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Encyclopedia > Anthocyanin
Plants with abnormally high anthocyanin quantities are popular as ornamental plants - here, a selected purple-leaf cultivar of European Beech
Plants with abnormally high anthocyanin quantities are popular as ornamental plants - here, a selected purple-leaf cultivar of European Beech

Anthocyanins (from Greek: ἀνθός (anthos) = flower + κυανός (kyanos) = blue) are water-soluble vacuolar flavonoid pigments that appear red to blue, according to pH. They are synthesized exclusively by organisms of the plant kingdom, and have been observed to occur in all tissues of higher plants, providing color in leaves, stems, roots, flowers, and fruits. Fagus sylvatica Atropurpurea (Purple European Beech) These trees are at Longwood Gardens. ... Fagus sylvatica Atropurpurea (Purple European Beech) These trees are at Longwood Gardens. ... An ornamental plant is a plant that is grown for its ornamental qualities, rather than for its commercial or other value. ... Binomial name Fagus sylvatica L. The European Beech or Common Beech (Fagus sylvatica) is a deciduous tree belonging to the beech family Fagaceae. ... It has been suggested that Solid solubility be merged into this article or section. ... == Schematic of typical animal cell, showing subcellular components. ... Molecular structure of flavone The term flavonoid refers to a class of plant secondary metabolites based around a phenylbenzopyrone structure. ... In biology, pigment is any material resulting in color in plant or animal cells which is the result of selective absorption. ... pH is a measure of the acidity of a solution in terms of activity of hydrogen ions (H+). For dilute solutions, however, it is convenient to substitute the activity of the hydrogen ions with the molarity (mol/L) of the hydrogen ions (however, this is not necessarily accurate at higher... Divisions Green algae land plants (embryophytes) non-vascular embryophytes Hepatophyta - liverworts Anthocerophyta - hornworts Bryophyta - mosses vascular plants (tracheophytes) seedless vascular plants Lycopodiophyta - clubmosses Equisetophyta - horsetails Pteridophyta - true ferns Psilotophyta - whisk ferns Ophioglossophyta - adderstongue ferns seed plants (spermatophytes) †Pteridospermatophyta - seed ferns Pinophyta - conifers Cycadophyta - cycads Ginkgophyta - ginkgo Gnetophyta - gnetae Magnoliophyta... A biological tissue is a group of biological cells that perform a similar function. ... The leaves of a Beech tree A leaf with laminar structure and pinnate venation In botany, a leaf is an above-ground plant organ specialized for photosynthesis. ... A stem is the above ground axis of a vascular plant. ... ROOT is an object-oriented software package developed by CERN. It was originally designed for particle physics data analysis and contains several features specific to this field, but it is also commonly used in other applications such as astronomy and data mining. ... Wildflowers A flower is the reproductive organ of those plants classified as angiosperms ( flowering plants; Division Magnoliophyta). ... Fruit stall in Barcelona, Spain. ...

Contents

Function

In flowers, anthocyanin pigments function as pollinator attractants, and in fruits, the colorful skins attract animals which will eat the fruits and disperse the seeds. In photosynthetic tissues (such as leaves), anthocyanins have been shown to act as a "sunscreen", protecting cells from photo-damage by absorbing UV and blue-green light, thereby protecting the tissues from photoinhibition, or high light stress. This has been shown to occur in red juvenile leaves, autumn leaves, and broad-leaved evergreen leaves that turn red during the winter. It is also thought that red coloration of leaves may camouflage leaves from herbivores blind to red wavelengths, or signal inpalatability to herbivores, since anthocyanin synthesis often coincides with synthesis of inpalatble phenolic compounds.


In addition to their role as light-attenuators, anthocyanins also act as powerful antioxidants, helping to protect the plant from radicals formed by UV light and during metabolic processes. This antioxidant property is conserved even after consumption by another organism, which is another reason why fruits and vegetables with red skins and tissues are a nutritious food source. An antioxidant is a chemical that reduces the rate of particular oxidation reactions in a specific context, where oxidation reactions are chemical reactions that involve the transfer of electrons from a substance to an oxidising agent. ... Note: Ultraviolet is also the name of a 1998 UK television miniseries about vampires. ...


Occurrence


foodstuff Anthocyanin in mg per
100 g foodstuff
chokeberry 200-1000
aubergine 750
orange ~200
blackberry ~115
vaccinium 80-420
raspberry 10-60
cherry 350-400
redcurrant 80-420
red grape 30-750
red wine 24-35

Not all land plants contain anthocyanin and in the Caryophyllales, Cactus and Galium mollugo they are replaced by betacyanins. Species Aronia arbutifolia (L.) Pers. ... Binomial name Solanum melongena L. The aubergine, eggplant, or brinjal (Solanum melongena) is a solanaceous plant bearing a fruit of the same name, commonly used as a vegetable in cooking. ... Percentages are relative to US RDI values for adults. ... The BlackBerry is a wireless handheld device introduced in 1999 which supports push e-mail, mobile telephone, text messaging, internet faxing, web browsing and other wireless information services. ... Species See text Vaccinium is a genus of shrubs in the plant Family Ericaceae including the cranberry, blueberry, lingonberry, bilberry, and huckleberry. ... Binomial name Rubus idaeus L. The Raspberry or Red Raspberry (Rubus idaeus) is a plant that produces a tart, sweet, red composite fruit in late summer or early autumn. ... Species Several, including: Prunus apetala Prunus avium (Wild/Sweet Cherry) Prunus campanulata Prunus canescens Prunus cerasus (Sour Cherry) Prunus concinna Prunus conradinae Prunus dielsiana Prunus emarginata (Bitter Cherry) Prunus fruticosa Prunus incisa Prunus litigiosa Prunus mahaleb (Saint Lucie Cherry) Prunus maximowiczii Prunus nipponica Prunus pensylvanica (Pin Cherry) Prunus pilosiuscula Prunus... Species Ribes rubrum The Redcurrant (Ribes rubrum) is a member of the genus Ribes in the gooseberry family Grossulariaceae. ... Species Vitis acerifolia Vitis aestivalis Vitis amurensis Vitis arizonica Vitis x bourquina Vitis californica Vitis x champinii Vitis cinerea Vitis x doaniana Vitis girdiana Vitis labrusca Vitis x labruscana Vitis lincecumii Vitis monticola Vitis mustangensis Vitis x novae-angliae Vitis palmata Vitis riparia Vitis rotundifolia Vitis rupestris Vitis shuttleworthii Vitis... Wine is an alcoholic beverage produced by the fermentation of the juice of fruits, usually grapes. ... Families Achatocarpaceae Aizoaceae (Fig-marigold family) Amaranthaceae (amaranth family) Ancistrocladaceae Asteropeiaceae Barbeuiaceae Basellaceae (basella family) Cactaceae (cactus family) Caryophyllaceae (carnation family) Dioncophyllaceae Droseraceae (sundew family) Drosophyllaceae Frankeniaceae Molluginaceae (carpetweed family) Nepenthaceae Nyctaginaceae (four-oclock family) Physenaceae Phytolaccaceae (pokeweed family) Plumbaginaceae (plumbago family) Polygonaceae (buckwheat family) Portulacaceae (purslane family) Rhabdodendraceae... This article is about the plant family. ... Species About 400 species; see text Galium is a large genus of annual and perennial herbaceous plants in the family Rubiaceae, with about 400 species occurring in the temperate zones of both the Northern and Southern Hemispheres. ... Nitrogen-based red pigment of beets (Beta spp. ...


Anatomically, anthocyanins are found mostly in flowers and fruits but also in leaves, stems, and roots. In these parts they are found predominantly in outer cell layers such as the epidermis and peripheral mesophyll cells. The amounts are relatively large: one kilogram of blackberry for example contains approximately 1.15 gram, and red and black legumes can contain 20 gram per 1 kg. Other plants rich in anthocyanins are chokeberry, cherry, eggplant, blue grape, Vaccinium and red cabbage and also the Usambara-violet. Anthocyanins are less abundant in banana, asparagus, pea, fennel, pear and potato. Most frequent in nature are the glycosides of cyanidin, delphinidin, malvidin, pelargonidin, peonidin and petunidin. Roughly 2% of all hydrocarbons fixated in photosynthesis are converted into flavonoids and their derivatives such as the anthocyanins. This is no less than 109 tons per year. Fruit stall in Barcelona, Spain. ... In the armed forces, leave is permission to be away from ones unit for a period of time. ... ROOT is an object-oriented software package developed by CERN. It was originally designed for particle physics data analysis and contains several features specific to this field, but it is also commonly used in other applications such as astronomy and data mining. ... The epidermis is the outer multi-layered group of cells covering the leaf and young tissues of a plant. ... The BlackBerry is a wireless handheld device introduced in 1999 which supports push e-mail, mobile telephone, text messaging, internet faxing, web browsing and other wireless information services. ... Varieties of soybean seeds, a popular legume Pea pods The term legume has two closely related meanings in botany, a situation encountered with many botanical common names of useful plants, whereby an applied name can refer to either the plant itself, or to the edible fruit (or useful part). ... Species Aronia arbutifolia (L.) Pers. ... Species Several, including: Prunus apetala Prunus avium (Wild/Sweet Cherry) Prunus campanulata Prunus canescens Prunus cerasus (Sour Cherry) Prunus concinna Prunus conradinae Prunus dielsiana Prunus emarginata (Bitter Cherry) Prunus fruticosa Prunus incisa Prunus litigiosa Prunus mahaleb (Saint Lucie Cherry) Prunus maximowiczii Prunus nipponica Prunus pensylvanica (Pin Cherry) Prunus pilosiuscula Prunus... Binomial name Solanum esculentum Drege ex Dun. ... Species Vitis acerifolia Vitis aestivalis Vitis amurensis Vitis arizonica Vitis x bourquina Vitis californica Vitis x champinii Vitis cinerea Vitis x doaniana Vitis girdiana Vitis labrusca Vitis x labruscana Vitis lincecumii Vitis monticola Vitis mustangensis Vitis x novae-angliae Vitis palmata Vitis riparia Vitis rotundifolia Vitis rupestris Vitis shuttleworthii Vitis... Species See text Vaccinium is a genus of shrubs in the plant Family Ericaceae including the cranberry, blueberry, lingonberry, bilberry, and huckleberry. ... Cultivar Group Brassica oleracea Capitata Group The Red Cabbage (Brassica oleracea var. ... Species List of Viola species Violets (Viola) are a genus of flowering plants in the family Violaceae, with around 400-500 species throughout the world, mainly in the temperate Northern Hemisphere but also in Hawaii, Australasia, and the Andes in South America. ... Species Hybrid origin; see text Banana is the common name used for herbaceous plants in the genus Musa, which because of their size and structure, are often mistaken for trees. ... Binomial name Asparagus officinalis L. Asparagus is a type of vegetable obtained from one species within the genus Asparagus, specifically the young shoots of Asparagus officinalis. ... Binomial name Pisum sativum L. A pea is the small, edible round green bean which grows in a pod on the leguminous vine Pisum sativum, or in some cases to the immature pods. ... Binomial name Foeniculum vulgare Mill. ... Species About 30 species; see text Pears are trees of the genus Pyrus and the juicy fruit of that tree, edible in some species. ... Binomial name Solanum tuberosum L. The potato (Solanum tuberosum) is a perennial plant of the Solanaceae, or nightshade, family, commonly grown for its starchy tuber. ... Chemical structure of cyanidin Cyanidin, or flavan-3-ol, is a natural organic compound which is classified as a flavonoid and an anthocyanin. ... Delphinidin Delphinidin is an anthocyanin, and a primary plant pigment. ... Malvidin is an anthocyanidin. ... Hydrocarbons are refined at oil refineries and processed at chemical plants In chemistry, a hydrocarbon is any chemical compound that consists only of the elements carbon (C) and hydrogen (H). ...

Juvenile anthocyanin in new rose growth. The reddish hue disappears as the new leaves mature.
Juvenile anthocyanin in new rose growth. The reddish hue disappears as the new leaves mature.

In plants anthocyanins are present together with other natural pigments like the closely chemically related flavonoids, carotenoids, anthoxanthins and betacyanins. Image File history File links Juvenile_anthocyanin. ... Image File history File links Juvenile_anthocyanin. ... Species Between 100 and 150, see list A rose is a flowering shrub of the genus Rosa, and the flower of this shrub. ... Molecular structure of flavone The term flavonoid refers to a class of plant secondary metabolites based around a phenylbenzopyrone structure. ... Carotenoids are organic pigments that are naturally occurring in plants and some other photosynthetic organisms like algae, some types of fungus and some bacteria. ... Nitrogen-based red pigment of beets (Beta spp. ...


In still relatively young plants or new growth, where chlorophyll and wax production has not yet begun and which would be unprotected from UV light, anthocyanin production increases. Parts or even the whole plant are colored by these "juvenile anthocyanins," and thereby protected from damage. As soon as chlorophyll production begins, the production of the anthocyanin dye is reduced. The build-up of anthocyanin in plants is specific to the plant type, since it depends on the soil conditions, light, warmth and plant type and/or sort. Plants that have only a single anthocyanin as pigment is extremely rare, but occurs nevertheless. The absence or particularly strong prevalence for a certain anthocyanin in a plant is due to genetic circumstances. Ultraviolet (UV) radiation is electromagnetic radiation of a wavelength shorter than that of the visible region, but longer than that of soft X-rays. ...


Structure

Benzopyrylium salts, Chloride as counterion
Benzopyrylium salts, Chloride as counterion

The pigment components of the anthocyanidins, the sugar-free anthocyanins, can be identified based on the structure of a large group of polymethine dye, as salt derivative of benzopyrylium (a cationic form of benzopyran, i.e an oxygen-containing heterocycle pyran fused to a benzene ring). The pyran ring in anthocyanin is connected to a phenyl group at the 2-position, which can carry different substituents. The counterion for the cationic oxygen in the pyran ring is mostly chloride. With this positive charge the anthocyanins differ from other flavonoids. The anthocyanins, anthocyanidins with sugar group, are mostly 3-glucosides of the anthocyanidins. In red wine, especially after maturation, many derivatives of the anthocyanins can be found. Image File history File links benzopyrydilium salts File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links benzopyrydilium salts File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... A magnified crystal of a salt (halite/sodium chloride) In chemistry, a salt is any ionic compound composed of positively charged cations and negatively charged anions so that the product is neutral and without a net charge. ... A cation is an ion with positive charge. ... Benzopyran is an polycyclic organic compound that results from the fusion of a benzene ring to a heterocyclic pyran ring. ... Heterocycles are organic chemical structures containing non-carbon elements. ... In chemistry, a pyran is a six member aromatic heterocyclic ring with five carbons and one oxygen. ... Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 Picture where the six carbon atoms are arranged in a cyclic manner. ... In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ... A counterion is the ion that accompanies an ionic species in order to maintain electric neutrality. ... A cation is an ion with positive charge. ... The chloride ion is formed when the element chlorine picks up one electron to form an anion (negatively-charged ion) Cl−. The salts of hydrochloric acid HCl contain chloride ions and are also called chlorides. ... A glucoside is a glycoside that is derived from glucose. ...


The anthocyanins are subdivided into the sugar-free anthocyanidine aglycons and the anthocyanin glycosides. They are considered secondary metabolites and allowed as a food additive with E number 163. As of 2003 more than 400 anthocyanins had been reported[1] while more recent literature (early 2006), puts the number at more than 550 different anthocyanins. The difference in chemical structure that occurs in response to changes in pH is the reason why anthocyanins are often used as pH indicator, as they change from red in acids to blue in bases. Magnification of typical sugar In non-scientific use, the term sugar means sucrose, also called table sugar or saccharose, a white crystalline solid disaccharide. ... Flavonoids are a group of chemical compounds naturally found in certain fruits, vegetables, teas, wines, nuts, seeds, and roots. ... A aglycon or aglycone is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom. ... Secondary metabolites are those chemical compounds in organisms that are not directly involved in the normal growth, development or reproduction of organisms. ... Food additives are substances added to food to preserve flavour or improve its taste and appearance. ... For the mathematical constant see: E (mathematical constant). ... pH is a measure of the acidity of a solution in terms of activity of hydrogen ions (H+). For dilute solutions, however, it is convenient to substitute the activity of the hydrogen ions with the molarity (mol/L) of the hydrogen ions (however, this is not necessarily accurate at higher... A pH indicator is a halochromic chemical compound that is added in small amounts to a solution so that the pH (acidity or alkalinity) of the solution can be determined easily. ... For other uses, see Acid (disambiguation). ... A bases in chemistry is a chemical substance which has a free pair of electrons to bind a Hydrogen ion commonly referred to as a proton (IUPAC definition). ...

Anthocyanin gives these pansies their dark purple pigmentation.
Anthocyanin gives these pansies their dark purple pigmentation.
Anthocyanin ground structure: the flavylium cation
Anthocyanin ground structure: the flavylium cation
Anthocyanidin R1 R2 R3 R4 R5 R6 R7
Aurantinidin -H -OH -H -OH -OH -OH -OH
Cyanidin -OH -OH -H -OH -OH -H -OH
Delphinidin -OH -OH -OH -OH -OH -H -OH
Europinidin -OCH3 -OH -OH -OH -OCH3 -H -OH
Luteolinidin -OH -OH -H -H -OH -H -OH
Pelargonidin -H -OH -H -OH -OH -H -OH
Malvidin -OCH3 -OH -OCH3 -OH -OH -H -OH
Peonidin -OCH3 -OH -H -OH -OH -H -OH
Petunidin -OH -OH -OCH3 -OH -OH -H -OH
Rosinidin -OCH3 -OH -H -OH -OH -H -OCH3

Image File history File linksMetadata Download high resolution version (3504x2336, 1493 KB) Summary Orange and violet pansies. ... Image File history File linksMetadata Download high resolution version (3504x2336, 1493 KB) Summary Orange and violet pansies. ... Binomial name Viola tricolor hortensis Viola * wittrockiana The Pansy or Pansy Violet is a cultivated garden flower. ... Image File history File links anthocyanins File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links anthocyanins File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Chemical structure of cyanidin Cyanidin, or flavan-3-ol, is a natural organic compound which is classified as a flavonoid and an anthocyanin. ... Delphinidin Delphinidin is an anthocyanin, and a primary plant pigment. ... Malvidin is an anthocyanidin. ...

Biosynthesis

Anthocyanin pigments are assembled from two different streams of chemical raw materials in the cell: both starting from the C2 unit acetate (or acetic acid) derived from photosynthesis, one stream involves the shikimic acid pathway to produce the amino acid phenylalanine. The other stream (the acetic acid pathway) produces 3 molecules of malonyl-Coenzyme A, a C3 unit. These streams meet and are coupled together by the enzyme chalcone synthase (CHS), which forms an intermediate chalcone via a polyketide folding mechanism that is commonly found in plants. The chalcone is subsequently isomerized by the enzyme chalcone isomerase (CHI) to the prototype pigment naringenin, which is subsequently oxidized by enzymes such as flavanone hydroxylase (FHT or F3H), flavonoid 3' hydroxylase and flavonoid 3' 5'-hydroxylase. These oxidation products are further reduced by the enzyme dihydroflavonol 4-reductase (DFR) to the corresponding leucoanthocyanidins. It was believed that leucoanthocyanidins are the immediate precursors of the next enzyme, a dioxygenase referred to as anthocyanidin synthase (ANS) or leucoanthocyanidin dioxygenase (LDOX). It was recently shown however that flavan-3-ols, the products of leucoanthocyanidin reductase (LAR), are the true substrates of ANS/LDOX. The resulting, unstable anthocyanidins are further coupled to sugar molecules by enzymes like UDP-3-O-glucosyl transferase to yield the final relatively stable anthocyanins. More than five enzymes are thus required to synthesize these pigments, each working in concert. Any even minor disruption in any of the mechanism of these enzymes by either genetic or environmental factors would halt anthocyanin production.


Autumn Leaf Color

Many science text books incorrectly state that all autumn coloration (including red) is simply the result of breakdown of green chlorophyll, which unmasks the already-present orange, yellow, and red pigments (carotenoids, xanthophylls, and anthocyanins, respectively). While this is indeed the case for the carotenoids and xanthophylls (orange and yellow pigments), anthocyanins are not present until the leaf begins breaking down the chlorophyll, during which time the plant begins to synthesize the anthocyanin, presumably for photoprotection during nitrogen translocation.


Recent research

In December 2004 a peer-reviewed study at Michigan State University published by the American Chemical Society noted that anthocyanin could boost insulin production by up to 50%. However the study leader noted that despite the initial excitement, more study would be needed. Also in 2005, an article published in Applied and Environmental Microbiology demonstrated for the first time the biosynthesis of anthocyanins in bacteria [1]. Michigan State University (MSU) is a public university in East Lansing, Michigan. ... The American Chemical Society (ACS) is a learned society (professional association) based in the United States that supports scientific inquiry in the field of chemistry. ... It has been suggested that Oral insulin be merged into this article or section. ...


References

  1. ^ http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=14561507&query_hl=4&itool=pubmed_DocSum
  1. Andersen, O.M. Flavonoids: Chemistry, Biochemistry and Applications. CRC Press, Boca Raton FL 2006.

External links


  Results from FactBites:
 
Spartanburg SC | GoUpstate.com | Spartanburg Herald-Journal (1796 words)
Anthocyanin pigments seem to help many pollinators to locate flowers that contain them, and in fruits, the colorful skins may be recognized by animals which will eat the fruits and disperse the seeds.
While this is indeed the case for the carotenoids and xanthophylls (orange and yellow pigments), anthocyanins are not present until the leaf begins breaking down the chlorophyll, during which time the plant begins to synthesize the anthocyanin, presumably for photoprotection during nitrogen translocation.
Anthocyanins are considered secondary metabolites and allowed as a food additive with E number 163.
Redox relationships in the development of anthocyanin (949 words)
The higher iodine absorption of anthocyanin bearing tissue may be seen to be localized in free plasmal lipids, in lipid material localized in "mitochondrial" or lipoclastic bodies in the cell, and in lipids impregnating cellulose walls.
In vitro preparations of anthocyanin extracts and unsaturated fat emulsions reveal that anthocyanin is a hydrogen acceptor and acts to dehydrogenate and oxidize the fat, and the anthocyanin becomes partially reduced and in some cases irreversibly reduced.
It is generally true that anthocyanin bearing cells are epidermal, hypodermal or bundle sheath cells which have an excess of lipid material, and it is a general rule that cells low in lipids are lacking in anthocyanin.
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