Phenoxy Radical
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A polyphenol antioxidant is a hypothesized type of
antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...
studied
in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...
. Numbering over 4,000 distinct chemical structures mostly from
plant Plants are the eukaryotes that form the Kingdom (biology), kingdom Plantae; they are predominantly Photosynthesis, photosynthetic. This means that they obtain their energy from sunlight, using chloroplasts derived from endosymbiosis with c ...
s, such polyphenols have not been demonstrated to be antioxidants
in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, an ...
. In vitro at high experimental doses, polyphenols may affect cell-to-cell signaling,
receptor Receptor may refer to: * Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...
sensitivity, inflammatory
enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
activity or
gene regulation Regulation of gene expression, or gene regulation, includes a wide range of mechanisms that are used by cells to increase or decrease the production of specific gene products (protein or RNA). Sophisticated programs of gene expression are wide ...
. None of these hypothetical effects has been confirmed in humans by high-quality
clinical research Clinical research is a branch of medical research that involves people and aims to determine the effectiveness (efficacy) and safety of medications, devices, diagnostic products, and treatment regimens intended for improving human health. The ...
, .


Sources of polyphenols

The main source of polyphenols is dietary, since they are found in a wide array of
phytochemical Phytochemicals are naturally-occurring chemicals present in or extracted from plants. Some phytochemicals are nutrients for the plant, while others are metabolites produced to enhance plant survivability and reproduction. The fields of ext ...
-bearing foods. For example,
honey Honey is a sweet and viscous substance made by several species of bees, the best-known of which are honey bees. Honey is made and stored to nourish bee colonies. Bees produce honey by gathering and then refining the sugary secretions of pl ...
; most
legume Legumes are plants in the pea family Fabaceae (or Leguminosae), or the fruit or seeds of such plants. When used as a dry grain for human consumption, the seeds are also called pulses. Legumes are grown agriculturally, primarily for human consum ...
s; fruits such as
apple An apple is a round, edible fruit produced by an apple tree (''Malus'' spp.). Fruit trees of the orchard or domestic apple (''Malus domestica''), the most widely grown in the genus, are agriculture, cultivated worldwide. The tree originated ...
s,
blackberries BlackBerry is a discontinued brand of handheld devices and related mobile services, originally developed and maintained by the Canadian company Research In Motion (RIM, later known as BlackBerry Limited) until 2016. The first BlackBerry device ...
,
blueberries Blueberries are a widely distributed and widespread group of perennial flowering plants with blue or purple berries. They are classified in the section ''Cyanococcus'' with the genus ''Vaccinium''. Commercial blueberries—both wild (lowbush) ...
,
cantaloupe The cantaloupe ( ) is a type of true melon (''Cucumis melo'') with sweet, aromatic, and usually orange flesh. Originally, ''cantaloupe'' refers to the true cantaloupe or European cantaloupe with non- to slightly netted and often ribbed rind. ...
,
pomegranate The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punica, Punicoideae, that grows between tall. Rich in symbolic and mythological associations in many cultures, it is thought to have o ...
,
cherries A cherry is the fruit of many plants of the genus ''Prunus'', and is a fleshy drupe (stone fruit). Commercial cherries are obtained from cultivars of several species, such as the sweet ''Prunus avium'' and the sour ''Prunus cerasus''. The name ...
,
cranberries Cranberries are a group of evergreen dwarf shrubs or trailing vines in the subgenus ''Oxycoccus'' of the genus ''Vaccinium''. Cranberries are low, creeping shrubs or vines up to long and in height; they have slender stems that are not t ...
,
grape A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began approximately 8,0 ...
s,
pear Pears are fruits produced and consumed around the world, growing on a tree and harvested in late summer into mid-autumn. The pear tree and shrub are a species of genus ''Pyrus'' , in the Family (biology), family Rosaceae, bearing the Pome, po ...
s,
plum A plum is a fruit of some species in Prunus subg. Prunus, ''Prunus'' subg. ''Prunus'.'' Dried plums are often called prunes, though in the United States they may be labeled as 'dried plums', especially during the 21st century. Plums are ...
s,
raspberries The raspberry is the edible fruit of several plant species in the genus ''Rubus'' of the Rosaceae, rose family, most of which are in the subgenus ''Rubus#Modern classification, Idaeobatus''. The name also applies to these plants themselves. Ras ...
, aronia berries, and
strawberries The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown hybrid plant cultivated worldwide for its fruit. The genus ''Fragaria'', the strawberries, is in the rose family, Rosaceae. The fruit is appreciated f ...
(berries in general have high polyphenol content) and
vegetable Vegetables are edible parts of plants that are consumed by humans or other animals as food. This original meaning is still commonly used, and is applied to plants collectively to refer to all edible plant matter, including edible flower, flo ...
s such as
broccoli Broccoli (''Brassica oleracea'' var. ''italica'') is an edible green plant in the Brassicaceae, cabbage family (family Brassicaceae, genus ''Brassica'') whose large Pseudanthium, flowering head, plant stem, stalk and small associated leafy gre ...
,
cabbage Cabbage, comprising several cultivars of '' Brassica oleracea'', is a leafy green, red (purple), or white (pale green) biennial plant grown as an annual vegetable crop for its dense-leaved heads. It is descended from the wild cabbage ( ''B.& ...
,
celery Celery (''Apium graveolens'' Dulce Group or ''Apium graveolens'' var. ''dulce'') is a cultivated plant belonging to the species ''Apium graveolens'' in the family Apiaceae that has been used as a vegetable since ancient times. The original wild ...
,
onion An onion (''Allium cepa'' , from Latin ), also known as the bulb onion or common onion, is a vegetable that is the most widely cultivated species of the genus '' Allium''. The shallot is a botanical variety of the onion which was classifie ...
and
parsley Parsley, or garden parsley (''Petroselinum crispum''), is a species of flowering plant in the family Apiaceae that is native to Greece, Morocco and the former Yugoslavia. It has been introduced and naturalisation (biology), naturalized in Eur ...
are rich in polyphenols.
Red wine Red wine is a type of wine made from dark-colored grape varieties - (red grapes.) The color of the wine can range from intense violet, typical of young wines, through to brick red for mature wines and brown for older red wines. The juice fro ...
,
chocolate Chocolate is a food made from roasted and ground cocoa beans that can be a liquid, solid, or paste, either by itself or to flavoring, flavor other foods. Cocoa beans are the processed seeds of the cacao tree (''Theobroma cacao''); unprocesse ...
, black tea,
white tea White tea may refer to one of several styles of tea which generally feature young or minimally processed leaves of the ''Camellia sinensis'' plant. Currently there is no generally accepted definition of white tea and very little international ...
,
green tea Green tea is a type of tea made from the leaves and buds of the '' Camellia sinensis'' that have not undergone the withering and oxidation process that creates oolong teas and black teas. Green tea originated in China in the late 1st millenn ...
,
olive oil Olive oil is a vegetable oil obtained by pressing whole olives (the fruit of ''Olea europaea'', a traditional Tree fruit, tree crop of the Mediterranean Basin) and extracting the oil. It is commonly used in cooking for frying foods, as a cond ...
and many
grain A grain is a small, hard, dry fruit (caryopsis) – with or without an attached husk, hull layer – harvested for human or animal consumption. A grain crop is a grain-producing plant. The two main types of commercial grain crops are cereals and ...
s are sources. Ingestion of polyphenols occurs by consuming a wide array of plant foods.


Biochemical theory

The regulation theory considers a polyphenolic ability to scavenge
free radical A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing. Ageing Biogerontology Biological processes Causes of death Cellular processes Gerontology Life extension Metabolic disorders Metabolism ...
s and up-regulate certain metal
chelation Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...
reactions. Various
reactive oxygen species In chemistry and biology, reactive oxygen species (ROS) are highly Reactivity (chemistry), reactive chemicals formed from diatomic oxygen (), water, and hydrogen peroxide. Some prominent ROS are hydroperoxide (H2O2), superoxide (O2−), hydroxyl ...
, such as
singlet oxygen Singlet oxygen, systematically named dioxygen(singlet) and dioxidene, is a gaseous inorganic chemistry, inorganic chemical with the formula O=O (also written as or ), which is in a quantum state where all electrons are Radical (chemistry), spin p ...
,
peroxynitrite Peroxynitrite (sometimes called peroxonitrite) is an ion with the formula ONOO−. It is a structural isomer of nitrate, Preparation Peroxynitrite can be prepared by the reaction of superoxide with nitric oxide: : It is prepared by the rea ...
and
hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...
, must be continually removed from cells to maintain healthy metabolic function. Diminishing the concentrations of reactive oxygen species can have several benefits possibly associated with
ion transport In biology, an ion transporter is a transmembrane protein that moves ions (or other small molecules) across a biological membrane to accomplish many different biological functions, including cellular communication, maintaining homeostasis, energy ...
systems and so may affect
redox signaling ''Antioxidants & Redox Signaling '' is a peer-reviewed scientific journal covering reduction–oxidation (redox) signaling and antioxidant research. It covers topics such as reactive oxygen species/reactive nitrogen species (ROS/RNS) as messenger ...
. There is no substantial evidence, however, that dietary polyphenols have an antioxidant effect in vivo. The “deactivation” of oxidant species by polyphenolic antioxidants (POH) is based, with regard to food systems that are deteriorated by peroxyl radicals (R•), on the donation of hydrogen, which interrupts chain reactions: :R• + PhOH → R-H + PhO• Phenoxyl radicals (PO•) generated according to this reaction may be stabilized through
resonance Resonance is a phenomenon that occurs when an object or system is subjected to an external force or vibration whose frequency matches a resonant frequency (or resonance frequency) of the system, defined as a frequency that generates a maximu ...
and/or intramolecular hydrogen bonding, as proposed for
quercetin Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor ...
, or combine to yield
dimer Dimer may refer to: * Dimer (chemistry), a chemical structure formed from two similar sub-units ** Protein dimer, a protein quaternary structure ** d-dimer ** TH-dimer * Dimer model, an item in statistical mechanics, based on ''domino tiling'' * ...
isation products, thus terminating the chain reaction: :PhO• + PhO•→ PhO-OPh


Potential biological consequences

Consuming dietary polyphenols have been evaluated for biological activity in vitro, but there is no evidence from high-quality
clinical research Clinical research is a branch of medical research that involves people and aims to determine the effectiveness (efficacy) and safety of medications, devices, diagnostic products, and treatment regimens intended for improving human health. The ...
that they have effects in vivo. Preliminary research has been conducted and regulatory status was reviewed in 2009 by the U.S.
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...
(FDA), with no recommended intake values established, indicating absence of proof for nutritional value. Other possible effects may result from consumption of foods rich in polyphenols, but are not yet proved scientifically in humans; accordingly, health claims on food labels are not allowed by the FDA.


Difficulty in analyzing effects of specific chemicals

It is difficult to evaluate the physiological effects of specific polyphenols because a large number of individual phenolic compounds may occur in a single food and their fate in vivo cannot be measured. The
Oxygen Radical Absorbance Capacity Oxygen radical absorbance capacity (ORAC) was a method of measuring antioxidant capacities in biological samples ''in vitro''. Because no physiological proof ''in vivo'' existed in support of the free-radical theory or that ORAC provided informatio ...
(ORAC) test is a laboratory indicator of antioxidant potential in foods and
dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...
s. However, ORAC results cannot be confirmed as physiologically applicable and have been designated as unreliable.


Practical aspects of dietary polyphenols

There is debate regarding the total body absorption of dietary intake of polyphenolic compounds. While some indicate potential health effects of certain specific polyphenols, most studies demonstrate low
bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...
and rapid excretion of polyphenols, indicating their potential roles only in small concentrations in vivo. More research is needed to understand the interactions between a variety of these chemicals acting in concert within the human body.


Topical application of polyphenols

There is no substantial evidence that reactive oxygen species play a role in the process of skin
aging Ageing (or aging in American English) is the process of becoming Old age, older until death. The term refers mainly to humans, many other animals, and fungi; whereas for example, bacteria, perennial plants and some simple animals are potentiall ...
. The skin is exposed to various
exogenous In a variety of contexts, exogeny or exogeneity () is the fact of an action or object originating externally. It is the opposite of endogeneity or endogeny, the fact of being influenced from within a system. Economics In an economic model, an ...
sources of
oxidative stress Oxidative stress reflects an imbalance between the systemic manifestation of reactive oxygen species and a biological system's ability to readily detoxify the reactive intermediates or to repair the resulting damage. Disturbances in the normal ...
, including
ultraviolet Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of ...
radiation whose spectral components may be responsible for the
extrinsic In science and engineering, an intrinsic property is a property of a specified subject that exists itself or within the subject. An extrinsic property is not essential or inherent to the subject that is being characterized. For example, mass i ...
type of skin aging, sometimes termed
photoaging Photoaging or photoageing (also known as "dermatoheliosis") is a term used for the characteristic changes to skin induced by chronic Ultraviolet, UVA and UVB exposure. Effects of UV light Molecular and genetic changes UVB rays are a primary ...
. Controlled long-term studies on the efficacy of low molecular weight antioxidants in the prevention or treatment of
skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other animal coverings, such as the arthropod exoskeleton, have different ...
aging in humans are absent.


Combination of antioxidants in vitro

Experiments on
linoleic acid Linoleic acid (LA) is an organic compound with the formula . Both alkene groups () are ''cis''. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 ''cis''-9,12. A linoleate is a salt or ester of this acid. Linoleic acid is a polyunsat ...
subjected to
2,2′-azobis (2-amidinopropane) dihydrochloride The comma is a punctuation mark that appears in several variants in different languages. Some typefaces render it as a small line, slightly curved or straight, but inclined from the vertical; others give it the appearance of a miniature fille ...
-induced oxidation with different combinations of phenolics show that binary mixtures can lead to either a synergetic effect or to an antagonistic effect. Antioxidant levels of purified anthocyanin extracts were much higher than expected from anthocyanin content indicating
synergistic Synergy is an interaction or cooperation giving rise to a whole that is greater than the simple sum of its parts (i.e., a non-linear addition of force, energy, or effect). The term ''synergy'' comes from the Attic Greek word συνεργία ' f ...
effect of anthocyanin mixtures.


Antioxidant capacity tests

*
Oxygen radical absorbance capacity Oxygen radical absorbance capacity (ORAC) was a method of measuring antioxidant capacities in biological samples ''in vitro''. Because no physiological proof ''in vivo'' existed in support of the free-radical theory or that ORAC provided informatio ...
(ORAC) *
Ferricyanide Ferricyanide is the name of the anion CN)6sup>3−. It is also called hexacyanoferrate(III) and in rare, but systematic name">systematic nomenclature, hexacyanidoferrate(III). The most common salt of this anion is potassium ferricyanide, a red ...
reducing power * 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity


See also

*
List of phytochemicals in food The following is a list of phytochemicals present in foods. Terpenoids (isoprenoids) Carotenoids ( tetraterpenoids) ''Carotenes'' orange pigments * α-Carotene – to vitamin A: carrots, pumpkins, maize, tangerine, orange * β-Carote ...
*
List of antioxidants in food This is a list of antioxidants naturally occurring in food. Vitamin C and vitamin E – which are ubiquitous among raw plant foods – are confirmed as dietary antioxidants, whereas vitamin A becomes an antioxidant following metabolism of ...
*
Health effects of polyphenols Polyphenols () are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as ...
*
Free-radical theory The free radical theory of aging states that organisms age because cells accumulate free radical damage over time. A free radical is any atom or molecule that has a single unpaired electron in an outer shell.Erbas M, Sekerci H. "Importance of Free ...
*
Nitric oxide Nitric oxide (nitrogen oxide, nitrogen monooxide, or nitrogen monoxide) is a colorless gas with the formula . It is one of the principal oxides of nitrogen. Nitric oxide is a free radical: it has an unpaired electron, which is sometimes den ...
*
Resveratrol Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacterium, ba ...
*
Astaxanthin Astaxanthin is a keto- carotenoid within a group of chemical compounds known as carotenoids or terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-solu ...


References

{{DEFAULTSORT:Polyphenol Antioxidant Angiology Chemopreventive agents Antioxidants