The biosynthesis of lunarine in seeds of Lunaria annua

Phytochemistry

Volumn 47, Issue 3, 1998, Pages 375-387

  Sagner, Silvia ^a   Shen, Zheng Wu ^a   Deus Neumann, Brigitte ^a   Zenk, Meinhart H ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Alkaloid; Biosynthesis; Cruciferae; Cytochrome P 450; Lunaria annua; Lunaridine; Lunarine; Phenol oxidative coupling; Pummerer ketone

Indexed keywords

CYTOCHROME P450; LUNARINE; PARA COUMARIC ACID; PUTRESCINE DERIVATIVE; SPERMIDINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG ISOLATION; DRUG SYNTHESIS; ENZYME ACTIVITY; NONHUMAN; OXIDATION; PLANT SEED; STEREOCHEMISTRY;

LUNARIA ANNUA;

EID: 0032007920     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(97)00590-6     Document Type: Article

References (32)

1. 1. Pummerer, R., Puttfarcken, H. and Schopflocher, P., Berichte, 1925, 58, 1808.
2. 2. Barton, D. H. R., Deflorin, A. M. and Edwards, O. E., Journal of the Chemical Society, 1956, 530.
3. 3. Barton, D. H. R. and Cohen, T. in Festschrift Prof. Dr. Arthur Stoll. Birkhäuser, Basel, 1957, p. 117.
4. 4. Zenk, M. H., Gerardy, R. and Stadler, R., Journal of the Chemical Society, Chemical Communications, 1989, 1725.
5. 5. Gerardy, R. and Zenk, M. H., Phytochemistry, 1993, 32, 79.
6. 6. Stadler, R. and Zenk, M. H., The Journal of Biological Chemistry, 1993, 268, 823.
7. 7. Kraus, P. F. X. and Kutchan, T. M., Proceedings of the National Academy of Sciences of the United States of America, 1995, 92, 2071.
8. 8. Potier, P., Le Men, J., Janot, M.-M. and Bladon, P., Tetrahedron Letters, 1960, 18, 36.
9. 9. Potier, P., Le Men, J., Janot, M.-M., Bladon, P., Brown, A. G. and Wilson, C. S., Tetrahedron Letters, 1963, 5, 293.
10. 10. Jeffreys, J. A. D. and Ferguson, G., Journal of the Chemical Society, 1970, 826.
11. 11. Tamura, C. and Sim, G. A., Journal of the Chemical Society, 1970, 991.
12. 12. Tamura, C., Sim, G. A., Jeffreys, J. A. D., Bladon, P. and Ferguson, G., Journal of the Chemical Society, Chemical Communications, 1965, 20, 485.
13. 13. Poupat, C. and Kunesch, G., Comptes Rendus Hebdomadaires des Séances de l'Académie des Sciences Paris, Série C, 1971, 273, 433.
14. 14. Husson, H.-P., Poupat, C., Rodriguez, B. and Potier, P., Tetrahedron, 1973, 29, 1405.
15. 15. Meurer, B., Wray, V., Wiermann, R. and Strack, D., Phytochemistry, 1988, 27, 839.
16. 16. Werner, C., Hu, W., Lorenzi-Riatsch, A. and Hesse, M., Phytochemistry, 1995, 40, 461.
17. 17. Westerfeld, W. W. and Lowe, C., The Journal of Biological Chemistry, 1942, 145, 463.
18. 18. Janot, M.-M. and Le Men, J., Bulletin de la Société Chimique de France, 1956, 1840.
19. 19. Boit, H.-G., Chemische Berichte, 1954, 87, 1082.
20. 20. Albertson, N. F., in Organic Reactions, Vol. 12, ed. A. C. Cope. Wiley, New York, 1962, p. 205.
21. 21. Schlittler, E., Spitaler, U. and Weber, N., Helvetica Chimica Acta, 1973, 56, 1097.
22. 22. McManis, J. S. and Ganem, B., The Journal of Organic Chemistry, Chemical Communications, 1980, 45, 2041.
23. 23. Nagao, Y., Seno, K., Kawabata, K., Miyasaka, T., Takao, S. and Fujita, E., Chemical and Pharmaceutical Bulletin, 1984, 32, 2687.
24. 24. Kikugawa, Y., Mitsui, K., Sakamoto, T., Kawase, M. and Tamiya, H., Tetrahedron Letters, 1990, 31, 243.
25. 25. Acher, F. and Wakselman, M., The Journal of Organic Chemistry, 1984, 49, 4133.
26. 26. Zaborsky, O. R. and Kaiser, E. T., Journal of the American Chemical Society, 1966, 88, 3084.
27. 27. Corey, E. J. and Venkateswarlu, A., Journal of the American Chemical Society, 1972, 94, 6190.
28. 28. Birecka, H. and Birecki, M., in Methods in Plant Biochemistry, Vol. 9, ed. P. J. Lea, Academic Press, London, 1993, p. 447.
29. 29. Fujii, I., Iijima, H., Tsukita, S., Ebizuka, Y. and Sankawa, U., Journal of Biochemistry, 1987, 101, 11.
30. 30. Huang, K., Fujii, I., Ebizuka, Y., Gomi, K. and Sankawa, U., The Journal of Biological Chemistry, 1995, 270, 21495.
31. 31. Davin, L. B., Bedgar, D. L., Katayama, T. and Lewis, N. G., Phytochemistry, 1992, 31, 3869.
32. 32. Briza, P., Breitenbach, M., Ellinger, A. and Segall, J., Genes and Development, 1990, 4, 1775.