The non-mevalonate isoprenoid biosynthesis of plants as a test system for new herbicides and drugs against pathogenic bacteria and the malaria parasite

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 55, Issue 5-6, 2000, Pages 305-313

  Lichtenthaler, Hartmut K ^a   Zeidler, Johannes ^a   Schwender, Jörg ^a   Müller, Christian ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

1 Deoxy D xylulose 5 Phosphate Pathway; 2 C Methyl D erythritol 4 phosphate; Fosmidomycin; Isopentenyl diphosphate; Isoprene

Indexed keywords

ALGA; ANTIBACTERIAL ACTIVITY; BIOCHEMICAL PATHWAY; BIOSYNTHESIS; FOSMIDOMYCIN; HIGHER PLANT; ISOPRENOID; PLASTID;

MYCOBACTERIUM TUBERCULOSIS; PLASMODIUM FALCIPARUM;

EID: 0033949132     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2000-5-601     Document Type: Article

References (40)

1. Arigoni D., Sagner S., Latzel C., Eisenreich W., Bacher A. and Zenk M. H. (1997), Terpenoid biosynthesis from 1-deoxy-D-xylulose in higher plants by intramolecular skeletal rearrangement. Proc. Natl. Acad. Sci. USA 94, 10600-10605.
2. Bouvier F., d'Harlingue A., Suire C, Backhaus R. A. and Camara B. (1998), Dedicated roles of plastid transketolases during the early onset of isoprenoid biogenesis in pepper fruits. Plant Physiol. 117, 1423-1431.
3. Disch A., Schwender J., Müller C., Lichtenthaler H. K. and Rohmer M. (1998), Distribution of the mevalonate and glyceraldehyde phosphate/pyruvate pathways for isoprenoid biosynthesis in unicellular algae and the cyanobacterium Synechocystis PCC 6714. Biochem. J. 333, 381-388.
4. 5 intermediate in the mevalonate independent pathway for isoprenoid biosynthesis. Tetrahedron Lett. 38, 4769-4772.
5. Fellermeier M., Kis K., Sagner S., Maier U., Bacher A. and Zenk M. H. (1999), Cell-free conversion of 1-deoxy-D-xylulose 5-phosphate and 2-C-methyl-D-erythritol into β-carotene in higher plants and its inhibition by fosmidomycin. Tetrahedron Lett. 40, 2743-2746.
6. Fichera M. E. and Roos D. S. (1997), A plastid organelle as a drug target in apicomplexan parasites. Nature 390, 407-409.
7. Hahn F.M., Hurlburt A. P. and Poulter C. D. (1999), Escherichia coli open reading frame 696 is idi, a nonessential gene encoding isopentenyl diphosphate isomerase. J. Bacteriol. 181, 4499-4504.
8. Harker M. and Bramely P. M. (1999), Expression of prokaryotic 1-deoxy-D-xylulose-5-phosphatases in Escherichia coli increases carotenoid and ubiquinone biosynthesis. FEBS Lett. 448, 115-119.
9. Jomaa H., Wiesner J., Sanderbrand S., Altincicek B., Weidemeyer C., Hintz M., Türbachova I., Eberl M., Zeidler J., Lichtenthaler H. K., Soldati D. and Beck E. (1999), Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs. Science 285, 1573-1576.
10. Kamuro Y., Kawai T. and Kakiuchi T. (1988), Fujisawa Pharmaceutical Co., Ltd., European Patent 0256785B1.
11. Köhler S., Delwiche C. F., Denny P. W., Tilney L. G., Webster P., Wilson R. J. M., Palmer J. D. and Roos D. S. (1997), A plastid of probable green algal origin in apicomplexan parasites. Science 275, 1485-1489.
12. Kuzuyama T., Shimizu T., Takahashi S. and Seto H. (1998), Fosmidomycin, a specific inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in the non-mevalonate pathway for terpenoid biosynthesis. Tetrahedron Lett. 39, 7913-7916.
13. Kuzuyama T., Takagi M., Takahashi S. and Seto H. (2000a), Cloning and characterization of 1-deoxy-D-xylulose 5-phosphate synthase from Streptomyces sp. Strain CL190, which uses both the mevalonate and nonmevalonate pathways fo isopentenyl diphosphate biosynthesis. J. Bacteriol. 182, 891-897.
14. Kuzuyama T., Takagi M., Kaneda K., Dairi T. and Seto H. (2000b), Formation of 4-(cytidine 5′-diphospho)-2-C-methyl-D-erythritol from 2-C-methyl-D-erythritol 4-phosphate by 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, a new enzyme in the nonmevalonate pathway. Tetrahedron Lett. 41, 703-706.
15. Lange B. M. and Croteau R. (1999a), Isoprenoid biosynthesis via a mevalonate-independent pathway in plants: cloning and heterologous expression of 1-deoxy-D-xylulose-5-phosphate reductoisomerase from peppermint. Arch. Biochem. Biophys. 365, 170-174.
16. Lange B. M. and Croteau R. (1999b), Isopentenyl diphosphate biosynthesis via a mevalonate-independent pathway: Isopentenyl monophosphate kinase catalyzes the terminal enzymatic step. Proc. Natl. Acad. Sci. USA 96, 13714-13719.
17. Lange B. M., Wildung M. R., McCaskill D. and Croteau R. (1998), A family of transketolases that directs isoprenoid biosynthesis via a mevalonate-independent pathway. Proc. Natl. Acad. Sci. USA 95, 2100-2104.
18. Lichtenthaler H. K. (1999), The 1-deoxy-d-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 50, 47-65.
19. Lichtenthaler H. K., Schwender J., Seemann M. and Rohmer M. (1995), Carotenoid biosynthesis in green algae proceeds via a novel biosynthetic pathway. In: Photosynthesis: from Light to Biosphere (Mathis P., ed.). Kluwer, Dordrecht, pp. 115-118.
20. Lichtenthaler H. K., Rohmer M. and Schwender J. (1997a), Two independent biochemical pathways for isopentenyl diphosphate biosynthesis in higher plants. Physiol. Plant. 101, 643-652.
21. Lichtenthaler H. K. Schwender J., Disch A. and Rohmer M. (1997b), Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway. FEBS Lett. 400, 271-274.
22. Lois L. M., Campos N., Putra S. R., Danielson K., Rohmer M. and Boronat A. (1998), Cloning and characterization of a gene from Escherichia coli encoding a tranketolase-like enzyme that catalyzes the synthesis of D-1-deoxyxylulose 5-phosphate, a common precursor for isoprenoid, thiamin and pyridoxol biosynthesis. Proc. Natl. Acad. Sci. USA 95, 2105-2110.
23. Lüttgen H., Rohdich F., Herz S., Wungsintaweekul J., Hecht S., Schuhr C. A., Fellermeier M., Sagner S., Zenk M. H., Bacher A. and Eisenreich W. (2000), Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2C-methyl-D-erythritol. Proc. Natl. Acad. Sci. USA 97, 1062-1067.
24. McFadden G. I., Waller R. F., Reith M. E. and Lang-Unasch N. (1997), Plastids in apicomplexan parasites. In: Origin of Algae and their Plastids (Bhattacharya D., ed.). Springer Verlag, Wien, pp. 261-288.
25. Miller B., Heuser T. and Zimmer W. (1999) A Synechococcus leopoliensis SAUG 1402-1 operon harboring the 1-deoxyxylulose 5-phosphate synthase gene and two additional open reading frames is functionally involved in the dimethylallyl diphosphate synthesis. FEBS Lett. 460, 485-490.
26. Ostrovsky D., Diomina G., Lysak E., Matveeva E., Ogrel O. and Trutko S. (1998), Effect of oxidative stress on the biosynthesis of 2-C-methyl-D-erythritol-2,4-cyclopyrophosphate and isoprenoids by several bacterial strains. Arch. Microbiol. 171, 69-72.
27. Patterson D. R. (1987) Rohm and Haas Co., US Patent 4693742.
28. Proteau, P. J. (1998). Biosynthesis of phytol in the cyanobacterium Synechocystis sp. UTEX 2470: utilization of the non-mevalonate pathway. J. Nat. Prod. 61, 841-843.
29. Rohdich F., Wungsintaweekul J., Fellermeier M., Sagner S., Herz S., Kis K., Eisenreich W., Bacher A. and Zenk M. H. (1999), Cytidine 5′-triphosphate-dependent biosynthesis of isoprenoids: YgbP protein of Escherichia coli catalyzes the formation of 4-diphosphocytidyl-2-C-methylerythritol. Proc. Natl. Acad. Sci. USA 96, 11758-11763.
30. Rohmer M. (1999), The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants - Reviewing the litarature published to the end of 1998. Nat. Prod. Rep. 16, 565-574.
31. Rohmer M., Knani M., Simonin P., Sutter B. and Sahm H. (1993). Isoprenoid biosynthesis in bacteria: a novel pathway for early steps leading to isopentenyl diphosphate. Biochem. J. 295, 517-524.
32. Schwender J., Müller C., Zeidler J. and Lichtenthaler H. K. (1999), Cloning and heterologous expression of a cDNA encoding 1-deoxy-D-xylulose-5-phosphate reductoisomerase of Arabidopsis thaliana. FEBS Lett. 455, 140-144.
33. Schwender J., Seemann M., Lichtenthaler H. K. and Rohmer M. (1996), Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliquus. Biochem. J. 316, 73-80.
34. Schwender J., Zeidler J., Gröner R., Müller C., Focke M., Braun S., Lichtenthaler F. W. and Lichtenthaler H. K. (1997), Incorporation of 1-deoxy-D-xylulose into isoprene and phytol by higher plants and algae. FEBS Lett. 414, 129-134.
35. Shigi Y. (1989), Inhibition of bacterial isoprenoid synthesis by fosmidomycin, a phosphonic acid-containing antibiotic. J. Antimicrobial Chemotherapy 24, 131-145.
36. Sprenger G. A., Schörken U., Wiegert T., Grolle S., de Graaf A. A., Taylor S. V., Begley T. P., Bringer-Meyer S. and Sahm H. (1997), Identification of a thiamine-dependent synthase in Escherichia coli required for the formation of the 1-deoxy-D-xylulose-5-phosphate precursor to isoprenoids, thiamin, and pyridoxol. Proc. Natl. Acad. Sci. USA 94, 12857-12862.
37. Takahashi S., Kuzuyama T., Watanabe H. and Seto H. (1998), A 1-deoxy-D-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-D-erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis. Proc. Natl. Acad. Sci. USA 95, 9879-9884.
38. Zeidler J. G. and Lichtenthaler H. K. (1998), Two simple methods for measuring isoprene emission of leaves by UV-spectroscopy and GC-MS. Z. Naturforsch. 53c, 1087-1089.
39. Zeidler J. G., Lichtenthaler H. K., May H. U. and Lichtenthaler F. W. (1997), Is isoprene emitted by plants synthesized via the novel isopentenyl pyrophosphate pathway? Z. Naturforsch. 52c, 15-23.
40. Zeidler J. G., Schwender J., Müller C., Wiesner J., Weidemeyer C., Beck E., Jomaa H. and Lichtenthaler H. K. (1998), Inhibition of the non-mevalonate 1-deoxy-D-xylulose-5-phosphate pathway of plant isoprenoid biosynthesis by fosmidomycin. Z. Naturforsch. 53c. 980-986.