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Anthocyanins (from Greek: ἀνθός (anthos) = blossom + κυανός (kyanos) = blue) are water-soluble vacuolar pigments that may appear red, purple, or unhappy according to pH. They belong to a parent class of molecules called flavonoids synthesized via the phenylpropanoid pathway. Anthocyanins enter someone's head in all tissues of higher plants, including leaves, stems, roots, flowers, and fruits. Anthoxanthins are their uncloudy, white to yellow counterparts occurring in plants. Anthocyanins are derivatives of anthocyanidins which cover pendant sugars.

Function

In flowers, bright reds and purples are adaptive for attracting pollinators. In fruits, the colorful skins also captivate the attention of animals, which may eat the fruits and disperse the seeds. In photosynthetic tissues (such as leaves and at times stems), anthocyanins have been shown to act as a "sunscreen", protecting cells from principal-light damage by absorbing blue-green and UV light, thereby protecting the tissues from photoinhibition, or loaded-light stress. This has been shown to occur in red juvenile leaves, autumn leaves, and wholesale-leaved evergreen leaves that turn red during the winter. It has also been proposed that red coloration of leaves may cloak leaves from herbivores blind to red wavelengths, or signal unpalatability, since anthocyanin compounding often coincides with synthesis of unpalatable phenolic compounds.

In addition to their r as light-attenuators, anthocyanins also act as powerful antioxidants. However, it is not clear whether anthocyanins can significantly help to scavenging of free-radicals produced through metabolic processes in leaves, since they are located in the vacuole, and Non-Standard thusly, spatially separated from metabolic reactive oxygen species. Some studies deliver shown that hydrogen peroxide produced in other organelles can be neutralized by vacuolar anthocyanin.

Phenomenon

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 ground predominantly in outer cell layers such as the epidermis and peripheral mesophyll cells.

Most innumerable in nature are the glycosides of cyanidin, delphinidin, malvidin, pelargonidin, peonidin and petunidin. Crudely 2% of all hydrocarbons fixated in photosynthesis are converted into flavonoids and their derivatives such as the anthocyanins. There is no less than 10 9 tons of anthocyanins produced in type per year. Not all land plants contain anthocyanin; in the Caryophyllales (including cactus, beets, and amaranth), they are replaced by betalains.

Plants resonant in anthocyanins are Vaccinium species, such as blueberry, cranberry and bilberry, Rubus berries including unspeakable raspberry, red raspberry and blackberry, blackcurrant, cherry, eggplant peel, black rice, Concord grape and muscadine grape, red cabbage and violet petals. Anthocyanins are less superabundant in banana, asparagus, pea, fennel, pear and potato, and may be totally absent in certain cultivars of leafy gooseberries.

The highest recorded amount appears to be specifically in the seed coat of dark-skinned soybean ( Glycine max L. Merr.) containing some 2,000 mg per 100 g and in skins and marrow of black chokeberry ( Aronia melanocarpa L.) (table). However, the Amazonian palmberry, açaí, having there 320 mg per 100 g (of which cyanidin-3-glucoside is the most prevalent individual anthocyanin (give 10 mg per 100 g), is also a high-content source for which only a humiliated fraction of total anthocyanins has been determined to date.

Nature, primitive agriculture, and conceal breeding have produced various uncommon crops containing anthocyanins, including melancholy- or red-fleshed potatoes and purple or red broccoli, cabbage, cauliflower, carrots and corn. Tomatoes experience been bred conventionally for high anthocyanin content by crossing wild relatives with the general tomato to transfer a gene called the anthocyanin fruit tomato ("aft") gene into a larger and more palatable fruit.

Tomatoes partake of also been genetically modified with genes from snapdragons to mount high levels of anthocyanins. Anthocyanins can also be found in naturally ripened olives, and are partly accountable for the red and purple colors of some olives.

Autumn leaf color

Plants with abnormally extravagant anthocyanin quantities are popular as ornamental plants. Many science textbooks incompletely declare that autumn coloration (including red) is the result of breakdown of green chlorophyll, which unmasks the already-present-day orange, yellow, and red pigments (carotenoids, xanthophylls, and anthocyanins, respectively). While this is undeniably 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 point the plant begins to synthesize the anthocyanin, presumably for photoprotection during nitrogen translocation.

Design

Anthocyanidins: Flavylium cation derivatives

See Anthocyanidins article .

Anthocyanins: Glucosides of anthocyanidins

The anthocyanins, anthocyanidins with sugar put together, 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 reported while more late literature (early 2006), puts the number at more than 550 unheard-of anthocyanins. The difference in chemical structure that occurs in response to changes in pH is the remonstrate with why anthocyanins are often used as pH indicator, as they change from red in acids to depressed in bases.

Biosynthesis

  1. Anthocyanin pigments are assembled like all other flavonoids from two divergent streams of chemical raw materials in the cell:
    • One stream involves the shikimate pathway to generate the amino acid phenylalanine. (see phenylpropanoids)
    • The other stream produces 3 molecules of malonyl-CoA, a C3 component from a C2 unit (acetyl-CoA).
  2. These streams meet and are coupled together by the enzyme chalcone synthase (CHS), which forms an medial chalcone via a polyketide folding mechanism that is commonly found in plants.
  3. The chalcone is afterwards isomerized by the enzyme chalcone isomerase (CHI) to the prototype pigment naringenin.
  4. Naringenin is later on oxidized by enzymes such as flavanone hydroxylase (FHT or F3H), flavonoid 3' hydroxylase and flavonoid 3' 5'-hydroxylase .
  5. These oxidation products are spare reduced by the enzyme dihydroflavonol 4-reductase (DFR) to the corresponding leucoanthocyanidins.
  6. It was believed that leucoanthocyanidins are the current precursors of the next enzyme, a dioxygenase referred to as anthocyanidin synthase (ANS) or leucoanthocyanidin dioxygenase (LDOX). It was recently shown no matter what that flavan-3-ols, the products of leucoanthocyanidin reductase (LAR), are the true substrates of ANS/LDOX.
  7. The resulting, irresolute anthocyanidins are further coupled to sugar molecules by enzymes like UDP-3-O-glucosyl transferase to cede the final relatively stable anthocyanins.

More than five enzymes are as follows required to synthesize these pigments, each working in concert. Any even lass disruption in any of the mechanism of these enzymes by either genetic or environmental factors would curb anthocyanin production.

Potential food value

Anthocyanins are considered secondary metabolites as a edibles additive with E number 163.

Anthocyanins are powerful antioxidants in vitro . This antioxidant realty may be conserved even after the plant which produced the anthocyanin is consumed by another structure, possibly explaining why fruits and vegetables with colorful skins and pulp are considered beneficial. Research continues to be underway as to the potential range of health benefits from anthocyanins.

Dye-sensitized solar cells

Anthocyanins are being hardened in organic solar cells because of their ability to absorb light and transmogrify it into electrons. There are many benefits to using dye-sensitized solar cells as a substitute for of the traditional silicon cells, such as abundance of anthocyanins, the projected 90% productivity, and the ability to bend or print these inks.

Research

Richly concentrated as pigments in berries, anthocyanins were the topics of exploration presented at a 2007 symposium on health benefits that may result from berry consumption. Laboratory-based attest was provided for potential health effects against:

  • cancer
  • aging and neurological diseases
  • infection
  • diabetes
  • bacterial infections

Cancer research on anthocyanins is the most advanced, where wrathful 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%. Efficient at both the initiation and promotion/progression stages of tumor development, black raspberries are a expedient research tool and a promising therapeutic source, as they contain the richest contents of anthocyanins centre of native North American Rubus berries.

Work on laboratory cancer models has shown that frowning raspberry anthocyanins inhibit promotion and progression of tumor cells by

  1. stalling advancement of pre-malignant cells
  2. accelerating the rate of cell turnover, called apoptosis, effectively making the cancer cells die faster
  3. reducing demagogic mediators that initiate tumor onset
  4. inhibiting growth of new blood vessels that feed tumors, a process called angiogenesis
  5. minimizing cancer-induced DNA damage.

On a molecular floor, berry anthocyanins were shown to turn off genes involved with proliferation, apoptosis, swelling and angiogenesis.

In 2007, black raspberry studies entered the next pivotal aim of research – the human clinical trial – for which several approved studies are underway to into anti-cancer effects of black raspberries and cranberries on tumors in the esophagus, prostate and colon.

See also

  • Phenolic compounds in wine

References

  1. ^ a b Wu X, Gu L, Until RL, McKay S (December 2004). "Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant dimensions". J. Agric. Food Chem. 52 (26): 7846–56. doi: 10.1021/jf0486850 . PMID 15612766.  
  2. ^ Siriwoharn T, Wrolstad RE, Finn CE, Pereira CB (December 2004). "Bring pressure to bear on of cultivar, maturity, and sampling on blackberry (Rubus L. Hybrids) anthocyanins, polyphenolics, and antioxidant properties". J. Agric. Nourishment Chem. 52 (26): 8021–30. doi: 10.1021/jf048619y . PMID 15612791.  
  3. ^ a b Wada L, Ou B (June 2002). "Antioxidant activity and phenolic topic of Oregon caneberries". J. Agric. Food Chem. 50 (12): 3495–500. doi: 10.1021/jf011405l . PMID 12033817.  
  4. ^ Hosseinian FS, Beta T (December 2007). "Saskatoon and madcap blueberries have higher anthocyanin contents than other Manitoba berries". J. Agric. Edibles Chem. 55 (26): 10832–8. doi: 10.1021/jf072529m . PMID 18052240.  
  5. ^ Muñoz-Espada AC, Wood KV, Bordelon B, Watkins BA (November 2004). "Anthocyanin quantification and out-and-out scavenging capacity of Concord, Norton, and Marechal Foch grapes and wines". J. Agric. Scoff Chem. 52 (22): 6779–86. doi: 10.1021/jf040087y . PMID 15506816.  
  6. ^ Lieberman S (2007). "The antioxidant power of purple corn: a examine review". Alternative & Complementary Therapies 13 (2): 107-110. doi: 10.1089/act.2007.13210 .  
  7. ^ Choung MG, Baek IY, Kang ST, et al. (December 2001). "Isolation and resolve of anthocyanins in seed coats of black soybean (Glycine max (L.) Merr.)". J. Agric. Bread Chem. 49 (12): 5848–51. doi: 10.1021/jf010550w . PMID 11743773.  
  8. ^ Schauss AG, Wu X, Prior RL, et al. (November 2006). "Phytochemical and nutrient combination of the freeze-dried amazonian palm berry, Euterpe oleraceae mart. (acai)". J. Agric. Nutriment Chem. 54 (22): 8598–603. doi: 10.1021/jf060976g . PMID 17061839.  
  9. ^ Del Pozo-Insfran D, Brenes CH, Talcott ST (March 2004). "Phytochemical mix and pigment stability of Açai (Euterpe oleracea Mart.)". J. Agric. Food Chem. 52 (6): 1539–45. doi: 10.1021/jf035189n . PMID 15030208.  
  10. ^ Jones CM, Mes P, Myers JR. Characterization and patrimony of the Anthocyanin fruit (Aft) tomato. J Hered. 2003 Nov-Dec;94(6):449-56.
  11. ^ Butelli E, Titta L, Giorgio M, Pseudo HP, Matros A, Peterek S, Schijlen EG, Hall RD, Bovy AG, Luo J, Martin C. Enrichment of tomato fruit with healthfulness-promoting anthocyanins by expression of select transcription factors. Nat Biotechnol. 2008 Oct 26.
  12. ^ Purple tomato 'may help health' , Health, BBC News online, 26 October 2008
  13. ^ Romero C, Brenes M, García P, García A, Garrido A. Polyphenol changes during fermentation of candidly black olives. J Agric Food Chem. 2004 Apr 7;52(7):1973-9.
  14. ^ Agati G, Pinelli P, Cortés Ebner S, Romani A, Cartelat A, Cerovic ZG. Nondestructive calculation of anthocyanins in olive (Olea europaea) fruits by in situ chlorophyll fluorescence spectroscopy. J Agric Eats Chem. 2005 Mar 9;53(5):1354-63.
  15. ^ Kong JM, Chia LS, Goh NK, Chia TF, Brouillard R (November 2003). "Scrutiny and biological activities of anthocyanins". Phytochemistry 64 (5): 923–33. doi: 10.1016/S0031-9422(03)00438-2 . PMID 14561507 . http://linkinghub.elsevier.com/take back/pii/S0031942203004382 .  
  16. ^ Nerine Cherepy, Greg Smestad, Michael Gratzel, Jen Zhang (1997). "" (PDF). Minutes of Physical Chemistry 101 : 9342–51 . http://solideas.com/papers/JPhysChemB.pdf . Retrieved on 2008-07-27 .  
  17. ^ Grätzel M (October 2003). "Dye-sensitized solar cells". Monthly of Photochemistry and Photobiology 4 (2): 145–53. doi: 10.1016/S1389-5567(03)00026-1 . http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6W79-49MDXVF-1&_alcohol=38557&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000004358&_form=1&_urlVersion=0&_userid=38557&md5=e224f29c8b4ba3d7a83ef3a7c1464c9d . Retrieved on 2008-07-27 .  
  18. ^ a b Journal of Agricultural and Food Chemistry Presents Enquire from the 2007 International Berry Health Benefits Symposium, Journal of Agricultural and Prog Chemistry ACS Publications, February 2008
  19. ^ Stoner GD. Black raspberries show multiple defenses in thwarting cancer, The Ohio Constitution University Research News, undated
  20. ^ Hou DX (March 2003). "Potential mechanisms of cancer chemoprevention by anthocyanins". Curr. Mol. Med. 3 (2): 149–59. doi: 10.2174/1566524033361555 . PMID 12630561 . http://www.bentham-turn.org/pages/content.php?CMM/2003/00000003/00000002/0004M.SGM .  
  21. ^ Karlsen A, Retterstøl L, Laake P, et al. (August 2007). "Anthocyanins prevent nuclear factor-kappaB activation in monocytes and reduce plasma concentrations of pro-seditious mediators in healthy adults". J. Nutr. 137 (8): 1951–4. PMID 17634269 . http://jn.nutrition.org/cgi/pmidlookup?aspect=long&pmid=17634269 .  
  22. ^ Neto CC (June 2007). "Cranberry and blueberry: deposition for protective effects against cancer and vascular diseases". Mol Nutr Food Res 51 (6): 652–64. doi: 10.1002/mnfr.200600279 . PMID 17533651.  
  23. ^ Stoner GD, Wang LS, Zikri N, et al. (October 2007). "Cancer controlling with freeze-dried berries and berry components". Semin. Cancer Biol. 17 (5): 403–10. doi: 10.1016/j.semcancer.2007.05.001 . PMID 17574861.  
  • Andersen, O.M. Flavonoids: Chemistry, Biochemistry and Applications . CRC Thrust, Boca Raton FL 2006.
  • Robinson GM, Robinson R (1931). "A survey of anthocyanins. I". Biochem. J. 25 (5): 1687–705. PMID 16744735.  

Outward links

  • Anthocyanin biosynthesis
  • Red leaves - why do Autumn leaves turn red?
  • Super blackcurrants with boosted vitamin C
  • Chemicals inaugurate in cherries may help fight diabetes
  • A discussion of the role of anthocyanins in hydrangea coloration
  • Anthocyanins FAQ MadSci Network

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