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ALMA MATER STUDIORUM - UNIVERSITÀ DI BOLOGNA C.SO D’AUGUSTO 237 - 47921 RIMINI - ITALIA - TEL. +39 0541 434601 - FAX +39 0541 434607 MAQUI Composition of Maqui berries Maqui berries (Aristotelia chilensis) possess a high percentage of pulp (88% dry weight) rich in minerals (K, Ca, Fe and Na). The concentration of micro and macronutrients in the fruit not only affects the organoleptic characteristics, but also the nutritional and health benefits that consumers may draw (Damascos et al., 2008). The phytochemical analysis of the composition of the fruits of A. chilensis have revealed the presence of a large number of polyphenols among which are particularly represented anthocyanins Gironés- Vilaplana et al., (2012). Other studies have evaluated the quantitative composition of the different anthocyanins present in the extracts dried fruits showing that concentrations of anthocyanins, expressed as delphinidin 3-O-glucoside equivalents, reveal a predominance of derivatives of delphinidin (~ 73%) compared to derivatives of cyanidin (~ 37%), while the most present anthocyanin is delphinidin-3-O-sambubioside-5-O-glucoside (Figure 1). The relatively high content of anthocyanins and the presence of derivatives polyglycosilated, polar and water-soluble, making the berries of Maqui an interesting source of polyphenols to pharmacological use (Escribano-Bailon et al., 2006; Cespedes et al., 2010). R’ R3 R5 Name Content mg/100g OH Xyl-glu Glu Delfinidina-3-sambubioside-5-glucoside 101.05 OH Glu Glu Delfinidina-3,5-diglucoside 49.80 H Xyl-glu Glu Cianidina-3-sambubioside-5-glucoside 20.73 H Glu Glu Cianidina-3,5-diglucoside 18.71 OH Xyl-glu H Delfinidina-3-sambubioside 30.51 OH Glu H Delfinidina-3-glucoside 32.53 H Xyl-glu H Cianidina-3-sambubioside 17.37 H Glu H Cianidina-3-glucoside 17.20 Totale 287.9 Figure 1: chemical structure of anthocyanins. The content is expressed in mg-equivalent of delphinidin- 3-glucoside in dried fruit (Cespedes et al., 2010).
Transcript

ALMA MATER STUDIORUM - UNIVERSITÀ DI BOLOGNA C.SO D’AUGUSTO 237 - 47921 RIMINI - ITALIA - TEL. +39 0541 434601 - FAX +39 0541 434607

MAQUI

Composition of Maqui berries Maqui berries (Aristotelia chilensis) possess a high percentage of pulp (88% dry weight) rich in

minerals (K, Ca, Fe and Na). The concentration of micro and macronutrients in the fruit not only

affects the organoleptic characteristics, but also the nutritional and health benefits that consumers may

draw (Damascos et al., 2008).

The phytochemical analysis of the composition of the fruits of A. chilensis have revealed the presence

of a large number of polyphenols among which are particularly represented anthocyanins Gironés-

Vilaplana et al., (2012). Other studies have evaluated the quantitative composition of the different

anthocyanins present in the extracts dried fruits showing that concentrations of anthocyanins,

expressed as delphinidin 3-O-glucoside equivalents, reveal a predominance of derivatives of

delphinidin (~ 73%) compared to derivatives of cyanidin (~ 37%), while the most present anthocyanin

is delphinidin-3-O-sambubioside-5-O-glucoside (Figure 1).

The relatively high content of anthocyanins and the presence of derivatives polyglycosilated, polar and

water-soluble, making the berries of Maqui an interesting source of polyphenols to pharmacological

use (Escribano-Bailon et al., 2006; Cespedes et al., 2010).

R’ R3 R5 Name Content

mg/100g

OH Xyl-glu Glu Delfinidina-3-sambubioside-5-glucoside 101.05

OH Glu Glu Delfinidina-3,5-diglucoside 49.80

H Xyl-glu Glu Cianidina-3-sambubioside-5-glucoside 20.73

H Glu Glu Cianidina-3,5-diglucoside 18.71

OH Xyl-glu H Delfinidina-3-sambubioside 30.51

OH Glu H Delfinidina-3-glucoside 32.53

H Xyl-glu H Cianidina-3-sambubioside 17.37

H Glu H Cianidina-3-glucoside 17.20

Totale 287.9

Figure 1: chemical structure of anthocyanins. The content is expressed in mg-equivalent of delphinidin-

3-glucoside in dried fruit (Cespedes et al., 2010).

ALMA MATER STUDIORUM - UNIVERSITÀ DI BOLOGNA C.SO D’AUGUSTO 237 - 47921 RIMINI - ITALIA - TEL. +39 0541 434601 - FAX +39 0541 434607

A recent study (Lila et al., 2012) has attempted to assess the bioavailability and distribution of

polyphenols in some berries, including those of A. chilensis.

The results obtained from the extract of anthocyanins berry Maqui indicate that the absorption in the

small intestine is highly dependent on the molecule in question.

Most anthocyanins bioaccessibility has a relatively low (0.75-4.28% assumption) with the exception

of the mixed sample consisting of cyanidin-3-sambubioside-5-glucoside and cyanidin-3,5-diglucoside

(17.84% of 'assumed). E 'has been hypothesized that the combination of cyanidin with two sugars

linked antocianinica create a structure more stable.

Biological action of extracts of Maqui

Action Antiosidante It is known how many polyphenols possess a strong antioxidant activity directly. The ability of

scavenging, owned by anthocyanins, can be explained by the ability to donate an electron to the

reactive species and is associated with the presence of a catechol group on the ring B. Thus, the more

the molecular structure is rich in hydroxyl groups, more will be effective in its ability to scavenge.

Considering the structure-activity relationships of anthocyanins, it is evident how the delfinidine,

which possess three OH groups on the ring B, are equipped with a higher antioxidant capacity.

The presence of functional groups, such as hydroxyl groups on the ring B, and in position 5 on ring A,

also contributes to the ability to chelate metals, such as Fe2 +, involved in oxidative reactions. It has

been demonstrated that the anthocyanin nasunina (delphinidin-3- (p-cumaroilrutinoside) -5-glucoside)

prevents the formation of free radicals, mainly thanks to the ability to chelate ferrous ions.

While the ability to scavanging free radical represents a major mode with which phenols antioxidants

may act in vivo, their activity is not limited to this mechanism of action.

Direct antioxidant action alongside specific anti-inflammatory capabilities, vasodilator,

antimicrobial and inhibiting platelet aggregation (Kang et al., 2011; Scholz et al., 2010).

Ateosclerosi

The oxidation of LDL, low density lipoprotein, is considered an initial event in the development of

atherosclerosis (Glass et al., 2001). For this reason we are trying to find a correlation between the beneficial

effects obtained by the consumption of fruit and vegetables in the case of cardiovascular disease with the ability

of the polyphenols contained therein to inhibit the oxidation of LDL. The oxidized LDL induce oxidative stress

and alter the expression of genes in endothelial cells by acting on all the major events leading to the

development of plaques at the level of the arterial walls. It is evident that polyphenols can both prevent the

oxidation of LDL is directly protect endothelial cells from other sources of oxidative stress (Youdim et al.,

2000). Extracts of Maqui may assume both of these actions, it has first suggested the use for antiatherogenic

properties.

Ischemia / reperfusion The ischemia-reperfusion injury occurs when the coronary blood flow is restored after a period of

myocardial ischemia and involves damage to cardiac cells and subsequent necrosis. In this context, the

protective action of degliestratti Maqui was studied using an animal model of rats subjected to

ischemia and reperfusion. Following reperfusion are witnessing an important phenomenon at the level

of lipoperoxidation infarction, pretreatment with extract Maqui, of the experimental animals has

demonstrated the ability to prevent the formation of TBARS, a known biomarker of peroxidation (Cèspedes et al. 2008).

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Inflammation

Two important enzymes involved in the activation of inflammatory responses are the inducible NO synthase

(iNOS) and cyclooxygenase -2 (COX-2), thus inhibiting the expression of these enzymes may help reduce

inflammation and events Related. A study conducted to evaluate the anti-inflammatory action of A.chilensis

found a high capacity of inhibition of the expression of iNOS (61.8%) exerted from the extract of Maqui. This

effect was comparable to that of quercetin, powerful anti-inflammatory agent used as a control (Schreckinger et

al., 2010). To better understand the role of the extracts of Maqui in inflammation, the same study also assessed

the expression of COX-2 and prostaglandin production. The Maqui extract inhibits COX-2 at levels between 20

and 40% and significantly reduces the production of prostaglandin E2.

Other studies have shown that the delfinidine inhibit the expression of COX-2 induced by the inflammatory

cytokine IL-1β and the subsequent production of prostaglandins in human chondrocytes over that block the

expression of the transcription factor NF-kB, the main regulator of genes involved in inflammation, immune

responses and apoptosis (Haseeb et al., 2013).

Maqui and diabetes

Studying a formula rich in anthocyanins obtained from Maqui berry, was identified a new possible

application, or the control of hyperglycemia and the prevention of complications in patients with type

II diabetes (Rojo et al., 2012).

Oral administration of anthocyanins is able to reduce the fasting hyperglycemia in obese diabetic

mice, and delphinidin-3-sambubioside-5-glucoside, abundantly present in the extracts of the fruit, is

responsible for the antidiabetic effects observed in vivo. In addition, there has been an increase in

glucose tolerance by mice, suggesting a potential increase in insulin sensitivity made from the extract

tested. In addition, the extract of the berries of Maqui significantly increased glucose uptake at the

level of the muscle cells.

Maqui and neuroprotection

Oxidative stress and damage to macromolecules brain are important processes involved in

neurodegenerative diseases.

The lack of decisive therapies for Alzheimer's disease and biomarkers that help early identification

are necessary pharmacological strategies or nutraceutical that slow the progress of the disease.

Specific studies have shown the positive effects of polyphenols in various models of

neurodegeneration (Fuentealba et al., 2012). As a rich source of polyphenols also Maqui has been

studied in order to evaluate the neuroprotective effects (Fuentealba et al., 2012). Using a cellular

model of hippocampal neurons, it has been observed that treatment with extract partially prevents

Maqui induced toxicity amiloide, reducing cell death. It also prevents the modification of neuronal

morphology characterized by reduction of dendritic processes and thickening of the axon, generated

by hyperphosphorylation of tau protein with the consequent increase of about two and a half times the

size.

ALMA MATER STUDIORUM - UNIVERSITÀ DI BOLOGNA C.SO D’AUGUSTO 237 - 47921 RIMINI - ITALIA - TEL. +39 0541 434601 - FAX +39 0541 434607

TE 'GREEN

The tea plant, whose scientific name is Thea sinensis (Chinese tea), belongs to the species Camellia

sinensis, the family Theaceae. The tea plant is an evergreen tree native to Asia, particularly in Burma,

China, Ceylon, India (province of Assam), Japan. The tree grows well in acidic soils, soft and well-

drained soil, rich in organic matter; from 500 to 2000 m above sea level, in tropical or sub-tropical

areas with adequate rainfall.

Green tea has been known for about 5000 years. This variety of tea is called "unfermented" because

the leaves, not being subjected to this procedure, retain their green color, producing an infusion clear

and fragrant, with a slightly amaro.Il green tea accounts for about 20% of the world consumption.

The tea is a complex mixture of substances, for the most part present in small amounts. The particular

concentration of the individual components varies with the type of plant, the climate, the season, the

growth conditions, the age of the leaves and the way in which it is handled. On average, in 100 g of

tea, there were the following components:

Caffeine (2-4%)

Amino Acids (4%)

Lignin (6.5%)

Organic acids (1.5%)

Protein (15%)

Chlorophyll (0.5%)

Polyphenols (8-12%)

Vitamin A

Vitamin B1

Vitamin B2

Vitamin C.

The yellow-green color of fresh extracts is due to chlorophyll contained in them (LA Mitscher et al.,

1997).

Tea contains over 35% of polyphenols by dry weight, variable depending on the production process

and an amino acid content of 2-3%.

Also green tea is rich in polyphenols (mainly catechins) and simple phenolic acids.

Many of the health benefits of tea are attributed to the antioxidant decatechine contained therein. In

the absorption step, through the intestinal membrane, the polyphenols are transformed into the

corresponding glucuronides and sulfates. Currently, there are recent studies on the bioavailability of

flavan-3-ols following intake of green tea from the man. The main metboliti reach peak plasma

concentrations of the order of nomolarità about 2 hours after dosing, indicating that absorption

occurs in the small intestine. The concentrations then decreased, and only traces remain eight hours

after ingestion. The urinary excretion of metabolites over a period of 24 hours after the consumption

of green tea catechin corresponds to 28.5% of the ingested and to 11.4% of gallocatechine,

suggesting absorption superior to that of most other flavonoids ( Clifford MN er al., 2013).

Most flavonoids ingested is not absorbed and is degraded by the gut microflora. The enzymes of the

bacteria catalyze various reactions, including hydrolysis, the opening of the heterocyclic ring

containing the oxygen atom, the dehydroxylation and decarboxylation. Since these processes are

ALMA MATER STUDIORUM - UNIVERSITÀ DI BOLOGNA C.SO D’AUGUSTO 237 - 47921 RIMINI - ITALIA - TEL. +39 0541 434601 - FAX +39 0541 434607

different products phenolic acids according to the structure of the flavonoids concerned (Pietta PG et

al., 1997). These phenolic acids can be reabsorbed and replaced with a conjugation and an O-

methylation in the liver, so they can get into the bloodstream.

This aspect is relevant for protection against reactive oxygen species (ROS), for two

reasons. The first is that the liberated phenolic acids represent a large fraction of the ingested

flavonoids (30-60

%); the second is that some of these acids, maintaining their catecholic structure, possess an ability

to bind radicals similar to that of the precursors (Merfort I. et al., 1997).

This suggests that these metabolites may take part in the antioxidant protection. So these compounds

exert their activity only in the digestive tract, but once absorbed continue to exert their antioxidant

activity outside of the digestive tract.

The green tea catechins Catechins are a group of compounds derived from (+) - catechin (Figure 2), a molecule belonging to

the family of flavan-3-ols, characterized by having four hydroxyl functions in position 5, 7, 3 ', 4'.

Figure 2. Structure of the (+) - catechin.

Catechins incorporating three hydroxyl functions in the ring B are called gallocatechine; those that

present as substituent in position 3 of the C molecule of gallic acid are esters of catechins and gallic

are called catechingallati.

The four most common green tea catechins, known as green tea catechin, are:

Epicatechin (EC)

epigallocatechin (EGC)

Epicatechingallato (ECG)

epigallocatechin gallate (EGCG).

Of polyphenols, the most interest are epigallocatechin gallate (EGCG) and epigallocatechin (EGC).

Green tea is an excellent source of catechins, in particular from 100 g of dry leaves of green tea can

obtain 7.4 g of catechins: EGCG are the main fraction followed in order by ECG, EGC, EC. Is

present, but in much smaller quantities, also gallocatechingallato (GCG).

Regarding the antioxidant capacity of catechins, numerous studies have been performed: it was shown

ALMA MATER STUDIORUM - UNIVERSITÀ DI BOLOGNA C.SO D’AUGUSTO 237 - 47921 RIMINI - ITALIA - TEL. +39 0541 434601 - FAX +39 0541 434607

that the GTC possess a strong inhibitory power against lipid oxidation; Zhang Z.H. et al. (1997) have

found that the isomers purified extracts from green tea are the protective agents

oxidation of LDL and cell membranes of red blood cells; Vinson J. A. et al., (1998), have argued that

the catechins are the most potent inhibitors of the oxidation process catalyzed by the copper ion of

plasma lipoproteins in vitro.

Effects of green tea In recent decades, numerous studies have shown the positive effects of tea, especially green tea,

against several diseases.

At tea, especially green tea, have been varied capabilities in drug research, many of which related to

the antioxidant activity of polyphenols contained therein. Among these properties we have:

antihypertensive activity, antioxidant, anti-atherosclerotic, anticarcinogenetica, cholesterol lowering (P

Bhardwaj et al., 2013; Li MJ. Et al., 2014) increase in the production of HDL (JA Vinson and YA

Dabbagh, 1998), reduction of 'absorption of sodium and glucose.

The consumption of green tea was associated with decreased cardiovascular disease risk through a

decrease in triglycerides and serum cholesterol, increase HDL and therefore a reduced atherogenic

index (K. Imai et al., 1995). It seems that the tea has also a preventive effect to chronic diseases such

as cancer (Dreosti IE, 1996), anti-inflammatory effects.

It is shown that the gallates of epicatecolo and epigallocatecolo (EGCG) act as scavengers of free

radicals. In particular, two epidemiological studies have highlighted the role of green tea as a dietary

antioxidant. (Shim J.S. et al., 1995).

This seems to be due to the absence of the carbonyl group in C catechin with respect to the

quercetin.

Tea is also used in the composition of cosmetic products and pharmaceuticals is to carry out various

functions: cure warts and calluses; infections of the oral cavity; sores and infections of animals; for

sunburns, rashes of newborns; acne; as anti-dandruff agents.

The tea also has a germicidal effect on colon bacilli and staphylococci on (Reygaert WC, 2014).

EXTRACT POMEGRANATE

The pomegranate (P.Granatum), is considered one of the oldest edible fruits. Native of the regions of

the Himalayas, its cultivation extends to Iran but has been naturalized and cultivated since ancient

times throughout the Mediterranean area and is still an integral part of the diet in these countries.

One of the research areas of great relevance and of greatest interest is the study of bioactive

components of pomegranate and their effects on the improvement of human health. It is verified by

numerous scientific studies, is the pomegranate is derived products contain several components that

can prevent disease and improve health status (Larrosa M, 2006).

The pomegranate fruit is a rich source of polyphenolic compounds: these can be divided into simple

molecules and polymers of the latter characterized by a greater molecular weight. Among the first

remember flavonoids (such as catechins, phloridzin, and quercetin); Anthocyanins are the subgroup

most representative and are responsible for the characteristic color of the pomegranate. In

pomegranate juice are also several phenolic acids, in particular gallic acid, chlorogenic, caffeic, ferulic

and coumaric. In addition to the catechins are present in pomegranate other flavan-3-ols such as

epicatechin and epigallocatechin (De Pascual-Teresa S, 2000).

Tannins are polyphenolic compounds with high molecular weight. The skin, but in general all parts of

the pomegranate is rich in hydrolysable tannins, in particular ellagitannins and gallo tannins, the most

common classes of compounds in pomegranate. The bioactivity of the pomegranate is largely due to

ALMA MATER STUDIORUM - UNIVERSITÀ DI BOLOGNA C.SO D’AUGUSTO 237 - 47921 RIMINI - ITALIA - TEL. +39 0541 434601 - FAX +39 0541 434607

the presence of these compounds the main ones punicalagins and garnets.

The studies have focused on the effects of antioxidants in vitro, ex vivo and in vivo, in particular the

pomegranate juice, oil seeds and extracts obtained from the peel, whose antioxidant capacity was

always placed in relation to their chemical composition .

In addition to the different uses typical of ancient traditional medicines, the use of the pomegranate is

justified by the anti-atherosclerotic and other positive effects such as chemotherapeutic and

chemopreventive activity especially in prostate cancer. Other effects of pomegranate juice have been

reported such as the antiinflammatory activity, the reduction of platelet aggregation, reduction of the

modifications pro- atherogenic LDL, the reduction of oxidative stress in the macrophages, the positive

effects in combating obesity and diabetes and modification of the lipid profile based on the inhibition

of the increased uptake and fatty acid oxidation that occurs in cardiac conditions of diabetes. Most of

these effects have been attributed to the high antioxidant capacity of pomegranate juice, probably due

to the presence of a complex mixture of fitocomponent with biological activity.

The part of pomegranate with the highest content of polyphenols, particularly tannins and

ellagitannins, and that presents the greatest antioxidant activity is the skin, it was found that the peel

extract, compared to extracts of other parts of the plant, has a capacity more high to chelate metals.

This result was confirmed by analyzing the ability of scavenging and prevention of the formation of

different radical species and the inhibition of LDL oxidation. Even in this case, the high antioxidant

activity has been attributed to the high polyphenol content of the peel.

The extracts of the peel of pomegranate have also been shown to have activity antimutagenica. This

activity does not seem to be correlated with the antioxidant activity, but the study authors speculate

that the absence of a correlation can be attributed to differences / quantitative composition in

polyphenols and other bioactive compounds present in the extracts. The antioxidant capacity of pomegranate juice has been evaluated in several studies both in vitro, ex

vivo and in vivo since it is the product derived from the pomegranate most commonly consumed. The

antioxidant capacity of the juice is lower than that of the peel, but greater than that of the seeds and

found to be three times higher and that of red wine and green tea, evaluated with the same analytical

techniques (Faria A. et al., 2011).

EXTRACT ACEROLA

The acerola (Malpighia glabra) is a wild plant grown in areas of tropical and subtropical climate. The

acerola is native from southern Mexico, Central America and South America. The result is

represented by a drupe red color of the variable diameter between 1 - 4 cm and a weight of between 2

and 15 g. From a nutritional standpoint the fruit contains macro- and micro-nutrients: protein (0.21 to

0.80 g / 100 g), fat (0.23 to 0.80 g / 100g), carbohydrates (3.6 to 7.80 g / 100 g), minerals (iron,

calcium, phosphorus) and vitamins (thiamine, riboflavin, piridoxine). Its high content of vitamin C,

between 695 and 4827 mg / 100 g is among the highest in the plant kingdom. As a source of vitamin

C acerola is having an interest cresente and consumption continues to increase in recent years. In

addition to the nutrient content, recent indications show the presence of carotenoids and flavonoids

that provide an important added value and help to justify its use as an antioxidant (Mezadri T., et al

2006). Recent studies, conducted in an animal model of mice have suggested that the acerola juice

possesses an anti-inflammatory (Dias FM., Et al. 2014)

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EXTRACT SAMBUCO

The elderberries are used in traditional medicine German for various applications. Prepared from

fruits of elder are a source of antioxidants and are traditionally used for their antidepressant effects,

antiviral and antimicrobial. There is no doubt that the fruits of elder may have some utility in terms

of protective effect against oxidative stress; is shown in fact, that they contain significant amounts of

flavonoids, mainly anthocyanins, such as: cianidin 3-O, O- 5-diglucoside, cianidin-3-O-

sambubioside, cianidin-3-O-sambubioside-5-O-glucoside, cyanidin-3-O- rhamnoglucoside,

cyanidin-3-Oxyloglucoside. In these compounds is added the presence of essential oils, and those of

some micronutrients such as vitamin C, folic acid, vitamins B2, B6, niacin and b-caretene (Mikulic-

Petkovsek M. et al., 2014; Vlachojannis JE. Et al ., 2010).

On the basis of the composition in polyphenolic molecules antioxidant effects, anti-microbial and

anti-inflammatory seem possible, however studies, and are available to support these assumptions

are not yet sufficient, despite that elderberry extracts are commonly used in the preparation of

formilazioni and antioxidant supplements.

As for the effects of antidepressants, a study has recently evaluated the action in an animal model of

rodents concluding that estrtti methanol elderberry have an effect

antidepressant (M. Mahmoudi et al., 2014).

SEED EXTRACT SCREW AND RED GRAPES

The grapevine is a plant native to southern Europe and western Asia, but is now cultivated in all

temperate zones of the earth. The seeds of grapes and their skins are rich in various active

components including flavonoids, polyphenols, anthocyanins, proanthocyanidins, procyanidins, and

resveratrol.

All parts of the screw are rich in polyphenols, however, 60-70% of the polyphenols found in grape

seeds.

The polyphenols in grape seed are derivatives of flavan-3 -ol. The major compounds are (+) -

catechin, (-) -

epicatechin, (-) - epicatechin-3-O-gallate and procyanidins. Regarding the anthocyanins in the screw

was identified the presence of cyanidin, delphinidin, peonidin, petunidin, and malvidin in the forms

coumaroilglucoside 3-, 3-caffeoilglucoside, 3,5-diglucoside, 3 and fine 3-caffeoyl-5-dig

Given the high content of phenolic molecules, extracts of grape seeds and red grapes exert a powerful

antioxidant. This action has been highlighted in several experimental models and besides to appear as

a simple direct antioxidant action able to protect DNA from oxidative damage and lipid peroxidation,

is also manifested in the ability of these extracts to inhibit enzymes acting prossidante as xanthine

oxidase .

In addition to the antioxidant extracts of lives have been shown to exert other effects such as degrees,

cardioprotective action, which manifests itself with a vasodilatory action and a better recovery

following phenomena of ischemia / reperfusion, action hepatoprotective, an antimicrobial effect and a

positive action on the central nervous system where they reduce peroxidation maintaining the

plasticity of neuronal membranes (Nassiri-Asl M. et al., 2009).

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