(+)-larreatricin hydroxylase, an enantio-specific polyphenol oxidase from the creosote bush (Larrea tridentata)

Proceedings of the National Academy of Sciences of the United States of America

Volumn 100, Issue 19, 2003, Pages 10641-10646

  Cho, Man Ho ^a   Moinuddin, Syed G A ^a   Helms, Gregory L ^a   Hishiyama, Shojiro ^a   Eichinger, Dietmar ^a   Davin, Laurence B ^a   Lewis, Norman G ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL OXIDASE; CREOSOTE; LARREATRICIN HYDROXYLASE; LIGNAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; ENANTIOMER; ENZYME ANALYSIS; ENZYME MECHANISM; ENZYME PURIFICATION; MOLECULAR CLONING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN PROCESSING; STEREOCHEMISTRY;

NON-PROGRAMMATIC;

AMINO ACID SEQUENCE; CATECHOL OXIDASE; CLONING, MOLECULAR; DNA, COMPLEMENTARY; LARREA; MOLECULAR SEQUENCE DATA; SEQUENCE HOMOLOGY, AMINO ACID; STEREOISOMERISM;

LARREA; LARREA TRIDENTATA; TRIDENTATA;

EID: 0141523117     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.1934562100     Document Type: Article

References (47)

1. Train, P., Henrichs, J. R. & Archer, W. A. (1941) Medicinal Uses of Plants by Indian Tribes of Nevada (U.S. Department of Agriculture, Washington, DC).
2. Waller, C. W. & Gisvold, O. (1945) J. Am. Pharm. Assoc. 34, 78-81.
3. Timmermann, B. N. (1977) in Creosote Bush: Biology and Chemistry of Larrea in New World Deserts, eds. Mabry, T. J., Hunziker, J. H. & DiFeo, D. R., Jr. (Dowden, Hutchinson & Ross, Stroudsburg, PA), pp. 252-276.
4. Lundberg, W. O., Halvorson, H. O. & Burr, G. O. (1944) Oil Soap 21, 33-35.
5. Oliveto, E. P. (1972) Chem. Industry 677-679.
6. Belmares, H., Barrera, A., Castillo, E., Ramos, L. F., Hernandez, F. & Hernandez, V. (1979) Ind. Eng. Chem. Prod. Res. Dev. 18, 220-226.
7. Luo, J., Chuang, T., Cheung, J., Quan, J., Tsai, J., Sullivan, C., Hector, R. F., Reed, M. J., Meszaros, K., King, S. R., et al. (1998) Eur. J. Pharmacol. 346, 77-79.
8. Lintner, K. (2000) International Patent WO 2000028959.
9. Elakovich, S. D. & Stevens, K. L. (1985) J. Chem. Ecol, 11, 27-33.
10. McDonald, R. W., Bunjobpon, W., Liu, T., Fessler, S., Pardo, O. E., Freer, I. K., Glaser, M., Seckl, M. J. & Robins, D. J. (2001) Anticancer Drug Des. 16, 261-270.
11. Gnabre, J. N., Brady, J. N., Clanton, D. J., Ito, Y., Dittmer, J., Bates, R. B. & Huang, R. C. C. (1995) Proc. Natl. Acad. Sci. USA 92, 11239-11243.
12. Craigo, J., Callahan, M., Huang, R. C. C. & DeLucia, A. L. (2000) Antiviral Res. 47, 19-28.
13. Gnabre, J. N., Ito, Y., Ma, Y. & Huang, R. C. (1996) J. Chromatogr. A 719, 353-364.
14. Konno, C., Xue, H.-Z., Lu, Z.-Z., Ma, B.-X., Erdelmeier, C. A. J., Che, C.-T., Cordell, G. A., Soejarto, D. D., Waller, D. P. & Fong, H. H. S. (1989) J. Nat. Prod. 52, 1113-1117.
15. Konno, C., Lu, Z.-Z., Xue, H.-Z., Erdelmeier, C. A. J., Meksuriyen, D., Che, C.-T., Cordell, G. A., Soejarto, D. D., Waller, D. P. & Fong, H. H. S. (1990) J. Nat. Prod. 53, 396-406.
16. Moinuddin, S. G. A., Hishiyama, S., Cho, M.-H., Davin, L. B. & Lewis, N. G. (2003) Org. Biomol. Chem. 1, 2307-2313.
17. Croteau, R., Kutchan, T. M. & Lewis, N. G. (2000) in Biochemistry and Molecular Biology of Plants, eds. Buchanan, B. B., Gruissem, W. & Jones, R. L. (Am. Soc. Plant Physiol., Rockville, MD), pp. 1250-1318.
18. Lewis, N. G. & Davin, L. B. (1999) in Comprehensive Natural Products Chemistry, eds. Barton, D. H. R., Nakanishi, K. & Meth-Cohn, O. (Elsevier, London), Vol. 1, pp. 639-712.
19. Davin, L. B., Wang, H.-B., Crowell, A. L., Bedgar, D. L., Martin, D. M., Sarkanen, S. & Lewis, N. G. (1997) Science 275, 362-366.
20. Gang, D. R., Costa, M. A., Fujita, M., Dinkova-Kostova, A. T., Wang, H.-B., Burlat, V., Martin, W., Sarkanen, S., Davin, L. B. & Lewis, N. G. (1999) Chem. Biol. 6, 143-151.
21. Halls, S. C. & Lewis, N. G. (2002) Biochemistry 41, 9455-9461.
22. Butt, V. S. (1977) in Recent Advances in Phytochemistry, eds. Swain, T., Harborne, J. B. & van Sumere, C. F. (Plenum, New York), Vol. 12, pp. 433-456.
23. Kojima, M. & Takeuchi, W. (1989) J. Biochem. 105, 265-270.
24. Billaud, C., Lecornu, D. & Nicolas, J. (1996) J. Agric. Food Chem. 44, 1668-1675.
25. Nakayama, T., Yonekura-Sakakibara, K., Sato, T., Kikuchi, S., Fukui, Y., Fukuchi-Mizutani, M., Ueda, T., Nakao, M., Tanaka, Y., Kusumi, T. & Nishino, T. (2000) Science 290, 1163-1166.
26. Halls, S. C. & Lewis, N. G. (2003) Tetrahedron Assym. 14, 649-658.
27. Bradford, M. M. (1976) Anal. Biochem. 72, 248-254.
28. Eng, J. K., McCormack, A. L. & Yates, J. R., III. (1994) J. Am. Soc. Mass Spectrom. 5, 976-989.
29. Chittum, H. S., Lane, W. S., Carlson, B. A., Roller, P. P., Lung, F. D., Lee, B. J. & Hatfield, D. L. (1998) Biochemistry 37, 10866-10870.
30. Taniguchi, T., Garcia-Higuera, I., Xu, B., Andreassen, P. R., Gregory, R. C., Kim, S. T., Lane, W. S., Kastan, M. B. & D'Andrea, A. D. (2002) Cell 109, 459-472.
31. Cary, J. W., Lax, A. R. & Flurkey, W. H. (1992) Plant Mol. Biol. 20, 245-253.
32. Chevalier, T., de Rigal, D., Richard-Forget, F. & Fils-Lycaon, B. R. (1999) Plant Physiol. 119, 1261-1269.
33. Newman, S. M., Eannetta, N. T., Yu, H., Prince, J. P., de Vincente, M. C., Tanksley, S. D. & Steffens, J. C. (1993) Plant Mol. Biol. 21, 1035-1051.
34. Klabunde, T., Eicken, C., Sacchettini, J. C. & Krebs, B. (1998) Nat. Struct. Biol. 5, 1084-1090.
35. Joy, R. W., IV, Sugiyama, M., Fukuda, H. & Komamine, A. (1995) Plant Physiol. 107, 1083-1089.
36. Gavel, Y. & von Heijne, G. (1990) FEBS Lett. 261, 455-458.
37. Smeekens, S., Bauerle, C., Hageman, J., Keegstra, K. & Weisbeek, P. (1986) Cell 46, 365-375.
38. Lax, A. R. & Vaughn, K. C. (1991) Plant Physiol. 96, 26-31.
39. Rompel, A., Fischer, H., Meiwes, D., Büldt-Karentzopoulos, K., Magrini, A., Eicken, C., Gerdemann, C. & Krebs, B. (1999) FEBS Lett. 445, 103-110.
40. Thipyapong, P., Hunt, M. D. & Steffens, J. C. (1995) Phytochemistry 40, 673-676.
41. Constabel, C. P., Yip, L., Patton, J. J. & Christopher, M. E. (2000) Plant Physiol. 124, 285-295.
42. Vaughan, P. F. T. & Butt, V. S. (1969) Biochem. J. 113, 109-115.
43. Tanaka, M. & Kojima, M. (1991)Arch. Biochem. Biophys. 284, 151-157.
44. Wang, Z.-X., Li, S.-M., Löscher, R. & Heide, L. (1997) Arch. Biochem. Biophys. 347, 249-255.
45. Schoch, G., Goepfert, S., Morant, M., Hehn, A., Meyer, D., Ullmann, P. & Werck-Reichhart, D. (2001) J. Biol. Chem. 276, 36566-36574.
46. Franke, R., Humphreys, J. M., Hemm, M. R., Denault, J. W., Ruegger, M. O., Cusumano, J. C. & Chapple, C. (2002) Plant J. 30, 33-45.
47. Strack, D. & Schliemann, W. (2001)Angew. Chem. Int. Ed. 40, 3791-3794.