Both methylerythritol phosphate and mevalonate pathways contribute to biosynthesis of each of the major isoprenoid classes in young cotton seedlings

Phytochemistry

Volumn 98, Issue , 2014, Pages 110-119

  Opitz, Stefan ^a   Nes, W David ^a,b   Gershenzon, Jonathan ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^b TEXAS TECH UNIVERSITY   (United States)

Author keywords

Carotenoids; Cross talk; Gossypium hirsutum L. (cotton); Isoprenoids; MEP pathway; MVA pathway; Plant biochemistry; Sterols; Terpenoids

Indexed keywords

EMBRYOPHYTA; GOSSYPIUM HIRSUTUM; TRACHEOPHYTA;

MEVALONIC ACID; TERPENE;

CHEMICAL STRUCTURE; CHEMISTRY; GOSSYPIUM; METABOLISM; PLANT LEAF; SEEDLING;

GOSSYPIUM; MEVALONIC ACID; MOLECULAR STRUCTURE; PLANT LEAVES; SEEDLING; TERPENES;

EID: 84892928899     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.11.010     Document Type: Article

References (42)

1. D. Arigoni, S. Sagner, C. Latzel, W. Eisenreich, A. Bacher, and M.H. Zenk Terpenoid biosynthesis from 1-deoxy-d-xylulose in higher plants by intramolecular skeletal rearrangement Proc. Natl. Acad. Sci. USA 94 1997 10600 10605 (Pubitemid 27430780)
2. S. Bartram, A. Jux, G. Gleixner, and W. Boland Dynamic pathway allocation in early terpenoid biosynthesis of stress-induced lima bean leaves Phytochemistry 67 2006 2512
3. J.A. Bick, and B.M. Lange Metabolic cross talk between cytosolic and plastidial pathways of isoprenoid biosynthesis: unidirectional transport of intermediates across the chloroplast envelope membrane Arch. Biochem. Biophys. 415 2003 146 154 (Pubitemid 36794126)
4. J. Buckingham Dictionary of Natural Products 1994 Chapman & Hall London
5. L. Carretero-Paulet, A. Cairo, P. Botella-Pavia, O. Besumbes, N. Campos, A. Boronat, and M. Rodriguez-Concepcion Enhanced flux through the methylerythritol 4-phosphate pathway in Arabidopsis plants overexpressing deoxyxylulose 5-phosphate reductoisomerase Plant Mol. Biol. 62 2006 683 695 (Pubitemid 44652258)
6. N. Dudareva, S. Andersson, I. Orlova, N. Gatto, M. Reichelt, D. Rhodes, W. Boland, and J. Gershenzon The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers Proc. Natl. Acad. Sci. USA 102 2005 933 938 (Pubitemid 40282768)
7. J.M. Estevez, A. Cantero, A. Reindl, S. Reichler, and P. Leon 1-deoxy-d-xylulose-5-phosphate synthase, a limiting enzyme for plastidic isoprenoid biosynthesis in plants J. Biol. Chem. 276 2001 22901 22909
8. U.I. Flugge, and W. Gao Transport of isoprenoid intermediates across chloroplast envelope membranes Plant Biol. 7 2005 91 97 (Pubitemid 40252836)
9. 45 polyprenol, solanesol, in tobacco Biosci. Biotechnol. Biochem. 68 2004 1988 1990 (Pubitemid 39415270)
10. E. Gerber, A. Hemmerlin, M. Hartmann, D. Heintz, M.A. Hartmann, J. Mutterer, M. Rodriguez-Concepcion, A. Boronat, A. Van Dorsselaer, M. Rohmer, D.N. Crowell, and T.J. Bach The plastidial 2-C-methyl-d-erythritol 4-phosphate pathway provides the isoprenyl moiety for protein geranylgeranylation in tobacco BY-2 cells Plant Cell 21 2009 285 300
11. M. Ghassemian, J. Lutes, J.M. Tepperman, H.-S. Chang, T. Zhu, X. Wang, P.H. Quail, and B. Markus Lange Integrative analysis of transcript and metabolite profiling data sets to evaluate the regulation of biochemical pathways during photomorphogenesis Arch. Biochem. Biophys. 448 2006 45 59
12. D. Hampel, A. Mosandl, and M. Wüst Biosynthesis of mono- and sesquiterpenes in strawberry fruits and foliage: H-2 labeling studies J. Agric. Food Chem. 54 2006 1473 1478 (Pubitemid 43374243)
13. D. Hampel, A. Mosandl, and M. Wüst Induction of de novo volatile terpene biosynthesis via cytosolic and plastidial pathways by methyl jasmonate in foliage of Vitis vinifera L J. Agric. Food Chem. 53 2005 2652 2657 (Pubitemid 40471747)
14. D. Hampel, A. Swatski, A. Mosandl, and M. Wüst Biosynthesis of monoterpenes and norisoprenoids in raspberry fruits (Rubus idaeus L.): the role of cytosolic mevalonate and plastidial methylerythritol phosphate pathway J. Agric. Food Chem. 55 2007 9296 9304 (Pubitemid 350105586)
15. A. Hemmerlin, J.L. Harwood, and T.J. Bach A raison d'être for two distinct pathways in the early steps of plant isoprenoid biosynthesis? Prog. Lipid Res. 51 2012 95 148
16. A. Hemmerlin, J.F. Hoeffler, O. Meyer, D. Tritsch, I.A. Kagan, C. Grosdemange-Billiard, M. Rohmer, and T.J. Bach Cross-talk between the cytosolic mevalonate and the plastidial methylerythritol phosphate pathways in Tobacco Bright Yellow-2 cells J. Biol. Chem. 278 2003 26666 26676 (Pubitemid 36876812)
17. A. Hemmerlin, D. Tritsch, M. Hartmann, K. Pacaud, J.F. Hoeffler, A. van Dorsselaer, M. Rohmer, and T.J. Bach A cytosolic Arabidopsis d-xylulose kinase catalyzes the phosphorylation of 1-deoxy-d-xylulose into a precursor of the plastidial isoprenoid pathway Plant Physiol. 142 2006 441 457 (Pubitemid 44583118)
18. 13C isotope ratios: dynamic allocation of resources in induced plants Angew. Chem. Int. Ed. Engl. 40 2001 2091 2093 (Pubitemid 33644325)
19. H. Kasahara, A. Hanada, T. Kuzuyama, M. Takagi, Y. Kamiya, and S. Yamaguchi Contribution of the mevalonate and methylerythritol phosphate pathways to the biosynthesis of gibberellins in Arabidopsis J. Biol. Chem. 277 2002 45188 45194 (Pubitemid 36159122)
20. O. Laule, A. Furholz, H.S. Chang, T. Zhu, X. Wang, P.B. Heifetz, W. Gruissem, and B.M. Lange Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana Proc. Natl. Acad. Sci. USA 100 2003 6866 6871 (Pubitemid 36666671)
21. H.K. Lichtenthaler, J. Schwender, A. Disch, and M. Rohmer Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway FEBS Lett. 400 1997 271 274 (Pubitemid 27039365)
22. J.G. Liu, C.R. Benedict, R.D. Stipanovic, and A.A. Bell Purification and characterization of S-adenosyl-l-methionine: desoxyhemigossypol-6-O- methyltransferase from cotton plants. An enzyme capable of methylating the defense terpenoids of cotton Plant Physiol. 121 1999 1017 1024
23. D. McCaskill, and R. Croteau Monoterpene and sesquiterpene biosynthesis in glandular trichomes of peppermint (Mentha x piperita) rely exclusively on plastid-derived isopentenyl diphosphate Planta 197 1995 49 56
24. O. Meyer, J.F. Hoeffler, C. Grosdemange-Billiard, and M. Rohmer Practical synthesis of 1-deoxy-d-xylulose and 1-deoxy-d-xylulose 5-phosphate allowing deuterium labeling Tetrahedron 60 2004 12153 12162 (Pubitemid 39572649)
25. N. Nagata, M. Suzuki, S. Yoshida, and T. Muranaka Mevalonic acid partially restores chloroplast and etioplast development in Arabidopsis lacking the non-mevalonate pathway Planta 216 2002 345 350 (Pubitemid 36761794)
26. A.K. Neelakandan, S. Chamala, B. Valliyodan, W.D. Nes, and H.T. Nguyen Metabolic engineering of soybean affords improved phytosterol seed traits Plant Biotechnol. J. 10 2012 12 19
27. A.K. Neelakandan, H.T.M. Nguyen, R. Kumar, L.S.P. Tran, S.K. Guttikonda, T.N. Quach, D.L. Aldrich, W.D. Nes, and H.T. Nguyen Molecular characterization and functional analysis of Glycine max sterol methyl transferase 2 genes involved in plant membrane sterol biosynthesis Plant Mol. Biol. 74 2010 503 518
28. W.D. Nes Sterol methyl transferase: enzymology and inhibition Biochim. Biophys. Acta, Mol. Cell. Biol. Lipids 1529 2000 63 88
29. 13C]Mevalonates Phytochemistry 31 1992 805 811
30. S. Opitz, G. Kunert, and J. Gershenzon Increased terpenoid accumulation in cotton (Gossypium hirsutum) foliage is a general wound response J. Chem. Ecol. 34 2008 508 522
31. J. Piel, J. Donath, K. Bandemer, and W. Boland Mevalonate-independent biosynthesis of terpenoid volatiles in plants - induced and constitutive emission of volatiles Angew. Chem. Int. Ed. Engl. 37 1998 2478 2481 (Pubitemid 28485873)
32. L. Pogliani, M. Ceruti, G. Ricchiardi, and D. Viterbo An NMR and molecular mechanics study of squalene and squalene derivatives Chem. Phys. Lipids 70 1994 21 34 (Pubitemid 24129172)
33. M. Rodriguez-Concepcion Early steps in isoprenoid biosynthesis: multilevel regulation of the supply of common precursors in plant cells Phytochem. Rev. 5 2006 1 15 (Pubitemid 44114857)
34. M. Rodriguez-Concepcion, O. Fores, J.F. Martinez-Garcia, V. Gonzalez, M.A. Phillips, A. Ferrer, and A. Boronat Distinct light-mediated pathways regulate the biosynthesis and exchange of isoprenoid precursors during Arabidopsis seedling development Plant Cell 16 2004 144 156 (Pubitemid 38162359)
35. M. Rohmer A mevalonate-independent route to isopentenyl diphosphate D.E. Cane, Comprehensive Natural Products Chemistry vol. 2 1999 Elsevier Oxford 45 67
36. M. Sapir-Mir, A. Mett, E. Belausov, S. Tal-Meshulam, A. Frydman, D. Gidoni, and Y. Eyal Peroxisomal localization of Arabidopsis isopentenyl diphosphate isomerases suggests that part of the plant isoprenoid mevalonic acid pathway is compartmentalized to peroxisomes Plant Physiol. 148 2008 1219 1228 (Pubitemid 352847484)
37. H. Schaller, B. Grausem, P. Benveniste, M.L. Chye, C.T. Tan, C.T. Song, and N.H. Chua Expression of the Hevea brasiliensis (Hbk) Mull Arg 3-hydroxy-3-methylglutaryl-coenzyme A reductase-1 in tobacco results in sterol overproduction Plant Physiol. 109 1995 761 770 (Pubitemid 3009544)
38. C.A. Schuhr, T. Radykewicz, S. Sagner, C. Latzel, M.H. Zenk, D. Arigoni, A. Bacher, F. Rohdich, and W. Eisenreich Quantitative assessment of crosstalk between the two isoprenoid biosynthesis pathways in plants by NMR spectroscopy Phytochem. Rev. 2 2003 3 16 (Pubitemid 39012590)
39. J. Schwender, J. Zeidler, R. Groner, C. Muller, M. Focke, S. Braun, F.W. Lichtenthaler, and H.K. Lichtenthaler Incorporation of 1-deoxy-d-xylulose into isoprene and phytol by higher plants and algae FEBS Lett. 414 1997 129 134 (Pubitemid 27380369)
40. K. Skorupinska-Tudek, J. Poznanski, J. Wojcik, T. Bienkowski, I. Szostkiewicz, M. Zelman-Femiak, A. Bajda, T. Chojnacki, O. Olszowska, J. Grunler, O. Meyer, M. Rohmer, W. Danikiewicz, and E. Swiezewska Contribution of the mevalonate and methylerythritol phosphate pathways to the biosynthesis of dolichols in plants J. Biol. Chem. 283 2008 21024 21035
41. R.D. Stipanovic, D.W. Altman, D.L. Begin, G.A. Greenblatt, and J.H. Benedict Terpenoid aldehydes in upland cottons: analysis by aniline and HPLC methods J. Agric. Food Chem. 36 1988 509 515
42. D. Tritsch, A. Hemmerlin, T.J. Bach, and M. Rohmer Plant isoprenoid biosynthesis via the MEP pathway: in vivo IPP/DMAPP ratio produced by (E)-4-hydroxy-3-methylbut-2-enyl diphosphate reductase in tobacco BY-2 cell cultures FEBS Lett. 584 2010 129 134