivalent< F>, catechin equivalent. 6resh 6resh 6resh 6resh 6resh 6resh 6resh 6resh 4yophilised powder 6resh 6resh 6resh 4yophilised powder 6resh Kethanol acetone Kethanol acetone +'+.&&a 5&/@.&&a G &.3&d G @&.5/d +'./&f G &.+&d 555.&&b 5L.:&b &.&&b 5'@.@&b 5:.++b %3.@&b ::.&Lb &.&&b $ufino et al. "%&5&# $ufino et al. "%&5&# 2evers et al. "%&&3# Cang * 4in "%&&&# 7aminiuk et al."%&55# Solomon et al."%&&/# 0rak "%&&3# 2evers et al. "%&&3#

;cetone water acetic acid +3'.&&c Phosphate buffer >thanol Kethanol 7Fl Kethanol 7Fl %%/.&&a @+5+.&&e +/@.&&a %@+L.&&e

.lackberry Fambuci 6ig ?rape 2iwifruit

;cetone water acetic acid 55%.&&c

Kulberry

Cater

5'5'.:&a

%'&.5&d

4in * Tang "%&&3#

0range Plum $aspberry

;cetone water acetic acid %+@.&&c ;cetone water acetic acid @55.&&c Phosphate buffer %/3.&&a

/.5&d @.&&d G

&.&&b 5&%.&&b 5:3.%&b

2evers et al. "%&&3# 2evers et al. "%&&3# Cang * 4in "%&&&#

Strawberry

Cater

@/@.3&a

5+./&d

4in * Tang "%&&3#

,vaia

>thanol

@3@.+&e

'L.3%d

+.33b

7aminiuk et al."%&55#

The quantification of phenolic compounds is mainly carried out by spectrophotometric analysis. ?enerally, the visible region of the spectrum is used to quantify total phenolics, flavonoids and tannins, among other substances. The most common and widespread methodology used to quantify the total phenolic compounds in foodstuffs originated from the methodology developed in 5:%3 by 0tto 6olin and -intila Fiocalteu for the measurement of tyrosine "6olin * Fiocalteu, 5:%3< >veretteet al., %&5&#, and it was adapted in 5:/' by -ernon Singleton and Noseph $ossi for the evaluation of total phenolics in wine "Singleton * $ossi, 5:/'#. This methodology is based on chemical reduction by a mixture of tungsten and molybdenum oxides "Caterhouse, %&&5#. ,pon reaction with

phenols, a blue colour is produced, which absorbs light at 3/' nm ">verette et al., %&5&#. The intensity of light absorption at this wavelength is proportional to the concentration of phenols "Caterhouse, %&&5#. It is noteworthy that this reagent does not only measure total phenols but it will react with any reducing substance. 6or this reason, the total reducing capacity of a sample will be quantified and not only the level of phenolic compounds "Ikawa et al., %&&@#. The average time for this test is % h< however, this time can be reduced by heating the sample. The main disadvantage of heating is that it affects the reproducibility of the assay because heating causes instability of the blue colour over time "colour loss#. Several articles reporting the total phenolic composition of fruits estimated using the 6olin!Fiocalteu method "Singleton * $ossi, 5:/'<Singleton et al., 5:::# are available in the scientific literatureB kiwifruit "Sun! Caterhouse et al., %&&:#, grape "9ang et al., %&&:#, mango "Prasad et al., %&55#, pomegranate "Fristofori et al., %&55#, cranberry "F[t=et al., %&55#, banana, guava, peach and pear "Fontreras!Falderon et al., %&55#, lemon, orange, passion fruit, pitaya, plum, avocado and papaya "6u et al., %&55# and apple "Theng et al., %&5%#. In a recent study, a wide variation in the contents of the total phenolic compounds of sixty!two Fhinese fruits was found, where the total phenolic compounds ranged from 55.LL to 'L'.'% mg gallic acid equivalent "?;># per 5&& g, with a difference of +:!fold and a mean value of 35.L& mg ?;> per 5&& g "6u et al., %&55#. Pear "honey# and Fhinese date presented the lowest and the highest amounts of total phenolic compounds, respectively "6u et al., %&55#. 7igh contents of TPF can be found in fruitsB 5&/@ mg ?;> per 5&& g of fresh weight "6C# in acerola "$ufino et al., %&5&#, 5@/' mg ?;> per 5&& g of 6C in cambuci "7aminiuk et al., %&55#, 53:3 mg ?;> per 5&& g of 6C in camu!camu "?enovese et al., %&&L# and %5/3 mg ?;> per 5&& g of 6C in ;ndean blackberry "-asco et al., %&&L#. 6lavonoids are mainly accumulated in the outer tissue of fruits because their synthesis is stimulated by sunlight "Kanach et al., %&&+<$osa et al., %&5&#. The total flavonoid content in fruits is mainly estimated using the colorimetric method with aluminium chloride. In this methodology, the fruit extract is added in a methanolic solution of aluminium chloride at a determined concentration. In some methodologies, the extract is mixed with (a(0% before mixing with ;lFl@ "Sun et al., %&55#. ;fter a short period of time, the absorbance is measured and compared with a flavonoid standard "catechin, quercetin or rutin#. The disadvantage of this methodology is that it only gives an estimation of the total flavonoid content "Ignat et al., %&55#. (evertheless, this is a simple and efficient methodology for quantifying the total content of flavonoids in fruits and it can be very useful when more advanced equipment, such as 7P4F, is not available. The flavonoid concentration in fruits varies by many orders of magnitude and in most of fruits these compounds are present in the skin. .erries are in the group that presents one of the highest values of total flavonoids among fruit ",SA;, %&55#. .lueberry, among another nineteen .ulgarian fruits, was found to contain the highest amount of total flavonoids with 5:&.@ mg of catechin equivalent "F># per 5&& g of 6C, followed by sour cherry with 5@L./ mg F> per 5&& g of 6C "Karinova et al., %&&'#. ;nthocyanins are water!soluble glycosides of anthocyanidins "aglycones# "-ermerris * (icholson, %&&/#. These compounds are ben)opyrylium and flavylium salts ".elit) et al., %&&:#. They are divided into anthocyanidin aglycones "sugar free# and anthocyanin glycosides. These substances are particularly evident in flowers and fruit tissues. ;nthocyanin is derived from two ?reek words, anthos and kyanos, meaning flower and dark blue, respectively "7e * ?iusti, %&5&#. This class of phenolic compounds is recognised as being the most important

group of pigments in nature and they contribute to the attractive colours of fruits. ;nthocyanins are pigments dissolved in the vacuolar sap of the epidermal tissues of fruits, to which they impart a pink, red, blue or purple colour, and they exist in different chemical forms, both coloured and non!coloured, according to the p7 "Kouly et al., 5::+< Kanach et al., %&&+#. 0ver /@' anthocyanins have been identified in plants to date "Callace, %&&L< 7e * ?iusti, %&5&#, although only six are commonly foundB delphinidin, cyanidin, pelargonidin, malvidin, petunidin and peonidin. The p7 differential method is the most commonly and widely used assay for quantifying monomeric anthocyanins. This methodology measures the absorbance at two different p7 values, and it is based on the structural transformation of the anthocyanin chromophore as a function of p7 "?iusti * Crolstad, %&&5#. It was initially developed to evaluate pigments in strawberry Oam "Sondheimer * 2ertes), 5:+L#. The methodology has undergone some modifications over time "6uleki * 6rancis, 5:/L< Crolstad et al., 5:L%< ?iusti * Crolstad, %&&5#. In this methodology, basically the pigments reversibly change colour with a change in p7. The samples are diluted with aqueous p7 5.& and +.' buffers and absorbance measurements are made at the wavelength of the maximum absorbance of the p7 5.& solution "Crolstadet al., %&&'#. The p7 differential method is based on this reaction and the difference in the absorbance of the pigments at '%& nm is proportional to the pigment concentration. The results are mainly expressed on a cyanidin!@!glucoside basis. The group of cherries and berries has been extensively reported in literature as containing the fruits with the highest levels of anthocyanins per serving. .erries with red, blue or purple colours constitute one of the most important sources of these phytochemicals "2ahkonen et al., %&&@#. ?rapes are one of the maOor dietary sources of anthocyanins "Kuno)!>spada et al., %&&+#, being widely obtained from wine, Ouices and Oams, for example. Some hybrid grape cultivars can reach up to /&@ mg of anthocyanins per 5&& g of 6C "Ka))a, 5::'< 9ang et al., %&&:#. $aspberry, blackberry, blueberry, chokeberry and bilberry, among others, are very rich in anthocyanins. Plum and elderberry are also among the richest sources of anthocyanins in fruits ",SA;, %&55#.

Identification and "uantification of phenolic compounds by %&'C


4iquid chromatography is an important physical separation technique carried out in the liquid phase where a mixture of compounds can be easily and rapidly separated. $everse!phase high!performance liquid chromatography "$P!7P4F# is the main method used for the separation of phenolic compounds in plant!food material, in which the stationary phase is less polar than the mobile phase. The stationary phase is generally made up of hydrophobic alkyl chains, where there are three common chain lengthsB F+, FL and F5L"?u))eta, %&55#. Silica!bonded F5L columns are widely used to separate phenolic compounds. In $P!7P4F, the retention time of phenolic compounds is higher for substances that are less polar "myricetin, quercetin, kaempferol#< meanwhile, polar molecules are eluted more easily "gallic acid, protocatechuic acid, epigallocatechin#. 0wing to their chemical complexity and similarity, polyphenols in fruits are usually identified and quantified by $P! 7P4F using a gradient elution instead of the isocratic mode, where the mobile phase is generally a binary system "Kerken * .eecher, %&&&< 2im * 4ee, %&&5#. ,sually, gradient elution is carried out with high quality ultrapure acidified water "phosphoric, acetic, formic acids# as the polar solvent< meanwhile, acetonitrile and methanol are usually used as less polar solvents "2im * 4ee, %&&5#. ; small quantity of acid is added to the solvent system to suppress the ionisation of phenolic and carboxylic groups, which will improve certain parameters such as retention time and resolution "7\kkinen, %&&&#.

Polyphenols have a maximum absorbance "]max# in either the ultraviolet or visible regions and, thus, determination of the optimum absorbance for each substance plays an important role in the identification, quantification and accuracy of the analysis. The ultraviolet spectrum in the region of maximum absorbance of gallic acid, resveratrol and quercetin is shown in 6ig. @.

Figure (. Kaximum absorbance of "a# gallic acid G %35.3 nm, "b# resveratrol G @&/.% nm and "c# quercetin G @3&./ nm. 7igh!performance liquid chromatography systems can be equipped with a wide range of detectors "refractive index, fluorescence, electrochemical, light!scattering, mass spectrometric and ,- -is# "Thompson * 4o.rutto, %&&/#, which can be used to detect and quantify polyphenols with and without chromophore groups, depending on the methodology used. ;mong the different detectors available, ,- -is with a photodiode array is one of the most widely used to elucidate polyphenols in plant!based materials. The main advantage of diode array detectors "A;A# is that several results can be obtained from a single run, mainly because of its collection of ,- -is spectra "2im * 4ee, %&&5#, thereby increasing the throughput of the 7P4F. In addition, it is possible to determine the correct wavelength in one run, to detect multiple wavelengths and to evaluate peak purity, among others "Aionex, %&&@#. Sophisticated systems of liquid chromatography coupled with modern detectors such as ,P4F!A;A!KS KS "ultra!performance liquid chromatography!A;A!tandem mass spectrometry#, ,P4F!A;A >SI!KS "ultra! performance liquid chromatography!A;A and electrospray ionisation!mass spectrometry#, 7P4F!PA;!KS >4SA "7P4F!photodiode array!mass spectrometry and evaporative light!scattering detector#, ,7P4F!KS KS "ultra! 7P4FGtandem mass spectrometry# and 7P4F!>SI!T06 KS "7P4FGelectrospray ionisation!time of flight!mass spectrometry# are currently available, which are able to determine the chemical structure of a wide range of compounds. 7owever, these systems are still expensive, which generally limits access to these types of equipment by most researchers. In this context, the system of liquid chromatography coupled with A;A!,- -is is the most utilised, especially in the identification of phenolic compounds, because of its low cost, sensitivity, separation efficiency, flexibility and identification potential. ; compilation of recent papers published about the separation and identification of phenolic compounds in fruits using $P!7P4F!A;A ,-!-is is summarised in Table @.

Fruit material

Mobile phase (gradient)/flow rate (ml min1)

Column type and temperature ( C) Varian mnisphere! "18(#$0 % &.6 mm len'th, $ (m))#0

Wavelength ( ) nm

Ma!or "ompounds identified +lla'ic acid and (,)-

#eferen"es

Raspberry

A (0.1% phosphoric acid in water), B (methanol), 0.8

#80, *60 and $#0

catechin, (.)-epicatechin, 1a2obe2et al. (#003) /0ercetin and cyanidin :eochloro'enic acid, (.)epicatechin, r0tin and cyanidin' ;elebe2 < 4elli (#011b)

4weet cherry

A ($% 5ormic acid in water), B (acetonitrile)sol6ent A 607&0), 1.0

Bec2man 8ltrasphere! 94

#80, *16, *6$

"18 (#$0 % &.6 mm len'th, $ (m))#$ and $#0

=rape pomace

A (#% acetic acid in water), B (methanol), 0.8

A'ilent +clipse >9B! "18(#$0 % &.6 mm len'th, $ (m))*0 @erc2 Aichrospher! "18(#$0 % &.0 mm len'th, $ (m))&0 #?8

"hloro'enic acid, 'allic acid and (,)-catechin

4a'dic et al.(#011)

@an'o

A (0.$% acetic acid in water), B (methanol), 0.8

#$&, #80, *#0 and *6$

=allic acid, p-co0maric acid, ella'ic, man'i5erin Bassanet al. (#011) and r0tin

A (0.1% 5ormic acid in ;iwi5r0it waste acetonitrile), (B) acetonitrile)water)5ormic acid ($73#7*), 1,$ ChenomeneD! "18(#$0 % &.6 mm len'th, & (m))&$ #80, *#0 and *?0

"a55eic acid, phydroDybenEoic acid and syrin'ic acid

40n-Faterho0seet al. (#00 3)

4trawberry

A (&.$% 5ormic acid in water), ChenomeD! "18(#$0 % &.6 mm len'th, #80,*#0, *60 B (acetonitrile), 1.0 & (m))*0 and $#0

Croanthocyanidins, (,)catechin, p-co0maric acid sEmians2iet al. (#003) and pelar'onidin

Apple G0ice

A (acetic acid in # m@ sodi0m A'ilent HorbaD! 4B acetate, 5inal pB #.$$), B (acetonitrile), 1.0 A (0.1% 5ormic acid in water), B (80% acetonitrile in water), 1.0 A (acetic acid in water pB #.?&), B (acetonitrile), 0.8 A (#% acetic acid in water), B "18 "18(1$0 % &.6 mm len'th, $ (m))*?

#80, *#0 and *60

"hloro'enic acid, ca55eic acid, cinnamic acid

Iorres et al.(#011)

Bayberry G0ice

9iamonsil! "18(#$0 % &.6 mm len'th, $ (m))*0

*60 and $#0

J0ercetin, 2aemp5erol and cyanidin

Kan' et al.(#003)

=0a6a

ChenomeD A0na! "18(#$0 % &.6 mm #80, *#0 and len'th, $ (m))*8 *?0

R0tin, l0teolin, api'enin and 2aemp5erol

;0bolaet al. (#011)

=rape s2in (water)acetonitrile)acetic acid, ?87#07#), 1.0

Faters :o6a Cac2! "18(#$0 % &.6 mm len'th, $ (m))#0

#10L*60

J0ercetin, 2aemp5erol and myricetin

bre/0e-4lier et al.(#010)

$able %& 'ummary of the methodologies used for the separation and identifi"ation of phenoli" "ompounds in fruits by #()*(+C),-,/./) /is

The methods of extraction, separation and the analysis of phenolic compounds in plant!food material were recently reviewed "Ignat et al., %&55#. The applications and advances in the liquid chromatography analysis of polyphenols have evolved considerably over the years "2alili * de -illiers, %&55#< however, these advances are not considered in the present review.

)ntio idant acti$ity of fruits


Kany methods have been used to evaluate and compare the antioxidant activity of fruits owing to the complexity of the substrate analysed "2aur * 2apoor, %&&5< S)abo et al., %&&3#. The antioxidant capacity is mainly evaluated through chemical tests and more recently through a cell antioxidant test. The antioxidant activity using chemical methods is primarily evaluated throughB "I# hydrogen atom transfer methods "7;T# or "II# electron transfer methods ">T# "Prior et al., %&&'< .adarinath et al., %&5&#. 0$;F, lipid peroxidation inhibition capacity, total radical!trapping antioxidant parameter "T$;P# and ;.TS radical scavenging are the most commonly used hydrogen atom transfer methodologies, and T>;F, 6$;P and APP7H free radical scavenging are the main >T tests ".adarinath et al., %&5&#. These in vitromethodologies have been frequently used to estimate antioxidant activity in fruits. ;s these antioxidant assays are based on different mechanisms using different radical or oxidant sources ",SA;, %&5&#, the results obtained are expressed in different units and, therefore, cannot be directly compared ",SA;, %&5&#. ;ntioxidants are molecules that are able to inactivate free radicals and their action "7alliwell, 5::/< Aevasagayam et al., %&&+#, providing an important role in the body defence system against reactive oxygen species "(oipa et al., %&55#. Phenolic compounds are considered natural antioxidants, and fruits are very rich in these phytochemicals. The APP7H "5,5!diphenyl!%!picrylhydra)yl# assay is the one of the most popular methods used to evaluate antioxidant activity in fruits< it was originally introduced by Karsden .lois in 5:'L ".lois, 5:'L#. The principle behind this assay is based on scavenging of the stable APP7H by an antioxidant "reduction of APP7H to APP7%# "Kishra et al., %&5%#. The absorbance is monitored in the range of '5'!'%& nm "(oipa et al., %&55#, where the purple colour of the solution changes to yellow and a reduction in the absorbance is observed "Kishraet al., %&5%#. This antioxidant assay has been modified over the years ".rand!Cilliams et al., 5::'< Kensor et al., %&&5< Fhen et al., %&&'<Fhien et al., %&&3# because the original methodology was somewhat oversimplified "Kolyneux, %&&+#. This test was recently reviewed to standardise the protocols "Sharma * .hat, %&&:#. The main findings refer to the use of a '& SK APP7H solution in methanol or buffered methanol, because of the accuracy of spectrophotometric measurements. In addition, a time course of the inhibition process is also suggested. ; new approach for evaluating antioxidant capacity using the APP7H test in aqueous solution using surfactant aggregates or micelles was recently proposed by (oipa et al. "%&55#. It was found that the optimum micelle system for determining the antioxidant capacity is % mKcethyltrimethylammonium bromide "FT;.# in &.5 K acetate buffer "p7 +./#, and it was suggested that this new approach could be an alternative to the APP7H assay using methanol. Koreover, the test showed a shorter time of analysis because the rate constants observed in the micelle system were significantly faster than those in methanol. ;nother important assay that is widely used to evaluate the antioxidant capacity of fruits is the 0$;F test. The 0$;F assay measures the ability of antioxidants to protect proteins from damage by free radicals ";wika et al., %&&@#, and it is the only chemical method that takes free radical action to completion "Cang et al., %&&+#.

6urthermore, owing to its biological relevance to the in vivo antioxidant efficacy, the 0$;F is the preferred technique of some researchers ",SA;, %&5&#. This methodology was originally introduced by ?la)er "5::&# and it was modified by Fao et al. "5::@#. In the original methodology, J!phycoerythrin is used as an indicator protein, %,%I!a)obis"%!amidinopropane# dihydrochloride ";;P7# as a peroxyl radical generator, and trolox as a control standard, where the results are expressed as micromolar of trolox equivalent per litre or per gram of sample "Fao et al., 5::@< Prior et al., %&&'#. The 0$;F was improved in %&&5 because of limitations of J!phycoerythrin, such asB inconsistency from lot to lot, photobleaching and interactions with polyphenols "0uet al., %&&5#. The authors proposed the use of fluorescein as the fluorescent probe. Cater!soluble and fat!soluble antioxidant compounds can also be assayed by the method described by Prior et al. "%&&@# for hydrophilic "7!0$;F# and lipophilic 0$;F "4!0$;F#, respectively. 0ne disadvantage of the 0$;F method in comparison with other antioxidant tests is that it requires expensive apparatus ";wika et al., %&&@#. In a comprehensive study, over 5&& different kinds of foods were evaluated using the 0$;F test "Cu et al., %&&+#. ;mong the fruits assayed, the berries, plums and some varieties of apples gave higher values in the 0$;F test< these data were also confirmed in the ,SA; database for 0$;F of selected foods ",SA;, %&5&#. In this database, higher values of micromolar of trolox equivalent per gram of fruit were found for different berries and some other fruits such asB chokeberry, elderberry, black raspberry Ouice, raisins, raspberry and rose hip. Aespite the great popularity of chemical tests, these methodologies fail to effectively predict the antioxidant capacity in vivo. ; more relevant method called 8cellular antioxidant activity "F;;#1 was recently proposed to measure the cellular activity of antioxidants "Colfe * 4iu, %&&3#. This methodology considers important aspects such as uptake, metabolism and location of antioxidant compounds within cells "Song et al., %&5&#, which are not considered by traditional methods. This technique is performed using a %I,3I!dichlorofluorescin "AF67# probe in human hepatocarcinoma cells "7ep?%#, which fluoresce when oxidised by peroxyl radicals to %I,3I! dichlorofluorescein "Colfe et al., %&&L#. The F;; methodology was used to evaluate the inhibition of peroxyl radical!induced AF67 oxidation by selected pure phytochemical compounds and fruits by measuring the >F'& values "Colfe * 4iu, %&&3#. Uuercetin showed the highest F;; value among the pure compounds assayed, and blueberry was the most effective in preventing peroxyl radical!induced AF67 oxidation among the fruits. The same research group published another cellular antioxidant study where twenty!five fruits commonly consumed in the ,nited States were evaluated "Colfe et al., %&&L#. The group of berries "mainly blackberry# and pomegranate showed the highest values of F;;. 0n the other hand, bananas and melons showed the lowest values of F;;.

%ealth benefits of phenolic compounds


(on!communicable diseases "(FAs# are diseases of a long duration and generally a slow progression. ;mong (FAs, the four main types areB cancer, cardiovascular diseases "F-A#, chronic respiratory diseases and diabetes "C70, %&55#. It is estimated that (FAs are accountable for more than /@R of annual deaths in the world "C70, %&55#. It has been speculated that phenolic compounds, especially the group of flavonoids, contribute towards lowering the incidence of (FAs. Auring the last decade, the number of studies relating the beneficial effects of polyphenols in human health has significantly increased. >pidemiological studies have shown that the daily intake of plant!derived foods possibly prevents some types of cancer, particularly cancers of the gastrointestinal tract, F-A and even lowers the incidence of diabetes "4iu et al., %&&&< C70, %&&@, .a))ano et al., %&&L< Cang et al.,

%&5%#. In vitro tests have shown that phenolic compounds inhibit cancer cell proliferation, protect neurons, improve insulin secretion, reduce vascularisation and stimulate vasodilation "6erguson et al., %&&+< Silva et al., %&&L< ?eorge et al., %&&:< Ael $io et al., %&5&#. ;mong the common modifiable risk factors, unhealthy diets play an important role in (FAs. Several diseases are associated with unhealthy diets, which are characterised by a high intake of calories with absent or low nutritional value. 6ruits are of great interest as they are richer in phenolic compounds than vegetables "Scalbert * Cilliamson, %&&&< $inaldo et al., %&5&#. The protective effect from fruits can be attributed to multiple factors, including phytochemicals, micronutrients, fibre and other anti!carcinogenic substances "Fampbell et al., 5:::#. ;lthough there is evidence showing the beneficial effects of consuming fruits, data supporting a beneficial role of fruit and vegetable consumption against cancer are conflicting "Thompson, %&5&#. ; recent study involving '&& &&& people in >urope showed a very low association between the intake of fruits and vegetables and the reduction in cancer risk ".offetta et al., %&5&#. Aespite this, the ;merican 7eart ;ssociation recommends eating at least five servings of fruit and vegetables per day "4iu et al., %&&&#. This recommendation is reinforced by the Corld 7ealth 0rgani)ation "C70#, which recommends the intake of a minimum of +&& g of fruits and vegetables per day, excluding potatoes and starchy tubers "C70, %&&@#. ; wide range of studies has shown that the eating habits have an important impact on health, quality of life and longevity "6ra)ao, 5:::#. The interest in polyphenols of different fruits "natives or exotics# by different laboratories and research groups all over world has increased significantly during the last two decades. ;mong the polyphenols, flavonoids are the group of phytochemicals that have received the maOority of attention in research. They are alleged to have health!promoting effects because of their higher antioxidant activities "in vitrotests#, despite the fact that inconclusive evidence of in vivo antioxidant effects of flavonoids "7alliwell et al., %&&'# has been disclosed. Polyphenols are extensively metaboli)ed in the human body, resulting in a significant modification of the redox capacity of these substances "Cilliams et al., %&&+#. It has been reported that even after the extensive intake of flavonoids, the metabolites tend to have reduced antioxidant activity "7alliwell et al., %&&'#. The concentration of polyphenols can be 5&&G5&&& times lower in the human body "4PI, %&55#, rarely exceeding nK concentrations in plasma after normal dietary intake "Ael $io et al., %&5&#. In vivo tests have shown that these substances do not act as conventional hydrogen!donating antioxidants but they may exert modulatory actions in cells "Cilliams et al., %&&+#. ;fter an extensive literature review, .ritish scientists concluded that the concentration of flavonoids usually found in vivo is high enough to have pharmacological activity at receptors and on en)ymes and transcription factors "Cilliams et al., %&&+#. Aespite all of the evidence presented, conflicting or not, it is common sense that the consumption of plant!derived foods, especially fruits, is of fundamental importance for keeping the body in good health, especially foods rich in polyphenols. Studies have reported important health benefits of fruit consumption, including the anti!inflammatory effects of aYaZ, citrus, bilberry, grape and pomegranate ".enavente!?arcia * Fastillo, %&&L< Terra et al., %&&:, %&55< Kueller et al., %&5&< 2ang et al., %&55#, the antitumor effects of pomegranate and cranberry "9an et al., %&&%< (eto et al., %&&L< Sturgeon * $onnenberg, %&5&# and the anti!allergic properties of strawberry "Itoh et al., %&&:#, among other protective effects.

*ioaccessibility and bioa$ailability of antio idant compounds in fruits

; considerable number of studies describing the presence of many different types of bioactive compounds with antioxidant properties in fruits have been published over the last few years. 7owever, food scientists have only recently begun to evaluate the actual contribution of these bioactive compounds, such as active antioxidants, after their consumption. The ingestion of fruits containing a large amount of polyphenols is not usually correlated with highest concentrations of active metabolites of these polyphenols "capable of antioxidant effects# in the human body "Kanach et al., %&&+< Palafox!Farlos et al., %&55#. This can generally be explained by differences in bioaccessibility and bioavailability of polyphenols from fruits and other foods, which directly influence antioxidant effects in vivo "Kanach et al., %&&+< Palafox!Farlos et al., %&55#. The bioaccessibility and bioavailability of polyphenols from fruits and other foods can be defined asB "i# the amount of the antioxidant compound that is released from its food matrix after digestion, becoming available for intestinal absorption "7edren et al., %&&%< Kanachet al., %&&'# and, "ii# the proportion of the antioxidant compound that is absorbed "i.e. reaches the bloodstream# and becomes available for metabolic utilisation and exerts its effects at the site of action "Shi * 4e Kaguer, %&&&< Parada * ;guilera, %&&3< Taglia)ucchi et al., %&5&<Palafox! Farlos et al., %&55< $odrigo et al., %&55#, respectively. Therefore, bioaccessibility and bioavailability are distinct concepts and the bioavailability of polyphenols depends on their bioaccessibility from the food matrix "Kanach et al., %&&'< Parada * ;guilera, %&&3<Taglia)ucchi et al., %&5&#. 6ruits contain complex mixtures of polyphenols that are not evenly distributed throughout the peel, pulp and seeds. 6urthermore, these polyphenols are not all absorbed with equal efficiency "Kanach et al., %&&+#. Several factors can interfere with the release and or absorption of polyphenols from fruits. In summary, the main factors include the followingB

The chemical structure of polyphenols and their interactions with different macromolecules such as proteins and dietary fibres affect their assimilation and metabolic fate in vivo "6aulks * Southon, %&&'< Parada * ;guilera, %&&3< 9ang et al., %&&L< Palafox!Farlos et al., %&55#. Kost of the polyphenols in fruits exist as polymers or in glycosylated forms. The content of hydrolysable tannins and proanthocyanidins associated with dietary fibre and proteins in some fruits is about fivefold that of free polyphenols "-itaglione et al., %&&L< 6ogliano et al., %&55#. Fommonly, the aglycones, which only correspond to a small portion of the polyphenols in fruits, can be directly absorbed from the small intestine. Kost polyphenols in their native form "polymeric, glycosylated or esterified# must be en)ymatically hydrolysed before absorption "Calle, %&&+#. The type of sugar linked to a polyphenol as well as the degree of glycosylation affects the rate and extent of intestinal absorption ";rts et al., %&&+< A1;rchivioet al., %&5&#. ;cylation, conOugation, molecular si)e and solubility also determine the absorption and metabolism of fruit phenolics "Scalbert * Cilliamson, %&&&< 9ang et al., %&&L< 2oli et al., %&5&#. Polyphenols with a high molecular weight are predicted to be poorly absorbed "9ang et al., %&&L#. The slow elimination of quercetin metabolites from the body can be explained by the existence of intermolecular bonds between the metabolites and serum albumin "Kanach et al., %&&+#. The interactions of polyphenols with fibre "indigestible polysaccharides of plant cell walls# in the small intestine can lower their bioaccessibility and, consequently, bioavailability "Palafox!Farlos et al., %&55#. 7owever, these antioxidants may reach the large intestine and remain

in the colonic lumen, where they could contribute to a healthy antioxidant environment "Saura!Falixto et al., %&5&< Palafox!Farloset al., %&55#. In general, polyphenols associated with dietary fibre can be partially bioavailable, although the bioavailability of polyphenols is usually delayed by a high content of dietary fibre "Pere)!Nimene) et al., %&&:#. Fonversely, pectin might enhance the bioavailability of quercetin from rutin by altering the metabolic activity of the intestinal microflora or intestinal physiological functioning "Tamura et al., %&&3#. The role of dietary fibre in the absorption of antioxidants has been recently reviewed "Palafox!Farlos et al., %&55#.

6ruit processing affects polyphenol contents and alters fruit microstructure, resulting in the loss or enrichment of some polyphenols and influencing their access and availability "Scalbert * Cilliamson, %&&&< Kanach et al., %&&+< Parada * ;guilera, %&&3#. 6ruit peeling can result in the loss of a significant portion of some polyphenols. ;pple peels may present higher antioxidant and antiproliferative activities than the pulp "flesh# "Colfe et al., %&&@#, and flavonols are not usually found in peeled apples ".urdaet al., 5::&#. The peel of peach contains most of the flavonols and cyanidins in the fruit ";ndreotti et al., %&&L#. 7igher concentrations of resveratrol are found in red wines, which are fermented with the skin "peel#, than in white wines "2ing et al., %&&/#. Industrial fruit Ouices usually present low flavonoid contents, because flavonoids are frequently removed during clarification or stabili)ation processes "Kanach et al., %&&+#. The oxidative degradation of polyphenols can occur during fruit pulp processing as a result of the release and action of cytoplasmic polyphenol oxidase "Kanach et al., %&&+#. 0therwise, the maceration or pressing of fruits can result in the diffusion of antioxidant compounds in the Ouice, including the solubilisation of polyphenols from unconsumed parts of the fruits, such as skins and seeds "Scalbert * Cilliamson, %&&&< ?on)ale)!(eves et al., %&&+#. Tannins from grapes are mainly extracted during winemaking by pressing the fruit and during fermentation "especially in red wines#, where these polyphenols can be extracted from the insoluble matrix "7a)ak et al., %&&'< Parada * ;guilera, %&&3#. Suppression of the food matrix effect "reduction of the interaction between polyphenols and carbohydrate polymers# increases the bioavailability of polyphenols "Parada * ;guilera, %&&3#. The fermentation process in winemaking can result in the transformation of polyphenols from grapes or the formation of new structures "van de Ciel et al., %&&5< 6lamini, %&&@#, and the presence of ethanol in wine may contribute to their bioavailability "Authie et al., 5::L< $odrigo et al., %&55#.

The biological interactions between polyphenols and cells, en)ymes and proteins from the gastrointestinal system and colonic microflora play an essential role in their bioavailability. Kany polyphenols from fruits are only bioaccessible and bioavailable in the human body through the action of intestinal and hepatic en)ymes and also via colonic microflora. ;pproximately +LR of dietary polyphenols are bioaccessible in the small intestine and +%R become bioaccessible in the colon "large intestine# "Saura!Falixtoet al., %&&3#. These polyphenols are then absorbed and metaboli)ed. Kost of the biological activity of polyphenols from fruits is believed to be elicited in the human body by their secondary metabolites instead of the native compounds "2roon et al., %&&+<Aonovan et al., %&&/#. Several en)ymes in the human body are involved in the metabolism of polyphenols. The specificity and location of the en)ymes can regulate absorption of the polyphenols. 0ne of the first steps in the metabolism of most glycosylated antioxidant compounds is the removal of sugars by en)ymes. Polyphenols attached to glucose

are potential substrates for human J!glucosidases, but those attached to rhamnose are not cleaved by J! glucosidases and depend upon the action of rhamnosidases produced by colonic microflora "Scalbert * Cilliamson, %&&&#. Polyphenols in the free form "aglycones# can be conOugated in the small intestine and later in the liver by glucuronidation, methylation, sulphation or a combination of these. FonOugation deconOugation reactions of polyphenols are mainly carried out by en)ymes such as cytosolic J!glucosidase "F.?# and lactase phloridi)in hydrolase "4P7#, which are mainly located in the epithelial cells of the small intestine, and catechol!O! methyltransferase "F0KT#, ,AP glucuronosyl transferase ",AP?T# and phenol sulphotransferases "P!PST#, which are located in many different tissues "Scalbert * Cilliamson, %&&&#. The conOugation reactions significantly interfere with the metabolic fate of polyphenols "Kanach et al., 5::L< Scalbert * Cilliamson, %&&&< Fano et al., %&&%#, either producing active metabolites or increasing the excretion rate of some polyphenols "A1;rchivio et al., %&5&#. The aglycones are either absent in blood or present in low concentrations "Scalbert * Cilliamson, %&&&#. The polyphenols that are not absorbed in the small intestine can reach the colon where they can be metaboli)ed by the colonic microflora "A1;rchivio et al., %&5&#. The colonic microflora hydrolyses glycosides into aglycones and also degrades them into phenolic acids ";ura et al., %&&'< A1;rchivio et al., %&5&#. >sterified hydroxycinnamic acids require the action of esterases of the colonic microflora for the cleavage of ester bonds because there are no esterases in human tissues. The metabolism of chlorogenic acid is dependent upon the action of en)ymes produced by colonic microflora "Plumb et al., 5:::< Scalbert * Cilliamson, %&&&#. The colonic biotransformation of polyphenols was recently reviewed by van Auynhoven et al. "%&55#. Some experimental procedures used to predict and evaluate the bioaccessibility and or bioavailability of polyphenols in vitro "digestive en)ymes, Faco!% cells, gastrointestinal and colonic model systems# and in vivo "either in humans or in animals# are reported in the studies conducted by 6ogliano et al. "%&55#, Taglia)ucchi et al. "%&5&#, Filla et al. "%&&L, %&&:#, Saura! Falixto et al. "%&&3#, .ermude)!Sotoet al. "%&&3# and 2oli et al. "%&5&#, and Serra et al. "%&5&#, .orges et al. "%&5&#, Pere)!Nimene) et al. "%&&:# and -itaglione et al. "%&&L#, respectively. 6inally, to understand the real contribution to human health by ingesting polyphenols and also to develop food products with relevant antioxidant properties, it is important to consider the amount, the chemical structure and the source of polyphenols as well as the biological interactions that polyphenols might have with macromolecules, cells, en)ymes and colonic microflora. ;ll of these factors affect the absorption, tissue concentration, metabolic fate and action of polyphenols as antioxidants in promoting health benefits.

Conclusions
Phenolic compounds are a fascinating and unique class of bioactive compounds widely spread throughout nature. Studies about polyphenols have increased exponentially over the last two decades, mainly because of the association between the consumption and health benefits of these substances. 6ruits are excellent sources of phenolic compounds, which impart health benefits beyond basic nutrition. The extraction, isolation and quantification of polyphenols in fruits still present a challenge. Therefore, the search for new methodologies is essential for better understanding this class of phytochemicals. In addition, the establishment and consolidation of databases of polyphenols are of great importance because they are key in assisting epidemiological

investigations. The absorption mechanisms of phenolic compounds are still not well established. 6urther investigations are necessary to better understand the bioaccessibility bioavailability of polyphenols, focusing on the action of colonic microflora on the metabolism and bioavailability of several polyphenols, the biological properties of conOugated polyphenols and active metabolites besides aglycones and parent compounds, the effect of dietary fibre on polyphenol absorption.

)c+no,ledgments
The authors thank the (ational Founcil for Scientific and Technological Aevelopment "F(Pq< Process (umber '&5'@' %&&:!L# for financial support.

References
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@3.

5. %. @. @L.

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5. %.

PubKed, F;S Aionex (%&&@). *%2-455 *hotodiode 2rray %etector Operator6s $an'al. 1'nnyvale, C2, ,12# %ione+ Corporation.

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5. '5.

Fross$ef Aurling, (.>., Fatchpole, 0.N., ?rey, N... et al. (%&&3). >xtraction of phenolics and essential oil from dried sage "Salvia officinalis# using ethanol!water mixtures. 6ood Fhemistry, 131, 5+535+%+.

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;bstract 6ull ;rticle "7TK4# PA6"/+L2# $eferences Ceb of ScienceD Times FitedB : >verette, N.A., .ryant, U.K., ?reen, ;.K., ;bbey, 9.;., Cangila, ?.C. & Calker, $... (%&5&). Thorough study of reactivity of various compound classes toward the 6olin!Fiocalteu reagent. Nournal of ;gricultural and 6ood Fhemistry, 0/, L5@:L5++.

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;bstract 6ull ;rticle "7TK4# PA6"'''2# $eferences Ceb of ScienceD Times FitedB :+ 6ogliano, -., Forollaro, K.4., -itaglione, P. et al. (%&55). In vitro bioaccessibility and gut biotransformation of polyphenols present in the water!insoluble cocoa fraction. Kolecular (utrition * 6ood $esearch, 00, S++S''. Airect 4inkB

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Fross$ef, F;S, Ceb of ScienceD

//.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB 5 ?oncalves, ;., 4aOolo, 6.K. & ?enovese, K.I. (%&5&). Fhemical composition and antioxidant antidiabetic potential of .ra)ilian native fruits and commercial fro)en pulps. Nournal of ;gricultural and 6ood Fhemistry, 0/, +///+/3+.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB 3 ?on)ale)!(eves, ?., Fharamelo, A., .alado, N. et al. (%&&+). Phenolic potential of Tannat, Fabernet! Sauvignon and Kerlot grapes and their correspondence with wine composition. ;nalytica Fhimica ;cta, 01(, 5:55:/.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB '5 ?oulas, -. & Kanganaris, ?.;. (%&5%). >xploring the phytochemical content and the antioxidant potential of Fitrus fruits grown in Fyprus. 6ood Fhemistry, 1(1, @:+3.

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3:.

?ranato, A., 2atayama, 6.F.,. & de Fastro, I.;. (%&55). Phenolic composition of South ;merican red wines classified according to their antioxidant activity, retail price and sensory quality. 6ood Fhemistry, 121, @//@3@.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB 3 ?resele, P., Ferletti, F., ?uglielmini, ?., Pignatelli, P., de ?aetano, ?. & -ioli, 6. (%&55). >ffects of resveratrol and other wine polyphenols on vascular functionB an update. Nournal of (utritional .iochemistry, 22, %&5%55.

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7alliwell, .. (5::/). ;ntioxidantsB the basics!what they are and how to evaluate them. In# 2dvances in *harmacology (edited )y 7. Sies). *p. @%&. 1an %iego, C2, ,12# 2cademic *ress.

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7alliwell, .., $after, N. & Nenner, ;. (%&&'). 7ealth promotion by flavonoids, tocopherols, tocotrienols, and other phenolsB direct or indirect effects` ;ntioxidant or not` The ;merican Nournal of Flinical (utrition, /1, %/LS%3/S.

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PubKed, F;S, Ceb of ScienceD Times FitedB 5%3 7aminiuk, F.C.I., Plata!0viedo, K.S.-., ?uedes, ;.$., Stafussa, ;.P., .ona, >. & Farpes, S.T. (%&55). Fhemical, antioxidant and antibacterial study of .ra)ilian fruits. International Nournal of 6ood Science and Technology, .2, 5'%:5'@3. Airect 4inkB

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;bstract 6ull ;rticle "7TK4# PA6"L'@2# $eferences Ceb of ScienceD 7assan, 6.;., Ismail, ;., ;bdulhamid, ;. & ;)lan, ;. (%&55). Identification and quantification of phenolic compounds in .ambangan "Kangifera paOang 2ort.# Peels and their free radical scavenging activity. Nournal of ;gricultural and 6ood Fhemistry, 01,:5&%:555.

5. %.

Fross$ef, F;S,

@. L3.

Ceb of ScienceD 7a)ak, N.F., 7arbertson, N.6., ;dams, A.0., 4in, F.7. & $o, ..7. (%&&'). The phenolic components of grape berries in relation to wine composition. Proceedings of the Seventh International Symposium on ?rapevine Physiology and .iotechnology, 2/1, 5L:5:/.

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F;S 7e, N.;. & ?iusti, K.K. (%&5&). ;nthocyaninsB natural colorants with health!promoting properties. ;nnual $eview of 6ood Science and Technology, 1, 5/@5L/.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB @5 7edren, >., Aia), -. & Svanberg, ,. (%&&%). >stimation of carotenoid accessibility from carrots determined by an in vitro digestion method. >uropean Nournal of Flinical (utrition, 02, +%'+@&.

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Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB // 7errera, K.F. & de Fastro, K.A.4. (%&&'). ,ltrasound!assisted extraction of phenolic compounds from strawberries prior to liquid chromatographic separation and photodiode array ultraviolet detection. Nournal of Fhromatography ;, 1133, 53.

5. %. @. +. :5.

Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB @3 7errero, K., Kendiola, N.;., Fifuentes, ;. & Ibane), >. (%&5&). Supercritical fluid extractionB recent advances and applications. Nournal of Fhromatography ;, 121-, %+:'%'55.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB @3 7opia, ;. & 7einonen, K. (5:::). ;ntioxidant activity of flavonol aglycones and their glycosides in methyl linoleate. Nournal of the ;merican 0il Fhemists Society, -2, 5@:5++.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB +/ 7uang, a. & Ka))a, ?. (%&55). Simultaneous analysis of serotonin, melatonin, piceid and resveratrol in fruits using liquid chromatography tandem mass spectrometry. Nournal of Fhromatography ;, 121/, @L:&@L::.

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Ceb of ScienceD Times FitedB + 7urtado!6ernande), >., ?ome)!$omero, K., Farrasco!Pancorbo, ;. & 6ernande)!?utierre), ;. (%&5&). ;pplication and potential of capillary electroseparation methods to determine antioxidant phenolic compounds from plant food material. Nournal of Pharmaceutical and .iomedical ;nalysis, 0(, 55@&55/&.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB 5+ Iacopini, P., .aldi, K., Storchi, P. & Sebastiani, 4. (%&&L). Fatechin, epicatechin, quercetin, rutin and resveratrol in red grapeB Fontent, in vitro antioxidant activity and interactions. Nournal of 6ood Fomposition and ;nalysis, 21, 'L:':L.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB +3 Ignat, I., -olf, I. & Popa, -.I. (%&55). ; critical review of methods for characterisation of polyphenolic compounds in fruits and vegetables. 6ood Fhemistry, 122, 5L%55L@'.

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Fross$ef, F;S, Ceb of ScienceD Times FitedB %5 Ikawa, K., Schaper, T.A., Aollard, F.;. & Sasner, N.N. (%&&@). ,tili)ation of 6olin!Fiocalteu phenol reagent for the detection of certain nitrogen compounds. Nournal of ;gricultural and 6ood Fhemistry, 01, 5L555L5'.

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Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB %+ Itoh, T., (inomiya, K., 9asuda, K. et al. (%&&:). Inhibitory effects of flavonoids isolated from 6ragaria ananassa Auch on Ig>!mediated degranulation in rat basophilic leukemia $.4!%7@. .ioorganic * Kedicinal Fhemistry, 1-, '@3+'@3:.

5. %. @. +. ::.

Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB ' Nakobek, 4., ceruga, K., ceruga, .., (ovak, I. & KedvidoviP!2osanoviP, K. (%&&:). Phenolic compound composition and antioxidant activity of fruits of $ubus and Prunus species from Froatia. International Nournal of 6ood Science * Technology, .., L/&L/L. Airect 4inkB

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;bstract

%. @. +. '.

6ull ;rticle "7TK4# PA6"L552# $eferences Ceb of ScienceD Times FitedB 5+

5&&. 2ahkonen, K.P., 7einamaki, N., 0llilainen, -. & 7einonen, K. (%&&@). .erry anthocyaninsB isolation, identification and antioxidant activities. Nournal of the Science of 6ood and ;griculture, /(, 5+&@5+55. Airect 4inkB

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;bstract 6ull ;rticle "7TK4# PA6"5+52# $eferences Ceb of ScienceD Times FitedB :@

5&5. 2ahle, 2., 2raus, K., Scheppach, C., ;ckermann, K., $idder, 6. & $ichling, >. (%&&/). Studies on apple and blueberry fruit constituentsB do the polyphenols reach the colon after ingestion` Kolecular (utrition * 6ood $esearch, 03, +5L+%@. Airect 4inkB

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;bstract PA6"@&'2# $eferences Ceb of ScienceD Times FitedB +L

5&%. 2alili, 2.K. & de -illiers, ;. (%&55). $ecent developments in the 7P4F separation of phenolic compounds. Nournal of Separation Science, (., L'+L3/. Airect 4inkB

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;bstract 6ull ;rticle "7TK4# PA6"@:&2# $eferences Ceb of ScienceD Times FitedB 3

5&@. 2ang, N., aie, F., 4i, T. et al. (%&55). 6lavonoids from acai ">uterpe oleracea Kart.# pulp and their antioxidant and anti!inflammatory activities. 6ood Fhemistry, 12/, 5'%5'3. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 3

5&+. 2asper, N.F. & 6riess, C. (%&55). The free)ing step in lyophili)ationB physico!chemical fundamentals, free)ing methods and consequences on process performance and quality attributes of biopharmaceuticals. >uropean Nournal of Pharmaceutics and .iopharmaceutics, -/, %+L%/@. 5. %. Fross$ef, F;S,

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5&'. 2aur, F. & 2apoor, 7.F. (%&&5). ;ntioxidants in fruits and vegetables G the millennium1s health. International Nournal of 6ood Science and Technology, (2, 3&@3%'. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB @/5

5&/. 2elebek, 7. & Selli, S. (%&55a). Aetermination of volatile, phenolic, organic acid and sugar components in a Turkish cv. Aortyol "Fitrus sinensis 4. 0sbeck# orange Ouice. Nournal of the Science of 6ood and ;griculture, 11, 5L''5L/%. Airect 4inkB

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;bstract 6ull ;rticle "7TK4# PA6"55/2# $eferences Ceb of ScienceD Times FitedB @

5&3. 2elebek, 7. & Selli, S. (%&55b). >valuation of chemical constituents and antioxidant activity of sweet cherry "Prunus avium 4.# cultivars.International Nournal of 6ood Science * Technology, .2, %'@&%'@3. Airect 4inkB

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;bstract 6ull ;rticle "7TK4# PA6"3&/2# $eferences Ceb of ScienceD

5&L. 2evers, F., 6alkowski, K., Tabart, N., Aefraigne, N.0., Aommes, N. & Pincemail, N. (%&&3). >volution of antioxidant capacity during storage of selected fruits and vegetables. Nournal of ;gricultural and 6ood Fhemistry, 00, L':/L/&@. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB '/

5&:. 2im, A.!0. & 4ee, F.9. (%&&5). >xtraction and isolation of polyphenolics. C'rrent *rotocols in &ood 2nalytical Chemistry. 0o)o"en, N<, ,12# <ohn .iley & 1ons, Inc. 55&. 2ing, $.>., .omser, N.;. & Kin, A... (%&&/). .ioactivity of resveratrol. Fomprehensive $eviews in 6ood Science and 6ood Safety, 0,/'3&. Airect 4inkB

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;bstract 6ull ;rticle "7TK4# PA6"5@L2#

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555. 2oli, $., >rlund, I., Nula, ;., Karniemi, N., Kattila, P. & ;lfthan, ?. (%&5&). .ioavailability of various polyphenols from a diet containing moderate amounts of berries. Nournal of ;gricultural and 6ood Fhemistry, 0/, @:%3@:@%. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 3

55%. 2otikova, T., 4achman, N., 7eOtmankova, ;. & 7eOtmankova, 2. (%&55). Aetermination of antioxidant activity and antioxidant content in tomato varieties and evaluation of mutual interactions between antioxidants. 4CT G 6ood Science and Technology, ..,53&@535&. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 3

55@. 2roon, P.;., Flifford, K.(., Fro)ier, ;. et al. (%&&+). 7ow should we assess the effects of exposure to dietary polyphenols in vitro` The ;merican Nournal of Flinical (utrition, /3, 5'%5. 5. %. @. PubKed, F;S, Ceb of ScienceD Times FitedB 5LL

55+. 2ubola, N., Siriamornpun, S. & Keeso, (. (%&55). Phytochemicals, vitamin F and sugar content of Thai wild fruits. 6ood Fhemistry,122, :3%:L5. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 5

55'. 2urosumi, ;., Sasaki, F., 2umada, 2., 2obayashi, 6., Ktui, ?. & (akamura, 9. (%&&3). (ovel extraction method of antioxidant compounds from Sasa palmata ".ean# (akai using steam explosion. Process .iochemistry, .2, 5++:5+'@. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB :

55/. 4ako, N., Trenerry, -.F., Cahlqvist, K., Cattanapenpaiboon, (., Sotheeswaran, S. & Premier, $. (%&&3). Phytochemical flavonols, carotenoids and the antioxidant properties of a wide selection of 6iOian fruit, vegetables and other readily available foods. 6ood Fhemistry, 131, 53%353+5. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB /@

553. 4ambert, S.?., ;senstorfer, $.>., Cilliamson, (.K., Iland, P.?. & Nones, ?.P. (%&55). Fopigmentation between malvidin!@!glucoside and some wine constituents and its importance to colour expression in red wine. 6ood Fhemistry, 120, 5&/55'. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB '

55L. 4ampila, P., van 4ieshout, K., ?remmen, .. & 4ahteenmaki, 4. (%&&:). Fonsumer attitudes towards enhanced flavonoid content in fruit. 6ood $esearch International, .2, 5%%5%:. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 5+

55:. 4in, N.9. & Tang, F.9. (%&&3). Aetermination of total phenolic and flavonoid contents in selected fruits and vegetables, as well as their stimulatory effects on mouse splenocyte proliferation. 6ood Fhemistry, 131, 5+&5+3. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB L@

5%&. 4iu, S., Kanson, N.>., 4ee, I.K. et al. (%&&&). 6ruit and vegetable intake and risk of cardiovascular diseaseB the Comen1s 7ealth Study.;merican Nournal of Flinical (utrition, -2, :%%:%L. 5. %. @. PubKed, F;S, Ceb of ScienceD Times FitedB @+/

1#1. 4PI (%&55). 4inus Pauling Institute G micronutrient research for optimum health. 2vaila)le
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5%@. 4uthria, A.4. (%&&L). Influence of experimental conditions on the extraction of phenolic compounds from parsley "Petroselinum crispum# flakes using a pressuri)ed liquid extractor. 6ood Fhemistry, 13-, 3+' 3'%. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB %5

5%+. 4uthria, A.4. & Pastor!Forrales, K.;. (%&&/). Phenolic acids content of fifteen dry edible bean "Phaseolus vulgaris 4.# varieties.Nournal of 6ood Fomposition and ;nalysis, 11, %&'%55. 5. Fross$ef,

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5%'. Ka, 9.!U., Fhen, N.!F., 4iu, A.!7. & 9e, a.!U. (%&&:). Simultaneous extraction of phenolic compounds of citrus peel extractsB effect of ultrasound. ,ltrasonics Sonochemistry, 12, '3/%. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB %5

5%/. Kamede, K.>.0., Kiranda, K.P.S., $it)inger, $., ?odoy, $.F... & -elo)o, >.S. (%&&:). Physico! chemical and sensorial evaluation of new varieties of acerola. .ritish 6ood Nournal, 111, @L3@:'. 5. Ceb of ScienceD

5%3. Kanach, F., Korand, F., Frespy, -. et al. (5::L). Uuercetin is recovered in human plasma as conOugated derivatives which retain antioxidant properties. 6ebs 4etters, .22, @@5@@/. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB @'L

5%L. Kanach, F., Scalbert, ;., Korand, F., $emesy, F. & Nimene), 4. (%&&+). PolyphenolsB food sources and bioavailability. ;merican Nournal of Flinical (utrition, -1, 3%33+3. 5. %. @. PubKed, F;S, Ceb of ScienceD Times FitedB 55@&

5%:. Kanach, F., Cilliamson, ?., Korand, F., Scalbert, ;. & $emesy, F. (%&&'). .ioavailability and bioefficacy of polyphenols in humans. I. $eview of :3 bioavailability studies. ;merican Nournal of Flinical (utrition, /1, %@&S%+%S. 5. %. @. PubKed, F;S, Ceb of ScienceD Times FitedB '%@

5@&. Karais, N.P.N., Aeavours, .., Aixon, $.;. & 6erreira, A. (%&&/). The stereochemistry of flavonoids. In# ?he 1cience of &lavonoids (edited )y >. ?rotewold). *p. 5+/. Ne !or", N!# 1pringer. 5. Fross$ef

5@5. Karinova, A., $ibarova, 6. & ;tanassov, K. (%&&'). Total phenolics and total flavonoids in bulgarian fruits and vegetables. Nournal of the ,niversity of Fhemical Technology and Ketallurgy, .3, %''%/&. 5. F;S

5@%. Karques, 4.?., 6erreira, K.F. & 6reire, N.T. (%&&3). 6ree)e!drying of acerola "Kalpighia glabra 4.#. Fhemical >ngineering and Processing, .2, +'5+'3. 5. %. Fross$ef, F;S,

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Ceb of ScienceD Times FitedB 53

5@@. Karques, 4.?., Prado, K.K. & 6reire, N.T. (%&&:). $ehydration characteristics of free)e!dried tropical fruits. 4CT G 6ood Science and Technology, .2, 5%@%5%@3. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB :

5@+. Ka))a, ?. (5::'). ;nthocyanins in grapes and grape products. Fritical $eviews in 6ood Science and (utrition, (0, @+5@35. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB %5:

5@'. Keagher, 4.P. & .eecher, ?.$. (%&&&). ;ssessment of data on the lignan content of foods. Nournal of 6ood Fomposition and ;nalysis,1(, :@':+3. 5. %. Fross$ef, F;S

5@/. Kedina, ;.4., 7aas, 4.I.$., Fhaves, 6.F. et al. (%&55). ;raca "Psidium cattleianum Sabine# fruit extracts with antioxidant and antimicrobial activities and antiproliferative effect on human cancer cells. 6ood Fhemistry, 12/, :5/:%%. 5. %. @. Fross$ef, F;S, Ceb of ScienceD

5@3. Kedoua, ?.(. & 0ldewage!Theron, C.7. (%&55). .ioactive compounds and antioxidant properties of selected fruits and vegetables available in the vaal region, South ;frica. Nournal of 6ood .iochemistry, (0, 5+%+5+@@. Airect 4inkB

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5@L. Kensor, 4.4., Kene)es, 6.S., 4eitao, ?.?. et al. (%&&5). Screening of .ra)ilian plant extracts for antioxidant activity by the use of APP7 free radical method. Phytotherapy $esearch, 10, 5%35@&. Airect 4inkB

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;bstract PA6"L32# $eferences Ceb of ScienceD Times FitedB %&@

5@:. Kerken, 7.K. & .eecher, ?.$. (%&&&). Keasurement of food flavonoids by high!performance liquid chromatographyB a review. Nournal of ;gricultural and 6ood Fhemistry, ./, '33'::. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB %+&

5+&. Kessaoud, F. & .oussaid, K. (%&55). Kyrtus communis berry color morphsB a comparative analysis of essential oils, fatty acids, phenolic compounds, and antioxidant activities. Fhemistry * .iodiversity, /, @&&@5&. Airect 4inkB

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;bstract PA6"@L'2# $eferences Ceb of ScienceD Times FitedB %

5+5. Kiean, 2.7. & Kohamed, S. (%&&5). 6lavonoid "myricetin, quercetin, kaempferol, luteolin, and apigenin# content of edible tropical plants. Nournal of ;gricultural and 6ood Fhemistry, .1, @5&/@55%. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB 5LL

5+%. Kishra, 2., 0Oha, 7. & Fhaudhury, (.2. (%&5%). >stimation of antiradical properties of antioxidants using APP7 assayB a critical review and results. 6ood Fhemistry, 1(3, 5&@/5&+@. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB %

5+@. Kolyneux, P. (%&&+). The use of the stable free radical diphenylpicrylhydra)yl "APP7# for estimating antioxidant activity.Songklanakarin Nournal of Science and Technology, 22, %55%5:. 5. F;S

5++. Koreno!6ranco, .., ?arcia!?on)ale), ;., Kontero!.ravo, ;.K. et al. (%&55). Aietary alkylresorcinols and lignans in the Spanish dietB development of the alignia database. Nournal of ;gricultural and 6ood Fhemistry, 01, :L%3:L@+. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 5

5+'. Kouly, P.P., ;r)ouyan, F.$., ?aydou, >.K. & >stienne, N.K. (5::+). Aifferentiation of citrus Ouices by factorial discriminant!analysis using liquid!chromatography of flavanone glycosides. Nournal of ;gricultural and 6ood Fhemistry, .2, 3&3:. 5. Fross$ef,

%. @.

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5+/. Kueller, K., 7obiger, S. & Nungbauer, ;. (%&5&). ;nti!inflammatory activity of extracts from fruits, herbs and spices. 6ood Fhemistry,122, :L3::/. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 5'

5+3. Kuno)!>spada, ;.F., Cood, 2.-., .ordelon, .. & Catkins, ..;. (%&&+). ;nthocyanin quantification and radical scavenging capacity of Foncord, (orton, and Karechal 6och grapes and wines. Nournal of ;gricultural and 6ood Fhemistry, 02, /33:/3L/. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB +&

5+L. (ac)k, K. & Shahidi, 6. (%&&+). >xtraction and analysis of phenolics in food. Nournal of Fhromatography ;, 130., :'555. 5. %. @. PubKed, F;S, Ceb of ScienceD Times FitedB %%/

5+:. (eto, F.F., ;moroso, N.C. & 4iberty, ;.K. (%&&L). ;nticancer activities of cranberry phytochemicalsB an update. Kolecular (utrition * 6ood $esearch, 02, S5LS%3. 5. Ceb of ScienceD Times FitedB @&

5'&. (oipa, T., SriOaranai, S., Tuntulani, T. & (geontae, C. (%&55). (ew approach for evaluation of the antioxidant capacity based on scavenging APP7 free radical in micelle systems. 6ood $esearch International, .., 3:LL&/. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB '

5'5. 0bdn, N.K., AZa)!?arcZa, K.F. & Fastellar, K.$. (%&55). $ed fruit Ouice quality and authenticity control by 7P4F. Nournal of 6ood Fomposition and ;nalysis, 2., 3/&335. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB %

5'%. 0breque!Slier, >., Pena!(eira, ;., 4ope)!Solis, $., Tamora!Karin, 6., $icardo!da Silva, N.K. & 4aureano, 0. (%&5&). Fomparative study of the phenolic composition of seeds and skins from carmenere and cabernet sauvignon grape varieties "-itis vinifera 4.# during ripening. Nournal of ;gricultural and 6ood Fhemistry, 0/, @':5@'::. 5. Fross$ef,

%. @.

F;S, Ceb of ScienceD Times FitedB 5'

5'@. 0rak, 7.7. (%&&3). Total antioxidant activities, phenolics, anthocyanins, polyphenoloxidase activities of selected red grape cultivars and their correlations. Scientia 7orticulturae, 111, %@'%+5. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB @'

5'+. 0s)mianski, N., CoOdylo, ;. & 2olniak, N. (%&&:). >ffect of 4!ascorbic acid, sugar, pectin and free)e!thaw treatment on polyphenol content of fro)en strawberries. 4CT G 6ood Science and Technology, .2, 'L5 'L/. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB /

5''. 0u, ..a., 7ampsch!Coodill, K. & Prior, $.4. (%&&5). Aevelopment and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. Nournal of ;gricultural and 6ood Fhemistry, .1, +/5:+/%/. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB '3@

5'/. Palafox!Farlos, 7., ;yala!Tavala, N.6. & ?on)ble)!;guilar, ?.;. (%&55). The role of dietary fiber in the bioaccessibility and bioavailability of fruit and vegetable antioxidants. Nournal of 6ood Science, -2, $/ $5'. Airect 4inkB

5. %. @. +. '.

;bstract 6ull ;rticle "7TK4# PA6"%::2# $eferences Ceb of ScienceD Times FitedB @

5'3. Paniwnyk, 4., .eaufoy, >., 4orimer, N.P. & Kason, T.N. (%&&5). The extraction of rutin from flower buds of Sophora Oaponica. ,ltrasonics Sonochemistry, /, %::@&5. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB /'

5'L. Parada, N. & ;guilera, N.K. (%&&3). 6ood microstructure affects the bioavailability of several nutrients. Nournal of 6ood Science, -2,$%5$@%. Airect 4inkB

5. %. @. +. '.

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5':. Pere)!Nimene), N., Serrano, N., Tabernero, K. et al. (%&&:). .ioavailability of phenolic antioxidants associated with dietary fiberB plasma antioxidant capacity after acute and long!term intake in humans. Plant 6oods for 7uman (utrition, 2., 5&%5&3. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB %%

5/&. Pla)a, 4., Frespo, I., de Pascual!Teresa, S. et al. (%&55). Impact of minimal processing on orange bioactive compounds during refrigerated storage. 6ood Fhemistry, 12., /+//'5. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB @

5/5. Plumb, ?.C., ?arcia!Fonesa, K.T., 2roon, P.;., $hodes, K., $idley, S. & Cilliamson, ?. (5:::). Ketabolism of chlorogenic acid by human plasma, liver, intestine and gut microflora. Nournal of the Science of 6ood and ;griculture, -1, @:&@:%. Airect 4inkB

5. %. @. +.

;bstract PA6"3:2# $eferences Ceb of ScienceD Times FitedB 3L

5/%. Poovarodom, S., 7aruenkit, $., -earasilp, S. et al. (%&5&). Fomparative characterisation of durian, mango and avocado. International Nournal of 6ood Science and Technology, .0, :%5:%:. 5. %. F;S, Ceb of ScienceD Times FitedB '

5/@. Prasad, 2.(., 9ang, .., Thao, K., Sun, N., Cei, a. & Niang, 9. (%&5&). >ffects of high pressure or ultrasonic treatment on extraction yield and antioxidant activity of pericarp tissues of longan fruit. Nournal of 6ood .iochemistry, (., L@LL''. 5. %. F;S, Ceb of ScienceD Times FitedB L

5/+. Prasad, 2.(., 7assan, 6.;., 9ang, .. et al. (%&55). $esponse surface optimisation for the extraction of phenolic compounds and antioxidant capacities of underutilised Kangifera paOang 2osterm. peels. 6ood Fhemistry, 12/, 55%555%3. 5. %. Fross$ef, F;S,

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Ceb of ScienceD Times FitedB @

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5//. Prior, $.4., Cu, a.4. & Schaich, 2. (%&&'). Standardi)ed methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. Nournal of ;gricultural and 6ood Fhemistry, 0(, +%:&+@&%. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB 35L

5/3. Uuitain, ;.T., 0ro, 2., 2atoh, S. & Koriyoshi, T. (%&&/). $ecovery of oil components of okara by ethanol! modified supercritical carbon dioxide extraction. .ioresource Technology, 1-, 5'&:5'5+. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB 5%

5/L. $amful, A., ;umOaud, .., (eergheen, -.S. et al. (%&55). Polyphenolic content and antioxidant activity of >ugenia pollicina leaf extract in vitro and in model emulsion systems. 6ood $esearch International, .., 55:&55:/. 5. %. @. Fross$ef, F;S, Ceb of ScienceD

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53&. $ibeiro, I.;. & $ibeiro, K.7.4. (%&&L). (aringin and naringenin determination and control in grapefruit Ouice by a validated 7P4F method. 6ood Fontrol, 11, +@%+@L. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB %%

535. $inaldo, A., Kbeguie!;!Kbeguie, A. & 6ils!4ycaon, .. (%&5&). ;dvances on polyphenols and their metabolism in sub!tropical and tropical fruits. Trends in 6ood Science * Technology, 21, '::/&/. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 5

53%. $ispail, (., Korris, P. & Cebb, 2. (%&&'). Phenolic compoundsB extraction and analysis. In# 7ot's <aponic's 0and)oo" (edited )y ;. Kbrque)). *p. @+:@'+. /erlin# 1pringer. 5. Fross$ef

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53'. $ockenbach, I.I., ?on)aga, 4.-., $i)elio, -.K., ?oncalves, ;., ?enovese, K.I. & 6ett, $. (%&55). Phenolic compounds and antioxidant activity of seed and skin extracts of red grape "-itis vinifera and -itis labrusca# pomace from .ra)ilian winemaking. 6ood $esearch International, .., L:3 :&5. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB @

53/. $odrigo, $., Kiranda, ;. & -ergara, 4. (%&55). Kodulation of endogenous antioxidant system by wine polyphenols in human disease.Flinica Fhimica ;cta, .12, +5&+%+. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 53

533. $odrigues, S. & Pinto, ?.;.S. (%&&3). ,ltrasound extraction of phenolic compounds from coconut "Focos nucifera# shell powder.Nournal of 6ood >ngineering, /3, L/:L3%. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB @5

53L. $osa, 4.;., ;lvare)!Parrilla, >. & ?on)ble)!;guilar, ?.;. (%&5&). &r'it and (egeta)les *hytochemicals. 2mes, I2, ,12# .iley-/lac" ell.

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5L&. $ussell, C.$., 4abat, ;., Scobbie, 4., Auncan, ?.N. & Authie, ?.?. (%&&:a). Phenolic acid content of fruits commonly consumed and locally produced in Scotland. 6ood Fhemistry, 110, 5&&5&+. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 5%

5L5. $ussell, C.$., Scobbie, 4., 4abat, ;. & Authie, ?.?. (%&&:b). Selective bio!availability of phenolic acids from Scottish strawberries.Kolecular (utrition * 6ood $esearch, 0(, SL'S:5. Airect 4inkB

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5L@. Saiko, P., S)akmary, ;., Naeger, C. & S)ekeres, T. (%&&L). $esveratrol and its analogsB defense against cancer, coronary disease and neurodegenerative maladies or Oust a fad` Kutation $esearch!$eviews in Kutation $esearch, 20/, /L:+. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB 553

5L+. Saura!Falixto, 6., Serrano, N. & ?oni, I. (%&&3). Intake and bioaccessibility of total polyphenols in a whole diet. 6ood Fhemistry, 131,+:%'&5. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB :@

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5:&. Shi, N. & 4e Kaguer, K. (%&&&). 4ycopene in tomatoesB chemical and physical properties affected by food processing. Fritical $eviews in 6ood Science and (utrition, .3, 5+%. 5. %. @. +. Fross$ef, PubKed, F;S, Ceb of ScienceD Times FitedB 5:&

5:5. Silva, ;.$., Pinheiro, ;.K., Sou)a, F.S. et al. (%&&L). The flavonoid rutin induces astrocyte and microglia activation and regulates T(6!alpha and (0 release in primary glial cell cultures. Fell .iology and Toxicology, 2., 3'L/. 5. Fross$ef,

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%+3. Thang, K.a., Auan, F.U., Tang, 9.9., 7uang, T.C. & 4iu, ?.N. (%&55). The flavonoid composition of flavedo and Ouice from the pummelo cultivar "Fitrus grandis "4.# 0sbeck# and the grapefruit cultivar "Fitrus paradisi# from Fhina. 6ood Fhemistry, 121, 5'@&5'@/. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 5

%+L. Thao, N., 4v, ?.!P., Fhen, 9.!C. & 4i, S.!P. (%&55). ;dvanced development in analysis of phytochemicals from medicine and food dual purposes plants used in Fhina. Nournal of Fhromatography ;, 121/, 3+'@ 3+3'. 5. %. @. Fross$ef, F;S, Ceb of ScienceD Times FitedB 5

%+:. Theng, 7.!T., 2im, 9.!I. & Fhung, S.!2. (%&5%). ; profile of physicochemical and antioxidant changes during fruit growth for the utilisation of unripe apples. 6ood Fhemistry, 1(1, 5&/55&. 5. %. @. Fross$ef, F;S, Ceb of ScienceD