Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves

Phytochemistry

Volumn 62, Issue 3, 2003, Pages 301-306

  Niemetz, Ruth ^a   Gross, Georg G ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

Ellagitannin biosynthesis; Fringe cups; Laccase; Pentagalloylglucose; Phenol oxidase; Saxifragaceae; Tellima grandiflora; Tellimagrandin II

Indexed keywords

ELLAGITANNIN; GLUCOSE PENTAGALLATE; MONOPHENOL MONOOXYGENASE; TELLIMAGRANDIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG ISOLATION; ENZYME ISOLATION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HYDROLYSIS; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; PLANT LEAF; STEREOCHEMISTRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME INHIBITORS; GALLIC ACID; GLUCOSIDES; HYDROGEN-ION CONCENTRATION; HYDROLYZABLE TANNINS; MOLECULAR WEIGHT; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION; PLANT LEAVES; SAXIFRAGACEAE; STEREOISOMERISM; TANNINS;

SAXIFRAGACEAE; TELLIMA GRANDIFLORA;

EID: 0037310568     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00557-5     Document Type: Article

References (24)

1. Davin, L.B., Wang, H.-B., Crowell, A.L., Bedgar, D.L., Martin, D.M., Sarkanen, S., Lewis, N.G., 1997. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275, 363-366.
2. De Pinto, M.C., Ros Barceló, A., 1996. Inhibition of both peroxidase and laccase by desferal (desferrioxamine mesylate). Phytochemistry 42, 283-286.
3. Erdtman, H., 1935. Phenoldehydrierungen VI. Dehydrierende Kupplung einiger Guajakolderivate. Svenska Kemisk Tidskrift 47, 223-230.
4. Feldman, S., Sahasrabudhe, K., 1999. Ellagitannin chemistry. Syntheses of tellimagrandin II and a dehydrodigalloyl ether-containing dimeric gallotannin analogue of coriariin A. Journal of Organic Chemistry 64, 209-216.
5. Ferrar, P.H., Walker, J.R.L., 1996. Inhibition of diphenol oxidase: a comparative study. Journal of Food Biochemistry 20, 15-30.
6. Fröhlich, B., Niemetz, R., Gross, G.G., 2002. Gallotannin biosynthesis: two new galloyltransferases from Rhus typhina leaves preferentially acylating hexa- and heptagalloylglucoses. Planta 216, 168-172.
7. Haslam, E., 1989. Plant Polyphenols. Vegetable Tannins Revisited. Cambridge University Press, Cambridge.
8. Haslam, E., 1998. Practical Polyphenols. From Structure to Molecular Recognition and Physiological Action. Cambridge University Press, Cambridge.
9. Hathway, D.E., 1957. The transformation of gallates into ellagate. Biochemical Journal 67, 445-450.
10. Kahn, V., Andrawis, A., 1985. Inhibition of mushroom tyrosinase by tropolone. Phytochemistry 24, 905-908.
11. Khanbabaee, K., van Ree, T., 2001. Strategies for the synthesis of ellagitannins. Synthesis, 1585-1610.
12. Leech, D., Daigle, F., 1998. Optimisation of a reagentless laccase electrode for the detection of the inhibitor azide. The Analyst 123, 1971-1974.
13. Lewis, N.G., Davin, L.B., 2000. Phenolic coupling in planta: dirigent proteins, dirigent sites and notions beyond randomness. Part 1. Polyphénols Actualités 20, 18-26.
14. Lineweaver, H., Burk, D., 1934. The determination of enzyme dissociation constants. Journal of the American Chemical Society 56, 658-666.
15. Mayer, W., Hoffmann, E.H., Lösch, N., Wolf, H., Wolter, B., Schilling, G., 1984. Dehydrierungsreaktionen mit Gallussäureestern. Liebigs Annalen der Chemie, 929-938.
16. Niehaus, J.U., Gross, G.G., 1997. A gallotannin degrading esterase from leaves of pedunculate oak. Phytochemistry 45, 1555-1560.
17. Niemetz, R., Gross, G.G., 1998. Gallotannin biosynthesis: purification of β-glucogallin: 1,2,3.4,6-pentagalloyl-β-D-glucose galloyltransferase from sumac leaves. Phytochemistry 49, 327-332.
18. Niemetz, R., Schilling, G., Gross, G.G., 2001. Ellagitannin biosynthesis: oxidation of pentagalloylglucose to tellimagrandin II by an enzyme from Tellima grandflora leaves. Chemical Communications, 35-36.
19. Nishizawa, M., Yamagishi, T., Nonaka, T., Nishioka, I., 1980. Structure of gallotannins in Paeoniae radix. Chemical and Pharmaceutical Bulletin 28, 2850-2852.
20. Pedreño, M.-A., Ros Barceló, A., 1999. Inhibition by ferulic acid of the oxidase activity of a cell wall-located basic peroxidase involved in lignification in Z. elegans. International Symposium for Plant Peroxidases, Columbus, Ohio, USA.
21. 14C]-labelled 1,2,3,4,6-penta-O-galloyl-β-D-glucose and related gallotannins. Zeitschrift für Naturforschung 51c, 473-476.
22. Schmidt, O.Th., Mayer, W., 1956. Natürliche Gerbstoffe. Angewandte Chemie 68, 103-115.
23. Tanaka, N., Shimomura, K., Ishimaru, K., 2001. Ellagic acid formation from galloylglucoses by a crude enzyme of Cornus capitata adventitious roots. Bioscience, Biotechnology and Biochemistry 65, 1869-1871.
24. Walker, J.R.L., McCallion, R.F., 1980. The selective inhibition of ortho- and para-diphenol oxidases. Phytochemistry 19, 373-377.