A novel carotenoid, 4-keto-α-carotene, as an unexpected by-product during genetic engineering of carotenogenesis in rice callus

Phytochemistry

Volumn 98, Issue , 2014, Pages 85-91

  Breitenbach, Jürgen ^a   Bai, Chao ^b   Rivera, Sol M ^b   Canela, Ramon ^b   Capell, Teresa ^b   Christou, Paul ^b,c   Zhu, Changfu ^b   Sandmann, Gerhard ^a  

^a GOETHE UNIVERSITY   (Germany)

^b UNIVERSITY OF LLEIDA   (Spain)

^c INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

4 keto carotene; Astaxanthin; Carotenoid biosynthesis; Genetic engineering; Rice endosperm

Indexed keywords

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

CAROTENOID;

BIOSYNTHESIS; CHEMISTRY; GENETIC ENGINEERING; GENETICS; METABOLISM; RICE;

CAROTENOIDS; GENETIC ENGINEERING; ORYZA SATIVA;

EID: 84892925005     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.12.008     Document Type: Article

References (44)

1. C. Bai, S.M. Rivera, V. Medina, R. Alves, E. Vilaprinyo, A. Sorriba, R. Canela, T. Capell, G. Sandmann, P. Christou, and C. Zhu An in vitro system for the rapid functional characterization of genes involved in carotenoid biosynthesis and accumulation Plant J. 2013 10.1111/tpj.12384 2013 Nov 23
2. B. Bjerkeng Carotenoids in aquaculture: fish and crustaceans G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids Natural Functions vol. 4 2008 Birkhäuser Verlag Basel 237 254
3. J. Breitenbach, T. Gerjets, and G. Sandmann Catalytic properties and reaction mechanism of the CrtO carotenoid ketolase from the cyanobacterium Synechocystis sp. PCC 6803 Arch. Biochem. Biophys. 529 2013 86 91
4. G. Britton, S. Liaaen-Jensen, and H. Pfander Carotenoids Handbook 2004 Birkhäuser Verlag Basel
5. B. Buckner, P. San Miguel, D. Janick-Buckner, and J.L. Bennetzent The yl gene of maize codes for phytoene synthase Genetics 143 1996 479 488 (Pubitemid 26137007)
6. F.X. Cunningham, B. Pogson, Z. Sun, K.A. McDonald, D. DellaPenna, and E. Gantt Functional analysis of the β and lycopene cyclase enzymes of Arabidopsis reveals a mechanism for control of cyclic carotenoid formation Plant Cell 8 1996 1613 1626 (Pubitemid 26380832)
7. C.R. Enzell, and S. Back Mass spectrometry G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids Spectroscopy vol. 1B 1995 Birkhäuser Verlag Basel 261 320
8. C.R. Enzell, G.W. Francis, and S. Liaaen-Jensen Mass spectrometric studies of carotenoids. 2. A survey of fragmentation reactions Acta Chem. Scand. 23 1969 727 750
9. C.H. Eugster Chemical derivatization: microsomale tests for the presence of common functional groups in carotenoids G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids Isolation and Analysis vol. 1A 1995 Birkhäuser Verlag Basel 71 80
10. G. Farre, S. Naqvi, G. Sanahuja, C. Bai, U. Zorrilla-López, S.M. Rivera, R. Canela, G. Sandmann, R.M. Twyman, T. Capell, C. Zhu, and P. Christou Combinatorial genetic transformation of cereals and the creation of metabolic libraries for the carotenoid pathway Methods Mol. Biol. 847 2012 419 435
11. P.D. Fraser, S. Römer, C.A. Shipton, P.B. Mills, J.W. Kiano, N. Misawa, R.G. Darke, W. Schuch, and P.M. Bramley Evaluation of transgenic tomato plants expressing an additional phytoene synthase in a fruit-specific manner Proc. Natl. Acad. Sci. USA 99 2002 1092 1097 (Pubitemid 34106641)
12. P.D. Fraser, E.M. Enfissi, and P.M. Bramley Genetic engineering of carotenoid formation in tomato fruit and the potential application of systems and synthetic biology approaches Arch. Biochem. Biophys. 483 2009 196 204
13. T. Gerjets, M. Sandmann, C. Zhu, and G. Sandmann Metabolic engineering of ketocarotenoid biosynthesis in leaves and flowers of tobacco species Biotechnol. J. 2 2007 1263 1269 (Pubitemid 350047843)
14. M. Guerin, M.E. Huntley, and M. Olaizola Haematococcus astaxanthin: applications for human health and nutrition Trends Biotechnol. 21 2003 210 216 (Pubitemid 36515074)
15. A. Hausmann, and G. Sandmann A single 5-step desaturase is involved in the carotenoid biosynthesis pathway to ß-carotene and torulene in Neurospora crassa Fung. Gen. Biol. 30 2000 147 153
16. G. Hussein, U. Sankawa, H. Goto, K. Matsumoto, and H. Watanabe Astaxanthin, a carotenoid in human health and nutrition J. Nat. Prod. 69 2006 443 449
17. H. Kayser Ectatosoma tiaratum, isolation of β,ε-carotene-2-ol and β,ε-carotene-2-one Z. Naturforsch. 36c 1981 755 764
18. M.E. Kovach, R.W. Phillips, P.H. Elzer, R.M. Roop, and K.M. Peterson PBBR1MCS: a broad-host-range cloning vector Biotechniques 16 1994 800 802 (Pubitemid 2103380)
19. H. Linden, A. Vioque, and G. Sandmann Isolation of a carotenoid biosynthesis gene coding for a zeta-carotene desaturase from Anabaena PCC7120 by heterologous complementation FEMS Microbiol. Lett. 106 1993 99 104 (Pubitemid 23025071)
20. N. Misawa Pathway engineering for functional isoprenoids Curr. Opin. Biotechnol. 22 2011 627 633
21. N. Misawa, K. Masamoto, T. Hori, T. Ohtani, P. Böger, and G. Sandmann Expression of an Erwinia phytoene desaturase gene not only confers multiple resistance to herbicides interfering with carotenoid biosynthesis but also alters xanthophyll metabolism in transgenic plants Plant J. 6 1994 481 489
22. N. Misawa, Y. Satomi, K. Kondo, A. Yokoyama, S. Kajiwara, T. Saito, T. Ohtani, and W. Miki Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level J. Bacteriol. 177 1995 6575 6584
23. S. Naqvi, C. Zhu, G. Farre, G. Sandmann, T. Capell, and P. Christou Synergistic metabolism in hybrid corn reveals bottlenecks in the carotenoid pathway and leads to the accumulation of extraordinary levels of the nutritionally important carotenoid zeaxanthin Plant Biotechnol. J. 9 2011 384 393
24. Y. Nishida, K. Adachi, H. Kasai, Y. Shizuri, K. Shindo, A. Sawabe, S. Komemushi, W. Miki, and N. Misawa Elucidation of a carotenoid biosynthesis gene cluster encoding a novel enzyme, 2,2′-beta-hydroxylase, from Brevundimonas sp. strain SD212 and combinatorial biosynthesis of new or rare xanthophylls Appl. Environ. Microbiol. 71 2005 4286 4296 (Pubitemid 41129479)
25. J.A. Paine, C.A. Shipton, R.M. Chaggar, R.M. Howells, M.J. Kennedy, G. Vernon, S.Y. Wright, E. Hinchliffe, J.L. Adams, A.L. Silverstone, and R. Drake Improving the nutritional value of Golden Rice through increased pro-vitamin A content Nat. Biotechnol. 23 2005 482 487 (Pubitemid 41724925)
26. F.W. Quackenbush, J.G. Firch, A.M. Brunson, and L.R. House Carotenoid, oil, and tocopherol content of corn inbreds Cereal Chem. 40 1963 250 253
27. S. Rivera, F. Vilaró, and R. Canela Determination of carotenoids by liquid chromatography/mass spectrometry: effect of several dopants Analyt. Bioanalyt. Chem. 400 2011 1339 1346
28. S.M. Rivera, F. Vilaró, C. Zhu, C. Bai, G. Farré, P. Christou, and R. Canela-Garayoa Fast quantitative method for the analysis of carotenoids in transgenic aize J. Agric. Food Chem. 61 2013 5279 5285
29. S. Römer, J. Lübeck, F. Kauder, S. Steiger, C. Adomat, and G. Sandmann Genetic engineering of a zeaxanthin-rich potato by antisense inactivation and co-suppression of carotenoid epoxidation Metabolic Engin. 4 2002 263 272 (Pubitemid 36035670)
30. J. Sambrook, E.F. Fritsch, and T. Maniatis Molecular Cloning: A Laboratory Manua 2nd Ed. 1989 Cold Spring Harbor Laboratory Press Cold Spring Harbor, New York
31. G. Sandmann Genetic manipulation of carotenoid biosynthesis: strategies, problems and achievements Trends Plant Sci. 6 2001 14 17 (Pubitemid 33141450)
32. G. Sandmann Combinatorial biosynthesis of carotenoids in a heterologous host: a powerful approach for the biosynthesis of novel structures Chem. Bio. Chem. 3 2002 629 635 (Pubitemid 36004526)
33. G. Sandmann, S. Römer, and P.D. Fraser Understanding carotenoid metabolism as a necessity for genetic engineering of crop plants Metabolic Eng. 8 2006 291 302 (Pubitemid 43903303)
34. P. Schaub, S. Al-Babili, R. Drake, and P. Beyer Why is golden rice golden (yellow) instead of red? Plant Physiol. 138 2005 441 450 (Pubitemid 43138142)
35. P. Schreier, E. Seftor, J. Schell, and H. Bohnert The use of nuclear-encoded sequences to direct the light regulated synthesis and transport of a foreign protein into plant chloroplasts EMBO J. 4 1985 25 32
36. M.B. Sørensen, M. Müller, J. Skerritt, and D. Simpson Hordein promoter methylation and transcriptional activity in wild-type and mutant barley endosperm Mol. Gen. Genet. 250 1996 750 760
37. S. Steiger, L. Schäfer, and G. Sandmann High-light upregulation of carotenoids and their antioxidative properties in the cyanobacterium Synechocystis PCC 6803 J. Photochem. Photobiol., B 521 1999 14 18 (Pubitemid 30011490)
38. E. Stoger, S. Williams, D. Keen, and P. Christou Constitutive versus seed specific expression in transgenic wheat: temporal and spatial control Transgenic Res. 8 1999 73 82 (Pubitemid 29368584)
39. T. Sugio, J. Satoh, H. Matsuura, A. Shinmyo, and K. Kato The 5′-untranslated region of the Oryza sativa alcohol dehydrogenase gene functions as a translational enhancer in monocotyledonous plant cells J. Biosci. Bioeng. 105 2008 300 330
40. R.B. Van Breemen, L. Dong, and N.D. Pajkovic Atmospheric pressure chemical ionization tandem mass spectrometry of carotenoids Int. J. of Mass Spectrometry 312 2012 163 172
41. X. Ye, S. Al-Babili, A. Klöti, J. Zhang, P. Lucca, P. Beyer, and I. Potrykus Engineering the provitamin A (beta-carotene) biosynthetic pathway into (carotenoid-free) rice endosperm Science 287 2000 303 305 (Pubitemid 30046756)
42. Y.J. Zhong, Y.C. Huang, J. Liu, Y. Li, Y. Jiang, Z.F. Xu, G. Sandmann, and F. Chen Functional characterization of various algal carotenoid ketolases reveals that ketolating zeaxanthin efficiently is essential for high production of astaxanthin in transgenic Arabidopsis J. Exp. Bot. 62 2011 3659 3669
43. C. Zhu, S. Naqvi, J. Breitenbach, G. Sandmann, P. Christou, and T. Capell Combinatorial genetic transformation generates a library of metabolic phenotypes for the carotenoid pathway in maize Proc. Natl. Acad. Sci. USA 105 2008 18232 18237
44. C. Zhu, S. Naqvi, T. Capell, and P. Christou Metabolic engineering of ketocarotenoid biosynthesis in higher plants Arch. Biochem. Biophys. 483 2009 182 190