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Isoprenoid Biosynthesis in Plants: Pathways, Genes, Regulation and Metabolic Engineering



Zhi-Hua Liao , Min Chen , Yi-Fu Gong , Zhi-Qi Miao , Xiao-Fen Sun and Ke-Xuan Tang
 
ABSTRACT

Isoprenoids, namely terpenoids, are the largest and the most structurally varied groups of natural products, which contain more than 30,000 known compounds. All the isoprenoids are biosynthesized from only two C5 precursors in plants, isopentenyl diphosphate and its isomer, dimethylallyl diphosphate. Two distinct pathways of isopentenyl diphosphate biosynthesis exist in plants: the classical mevalonate pathway and the recently unveiled deoxyxylulose 5-phosphate pathway. In this study, we summarize the recent progress on the molecular genetics of the two pathways, specializing in pathways, genes, enzymes, intermediates, subcellular compartments of isoprenoid biosynthesis, crosstalk of the two pathways and metabolic regulation and engineering.

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  How to cite this article:

Zhi-Hua Liao , Min Chen , Yi-Fu Gong , Zhi-Qi Miao , Xiao-Fen Sun and Ke-Xuan Tang , 2006. Isoprenoid Biosynthesis in Plants: Pathways, Genes, Regulation and Metabolic Engineering. Journal of Biological Sciences, 6: 209-219.

DOI: 10.3923/jbs.2006.209.219

URL: https://scialert.net/abstract/?doi=jbs.2006.209.219

REFERENCES
Aboushadi, N., W.H. Engfelt, V.G. Paton and S.K. Krisans, 1999. Role of peroxisomes in isoprenoid biosynthesis. J. Histochem. Cytochem., 47: 1127-1132.
Direct Link  |  

Adam, K.P. and J. Zapp, 1998. Biosynthesis of the isoprene units of chamomile sesquiterpenes. Phytochemistry, 48: 953-959.

Albert, J.R., E.C. Olmedo and L.M. Corrochano, 2001. Genes for mevalonate biosynthesis in Phycomyces. Mol. Genet. Gen., 266: 768-777.

Alex, D., T.J. Bach and M.L. Chye, 2000. Expression of Brassica junceaa 3 hydroxy 3 methylglutaryl Co synthase is developmentally regulated and stress responsive. Plant J., 22: 415-426.
Direct Link  |  

Altincicek, B., A.K. Kollas, S. Sanderbrand, J. Wiesner, M. Hintz, E. Beck and H. Jomaa, 2001. GcpE is involved in the 2 C methyl D erythritol 4 phosphate pathway of isoprenoid biosynthesis in Escherichia coli. J. Bacteriol., 183: 2411-2416.

Bach, T.J., 1995. Some new aspects of isoprenoid biosynthesis in plants a review. Lipids, 30: 191-202.
CrossRef  |  

Baker, J., D.B. Franklin and J. Parker, 1992. Sequence and characterization of the gcpE gene of Escherichia coli. FEMS Microbiol. Lett., 73: 175-180.
PubMed  |  

Basson, M.E., M. Thorsness, J.F. Moore, R.M. Stroud and J. Rine, 1988. Structural and functional conservation between yeast and human 3 hydroxy 3 methylglutaryl coenzyme a reductases the rate limiting enzyme of sterol biosynthesis. Mol. Cell. Biol., 8: 3797-3808.
Direct Link  |  

Bick, J.A. and B.M. Lange, 2003. Metabolic crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis Unidirectional transport of intermediates across the chloroplast envelope membrane. Arch. Biochem. Biophys., 415: 146-154.
PubMed  |  

Bouvier, F., A.D. Harlingue, C. Suire, R.A. Backhaus and B. Camara, 1998. Dedicated roles of plastid transketolases during the early onset of isoprenoid biogenesis in pepper fruits. Plant Physiol., 117: 1423-1431.

Caelles, C., A. Ferrer, L. Balcells, F.G. Hegardt and A. Boronat, 1989. Isolation and structural characterization of a cDNA encoding Arabidopsis thaliana 3 hydroxy 3 methylglutaryl coenzyme a reductase. Plant Mol. Biol., 13: 627-638.

Chen, X.Y. and Z.H. Xu, 1996. Recent progress in biotechnology and genetic engineering of medicinal plants in China. Med. Chem. Res., 6: 215-224.

Chye, M.L., C.T. Tan and H.H. Chua, 1992. Three genes encode 3 hydroxy 3 methylglutaryl coenzyme a reductase in Hevea brasiliensis, hmg1 and hmg3 are differentially expressed. Plant Mol. Biol., 19: 473-484.
Direct Link  |  

Cieza, A., P. Maier and E. Poppel, 2003. The effect of Ginkgo Biloba on healthy elderly subjects. Fortschritte Der Medzin, 1: 10-15.
PubMed  |  

Concepeion, M.R., J. Querol, L.M. Lois, S. Imperial and A. Boronat, 2003. Bioinformatic and molecular analysis of hydroxymethylbutenyl diphosphate synthase (GCPE) gene expression during carotenoid accumulation in ripening tomato fruit. Planta, 217: 476-482.

Cordier, H., F. Karst and T. Berges, 1999. Heterologous expression in saccharomyces cerevisiae of an Arabidopsis thaliana cDNA encoding mevalonate diphosphate decarboxylase. Plant Mol. Biol., 39: 953-967.
PubMed  |  

Croteau, R., T.M. Kutchan and N.G. Lewis, 2000. Natural Products (Secondary Metabolites). In: Biochemistry and Molecular Biology of Plants, Buchanan, B.B., W. Gruissem and R.L. Jones (Eds.). American Society of Plant Physiologists, Rockville, Maryland, USA., pp: 1250-1318.

Cunningham, F.X., T.P. Lafond and E. Gantt, 2000. Evidence of a role for LytB in the nonmevalonate pathway of isoprenoid biosynthesis. J. Bacteriol., 182: 5841-5848.

Cunningham, F.X.J. and E. Gantt, 2000. Identification of multi gene families encoding isopentenyl diphosphate isomerase in plants by heterologous complementation in Escherichia coli. Plant Cell. Physiol., 41: 119-123.
Direct Link  |  

Dannert, C.S., D. Umeno and F.H. Arnold, 2000. Molecular breeding of carotenoid biosynthetic pathways. Natl. Biotechnol., 18: 750-753.

Dewick, P.M., 2002. The biosynthesis of C 5 BC 25 terpenoid compounds. Nat. Prod. Rep., 19: 181-222.

Disch, A., A. Hemmerlin, T.J. Bach and M. Rohmer, 1998. Mevalonate derived isopentenyl diphosphate is the biosynthetic precursor of ubiquinone prenyl side chain in tobacco BY 2 cells. Biochem. J., 331: 615-621.

Emori, S.K., K. Higashi, K. Hosoya, T. Kobayashi and H. Ezura, 2001. Cloning and characterization of the gene encoding 3 hydroxy 3 methylglutaryl coenzyme a reductase in melon (Cucumis melo L. Reticulatus). Mol. Genet. Gen., 265: 135-142.
Direct Link  |  

Eriksson, M.E., M. Israelsson, O. Olsson and T. Moritz, 2000. Increased gibberellin biosynthesis in transgenic trees promotes growth, biomass production and xylem fiber length. Nat. Biotechnol., 18: 784-788.
CrossRef  |  Direct Link  |  

Fits, L.V.D. and J. Memelink, 2000. ORCA3 a jasmonate-responsive transcriptional regulator of plant primary and secondary metabolism. Science, 289: 295-297.

Hartmann, T., 1996. Diversity and variability of plant secondary metabolism: A mechanistic view. Entomol. Gen. Appl., 80: 177-188.
CrossRef  |  

Herz, S., J. Wungsintaweekul, C.A. Schuhr, S. Hecht and F. Rohdich et al., 2000. Biosynthesis of terpenoids YgbB protein converts 4 diphosphocytidyl 2C methyl D erythritol 2 phosphate to 2C methyl D erythritol 2 4 cyclodiphosphate. Proc. Natl. Acad. Sci. USA., 97: 2486-2490.
PubMed  |  

Igual, J.C., C.G. Bosch, J. Dopazo and J.E.P. Ortin, 1992. Phylogenetic analysis of the thiolase family implications for the evolutionary origin of peroxisomes. J. Mol. Evol., 35: 147-155.
PubMed  |  

Istvan, E.S. and J. Deisenhofer, 2000. The structure of the catalytic portion of human HMG Coa reductase. Biochem. Biophys. Acta, 1529: 9-18.
PubMed  |  

Jomaa, H., J. Wiesner, S. Sanderbrand, B. Altincicek and H.K. Lichtenthaler et al., 1999. Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs. Science, 285: 1573-1576.

Juan, M., E.A. Cantero, A. Reindl, S. Reichler and P. Leon, 2001. 1 deoxy D xylulose 5 phosphate synthase a limiting enzyme for plastidic isoprenoid biosynthesis in plants. J. Biol. Chem., 276: 22901-22909.
Direct Link  |  

Kishida, H., T. Wada, S. Unzai, T. Kuzuyama and S.Y. Park et al., 2003. Structure and catalytic mechanism of 2 C methyl D erythritol 2 4 cyclodiphosphate (MECDP) synthase an enzyme in the non mevalonate pathway of isoprenoid synthesis. Acta Crystallogr. D. Biol. Crystallogr., 59: 23-31.

Lange, B.M. and R. Croteau, 1999. Genetic engineering of essential oil production in mint. Curr. Opin. Plant Biol., 2: 139-144.

Lange, B.M., R.E.B. Ketchum and R.B. Croteau, 2001. Isoprenoid biosynthesis metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis. Plant Physiol., 127: 305-314.
CrossRef  |  PubMed  |  

Laule, O., A. Furholz, H.S. Chang, T. Zhu, X. Wang and P.B. Heifetz et al., 2003. Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana. Proc. Nat. Acad. Sci. USA., 100: 6866-6871.
Direct Link  |  

Learned, R.M. and G.R. Fink, 1989. 3 Hydroxy 3 methylglutaryl coenzyme a reductase from Arabidopsis thaliana is structurally distinct from the yeast and animal enzymes. Proc. Nat. Acad. Sci. USA., 86: 2779-2783.
Direct Link  |  

Lee, M. and T. Leustek, 1999. Identification of the gene encoding homoserine kinase from Arabidopsis thaliana and characterization of the recombinant enzyme derived from the gene. Arch. Biochem. Biophys., 372: 135-142.

Liao, Z.H., Q.M. Tan, Y.R. Chai, K.J. Zuo and K.X. Tang et al., 2003. Cloning and characterization of the gene encoding HMG Coa reductase from Taxus media and its functional identification in yeast. Funct. Plant Biol., 31: 73-81.
Direct Link  |  

Lluch, M.A., A. Masferrer, M. Arro, A. Boronat and A. Ferrer, 2000. Molecular cloning and expression analysis of the mevalonate kinase gene from Arabidopsis thaliana. Plant Mol. Biol., 42: 365-376.
PubMed  |  

Lois, L.M., M.R. Concepcion, F. Gallego, N. Campos and A. Boronat, 2000. Carotenoid biosynthesis during tomato fruit development regulatory role of 1deoxy D xylulose 5 phosphate synthase. Plant J., 22: 503-513.

Luskey, K.L. and B. Stevens, 1985. Human 3 hydroxy 3 methylglutaryl coenzyme a reductase conserved domains responsible for catalytic activity and sterol regulated degradation. J. Biol. Chem., 260: 10271-10277.
Direct Link  |  

Mann, V., M. Harker, I. Pecker and J. Hirschberg, 2000. Metabolic engineering of astaxanthin production in tobacco flowers. Nat. Biotechnol., 18: 888-892.
Direct Link  |  

Markus L., B., T. Rujan, W. Martin and R. Croteau, 2000. Isoprenoid biosynthesis the evolution of two ancient and distinct pathways across genomes. Proc. Nat. Acad. Sci. USA., 97: 13172-13177.

Martin, V.J.J., D.J. Pitera, S.T. Withers, J.D. Newman and J.D. Keasling, 2003. Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat. Biotech., 21: 796-802.

Matthews, P.D. and E.T. Wurtzel, 2000. Metabolic engineering of carotenoid accumulation in E. coli by modulation of the isoprenoid precursor pool with expression of deoxyxylulose phosphate synthase. Applied Microbiol. Biotechnol., 53: 396-400.

Mendoza, I.E.M., R.J. Burnett and C.L. Nessler, 1992. Nucleotide sequence of a cDNA encoding 3 hydroxy 3 methylglutaryl coenzyme a reductase from Catharanthus roseus. Plant Physiol., 100: 1613-1614.
Direct Link  |  

Mendoza, I.E.M., R.M. Vincent and C.L. Nessler, 1997. Molecular characterization of three differentially expressed members of the Camptotheca acuminata 3 hydroxy 3 methylglutaryl CoA reductase (HMGR) gene family. Plant Mol. Biol., 34: 781-790.

Montamat, F., M. Guilloton, F. Karst and S. Delrot, 1995. Isolation and characterization of a cDNA encoding Arabidopsis thaliana 3 hydroxy 3 methylglutaryl coenzyme a synthase. Gene, 167: 197-201.

Okuhara, M., Y. Kuroda, T. Goto, M. Okamoto and H. Imanaka et al., 1980. Studies on new phosphonic acid antibiotics III Isolation and characterization of FR 31564 FR 32863 and FR 33289 So DXR is the new target protein for developing new herbicides. J. Antibiot., 33: 24-28.

Paganon, S.D., J. Magrath and R.H. Abeles, 1994. Mechanism of mevalonate pyrophosphate decarboxylase evidence for a carbocationic transition state. Biochemistry, 33: 133551-133562.
PubMed  |  

Page, J.E., G. Hause, M. Raschke, W.Y. Gao, J. Schmidt, M.H. Zenk and T.M. Kutchan, 2004. Functional analysis of the final steps of the 1 Deoxy D xylulose 5 phosphate (DXP) pathway to isoprenoids in plants using virusinduced gene silencing. Plant Physiol., 134: 1401-1413.

Park, H., C.J. Denbow and C.L. Cramer, 1992. Structure and nucleotide sequence of tomato HMG2 encoding 3 hydroxy 3 methyl glutaryl coenzyme a reductase. Plant Mol. Biol., 20: 327-331.
CrossRef  |  

Paulet, L.C., I. Ahumada, N. Cunillera, M.R. Concepcion, A. Ferrer, A. Boronat and N. Campos, 2002. Expression and molecular analysis of the Arabidopsis DXR gene encoding 1 deoxy D xylulose 5 phosphate reductoisomerase the first committed enzyme of the 2 C methyl D erythritol 4 phosphate pathway. Plant Physiol., 129: 1581-1591.
Direct Link  |  

Querol, J., N. Campos, S. Imperial, A. Boronat and M.R. Concepcion, 2002. Functional analysis of the Arabidopsis thaliana GCPE protein involved in plastid isoprenoid biosynthesis. FEBS Lett., 514: 343-346.

Rohdich, F., J. Wungsintaweekul, H. Luttgen, M. Fischer and A. Bacher et al., 2000. Biosynthesis of isoprenoids 4 diphosphocytidyl 2 cmethyl D erythritol kinase from tomato. Proc. Natl. Acad. Sci. USA., 97: 8251-8256.

Rohdich, F., J. Wungsintaweekul, W. Eisenreich, G. Richter and A. Bacher et al., 2000. Biosynthesis of terpenoids 4 diphosphocytidyl 2C methyl D erythritol synthase of Arabidopsis thaliana. Proc. Natl. Acad. Sci. USA., 97: 6451-6456.
Direct Link  |  

Rohdich, F., S. Hecht, K. Gartner, P. Adam and W. Eisenreich et al., 2002. Studies on the nonmevalonate terpene biosynthetic pathway metabolic role of IspH (LytB) protein. Proc. Natl. Acad. Sci. USA., 99: 1158-1163.

Rohmer, M., M. Knani, P. Simonin, B. Sutter and H. Sahm, 1993. Isoprenoid biosynthesis in bacteria a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem. J., 295: 517-524.

Rokosz, L.L., D.A. Boulton, E.A. Butkiewicz, G. Sanyal, M.A. Cueto, P.A. Lachance and J.D. Hermes, 1994. Human cytoplasmic 3 hydroxy 3 methylglutaryl coenzyme a synthase expression purification and characterization of recombinant wild type and Cys(129) mutant enzymes. Arch. Biochem. Biophys., 312: 1-13.
Direct Link  |  

Romer, S., P.D. Fraser, J.W. Kiano, C.A. Shipton, N. Misawa, W. Schuch and P.M. Bramley, 2000. Elevation of the provitamin a content of transgenic tomato plants. Natl. Biotechnol., 18: 666-669.

Schwarz, M.K., 1994. Terpen biosynthese in Ginkgo biloba eine uberraschende Geschichte. Ph.D. Thesis, ETH, Zurich, Switzerland.

Soriente, A., M.M.C.D. Rosa, A. Scettri, G. Sodano, M.C. Terencio, M. Paya and M.J. Alcaraz, 1999. Manoalide. Curr. Med. Chem., 6: 415-431.

Souret, F.D.F., P.J. Weathers and K.K. Wobbe, 2002. The mevalonate independent pathway is expressed in transformed roots of artemisia annua and regulated by light and culture age. In vitro Cell. Dev. Biol. Plant, 38: 581-588.

Sprenger, G.A., U. Schorken, T. Wiegert, S. Grolle and H. Sahm et al., 1997. Identification of a thiamin 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.
Direct Link  |  

Steinbacher, S., J. Kaiser, W. Eisenreich, R. Huber, A. Bacher and F. Rohdich, 2003. Structural basis of fosmidomycin action revealed by the complex with 2 C methyl D erythritol 4 phosphate synthase (IspC) implications for the catalytic mechanism and anti malaria drug development. J. Biol. Chem., 278: 18401-18407.
CrossRef  |  

Suwanmanee, P., N. Sirinupong and W. Suvachittanont, 2004. Regulation of the expression of 3 hydroxy 3 methylglutaryl CoA synthase gene in Hevea brasiliensis (BHK) Mull. Arg. Plant Sci., 166: 531-537.
Direct Link  |  

Suzuki, M., Y. Kamide, N. Nagata, H. Seki and T. Muranaka et al., 2004. Loss of function of 3 hydroxy 3 methylglutaryl coenzyme a reductase 1 (HMG1) in Arabidopsis leads to dwarfing early senescence and male sterility and reduced sterol levels. Plant J., 37: 750-761.
PubMed  |  

Takahashi, S., T. Kuzuyama, H. Watanabe and H. Seto, 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. Nat. Acad. Sci. USA., 95: 9879-9884.

Tsay, Y.H. and G.W. Robinson, 1991. Cloning and characterization of ERG8 an essential gene of Saccharomyces cerevisiae that encodes phosphomevalonate kinase. Mol. Cell Biol., 11: 620-631.
Direct Link  |  

Valdivia, A.C.R., R.V. Heijden and R. Verpoorte, 1997. Isopentenyl diphosphate isomerase a core enzyme in isoprenoid biosynthesis a review of its biochemistry and function. Natl. Prod. Rep., 14: 591-603.
PubMed  |  

Veau, B., M. Courtois, A. Oudin, J.C. Chenieux, M. Rideau and M. Clastre, 2000. Cloning and expression of cDNAs encoding two enzymes of the MEP pathway in Catharanthus roseus. Biochem. Biophys. Acta Gen. St. Exp., 1517: 159-163.

Vollack, K.U. and T.J. Bach, 1996. Cloning of a cDNA encoding cytosolic acetoacetyl coenzyme a thiolase from radish by functional expression in Saccharomyces cerevisiae. Plant Physiol., 111: 1097-1107.
Direct Link  |  

Wang, Y.D., Y.J. Yuan, M. Lu, J.C. Wu and J.L. Jiang, 2003. Inhibitor studies of isopentenyl pyrophosphate biosynthesis in suspension cultures of the new Taxus chinensis var. Mairei. Biotechnol. Applied Biochem., 37: 39-43.

Wani, M.C., H.L. Taylor, M.E. Wall, P. Coggon and A.T. McPhail, 1971. Plant antitumor agents VI the isolation and structure of taxol a novel antileukemic and antitumor agent from us brevifolia. J. Am. Chem. Soc., 93: 2325-2327.
PubMed  |  

Wegener, A., W. Gimbel, T. Werner, J. Hani, D. Ernst and H.J. Sandermann, 1997. Molecular cloning of ozone inducible protein from Pinus sylvestris L. with high sequence similarity to vertebrate 3 hydroxy 3 methylglutaryl Coa synthase. Biochem. Biophys. Acta, 1350: 247-252.
PubMed  |  

Wouters, J., Y. Oudjama, S. Ghosh, V. Stalon, L. Droogmans and E. Oldfield, 2003. Structure and mechanism of action of isopentenylpyrophosphate dimethylallylpyrophosphate isomerase. J. Am. Chem. Soc., 125: 3198-3199.
CrossRef  |  

Ye, X.D., S.A. Babili, A. Kloti, J. Zhang, P. Lucca, P. Beyer and I. Potrykus, 2000. Engineering provitamin a (β-carotene) biosynthetic pathway into (caroteneoidfree) rice endosperm. Science, 287: 303-305.

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