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14-September-2008 18:38:41 - Betalain Redirected from Betacyanins The red color of beets comes from betalain pigments. The red color of beets comes from betalain pigments. Betalains are a class of red and yellow indole-derived pigments found in plants of the Caryophyllales. They are most often noticeable in the petals of flowers, but may color the fruits, leaves, stems, and roots of plants that contain them. Contents 1 Description 2 Chemistry 3 Taxonomic significance 4 Economic uses 5 See also 6 References 7 External links Description Swiss chard, showing one plant expressing yellow betaxanthins and another expressing red betacyanins. Swiss chard, showing one plant expressing yellow betaxanthins and another expressing red betacyanins. The name betalain comes from the Latin name of the common beet Beta vulgaris, from which betalains were first extracted. The deep red color of beets, bougainvillea, amaranth, and many cacti results from the presence of betalain pigments.1 The particular shades of red to purple are distinctive and unlike that of anthocyanin pigments found in most plants. Betalains may occur in any part of the plant, including the petals of flowers, fruits, leaves, stems, and roots. There are two categories of betalains:2 Betacyanins include the reddish to violet betalain pigments. Betaxanthins are those betalain pigments which appear yellow to orange. Among the betaxanthins present in plants include vulgaxanthin, miraxanthin and portulaxanthin, and indicaxanthin. Plant physiologists are uncertain of the function that betalains serve in those plants which possess them, but there is some preliminary evidence that they may have fungicidal properties.3 Chemistry Chemical structure of betanin. Chemical structure of betanin. It was once thought that betalains were related to anthocyanins, the reddish pigments found in most plants. Both betalains and anthocyanins are water-soluble pigments found in the vacuoles of plant cells. However, betalains are structurally and chemically unlike anthocyanins. For example, betalains contain nitrogen whereas anthocyanins do not.1 It is now known that betalains are aromatic indole derivatives synthesized from tyrosine. They are not related chemically to the anthocyanins and are not even flavonoids.4 Each betalain is a glycoside, and consists of a sugar and a colored portion. Their synthesis is promoted by light.2 The most heavily studied betalain is betanin, also called beetroot red after the fact that it may be extracted from red beet roots. Betanin is a glucoside, and hydrolyzes into the sugar glucose and betanidin.1 It is used as a food coloring agent, and the color is sensitive to pH. Other betalains known to occur in beets are isobetanin, probetanin, and neobetanin. Other important betacyanins are amaranthine and isoamaranthine, isolated from species of Amaranthus. Taxonomic significance Flowers of the cactus Mammillaria sp. contain betalains. Flowers of the cactus Mammillaria sp. contain betalains. Betalain pigments occur only in the Caryophyllales and some Basidiomycota mushrooms.5 Where they occur in plants, they sometimes coexist with anthoxanthins yellow to orange flavonoids, but never occur in plant species with anthocyanins. Among the flowering plant order Caryophyllales, most members produce betalains and lack anthocyanins. Of all the families in the Caryophyllales, only the Caryophyllaceae carnation family and Molluginaceae produce anthocyanins instead of betalains.5 The limited distribution of betalains among plants is a synapomorphy for the Caryophyllales, though their production has been lost in two families. Recently, betalain-like compounds have been discovered in carnivorous plants that were not previously considered related to the Caryophyllales, but which have been added to that order under the APG II system. Betalains are now known from species of Drosera sundew and Nepenthes.citation needed Economic uses Inflorescences of Amaranthus caudatus love-lies-bleeding contain large quantities of betacyanins. Inflorescences of Amaranthus caudatus love-lies-bleeding contain large quantities of betacyanins. Betanin is commercially used as a natural food dye. It can cause beeturia red urine and faeces in some people who are unable to break it down. The interest of the food industry in betalains has grown since they were identified as natural antioxidants6 which may have positive health effects in humans.7 Betalians may exhibit anti-cancer activity. Betalains from the prickly pear showed considerable free radical scavenger and antioxidant properties in vitro to protect endothelium from cytokine-induced redox state alteration, through ICAM-1 inhibition.8 The 'Hopi Red Dye' amaranth produces red flowers which the Hopi Amerindians used as the source of a deep red dye. See also Biological pigment Caryophyllales Glycoside References ^ a b c Robinson, Trevor 1963. The Organic Constituents of Higher Plants. Minneapolis: Burgess Publishing, 292. ^ a b Salisbury, Frank B.; Cleon W. Ross 1991. Plant Physiology, 4th, Belmont, California: Wadsworth Publishing, 325-326. ISBN 0-534-15162-0. ^ Kimler, L. M. 1975. Betanin, the red beet pigment, as an antifungal agent. Botanical Society of America, Abstracts of papers 36. ^ Raven, Peter H.; Ray F. Evert, Susan E. Eichhorn 2004. Biology of Plants, 7th, New York: W. H. Freeman and Company, 465. ISBN 0-7167-1007-2. ^ a b Cronquist, Arthur 1981. An Integrated System of Classification of Flowering Plants. New York: Columbia University Press, 235-239. ISBN 0-231-03880-1. ^ Escribano, J.; M. A. Pedreño, F. García-Carmona, R. Muñoz 1998. Characterization of the antiradical activity of betalains from Beta vulgaris L. roots. Phytochem. Anal. 9: 124-127. doi:10.1002/SICI1099-1565199805/069:3124::AID-PCA4013.0.CO;2-0. ^ Tesoriere, Luisa; Mario Allegra, Daniela Butera, and Maria A. Livrea 2004. Absorption, excretion, and distribution of dietary antioxidant betalains in LDLs: potential health effects of betalains in humans. American Journal of Clinical Nutrition 80 4: 941-945. PMID 15447903. ^ Antioxidant betalains from cactus pear Opuntia ficus-indica inhibit endothelial ICAM-1 expression. My paper C Gentile, L Tesoriere, M Allegra, M A Livrea, P D'Alessio Dipartimento Farmacochimico, Tossicologico e Biologico, Università di Palermo, Italy. Bougainvillea bracts get their color from betalains Bougainvillea bracts get their color from betalains External links Look up Betalain in Wiktionary, the free dictionary. Betalain synthesis diagram 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 Glycosides Bond: N-glycosidic bond | O-glycosidic bond | S-glycosidic bond Geometry: α-Glycoside | β-Glycoside | 1,4-Glycoside | 1,6-Glycoside Glycone: Glucoside | Fructoside | Glucuronide Aglycone: Alcoholic glycoside | Anthraquinone glycoside | Bufanolide | Cardenolide | Cardiac glycoside | Coumarin glycoside | Cyanogenic glycoside | Flavonoid glycoside | Glycosylamine | Phenolic glycoside | Saponin | Steviol glycoside | Thioglycoside Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Betalain Categories: Pigments | Glycosides | Natural dyes | Food antioxidantsHidden categories: All articles with statements | Articles with statements since September 2007 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 Deutsch Français This page was last modified on 5 July 2008, at 05:22
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