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Carotenoid

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Title: Carotenoid  
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Carotenoid

The orange ring surrounding Grand Prismatic Spring is due to carotenoid molecules, produced by mats of algae and bacteria.

Carotenoids are aphids and spider mites, which acquired the ability and genes from fungi.[1] Carotenoids from the diet are stored in the fatty tissues of animals, and exclusively carnivorous animals obtain the compounds from animal fat.

There are over 600 known carotenoids; they are split into two classes, xanthophylls (which contain oxygen) and carotenes (which are purely hydrocarbons, and contain no oxygen). All carotenoids are tetraterpenoids, meaning that they are produced from 8 isoprene molecules and contain 40 carbon atoms. In general, carotenoids absorb wavelengths ranging from 400-550 nanometers (violet to green light). This causes the compounds to be deeply colored yellow, orange, or red. Carotenoids are the dominant pigment in autumn leaf coloration of about 15-30% of tree species, but many plant colors, especially reds and purples, are due to other classes of chemicals.

Carotenoids serve two key roles in plants and algae: they absorb light energy for use in photosynthesis, and they protect chlorophyll from photodamage.[2] Carotenoids that contain unsubstituted beta-ionone rings (including beta-carotene, alpha-carotene, beta-cryptoxanthin and gamma-carotene) have vitamin A activity (meaning that they can be converted to retinal), and these and other carotenoids can also act as antioxidants. In the eye, certain other carotenoids (lutein, astaxanthin,[3] and zeaxanthin) apparently act directly to absorb damaging blue and near-ultraviolet light, in order to protect the macula of the retina, the part of the eye with the sharpest vision.

Contents

  • Biosynthesis 1
  • Properties 2
  • Diet 3
  • Physiological effects 4
  • Plant colors 5
  • Aroma chemicals 6
  • Disease 7
    • Question of synthesis in the corpus luteum 7.1
    • Artificial synthesis 7.2
  • Naturally occurring carotenoids 8
  • See also 9
  • References 10
  • External links 11

Biosynthesis

CRT is the gene cluster responsible for the biosynthesis of carotenoids.

Properties

Carotenoids belong to the category of tetraterpenoids (i.e., they contain 40 carbon atoms, being built from four terpene units each containing 10 carbon atoms). Structurally, carotenoids take the form of a polyene hydrocarbon chain which is sometimes terminated by rings, and may or may not have additional oxygen atoms attached.

Probably the most well-known carotenoid is the one that gives this second group its name, carotene, found in carrots (also apricots) and are responsible for their bright orange color. Crude palm oil, however, is the richest source of carotenoids in nature in terms of retinol (provitamin A) equivalent.[4] Vietnamese Gac fruit contains the highest known concentration of the carotenoid lycopene.

Their color, 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 conjugated 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.

Carotenoids are usually bile salts.[5]

Diet

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.[6] Although a recent meta-analysis of 68 reliable antioxidant supplementation experiments involving a total of 232,606 individuals concluded additional β-carotene from supplements is unlikely to be beneficial and may actually be harmful,[7] this may be due to the inclusion of studies involving smokers - β-carotene under intense oxidative stress (e.g. induced by heavy smoking) gives breakdown products that reduce plasma vitamin A and worsen the lung cell proliferation induced by smoke.[8][9] With the notable exception of the gac fruit and crude palm oil, most carotenoid-rich fruits and vegetables are low in lipids. 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 either avocado fruit or oil significantly enhanced the subjects' absorption of all carotenoids tested (α-carotene, β-carotene, lycopene, and lutein).[10]

Physiological effects

Carotenoids have many physiological functions. Epidemiological studies of high intake show no proven clinical value of ingested carotenoids individually or in combination, with the exception of provitamin A carotenes.[11] Studies have shown that people with high β-carotene intake and high plasma levels of β-carotene or β-cryptoxanthin have significantly reduced risk of renal cancer and lung cancer, respectively.[12] However, studies of supplementation with large doses of β-carotene in smokers have shown an increase in cancer risk (possibly because β-carotene under intense oxidative stress (e.g. induced by heavy smoking) gives breakdown products that reduce plasma vitamin A and worsen the lung cell proliferation induced by smoke).[8]

Humans and animals are mostly incapable of synthesizing carotenoids, and must obtain them through their diet. Carotenoids are a common and often ornamental feature in animals. For example, the pink color of flamingos and salmon, and the red coloring of cooked lobsters are due to carotenoids. It has been proposed that carotenoids are used in ornamental traits (for extreme examples see puffin birds) 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.[13]

In the macula lutea of the human eye, certain carotenoids are actively concentrated to the point that they cause a yellow coloring, and this may help to protect the retina from blue and actinic light, in the same way that carotenoids protect the photosystems of plants. Carotenoids are also actively concentrated in the corpus luteum of the ovaries, where they impart the characteristic color, and may act as general antioxidants.

Simplified carotenoid synthesis pathway.

Plant colors

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 mature leaves are often not obvious because of the masking presence of chlorophyll. When chlorophyll is not present, as in autumn foliage, the yellows and oranges of the carotenoids are predominant. For the same reason, carotenoid colors often predominate in ripe fruit after being unmasked by the disappearance of chlorophyll.

Carotenoids give the characteristic color to carrots, corn, canaries, and daffodils, as well as egg yolks, rutabagas, buttercups, and bananas.

Carotenoids are responsible for the brilliant yellows and oranges that tint deciduous foliage (such as dying autumn leaves) of certain hardwood species as hickories, ash, maple, yellow poplar, aspen, birch, black cherry, sycamore, cottonwood, sassafras, and alder. Carotenoids are the dominant pigment in autumn leaf coloration of about 15-30% of tree species.[14] However, the reds, the purples, and their blended combinations that decorate autumn foliage usually come from another group of pigments in the cells called anthocyanins. Unlike the carotenoids, these pigments are not present in the leaf throughout the growing season, but are actively produced towards the end of summer.[15]

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 β-damascenone and β-ionone although low in concentration in rose distillates are the key odor-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

Some carotenoids are produced by bacteria to protect themselves from oxidative immune attack. The golden pigment that gives some strains of Staphylococcus aureus their name (aureusis = golden) is a carotenoid called staphyloxanthin. This carotenoid is a virulence factor with an antioxidant action that helps the microbe evade death by reactive oxygen species used by the host immune system.[16]

Question of synthesis in the corpus luteum

Following a 1968 report that beta-carotene was synthesized in laboratory conditions in slices of

  • Carotenoid Terpenoids
  • Carotenoids as Flavor and Fragrance Precursors
  • Carotenoid gene in aphids
  • International Carotenoid Society
  • Carotenoids at the US National Library of Medicine Medical Subject Headings (MeSH)

External links

  1. ^ Boran Altincicek, Jennifer L. Kovacs & Nicole M. Gerardo (2011). "Tetranychus urticae"Horizontally transferred fungal carotenoid genes in the two-spotted spider mite .  
  2. ^ Armstrong GA, Hearst JE (1996). "Carotenoids 2: Genetics and molecular biology of carotenoid pigment biosynthesis". FASEB J. 10 (2): 228–37.  
  3. ^ Kidd, Parris (December 2011). "Astaxanthin, Cell Membrane Nutrient with Diverse Clinical Benefits and Anti-Aging Potential" (PDF). Alternative Medicine Review 16 (4): 335–364. 
  4. ^ Choo Yuen May Palm oil carotenoids
  5. ^ Linus Pauling Institute. "Micronutrient Information Center-Carotenoids". Retrieved 3 August 2013.
  6. ^ A. T. Diplock1, J.-L. Charleux, G. Crozier-Willi, F. J. Kok, C. Rice-Evans, M. Roberfroid, W. Stahl, J. Vina-Ribes. Functional food science and defence against reactive oxidative species, British Journal of Nutrition 1998, 80, Suppl. 1, S77–S112
  7. ^ Bjelakovic G; Nikolova, D; Gluud, LL; Simonetti, RG; Gluud, C; 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.  
  8. ^ a b Alija AJ, Bresgen N, Sommerburg O, Siems W, Eckl PM (2004). "Cytotoxic and genotoxic effects of β-carotene breakdown products on primary rat hepatocytes". Carcinogenesis 25 (5): 827–31.  
  9. ^ It is known that taking β-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.
  10. ^ Unlu N; Bohn, T; Clinton, SK; Schwartz, SJ; et al. (1 March 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.  
  11. ^ Sommer A, Vyas KS (2012). "A global clinical view on vitamin A and carotenoids". Am J Clin Nutr 96 (5): 1204S–6S.  
  12. ^ Miller PE, Snyder DC (2012). "Phytochemicals and cancer risk: a review of the epidemiological evidence". Nutr Clin Pract 27 (5): 599–612.  
  13. ^ Whitehead RD, Ozakinci G, Perrett DI (2012). "Attractive skin coloration: harnessing sexual selection to improve diet and health". Evol Psychol 10 (5): 842–54.  
  14. ^ Archetti, Marco; Döring, Thomas F.; Hagen, Snorre B.; Hughes, Nicole M.; Leather, Simon R.; Lee, David W.; Lev-Yadun, Simcha; Manetas, Yiannis; Ougham, Helen J. (2011). "Unravelling the evolution of autumn colours: an interdisciplinary approach". Trends in Ecology & Evolution 24 (3): 166–73.  
  15. ^ Davies, Kevin M. (2004). Plant pigments and their manipulation.  
  16. ^ 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.  
  17. ^ Brian H. Davies Carotenoid metabolism as a preparation for function. Pure & Applied Chemistry, Vol. 63, No. 1, pp. 131-140, 1991. available online. Accessed April 30, 2010.
  18. ^ Patent Pending: US Application Number 11/817,120
  19. ^ "Biosynthesis of carotenoids". 
  20. ^ Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene. Seyoung Choi and Sangho Koo, J. Org. Chem., 2005, 70 (8), pages 3328–3331, doi:10.1021/jo050101l

References

See also

  • Higher carotenoids
    • Nonaprenoxanthin 2-(4-Hydroxy-3-methyl-2-butenyl)-7',8',11',12'-tetrahydro-e,y-carotene
    • Decaprenoxanthin 2,2'-Bis(4-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'-Bis(3-hydroxy-3-methylbutyl)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-y,y-carotene-1,1'-dio
  • 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
  • Nor- and seco-carotenoids
    • Actinioerythrin 3,3'-Bisacyloxy-2,2'-dinor-b,b-carotene-4,4'-dione
    • β-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-α-carotenone 5,6-Seco-b,e-carotene-5,6-dione
    • Semi-β-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
  • Apocarotenoids
    • β-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-β-caroten-10'-al
    • Bixin 6'-Methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioate
    • Citranaxanthin 5',6'-Dihydro-5'-apo-β-caroten-6'-one or 5',6'-dihydro-5'-apo-18'-nor-β-caroten-6'-one or 6'-methyl-6'-apo-β-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
  • Esters of alcohols
    • Astacein 3,3'-Bispalmitoyloxy-2,3,2',3'-tetradehydro-β,β-carotene-4,4'-dione or 3,3'-dihydroxy-2,3,2',3'-tetradehydro-β,β-carotene-4,4'-dione dipalmitate
    • Fucoxanthin 3'-Acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-β,β-caroten-8-one
    • Isofucoxanthin 3'-Acetoxy-3,5,5'-trihydroxy-6',7'-didehydro-5,8,5',6'-tetrahydro-β,β-caroten-8-one
    • Physalien
    • Zeaxanthin (3R,3'R)-3,3'-Bispalmitoyloxy-β,β-carotene or (3R,3'R)-β,β-carotene-3,3'-diol
    • Siphonein 3,3'-Dihydroxy-19-lauroyloxy-7,8-dihydro-β,ε-caroten-8-one or 3,19,3'-trihydroxy-7,8-dihydro-β,ε-caroten-8-one 19-laurate
  • Ethers
    • Rhodovibrin 1'-Methoxy-3',4'-didehydro-1,2,1',2'-tetrahydro-γ,γ-caroten-1-ol
    • Spheroidene 1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-γ,γ-carotene
  • Glycosides
    • Oscillaxanthin 2,2'-Bis(β-L-rhamnopyranosyloxy)-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-γ,γ-carotene-1,1'-diol
    • Phleixanthophyll 1'-(β-D-Glucopyranosyloxy)-3',4'-didehydro-1',2'-dihydro-β,γ-caroten-2'-ol

Naturally occurring carotenoids

Microorganisms can be genetically modified[18] to produce certain C40 carotenoids, including lycopene and beta carotene.[19]

Artificial synthesis

of the mammalian eye, merely concentrates carotenoids from the diet. retina in the macula lutea Rather, the mammalian corpus luteum, like the [17]

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