Canthaxanthin: From molecule to function

Molecular Nutrition and Food Research

Volumn 61, Issue 6, 2017, Pages

  Esatbeyoglu, Tuba ^a   Rimbach, Gerald ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

Carotenoid; Food colorant; Health benefits; Synthesis; Xanthophyll

Indexed keywords

ANTIOXIDANT; CANTHAXANTHIN; CATALASE; FOOD ADDITIVE; LOW DENSITY LIPOPROTEIN CHOLESTEROL; SUPEROXIDE DISMUTASE;

AGARICALES; ANIMAL; BIOAVAILABILITY; CELL LINE; CHEMISTRY; DIET; GREEN ALGA; HUMAN; METABOLISM; MICROALGA; OXIDATION REDUCTION REACTION; TISSUE DISTRIBUTION;

AGARICALES; ANIMALS; ANTIOXIDANTS; BIOLOGICAL AVAILABILITY; CANTHAXANTHIN; CATALASE; CELL LINE; CHLOROPHYTA; CHOLESTEROL, LDL; DIET; FOOD ADDITIVES; HUMANS; MICROALGAE; OXIDATION-REDUCTION; SUPEROXIDE DISMUTASE; TISSUE DISTRIBUTION;

EID: 85002625874     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.201600469     Document Type: Review

References (142)

1. Venugopalan, V., Tripathi, S. K., Nahar, P., Saradhi, P. P. et al., Characterization of canthaxanthin isomers isolated from a new soil Dietzia sp. and their antioxidant activities. J. Microbiol. Biotechnol. 2013, 23, 237–245.
2. Sigma-Aldrich, Safety data sheet according to Regulation (EC) No. 1907/2006 Version 5.0 Revision Date 25.07.2012. http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=DE&language=EN-generic&productNumber=32993&brand=SIAL&PageToGoToURL=http://www.sigmaaldrich.com/catalog/product/sial/32993?lang=de (accessed: February 2016)
3. The International Agency for Research on Cancer, IARC Handbooks of cancer prevention: Carotenoids, Volume 2, IARC, Lyon/France, 1998.
4. Meléndez-Marténez, A. J., Britton, G., Vicario, I. M., Heredia, F. J., Relationship between the colour and the chemical structure of carotenoid pigments. Food Chem. 2006, 101, 1145–1150.
5. Britton, G., Structure and properties of carotenoids in relation to function. FASEB J. 1995, 9, 1551–1558.
6. Gammone, M. A., Riccioni, G., D'Orazio, N., Marine carotenoids against oxidative stress: effects on human health. Mar. Drugs 2015, 13, 6226–6246.
7. Fraser, P. D., Bramley, P. M., The biosynthesis and nutritional uses of carotenoids. Prog. Lipid Res. 2004, 43, 228–265.
8. FAO JECFA Monographs 1, Canthaxanthin. http://www.fao.org/ag/agn/jecfa-additives/specs/monograph5/additive-101-m5.pdf (accessed: February 2016).
9. Yemelyanov, A. Y., Katz, N. B., Bernstein, P. S., Ligand-binding characterization of xanthophyll carotenoids to solubilized membrane proteins derived from human retina. Exp. Eye Res. 2001, 72, 381–392.
10. Qian, C., Zhang, T., Pi, S., Chen, X., Solubility of canthaxanthin in pure solvents from (293.15 to 343.15) K. J. Chem. Eng. Data 2009, 54, 1115–1116.
11. Mordi, R. C., Walton, J. C., Identification of products from canthaxanthin oxidation. Food Chem. 2016, 197, 836–840.
12. Mortensen, A., Skibsted, L. H., Kinetics and mechanism of the primary steps of degradation of carotenoids by acid in homogeneous solution. J. Agric. Food Chem. 2000, 48, 279–286.
13. Kotíková, Z., Šulc, M., Lachman, J., Pivec, V. et al., Carotenoid profile and retention in yellow-, purple- and red-fleshed potatoes after thermal processing. Food Chem. 2016, 197, 992–1001.
14. Nimalaratne, C., Lopes-Lutz, D., Schieber, A., Wu, J., Effect of domestic cooking methods on egg yolk xanthophylls. J. Agric. Food Chem. 2012, 60, 12547–12552.
15. Schieber, A., Carle, R., Occurrence of carotenoid cis-isomers in food: technological, analytical, and nutritional implications. Trends Food Sci. Technol. 2005, 16, 416–422.
16. Nelis, H. J., Lavens, P., Moens, L., Sorgeloos, P. et al., cis-Canthaxanthins. Unusual carotenoids in the eggs and the reproductive system of female brine shrimp Artemia. J. Biol. Chem. 1984, 259, 6063–6066.
17. BCC Research, Boom in astaxanthin supplements boosting global carotenoid market, according to BCC research. http://www.bccresearch.com/pressroom/fod/boom-in-astaxanthin-supplements-boosting-global-carotenoid-market-according-to-bcc-research (accessed: March 2016).
18. BCC Research, The global market for carotenoids. http://www.bccresearch.com/market-research/food-and-beverage/carotenoids-global-market-report-fod025e.html (accessed March: 2016).
19. Rosenberger, M., McDougal, P., Bahr, J., Canthaxanthin. A new total synthesis. J. Org. Chem. 1982, 47, 2130–2134.
20. Jin, E., Polle, J. E.W., Lee, H. K., Hyun, S. M. et al., Xanthophylls in microalgae: from biosynthesis to biotechnological mass production and application. J. Microbiol. Biotechnol. 2003, 13, 165–174.
21. Hu, C.-W., Chuang, L.-T., Yu, P.-C., Nathan Chen, C.-N., Pigment production by a new thermotolerant microalga Coelastrella sp. F50. Food Chem. 2013, 138, 2071–2078.
22. Ye, R. W., Stead, K. J., Yao, H., He, H., Mutational and functional analysis of the β-carotene ketolase involved in the production of canthaxanthin and astaxanthin. Appl. Environ. Microbiol. 2006, 72, 5829–5837.
23. Papp, T., Csernetics, Á., Nagy, G., Bencsik, O. et al., Canthaxanthin production with modified Mucor circinelloides strains. Appl. Microbiol. Biotechnol. 2013, 97, 4937–4950.
24. Scaife, M. A., Ma, C. A., Armenta, R. E., Efficient extraction of canthaxanthin from Escherichia coli by a 2-step process with organic solvents. Bioresour. Technol. 2012, 111, 276–281.
25. Widmer, E., Synthetic advances in the carotenoid field. Pure Appl. Chem. 1985, 57, 741–752.
26. Rosenberger, M., McDougal, P., Saucy, G., Bahr, J., New approaches to the synthesis of canthaxanthin. Pure Appl. Chem. 1979, 51, 871–886.
27. Ernst, H., Recent advances in industrial carotenoid synthesis. Pure Appl. Chem. 2002, 74, 2213–2226.
28. Bernhard, K., Mayer, H., Recent advances in the synthesis of achiral carotenoids. Pure Appl. Chem. 1991, 63, 35–44.
29. Choi, S., Koo, S., Efficient syntheses of the keto-carotenoids canthaxanthin, astaxanthin, and astacene. J. Org. Chem. 2005, 70, 3328–3331.
30. European Commission, Opinion of the scientific committee on animal nutrition on the use of canthaxanthin in feedingstuffs for salmon and trout, laying hens, and other poultry, 2002, 1–29. http://ec.europa.eu/food/fs/sc/scan/out81_en.pdf (accessed: November 2015)
31. Chuyen, V. H., Eun, J.-B., Marine carotenoids: Bioactivities and potential benefits to human health. Crit. Rev. Food Sci. Nutr. 2015, doi: 10.1080/10408398.2015.1063477.
32. Haxo, F., Carotenoids of the mushroom Cantharellus cinnabarinus. Bot. Gaz. 1950, 112, 228–232.
33. Choubert, G., Heinrich, O., Carotenoid pigments of the green alga Haematococcus pluvialis: assay on rainbow trout, Oncorhynchus mykiss, pigmentation in comparison with synthetic astaxanthin and canthaxanthin. Aquaculture 1993, 112, 217–226.
34. Hua-Bin, L., Fan, K.-W., Chen, F., Isolation and purification of canthaxanthin from the microalga Chlorella zofingiensis by high-speed counter-current chromatography. J. Sep. Sci. 2006, 29, 699–703.
35. Grama, B. S., Chader, S., Khelifi, D., Agathos, S. N. et al., Induction of canthaxanthin production in a Dactylococcus microalga isolated from the Algerian Sahara. Bioresour. Technol. 2014, 151, 297–305.
36. Hojjati, M., Razavi, S. H., Rezaei, K., Gilani, K., Stabilization of canthaxanthin produced by Dietzia natronolimnaea HS-1 with spray drying microencapsulation. J. Food Sci. Technol. 2014, 51, 2134–40.
37. Schweigert, F. J., Metabolism of carotenoids in mammals, In: Britton, G., Liaaen-Jensen, S., Pfander, H. (Eds.), Carotenoids: Isolation and Analysis, Vol. 1A, Birkhäuser Verlag, Basel 1998.
38. Amaya, E., Becquet, P., Carné, S., Peris, S. et al., Carotenoids in animal nutrition, Fefana, Bruxelles 2014.
39. Czeczuga, B., Czeczuga-Semeniuk, E., Comparative studies of carotenoids in four species of crayfish. Crustaceana 1999, 72, 693–700.
40. Mendes-Pinto, M. M., LaFountain, A. M., Stoddard, M. C., Prum, R. O. et al., Variation in carotenoid-protein interaction in bird feathers produces novel plumage coloration. J. R. Soc. Interface 2012, 9, 3338–3350.
41. Thomas, D. B., McGraw, K. J., James, H. F., Madden, O., Non-destructive descriptions of carotenoids in feathers using Raman spectroscopy. Anal. Methods 2014, 6, 1301–1308.
42. Poole, W. R., Webb, J. H., Matthews, M. A., Youngson, A. F., Occurrence of canthaxanthin in Atlantic salmon, Salmo salar L., fry in Irish rivers as an indicator of escaped farmed salmon. Fish. Manag. Ecol. 2000, 7, 377–385.
43. EFSA (European Food Safety Authority), Scientific opinion on the re-evaluation of canthaxanthin (E 161 g) as a food additive. EFSA J. 2010, 8 (1852), 42.
44. Brizio, P., Benedetto, A., Righetti, M., Prearo, M. et al., Astaxanthin and canthaxanthin (xanthophyll) as supplements in rainbow trout diet: In vivo assessment of residual levels and contributions to human health. J. Agric. Food Chem. 2013, 61, 10954–10959.
45. Breithaupt, D. E., Modern application of xanthophylls in animal feeding - a review. Trends Food Sci. Technol. 2007, 18, 501–506.
46. Henmi, H., Hata, M., Takeuchi, M., Studies on the carotenoids in the muscle of salmon - V. Combination of astaxanthin and canthaxanthin with bovine serum albumin and egg albumin. Comp. Biochem. Physiol. B 1991, 99, 609–612.
47. Surai, P. F., The antioxidant properties of canthaxanthin and its potential effects in the poultry eggs and on embryonic development of the chick. Part 2. Worlds. Poult. Sci. J. 2012, 68, 717–726.
48. Saini, R. K., Nile, S. H., Park, S. W., Carotenoids from fruits and vegetables: chemistry, analysis, occurrence, bioavailability and biological activities. Food Res. Int. 2015, 76, 735–750.
49. Clark, R. M., Furr, H. C., Absorption of canthaxanthin by the rat is influenced by total lipid in the intestinal lumen. Lipids 2001, 36, 473–475.
50. Westphal, A., Böhm, V., Carotenoids - Properties, distribution, bioavailability, metabolism and health effects. Ernährungsumschau 2015, 62, 196–207.
51. Biehler, E., Kaulmann, A., Hoffmann, L., Krause, E. et al., Dietary and host-related factors influencing carotenoid bioaccessibility from spinach (Spinacia oleracea). Food Chem. 2011, 125, 1328–1334.
52. Reboul, E., Richelle, M., Perrot, E., Desmoulins-Malezet, C. et al., Bioaccessibility of carotenoids and vitamin E from their main dietary sources. J. Agric Food Chem. 2006, 54, 8749−8755.
53. Unlu, N. Z., Bohn, T., Clinton, S. K., Schwartz, S. J., Carotenoid absorption from salad and salsa by humans is enhanced by the addition of avocado or avocado oil. Hum. Nutr. Metab. 2005, 135, 431–436.
54. Maiani, G., Castón, M. J. P., Catasta, G., Toti, E. et al., Carotenoids: actual knowledge on food sources, intakes, stability and bioavailability and their protective role in humans. Mol. Nutr. Food Res. 2009, 53, S194–S218.
55. Parker, R. S., Absorption, metabolism, and transport of carotenoids. FASEB J. 1996, 10, 542–551.
56. Castenmiller, J. J., West, C. E., Linssen, J. P., van het Hof, K. H. et al., The food matrix of spinach is a limiting factor in determining the bioavailability of β-carotene and to a lesser extent of lutein in humans. J. Nutr. 1999, 129, 349–355.
57. Schweiggert, R. M., Kopec, R. E., Villalobos-Gutierrez, M. G., Högel, J. et al., Carotenoids are more bioavailable from papaya than from tomato and carrot in humans: a randomised cross-over study. Br. J. Nutr. 2014, 111, 490–498.
58. Schweiggert, R. M., Carle, R., Carotenoid deposition in plant and animal foods and its impact on bioavailability. Crit. Rev. Food Sci. Nutr. 2015, 8398, DOI: 10.1080/10408398.2015.1012756.
59. Faulks, R. M., Southon, S., Challenges to understanding and measuring carotenoid bioavailability. Biochim. Biophys. Acta 2005, 1740, 95–100.
60. Yeum, K.-J., Russell, R. M., Carotenoid bioavailability and bioconversion. Annu. Rev. Nutr. 2002, 22, 483–504.
61. Borel, P., Desmarchelier, C., Nowicki, M., Bott, R. et al., Interindividual variability of lutein bioavailability in healthy men: characterization, genetic variants involved, and relation with fasting. Am. J. Clin. Nutr. 2014, 100, 168–175.
62. Jackson, H., Braun, C. L., Ernst, H., The chemistry of novel xanthophyll carotenoids. Am. J. Cardiol. 2008, 101, 50D–57D.
63. Reboul, E., Absorption of vitamin A and carotenoids by the enterocyte: focus on transport proteins. Nutrients 2013, 5, 3563–3581.
64. Bohn, T., Bioavailability of non-provitamin A carotenoids. Curr. Nutr. Food Sci. 2008, 4, 240–258.
65. Priyadarshani, A. M., A review on factors influencing bioaccessibility and bioefficacy of carotenoids. Crit. Rev. Food Sci. Nutr. 2015, DOI: 10.1080/10408398.2015.1023431.
66. Borel, P., Genetic variations involved in interindividual variability in carotenoid status. Mol. Nutr. Food Res. 2012, 56, 228–240.
67. Tang, G., Blanco, M. C., Fox, J. G., Russell, R. M., Supplementing ferrets with canthaxanthin affects the tissue distributions of canthaxanthin, other carotenoids, vitamin A and vitamin E. J. Nutr. 1995, 125, 1945–1951.
68. Gradelet, S., Astorg, P., Leclerc, J., Chevalier, J. et al., Effects of canthaxanthin, astaxanthin, lycopene and lutein on liver xenobiotic-metabolizing enzymes in the rat. Xenobiotica 1996, 26, 49–63.
69. Astorg, P., Gradelet, S., Leclerc, J., Canivenc, M. C. et al., Effects of beta-carotene and canthaxanthin on liver xenobiotic-metabolizing enzymes in the rat. Food Chem. Toxicol. 1994, 32, 735–742.
70. Sujak, A., Gabrielska, J., Milanowska, J., Mazurek, P. et al., Studies on canthaxanthin in lipid membranes. Biochim. Biophys. Acta 2005, 1712, 17–28.
71. Sujak, A., Exceptional molecular organization of canthaxanthin in lipid membranes. Acta Biochim. Pol. 2012, 59, 31–33.
72. Van den Berg, H., Carotenoid interactions. Nutr. Rev. 1999, 57, 1–10.
73. White, W. S., Stacewicz-Sapuntzakis, M., Erdman, J. W. Jr., Bowen, P. E., Pharmacokinetics of beta-carotene and canthaxanthin after ingestion of individual and combined doses by human subjects. J. Am. Coll. Nutr. 1994, 13, 665–671.
74. Paetau, I., Chen, H., Goh, N. M.-Y., White, W. S., Interactions in the postprandial appearance of β-carotene and canthaxanthin in plasma triacylglycerol-rich lipoproteins in humans. Am. J. Clin. Nutr. 1997, 66, 1133–1143.
75. Hageman, S. H., She, L., Furr, H. C., Clark, R. M., Excess vitamin E decreases canthaxanthin absorption in the rat. Lipids 1999, 34, 627–631.
76. Carail, M., Caris-Veyrat, C., Carotenoid oxidation products: from villain to saviour? Pure Appl. Chem. 2006, 78, 1493–1503.
77. Bausch, J., Liechti, H., Oesterhelt, G., Kistler, A., Isolation and identification of a major urinary canthaxanthin metabolite in rats. Int. J. Vitam. Nutr. Res. 1999, 69, 268–272.
78. Tyczkowski, J. K., Yagen, B., Hamilton, P. B., Metabolism of canthaxanthin, a red diketocarotenoid, by chickens. Poult Sci. 1988, 67, 787–793.
79. FDA (U. S. Food and Drug Administration), CFR - Code of Federal Regulations Title 21. Part 73 - Listing of color additives exempt from certification. 2009. http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=73.1075 (date assessed 03.03. 2016)
80. EFSA (European Food Safety Authority), Opinion of the scientific panel on additives and products or substances used in animal feed on the maximum residue limits for canthaxanthin in foodstuffs coming from animals fed with canthaxanthin used as a feed additive in accordance with Council Directive 70/524/EEC. EFSA J. 2007, 507, 1–19.
81. European Commission, Commission Regulation (EC) No 775/2008 of 4 August 2008 establishing maximum residue limits for the feed additive canthaxanthin in addition to the conditions provided for in Directive 2003/7/EC. Off. J. Eur. Union 2008, L207, 5–6.
82. European Commission, Commission Implementing Regulation (EU) 2015/1486 of 2 September 2015 concerning the authorisation of canthaxanthin as feed additive for certain categories of poultry, ornamental fish and ornamental birds. Off. J. Eur. Union 2015, L229, 5–8.
83. Davis, A. D., Feed and feeding practices in aquaculture, Woodhead Publishing, Sawston, Cambridge 2015, ISBN: 978-0-08-100506-4.
84. Daicker, B., Schiedt, K., Adnet, J. J., Bermond, P., Canthaxanthin retinopathy. An investigation by light and electron microscopy and physicochemical analysis. Graefes Arch. Clin. Exp. Ophthalmol. 1987, 225, 189–197.
85. Hueber, A., Rosentreter, A., Severin, M., Canthaxanthin retinopathy: long-term observations. Ophthalmic Res. 2011, 46, 103–106.
86. Sujak, A., Interactions between canthaxanthin and lipid membranes - possible mechanisms of canthaxanthin toxicity. Cell. Mol. Biol. Lett. 2009, 14, 395–410.
87. McGuinness, R., Beaumont, P., Gold dust retinopathy after the ingestion of canthaxanthine to produce skin-bronzing. Med. J. Aust. 1985, 143, 622–623.
88. FDA (U. S. Food and Drug Administration), Tanning pills. http://www.fda.gov/Cosmetics/ProductsIngredients/Products/ucm134217.htm (date accessed 22.07. 2016)
89. Beaulieu, R. A, Warwar, R. E., Buerk, B. M., Canthaxanthin retinopathy with visual loss: a case report and review. Case Rep. Ophthalmol. Med. 2013, 2013, doi: 10.1155/2013/140901.
90. Vílchez, C., Forján, E., Cuaresma, M., Bédmar, F. et al., Marine carotenoids: biological functions and commercial applications. Mar. Drugs 2011, 9, 319–333.
91. Velu, C. S., Czeczuga, B., Munuswamy, N., Carotenoprotein complexes in entomostracan crustaceans (Streptocephalus dichotomus and Moina micrura). Comp. Biochem. Physiol. Part B 2003, 135, 35–42.
92. European Commission, European Parliament and Council Directive 94/36/EC of 30 June 1994 on clours for use in foodstuffs. Off. J. Eur. Union 1994, L237, 13–29. http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:31994L0036&from=EN (accessed: March 2016)
93. European Commission, Regulation (EC) No 1831/2003 of the European Parliament and of the Council of 22 September 2003 on additives for use in animal nutrition. Off. J. Eur. Union 2003, L268, 29–43. http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32003R1831&from=PT (accessed: March 2016)
94. European Commission, Register of Feed Additives persuant to Regulation (EC) No 1831/2003, 1-182. http://ec.europa.eu/food/safety/animal-feed/feed-additives/eu-register/index_en.htm (accessed: March 2016)
95. European Commission, Commission Directive 2003/7/EC of 24 January 2003 amending the conditions for authorisation of canthaxanthin in feedingstuffs in accordance with Council Directive 70/524/EEC. Off. J. Eur. Union 2003, L22, 28–30. http://faolex.fao.org/docs/pdf/eur35893.pdf (accessed: March 2016)
96. European Commission, Commission Implementing Regultion (EU) No 684/2014 of 20 June 2014 concerning the authorisation of canthaxanthin as a feed additive for breeder hens (holder of the authorisation DSM Nutritional products Ltd). Off. J. Eur. Union 2014, L182, 20–22. http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32014R0684&from=EN (accessed: March 2016)
97. European Commission, Commission Regulation (EC) No 880/2004 of 29 April 2004 authorising without time limit the use of beta-carotene and canthaxanthin as additives in feedingstuffs belonging to the group of colouring matters including pigments. Off. J. Eur. Union 2004, L162, 68–69. http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32004R0880&from=EN (accessed: March 2016)
98. European Commission, Commission Regulation (EC) No 1288/2004 of 14 July 2004 concerning the permanent authorisation of certain additives and the provisional authorisation of a new use of an additive already authorised in feedingstuffs. Off. J. Eur. Union 2004, L243, 10–14. http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32004R1288&from=EN (accessed: March 2016)
99. Baker, R., Günther, C., The role of carotenoids in consumer choice and the likely benefits from their inclusion into products for human consumption. Trends Food Sci. Technol. 2004, 15, 484–488.
100. Bell, J., McEvoy, J., Webster, J., McGhee, F. et al., Flesh lipid and carotenoid composition of Scottish farmed Atlantic salmon (Salmo salar). J. Agric. Food Chem. 1998, 46, 119–127.
101. Torrissen O. J., Dietary delivery of carotenoids. In: Antioxidants in muscle foods. Ed.: Decker, E., Faustmann, C. and Lopez-Bote, C. J., John Wiley and Sons, Inc. Publication, New York 2000, pp. 289–313.
102. Storebakken, T., Foss, P., Huse, I., Wandsvik, A. et al., Carotenoids in diets for salmonids. III. Utilization of canthaxanthin from dry and wet diets by Atlantic salmon, rainbow trout and sea trout. Aquaculture 1986, 51, 245–255.
103. Storebakken, T., No, H. K., Pigmentation of rainbow trout. Aquaculture 1992, 100, 209–229.
104. Brulc, L., Simonovska, B., Vovk, I., Glavnik, V., Determination of egg yolk xanthophylls by isocratic high-performance liquid chromatography. J. Chromatogr. A 2013, 1318, 134–141.
105. Nimalaratne, C., Savard, P., Gauthier, S. F., Schieber, A. et al., Bioaccessibility and digestive stability of carotenoids in cooked eggs studied using a dynamic in vitro gastrointestinal model. J. Agric. Food Chem. 2015, 63, 2956–2962.
106. Islam, K. M.S., Schweigert, F. J., Comparison of three spectrophotometric methods for analysis of egg yolk carotenoids. Food Chem. 2015, 172, 233–237.
107. Rodrigues, E., Mariutti, L. R.B., Mercadante, A. Z., Scavenging capacity of marine carotenoids against reactive oxygen and nitrogen species in a membrane-mimicking system. Mar. Drugs 2012, 10, 1784–1798.
108. Fiedor, J., Burda, K., Potential role of carotenoids as antioxidants in human health and disease. Nutrients 2014, 6, 466–488.
109. Beutner, S., Bloedorn, B., Frixel, S., Blanco, I. H. et al., Quantitative assessment of antioxidant properties of natural colorants and phytochemicals: carotenoids, flavonoids, phenols and indigoids. The role of β-carotene in antioxidant functions. J. Sci. Food Agric. 2001, 81, 559–568.
110. Woodall, A. A., Lee, S. W. M., Weesie, R. J., Jackson, M. J. et al., Oxidation of carotenoids by free radicals: relationship between structure and reactivity. Biochim. Biophys. Acta 1997, 1336, 33–42.
111. Chang, C.-S., Chang, C.-L., Lai, G.-H., Reactive oxygen species scavenging activities in a chemiluminescence model and neuroprotection in rat pheochromocytoma cells by astaxanthin, beta-carotene, and canthaxanthin. Kaohsiung J. Med. Sci. 2013, 29, 412–421.
112. Cantrell, A., McGarvey, D. J., Truscott, G. T., Rancan, F. et al., Singlet oxygen quenching by dietary carotenoids in a model membrane environment. Arch. Biochem. Biophys. 2003, 412, 47–54.
113. Shih, C.-K., Chang, J.-H., Yang, S.-H., Chou, T.-W. et al., β-Carotene and canthaxanthin alter the pro-oxidation and antioxidation balance in rats fed a high-cholesterol and high-fat diet. Br. J. Nutr. 2008, 99, 59–66.
114. Palozza, P., Calviello, G., Emilia De Leo, M., Serini, S. et al., Canthaxanthin supplementation alters antioxidant enzymes and iron concentration in liver of balb/c mice. J. Nutr. 2000, 130, 1303–1308.
115. Zhang, W., Zhang, K. Y., Ding, X. M., Bai, S. P. et al., Influence of canthaxanthin on broiler breeder reproduction, chick quality, and performance. Poult. Sci. 2011, 90, 1516–1522.
116. Suzuki, K., Inoue, T., Hioki, R., Ochiai, J. et al., Association of abdominal obesity with decreased serum levels of carotenoids in a healthy Japanese population. Clin. Nutr. 2006, 25, 780–789.
117. Chan, K.-C., Mong, M.-C., Yin, M.-C., Antioxidative and anti-inflammatory neuroprotective effects of astaxanthin and canthaxanthin in nerve growth factor differentiated PC12 cells. J. Food Sci. 2009, 74, 225–231.
118. Virgili, F., Ambra, R., Muratori, F., Natella, F. et al., Effect of oxidized low-density lipoprotein on differential gene expression in primary human endothelial cells. Antioxid. Redox Signal. 2003, 5, 237–247.
119. Linseisen, J., Hoffmann, J., Riedl, J., Wolfram, G., Effect of a single oral dose of antioxidant mixture (vitamin E, carotenoids) on the formation of cholesterol oxidation products after ex vivo LDL oxidation in humans. Eur. J. Med. Res. 1998, 3, 5–12.
120. Carpenter, K. L. H., van der Veen, C., Hird, R., Dennis, I. F. et al., The carotenoids β-carotene, canthaxanthin and zeaxanthin inhibit macrophage-mediated LDL oxidation. FEBS Lett. 1997, 401, 262–266.
121. Palozza, P., Barone, E., Mancuso, C., Picci, N., The protective role of carotenoids against 7-keto-cholesterol formation in solution. Mol. Cell. Biochem. 2008, 309, 61–68.
122. 1 metabolism. Carcinogenesis 1998, 19, 403–411.
123. Sah, N. K., Kumar, S., Subramanian, M., Devasagayam, T. P., Variation in the modulation of superoxide-induced single-strand breaks in plasmid pBR322 DNA by biological antioxidants. Biochem. Mol. Biol. Int. 1995, 35, 291–296.
124. Bianchi, L., Tateo, F., Pizzala, R., Stivala, L. A. et al., Carotenoids reduce the chromosomal damage induced by bleomycin in human cultured lymphocytes. Anticancer Res. 1993, 13, 1007–1010.
125. Chew, B. P., Park, J. S., Carotenoid action on the immune response. J. Nutr. 2004, 134, 257S–261S.
126. Bendich, A., Shapiro, S. S., Effect of β-carotene and canthaxanthin on the immune responses of the rat. J. Nutr. 1986, 116, 2254–2262.
127. Prabhala, R. H., Maxey, V., Hicks, M. J., Watson, R. R., Enhancement of the expression of activation markers on human peripheral blood mononuclear cells by in vitro culture with retinoids and carotenoids. J. Leukoc. Biol. 1989, 45, 249–254.
128. Okai, Y., Higashi-Okai, K., Possible immunomodulating activities of carotenoids in in vitro cell culture experiments. Int. J. Immunopharmacol. 1996, 18, 753–758.
129. Bertram, J. S., Inhibition of chemically induced neoplastic transformation by carotenoids. Mechanistic studies. Ann. N. Y. Acad. Sci. 1993, 686, 161–175.
130. Daubrawa, F., Sies, H., Stahl, W., Astaxanthin diminishes gap junctional intercellular communication in primary human fibroblasts. J. Nutr. 2005, 135, 2507–2511.
131. Park, C. K., Ishimi, Y., Ohmura, M., Yamaguchi, M. et al., Vitamin A and carotenoids stimulate differentiation of mouse osteoblastic cells. J. Nutr. Sci. Vitaminol. (Tokyo). 1997, 43, 281–296.
132. Hanusch, M., Stahl, W., Schulz, W. A., Sies, H., Induction of gap junctional communication by 4-oxoretinoic acid generated from its precursor canthaxanthin. Arch. Biochem. Biophys. 1995, 317, 423–428.
133. Tanaka, T., Kawamori, T., Ohnishi, M., Makita, H. et al., Suppression of azoxymethane-induced rat colon carcinogenesis by dietary administration of naturally occurring xanthophylls astaxanthin and canthaxanthin during the postinitiation phase. Carcinogenesis 1995, 16, 2957–2963.
134. Bodendiek, S. B., Raman, G., Connexin modulators and their potential targets under the magnifying glass. Curr. Med. Chem. 2010, 17, 4191–230.
135. Teicher, V. B., Kucharski, N., Martin, H.-D., van der Saag, P. et al., Biological activities of apo-canthaxanthinoic acids related to gap junctional communication. Arch. Biochem. Biophys. 1999, 365, 150–155.
136. Pijnappel, W. W., Hendriks, H. F., Folkers, G. E., van den Brink, C. E. et al., The retinoid ligand 4-oxo-retinoic acid is a highly active modulator of positional specification. Nature 1993, 366, 340–344.
137. Zhang, L. X., Cooney, R. V, Bertram, J. S., Carotenoids up-regulate connexin43 gene expression independent of their provitamin A or antioxidant properties. Cancer Res. 1992, 52, 5707–5712.
138. Stahl, W., Nicolai, S., Briviba, K., Hanusch, M. et al., Biological activities of natural and synthetic carotenoids: induction of gap junctional communication and singlet oxygen quenching. Carcinogenesis 1997, 18, 89–92.
139. Miller, N. J., Sampson, J., Candeias, L. P., Bramley, P. M. et al., Antioxidant activities of carotenes and xanthophylls. FEBS Lett. 1996, 384, 240–242.
140. Bertram, J. S., Bortkiewicz, H., Dietary carotenoids inhibit neoplastic transformation and modulate gene expression in mouse and human cells. Am. J. Clin. Nutr. 1995, 62, 1327S–1336S.
141. Santa Cruz Biotechnologie, Canthaxanthin (CAS 514-78-3). http://www.scbio.de/datasheet-205617-canthaxanthin.html (accessed: February 2016)
142. FooDB, Showing compound canthaxanthin (FDB015890). http://foodb.ca/compounds/FDB015890 (accessed: July 2016)