Characterization of recombinant Beta vulgaris 4,5-DOPA-extradiol-dioxygenase active in the biosynthesis of betalains

Planta

Volumn 236, Issue 1, 2012, Pages 91-100

  Gandía Herrero, Fernando ^a   García Carmona, Francisco ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Beta vulgaris; Betalain biosynthesis; Betalamic acid; Dioxygenase; Extradiol; Plant pigment

Indexed keywords

4,5 DOPA EXTRADIOL DIOXYGENASE, BETA VULGARIS; 4,5-DOPA-EXTRADIOL-DIOXYGENASE, BETA VULGARIS; BETALAIN; DIOXYGENASE; OXYGENASE; PIGMENT; RECOMBINANT PROTEIN; VEGETABLE PROTEIN;

ARTICLE; BEET; BIOSYNTHESIS; ENZYMOLOGY; GENE EXPRESSION REGULATION; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; PLANT GENE;

BETA VULGARIS; BETALAINS; DIOXYGENASES; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE EXPRESSION REGULATION, PLANT; GENES, PLANT; OXYGENASES; PIGMENTS, BIOLOGICAL; PLANT PROTEINS; RECOMBINANT PROTEINS;

BETA VULGARIS; CARYOPHYLLALES; ESCHERICHIA COLI;

EID: 84862890226     PISSN: 00320935     EISSN: 14322048     Source Type: Journal    
DOI: 10.1007/s00425-012-1593-2     Document Type: Article

References (48)

1. Bradford MM (1976) A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein dye-binding. Anal Biochem 72: 248-258.
2. Butera D, Tesoriere L, Di Gaudio F, Bongiorno A, Allegra M, Pintaudi AM, Kohen R, Livrea MA (2002) Antioxidant activities of Sicilian prickly pear (Opuntia ficus indica) fruit extracts and reducing properties of its betalains: betanin and indicaxanthin. J Agric Food Chem 50: 6895-6901.
3. Cai Y, Sun M, Corke H (2003) Antioxidant activity of betalains from plants of the Amaranthaceae. J Agric Food Chem 51: 2288-2294.
4. Castellanos-Santiago E, Yahia E (2008) Identification and quantification of betalains from the fruits of 10 Mexican prickly pear cultivars by high-performance liquid chromatography and electrospray ionization mass spectrometry. J Agric Food Chem 56: 5758-5764.
5. Chang C, Kimler L, Mabry TJ (1974) Biogenesis of betalamic acid. Phytochemistry 13: 2771-2775.
6. Christinet L, Burdet FX, Zaiko M, Hinz U, Zrÿd J-P (2004) Characterization and functional identification of a novel plant 4, 5-extradiol dioxygenase involved in betalain pigment biosynthesis in Portulaca grandiflora. Plant Physiol 134: 265-274.
7. de los Reyes BG, Myers SJ, McGrath JM (2003) Differential induction of glyoxylate cycle enzymes by stress as a marker for seedling vigor in sugar beet (Beta vulgaris). Mol Gen Genomics 269: 692-698.
8. Escribano J, Pedreño MA, García-Carmona F, Muñoz R (1998) Characterization of the antiradical activity of betalains from Beta vulgaris L. roots. Phytochem Anal 9: 124-127.
9. Escribano-Cebrián J, García-Carmona F, Gandía-Herrero F (2009) Procedimiento de obtención de ácido betalámico y uso del mismo. European Patent ES 2349522.
10. Feng Y, Khoo HE, Poh CL (1999) Purification and characterization of gentisate 1, 2-dioxygenases from Pseudomonas alcaligenes NCIB 9867 and Pseudomonas putida NCIB 9869. Appl Environ Microbiol 65: 946-950.
11. Fischer N, Dreiding AS (1972) Biosynthesis of betalains. On the cleavage of the aromatic ring during the enzymatic transformation of dopa into betalamic acid. Helv Chim Acta 55: 649-658.
12. Gandía-Herrero F, García-Carmona F, Escribano J (2004) Purification and characterization of a latent polyphenol oxidase from beetroot (Beta vulgaris L.). J Agric Food Chem 52: 609-615.
13. Gandía-Herrero F, García-Carmona F, Escribano J (2005a) Floral fluorescence effect. Nature 437: 334.
14. Gandía-Herrero F, Escribano J, García-Carmona F (2005b) Betaxanthins as pigments responsible for visible fluorescence in flowers. Planta 222: 586-593.
15. Gandía-Herrero F, Escribano J, García-Carmona F (2005c) Betaxanthins as substrates for tyrosinase. An approach to the role of tyrosinase in the biosynthetic pathway of betalains. Plant Physiol 138: 421-432.
16. Gandía-Herrero F, García-Carmona F, Escribano J (2006) Development of a protocol for the semi-synthesis and purification of betaxanthins. Phytochem Anal 17: 262-269.
17. Gandía-Herrero F, Escribano J, García-Carmona F (2007) Characterization of the activity of tyrosinase on betanidin. J Agric Food Chem 55: 1546-1551.
18. Gandía-Herrero F, Escribano J, García-Carmona F (2009a) The role of phenolic hydroxy groups in the free radical scavenging activity of betalains. J Nat Prod 72: 1142-1146.
19. Gandía-Herrero F, Jiménez-Atiénzar M, Cabanes J, Escribano J, García-Carmona F (2009b) Fluorescence detection of tyrosinase activity on dopamine-betaxanthin purified from Portulaca oleracea (common purslane) flowers. J Agric Food Chem 57: 2523-2528.
20. Gandía-Herrero F, Escribano J, García-Carmona F (2010) Structural implication on color, fluorescence, and antiradical activity in betalains. Planta 232: 449-460.
21. Girod P-A, Zryd JP (1991) Biogenesis of betalains: Purification and partial characterisation of DOPA 4, 5-dioxygenase from Amanita muscaria. Phytochemistry 30: 169-174.
22. Gouet P, Courcelle E, Stuart DI, Metoz F (1999) ESPript: multiple sequence alignments in postscript. Bioinformatics 15: 305-308.
23. Heuer S, Richter S, Metzger JW, Wray V, Nimtzt M, Strack D (1994) Betacyanins from bracts of Bougainvillea glabra. Phytochemistry 37: 761-767.
24. Impellizzeri G, Piattelli M, Sciuto S (1973) A new betaxanthin from Glottiphyllum longum. Phytochemistry 12: 2293-2294.
25. Kapadia GJ, Azuine MA, Sridhar R, Okuda Y, Tsuruta A, Ichiishi E, Mukainake T, Takasaki M, Konoshima T, Nishino H, Tokuda H (2003) Chemoprevention of DMBA-induced UV-B promoted, NOR-1-induced TPA promoted skin carcinogenesis, and DEN-induced phenobarbital promoted liver tumors in mice by extract of beetroot. Pharmacol Res 47: 141-148.
26. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227: 680-685.
27. Lipscomb JD (2008) Mechanism of extradiol aromatic ring-cleaving dioxygenases. Curr Opin Struct Biol 18: 644-649.
28. Lu X, Wang Y, Zhang Z (2009) Radioprotective activity of betalains from red beets in mice exposed to gamma irradiation. Eur J Pharmacol 615: 223-227.
29. Marquardt DW (1963) An algorithm for least-squares estimation of nonlinear parameters. J Soc Ind Appl Math 11: 431-441.
30. Marusek CM, Trobaugh NM, Flurkey WH, Inlow JK (2006) Comparative analysis of polyphenol oxidase from plant and fungal species. J Inorg Biochem 100: 108-123.
31. Moreno DA, García-Viguera C, Gil JI, Gil-Izquierdo A (2008) Betalains in the era of global agri-food science, technology and nutritional health. Phytochem Rev 7: 261-280.
32. Mueller LA, Hinz U, Zrÿd JP (1996) Characterization of a tyrosinase from Amanita muscaria involved in betalain biosynthesis. Phytochemistry 42: 1511-1515.
33. Mueller LA, Hinz U, Zrÿd JP (1997) The formation of betalamic acid and muscaflavin by recombinant DOPA-dioxygenase from Amanita. Phytochemistry 44: 567-569.
34. Musso H (1979) Pigments of fly agaric, Amanita muscaria. Tetrahedron 35: 2843-2853.
35. Pavlov A, Kovatcheva P, Georgiev V, Koleva I, Ilieva M (2002) Biosynthesis and radical scavenging activity of betalains during the cultivation of red beet (Beta vulgaris) hairy root cultures. Z Naturforsch 57: 640-644.
36. Piattelli M, Minale L, Nicolaus RA (1965) Betaxanthins from Mirabilis jalapa L. Phytochemistry 4: 817-823.
37. Piattelli M (1981) The betalains: structure, biosynthesis, and chemical taxonomy. In: Conn EE (ed) The biochemistry of plants, vol 7. Academic Press Inc, New York, pp 557-575.
38. Sasaki N, Abe Y, Goda Y, Adachi T, Kasahara K, Ozeki Y (2009) Detection of DOPA 4, 5-dioxygenase (DOD) activity using recombinant protein prepared from Escherichia coli cells harboring cDNA encoding DOD from Mirabilis jalapa. Plant Cell Physiol 50: 1012-1016.
39. Schliemann W, Kobayashi N, Strack D (1999) The decisive step in betaxanthin biosynthesis is a spontaneous reaction. Plant Physiol 119: 1217-1232.
40. Stafford HA (1994) Anthocyanins and betalains: evolution of the mutually exclusive pathways. Plant Sci 101: 91-98.
41. Steiner U, Schliemann W, Böhm H, Strack D (1999) Tyrosinase involved in betalain biosynthesis of higher plants. Planta 208: 114-124.
42. Stintzing FC, Carle R (2004) Functional properties of anthocyanins and betalains in plants, food, and in human nutrition. Trends Food Sci Technol 15: 19-38.
43. Tesoriere L, Butera D, D'Arpa D, Di Gaudio F, Allegra M, Gentile C, Livrea MA (2003) Increased resistance to oxidation of betalain-enriched human low density lipoproteins. Free Radic Res 37: 689-696.
44. Trezzini GF, Zrÿd J-P (1991) Characterization of some natural and semisynthetic betaxanthins. Phytochemistry 30: 1901-1904.
45. von Ardenne R, Döpp H, Musso H, Steiglich W (1974) Über das Vorkommen von Muscaflavin bei Hygrocyben (Agaricales) und seine Dihydroazepin-Struktur. Z Naturforsch 29c: 637-639.
46. Wybraniec S (2007) A method for identification of diastereomers of 2-decarboxy-betacyanins and 2, 17-bidecarboxy-betacyanins in reversed-phase HPLC. Anal Bioanal Chem 389: 1611-1621.
47. Wyler H, Dreiding AS (1957) Kristallisiertes Betanin. Hel Chim Acta 40: 191-192.
48. Wyler H, Wilcox ME, Dreiding AS (1965) Umwandlung eines betacyans in ein betaxanthin. synthese von indicaxanthin aus betanin. Helv Chim Acta 48: 361-366.