Referat Compusi Biologic Activi

8/13/2019 Referat Compusi Biologic Activi

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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

bioaccessibilitybioavailability 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 freeradical 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 freeradicals 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 vitroand in vivotechniques are addressed. 6inally, the

health benefits and the bioavailabilitybioaccessibility of the phenolic compounds in the human body are

discussed.

Research on phenolic compounds in fruits
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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:::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 derive d from the

Ceb of ScienceDprepared by Thomson $eutersD, Inc. "ThomsonD#, Philadelphia, P;, S;B EFopyright Thomson

$eutersD%&5%. ;ll rights reserved.

Classification and chemical structure of phenolic compounds
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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, %&&/


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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

";tanackoviet 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., %&&Lnvironment and $ural and Karine

;ffairs, the average intake of lignans from fruits and vegetables is estimated to be %@@./ g 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

inTable 5 .

Table 1. Main dietary source of polyphenols in fruits
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Etraction 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 "hao et al., %&55#. To achieve maximum

extraction, it is recommended that several different parameters are tested, such as the solvent, agitation,

extraction time, solutesolvent ratio, temperature, efficiency of mass transfer and particle si)e, for example

"4uthria, %&&L


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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 F 5LSep!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 byFasas 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 Wmethanol7Fl "&.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 spectrophotometrictechni"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 byspectrophotometric measurements
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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

Fruit

materialSample Sol$ent Total phenolics Total fla$onoids Total anthocyanins References

5. amg ?;> 5&& gM5of fresh weight.

%. bmg 5&& gM5of fresh weight "expressed as cyanidin @!glucoside or malvidin!@!glucoside#.

@.cmg F;> 5&& gM5of fresh weight.

+. dmg of U> 5&& gM5of fresh weight.

'. emg ?;> lM5of fresh weigh.

6. fmg F> 5&& gM5of fresh weight.

3. ?;>, gallic acid equivalent< F;>, chlorogenic acid equivalent< U>, quercetin equivalent< F>, catechin equivalent.

;YaZ 6resh Kethanolacetone +'+.&&a 555.&&b $ufino et al. "%&5

;cerola 6resh Kethanolacetone 5&/@.&&a G 5L.:&b $ufino et al. "%&5

anana 6resh ;cetonewateracetic acid +3'.&&c &.3&d &.&&b 2evers et al. "%&&3#

lackberry 6resh Phosphate buffer %%/.&&a G 5'@.@&b Cang * 4in "%&&

Fambuci 6resh >thanol @+5+.&&e @&.5/d 5:.++b 7aminiuk et al."%&55#

6ig 6resh Kethanol7Fl +/@.&&a +'./&f %3.@&b Solomon et al."%&&/#

?rape 6resh Kethanol7Fl %@+L.&&e G ::.&Lb 0rak "%&&3#

2iwifruit 6resh ;cetonewateracetic acid 55%.&&c &.+&d &.&&b 2evers et al. "%&&3#

Kulberry4yophilised

powderCater 5'5'.:&a %'&.5&d G 4in * Tang "%&&3#

0range 6resh ;cetonewateracetic acid %+@.&&c /.5&d &.&&b 2evers et al. "%&&3#

Plum 6resh ;cetonewateracetic acid @55.&&c @.&&d 5&%.&&b 2evers et al. "%&&3#

$aspberry 6resh Phosphate buffer %/3.&&a G 5:3.%&b Cang * 4in "%&&

Strawberry4yophilised

powderCater @/@.3&a 5+./&d G 4in * Tang "%&&3#

vaia 6resh >thanol @3@.+&e 'L.3%d +.33b 7aminiuk et al."%&55#
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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:/' 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., %&&+


10/56

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%


11/56

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 * 4orutto,%&&/#, 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!KSKS"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!KSKS "ultra!

7P4FGtandem mass spectrometry# and 7P4F!>SI!T06KS "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

inTable @ .
http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#f3http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#f3http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#f3http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b205http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b205http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b205http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b108http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b108http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b48http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#t3http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#t3http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#t3http://onlinelibrary.wiley.com/store/10.1111/j.1365-2621.2012.03067.x/asset/image_n/IJFS_3067_f3.gif?v=1&t=hmp4xo78&s=f1df8449e146a3ecbafcb66fb2619d10ea0d10c4http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#f3http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b205http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b205http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b108http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b108http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b48http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#t3


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Fruit

material

Mobile phase (gradient)/flow

rate (ml min1)

Column type and temperature

( C)

Wavelength ()

nm

Ma!or "ompounds

identified#eferen"es

Raspberry

A (0.1% phosphoric acid in

water), B (methanol), 0.8

Varian

mnisphere!"18(#$0 &.6 mm

len'th, $ m)#0

#80, *60 and

$#0

+lla'ic acid and ()-

catechin, ()-epicatechin,

/ercetin and cyanidin

a2obe2et al. (#003)

4weet

cherry

A ($% 5ormic acid in water), B

(acetonitrilesolent A 607&0),

1.0

Bec2man ltrasphere!94

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

#80, *16, *6$

and $#0

:eochloro'enic acid, ()-

epicatechin, rtin and

cyanidin'

;elebe2 < 4elli (#011b)

=rape

pomace

A (#% acetic acid in water), B

(methanol), 0.8

A'ilent +clipse

>9B!"18(#$0 &.6 mm len'th,

$ m)*0

#?8"hloro'enic acid, 'allic

acid and ()-catechin4a'dic et al.(#011)

@an'oA (0.$% acetic acid in water), B

(methanol), 0.8

@erc2

ichrospher!"18(#$0 &.0 mm

len'th, $ m)&0

#$&, #80, *#0

and *6$

=allic acid,p-comaric

acid, ella'ic, man'i5erin

and rtin

assanet al. (#011)

;iwi5rit

waste

A (0.1% 5ormic acid in

acetonitrile), (B)

acetonitrilewater5ormic acid

($73#7*), 1,$

ChenomeneD!"18(#$0 &.6 mm

len'th, & m)&$

#80, *#0 and

*?0

"a55eic acid,p-

hydroDybenEoic acid and

syrin'ic acid

4n-Faterhoseet al. (#00

3)

4trawberryA (&.$% 5ormic acid in water),

B (acetonitrile), 1.0

ChenomeD!"18(#$0 &.6 mm len'th,

& m)*0

#80,*#0, *60

and $#0

Croanthocyanidins, ()-

catechin,p-comaric acid

and pelar'onidin

sEmians2iet al. (#003)

Apple

Gice

A (acetic acid in # m@sodim

acetate, 5inal p #.$$), B

(acetonitrile), 1.0

A'ilent HorbaD!4B

"18"18(1$0 &.6 mm len'th,

$ m)*?

#80, *#0 and

*60

"hloro'enic acid, ca55eic

acid, cinnamic acidIorres et al.(#011)

Bayberry

Gice

A (0.1% 5ormic acid in water),

B (80% acetonitrile in water),

1.0

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

$ m)*0*60 and $#0

Jercetin, 2aemp5erol

and cyanidinKan' et al.(#003)

=aaA (acetic acid in water p

#.?&), B (acetonitrile), 0.8

ChenomeD na!"18(#$0 &.6 mm

len'th, $ m)*8

#80, *#0 and

*?0

Rtin, lteolin, api'enin

and 2aemp5erol;bolaet al. (#011)

=rape s2in

A (#% acetic acid in water), B

(wateracetonitrileacetic acid,

?87#07#), 1.0

Faters :oa Cac2!"18(#$0 &.6 mm

len'th, $ m)#0#10L*60

Jercetin, 2aemp5erol

and myricetinbre/e-4lier et al.(#010)

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

is
http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b98http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b98http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b98http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b98http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b98http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b98http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b98http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b106http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b181http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b181http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b181http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b181http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b181http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b181http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b181http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b85http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b85http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b85http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b85http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b85http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b85http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b85http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b206http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b206http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b206http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b206http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b206http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b206http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b206http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b56http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b56http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b56http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b56http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b56http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b56http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b56http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b113http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b113http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b113http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b113http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b113http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b113http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b113http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b151http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b151http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b151http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b151http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b151http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b151http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b151http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b98http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b106http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b181http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b85http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b197http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b153http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b206http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b56http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b113http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2621.2012.03067.x/full#b151


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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.

)ntioidant 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 APP7Hfree 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 evaluateantioxidant 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 APP7 Hby an antioxidant "reduction of APP7 Hto 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., %&&'


14/56

6urthermore, owing to its biological relevance to the in vivoantioxidant 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,

%,%!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::@


15/56

%&5%#. In vitrotests have shown that phenolic compounds inhibit cancer cell proliferation, protect neurons,

improve insulin secretion, reduce vascularisation and stimulate vasodilation "6erguson et al., %&&+


16/56

; 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 compoundthat 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


17/56

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, %&&&


18/56

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. FonOugationdeconOugation

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


19/56

investigations. The absorption mechanisms of phenolic compounds are still not well established. 6urther

investigations are necessary to better understand the bioaccessibilitybioavailability 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.

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Referat Compusi Biologic Activi