The carotenoid pigment zeaxanthin - A review

Comprehensive Reviews in Food Science and Food Safety

Volumn 7, Issue 1, 2008, Pages 29-49

  Sajilata, M G ^a   Singhal, R S ^a   Kamat, M Y ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38749105855     PISSN: 15414337     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1541-4337.2007.00028.x     Document Type: Conference Paper

References (203)

1. Albrecht M, Misawa N, Sandmann G. 1999. Metabolic engineering of the terpenoid biosynthetic pathway of Escherichia coli for production of the carotenoids β-carotene and zeaxanthin. Biotechnol Lett 21 : 791 5.
2. Alcantara S, Sanchez S. 1999. Influence of carbon and nitrogen sources on Flavobacterium growth and zeaxanthin biosynthesis. J Ind Microb Biotechnol 23 : 697 700.
3. Aman R, Carle R, Conrad J, Beifuss U, Schieber A. 2005a. Isolation of carotenoids from plant materials and dietary supplements by high-speed counter-current chromatography. J Chrom A 1074 (1-2 99 105.
4. Aman R, Biehl J, Carle R, Conrad J, Beifuss U, Schieber A. 2005b. Application of HPLC coupled with DAD, APcI-MS and NMR to the analysis of lutein and zeaxanthin stereoisomers in thermally processed vegetables. Food Chem 92 (4 753 63.
5. Andrew Y, Britton G. 1990. Photobleaching in the unicellular green alga Dunaliella parva 19/9. Photosynth Res 25 : 129 36.
6. Armstrong GA. 1997. Genetics of eubacterial carotenoid biosynthesis: a colorful tale. Ann Rev Microbiol 51 : 629 59.
7. Ashton OB, Wong M, McGhie TK, Vather R, Wang Y, Requejo-Jackman C, Ramankutty P, Woolf AB. 2006. Pigments in avocado tissue and oil. J Agric Food Chem 54 (26 10151 8.
8. Asker D, Beppu T, Ueda K. 2007a. Zeaxanthinibacter enoshimensis gen. nov., sp. nov., a novel zeaxanthin-producing marine bacterium of the family Flavobacteriaceae, isolated from seawater off Enoshima Island, Japan. Int J Syst Evol Microbiol 57 (Pt 4 837 43.
9. Asker D, Beppu T, Ueda K. 2007b. Mesoflavibacter zeaxanthinifaciens gen. nov., sp. nov., a novel zeaxanthin-producing marine bacterium of the family Flavobacteriaceae. Sys App Microbiol 30 (4 291 6.
10. Bárzana E, Rubio D, Santamaría RI, García-Correa O, García F, Ridaura-Sanz VE, López-Munguía A. 2002. Enzyme-mediated solvent extraction of carotenoids from marigold flower (Tagetes erecta). J Agric Food Chem 50 : 4491 6.
11. Basu HH, Del Vecchio A. 2001. Encapsulated carotenoid preparations from high-carotenoid canola oil and cyclodextrins and their stability. J Am Oil Chem Soc 78 : 375 80.
12. th Intl. Congress on pigments in food, October 9-12, Hohenheim Univ., Stuttgart, Germany.
13. Ben-Amotz A, Katz A, Avron M. 1982. Accumulation of β-carotene in halotolerant algae: purification and characterization of b-carotene rich globules from Dunaliella bardawil (Chlorophyceae). J Phycol 18 : 529 37.
14. Benzie IF, Chung WY, Wang J, Richelle M, Bucheli P. 2006. Enhanced bioavailability of zeaxanthin in a milk-based formulation of wolfberry (Gou Qi Zi; Fructus barbarum L.). Br J Nutr 96 (1 154 60.
15. Berardo N, Brenna OV, Amato A, Valoti P, Pisacane V, Motto M. 2004. Carotenoids concentration among maize genotypes measured by near-infrared reflectance spectroscopy (NIRS). Innov Food Sci Emer Technol 5 (3 393 8.
16. Bernstein PS, Khachik F, Carvalho LS, Muir GJ, Zhao DY, Katz NB. 2001. Identification and quantitation of carotenoids and their metabolites in the tissues of the human eye. Exp Eye Res 72 : 215 23.
17. Berry A, Janssens D, Huembelin M, Jore JPM, Hoste B, Cleenwerck I, Vancanneyt M, Bretzel W, Mayer AF, Lopez-Ulibarri R, Shanmugam B, Swings J, Pasamontes L. 2003. Paracoccus zeaxanthinifaciens sp. nov., a zeaxanthin-producing bacterium. Int J Syst Evol Microbiol 53 : 231 8.
18. Bhosale P, Bernstein PS. 2004. β-Carotene production by Flavobacterium multivorum in the presence of inorganic salts and urea. J Ind Microbiol Biotechnol 31 : 565 71.
19. Bhosale P, Ermakov IV, Ermakova MR, Gellermann W, Bernstein PS. 2003. Resonant Raman quantification of zeaxanthin production from Flavobacterium multivorum. Biotechnol Lett 25 : 1007 11.
20. Bhosale P, Larson AJ, Bernstein PS. 2004. Factorial analysis of tricarboxylic acid cycle intermediates for optimization of zeaxanthin production from Flavobacterium multivorum. J Appl Microbiol 96 : 623 9.
21. Bishop NI., Urbig Y, Senger H. 1995. Complete separation of carotenoid biosynthesis by a unique mutation of the lycopene cyclase in the green alga, Senedesmus obliquus. FEBS Lett 367 : 158 62.
22. Block G, Patterson B, Subar A. 1992. Fruit, vegetables, and cancer prevention: a review of epidemiological evidence. Nutr Cancer 18 : 1 29.
23. Bochar DA, Friesen JA, Stauffacher CV, Rodwell VW. 1999. Biosynthesis of mevalonic acid from acetyl-CoA. In : Cane D, editor. The comprehensive natural product chemistry. Isoprenoids, including carotenoids and steroids. Vol. 2. Oxford, U.K. : Pergamon Press. p 15 44.
24. Boileau TWM, Moore AC, Erdman JW Jr. 1999. Carotenoids and vitamin A. In : Pappas AM, editor. Antioxidant status, diet, nutrition, and health. New York : CRC Press. p 133 58.
25. Bolliger HR, Konig A. 1969. In : Stahl E, editor. Thin-layer chromatography. New York : Springer-Verlag. p 259 311.
26. Bone RA, Landrum JT, Hime GW, Cains A, Zamor J. 1993. Stereochemistry of the human macular carotenoids. Invest Ophthal Vis Sci 34 : 2033 40.
27. Bone RA, Landrum JT, Friedes LM, Gomez CM, Kilburn MD, Menendez E, Vidal I, Wang W. 1997. Distribution of lutein and zeaxanthin stereoisomers in the human retina. Exp Eye Res 64 : 211 18.
28. Bone RA, Landrum JT, Cao Y, Howard AN, Alvarez-Calderon F. 2007. Macular pigment response to a supplement containing meso-zeaxanthin, lutein and zeaxanthin. Nut Met 4 : 12.
29. Borel P, Grolier P, Armand M, Partier A, LaFont H, Lairon D, Azais-Braesco V. 1996. Carotenoids in biological emulsions: solubility, surface-to-core distribution, and release from lipid droplets. J Lip Res 37 : 250 61.
30. Bowen PE, Herbst-Espinosa SM, Hussain EA. 2002. Esterification does not impair lutein bioavailability in humans. J Nutr 132 : 3668 73.
31. Breemen RB, Schmitz HH, Schwartz SJ. 1995. Fast atom bombardment tandem mass spectrometry of carotenoids. J Agric Food Chem 43 (2 384 9.
32. Breithaupt DE, Weller P, Wolters M, Hahn A. 2003. Plasma response to a single dose of dietary β-cryptoxanthin esters from papaya (Caiica papaya L.) or nonesterifed β-cryptoxanthin in adult human subjects: a comparative study. Br J Nutr 90 : 795 801.
33. Breithaupt DE, Weller P, Wolters M, Hahn A. 2004. Comparison of plasma responses in human subjects after the ingestion of 3R, 3R9-zeaxanthin dipalmitate from wolfberry (Lycium barbarum) and non-esterified 3R, 3R9-zeaxanthin using chiral high-performance liquid chromatography. Br J Nutr 91 : 707 13.
34. Britton G. 1976. Biosynthesis of carotenoids. In : Goodwin TW, editor. Chemistry and biochemistry of plant pigments. New York : Academic Press. p 304 5.
35. Britton G. 1985. General carotenoids methods. Method Enzymol 3 : 113 49.
36. Britton G. 1991. Carotenoids. Methods Plant Biochem 7 : 473 518.
37. Britton G. 1995. Structure and properties of carotenoids in relation to function. FASEB J 9 : 1551 8.
38. Bushway RJ. 1985. Separation of carotenoids in fruits and vegetables by high performance liquid chromatography. J Liq Chrom 8 : 1527 47.
39. Castenmiller JJM, West CE. 1998. Bioavailability and bioconversion of carotenoids. Ann Rev Nutr 18 : 19 38.
40. Chen F, Li HB, Wong RN, Ji B, Jiang Y. 2005. Isolation and purification of the bioactive carotenoid zeaxanthin from the microalga Microcystis aeruginosa by high-speed counter-current chromatography. J Chromatogr A 1064 (2 183 6.
41. Cheng CY, Chung WY, Szeto YT, Benzie IF. 2005. Fasting plasma zeaxanthin response to Fructus barbarum L. (wolfberry; Kei Tze) in a food-based human supplementation trial. Brit J Nut 93 (1 123 30.
42. Chiralt A, Casas A, Primo YE. 1990. Carotenoid pigments of Viburnum tinus L. leaves. Revista de Agroquimica y Tecnologia de Alimentos 30 (4 454 60.
43. Chitchumroonchokchai C, Failla ML. 2006. Hydrolysis of zeaxanthin esters by carboxyl ester lipase during digestion facilitates micellarization and uptake of the xanthophyll by Caco-2 human intestinal cells. J Nut 136 (3 588 94.
44. Chitchumroonchokchai C, Schwartz SJ, Failla ML. 2004. Assessment of lutein bioavailability from meals and supplement using simulated digestion and Caco-2 human intestinal cells. J Nutr 134 : 2280 6.
45. Craft NE. 1992. Carotenoid reversed-phase high performance liquid chromatography methods: reference compendium. Methods Enzymol 213 : 185 205.
46. Craft NE, Sander LC, Pierson HF. 1990. Separation and relative distribution of all-trans-β-carotene and its cis isomers in ß-carotene preparations. J Micronutr Anal 8 : 209 21.
47. Craft NE, Wise SA, Soares JH Jr. 1992. Optimization of an isocratic high-performance liquid chromatographic separation of carotenoids. J Chromatogr 589 : 171 6.
48. Creemers AFL, Kuehne S, Bovee-Geurts PHM, de Grip WJ, Lugtenburg J, de Groot HJM. 2002. 1H and 13C MAS NMR evidence for pronounced ligand-protein interactions involving the ionone ring of the retinylidene chromophore of rhodopsin. Proc Natl Acad Sci USA 99 (14 9101 6.
49. Daood HG, Biacs P, Czinkotai B, Hoschke A. 1992. Chromatographic investigation of carotenoids, sugars and organic acids from Diospyros kaki fruits. Food Chem 45 (2 151 5.
50. Dasek J, Sheperd D, Traelnes RK. 1973. Proced de production de zeaxanthine. Belgium patent 790289.
51. Davies BH. 1976. Carotenoids. In : Goodwin TW, editor. Chemistry and biochemistry of palnt pigments. 2nd ed. London, U.K. : Academic Press. 38 p.
52. Davies BH, Hsu WJ, Chicester CO. 1970a. The mechanism of the conversion of beta-carotene into canthaxanthin by the brine shrimp, Artemia salina L. (Crustacea: Branchiopoda). Comp Biochem Physiol 33 (3 601 15.
53. Davies BH, Matthews S, Kirk JTO. 1970b. The nature and biosynthesis of the carotenoids of different colour varieties of Capsicum annum. Phytochem 9 : 797 805.
54. Delgado-Vargas F, Paredes-López O. 1997. Effects of enzymatic treatments of marigold flowers on lutein isomeric profiles. J Agric Food Chem 45 : 1097 102.
55. Deming DM, Erdman JW. 1999. Mammalian carotenoid absorption and metabolism. Pure Appl Chem 71 (12 2213 23.
56. Demmig-Adams B. 1990. Carotenoids and photoprotection in plants: a role for the xanthophyll zeaxanthin. Biochim Biophys Acta 1020 : 1 24.
57. Demmig-Adams B, Adams WW. 1992. Photoprotection and other responses of plants to high light stress. Ann Rev Plant Physiol Plant Mol Biol 43 : 599 626.
58. Demmig-Adams B, Gilmore AM, Adams WW. 1996. Carotenoids 3: in vivo function of carotenoids in higher plants. FASEB J 10 : 403 12.
59. Edwards MF. 1985. A review of liquid mixing equipment. In : Harnby N, Edwards MF, Nienow AW, editors. Mixing in the process industries. London, U.K. : Butterworths and Co. p 115 8.
60. Eisenreich W, Bacher A, Berry A, Bretzel W, Humbelin M, Lopez-Ulibarri R, Mayer AF, Yeliseev A. 2002. Biosynthesis of zeaxanthin via mevalonate in Paracoccus species strain PTA-3335. A product-based retrobiosynthetic study. J Org Chem 67 : 871 5.
61. Emenhiser C, Sander LC, Schwartz SJ. 1995. Capability of a polymeric C30 stationary phase to resolve cis-trans carotenoid isomers in reversed-phase liquid chromatography. J Chrom A 707 : 205 16.
62. Emenhiser C, Englert G, Sander LC. 1996. Isolation and structural elucidation of the predominant geometrical isomers of α-carotene. J Chrom A 719 : 333 43.
63. Eonseon J, Polle JW, Lee HK, Hyun SM, Chang MJ. 2003. Xanthophylls in microalgae: from biosynthesis to biotechnological mass production and application. Microbiol Biotechnol 13 (2 165 74.
64. Epler KS, Sander LC, Ziegler RG. 1992. Evaluation of reversed-phase liquid chromatographic columns for recovery and selectivity of selected carotenoids. J Chrom 595 : 89 101.
65. Erdman, JW Jr., Bierer TL, Gugger ET. 1993. Absorption and transport of carotenoids. Ann N Y Acad Sci 691 : 76 85.
66. Ernst H. 2002. Recent advances in industrial carotenoid synthesis. Pure Appl Chem 74 : 1369 82.
67. Euler HV, Karrer P, Klussmann E, Morf R. 1930. Helv Chim Acta 15 : 502.
68. 2 extraction of carotene and lutein from leaf protein concentrates. J Food Sci 53 : 1532 6.
69. Gama JJT, Sylos CM. 2005. Major carotenoid composition of Brazilian Valencia orange juice: identification and quantification by HPLC. Food Res Int 38 (8-9 899 903.
70. Garnett KM, Gierhart DL, Guerra-Santos LH, inventors; Garnett and others (1998): assignee, Applied Food Biotechnology Inc., date of issue Dec 29 1998. Method of making pure 3R-3′R stereoisomer of zeaxanthin for human ingestion. U.S. patent 5,854,015.
71. Gartner C, Stahl W, Sies H. 1996. Preferential increase in chylomicron levels of the xanthophylls lutein and zeaxanthin compared with β-carotene in the human. Int J Vit Nutr Res 66 : 119 25.
72. Gierhart DL, inventor; Gierhart (1994): assignee, Applied Food Biotechnology Inc., date of issue May 3 1994. Production of zeaxanthin and zeaxanthin-containing compositions. U.S. patent 5,308,759.
73. Gierhart DL, inventor; Gierhart (1995): assignee, Applied Food Biotechnology Inc., date of issue June 27 1995. Zeaxanthin-containing compositions produced by Flavobacterium multivorum. U.S. patent 5,427,783.
74. Gill D, Lponen RG, Rimai L. 1970. Resonance Raman scattering of laser radiation by vibrational modes of carotenoid pigment molecules in intact plant tissues. Nature 227 : 743 4.
75. Giraudat J, Parcy F, Bertauche N, Gosti F, Leung J, Morris PC, Bouvier-Durand M, Vartanian N. 1994. Current advances in abscisic acid action and signalling. Plant Mol Biol 26 : 1557 77.
76. Goodwin TW. 1971. Carotenoid biosynthesis. In : Krinsky NI, Mathews-Roth MM, Taylor RF, editors. Carotenoids chemistry and biology. New York : Plenum Press. p 167 85.
77. Goodwin TW. 1976. Distribution of carotenoids. In : Goodwin TW, editor. Chemistry and biochemistry of plant pigments. New York : Academic Press Inc. p 225 61.
78. Grossman AR, Bhaya D, Apt KE, Kehoe DM. 1995. Light-harvesting complexes in oxygenic photosynthesis: diversity, control, and evolution. Ann Rev Genet 29 : 231 88.
79. Guerro-Santos, Luis H, Greenbury DK, inventors; Guerro-Santos and others (2005): assignee Zeavision LLC, date of issue Aug 30, 2005. Microcrystalline zeaxanthin with high bioavailability in oily carrier formulations. U.S. patent 6,936,279.
80. Guillou A, Choubert G, Noue J. 1993. Separation and determination of carotenoids, retinol, retinal, and their dehydro forms by isocratic reversed-phase HPLC. Food Chem 47 (1 93 9.
81. Hadden WL, Watkins RH, Levy LW, Regalado E, Rivadeneira DM, van Breemen RB, Schwartz SJ. 1999. Carotenoid composition of marigold (Tagetes erecta) flower extract used as nutritional supplement. J Agric Food Chem 47 : 4189 94.
82. Hager A. 1980. The reversible, light-induced conversions of xanthophylls in the chloroplast. In : Czygan FC, editor. Pigments in plants. Stuttgart : Fischer. p 57 79.
83. Hager A, Holocher K. 1994. Localization of the xanthophyll-cycle enzyme violaxanthin de-epoxidase within the thylakoid lumen and abolition of its mobility by a (light dependent) pH decrease. Planta 192 : 581 9.
84. Hamilton PB, Tirado FJ, Garcia-Hernandez F. 1990. Deposition in egg yolks of the carotenoids from saponified and unsaponified oleoresin of red pepper (Capsicum annuum) fed to laying hens. Poult Sci 69 (3 462 70.
85. Han O, Mudgett RE. 1992. Effects of oxygen and carbon dioxide partial pressure on monascus growth and pigment production in solid-state fermentations. Biotechnol Prog 8 : 5 10.
86. Handelman GJ, Dratz EA, Reay CC, Kuijk FJGM. 1988. Carotenoids in human macula and whole retina. Invest Opthalmol Vis Sci 29 : 850 55.
87. Handelman GJ, Shen B, Krinsky NI. 1991. High-resolution analysis of carotenoids in human plasma by high-performance liquid chromatography. Methods Enzymol 213 : 336 46.
88. Handelman GJ, Nightingale ZD, Lichtenstein AH, Schaefer EJ, Blumberg JB. 1999. Lutein and zeaxanthin concentrations in plasma after dietary supplementation with egg yolk. Am J Clin Nutr 70 : 247 51.
89. Hao Z, Parker B, Knapp M, Yu L. 2005. Simultaneous quantification of alpha-tocopherol and four major carotenoids in botanical materials by normal phase liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry. J Chrom A 1094 (1-2 83 90.
90. Heacock PM, Hertzler SR, Wolf B. 2004. The glycemic, insulinemic, and breath hydrogen responses in humans to a food starch esterified by 1-octenyl succinic anhydride. Nutr Res 24 : 581 92.
91. Hoshino T, Ojima K, Setoguchi Y. 2004. Production of zeaxanthin by recombinant Phaffia rhodozyma strain. PCT Int Appl 20030923.
92. Human Nutrition Information Service. 1989. US Dept. of Agriculture. Composition of foods. Agriculture handbook no. 8, supplement no. 8. Washington, D.C. : U.S. Government Printing Office.
93. Humphries JM, Khachik F. 2003. Distribution of lutein, zeaxanthin, and related geometrical isomers in fruit, vegetables, wheat, and pasta products. J Agric Food Chem 51 : 1322 7.
94. Hundle BS, O'Brien DA, Alberti M, Beyer P, Hearst JE. 1992. Functional expression of zeaxanthin glucosyltransferase from Erwinia herbicola and a proposed uridine diphosphate binding site. Proc Natl Acad Sci USA 89 (19 9321 25.
95. Hurry V, Andersson JM, Chow WS, Osmond CB. 1997. Accumulation of zeaxanthin in abscicic acid-deficient mutants of Arabidopsis does not affect chlorophyll quenching or sensitivity to photoinhibition in vivo. Plant Physiol 113 : 639 48.
96. Isler O, Lindlar H, Montavon M, Ruegg R, Saucy G, Zeller P. 1956a. Synthetic colorants as food dyes. Mitt Lebensmitteluntersuchung Hyg 47 (3 183 90.
97. Isler O, Montavon M, Rüegg R, Saucy G, Zeller P. 1956b. Synthese hydroxyhaltiger Carotenoide. Vehr Naturforsch Ges Basel 67 : 379 91.
98. Jewell VC, Northrop-Clewes CA, Tubman R, Thurnham DI. 2001. Nutritional factors and visual function in premature infants. Proc Nutr Soc 60 : 171 8.
99. Jewell VC, Mayes CB, Tubman TR, Northrop-Clewes CA, Thurnham DI. 2004. A comparison of lutein and zeaxanthin concentrations in formula and human milk samples from Northern Ireland mothers. Eur J Clin Nutr 58 : 90 7.
100. Jin ES, Polle JWE, Melis A. 2001. Involvement of zeaxanthin and of the Cbr protein in the repair of photosystem-II from photoinhibition in the green alga Dunaliella salina. Biochim Biophys Acta 1506 : 244 59.
101. Jin ES, Feth B, Melis A. 2003. A mutant of the green alga Dunaliella salina constitutively accumulates zeaxanthin under all growth conditions. Biotech Bioeng 81 : 115 24.
102. 2 extraction of corn yellow pigment. Food Sci 25 (9 125 8.
103. Johnson EA, Schroeder WA. 1996. Microbial carotenoids. Adv Biochem Eng/Biotech 53 : 119 78.
104. Johnson EJ, Russell RM. 1992. Distribution of orally administered beta-carotene among lipoproteins in healthy men. Am J Clin Nutr 56 : 128 35.
105. Jungalwala FB, Cama HR. 1962. Carotenoids in Delonix regia (Gul Mohr) flower. Biochem J 85 : 1 8.
106. Jurgens UJ, Weckesser J. 1985. Carotenoid-containing outer membrane of Synechocystis sp. strain PCC6714. J Bacteriol 164 (1 384 9.
107. Justyna M, Gruszecki WI. 2005. Heat-induced and light-induced isomerization of the xanthophyll pigment zeaxanthin. J Photochem Photobiol B: Biology 80 : 178 86.
108. Keri L, Carpenter H, Veen C, Hird R, Dennis IF, Ding T, Mitchinson MJ. 1997. The carotenoids β-carotene, canthaxanthin and zeaxanthin inhibit macrophage-mediated LDL oxidation. FEBS 18094 FEBS Lett 401 : 262 6.
109. Khachik F, inventor 2005. Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants. U.S. patent 6,262,284.
110. Khachik F, Beecher GR, Lusby WR. 1989. Separation, identification, and quantification of the major carotenoids in extracts of apricots, peaches, cantaloupe and pink grapefruit by liquid chromatography. J Agric Food Chem 37 (6 1465 73.
111. Khachik F, Beecher GR, Goli MB, Lusby WR. 1991. Separation, identification and quantification of carotenoids in fruits, vegetables and human plasma by high performance liquid chromatography. Pure Appl Chem 63 : 71 80.
112. Khachik F, Askin FB, Lai K. 1998. Distribution, bioavailability, and metabolism of carotenoids in humans. In : Bidlack WR, Omaye ST, Meskin MS, Jahner D, editors. Phytochemicals, a new paradigm. Lancaster, Pa. : Technomic Publishing. p 77 96.
113. Khachik F, de Moura FF, Zhao D, Aebischer CP, Bernstein PS. 2002. Transformations of selected carotenoids in plasma, liver, and ocular tissues of humans and in non-primate animal models. Invest Ophthalmol Vis Sci 43 (11 3383 92.
114. Kim S, Park J, Hwang IK. 2004. Composition of main carotenoids in Korean red pepper (Capsicum annuum L.) and changes of pigment stability during the drying and storage process. J Food Sci 69 (1 C39 44.
115. Koenig-Grillo S. 2002. Technical documentation lutein 5% TG and zeaxanthin 5% TG in food. Unpublished technical Roche Vitamins Ltd report, Theme 6007, November 22, 1-21, cited in Zeaxanthin CTA submitted by DSM Nutritional Products Ltd.
116. Kopsell DA, Kopsell DE. 2006. Accumulation and bioavailability of dietary carotenoids in vegetable crops. Trends Plant Sci 11 (10 499 507.
117. Kuhn R, Wiegund W. 1929 Ober Konjugierte Dopplebindungen. IX. Der Farbstoff der Juderkircshen (Physalis alkekengi und Physalis franchetti). 1929. Helv Chim Acta 12 : 499 506.
118. Lagarde D, Beuf L, Vermaas W. 2000. Increased production of zeaxanthin and other pigments by application of genetic engineering techniques to Synechocystis sp. strain PCC 6803. Appl Environ Microbiol 66 : 64 72.
119. Lee HS, Coates GA. 2003. Effect of thermal pasteurisation on Valencia orange juice colour and pigments. Leben Wissen Technol 36 (1 153 6.
120. Lesellier E, Marty C, Berset C, Tchapla A. 1989. Optimization of the isocratic non-aqueous reverse phase (NARP) HPLC separation of trans cis-α- and β-carotenes. J High Resolut Chromatogr 12 : 447 54.
121. Liaaen-Jensen S. 1971. Isolation, reactions. In : Isler O, editor. Carotenoids. Bassel: Birkhauser-Verlag. p 61 179.
122. Liao HH, Medwid RD, Heefner DL, Sniff KS, Hassler RA, Yarus MJ, inventors 1995. Carotenoid producing culture using Nespongiococcum excentricum. U.S. patent 5,437,997.
123. Liao WL, Nur-E-Borhan SA, Okada S, Matsui T, Yamaguchi K. 1993. Pigmentation of cultured black tiger prawn by feeding with a Spirulina supplemented diet. Nippon Suisan Gakkaishi/Bull Japan Soc Sci Fisher 59 : 165 9.
124. Loeber DE, Russel SW, Toube TP, Weedon BCL, Diment J. 1971. Carotenoids and related compounds. Part XXVIII. l. Synthesis of zeaxanthin, β-cryptoxanthin, and zeinoxanthin (α-cryptoxanthin). J Chem Soc (C 404 8.
125. Lu YJ, Yao HY, Gong YS, Sheng QK. 2005. Effects of enzymatic treatment of corn gluten meal on lutein and zeaxanthin extraction. Int J Food Prop 8 (1 161 9.
126. Manach C, Williamson G, Morand C, Scalbert A, Remesy C. 2005. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr 81 : 230S 42S.
127. Marin E, Nussaume L, Quesada A, Gonneau M, Sotta B, Hugueney P, Frey A, Marion-Poll A. 1996. Molecular identification of zeaxanthin epoxidase of Nicotiana plumbaginifolia, a gene involved in absicic acid biosynthesis and corresponding to ABA locus of Arabidopsis thaliana. EMBO J 15 : 2331 42.
128. Masetto A, Flores-Cotera LB, Diaz C, Langley E, Sanchez S. 2001. Application of a complete factorial design for the production of zeaxanthin by Flavobacterium sp. J Biosci Bioeng 92 : 55 8.
129. McDermott JCB, Brown DJ, Britton G, Goodwin TW. 1974. Alternative pathways of zeaxantin biosynthesis in a Flavobacterium species. Biochem J 144 : 231 43.
130. Miebach EM, Behsnilian D. 2006. Stability and bioavailability of lycopene, lutein and zeaxanthin in fruits and vegetables as affected by thermal processing. Stewart Postharv Rev 5 : 124 33.
131. Milanowska J, Gruszecki WI. 2005. Heat-induced and light-induced isomerization of the xanthophyll pigment zeaxanthin. J Photochem Photobiol B-Biol 80 (3 178 86.
132. Misawa N, Shimada H. 1998. Metabolic engineering for the production of carotenoids in non-carotenogenic bacteria and yeast. J Biotechnol 59 : 169 81.
133. Misawa N, Kajiwara S, Kondo K, Yokoyama A, Satomi Y. 1995a. Canthaxanthin biosynthesis by the conversion of methylene to keto groups in a hydrocarbon carotene by a single gene. Biochem Biophys Res Commun 209 : 867 76.
134. Misawa N, Satomi Y, Kondo K, Yokoyama A, Kajiwara S. 1995b. Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level. J Bacteriol 177 : 6575 84.
135. Moeller SM, Jacques PF, Blumberg JB. 2000. The potential role of dietary xanthophylls in cataract and age-related macular degeneration. J Am Coll Nutr 5 : 522 7.
136. Mohamed A, Jansson C. 1989. Influence of light on accumulation of photosynthesis-specific transcripts in the cyanobacterium Synechocystis 6803. Mol Gen Genet 238 : 161 8.
137. Moros EE, Darnoko D, Cheryan M, Perkins EG, Jerrell J. 2002. Analysis of xanthophylls in corn by HPLC. J Agric Food Chem 50 : 5787 90.
138. Murata N, Sato N, Omata T, Kuwabara T. 1981. Separation and characterization of thylakoid and cell envelope of the blue-green alga (cyanobacterium) Anacystis nidulans. Plant Cell Physiol 22 (5 855 66.
139. 2 and the effect of solvent modifiers. J Agric Food Chem 48 : 5640 2.
140. Neill SJ, Horgan R, Parry AD. 1986. The carotenoid and abscisic acid content of viviparous kernels and seedlings of Zea mays L. Planta 169 : 87 96.
141. Nelis JH, DeLeenheer PA. 1989. Fat-soluble vitamins and pigments. In : Vandamme JE editor. Biotechnology of vitamins, pigments and growth factors. London, New York : Elsevier Applied Science. p 43 62.
142. Nelis JH, DeLeenheer PA. 1991. Microbial sources of carotenoid pigments used in foods and feeds. J Appl Bacteriol 70 : 181 91.
143. Nishino H, Tokuda H, Satomi Y, Masuda M, Bu P, Onozuka M, Yamaguchi S, Okuda Y, Takayasu J, Tsuruta J, Okuda M, Ichiishi E, Murakoshi M, Kato T, Misawa N, Narisawa T, Takasuka N, Yano M. 1999. Cancer prevention by carotenoids. Pure Appl Chem 71 (12 2273 8.
144. Niyogi KK, Björkman O, Grossman AR. 1997. Chlamydomonas xanthophyll cycle mutants identified by video imaging of chlorophyll fluorescence quenching. Plant Cell 9 : 1369 80.
145. Olson JA. 1994. Absorption, transport, and metabolism of carotenoids in humans. Pure Appl Chem 66 (5 1011 6.
146. Orndorff SA, Campbell EA, Medwid RD, inventors 1994. Zeaxanthin producing strains of Neospongiococcum excentricum. U.S. patent 5,360,730.
147. Palermo JA, Gros EG, Seldes AM. 1991. Carotenoids from three red algae of the Corallinaceae. Phytochem 30 (9 2983 6.
148. Panfili G, Fratianni A, Irano M. 2004. Improved normal-phase high-performance liquid chromatography procedure for the determination of carotenoids in cereals. J Agric Food Chem 52 (21 6373 7.
149. Parada J, Aguilera JM. 2007. Food microstructure affects the bioavailability of several nutrients. J Food Sci 72 (2 R21 R32.
150. Parker RS. 1996. Absorption, metabolism, and transport of carotenoids. FASEB J 10 : 542 51.
151. Parry J, Lan S, Luther M, Kequan Z, Yurawecz MP, Whittaker P, Liangli Y. 2005. Fatty acid composition and antioxidant properties of cold-pressed marionberry, boysenberry, red raspberry, and blueberry seed oils. J Agric Food Chem 53 (3 566 73.
152. Pasamontes L, Hug D, Tessier M, Hohmann HP, Schierle J, van Loon AP. 1997. Isolation and characterization of the carotenoid biosynthesis genes of Flavobacterium sp. strain R1534. Gene 185 : 35 41.
153. Pateau I, Khachik F, Brown ED, Beecher GR, Kramer TR, Chittams J, Clevidence BA. 1998. Chronic ingestion of lycopene-rich tomato juice or lycopene supplements significantly increases plasma concentrations of lycopene and related tomato carotenoids in humans. Am J Clin Nut 68 : 1187 95.
154. Peng Y, Ma C, Li Y, Leung SYK, Jiang ZH Zhao Z. 2005. Quantification of zeaxanthin dipalmitate and total carotenoids in lycium fruits (Fructus lycii). Plant Foods Hum Nut 60 (4 161 4.
155. Perez-Galvez A, Martin HD, Sies H, Wilhelm S. 2003. Incorporation of carotenoids from paprika oleoresin into human chylomicrons. Brit J Nutr 89 (6 787 93.
156. Perez-Galvez A, Hornero-Mendez D, Minguez-Mosquera MI. 2004. Changes in the carotenoid metabolism of capsicum fruit during application of modified slow drying process for paprika production. J Agric Food Chem 52 (3 518 22.
157. Quackenbush FW, Smallidge RL 1986. Nonaqueous reverse-phase liquid chromatographic system for separation and quantitation of provitamins A. J Assoc Off Anal Chem 69 : 767 72.
158. Rao AV, Agarwal S. 1999. Role of lycopene as antioxidant carotenoid in the prevention of chronic diseases: a review. Nutr Res 19 : 305 23.
159. Richelle M, Bortlik K, Liardet S, Hager C, Lambelet P, Baur M, Applegate LA, Offord EA. 2002. A food-based formulation provides lycopene with the same bioavailability to humans as that from tomato paste. J Nutr 132 : 404 8.
160. Rivas J, Abadia A, Abadia JA. 1989. New reversed phase-HPLC method resolving all major higher plant photosynthetic pigments. Plant Physiol 91 : 190 2.
161. Rock CD, Zeevaart JAD. 1991. The aba mutant of Arabidopsis thaliana is impaired in epoxy-carotenoid biosynthesis. Proc Natl Acad Sci U S A 88 : 7496 9.
162. Rock CD, Bowlby NR, Hoffmann-Benning S, Zeevaart JAD. 1992. The aba mutant of Arabidopsis thaliana (L.) Heynh has reduced chlorophyll fluorescence yields and reduced thylakoid stacking. Plant Physiol 100 : 1796 801.
163. Rock CL, Jacob RA, Bowen PE. 1994. Update on the biological characteristics of the antioxidant micronutrients: vitamin C, vitamin E and the carotenoids. J Am Diet Assn 96 : 693 702.
164. Rodriguez-Amaya DB. 2001. General procedure and sources of errors in carotenoid analysis. In : A guide to carotenoid analysis in foods. Intl. Life Sciences Inst. Washington, D.C. : ILSI Press. 23 p.
165. Rodriguez-Huezo ME, Pedroza-Islas R, Prado-Barragan LA, Beristain CI., Vernon-Carter EJ. 2004. Microencapsulation by spray-drying of multiple emulsions containing carotenoids. J Food Sci 69 : E351 E9.
166. Rohmer M, Knani M, Simonin P, Sutter B, Sahm H. 1993. Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem J 295 : 517 24.
167. Romanchik JE, Morel DW, Harrison EH. 1995. Distributions of carotenoids and α-tocopherol among lipoproteins do not change when human plasma is incubated in vitro. J Nutr 125 : 2610 7.
168. Römer S, Lübeck J, Kauder F, Steiger S, Adomat C, Sandmann G. 2002. Genetic engineering of a zeaxanthin-rich potato by antisense inactivation and co-suppression of carotenoid epoxidation. Met Eng 4 (4 263 72.
169. Ruther A, Misawa N, Boger P, Sandmann G. 1997. Production of zeaxanthin in Escherichia coli transformed with different carotenogenic plasmids. Appl Microbiol Biotechnol 48 : 162 7.
170. Sander LC, Craft NE. 1990. Device for subambient temperature control in liquid chromatography. Anal Chem 62 : 1545 7.
171. Scheiber A, Carle R. 2005. Occurrence of carotenoid cis-isomers in foods: technological, analytical, and nutritional implications. Trends Food Sci Technol 16 : 416 22.
172. Schiedt K, Englert G, Noack K, Vecchi M, Leuenberger FJ. 1981. 6th Int. Symp. Carotenoids, Liverpool.
173. Schlatterer J, Breithaupt DE. 2006. Xanthophylls in commercial egg yolks: quantification and identification by HPLC and LC-(APCI) MS using a C30 phase. J Agric Food Chem 54 (6 2267 73.
174. Schocher AJ, Wiss O, inventors; Schocher and Wiss (1975): assignee Hoffman LaRoche, date of issue June 24 1975. Process for the manufacture of zeaxanthin. U.S. patent 3,891,504.
175. Scholz TA, Hata TR, Pershing LK, Gellermann W, McClane R, Alexeeva M, Irmakov I, Khachik F. 2000. Non-invasive Raman spectroscopic detection of carotenoids in human skin. J Invest Dermatol 115 : 441 8.
176. Scott KJ, Hart DJ. 1993. Further observations on problems associated with the analysis of carotenoids by HPLC - 2: Column temperature. Food Chem 47 : 403 5.
177. Selim K, Tsimidou M, Biliaderis CG. 2000. Kinetic studies of degradation of saffron carotenoids encapsulated in amorphous polymer matrices. Food Chem 71 : 199 206.
178. Shepherd D, Dasek J, Suzanne M, Carel S, inventors; Shepherd and others (1976): assignee Societe D' Assistance Technique pour Produits Nestle S.A. (Lausanne, CH), date of issue April 20 1976. Production of zeaxanthin. U.S. patent 3,951,743.
179. Shlomai P, Ben-Amotz A, Margalith P, Mokady S. 1992. Utilization of a natural β-carotene stereoisomers mixture from the fungus
180. Smith CG, Johnson MJ. 1958. Aeration requirements for the growth of aerobic organisms. J Bacteriol 68 : 346 50.
181. Snodderly DM. 1995. Evidence for protection against age-related macular degeneration by carotenoids and antioxidant vitamins. Am J Clin Nutr 62 (Suppl 1448S 61S.
182. Soukup M, Spurr P, Widmer E. 1996. Strategies for building the carbon skeleton. In : Britton G, Liaaen-Jenxdn S, Pfander H, editors. Carotenoids, vol. 2, synthesis. Basel : Birkhäuser. p 7 14.
183. Steinmetz KA, Potter JD. 1993. Food-group consumption and colon cancer in the Adelaide case-control study. Int J Cancer 53 : 711 9.
184. Sujak A, Gabrielska J, Grudziski W, Borc R, Mazurek P, Gruszecki WI. 1999. Lutein and zeaxanthin as protectors of lipid membranes against oxidative damage: the structural aspects. Arch Biochem Biophys 371 (2 301 7.
185. Tardy F, Havaux M. 1996. Photosynthesis, chlorophyll fluorescence, light-harvesting system and photoinhibition resistance of a zeaxanthin- accumulating mutant of Arabidopsis thaliana. J Photochem Photobiol B Biol 34 : 87 94.
186. Thomson LR, Toyoda Y, Langner A, Delori FC, Garnett KM, Craft N, Nichols CR, Cheng KM, Dorey CK. 2002. Elevated retinal zeaxanthin and prevention of light-induced photoreceptor cell death in quail. Invest Ophthalmol Vis Sci 43 (11 3538 49.
187. Topuz A, Ozdemir F. 2003. Influences of γ-irradiation and storage on the carotenoids of sun-dried and dehydrated paprika. J Agric Food Chem 51 (17 4972 7.
188. Toyomizu M, Sato K, Taroda H, Kato T. Akiba Y. 2001. Effects of dietary of Spirulina on meat color muscle of broiler chickens. Br Poult Sci 42 : 197 202.
189. Updike AA, Schwartz SJ. 2003. Thermal processing of vegetables increases cis isomers of lutein and zeaxanthin. J Agric Food Chem 51 : 6184 90.
190. van het Hof KH, Tijburg LB, Pietrzik K, Weststrate JA. 1999. Influence of feeding different vegetables on plasma levels of carotenoids, folate and vitamin C. Effect of disruption of the vegetable matrix. Brit J Nutr 82 : 203 12.
191. van Het Hof KH, West CE, Weststrate JA, Hautvast JG. 2000a. Dietary factors that affect the bioavailability of carotenoids. J Nutr 130 : 503 6.
192. van het Hof KH, de Boer BC, Tijburg LB, Lucius BR, Zijp I, West CE, Hautvast JG, Weststrate JA. 2000b. Carotenoid bioavailability in human from tomatoes processed in different ways determined from the carotenoid response in the triglyceride-rich lipoprotein fraction of plasma after a single consumption and in plasma after four days of consumption. J Nutr 130 : 1189 96.
193. Verwei M, Arkbage K, Groten JP, Witthoft C, van den Berg H, Havenaar R. 2005. The effect of folate-binding proteins on bioavailability of folate from milk products. Trends Food Sci Tech 16 : 307 10.
194. Walton DC, Li Y. 1995. Abscisic acid biosynthesis and metabolism. In : Davies PJ, editor. Plant hormones. Dordrecht, the Netherlands : Kluwer Academic Publishers. p 140 57.
195. Widmer E, Soukup M, Zell R, Broger E, Wagner HP, Imfeld M. 1990. Technical procedures for the synthesis of carotenoids and related compounds from 6-oxo-isophorone: syntheses of (3R, 3′R)-zeaxanthin. Helv Chim Acta 73 : 861 8.
196. Wingerath T, Stahl W, Sies H. 1995. β-cryptoxanthin selectively increased in human chylomicrons upon ingestion of tangerine concentrate rich β-cryptoxanthin esters. Arch Biochem Biophys 324 : 385 90.
197. Wingerath T, Stahl W, Kirsch D, Kaufmann R, Sies H. 1996. Fruit juice carotenol fatty acid esters and carotenoids as identified by matrix-assisted laser desorption ionization (MALDI) mass spectrometry. J Agric Food Chem 44 (8 2006 13.
198. Withers NW, Alberte RS, Lewin RA, Thornber JP, Britton G, Goodwin TW. 1978. Photosynthetic unit size, carotenoids, and chlorophyll-protein composition of Prochloron sp., a prokaryotic green alga. Proc Natl Acad Sci U S A 75 : 2301 5.
199. Yeum K, Russell RM. 2002. Carotenoid bioavailability and bioconversion. Ann Rev Nutr 22 : 483 504.
200. Yeum KJ, Shang FM, Schalch WM. 1999. Fat-soluble nutrient concentrations in different layers of human cataractous lens. Curr Eye Res 19 : 502 5.
201. Zeevaart JAD, Creelman RA. 1988. Metabolism and physiology of abscisic acid. Ann Rev Plant Physiol Plant Mol Biol 39 : 439 73.
202. Zhou L, Leung I, Tso MO, Lam KW. 1999. The identification of dipalmityl zeaxanthin as the major carotenoid in Gou Qi Zi by high pressure liquid chromatography and mass spectrometry. J Ocul Pharmacol Ther 15 : 557 65.
203. Zuber MS, Darrah LL. 1987. Breeding, genetics and seed corn production. In : Watson, SA, Ramstad P, editors. Corn: chemistry and technology. St. Paul, Minn. : American Assn of Cereal Chemists. p 31 51.