The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants

Annual Review of Plant Biology

Volumn 50, Issue , 1999, Pages 47-65

  Lichtenthaler, Hartmut K ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Carotenoid biosynthesis; Chloroplast metabolism; Isopentenyl diphosphate; Isoprene formation; Non mevalonate IPP formation

Indexed keywords

EID: 0033513375     PISSN: 15435008     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.arplant.50.1.47     Document Type: Article

References (84)

1. Adam KP, Thiel R, Zapp J, Becker H. 1998. Involvement of the mevalonic acid pathway and the glyceraldehyde-pyruvate pathway in terpenoid biosynthesis of the liverworts Riccio carpus natans and Conocephalum conicum. Arch. Biochem. Biophys. 354:181-87
2. Adam KP, Zapp J. 1998. Biosynthesis of the isoprene units of chamomile sesquiterpenes. Phytochemistry 48:653-59
3. Andrews TJ, Kane HJ. 1991. Pyruvate is a by-product of catalysis by ribulosebisphoshate carboxylase/oxygenase. J. Biol. Chem. 266:9447-52
4. Arigoni D, Sagner S, Latzel C, Eisenreich W, Bacher A, Zenk MH. 1997. Terpenoid biosynthesis from 1-deoxy-D-xylulose in higher plants by intramolecular skeletal rearrangement. Proc. Natl. Acad. Sci. USA 94:10600-5
5. Bach TJ, Lichtenthaler HK. 1982. Mevinolin, a highly specific inhibitor of microsomal 3-hydroxy-3-methyl-glutarylcoenzyme A reductase of radish plants. Z. Naturforsch. Teil C 37:46-50
6. Bach TJ, Lichtenthaler HK. 1982. Inhibition of mevalonate biosynthesis and plant growth by the fungal metabolite mevinolin. See Ref. 74b, pp. 515-21
7. Bach TJ, Lichtenthaler HK. 1983. Inhibition by mevinolin of plant growth, sterol formation and pigment accumulation. Physiol. Plant. 59:50-60
8. Bohlmann J, Meyer-Gauen G, Croteau R. 1998. Plant terpenoid synthases: molecular biology and phytogenetic analysis. Proc. Natl. Acad. Sci. USA 95:4126-33
9. 2 into carrot-root preparations. Biochem. J. 76:194-97
10. 2 into lycopene by tomato slices. Biochem. J. 76:1-5
11. 2 is fed to intact leaves. Plant Cell Environ. 16:587-91
12. Disch A, Hemmerlin A, Bach TJ, Rohmer M. 1998. Mevalonate-derived isopentenyl diphoshate is the biosynthetic precursor of ubiquinone prenyl side-chain in tobacco BY-2 cells. Biochem. J. 331:615-21
13. Disch A, Schwender J, Müller C, Lichtenthaler HK, Rohmer M. 1998. Mevalonate versus glyceraldehyde phosphate pathway for isoprenoid biosynthesis in unicellular algae and the cyanobacterium Synechocystis. Biochem. J. 333:381-88
14. Döll M, Schindler S, Lichtenthaler HK, Bach TJ. 1984. Differential inhibition by mevinolin of prenyllipid accumulation in cell suspension cultures of Silybum marianum L. See Ref. 68a, pp. 277-80
15. 5 intermediate in the mevalonate-independent pathway for isoprenoid biosynthesis. Tetrahedron Lett. 38:4769-72
16. Duvold T, Cali P, Bravo JM, Rohmer M. 1997. Incorporation of 2-C-methyl-D-erythritol, a putative isoprenoid precursor in the mevalonate-independent pathway, into ubiquinone and menaquinone of Escherichia coli. Tetrahedron Lett. 38:6181-84
17. Eisenreich W, Menhard B, Hylands PJ, Zenk MH, Bacher A. 1996. Studies on the biosynthesis of taxol: The taxane carbon skeleton is not of mevalonoid origin. Proc. Natl. Acad. Sci. USA 93:6431-36
18. Eisenreich W, Sagner S, Zenk MH, Bacher A. 1997. Monoterpenoid essential oils are not of mevalonate origin. Tetrahedron Lett. 38:3889-92
19. Ford CW. 1981. A new lactone from water-stressed chickpea. Phytochemistry 20:2019-20
20. Gershenzon J, Croteau RB. 1993. Terpenoid biosynthesis: the basic pathway and formation of monoterpenes, sesquiterpenes and diterpenes. See Ref. 48a, pp. 339-88
21. Golz A, Focke M, Lichtenthaler HK. 1994. Inhibitors of de novo fatty acid biosynthesis in higher plants. J. Plant Physiol. 143:426-33
22. 14C]meva-lonic acid into ß-carotene in etiolated maize seedlings. Biochem. J. 68:26-27
23. 14C]mevalonic acid into ß-carotene by illuminated etiolated maize seedlings. Biochem. J. 70:612-17
24. Goodwin TW. 1965. Regulation of terpenoid biosynthesis in higher plants. In Biosynthetic Pathways in Higher Plants, ed. JB Pridham, T Swain, pp. 57-71. London: Academic
25. Goodwin TW. 1977. The prenyllipids of the membranes of higher plants. In Lipids and Lipid Polymers in Higher Plants, ed. M Tevini, HK Lichtenthaler, pp. 29-47. Berlin: Springer-Verlag
26. Goodwin TW. 1981. Biosynthesis of plant sterols and other triterpenoids. See Ref. 70, pp. 444-80
27. Hawkins CF, Borges A, Perham RN. 1989. A common structural motif in thiamin pyrophosphate-binding enzymes. FEBS Lett. 255:77-82
28. Heintze A, Görlach J, Leuschner C, Hoppe P, Hagelstein P, et al. 1990. Plastidic isoprenoid synthesis during chloroplast development. Change from metabolic autonomy to division-of-labor stage. Plant Physiol. 93:1121-22
29. Julliard JH. 1992. Biosynthesis of the pyridoxal ring (vitamin B6) in higher plant chloroplasts and its relationship with the biosynthesis of the thiazol ring (vitamin B1). C.R. Acad. Sci. Ser. 314: 285-90
30. Julliard JH, Douce R. 1991. Biosynthesis of the thiazole moiety of thiamin (vitamin B1) in higher plant chloroplasts. Proc. Natl. Acad. Sci. USA 88:2041-45
31. Knöss W, Reuter B, Zapp J. 1997. Biosynthesis of the labdane diterpene marrubiin in Marubium vulgäre via a nonmevalonate pathway. Biochem. J. 326: 449-54
32. Kringstad R, Singsaas AO, Rusten G, Baekkemoen G, Paulsen BS, Nordal A. 1980. 2-C-methylaldotetronic acid present in plants. Phytochemistry 19:543-45
33. Kuzuyama T, Takahashi S, Watanabe H, Seto H. 1998. Direct formation of 2-methyl-D-erythritol 4-phosphate from 1-deoxy-D-xylulose 5-phosphate by 1-deoxy-D-xylulose 5-phosphate reductoisomerase, a new enzyme in the non-mevalonate pathway to isopentenyl diphosphate. Tetrahedron Lett. 39:4509-12
34. Lange B, Wildung M, McCaskill R, Croteau R. 1998. A family of transketolases that directs isoprenoid biosynthesis via a mevalonate-independent pathway. Proc. Natl. Acad. Sci. USA 95:2100-4;
35. Lichtenthaler HK. 1987. Functional organization of carotenoids and prenylquinones in the photosynthetic membrane. In The Metabolism, Structure and Function of Plant Lipids, ed. P Stumpf, JB Mudd, WD Nes, pp. 63-73. New York: Plenum
36. Lichtenthaler HK. 1993. The plant prenyllipids including carotenoids, chlorophylls and prenylquinones. See Ref. 48a, pp. 427-70
37. Lichtenthaler HK. 1998. The plant's 1-deoxy-D-xylulose-5-phospate pathway for biosynthesis of isoprenoids. Fett/Lipid. 100:128-38
38. 14C-mevalonate. See Ref. 74b, pp. 489-500
39. Lichtenthaler HK, Rohmer M, Schwender J. 1997. Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants. Physiol. Plant. 101:643-52
40. Lichtenthaler HK, Rohmer M, Schwender J, Disch A, Seemann M. 1997. A novel mevalonate-independent pathway for the biosynthesis of carotenoids, phytol and prenyl chain of plastoquinone-9 in green algae and higher plants. See Ref. 74a, pp. 177-79
41. Lichtenthaler HK, Schwender J. 1998. The 1-deoxy-D-xylulose-5-phosphate pathway for biosynthesis of carotenoids and plastidic isoprenoids. See Ref. 56a, pp. 419-24
42. Lichtenthaler HK, Schwender J, Disch A, Rohmer M. 1997. Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate independent pathway. FEBS Lett. 400:271-74
43. Lichtenthaler HK, Schwender J, Seemann M, Rohmer M. 1995. Carotenoid biosynthesis in green algae proceeds via a novel biosynthetic pathway. See Ref. 47a, pp. 115-18
44. Lois LM, Campos N, Putra SR, Danielsen K, Rohmer M, Boronat A. 1998. Cloning and characterization of a gene from Escherichia coli encoding a transketolase-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 95:2105-10
45. Lütke-Brinkhaus F, Kleinig H. 1987. Formation of isopentenyl diphosphate via mevalonate does not occur within etioplasts or etiochloroplasts of mustard (Sinapis alba L.) seedlings. Planta 171:401-11
46. Lütke-Brinkhaus F, Liedvogel B, Kleinig H. 1984. On the biosynthesis of ubiquinones in plant mitochondria. Eur. J. Biochem. 141:537-41
47. Maier W, Schneider B, Strack D. 1998. Biosynthesis of sesquiterpenoid cyclohexane derivatives in mycorrhizal barley roots proceeds via the glyceraldehyde-3-phosphate/pyruvate pathway. Tetrahedron Lett. 39:521-24
48. Mandel MA, Feldmann KA, Herrera-Estrella L, Rocha-Sosa M, Leon P. 1996. CLA1, a novel gene required for chloroplast development, is highly conserved in evolution. Plant J. 9:649-58
49. Mathis P, ed. 1995. Photosynthesis: From Light to Biosphere. Amsterdam: Kluwer
50. Meshalkina L, Nilsson U, Wikner C, Kostikowa T, Schneider G. 1997. Examination of thiamin diphosphate binding site in yeast transketolase by site-directed mutagenesis. Eur. J. Biochem. 244:646-52
51. Moore TS, ed. 1993. Lipid Metabolism in Plants. Boca Raton, FL: CRC
52. Müller C, Schwender J, Disch A, Rohmer M, Lichtenthaler FW, Lichtenthaler HK. 1998. Occurrence of the 1-deoxy-D-xylulose-5-phosphate pathway of isopentenyl diphosphate biosynthesis in different algae groups. See Ref. 56a, pp. 425-28
53. 13C labeled acetate and mevalonate in cultured cells of Heteroscyphus planus. J. Chem. Soc. Perkin. Trans. 1:3111-15
54. 13C-labeled glycin in cultured cells of liverworts Heteroscyphus planus and Lophocolea heterophylla. J. Chem. Soc. Perkin Trans. 1:261-67
55. 2]-D-deoxy-xylulose into ubiquinone of Escherichia coli via the mevalonate-independent pathway for isoprenoid biosynthesis. Tetrahedron Lett. 39:23-26
56. Rohmer M, Knani M, Simonin P, Sutter B, Sahm H. 1993. Isoprenoid biosynthesis in bacteria: a novel pathway for early steps leading to isopentenyl diphosphate. Biochem. J. 295:517-24
57. Rohmer M, Seemann M, Horbach S, Bringer-Meyer S, Sahm H. 1996. Glyceraldehyde 3-phosphate and pyruvate as precursors of isoprenic units in an alternative non-mevalonate pathway for terpenoid biosynthesis. J. Am. Chem. Soc. 118:2564-66
58. 13C-labeled glucose in Zymomonas mobilis. J. Chem. Soc. Chem. Commun., pp. 1471-72
59. Sagner S, Eisenreich W, Fellermeier M, Latzel C, Bacher A, Zenk MH. 1998. Biosynthesis of 2-C-methyl-D-erythritol in plants by rearrangement of the terpenoid precursor 1-deoxy-D-xylulose 5-phosphate. Tetrahedron Lett. 39:2091-94
60. Sanchez J, Cerda-Olmedo E, Martinez-Force E, eds. 1998. Advances in Plant Lipid Research. Univ. Sevilla: Secretariado Publ.
61. Schindler S. 1984. Verbreitung und Konzentration von Ubichinon-Homologen in Pflanzen. Karlsr. Contrib. Plant Physiol. 12:1-240
62. Schindler S, Bach TJ, Lichtenthaler HK. 1985. Differential inhibition by mevinolin of prenyllipid accumulation in radish seedlings. Z. Naturforsch. Teil C 40:208-14
63. Schindlet S, Lichtenthaler HK. 1984. Comparison of the ubiquinone homologue pattern in plant mitochondria and their possible prokaryotic ancestors. See Ref. 68a, pp. 273-76
64. Schramm RW, Tomaszewska B, Petersson G. 1979. Sugar-related hydroxy acids from Phaseolus and Trifolium species. Phytochemistry 18:1393-94
65. Schulze-Siebert D, Heinecke D, Scharf H, Schultz G. 1984. Pyruvate derived amino acids in spinach chloroplasts. Plant Physiol. 76:465-71
66. Schwarz MK. 1994. Terpenbiosynthese in Ginkgo biloba. PhD thesis. Eidgenoss. Tech. Hochsch., Zürich
67. 13C-Isotopenmarkierung. Karlsr. Contrib. Plant Physiol. 31:1-85
68. Schwender J, Lichtenthaler HK. 1998. Biosynthesis of lycopene in tomato fruits proceeds via the non-mevalonate isoprenoid pathway. See Ref. 56a, pp. 429-32
69. Schwender J, Lichtenthaler HK, Disch A, Rohmer M. 1997. Biosynthesis of sterols in green algae (Scenedesmus, Chlorella) according to a novel, mevalonate-independent pathway. See Ref. 74a, pp. 180-82
70. Schwender J, Lichtenthaler HK, Seemann M, Rohmer M. 1995. Biosynthesis of isoprenoid chains of chlorophylls and plastoquinone in Scenedesmus by a novel pathway. See Ref. 47a, pp. 1001-4
71. Schwender J, Seemann M, Lichtenthaler HK, Rohmer M. 1996. Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophyll and plastoquinone) via a novel pyruvate/glyceraldehyde-3-phosphate non-mevalonate pathway in the green alga Scenedesmus. Biochem. J. 316:73-80
72. Schwender J, Zeidler J, Gröner R, Müller C, Lichtenthaler HK, et al. 1997. Incorporation of 1-deoxy-D-xylulose into isoprene and phytol by higher plants and algae. FEBS Lett. 414:129-34
73. Siegenthaler PA, Eichenberger W, eds. 1984. Structure, Function and Metabolism of Plant Lipids. Amsterdam: Elsevier
74. Sprenger GA, Schörken U, Wiegert T, Grolle S, de Graaf AA, et al. 1997. Identification of a thiamin-dependent synthase in Escherichia coli required for the formation of 1-deoxy-D-xylulose-5-phosphate precursor to isoprenoids, thiamin, and pyridoxol. Proc. Natl. Acad. Sci. USA 94:12857-62
75. Spurgeon SL, Porter JW. 1981. Introduction. In Biosynthesis of Isoprenoid Compounds, ed. JW Porter, SL Spurgeon, 1:1-46. New York: Wiley
76. Steele JW, Gurin S. 1960. Biosynthesis of ß-carotene in Euglena gracilis. J. Biol. Chem. 235:2778-85
77. Thiel R, Adam KP, Zapp J, Becker H. 1997. Isopentenyl diphosphate biosynthesis in liverworts. Pharm. Pharmacol. Lett. 7:103-5
78. Van den Hoek C, Mann DG, Jahns HM. 1995. Algae, An Introduction to Phycology. Cambridge: Cambridge Univ. Press
79. Wildermuth MC, Fall R. 1996. Light-dependent isoprene emission. Plant Physiol 112:171-82
80. Williams JP, Khan MU, Lem NW, eds. 1997. Physiology, Biochemistry and Molecular Biology of Plant Lipids. Dordrecht: Kluwer
81. Wintermans JFGM, Kuiper PJC, eds. 1982. Biochemistry and Metabolism of Plant Lipids. Amsterdam: Elsevier
82. Zeidler JG, Lichtenthaler HK, May HU, Lichtenthaler FW. 1997. Is isoprene emitted by plants synthesized via the novel isopentenylpyrophosphate pathway? Z. Naturforsch. Teil C 52:15-23
83. Zeidler JG, May HU, Lichtenthaler FW, Lichtenthaler HK. 1998. Isoprene emitted by plants is formed via the 1-deoxy-D-xylulose phosphate pathway of isopentenyl diphosphate biosynthesis. See Ref. 56a, pp. 446-49
84. Zeidler JG, Schwender J, Müller C, Wiesner J, Lichtenthaler HK, et al. 1998. Inhibition of the non-mevalonate 1-deoxy-D-xylulose-5-phosphate pathway of plant isoprenoid biosynthesis by fosmidomycin. Z. Naturforsch. 53C:980-86