Production of caloxanthin 3′-β-d-glucoside, zeaxanthin 3,3′-β-d-diglucoside, and nostoxanthin in a recombinant Escherichia coli expressing system harboring seven carotenoid biosynthesis genes, including crtX and crtG

Phytochemistry

Volumn 72, Issue 8, 2011, Pages 711-716

  Osawa, Ayako ^a   Harada, Hisashi ^b   Choi, Seon Kang ^c   Misawa, Norihiko ^b,d   Shindo, Kazutoshi ^a  

^a JAPAN WOMEN'S UNIVERSITY   (Japan)

^b KIRIN HOLDINGS CO LTD   (Japan)

^c Gangnueung Science Industry Park   (South Korea)

^d ISHIKAWA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

1O2 quenching activity; Caloxanthin 3 d glucoside; CrtG; CrtX; Nostoxanthin; Recombinant Escherichia coli; Zeaxanthin 3,3 d diglucoside

Indexed keywords

ANTIOXIDANT; CALOXANTHIN 3' BETA D GLUCOSIDE; CALOXANTHIN 3'-BETA-D-GLUCOSIDE; CAROTENOID; GLUCOSIDE; NOSTOXANTHIN; XANTHOPHYLL; ZEAXANTHIN 3,3' BETA D DIGLUCOSIDE; ZEAXANTHIN 3,3'-BETA-D-DIGLUCOSIDE;

ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; ESCHERICHIA COLI; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; STEREOISOMERISM;

ANTIOXIDANTS; CAROTENOIDS; ESCHERICHIA COLI; GLUCOSIDES; MOLECULAR STRUCTURE; STEREOISOMERISM; XANTHOPHYLLS;

ESCHERICHIA COLI;

EID: 79954627687     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.02.017     Document Type: Article

References (29)

1. G. Britton, S. Liaaen-Jensen, and H. Pfander Carotenoid Handbook 2004 Birkhauser Verlag Basel
2. H. Harada, and N. Misawa Novel approaches and achievements in biosynthesis of functional isoprenoids in Escherichia coli Appl. Microbiol. Biotechnol. 84 2009 1021 1031
3. H. Harada, F. Yu, S. Okamoto, T. Kuzuyama, R. Utsumi, and N. Misawa Efficient synthesis of functional isoprenoids from acetoacetate through metabolic pathway-engineered Escherichia coli Appl. Microbiol. Biotechnol. 81 2009 915 925
4. O. Hirayama, K. Nakamura, S. Hamada, and Y. Kobayashi Singlet oxygen quenching ability of naturally occurring carotenoids Lipids 29 1994 149 150 (Pubitemid 24073052)
5. M. Hosokawa, M. Kudo, H. Maeda, H. Kohno, T. Tanaka, and K. Miyashita Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPARg ligand, troglitazone, on colon cancer cells Biochim. Biophys. Acta 1675 2004 113 119 (Pubitemid 39463260)
6. B.S. Hundle, P. Beyer, H. Kleinig, G. Englert, and J.E. Hearst Carotenoids of Erwinia herbicola and an Escherichia coli HB101 strain carrying the Erwinia herbicola carotenoid gene cluster Photochem. Photobiol. 54 1991 89 93
7. B.S. Hundle, D.A. O'Brien, M. Alberti, P. Beyer, and J.E. Hearst Functional expression of zeaxanthin glucosyltransferase from Erwinia herbicola and a proposed uridine diphosphate binding site Proc. Natl. Acad. Sci. USA 89 1992 9321 9325
8. M. Iwai, T. Maoka, M. Ikeuchi, and S. Takaichi 2, 2′-β- Hydroxylase (CrtG) is involved in carotenogenesis of both nostoxanthin and 2-hydroxymyxol 2′-fucoside in Thermosynechococcus elongatus strain BP-1 Plant Cell Physiol. 49 2008 1678 1687
9. T. Iwamoto, K. Hosoda, R. Hirano, H. Kurata, A. Matsumoto, W. Miki, M. Kamiyama, H. Itakura, S. Yamamoto, and K. Kondo Inhibition of low-density lipoprotein oxidation by astaxanthin J. Atheroscler. Thromb. 7 2000 216 222
10. K. Kaneda, T. Kuzuyama, M. Takagi, Y. Hayakawa, and H. Seto An unusual isopentenyl diphosphate isomerase found in the mevalonate pathway gene cluster from Streptomyces sp. strain CL190 Proc. Natl. Acad. Sci. USA 98 2001 932 937 (Pubitemid 32121165)
11. M. Kobayashi, and Y. Sakamoto Singlet oxygen quenching ability of astaxanthin esters from the green alga Haematococcus pluvialis Biotechnol. Left 21 1999 265 269 (Pubitemid 29224622)
12. P.C. Lee, A.Z.R. Momen, B.N. Mijts, and C. Schmidt-Dannert Biosynthesis of structurally novel carotenoids in Escherichia coli Chem. Biol. 10 2003 453 462 (Pubitemid 36599253)
13. T. Maruyama, H. Kasai, S.-K. Choi, A.K. Ramasamy, Y. Inomata, and N. Misawa Structure of a complete carotenoid biosynthesis gene cluster of marine bacterium Paracoccus sp. strain N81106 Carotenoid Sci. 11 2007 50 55
14. N. Misawa Pathway engineering of plants toward astaxanthin production Plant Biotechnol. 26 2009 93 99
15. N. Misawa Carotenoids L. Mander, H.-W. Lui, Comprehensive Natural Products II Chemistry and Biology vol. 1 2010 Elsevier Oxford 733 753
16. N. Misawa, M. Nakagawa, K. Kobayashi, S. Yamano, Y. Izawa, K. Nakamura, and K. Harashima Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli J. Bacteriol. 172 1990 6704 6712
17. 40-carotenoids by iodine., J Chem. Soc. Perkin Trans. 2 1993 261 266
18. Y. Naito, K. Uchiyama, W. Aoi, G. Hasegawa, N. Nakamura, N. Yoshida, T. Maoka, J. Takahashi, and T. Yoshikawa Prevention of diabetic nephropathy by treatment with astaxanthin in diabetic db/db mice Biofactors 20 2004 49 59 (Pubitemid 38586209)
19. M. Nakagawa, and N. Misawa Analysis of carotenoid glycosides produced in gram-negative bacteria by introduction of the Erwinia uredovora carotenoid biosynthesis genes Agric. Biol. Chem. 55 1991 2147 2148
20. 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′-β-hydroxylase, from Brevundimonas sp. strain SD212 and combinatorial biosynthesis of new or rare xanthophylls Appl. Environ. Microbiol. 71 2005 4286 4296 (Pubitemid 41129479)
21. H. Nishino, H. Tokuda, M. Murakoshi, Y. Satomi, M. Masuda, M. Onozuka, S. Yamaguchi, J. Takayasu, J. Tsuruta, M. Okuda, F. Khachik, T. Narisawa, N. Takasuka, and M. Yano Cancer prevention by natural carotenoids Biofactors 13 2000 89 94 (Pubitemid 32107350)
22. J. Sambrook, and D.W. Russell Molecular Cloning: A Laboratory Manual third ed. 2001 Cold Spring Harbor Laboratory Press Cold Spring Harbor, NY
23. K. Shindo, T. Hasunuma, E. Asagi, A. Sano, E. Hotta, N. Minemura, C. Miyake, T. Maoka, and N. Misawa 4-Ketoantheraxanthin, a novel carotenoid produced by the combination of the bacterial enzyme β-carotene ketolase CrtW and endogenous carotenoid biosynthetic enzymes in higher plants Tetrahedron Lett. 49 2008 3294 3296
24. S.A. Talegawkar, E.J. Johnson, T.C. Carithers, H.A. Taylor Jr., M.L. Bogle, and K.L. Tucker Carotenoid intakes, assessed by food-frequency questionnaires (FFQs), are associated with serum carotenoid concentrations in the Jackson Heart Study: validation of the Jackson Heart Study Delta NIRI Adult FFQs Public Health Nutr. 11 2008 989 997
25. L. Tao, P.E. Rouvire, and Q. Cheng A carotenoid synthesis gene cluster from a non-marine Brevundimonas that synthesizes hydroxylated astaxanthin Gene 379 2006 101 108 (Pubitemid 44247329)
26. H. Tatsuzawa, T. Maruyama, N. Misawa, K. Fujimori, and M. Nakano Quenching of singlet oxygen by carotenoids produced in Escherichia coli-attenuation of singlet oxygen-mediated bacterial killing by carotenoids FEBS Lett. 484 2000 280 284
27. A. Yokoyama, K. Adachi, and Y. Shizuri New carotenoid glucosides, astaxanthin glucoside and adonixanthin glucoside, isolated from the astaxanthin-producing marine bacterium Agrobacterium aurantiacum J. Nat. Prod. 58 1995 1929 1933 (Pubitemid 26071152)
28. A. Yokoyama, W. Miki, H. Izumida, and Y. Shizuri New trihydroxy-keto- carotenoids isolated from an astaxanthin-producing marine bacterium Biosci. Biotechnol. Biochem. 60 1996 200 203
29. A. Yokoyama, Y. Shizuri, and N. Misawa Production of new carotenoids, astaxanthin glucosides, by Escherichia coli transformants carrying carotenoid biosynthetic genes Tetrahedron Lett. 39 1998 3709 3712 (Pubitemid 28222454)