Enzymatic formation of apo-carotenoids from the xanthophyll carotenoids lutein, zeaxanthin and β-cryptoxanthin by ferret carotene-9′, 10′-monooxygenase

Archives of Biochemistry and Biophysics

Volumn 506, Issue 1, 2011, Pages 109-121

  Mein, Jonathan R ^a   Dolnikowski, Gregory G ^a   Ernst, Hansgeorg ^b   Russell, Robert M ^a   Wang, Xiang Dong ^a  

^a TUFTS UNIVERSITY   (United States)

^b BASF SE   (Germany)

Author keywords

Apo carotenoid; CMO1; CMO2; Metabolism; Xanthophyll

Indexed keywords

3 OH ALPHA APO 10' CAROTENAL; 3 OH ALPHA IONONE; 3 OH BETA APO 10' CAROTENAL; 3 OH BETA IONONE; BETA APO 10' CAROTENAL; BETA CRYPTOXANTHIN; BETA IONONE; CAROTENE; CAROTENE 9',10' MONOOXYGENASE; CAROTENOID; UNCLASSIFIED DRUG; XANTHOPHYLL; ZEAXANTHIN;

ARTICLE; BACULOVIRUS EXPRESSION SYSTEM; CHEMICAL BOND; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME METABOLISM; ENZYME SPECIFICITY; FERRET; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; LIVER HOMOGENATE; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTEIN CLEAVAGE;

ANIMALS; CAROTENOIDS; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FATTY ACID DESATURASES; FERRETS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; KINETICS; LIVER; LUTEIN; OXIDATION-REDUCTION; RECOMBINANT PROTEINS; SPODOPTERA; SUBSTRATE SPECIFICITY; XANTHOPHYLLS;

MAMMALIA; MUSTELA; VERTEBRATA;

EID: 78751633674     PISSN: 00039861     EISSN: 10960384     Source Type: Journal    
DOI: 10.1016/j.abb.2010.11.005     Document Type: Article

References (84)

1. E.J. Johnson, and N.I. Krinsky G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids: Nutrition and Health vol. 5 2009 Birkhäuser Verlag Basel 287 300
2. W. Schalch, J.T. Landrum, and R.A. Bone G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids: Nutrition and Health vol. 5 2009 Birkhäuser Verlag Basel 301 334
3. C.L. Rock G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids: Nutrition and Health vol. 5 2009 Birkhäuser Verlag Basel 269 286
4. A. Bendich J. Nutr. 119 1989 135 136
5. F. Khachik, C.J. Spangler, J.C. Smith Jr., L.M. Canfield, A. Steck, and H. Pfander Anal. Chem. 69 1997 1873 1881
6. G.W. Tang, X.D. Wang, R.M. Russell, and N.I. Krinsky Biochemistry 30 1991 9829 9834
7. X.D. Wang, G.W. Tang, J.G. Fox, N.I. Krinsky, and R.M. Russell Arch. Biochem. Biophys. 285 1991 8 16
8. J.R. Mein, F. Lian, and X.D. Wang Nutr. Rev. 66 2008 667 683
9. X.D. Wang N.I. Krinsky, S.T. Mayne, H. Sies, Carotenoids in Health and Disease 2004 Marcel Dekker New York 313 335
10. S.H. Schwartz, B.C. Tan, D.A. Gage, J.A. Zeevaart, and D.R. McCarty Science (New York, NY) 276 1997 1872 1874
11. J. von Lintig, and K. Vogt J. Biol. Chem. 275 2000 11915 11920
12. A. Lindqvist, and S. Andersson J. Biol. Chem. 277 2002 23942 23948
13. J. Paik, A. During, E.H. Harrison, C.L. Mendelsohn, K. Lai, and W.S. Blaner J. Biol. Chem. 276 2001 32160 32168
14. T.M. Redmond, S. Gentleman, T. Duncan, S. Yu, B. Wiggert, E. Gantt, and F.X. Cunningham Jr. J. Biol. Chem. 276 2001 6560 6565
15. A. Wyss, G.M. Wirtz, W.D. Woggon, R. Brugger, M. Wyss, A. Friedlein, G. Riss, H. Bachmann, and W. Hunziker Biochem. J. 354 2001 521 529
16. W. Yan, G.F. Jang, F. Haeseleer, N. Esumi, J. Chang, M. Kerrigan, M. Campochiaro, P. Campochiaro, K. Palczewski, and D.J. Zack Genomics 72 2001 193 202
17. J. Glover Vitam. Horm. 18 1960 371 386
18. K.Q. Hu, C. Liu, H. Ernst, N.I. Krinsky, R.M. Russell, and X.D. Wang J. Biol. Chem. 281 2006 19327 19338
19. C. Kiefer, S. Hessel, J.M. Lampert, K. Vogt, M.O. Lederer, D.E. Breithaupt, and J. von Lintig J. Biol. Chem. 276 2001 14110 14116
20. R.V. Sharma, S.N. Mathur, A.A. Dmitrovskii, R.C. Das, and J. Ganguly Biochim. Biophys. Acta 486 1976 183 194
21. X.D. Wang, R.M. Russell, C. Liu, F. Stickel, D.E. Smith, and N.I. Krinsky J. Biol. Chem. 271 1996 26490 26498
22. J.L. Napoli, and K.R. Race J. Biol. Chem. 263 1988 17372 17377
23. S. Hessel, A. Eichinger, A. Isken, J. Amengual, S. Hunzelmann, U. Hoeller, V. Elste, W. Hunziker, R. Goralczyk, V. Oberhauser, J. von Lintig, and A. Wyss J. Biol. Chem. 282 2007 33553 33561
24. S.D. Berry, S.R. Davis, E.M. Beattie, N.L. Thomas, A.K. Burrett, H.E. Ward, A.M. Stanfield, M. Biswas, A.E. Ankersmit-Udy, P.E. Oxley, J.L. Barnett, J.F. Pearson, Y. van der Does, A.H. Macgibbon, R.J. Spelman, K. Lehnert, and R.G. Snell Genetics 182 2009 923 926
25. R. Tian, W.S. Pitchford, C.A. Morris, N.G. Cullen, and C.D. Bottema Anim. Genet. 41 2009 253 259
26. F. Lian, D.E. Smith, H. Ernst, R.M. Russell, and X.D. Wang Carcinogenesis 28 2007 1567 1574
27. F. Lian, and X.D. Wang Int. J. Cancer 123 2008 1262 1268
28. J.R. Mein, and X.D. Wang J.T. Landrum, Carotenoids: Physical, Chemical, and Biological Functions and Properties 2010 CRC Press 417 435
29. R.E. Kopec, K.M. Riedl, E.H. Harrison, R.W. Curley, D.P. Hruszkewycz, S.K. Clinton, and S.J. Schwartz J. Agric. Food Chem. 58 2010 3290 3296
30. D.I. Vage, and I.A. Boman BMC Genet. 11 2010 10
31. F. Hill Nature 194 1962 865 866
32. J. Eriksson, G. Larson, U. Gunnarsson, B. Bed'hom, M. Tixier-Boichard, L. Stromstedt, D. Wright, A. Jungerius, A. Vereijken, E. Randi, P. Jensen, and L. Andersson PLoS Genet. 4 2008 e1000010
33. M.P. Castaneda, E.M. Hirschler, and A.R. Sams Poult. Sci. 84 2005 143 147
34. P.S. Bernstein, F. Khachik, L.S. Carvalho, G.J. Muir, D.Y. Zhao, and N.B. Katz Exp. Eye Res. 72 2001 215 223
35. X.D. Wang, N.I. Krinsky, G.W. Tang, and R.M. Russell Arch. Biochem. Biophys. 293 1992 298 304
36. G.W. Tang, and R.M. Russell J. Lipid Res. 31 1990 175 182
37. D. Scherzinger, and S. Al-Babili Mol. Microbiol. 69 2008 231 244
38. C. Garcia-Limones, K. Schnabele, R. Blanco-Portales, M. Luz Bellido, J.L. Caballero, W. Schwab, and J. Munoz-Blanco J. Agric. Food Chem. 56 2008 9277 9285
39. J.T. Vogel, B.C. Tan, D.R. McCarty, and H.J. Klee J. Biol. Chem. 283 2008 11364 11373
40. J.T. Landrum, D.C. Chatfield, A.M. Mebel, F. Alvarez-Calderon, and M.V. Fernandez Arch. Biochem. Biophys. 493 2010 169 174
41. M. Dachtler, T. Glaser, K. Kohler, and K. Albert Anal. Chem. 73 2001 667 674
42. X.D. Wang G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids: Nutrition and Health vol. 5 2009 Birkhäuser Verlag Basel 383 408
43. J. von Lintig, and A. Wyss Arch. Biochem. Biophys. 385 2001 47 52
44. D.P. Kloer, and G.E. Schulz Cell. Mol. Life Sci. 63 2006 2291 2303
45. R.A. Bone, and J.T. Landrum Arch. Biochem. Biophys. 504 2010 50 55
46. R.A. Bone, J.T. Landrum, L.H. Guerra, and C.A. Ruiz J. Nutr. 133 2003 992 998
47. G. Lietz, J. Lange, and G. Rimbach Arch. Biochem. Biophys. 502 2010 8 16
48. IOM, National Academy of Sciences, Food and Nutrition Board, Panel on Dietary Antioxidants and Related Compounds, Dietary Reference Intakes for Vitamin C, Vitamin E, Selenium, and Carotenoids, National Academy Press, Washington, DC, 2000.
49. A. Rogers, and Y. Gibon J. Schwender, Plant Metabolic Networks 2009 Springer New York 98 100
50. F. Bouvier, J.C. Isner, O. Dogbo, and B. Camara Trends Plant Sci. 10 2005 187 194
51. C.M. Cooper, N.W. Davies, and R.C. Menary J. Agric. Food Chem. 51 2003 2384 2389
52. C.M. Cooper, N.W. Davies, and R.C. Menary J. Agric. Food Chem. 57 2009 1513 1520
53. S.M. Al-Hasani, and D.B. Parrish J. Nutr. 102 1972 1437 1440
54. S. Zaripheh, T.W. Boileau, M.A. Lila, and J.W. Erdman Jr. J. Nutr. 133 2003 4189 4195
55. T. Suzuki, M. Matsui, and A. Murayama J. Nutr. Sci. Vitaminol. 41 1995 575 585
56. E.C. Tibaduiza, J.C. Fleet, R.M. Russell, and N.I. Krinsky J. Nutr. 132 2002 1368 1375
57. P. Prakash, C. Liu, K.Q. Hu, N.I. Krinsky, R.M. Russell, and X.D. Wang J. Nutr. 134 2004 667 673
58. J.Y. Winum, M. Kamal, H. Defacque, T. Commes, C. Chavis, M. Lucas, J. Marti, and J.L. Montero Farmaco 52 1997 39 42
59. O. Ziouzenkova, G. Orasanu, G. Sukhova, E. Lau, J.P. Berger, G. Tang, N.I. Krinsky, G.G. Dolnikowski, and J. Plutzky Mol. Endocrinol. (Baltimore, MD) 21 2007 77 88
60. R.E. Duncan, D. Lau, A. El-Sohemy, and M.C. Archer Biochem. Pharmacol. 68 2004 1739 1747
61. J. Liu, B. Li, R. Ma, and B. Chen Wei Sheng Yan Jiu 33 2004 151 153 157
62. J.R. Liu, B.Q. Chen, B.F. Yang, H.W. Dong, C.H. Sun, Q. Wang, G. Song, and Y.Q. Song World J. Gastroenterol. 10 2004 348 351
63. H. Mo, and C.E. Elson J. Nutr. 129 1999 804 813
64. J.R. Liu, X.R. Sun, H.W. Dong, C.H. Sun, W.G. Sun, B.Q. Chen, Y.Q. Song, and B.F. Yang Int. J. Cancer 122 2008 2689 2698
65. K. Aoki, M. Takimoto, H. Ota, and T. Yoshida Pharmacol. Toxicol. 87 2000 26 32
66. T.C. Jeong, H.J. Kim, C.H. Yun, S.S. Lee, K.H. Yang, S.S. Han, and J.K. Roh Biochem. Biophys. Res. Commun. 216 1995 198 202
67. J.R. Liu, H.W. Dong, X.R. Sun, Q. Wang, W.G. Sun, J.W. Parry, Q. Liu, X.H. Han, C.H. Sun, B.Q. Chen, and B.F. Yang Nutr. Cancer 62 2010 58 65
68. F. Lian, K.Q. Hu, R.M. Russell, and X.D. Wang Int. J. Cancer 119 2006 2084 2089
69. A. Matsumoto, H. Mizukami, S. Mizuno, K. Umegaki, J. Nishikawa, K. Shudo, H. Kagechika, and M. Inoue Biochem. Pharmacol. 74 2007 256 264
70. A. Lindqvist, and S. Andersson J. Histochem. Cytochem. 52 2004 491 499
71. A. Lindqvist, Y.G. He, and S. Andersson J. Histochem. Cytochem. 53 2005 1403 1412
72. R.A. Bhatti, S. Yu, A. Boulanger, R.N. Fariss, Y. Guo, S.L. Bernstein, S. Gentleman, and T.M. Redmond Invest. Ophthalmol. Vis. Sci. 44 2003 44 49
73. G.R. Chichili, D. Nohr, M. Schaffer, J. von Lintig, and H.K. Biesalski Invest. Ophthalmol. Vis. Sci. 46 2005 3562 3569
74. G. Moiseyev, Y. Takahashi, Y. Chen, S. Gentleman, T.M. Redmond, R.K. Crouch, and J.X. Ma J. Biol. Chem. 281 2006 2835 2840
75. O. Voolstra, V. Oberhauser, E. Sumser, N.E. Meyer, M.E. Maguire, A. Huber, and J. von Lintig J. Biol. Chem. 285 2010 2130 2139
76. F. Khachik, F.F. de Moura, D.Y. Zhao, C.P. Aebischer, and P.S. Bernstein Invest. Ophthalmol. Vis. Sci. 43 2002 3383 3392
77. J.K. Prasain, R. Moore, J.S. Hurst, S. Barnes, and F.J. van Kuijk J. Mass Spectrom. 40 2005 916 923
78. N.M. Kalariya, K.V. Ramana, S.K. Srivastava, and F.J. van Kuijk Exp. Eye Res. 86 2008 70 80
79. P. Bhosale, and P.S. Bernstein Arch. Biochem. Biophys. 458 2007 121 127
80. E. Loane, J.M. Nolan, O. O'Donovan, P. Bhosale, P.S. Bernstein, and S. Beatty Surv. Ophthalmol. 53 2008 68 81
81. W. Siems, I. Wiswedel, C. Salerno, C. Crifo, W. Augustin, L. Schild, C.D. Langhans, and O. Sommerburg J. Nutr. Biochem. 16 2005 385 397
82. C. Liu, R.M. Russell, and X.D. Wang J. Nutr. 133 2003 173 179
83. S. Veeramachaneni, L.M. Ausman, S.W. Choi, R.M. Russell, and X.D. Wang J. Nutr. 138 2008 1329 1335
84. X.D. Wang, C. Liu, R.T. Bronson, D.E. Smith, N.I. Krinsky, and M. Russell J. Natl. Cancer Inst. 91 1999 60 66