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30-AUGUST-2008 03:13:07 - Anthocyanin Redirected from Anthocyanins Anthocyanins are glucosides of anthocyanidins, the basic chemical structure of which is shown here. Anthocyanins are glucosides of anthocyanidins, the basic chemical structure of which is shown here. Anthocyanin gives these pansies their dark purple pigmentation. Anthocyanin gives these pansies their dark purple pigmentation. Not to be confused with Anthocyanidin, their sugar free counterparts. Anthocyanins from Greek: ἀνθός anthos = flower + κυανός kyanos = blue are water-soluble vacuolar pigments that may appear red, purple, or blue according to pH. They belong to a parent class of molecules called flavonoids synthesized via the phenylpropanoid pathway. Anthocyanins occur in all tissues of higher plants, including leaves, stems, roots, flowers, and fruits. Anthoxanthins are their clear, white to yellow counterparts occurring in plants. Contents 1 Function 2 Occurrence 3 Autumn leaf color 4 Structure 4.1 Anthocyanidins: Flavylium cation derivatives 4.2 Anthocyanins: Glucosides of anthocyanidins 5 Biosynthesis 6 Potential food value 7 Dye-sensitized solar cells 8 Research 9 References 10 External links Function Red color in Fuji apples Red color in Fuji apples Anthocyanin is the purple color of the vertical stripes on stem of this Jalapeño cultivar. Anthocyanin is the purple color of the vertical stripes on stem of this Jalapeño cultivar. In flowers, bright reds and purples are adaptive for attracting pollinators. In fruits, the colorful skins also attract the attention of animals, which may eat the fruits and disperse the seeds. In photosynthetic tissues such as leaves and sometimes stems, anthocyanins have been shown to act as a sunscreen, protecting cells from high-light damage by absorbing blue-green and UV 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 has also been proposed that red coloration of leaves may camouflage leaves from herbivores blind to red wavelengths, or signal unpalatability, since anthocyanin synthesis often coincides with synthesis of unpalatable phenolic compounds. In addition to their role as light-attenuators, anthocyanins also act as powerful antioxidants. However, it is not clear whether anthocyanins can significantly contribute to scavenging of free-radicals produced through metabolic processes in leaves, since they are located in the vacuole, and thus, spatially separated from metabolic reactive oxygen species. Occurrence 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. Food source Anthocyanin content in mg per 100 g açaà 320 blackcurrant 190-270 chokeberry 1,4801 eggplant 750 orange ~200 Marion blackberry 3172 black raspberry 5893 raspberry 365 wild blueberry 5584 cherry 350-400 redcurrant 80-420 red grape 8885 red wine 24-35 Anatomically, anthocyanins are found in the cell vacuole, 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. 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. There is no less than 109 tons of anthocyanins produced in nature per year.citation needed Not all land plants contain anthocyanin; in the Caryophyllales including cactus, beets, and amaranth, they are replaced by betalains. Plants rich in anthocyanins are Vaccinium species, such as blueberry, cranberry and bilberry, Rubus berries including black raspberry, red raspberry and blackberry, blackcurrant, cherry, eggplant peel, black rice, Concord grape and muscadine grape, red wine, red cabbage and violet petals. Anthocyanins are less abundant in banana, asparagus, pea, fennel, pear and potato, and may be totally absent in certain cultivars of green gooseberries.6 The highest recorded amount appears to be specifically in the seed coat of black soybean Glycine max L. Merr. containing some 2,000 mg per 100 g7 and in skins and pulp of black chokeberry Aronia melanocarpa L. table. However, the Amazonian palmberry, açaÃ, having about 320 mg per 100 g8 of which cyanidin-3-glucoside is the most prevalent individual anthocyanin approximately 10 mg per 100 g,9 is also a high-content source for which only a small fraction of total anthocyanins has been determined to date. Nature and food science have produced various uncommon crops containing anthocyanins, including blue- or red-fleshed potatoes and purple or red broccoli, cabbage, cauliflower, carrots and corn. Anthocyanins can also be found in naturally ripened olives, and are partly responsible for the purple color seen in Kalamata and Alfonso olives, although no studies to date have have quantified their amount. Autumn leaf color 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 Many science textbooks 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. Structure Anthocyanidins: Flavylium cation derivatives See Anthocyanidins article. Selected anthocyanidins and their substitutions Anthocyanidin Basic structure R1 R2 R3 R4 R5 R6 R7 Aurantinidin Basic structure of Anthocyans: The flavio-cation -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 Anthocyanins: Glucosides of anthocyanidins The anthocyanins, anthocyanidins with sugar group, are mostly 3-glucosides of the anthocyanidins. The anthocyanins are subdivided into the sugar-free anthocyanidin aglycones and the anthocyanin glycosides. As of 2003 more than 400 anthocyanins had been reported10 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. Biosynthesis Anthocyanins are responsible for the distinctive color of blood oranges, although carotenoids also contribute pigmentation in this fruit. Anthocyanins are responsible for the distinctive color of blood oranges, although carotenoids also contribute pigmentation in this fruit. Anthocyanin pigments are assembled like all other flavonoids from two different streams of chemical raw materials in the cell: One stream involves the shikimate pathway to produce the amino acid phenylalanine. see phenylpropanoids The other stream produces 3 molecules of malonyl-CoA, a C3 unit from a C2 unit acetyl-CoA. 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. Naringenin 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. Potential food value Anthocyanins are considered secondary metabolites as a food additive with E number 163. Anthocyanins are powerful antioxidants in vitro. This antioxidant property may be conserved even after the plant which produced the anthocyanin is consumed by another organism, possibly explaining why fruits and vegetables with colorful skins and pulp are considered nutritious. However, it has not yet been scientifically demonstrated that anthocyanins are beneficial to human health. Dye-sensitized solar cells Anthocyanins are being used in organic solar cells because of their ability to absorb light and convert it into electrons11. There are many benefits to using dye-sensitized solar cells instead of the traditional silicon cells, such as abundance of anthocyanins, the projected 90% efficiency, and the ability to bend or print these inks12. Research Richly concentrated as pigments in berries, anthocyanins were the topics of research presented at a 2007 symposium on health benefits that may result from berry consumption13. Scientists provided laboratory evidence for potential health effects against cancer aging and neurological diseases inflammation diabetes bacterial infections Cancer research on anthocyanins is the most advanced, where black raspberry Rubus occidentalis L. preparations were first used to inhibit chemically induced cancer of the rat esophagus by 30-60% and of the colon by up to 80%. Effective at both the initiation and promotion/progression stages of tumor development, black raspberries are a practical research tool and a promising therapeutic source, as they contain the richest contents of anthocyanins among native North American Rubus berries14. Work on laboratory cancer models has shown that black raspberry anthocyanins inhibit promotion and progression of tumor cells by stalling growth of pre-malignant cells accelerating the rate of cell turnover, called apoptosis, effectively making the cancer cells die faster reducing inflammatory mediators that initiate tumor onset inhibiting growth of new blood vessels that nourish tumors, a process called angiogenesis minimizing cancer-induced DNA damage. On a molecular level, berry anthocyanins were shown to turn off genes involved with proliferation, apoptosis, inflammation and angiogenesis.151617 In 2007, black raspberry studies entered the next pivotal level of research - the human clinical trial - for which several approved studies are underway to examine anti-cancer effects of black raspberries and cranberries on tumors in the esophagus, prostate and colon18. References ^ Wu X, Gu L, Prior RL, McKay S. Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity. J Agric Food Chem. 2004 Dec 29;5226:7846-56.1 ^ Siriwoharn T, Wrolstad RE, Finn CE, Pereira CB. Influence of cultivar, maturity, and sampling on blackberry Rubus L. Hybrids anthocyanins, polyphenolics, and antioxidant properties. J Agric Food Chem. 2004 Dec 29;5226:8021-30.2 ^ Wada L, Ou B. Antioxidant activity and phenolic content of Oregon caneberries. J Agric Food Chem. 2002 Jun 5;5012:3495-500.3 ^ Hosseinian FS, Beta T. Saskatoon and wild blueberries have higher anthocyanin contents than other Manitoba berries. J Agric Food Chem. 2007 Dec 26;5526:10832-8.4 ^ Muñoz-Espada AC, Wood KV, Bordelon B, Watkins BA. Anthocyanin quantification and radical scavenging capacity of Concord, Norton, and Marechal Foch grapes and wines. J Agric Food Chem. 2004 Nov 3;5222:6779-86.5 ^ Wu X, Gu L, Prior RL, McKay S. Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity. J Agric Food Chem. 2004 Dec 29;5226:7846-56.6 ^ Choung MG, Baek IY, Kang ST, Han WY, Shin DC, Moon HP, Kang KH. Isolation and determination of anthocyanins in seed coats of black soybean Glycine max L. Merr.. J Agric Food Chem. 2001 Dec;4912:5848-51.7 ^ Schauss AG, Wu X, Prior RL, Ou B, Patel D, Huang D, Kababick JP. Phytochemical and nutrient composition of the freeze-dried Amazonian palmberry, Euterpe oleraceae Mart. acai. J Agric Food Chem. 2006 Nov 1;5422:8598-603.8 ^ Del Pozo-Insfran D, Brenes CH, Talcott ST. Phytochemical composition and pigment stability of Açai Euterpe oleracea Mart.. J Agric Food Chem. 2004 Mar 24;526:1539-45.9 ^ Kong J. M., Chia L. S., Goh N. K., Chia T. F., Brouillard R. 2003. Analysis and biological activities of anthocyanins. Phytochemistry 64 5: 923-33. doi:10.1016/S0031-94220300438-2. ^ Nerine Cherepy, Greg Smestad, Michael Gratzel, Jen Zhang 1997. http://solideas.com/papers/JPhysChemB.pdf Ultrafast Electron Injection: Implications for a Photoelectrochemical Cell Utilizing an Anthocyanin Dye-Sensitized TiO2 Nanocrystalline Electrode. Journal of Physical Chemistry, Vol. 101, pp 9342-9351.. Retrieved on 2008-07-27. ^ Michael Gratzel 2003. Dye-sensitized solar cells. Journal of Photochemistry and Photobiology. Retrieved on 2008-07-27. ^ Gross PM 2007. Scientists zero in on health benefits of berry pigments. Natural Products Information Center. Retrieved on 2007-07-27. ^ Wada L, Ou B 2002. Antioxidant activity and phenolic content of Oregon caneberries.. J Agric Food Chem. Jun 5;5012:3495-500.. Retrieved on 2007-07-27. ^ Hou DX. Potential mechanisms of cancer chemoprevention by anthocyanins. Curr Mol Med. 2003 Mar;32:149-59. 10 ^ Karlsen A, Retterstøl L, Laake P, Paur I, Kjølsrud-Bøhn S, Sandvik L, Blomhoff R. Anthocyanins inhibit nuclear factor-kappaB activation in monocytes and reduce plasma concentrations of pro-inflammatory mediators in healthy adults. J Nutr. 2007 Aug;1378:1951-4.11 ^ Neto CC. Cranberry and blueberry: evidence for protective effects against cancer and vascular diseases. Mol Nutr Food Res. 2007 Jun;516:652-64.12 ^ Stoner GD, Wang LS, Zikri N, Chen T, Hecht SS, Huang C, Sardo C, Lechner JF 2007. Cancer prevention with freeze-dried berries and berry components.. 1: Semin Cancer Biol. May 10;. Retrieved on 2007-07-27. Andersen, O.M. Flavonoids: Chemistry, Biochemistry and Applications. CRC Press, Boca Raton FL 2006. G. M. Robinson, Robert Robinson 1931. A survey of anthocyanins. I. Biochem J. 25 5: 1687-1705. External links Anthocyanin biosynthesis Red leaves - why do Autumn leaves turn red? Super blackcurrants with boosted vitamin C Chemicals found in cherries may help fight diabetes A discussion of the role of anthocyanins in hydrangea coloration Anthocyanins FAQ MadSci Network v d e Types of Plant Pigments Flavonoids Anthocyanins Anthocyanidins Anthoxanthins Proanthocyanidins Tannins Betalains Betacyanins Betaxanthins Carotenoids Xanthophylls Carotenes Retinoids Other Chlorophyll Allophycocyanin Phycocyanin Phycoerythrin Phycoerythrocyanin Quinones Xanthones v d e Anthocyanins and their glucosides Anthocyanins cyanidin-3-rutinoside Protocyanin Anthocyanidins Cyanidin Delphinidin Europinidin Luteolinidin Pelargonidin Malvidin Peonidin Petunidin Rosinidin Retrieved from http://en..org/wiki/Anthocyanin Categories: Pigments | PH indicators | Bioindicators | Anthocyanins | OenologyHidden categories: All articles with statements | Articles with statements since May 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Alemannisch Català Dansk Deutsch Español Français Italiano עברית Magyar Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português РуÑ?Ñ?кий СрпÑ?ки / Srpski Suomi Svenska This page was last modified on 20 August 2008, at 11:27
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