Fluorescence detection of tyrosinase activity on dopamine-betaxanthin purified from portulaca oleracea (common purslane) flowers

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 6, 2009, Pages 2523-2528

  Gandía Herrero, Fernando ^a   Jiménez Atiénzar, Mercedes ^a   Cabanes, Juana ^a   Escribano, Josefa ^a   García Carmona, Francisco ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Betalain; Betaxanthin; Fluorescence; Portulaca oleracea; Tyrosinase

Indexed keywords

BETALAIN; BETAXANTHIN; DOPAMINE; DRUG DERIVATIVE; FLUORESCEIN DERIVATIVE; MONOPHENOL MONOOXYGENASE; OUABAIN; PICOLINIC ACID DERIVATIVE; RHODOL GREEN ETHYLENEDIAMINE OUABAIN; RHODOL GREEN-ETHYLENEDIAMINE-OUABAIN;

ARTICLE; CHEMISTRY; FLOWER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; METABOLISM; PORTULACACEAE; SPECTROFLUOROMETRY;

BETALAINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOPAMINE; FLOWERS; FLUORESCEINS; MONOPHENOL MONOOXYGENASE; OUABAIN; PICOLINIC ACIDS; PORTULACA; SPECTROMETRY, FLUORESCENCE;

CARYOPHYLLALES; PORTULACA OLERACEA; PORTULACACEAE;

EID: 64549124754     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf803608x     Document Type: Article

References (36)

1. Burton, S. G. Biocatalysis with polyphenol oxidase - a review. Catal. Today 1994, 22, 459-487.
2. Sanchez-Ferrer, A.; Rodriguez-López, J. N.; García- Cánovas, F.; García-Carmona, F. Tyrosinase: a comprehensive review of its mechanism. Biochim. Biophys. Acta 1995, 1247, 1-11.
3. van Gelder, C. W. G.; Flurkey, W. H.; Wichers, H. J. Sequence and structural features of plant and fungal tyrosinases. Phytochem-istry 1997, 45, 1309-1323.
4. Marusek, C. M.; Trobaugh, N. M.; Flurkey, W. H.; Inlow, J. K. Comparative analysis of polyphenol oxidase from plant and fungal species. J. Inorg. Biochem. 2006, 100, 108-123.
5. Klabunde, T.; Eicken, C.; Sacchettini, J. C.; Krebs, B. Crystal structure of a plant catechol oxidase containing a dicopper center. Nat. Struct. Biol. 1998, 5, 1084-1090.
6. Matoba, Y.; Kumagai, T.; Yamamoto, A.; Yoshitsu, H.; Sugiyama, M. Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis. J. Biol. Chem. 2006, 281, 8981-8990.
7. Seo, S.-Y.; Sharma, V. K.; Sharma, N. Mushroom tyrosinase: recent prospects. J. Agric. Food Chem. 2003, 51, 2837-2853.
8. Piattelli, M. The betalains: structure, biosynthesis, and chemical taxonomy. In The biochemistry of plants; Conn, E. E., Ed.; Academic Press Inc.: New York, NY, 1981; Vol. 7, pp 557-575.
9. Moreno, D. A.; García-Viguera, C.; Gil, J. I.; Gil-Izquierdo, A. Betalains in the era of global agri-food science, technology and nutritional health. Phytochem. Rev. 2008, 7, 261-280.
10. Musso, H. Pigments of fly agaric, Amanita muscaria. Tetrahedron 1979, 35, 2843-2853.
11. von Ardenne, R.; Döpp, H.; Musso, H.; Steiglich, W. Über das Vorkommen von Muscaflavin bei Hygrocyben (Agaricales) und seine Dihydroazepin-Struktur. Z. Naturforsch. 1974, 29c, 637-639.
12. Stafford, H. A. Anthocyanins and betalains: evolution of the mutually exclusive pathways. Plant Sci. 1994, 101, 91-98.
13. Piattelli, M.; Minale, L.; Nicolaus, R. A. Betaxanthins from Mirabilis jalapa L. Phytochemistry 1965, 4, 817-823.
14. Impellizzeri, G.; Piattelli, M.; Sciuto, S. A new betaxanthin from Glottiphylum longum. Phytochemistry 1973, 12, 2293-2294.
15. Gandía-Herrero, F.; Escribano, J.; García-Carmona, F. Betaxanthins as pigments responsible for visible fluorescence in flowers. Planta 2005, 222, 586-593.
16. Gandía-Herrero, F.; Escribano, J.; García-Carmona, F. Betaxanthins as substrates for tyrosinase. An approach to the role of tyrosinase in the biosynthetic pathway of betalains. Plant Physiol. 2005, 138, 421-432.
17. Escribano, J.; Pedreño, M. A.; García-Carmona, F.; Muñoz, R. Characterization of the antiradical activity of betalains from Beta vulgaris L. roots. Phytochem. Anal. 1998, 9, 124-127.
18. Wyler, H.; Wilcox, M. E.; Dreiding, A. S. Umwandlung eines Betacyans in ein Betaxanthin. Synthese von Indicaxanthin aus Betanin. Helv. Chim. Acta 1965, 48, 361-366.
19. Gandía-Herrero, F.; García-Carmona, F.; Escribano, J. Development of a protocol for the semi-synthesis and purification of betaxanthins. Phytochem. Anal. 2006, 17, 262-269.
20. Schliemann, W.; Kobayashi, N.; Strack, D. The decisive step in betaxanthin biosynthesis is a spontaneous reaction. Plant Physiol. 1999, 119, 1217-1232.
21. Trezzini, G. F.; Zryd, J.-P. Characterization of some natural and semisynthetic betaxanthins. Phytochemistry 1991, 30, 1901-1904.
22. Schwartz, S. J.; von Elbe, J. H. Quantitative determination of individual betacyanin pigments by high-performance liquid chro-matography. J. Agric. Food Chem. 1980, 28, 540-543.
23. Marquardt, D. W. An algorithm for least-squares estimation of nonlinear parameters. J. Soc. Ind. Appl. Math. 1963, 11, 431-441.
24. Trezzini. G. F.: Zrÿd, J.-P. Two betalains from Portulaca gran-diflora. Phytochemistry 1991, 30, 1897-1899.
25. Schliemann, W.; Cai, Y.; Degenkolb, T.; Schmidt, J.; Corke, H. Betalains of Celosia argentea. Phytochemistry 2001, 58, 159-165.
26. Girod, P.-A.; Zryd, J.-P. Secondary metabolism in cultured red beet (Beta vulgaris L.) cells: Differential regulation of betaxanthin and betacyanin biosynthesis. Plant Cell, Tissue Organ Cult. 1991, 25, 1-12.
27. Piattelli, M.; Impellizzeri, G. 2-Descarboxybetanidin, a minor betacyanin from Carpobrothus acinaciformis. Phytochemistry 1970, 9, 2553-2556.
28. Gandia-Herrero, F.; Escribano, J.; García-Carmona, F. Characterization of the monophenolase activity of tyrosinase on betaxanthins: the tyramine-betaxanthin/dopamine-betaxanthin pair. planta 2005, 222, 307-318.
29. Stintzing, F. C.; Carle, R. Functional properties of anthocyanins and betalains in plants, food, and in human nutrition. Trends Food Sci. Technol. 2004, 15, 19-38.
30. Mercuri, A.; Sacchetti, A.; De Benedetti, L.; Schiva, T.; Saverio, A. Green fluorescent flowers. Plant Sci. 2001, 161, 961-968.
31. Gandía-Herrero, F.; García-Carmona, F.; Escribano, J. Floral fluorescence effect. Nature 2005, 437, 334.
32. Mertens, M. L.; Kägi, J. H. R. A graphical procedure for inner filter effect in fluorescence quenching titrations. Anal. Biochem. 1979, 96, 448-455.
33. Ehrhardt, D. GFP technology for live cell imaging. Curr. Opin. Plant. Biol. 2003, 6, 622-628.
34. Wink, M. Compartmentation of secondary metabolites and xe-nobiotics in plant vacuoles. Adv. Bot. Res. 1997, 25, 141-169.
35. Sasaki, K.; Takahashi, T. A flavonoid from Brassica rapa flower as the UV-absorbing nectar guide. Phytochemistry 2002, 61, 339-343.
36. Heiling, A. M.; Herberstein, M. E.; Chittka, L. Pollinator attraction: Crab-spiders manipulate flower signals. Nature 2003, 421, 334.