Analysis of metabolic pathways via quantitative prediction of isotope labeling patterns: A retrobiosynthetic 13C NMR study on the monoterpene loganin

Phytochemistry

Volumn 51, Issue 2, 1999, Pages 223-236

  Eichinger, Dietmar ^a   Bacher, Adelbert ^a   Zenk, Meinhart H ^b   Eisenreich, Wolfgang ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

Apocynaceae; Deoxyxylulose pathway; Indole alkaloids; Isoprenoid biosynthesis; Loganin; NMR; Rauwolfia serpentina; Retrobiosynthesis

Indexed keywords

INDOLE ALKALOID; LOGANIN; PLANT EXTRACT; TERPENE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOTOPE LABELING; METABOLISM; NONHUMAN; PLANT;

RAUWOLFIA SERPENTINA;

EID: 0033029538     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(98)00733-X     Document Type: Article

References (41)

1. Arigoni D., Sagner S., Latzel C., Eisenreich W., Bacher A., Zenk M.H. Proc. Natl. Acad. Sci. USA. 94:1997;10600-10605.
2. Bacher, A., Rieder, C., Eichinger, D., Arigoni, D., Fuchs, G., & Eisenreich, W. (1998). FEMS Microbiol. Rev., in press.
3. Banthorpe D.V., Charlwood B.V., Francis M.J.O. Chem. Rev. 72:1972;115-155.
4. Battersby, A. R., Burnett, A. R., Parsons, P. G. (1969). J. Chem. Soc. (C), 1187-1192.
5. Battersby, A. R., Byrne, J. C., Kapil, R. S., Martin, J. A., Payne, T. G., Arigoni, D., Loew, P. (1968). J. Chem. Soc. Chem. Commun., 951-953.
6. Bloch K. Steroids. 57:1992;378-382.
7. Brechbühler-Bader, S., Coscia, C. J., Loew, P., v. Sczepanski, C., Arigoni, D. (1968). J. Chem. Soc. Chem. Commun., 136-137.
8. Broers, S. T. J. (1994). Thesis No. 10978, ETH Zürich, Switzerland.
9. Calis I., Lahloub M.F., Sticher O. Helv. Chim. Acta. 67:1984;160-165.
10. Campos N., Lois L.M., Boronat A. Plant Physiol. 115:1997;1289.
11. Disch A., Schwender J., Müller C., Lichtenthaler H.K., Rohmer M. Biochem. J. 333:1998;381-388.
12. Eisenreich W., Sagner S., Zenk M.H., Bacher A. Tetrahedron Lett. 38:1997;3889-3892.
13. Eisenreich W., Schwarz M., Cartayrade A., Arigoni D., Zenk M.H., Bacher A. Chem. Biol. 5:1998;221-233.
14. Eisenreich W., Schwarzkopf B., Bacher A. J. Biol. Chem. 266:1991;9622-9631.
15. Escher, S., Loew, P., Arigoni, D. (1970). J. Chem. Soc. Chem. Commun., 823-825.
16. Flesch G., Rohmer M. Eur. J. Biochem. 175:1988;405-411.
17. Guarnaccia R., Botta L., Coscia C.J. J. Am. Chem. Soc. 96:1974;7079-7084.
18. Heckendorf A.H., Mattes K.C., Hutchinson C.R., Hagaman E.W., Wenkert E. J. Org. Chem. 41:1976;2045-2047.
19. Jensen S.R., Lyse-Petersen S.E., Nielsen B.J. Phytochemistry. 88:1979;273-277.
20. Lange B.M., Wildung M.R., McCaskill M.R., Croteau D. Proc. Natl. Acad. Sci. USA. 95:1998;2100-2104.
21. Linsmaier E.M., Skoog F. Physiol. Plant. 18:1965;100-127.
22. Lois L.M., Campos N., Putra S.R., Danielsen K., Rohmer M., Boronat A. Proc. Natl. Acad. Sci. USA. 95:1998;2105-2110.
23. Menhard, B. (1998). Biosynthesis of taxans and their elicitation. International Symposium Antitumor Products from Higher Plants, Paris, January 8-10, 1998.
24. Qureshi, N., & Porter, J. W. (1981). In: J. W. Porter, & S. L. Spurgeon. Biosynthesis of isoprenoid compounds, (Vol. 1, pp. 47-94). New York: John Wiley.
25. Ramos-Valdivia A., van der Heijden R., Verpoorte R. Nat. Prod. Rep. 14:1997;591-603.
26. Rohmer M. Prog. Drug. Res. 50:1998;135-154.
27. Rohmer M., Knani M., Simonin P., Sutter B., Sahm H. Biochem. J. 295:1993;517-524.
28. Sagner S., Eisenreich W., Fellermeier M., Latzel C., Bacher A., Zenk M.H. Tetrahedron Lett. 39:1998;2091-2094.
29. Schwarz, M. K. (1994). Thesis No. 10951, ETH Zürich, Switzerland.
30. Schwender J., Lichtenthaler H.K.et al. FEBS Lett. 414:1997;129-134.
31. Shanks J.V., Bhadra R., Morgan J., Rijhwani S. Biotechnol. Bioeng. 58:1998;333-338.
32. Sprenger G.A., Sahm H.et al. Proc. Natl. Acad. Sci. USA. 94:1997;12857-12862.
33. Stöckigt J. Habilitation. 1979;Ruhruniversität Bochum, Germany.
34. Strauß G., Eisenreich W., Bacher A., Fuchs G. Eur. J. Biochem. 205:1992;853-866.
35. Takahashi S., Kuzuyama T., Watanabe H., Seto H. Proc. Natl. Acad. Sci. USA. 95:1998;9879-9884.
36. Tanahashi T., Nagakura N., Inouye H., Zenk M.H. Phytochemistry. 23:1984;1917-1922.
37. Uesato S., Kanomi S., Iida A., Inouye H., Zenk M.H. Phytochemistry. 25:1986;839-842.
38. Verpoorte, R., van der Heijden, R., & Moreno, P. R. H. (1997). In: G. A. Cordell. The alkaloids (Vol. 49, pp. 221-299). New York: Academic Press.
39. Werner I., Bacher A., Eisenreich W. J. Biol. Chem. 272:1997;25474-25482.
40. Whitmer S., Canel C., Hallard D., Gonçalves C., Verpoorte R. Plant Physiol. 116:1998;853-857.
41. Zenk M.H., El-Shagi, Arens H., Stöckigt J., Weiler E.W., Deus B. Barz W., Reinhard E., Zenk M.H. Plant tissue culture and its biotechnological application. 1977;27 Springer, Berlin.