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14-September-2008 18:38:37 - Carotenoid Redirected from Carotenoids June 2008 The orange ring surrounding Grand Prismatic Spring is due to carotenoid molecules, produced by huge mats of algae and bacteria. The orange ring surrounding Grand Prismatic Spring is due to carotenoid molecules, produced by huge mats of algae and bacteria. Carotenoids are organic pigments that are naturally occurring in chromoplasts of plants and some other photosynthetic organisms like algae, some types of fungus and some bacteria. There are over 600 known carotenoids; they are split into two classes, xanthophylls and carotenes. They absorb blue light. Carotenoids serve two key roles in plants and algae: they absorb light energy for use in photosynthesis, and they protect chlorophyll from photodamage.1 In humans, carotenoids such as beta-carotene are a precursor to vitamin A, a pigment essential for good vision, and carotenoids can also act as antioxidants. People consuming diets rich in carotenoids from natural foods, such as fruits and vegetables, are healthier and have lower mortality from a number of chronic illnesses.citation needed However, a recent meta-analysis of 68 reliable antioxidant supplementation experiments involving a total of 232,606 individuals concluded that consuming additional beta-carotene from supplements is unlikely to be beneficial and may actually be harmful,2 although this conclusion may be due to the inclusion of studies involving smokers.3 Since most carotenoid-rich fruits and vegetables are low in lipids and since dietary lipids have been hypothesized to be an important factor for carotenoid bioavailability, a 2005 study investigated whether addition of avocado fruit or oil, as lipid sources, would enhance carotenoid absorption in humans. The study found that the addition of both avocado fruit and oil significantly enhanced the subjects' absorption of all carotenoids tested alpha-carotene, beta-carotene, lycopene, and lutein.4 Contents 1 Properties 2 Physiological effects 3 Aroma chemicals 4 Disease 5 List of Naturally occurring carotenoids 6 References 7 Classifications 8 See also 9 External links Properties Carotenoids belong to the category of tetraterpenoids i.e. they contain 40 carbon atoms. Structurally they are in the form of a polyene chain which is sometimes terminated by rings. Carotenoids with molecules containing oxygen, such as lutein and zeaxanthin, are known as xanthophylls. The unoxygenated oxygen free carotenoids such as alpha-carotene, beta-carotene and lycopene are known as carotenes. Carotenes typically contain only carbon and hydrogen. Probably the most well-known carotenoid is the one that gives this second group its name, carotene, found in carrots also apricots and responsible for their bright orange colour. Crude palm oil, however, is the richest source of carotenoids in nature5. Their colour, ranging from pale yellow through bright orange to deep red, is directly linked to their structure. Xanthophylls are often yellow, hence their class name. The double carbon-carbon bonds interact with each other in a process called conjugation, which allows electrons in the molecule to move freely across these areas of the molecule. As the number of double bonds increases, electrons associated with conjugated systems have more room to move, and require less energy to change states. This causes the range of energies of light absorbed by the molecule to decrease. As more frequencies of light are absorbed from the short end of the visible spectrum, the compounds acquire an increasingly red appearance.citation needed Physiological effects In photosynthetic organisms, carotenoids play a vital role in the photosynthetic reaction centre. They either participate in the energy-transfer process, or protect the reaction center from auto-oxidation. In non-photosynthesizing organisms, carotenoids have been linked to oxidation-preventing mechanisms. Carotenoids disposition in proteins. Left: in cyanobacterium photosystem I carotenoids are outside orange PDB 1jb0. Right: in rhodopsin retinal is deep inside pink PDB 1f88. Carotenoids disposition in proteins. Left: in cyanobacterium photosystem I carotenoids are outside orange PDB 1jb0. Right: in rhodopsin retinal is deep inside pink PDB 1f88. Carotenoids have many physiological functions. Given their structure above, carotenoids are efficient free-radical scavengers, and they enhance the vertebrate immune system. Consequently, epidemiological studies have shown that people with high beta-carotene intake and high plasma levels of beta-carotene have a significantly reduced risk of lung cancer. However, studies of supplementation with large doses of beta-carotene in smokers have shown an increase in cancer risk possibly because excessive beta-carotene results in breakdown products that reduce plasma vitamin A and worsen the lung cell proliferation induced by smoke6. Similar results have been found in other animals. Not all carotenoids are helpful, e.g. etretinate is a teratogen. Animals are incapable of synthesizing carotenoids, and must obtain them through their diet, yet they are common and often in ornamental features. For example, the pink colour of flamingos and salmon, and the red colouring of lobsters are due to carotenoids. It has been proposed that carotenoids are used in ornamental traits because, given their physiological and chemical properties, they can be used as honest indicators of individual health, and hence they can be used by animals when selecting potential mates. Simplified carotenoid synthesis pathway. Simplified carotenoid synthesis pathway. The most common carotenoids include lycopene and the vitamin A precursor β-carotene. In plants, the xanthophyll lutein is the most abundant carotenoid and its role in preventing age-related eye disease is currently under investigation. Lutein and the other carotenoid pigments found in leaves are not obvious because of the presence of other pigments such as chlorophyll. Aroma chemicals Products of carotenoid degradation such as ionones, damascones, and damascenones are also important fragrance chemicals that are used extensively in the perfumes and fragrance industry. Both beta-damascenone and beta-ionone although low in concentration in rose distillates are the key odour-contributing compounds in flowers. In fact, the sweet floral smells present in black tea, aged tobacco, grape, and many fruits are due to the aromatic compounds resulting from carotenoid breakdown. Disease Despite being important in nutrition, some carotenoids are produced by bacteria to protect themselves from immune attack, such as MRSA. The golden pigment of S. aureus allows it to survive competitive attack by Lactobaccillus as well as the human immune system.7 List of Naturally occurring carotenoids Hydrocarbons Lycopersene 7,8,11,12,15,7',8',11',12',15'-Decahydro-y,y-carotene Phytofluene Hexahydrolycopene 15-cis-7,8,11,12,7',8'-Hexahydro-y,y-carotene Torulene 3',4'-Didehydro-b,y-carotene a-Zeacarotene 7',8'-Dihydro-e,y-carotene Alcohols Alloxanthin Cynthiaxanthin Pectenoxanthin Cryptomonaxanthin 3R,3'R-7,8,7',8'-Tetradehydro-b,b-carotene-3,3'-diol Crustaxanthin b,b-Carotene-3,4,3',4'-tetrol Gazaniaxanthin 3R-5'-cis-b,y-Caroten-3-ol OH-Chlorobactene 1',2'-Dihydro-f,y-caroten-1'-ol Loroxanthin b,e-Carotene-3,19,3'-triol Lycoxanthin y,y-Caroten-16-ol Rhodopin 1,2-Dihydro-y,y-caroten-l-ol Rhodopinol aka Warmingol 13-cis-1,2-Dihydro-y,y-carotene-1,20-diol Saproxanthin 3',4'-Didehydro-1',2'-dihydro-b,y-carotene-3,1'-diol Glycosides Oscillaxanthin 2,2'-Bisb-L-rhamnopyranosyloxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-1,1'-diol Phleixanthophyll 1'-b-D-Glucopyranosyloxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-2'-ol Ethers Rhodovibrin 1'-Methoxy-3',4'-didehydro-1,2,1',2'-tetrahydro-y,y-caroten-1-ol Spheroidene 1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-y,y-carotene Epoxides Diadinoxanthin 5,6-Epoxy-7',8'-didehydro-5,6-dihydro--carotene-3,3-diol Luteoxanthin 5,6: 5',8'-Diepoxy-5,6,5',8'-tetrahydro-b,b-carotene-3,3'-diol Mutatoxanthin Citroxanthin Zeaxanthin furanoxide 5,8-Epoxy-5,8-dihydro-b,b-carotene-3,3'-diol Neochrome 5',8'-Epoxy-6,7-didehydro-5,6,5',8'-tetrahydro-b,b-carotene-3,5,3'-triol Foliachrome Trollichrome Vaucheriaxanthin 5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-b,b-carotene-3,5,19,3'-tetrol Aldehydes Rhodopinal Wamingone 13-cis-1-Hydroxy-1,2-dihydro-y,y-caroten-20-al Torularhodinaldehyde 3',4'-Didehydro-b,y-caroten-16'-al Acids and Acid Esters Torularhodin 3',4'-Didehydro-b,y-caroten-16'-oic acid Torularhodin methyl ester Methyl 3',4'-didehydro-b,y-caroten-16'-oate Ketones Canthaxanthin aka Aphanicin, Chlorellaxanthin b,b-Carotene-4,4'-dione Capsanthin 3R,3'S,5'R-3,3'-Dihydroxy-b,k-caroten-6'-one Capsorubin 3S,5R,3'S,5'R-3,3'-Dihydroxy-k,k-carotene-6,6'-dione Cryptocapsin 3'R,5'R-3'-Hydroxy-b,k-caroten-6'-one 2,2'-Diketospirilloxanthin 1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-2,2'-dione Flexixanthin 3,1'-Dihydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-4-one 3-OH-Canthaxanthin aka Adonirubin aka Phoenicoxanthin 3-Hydroxy-b,b-carotene-4,4'-dione Hydroxyspheriodenone 1'-Hydroxy-1-methoxy-3,4-didehydro-1,2,1',2',7',8'-hexahydro-y,y-caroten-2-one Okenone 1'-Methoxy-1',2'-dihydro-c,y-caroten-4'-one Pectenolone 3,3'-Dihydroxy-7',8'-didehydro-b,b-caroten-4-one Phoeniconone aka Dehydroadonirubin 3-Hydroxy-2,3-didehydro-b,b-carotene-4,4'-dione Phoenicopterone b,e-caroten-4-one Rubixanthone 3-Hydroxy-b,y-caroten-4'-one Siphonaxanthin 3,19,3'-Trihydroxy-7,8-dihydro-b,e-caroten-8-one Esters of Alcohols Astacein 3,3'-Bispalmitoyloxy-2,3,2',3'-tetradehydro-b,b-carotene-4,4'-dione or 3,3'-dihydroxy-2,3,2',3'-tetradehydro-b,b-carotene-4,4'-dione dipalmitate Fucoxanthin 3'-Acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-b,b-caroten-8-one Isofucoxanthin 3'-Acetoxy-3,5,5'-trihydroxy-6',7'-didehydro-5,8,5',6'-tetrahydro-b,b-caroten-8-one Physalien Zeaxanthin dipalmitate 3R,3'R-3,3'-Bispalmitoyloxy-b,b-carotene or 3R,3'R-b,b-carotene-3,3'-diol dipalmitate Siphonein 3,3'-Dihydroxy-19-lauroyloxy-7,8-dihydro-b,e-caroten-8-one or 3,19,3'-trihydroxy-7,8-dihydro-b,e-caroten-8-one 19-laurate Apo Carotenoids b-Apo-2'-carotenal 3',4'-Didehydro-2'-apo-b-caroten-2'-al Apo-2-lycopenal Apo-6'-lycopenal 6'-Apo-y-caroten-6'-al Azafrinaldehyde 5,6-Dihydroxy-5,6-dihydro-10'-apo-b-caroten-10'-al Bixin 6'-Methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioate Citranaxanthin 5',6'-Dihydro-5'-apo-b-caroten-6'-one or 5',6'-dihydro-5'-apo-18'-nor-b-caroten-6'-one or 6'-methyl-6'-apo-b-caroten-6'-one Crocetin 8,8'-Diapo-8,8'-carotenedioic acid Crocetinsemialdehyde 8'-Oxo-8,8'-diapo-8-carotenoic acid Crocin Digentiobiosyl 8,8'-diapo-8,8'-carotenedioate Hopkinsiaxanthin 3-Hydroxy-7,8-didehydro-7',8'-dihydro-7'-apo-b-carotene-4,8'-dione or 3-hydroxy-8'-methyl-7,8-didehydro-8'-apo-b-carotene-4,8'-dione Methyl apo-6'-lycopenoate Methyl 6'-apo-y-caroten-6'-oate Paracentrone 3,5-Dihydroxy-6,7-didehydro-5,6,7',8'-tetrahydro-7'-apo-b-caroten-8'-one or 3,5-dihydroxy-8'-methyl-6,7-didehydro-5,6-dihydro-8'-apo-b-caroten-8'-one Sintaxanthin 7',8'-Dihydro-7'-apo-b-caroten-8'-one or 8'-methyl-8'-apo-b-caroten-8'-one Nor and Seco Carotenoids Actinioerythrin 3,3'-Bisacyloxy-2,2'-dinor-b,b-carotene-4,4'-dione b-Carotenone 5,6:5',6'-Diseco-b,b-carotene-5,6,5',6'-tetrone Peridinin 3'-Acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,5',6'-tetrahydro-12',13',20'-trinor-b,b-caroten-19,11-olide Pyrrhoxanthininol 5,6-epoxy-3,3'-dihydroxy-7',8'-didehydro-5,6-dihydro-12',13',20'-trinor-b,b-caroten-19,11-olide Semi-a-carotenone 5,6-Seco-b,e-carotene-5,6-dione Semi-b-carotenone 5,6-seco-b,b-carotene-5,6-dione or 5',6'-seco-b,b-carotene-5',6'-dione Triphasiaxanthin 3-Hydroxysemi-b-carotenone 3'-Hydroxy-5,6-seco-b,b-carotene-5,6-dione or 3-hydroxy-5',6'-seco-b,b-carotene-5',6'-dione retro Carotenoids and retro Apo Carotenoids Eschscholtzxanthin 4',5'-Didehydro-4,5'-retro-b,b-carotene-3,3'-diol Eschscholtzxanthone 3'-Hydroxy-4',5'-didehydro-4,5'-retro-b,b-caroten-3-one Rhodoxanthin 4',5'-Didehydro-4,5'-retro-b,b-carotene-3,3'-dione Tangeraxanthin 3-Hydroxy-5'-methyl-4,5'-retro-5'-apo-b-caroten-5'-one or 3-hydroxy-4,5'-retro-5'-apo-b-caroten-5'-one Higher Carotenoids Nonaprenoxanthin 2-4-Hydroxy-3-methyl-2-butenyl-7',8',11',12'-tetrahydro-e,y-carotene Decaprenoxanthin 2,2'-Bis4-hydroxy-3-methyl-2-butenyl-e,e-carotene C.p. 450 2-4-Hydroxy-3-hydroxymethyl-2-butenyl-2'-3-methyl-2-butenyl-b,b-carotene C.p. 473 2'-4-Hydroxy-3-methyl-2-butenyl-2-3-methyl-2-butenyl-3',4'-didehydro-l',2'-dihydro-b,y-caroten-1'-ol Bacterioruberin 2,2'-Bis3-hydroxy-3-methylbutyl-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-1,1'-dio References ^ Armstrong GA, Hearst JE 1996. Carotenoids 2: Genetics and molecular biology of carotenoid pigment biosynthesis. FASEB J. 10 2: 228-37. PMID 8641556. ^ Bjelakovic G, et al 2007. Mortality in randomized trials of antioxidant supplements for primary and secondary prevention: systematic review and meta-analysis. JAMA 297 8: 842-57. doi:10.1001/jama.297.8.842. PMID 17327526. ^ It is known that taking beta-carotene supplements is harmful for smokers, and the meta-analysis of Bjelakovic et al. was influenced by inclusion of these studies. See the letter to JAMA by Philip Taylor and Sanford Dawsey and the reply by the authors of the original paper. ^ Unlu N, et al 2005. Carotenoid Absorption from Salad and Salsa by Humans Is Enhanced by the Addition of Avocado or Avocado Oil. Human Nutrition and Metabolism 135 3: 431-6. PMID 15735074. ^ Choo Yuen May Palm oil carotenoids ^ Alija AJ, Bresgen N, Sommerburg O, Siems W, Eckl PM 2004. Cytotoxic and genotoxic effects of beta-carotene breakdown products on primary rat hepatocytes. Carcinogenesis 25 5: 827-31. doi:10.1093/carcin/bgh056. PMID 14688018. ^ Liu GY, Essex A, Buchanan JT, et al 2005. Staphylococcus aureus golden pigment impairs neutrophil killing and promotes virulence through its antioxidant activity. J. Exp. Med. 202 2: 209-15. doi:10.1084/jem.20050846. PMID 16009720. PMC:2213009. Classifications Carotenoids can have many classifications. Some are alcohols, hydrocarbons, ethers, epoxides, ketones, acids, etc. They can be classified also into Apo Carotenoids, Nor and Seco Carotenoids, retro Carotenoids, retro Apo Carotenoids and Higher Carotenoids. See also Phytochemistry List of phytochemicals and foods in which they are prominent External links Wikimedia Commons has media related to: Carotenoids http://www.carotenoidsociety.org/ Carotenoid Terpenoids Carotenoids as Flavor and Fragrance Precursors MeSH Carotenoids 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 Carotenoids Carotenes: Carotene Alpha-carotene · Beta-carotene · Lycopene · Phytoene Phytofluene · Neurosporene Retinoids: Acitretin · Alitretinoin · Apocarotenal · Bexarotene · Etretinate · Fenretinide · Isotretinoin · Retinaldehyde · Tazarotene · Vitamin A Retinol, Tretinoin Xanthophylls: Antheraxanthin · Astaxanthin · Canthaxanthin · Citranaxanthin · Cryptoxanthin · Diadinoxanthin · Diatoxanthin · Dinoxanthin · Flavoxanthin · Fucoxanthin · Lutein · Neoxanthin · Rhodoxanthin · Rubixanthin · Violaxanthin · Zeaxanthin Other: Crocin · Crocetin · Peridinin · Food orange 7 Retrieved from http://en..org/wiki/Carotenoid Categories: Bioindicators | Carotenoids | Photosynthesis | PigmentsHidden categories: Articles needing additional references from June 2008 | All articles with statements | Articles with statements since June 2008 | Articles with statements since August 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 БългарÑ?ки Català Česky Deutsch Español Esperanto Français Bahasa Indonesia Italiano Nederlands 日本語 Polski Português РуÑ?Ñ?кий СрпÑ?ки / Srpski Suomi Svenska Tiếng Việt Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 29 July 2008, at 10:36
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