Carotenoid

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

Carotenoids, also called tetraterpenoids, are organic pigments that are found in the chloroplasts and chromoplasts of plants and some other photosynthetic organisms, including some bacteria and some fungi. Carotenoids can be produced from fats and other basic organic metabolic building blocks by all these organisms. The only animals known to produce 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 derivatives of tetraterpenes, 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 retinol), 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.

Biosynthesis[edit]

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

Properties[edit]

Main articles: carotenes and xanthophylls

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. Dried carrots have the highest amount of carotene of any food per 100 gram serving, measured in retinol activity equivalents (provitamin A equivalents).[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 lipophilic due to the presence of long unsaturated aliphatic chains as in some fatty acids. The physiological absorption of these fat-soluble vitamins in humans and other organisms depends directly on the presence of fats and bile salts.[5]

Physiological effects[edit]

Reviews of epidemiological studies seeking correlations between carotenoid consumption in food and clinical outcomes have come to various conclusions:

  • a 2016 review looking at correlations between diets rich in fruit and vegetables (some of which are high in carotenoids) and lung cancer found a protective effect up to 400g/day;[6]
  • a 2015 review found that foods high in carotenoids appear to be protective against head and neck cancers;[7]
  • another 2015 review looking at whether caretenoids can prevent prostate cancer found that while several studies found correlations between diets rich in carotenoids appeared to have a protective effect, evidence is lacking to determine whether this is due to carotenoids per se;[8]
  • a 2014 review found no correlation between consumption of foods high in carotenoids and vitamin A and the risk of getting Parkinson's Disease[9]
  • another 2014 review found no conflicting results in studies of dietary consumption of carotenoids and the risk of getting breast cancer[10]

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 and scales of the yellow morph of common wall lizards are due to carotenoids.[11][citation needed] 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 visible indicators of individual health, and hence are used by animals when selecting potential mates.[12]

Simplified carotenoid synthesis pathway.

Plant colors[edit]

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.[13] 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.[14]

Aroma chemicals[edit]

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[edit]

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.[15]

Question of synthesis in the corpus luteum[edit]

Following a 1968 report that beta-carotene was synthesized in laboratory conditions in slices of corpus luteum from cows, an organ known to concentrate beta-carotene (hence its color and name), attempts have been made to replicate these findings, but have not succeeded. The idea is not presently accepted by the scientific community.[16] Rather, the mammalian corpus luteum, like the macula lutea in the retina of the mammalian eye, merely concentrates carotenoids from the diet.

Artificial synthesis[edit]

Microorganisms can be genetically modified[17] to produce certain C40 carotenoids, including lycopene and beta carotene.[18]

Naturally occurring carotenoids[edit]

  • Hydrocarbons
  • Alcohols
  • 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
  • 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
  • Epoxides
  • Aldehydes
  • Acids and acid esters
  • Ketones
  • 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
  • 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
  • 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
  • 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'-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

See also[edit]

References[edit]

  1. ^ Boran Altincicek; Jennifer L. Kovacs; Nicole M. Gerardo (2011). "Horizontally transferred fungal carotenoid genes in the two-spotted spider mite Tetranychus urticae". Biology Letters. 8 (2): 253–257. doi:10.1098/rsbl.2011.0704. PMC 3297373free to read. PMID 21920958. 
  2. ^ Armstrong GA, Hearst JE (1996). "Carotenoids 2: Genetics and molecular biology of carotenoid pigment biosynthesis". FASEB J. 10 (2): 228–37. PMID 8641556. 
  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. ^ "Foods highest in Retinol Activity Equivalent". nutritiondata.self.com. Retrieved 2015-12-04. 
  5. ^ Linus Pauling Institute. "Micronutrient Information Center-Carotenoids". Retrieved 3 August 2013.
  6. ^ Vieira AR et al. Fruits, vegetables and lung cancer risk: a systematic review and meta-analysis. Ann Oncol. 2016 Jan;27(1):81-96. PMID 2637128
  7. ^ Leoncini E et al. Carotenoid Intake from Natural Sources and Head and Neck Cancer: A Systematic Review and Meta-analysis of Epidemiological Studies. Cancer Epidemiol Biomarkers Prev. 2015 Jul;24(7):1003-11. PMID 25873578
  8. ^ Soares Nda C et al. Anticancer properties of carotenoids in prostate cancer. A review. Histol Histopathol. 2015 Oct;30(10):1143-54. PMID 26058846
  9. ^ Takeda A, et al. Vitamin A and carotenoids and the risk of Parkinson's disease: a systematic review and meta-analysis. Neuroepidemiology. 2014;42(1):25-38. PMID 24356061
  10. ^ Chajès V, Romieu I Nutrition and breast cancer. Maturitas. 2014 Jan;77(1):7-11. PMID 24215727
  11. ^ Sacchi, Roberto (4 June 2013). "Colour variation in the polymorphic common wall lizard (Podarcis muralis): An analysis using the RGB colour system". Zoologischer Anzeiger. doi:10.1016/j.jcz.2013.03.001. 
  12. ^ Whitehead RD, Ozakinci G, Perrett DI (2012). "Attractive skin coloration: harnessing sexual selection to improve diet and health". Evol Psychol. 10 (5): 842–54. doi:10.1177/147470491201000507. PMID 23253790. 
  13. ^ 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. doi:10.1016/j.tree.2008.10.006. PMID 19178979. 
  14. ^ Davies, Kevin M. (2004). Plant pigments and their manipulation. Wiley-Blackwell. p. 6. ISBN 1-4051-1737-0. 
  15. ^ 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. PMC 2213009free to read. PMID 16009720. 
  16. ^ 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.
  17. ^ Patent Pending: US Application Number 11/817,120
  18. ^ "Biosynthesis of carotenoids". 
  19. ^ 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

External links[edit]