5 Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes and Diterpenes*
Annual Plant Reviews book series, Volume 40: Biochemistry of Plant Secondary Metabolism
Mohamed Ashour,
Michael Wink,
Jonathan Gershenzon,
Mohamed Ashour
Institute of Pharmacy and Molecular Biotechnology, Heidelberg University, Heidelberg, Germany
Search for more papers by this authorMichael Wink
Institute of Pharmacy and Molecular Biotechnology, Heidelberg University, Heidelberg, Germany
Search for more papers by this authorJonathan Gershenzon
Max-Planck-Institute of Chemical Ecology, Jena, Germany
Search for more papers by this authorMohamed Ashour,
Michael Wink,
Jonathan Gershenzon,
Mohamed Ashour
Institute of Pharmacy and Molecular Biotechnology, Heidelberg University, Heidelberg, Germany
Search for more papers by this authorMichael Wink
Institute of Pharmacy and Molecular Biotechnology, Heidelberg University, Heidelberg, Germany
Search for more papers by this authorJonathan Gershenzon
Max-Planck-Institute of Chemical Ecology, Jena, Germany
Search for more papers by this author†
This article was originally published in 2010 in Biochemistry of Plant Secondary Metabolism, Volume 40 (ISBN 9781405183970) of the Annual Plant Reviews book series, this volume edited by Michael Wink. The article was republished in Annual Plant Reviews online in April 2018.
*
This chapter is an update from an earlier version from J. Gershenzon and W. Kreis printed in the first edition in 1999.
Abstract
Terpenoids represent the largest class of secondary metabolites and usually do not contain nitrogen or sulfur in their structures. Many terpenoids serve as defence compounds against microbes and herbivores and/or are signal molecules to attract pollinating insects, fruit-dispersing animals or predators which can destroy insect herbivores. As a consequence, many terpenoids have pronounced pharmacological activities and are therefore interesting for medicine and biotechnology. The first part of the biosynthesis is the generation of a C5 unit, such as isopentenyl diphosphate (IPP) or dimethylallyl diphosphate (DMAPP). Two independent pathways have been discovered that can produce the C5 unit: the mevalonate and the methylerythritol phosphate (MEP) pathway. Depending on the number of C5 units, we distinguish hemiterpenes C5, monoterpenes including iridoids (C10), sesquiterpenes (C15), diterpenes (C20), sesterterpenes (C25), triterpenes (including steroids) (C30), tetraterpenes (C40) and polyterpenes (>C40). The biosynthesis (including enzymes, genes and their regulation) of mevalonate and the methylerythritol phosphate pathway and the consecutive pathways leading to mono-, sesqui- and diterpenes are discussed in this chapter in detail.
References
- Aach, H., Bode, H., Robinson, D.G. and Graebe, J.E. (1997) Ent-kaurene synthase is located in proplastids of meristematic shoot tissues. Planta, 202, 211–9.
- Aach, H., Bose, G. and Graebe, J.E. (1995) Ent-kaurene biosynthesis in a cell-free system from wheat (Triticum aestivum) seedlings and the localisation of ent-kaurene synthetase in plastids of three species. Planta, 197, 333–42.
- Abe, I. (2007) Enzymatic synthesis of cyclic triterpenes. Nat. Prod. Rep., 24, 1311–31.
- Adam, K.P. and Zapp, J. (1998) Biosynthesis of the isoprene units of chamomile sesquiterpenes. Phytochemistry, 48, 953–9.
- Adam, K.P., Thiel, R., Zapp, J. and Becker, H. (1998) Involvement of the mevalonic acid pathway and the glyceraldehyde-pyruvate pathway in terpenoid biosynthesis of the liverworts Ricciocarpos natans and Conocephalum conicum . Arch. Biochem. Biophys., 354, 181–87.
- Adiwilaga, K. and Kush, A. (1996) Cloning and characterization of cDNA encoding farnesyl diphosphate synthase from rubber tree (Hevea brasiliensis). Plant Mol. Biol., 30, 935–46.
- Ait-Ali, T., Swain, S.M., Reid, J.B., Sun, T.P. and Kamiya, Y. (1997) The LS locus of pea encodes the gibberellin biosynthesis enzyme ent-kaurene synthase A. Plant J., 11, 443–54.
- Aitken, S.M., Attucci, S., Ibrahim, R.K. and Gulick, P.J. (1995) A cDNA encoding geranylgeranyl pyrophosphate synthase from white lupin. Plant Physiol., 108, 837–8.
- Aoyagi, K., Beyou, A., Moon, K., Fang, L. and Ulrich, T. (1993) Isolation and characterization of cDNAs encoding wheat 3-hydroxy-3-methylglutaryl coenzyme A reductase. Plant Physiol., 102, 623–8.
- Attucci, S., Aitken, S.M., Gulick, P.J. and Ibrahim, R.K. (1995) Farnesyl pyrophosphate synthase from white lupin: molecular cloning, expression and purification of the expressed protein. Arch. Biochem. Biophys., 321, 493–500.
- Bach, T.J., Boronat, A., Campos, N., Ferrer, A. and Vollack, K.U. (1999) Mevalonate biosynthesis in plants. Crit. Rev. Biochem. Mol. Biol., 34, 107–22.
- Bach, T.J. and Lichtenthaler, H.K. (1983) Inhibition by mevinolin of plant growth, sterol formation and pigment accumulation. Physiol. Plant., 59, 50–60.
- Bach, T.J., Wettstein, A., Boronat, A., Ferrer, A., Enjuto, M., Gruissem, W. and Narita, J.O. (1991) Properties and molecular cloning of plant HMG-CoA reductase, in Physiology and Biochemistry of Sterols (eds G.W. Patterson and W.D. Nes). American Oil Chemists Society, Champaign, IL, pp. 29–49.
- Back, K. and Chappell, J. (1995) Cloning and bacterial expression of a sesquiterpene cyclase from Hyoscyamus muticus and its molecular comparison to related terpene cyclases. J. Biol. Chem., 270, 7375–81.
- Back, K.W. and Chappell, J. (1996) Identifying functional domains within terpene cyclases using a domain-swapping strategy. Proc. Natl. Acad. Sci. USA, 93, 6841–5.
- Badillo, A., Steppuhn, J., Deruere, J., Camara, B. and Kuntz, M. (1995) Structure of a functional geranylgeranyl pyrophosphate synthase gene from Capsicum annuum . Plant Mol. Biol., 27, 425–8.
- Balint, G.A. (2001) Artemisinin and its derivatives: an important new class of antimalarial agents. Pharmacol. Ther., 90, 261–5.
- Bantignies, B., Liboz, T. and Ambid, C. (1996) Nucleotide sequence of a Catharanthus roseus geranylgeranyl pyrophosphate synthase gene. Plant Physiol., 110, 336.
- Belingheri, L., Pauly, G., Gleizes, M. and Marpeau, A. (1988) Isolation by an aqueous two-polymer phase system and identification of endomembranes from Citrofortunella mitis fruits for sesquiterpene hydrocarbon synthesis. J. Plant Physiol., 132, 80–5.
- Bensen, R.J., Johal, G.S., Crane, V.C., Tossberg, J.T., Schnable, P.S., Meeley, R.B. and Briggs, S.P. (1995) Cloning and characterization of the maize An1 gene. Plant Cell, 7, 75–84.
-
Berger, R.G.
(2007)
Flavours and Fragrances Chemistry, Bioprocessing and Sustainability, Vol. XVI.
Springer,
Heidelberg.
10.1007/978-3-540-49339-6 Google Scholar
- Bertea, C.M., Voster, A., Verstappen, F.W., Maffei, M., Beekwilder, J. and Bouwmeester, H.J. (2006) Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. Arch. Biochem. Biophys., 448, 3–12.
- Bestwick, L., Bennett, M.H., Mansfield, J.W. and Rossiter, J.T. (1995) Accumulation of the phytoalexin lettucenin A and changes in 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in lettuce seedlings with the red spot disorder. Phytochemistry, 39, 775–7.
- Bhattacharyya, M.K., Paiva, N.L., Dixon, R.A., Korth, K.L. and Stermer, B.A. (1995) Features of the hmg 1 subfamily of genes encoding HMG-CoA reductase in potato. Plant Mol. Biol., 28, 1–15.
- Bianchini, G.M., Stermer, B.A. and Paiva, N.L. (1996) Induction of early mevalonate pathway enzymes and biosynthesis of end-products in potato (Solanum tuberosum) tubers by wounding and elicitation. Phytochemistry, 42, 1563–71.
- Blanc, V.M. and Pichersky, E. (1995) Nucleotide sequence of a Clarkia breweri cDNA clone of ipi1, a gene encoding isopentenyl pyrophosphate isomerase. Plant Physiol., 108, 855–6.
- Bohlmann, J., Crock, J., Jetter, R. and Croteau, R. (1998a) Terpenoid-based defenses in conifers: cDNA cloning, characterization and functional expression of wound-inducible (E)-α-bisabolene synthase from grand fir (Abies grandis). Proc. Natl. Acad. Sci. USA, 95, 6756–61.
- Bohlmann, J. and Croteau, R. (1999) Diversity and variability of terpenoid defences in conifers: molecular genetics, biochemistry and evolution of the terpene synthase gene family in grand fir (Abies grandis). Novartis Found Symp., 223, 132–49.
- Bohlmann, J., Meyergauen, G. and Croteau, R. (1998b) Plant terpenoid synthases: molecular biology and phylogenetic analysis. Proc. Natl. Acad. Sci. USA, 95, 4126–33.
- Bohlmann, J., Steele, C.L. and Croteau, R. (1997) Monoterpene synthases from grand fir (Abies grandis): cDNA isolation, characterization and functional expression of myrcene synthase, (–)(4S)-limonene synthase and (–)-(1S,5S)-pinene synthase. J. Biol. Chem., 272, 21784–92.
- Bouvier, F., d'Harlingue, A., Suite, 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, 1423–31.
- Bouwmeester, H.J., Kodde, J., Verstappen, F.W., Altug, I.G., de Kraker, J.W. and Wallaart, T.E. (2002) Isolation and characterization of two germacrene A synthase cDNA clones from chicory. Plant Physiol., 129, 134–44.
- Broers, S.T.J. (1994) Ueber die fruehen stufen der biosynthese von isoprenoiden in Escherichia coli. Ph.D. Thesis, Eidgenoessische Technische Hochschule, Zurich.
- Buckingham, J. (2007) Dictionary of Natural Products. Chapman and Hall/CRC, London.
- Burnett, R.J., Maldonado-Mendoza, I.E., McKnight, T.D. and Nessler, C.L. (1993) Expression of a 3-hydroxyl-3-methylglutaryl coenzyme A reductase gene from Camptotheca acuminata is differentially regulated by wounding and methyl jasmonate. Plant Physiol., 103, 41–8.
- Caelles, C., Ferrer, A., Balcells, L., Hegardt, F.G. and Boronat, A. (1989) Isolation and structural characterization of a cDNA encoding Arabidopsis thaliana 3-hydroxy-3-methylglutaryl coenzyme A reductase. Plant Mol. Biol., 13, 627–38.
- Campos, N. and Boronat, A. (1995) Targeting and topology in the membrane of plant 3-hydroxy-3-methylglutaryl coenzyme A reductase. Plant Cell, 7, 2163–74.
- Cane, D.E. (1990) Enzymatic formation of sesquiterpenes. Chem. Rev., 90, 1089–103.
- D.E. Cane (ed.) (1998) Comprehensive Natural Products Chem: Isoprenoid Biosynthesis. Pergamon, Oxford.
- Cao, X., Zong, Z., Ju, X., Sun, Y., Dai, C., Liu, Q. and Jiang, J. (2009) Molecular cloning, characterization and function analysis of the gene encoding HMG-CoA reductase from Euphorbia pekinensis Rupr. Mol. Biol. Rep., Doi:10.1007/s11033–009-9558–7.
- Cartayrade, A., Schwarz, M., Jaun, B. and Arigoni, D. (1994) Detection of two independent mechanistic pathways for the early steps of isoprenoid biosynthesis in Ginkgo biloba , in Second Symposium of the European Network on Plant Terpenoids. Strasbourg, France.
- Chappell, J. (1995) Biochemistry and molecular biology of the isoprenoid biosynthetic pathway in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol., 46, 521–47.
- Chappell, J., von Lanken, C., Vogeli, U. and Bhatt, P. (1989) Sterol and sesquiterpenoid biosynthesis during a growth cycle of tobacco cell suspension cultures. Plant Cell Rep., 8, 848–52.
- Chappell, J., Wolf, F., Proulx, J., Cuellar, R. and Saunders, C. (1995) Is the reaction catalysed by 3-hydroxy-3-methylglutaryl coenzyme A reductase a rate-limiting step for isoprenoid biosynthesis in plants? Plant Physiol., 109, 1337–43.
- Charlwood, B.V. and Banthorpe, D.V. (1978) The biosynthesis of monoterpenes, in Progress in Phytochemistry (eds L. Reinhold, J.B. Harborne and T. Swain). Pergamon, Oxford, pp. 65–125.
- Chen, A., Kroon, P.A. and Poulter, C.D. (1994) Isoprenyl diphosphate synthases: protein sequence comparisons, a phylogenetic tree and predictions of secondary structure. Protein Sci., 3, 600–7.
- Chen, L.J., Lebetkin, E.H. and Burka, L.T. (2001) Metabolism of (R)-(+)-pulegone in F344 rats. Drug Metab. Dispos., 29, 1567–77.
- Chen, X.Y., Chen, Y., Heinstein, P. and Davisson, V.J. (1995) Cloning, expression and characterization of (+)-delta-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis. Arch. Biochem. Biophys., 324, 255–66.
- Chen, X.Y., Wang, M.S., Chen, Y., Davisson, V.J. and Heinstein, P. (1996) Cloning and heterologous expression of a second (+)-delta-cadinene synthase from Gossypium arboreum . J. Nat. Prod., 59, 944–51.
- Choi, D., Bostock, R.M., Avdiushko, S. and Hildebrand, D.F. (1994) Lipid-derived signals that discriminate wound- and pathogen-responsive isoprenoid pathways in plants: methyl jasmonate and the fungal elicitor arachidonic acid induce different 3-hydroxy-3 methylglutaryl-coenzyme A reductase genes and antimicrobial isoprenoids in Solanum tuberosum (L). Proc. Natl. Acad. Sci. USA, 91, 2329–33.
- Choi, D., Ward, B.L. and Bostock, R.M. (1992) Differential induction and suppression of potato 3-hydroxy-3-methylglutaryl coenzyme A reductase genes in response to Phytophthora infestans and to its elicitor arachidonic acid. Plant Cell, 4, 1333–44.
- Christianson, D.W. (2006) Structural biology and chemistry of the terpenoid cyclases. Chem. Rev., 106, 3412–42.
- Clark, G.B., Thompson, G. and Roux, S.J. (2001) Signal transduction mechanisms in plants: an overview. Curr. Sci. 80, 170–77.
- Clastre, M., Bantignies, B., Feron, G., Soler, E. and Ambid, C. (1993) Purification and characterization of geranyl diphosphate synthase from Vitis vinifera L. cv Muscat de Frontignan cell cultures. Plant Physiol., 102, 205–11.
- Colby, S.M., Alonso, W.R., Katahira, E.J., McGarvey, D.J. and Croteau, R. (1993) 4S Limonene synthase from the oil glands of spearmint (Mentha spicata) . J. Biol. Chem., 268, 23016–24.
- Colby, S.M., Crock, J., Dowdlerizzo, B., Lemaux, P.G. and Croteau, R. (1998) Germacrene C synthase from Lycopersicon esculentum cv. Vfnt cherry tomato: cDNA isolation, characterization and bacterial expression of the multiple product sesquiterpene cyclase. Proc. Natl. Acad. Sci. USA, 95, 2216–21.
- Connolly, J.D. and Hill, R.A. (2008) Triterpenoids. Nat. Prod. Rep., 25, 794–830.
- Corey, E.J., Matsuda, S.P.T. and Bartel, B. (1993) Isolation of an Arabidopsis thaliana gene encoding cycloartenol synthase by functional expression in a yeast mutant lacking lanosterol synthase by the use of a chromatographic screen. Proc. Natl. Acad. Sci. USA, 90, 11628–32.
- Cornish, K. (2001) Similarities and differences in rubber biochemistry among plant species. Phytochemistry, 57, 1123–34.
- Crock, J., Wildung, M. and Croteau, R. (1997) Isolation and bacterial expression of a sesquiterpene synthase cDNA clone from peppermint (Mentha x piperita, L.) that produces the aphid alarm pheromone (E)-beta-famesene. Proc. Natl. Acad. Sci. USA, 94, 12833–8.
- Croteau, R. (1987) Biosynthesis and catabolism of monoterpenoids. Chem. Rev., 87, 929–54.
- Croteau, R. and Loomis, W.D. (1972) Biosynthesis of mono- and sesquiterpenes in peppermint from mevalonate-2–14C. Phytochemistry, 11, 1055–66.
- Croteau, R. and Purkett, P.T. (1989) Geranyl pyrophosphate synthase: characterization of the enzyme and evidence that this chain-length specific prenyltransferase is associated with monoterpene biosynthesis in sage (Salvia officinalis). Arch. Biochem. Biophys., 271, 524–35.
- Crowell, D.N. (2000) Functional implications of protein isoprenylation in plants. Prog. Lipid Res., 39, 393–408.
- Cutler, S., Ghassemian, M., Bonetta, D., Cooney, S. and McCourt, P. (1996) A protein, farnesyl transferase, involved in abscisic acid signal transduction in Arabidopsis . Science, 273, 1239–41.
- Dale, S., Arro, M., Becerra, B., Morrice, N.G., Boronat, A., Hardie, D.G. and Ferrer A. (1995) Bacterial expression of the catalytic domain of 3-hydroxy-3-methylglutaryl-CoA reductase (isoform hmgr1) from Arabidopsis thaliana and its inactivation by phosphorylation at ser577 by Brassica oleracea 3-hydroxy-3-methylglutaryl-CoA reductase kinase. Eur. J. Biochem., 233, 506–13.
- Daraselia, N.D., Tarchevskaya, S. and Narita, J.O. (1996) The promoter for tomato 3-hydroxy-3-methylglutaryl coenzyme A reductase gene 2 has unusual regulatory elements that direct high-level expression. Plant Physiol., 112, 727–33.
- D'Auria, J.C. and Gershenzon, J. (2005) The secondary metabolism of Arabidopsis thaliana: growing like a weed. Curr. Opin. Plant Biol., 8, 308–16.
- Davies, T.G., Field, L.M., Usherwood, P.N. and Williamson, M.S. (2007) DDT, pyrethrins, pyrethroids and insect sodium channels. IUBMB Life, 59, 151–62.
- Dekraker, J.W., Franssen, M.C.R., Degroot, A., Konig, W.A. and Bouwmeester, H.J. (1998) (+)-Germacrene A biosynthesis: the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory. Plant Physiol., 117, 1381–92.
- Delourme, D., Lacroute, F. and Karst, F. (1994) Cloning of an Arabidopsis thaliana cDNA coding for farnesyl diphosphate synthase by functional complementation in yeast. Plant Mol. Biol., 26, 1867–73.
- Denbow, C.J., Lang, S. and Cramer, C.L. (1996) The N terminal domain of tomato 3-hydroxy-3-methylglutaryl-CoA reductases: sequence, microsomal targeting and glycosylation. J. Biol. Chem., 271, 9710–5.
- Dewick, P.M. (2002) Medicinal Natural Products: A Biosynthetic Approach, 2nd edn, Wiley, New York.
- Dicke, M. (1994) Local and systemic production of volatile herbivore-induced terpenoids: their role in plant-carnivore mutualism. J. Plant Physiol., 143, 465–72.
- Dicke, M., van Baarlen, P., Wessels, R. and Dijkman, H. (1993) Herbivory induces systemic production of plant volatiles that attract predators of the herbivore: extraction of endogenous elicitor. J. Chem. Ecol., 19, 581–99.
- Dicke, M., van Beek, T.A., Posthumus, M.A., Ben Dom, N., van Bokhoven, H. and de Groot, A. (1990) Isolation and identification of volatile kairomone that affects acarine predatorprey interactions: involvement of host plant in its production. J. Chem. Ecol., 16, 381–96.
- Disch, A., Schwender, J., Muller, 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, 381–8.
- Dogbo, O. and Camara, B. (1987) Purification of isopentenyl pyrophosphate isomerase and geranylgeranyl pyrophosphate synthase from Capsicum chromoplasts by affinity chromatography. Biochim. Biophys. Acta, 920, 140–8.
- Dudareva, N., Cseke, L., Blanc, V.M. and Pichersky, E. (1996) Evolution of floral scent in Clarkia: novel patterns of S-linalool synthase gene expression in the C. breweri flower. Plant Cell, 8, 1137–48.
- Dudareva, N., Pichersky, E. and Gershenzon, J. (2004) Biochemistry of plant volatiles. Plant Physiol., 135, 1893–902.
- Dudley, M.W., Dueber, M.T. and West, C.A. (1986) Biosynthesis of the macrocyclic diterpene casbene in castor bean (Ricinus communis L.) seedlings: changes in enzyme levels induced by fungal infection and intracellular localization of the pathway. Plant Physiol., 81, 335–42.
- Duvold, T., Cali, P., Bravo, J.M. and 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, 6181–4.
- Efferth, T., Li, P.C., Konkimalla, V.S. and Kaina, B. (2007) From traditional Chinese medicine to rational cancer therapy. Trends Mol. Med., 13, 353–61.
- Efferth, T., Romero, M.R., Wolf, D.G., Stamminger, T., Marin, J.J. and Marschall, M. (2008) The antiviral activities of artemisinin and artesunate. Clin. Infect. Dis., 47, 804–11.
- Eisenreich, W., Rohdich, F. and Bacher, A. (2001) Deoxyxylulose phosphate pathway to terpenoids. Trends Plant Sci., 6, 78–84.
- Eisenreich, W., Sagner, S., Zenk, M.H. and Bacher, A. (1997) Monoterpenoid essential oils are not of mevalonoid origin. Tetrahedron Lett., 38, 3889–92.
- Enjuto, M., Balcells, L., Campos, N., Caelles, C., Arro, M. and Boronat, A. (1994) Arabidopsis thaliana contains two differentially expressed 3-hydroxy-3-methylglutaryl-CoA reductase genes, which encode microsomal forms of the enzyme. Proc. Natl. Acad. Sci. USA, 91, 927–931.
- Enjuto, M., Lumbreras, V., Marin, C. and Boronat, A. (1995) Expression of the Arabidopsis hmg2 gene, encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase, is restricted to meristematic and floral tissues. Plant Cell, 7, 517–27.
- Facchini, P.J. and Chappell, J. (1992) Gene family for an elicitor-induced sesquiterpene cyclase in tobacco. Proc. Natl. Acad Sci. USA, 89, 11088–92.
- Fellermeier, M. and Zenk, M.H. (1998) Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEBS Lett., 427, 283–85.
- Flesch, G. and Rohmer, M. (1988) Prokaryotic hopanoids: the biosynthesis of the bacteriohopane skeleton. Formation of isoprenic units from two distinct acetate pools and a novel type of carbon/carbon linkage between triterpenes and d-ribose. Eur. J. Biochem., 175, 405–11.
- Fraga, B.M. (2008) Natural sesquiterpenoids. Nat. Prod. Rep., 25, 1180–1209.
-
Frazier, J.L.
(1986)
The perception of plant allelochemicals that inhibit feeding, in
Molecular Aspects of Insect–Plant Associations (eds
L.B. Brattsten and
S. Ahmad).
Plenum,
New York, pp.
1–42.
10.1007/978-1-4613-1865-1_1 Google Scholar
- Fulton, D.C., Kroon, P.A. and Threlfall, D.R. (1994) Enzymological aspects of the redirection of terpenoid biosynthesis in elicitor-treated cultures of Tabernaemontana divaricata . Phytochemistry, 35, 1183–6.
- Gaisser, S. and Heide, L. (1996) Inhibition and regulation of shikonin biosynthesis in suspension cultures of Lithospermum . Phytochemistry, 41, 1065–72.
- Genschik, P., Criqui, M.-C., Parmentier, Y., Marbach, J., Durr, A., Fleck, J. and Jamet, E. (1992) Isolation and characterization of a cDNA encoding a 3-hydroxy-3-methylglutaryl coenzyme A reductase from Nicotiana sylvestris . Plant Mol. Biol., 20, 337–41.
- Gijzen, M., Lewinsohn, E. and Croteau, R. (1991) Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis). Arch. Biochem. Biophys., 289, 267–73.
- Gondet, L., Bronner, R. and Benveniste, P. (1994) Regulation of sterol content in membranes by subcellular compartmentation of steol-esters accumulating in a sterol-overproducing tobacco mutant. Plant Physiol., 105, 509–18.
- Gondet, L., Weber, T., Maillot-Vernier, P., Benveniste, P. and Bach, T.J. (1992) Regulatory role of microsomal 3-hydroxy-3-methylglutaryl-coenzyme A reductase in a tobacco mutant that overproduces sterols. Biochem. Biophys. Res. Commun., 186, 888–93.
- Gould, M.N. (1995) Prevention and therapy of mammary cancer by monoterpenes. J. Cell. Biochem., Suppl. 22, 139–44.
- Gray, J.C. (1987) Control of isoprenoid biosynthesis in higher plants. Adv. Bot. Res., 14, 25–91.
- Grayson, D.H. (2000) Monoterpenoids. Nat. Prod. Rep., 17, 385–419.
- Guo, Z., Severson, R.F. and Wagner, G.J. (1994) Biosynthesis of the diterpene cis-abienol in cell-free extracts of tobacco trichomes. Arch. Biochem. Biophys., 308, 103–8.
- Hallahan, D.L., Dawson, G.W., West, J.M. and Wallsgrove, R.M. (1992) Cytochrome P450-catalyzed monoterpene hydroxylation in Nepeta mussinii . Plant Physiol. Biochem., 30, 435–43.
- Hallahan, D.L., West, J.M., Smiley, D.W.M. and Pickett, J.A. (1998) Nepetalactol oxidoreductase in trichomes of the catmint Nepeta racemosa . Phytochemistry, 48, 421–7.
- Hallahan, D.L., West, J.M., Wallsgrove, R.M., Smiley, D.W.M., Dawson, G.W., Pickett, J.A. and Hamilton, J.G.C. (1995) Purification and characterization of an acyclic monoterpene primary alcohol-NADP(+) oxidoreductase from catmint (Nepeta racemosa). Arch. Biochem. Biophys., 318, 105–12.
- Hanley, K.M., Voegeli, U. and Chappell, J. (1992) A study of the isoprenoid pathway in elicitortreated tobacco cell suspension cultures, in Secondary-Metabolite Biosynthesis and Metabolism (eds R.J. Petroski and S.P. McCormick). Plenum, New York, pp. 329–36.
- Hanson, J.R. (2005) Diterpenoids. Nat. Prod. Rep., 22, 594–602.
- J.B. Harborne and F.A. Tomas-Barberan (eds) (1991) Ecological Chemistry and Biochemistry of Plant Terpenoids. Clarendon, Oxford, p. 439.
- Harris, C.M. and Poulter, C.D. (2000) Recent studies of the mechanism of protein prenylation. Nat. Prod. Rep., 17, 137–44.
- Hayashi, H., Huang, P., Inoue, K., Hiraoka, N., Ikeshiro, Y., Yazaki, K., Tanaka, S., Kushiro, T., Shibuya, M. and Ebizuka, Y. (2001) Molecular cloning and characterization of isomultiflorenol synthase, a new triterpene synthase from Luffa cylindrica, involved in biosynthesis of bryonolic acid. Eur. J. Biochem., 268, 6311–7.
- Heintze, A., Goerlach, J., Leuschner, C., Hoppe, P., Hagelstein, P., Schulze-Siebert, D. and Schultz, G. (1990) Plastidic isoprenoid synthesis during chloroplast development: change from metabolic autonomy to division-of-labor stage. Plant Physiol., 93, 1121–7.
- Heintze, A., Riedel, A., Aydogdu, S. and Schultz, G. (1994) Formation of chloroplast isoprenoids from pyruvate and acetate by chloroplasts from young spinach plants: evidence for a mevalonate pathway in immature chloroplasts. Plant Physiol. Biochem., 32, 791–7.
- Helliwell, C.A., Sheldon, C.C., Olive, M.R., Walker, A.R., Zeevaart, J.A.D., Peacock, W.J. and Dennis, E.S. (1998) Cloning of the Arabidopsis ent-kaurene oxidase gene ga3 . Proc. Natl. Acad. Sci. USA, 95, 9019–24.
- Hemmerlin, A., Gerber, E., Feldtrauer, J.F., Wentzinger, L., Hartmann, M.A., Tritsch, D., Hoeffler, J.F., Rohmer, M. and Bach, T.J. (2004) A review of tobacco BY-2 cells as an excellent system to study the synthesis and function of sterols and other isoprenoids. Lipids, 39, 723–35.
- Horbach, S., Sahm, H. and Welle, R. (1993) Isoprenoid biosynthesis in bacteria: two different pathways? FEMS Microb. Lett., 111, 135–40.
- Hoshino, T., Yamaura, T., Imaishi, H., Chida, M., Yoshizawa, Y., Higashi, K., Ohkawa, H. and Mizutani, J. (1995) 5-Epi-aristolochene 3-hydroxylase from green pepper. Phytochemistry, 38, 609–13.
- Hugueney, P., Bouvier, F., Badillo, A., Quennemet, J., Dharlingue, A. and Camara, B. (1996) Developmental and stress regulation of gene expression for plastid and cytosolic isoprenoid pathways in pepper fruits. Plant Physiol., 111, 619–26.
- Jansen, B.J.M. and de Groot, A. (2004) Occurrence, biological activity and synthesis of drimane sesquiterpenoids. Nat. Prod. Rep., 21, 449–77.
- Jennewein, S. and Croteau, R. (2001) Taxol: biosynthesis, molecular genetics, and biotechnological applications. Appl. Microbiol. Biotechnol., 57, 13–9.
- Ji, W., Benedict, C.R. and Foster, M.A. (1993) Seasonal variations in rubber biosynthesis, 3-hydroxy-3-methylglutaryl-coenzyme A reductase and rubber transferase activities in Parthenium argentatum in the Chihuahuan Desert. Plant Physiol., 103, 535–42.
- Jiang, J., Kai, G., Cao, X., Chen, F., He, D. and Liu, Q. (2006) Molecular cloning of a HMG-CoA reductase gene from Eucommia ulmoides Oliver. Biosci. Rep., 26, 171–81.
- Joly, A. and Edwards, P.A. (1993) Effect of site-directed mutagenesis of conserved aspartate and arginine residues upon farnesyl diphosphate synthase activity. J. Biol. Chem., 268, 26983–9.
- Joost, O., Bianchini, G., Bell, A.A., Benedict, C.R. and Magill, C.W. (1995) Differential induction of 3-hydroxy-3-methylglutaryl CoA reductase in two cotton species following inoculation with Verticillium . Mol. Plant Microbe Interact, 8, 880–5.
- Kato, H., Kodama, O. and Akatsuka, T. (1995) Characterization of an inducible P450 hydroxylase involved in the rice diterpene phytoalexin biosynthetic pathway. Arch. Biochem. Biophys., 316, 707–12.
- Keeling, C.I. and Bohlmann, J. (2006) Diterpene resin acids in conifers. Phytochemistry, 67, 2415–23.
- Keene, C.K. and Wagner, G.J. (1985) Direct demonstration of duvatrienediol biosynthesis in glandular heads of tobacco trichomes. Plant Physiol., 79, 1026–32.
- Keller, H., Czernic, P., Ponchet, M., Ducrot, P.H., Back, K., Chappell, J., Ricci, P. and Marco, Y. (1998a) Sesquiterpene cyclase is not a determining factor for elicitor-induced and pathogen-induced capsidiol accumulation in tobacco. Planta, 205, 467–76.
- Keller, Y., Bouvier, F., Dharlingue, A. and Camara, B. (1998b) Metabolic compartmentation of plastid prenyllipid biosynthesis: evidence for the involvement of a multifunctional geranylgeranyl reductase. Eur. J. Biochem., 251, 413–7.
- Kim, K.K., Yamashita, H., Sawa, Y. and Shibata, H. (1996) A high activity of 3-hydroxy-3-methylglutaryl coenzyme A reductase in chloroplasts of Stevia rebaudiana Bertoni. Biosci. Biotech. Biochem., 60, 685–6.
- Kim, O.T., Ahn, J.C., Hwang, S. J. and Hwang, B. (2005) Cloning and expression of a farnesyl diphosphate synthase in Centella asiatica (L.) Urban. Mol. Cells, 19, 294–9.
- Kingston, D.G. and Newman, D.J. (2007) Taxoids: cancer-fighting compounds from nature. Curr. Opin. Drug Discov. Devel., 10, 130–44.
- Kleinig, H. (1989) The role of plastids in isoprenoid biosynthesis. Annu. Rev. Plant Physiol. Plant Mol. Biol., 40, 39–59.
- Knoss, W., Reuter, B. and Zapp, J. (1997) Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway. Biochem. J., 326 (Part 2), 449–54.
- Korth, K.L., Stermer, B.A., Bhattacharyya, M.K. and Dixon, R.A. (1997) HMG-CoA reductase gene families that differentially accumulate transcripts in potato tubers are developmentally expressed in floral tissues. Plant Mol. Biol., 33, 545–51.
- Kuntz, M., Roemer, S., Suite, C., Hugueney, P., Weil, J.H., Schantz, R. and Camara, B. (1992) Identification of a cDNA for the plastid-located geranylgeranyl pyrophosphate synthase from Capsicum annuum: correlative increase in enzyme activity and transcript level during fruit ripening. Plant J., 2, 25–34.
- Kuzuyama, T. (2002) Mevalonate and nonmevalonate pathways for the biosynthesis of isoprene units. Biosci. Biotechnol. Biochem., 66, 1619–27.
- Laflamme, P., Khouri, H., Gulick, P. and Ibrahim, R. (1993) Enzymatic prenylation of isoflavones in white lupin. Phytochemistry, 34, 147–51.
- Lange, B.M., Severin, K., Bechthold, A. and Heide, L. (1998a) Regulatory role of microsomal 3-hydroxy-3-methylglutaryl-coenzyme A reductase for shikonin biosynthesis in Lithospermum erythrorhizon cell suspension cultures. Planta, 204, 234–41.
- Lange, B.M., Wildung, M.R., McCaskill, D. and Croteau, R. (1998b) A family of transketolases that directs isoprenoid biosynthesis via a mevalonate-independent pathway. Proc. Natl. Acad. Sci. USA, 95, 2100–4.
- Lange, T., Hedden, P. and Graebe, J.E. (1994) Expression cloning of a gibberellin 20-oxidase, a multifunctional enzyme involved in gibberellin biosynthesis. Proc. Natl. Acad. Sci. USA, 91, 8552–6.
- Langenheim, J.H. (1994) Higher plant terpenoids: a phytocentric overview of their ecological roles. J. Chem. Ecol., 20, 1223–80.
- Laskaris, G., Van Der Heijden, R. and Verpoorte, R. (2000) Purification and partial characterisation of geranylgeranyl diphosphate synthase, from Taxus baccata cell cultures. An enzyme that regulates taxane biosynthesis. Plant Sci., 153, 97–105.
- Learned, R.M. and Fink, G.R. (1989) 3-Hydroxy-3-methylglutaryl-coenzyme A reductase from Arabidopsis thaliana is structurally distinct from the yeast and animal enzymes. Proc. Natl. Acad. Sci. USA, 86, 2779–83.
-
F.J. Leeper and
J.C. Vederas (eds.)
(2000)
Biosynthesis: Aromatic Polyketides, Isoprenoids, Alkaloids. Topics in Current Chemistry.
Springer,
Berlin.
10.1007/3-540-48146-X Google Scholar
- Lerdau, M., Guenther, A. and Monson, R. (1997) Plant production and emission of volatile organic compounds. Bioscience, 47, 373–83.
- Lesburg, C.A., Zhai, G.Z., Cane, D.E. and Christianson, D.W. (1997) Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science, 277, 1820–4.
- Li, C.P. and Larkins, B.A. (1996) Identification of a maize endosperm-specific cDNA encoding farnesyl pyrophosphate synthetase. Gene, 171, 193–6.
- Liao, Z., Chen, M., Gong, Y., Guo, L., Tan, Q., Feng, X., Sun, X., Tan, F., Tang, K. (2004) A new geranylgeranyl diphosphate synthase gene from ginkgo biloba, which intermediates the biosynthesis of the key precursor for ginkgolides mitochondrial DNA. 15, 153–8.
- Lichtenthaler, H.K. (2000) Non-mevalonate isoprenoid biosynthesis: enzymes, genes and inhibitors. Biochem. Soc. Trans., 28, 785–9.
- Lichtenthaler, H.K. (2007) Biosynthesis, accumulation and emission of carotenoids, alpha-tocopherol, plastoquinone, and isoprene in leaves under high photosynthetic irradiance. Photosynth. Res., 92, 163–79.
- Lichtenthaler, H.K., Schwender, J., Disch, A. and Rohmer, M. (1997) Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway. FEBS Lett., 400, 271–4.
- Lim, C.O., Kim, H.Y., Kim, M.G., Lee, S.I., Chung, W.S., Park, S.H., Hwang, I.H. and Cho, M.J. (1996) Expressed sequence tags of Chinese cabbage flower bud cDNA. Plant Physiol., 111, 577–88.
- Lois, L.M., Campos, N., Putra, S.R., Danielsen, K., Rohmer, M. and 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.
- Loreto, F., Forster, A., Durr, M., Csiky, O. and Seufert, G. (1998) On the monoterpene emission under heat stress and on the increased thermotolerance of leaves of Quercus ilex (L.) fumigated with selected monoterpenes. Plant Cell Environ., 21, 101–7.
- Lu, S., Xu, R., Jia, J.W., Pang, J., Matsuda, S.P. and Chen, X.Y. (2002) Cloning and functional characterization of a beta-pinene synthase from Artemisia annua that shows a circadian pattern of expression. Plant Physiol., 130, 477–86.
- Lucker, J., Bowen, P. and Bohlmann, J. (2004) Vitis vinifera terpenoid cyclases: functional identification of two sesquiterpene synthase cDNAs encoding (+)-valencene synthase and (−)-germacrene D synthase and expression of mono- and sesquiterpene synthases in grapevine flowers and berries. Phytochemistry, 65, 2649–59.
- Luetke-Brinkhaus, F. and Kleinig, H. (1987) Formation of isopentenyl diphosphate via mevalonate does not occur within etioplasts and etiochloroplasts of mustard (Sinapis alba L.) seedlings. Planta, 171, 401–6.
- Lunn, J.E. (2007) Compartmentation in plant metabolism. J. Exp. Bot., 58, 35–47.
- Lupien, S., Karp, F., Ponnamperuma, K., Wildung, M. and Croteau, R. (1995) Cytochrome P450 limonene hydroxylases of Mentha species. Drug Metab. Drug Interact., 12, 245–60.
- MacKintosh, R.W., Davies, S.P., Clarke, P.R., Weekes, J., Gillespie, J.G., Gibb, B.J. and Hardie, D.G. (1992) Evidence for a protein kinase cascade in higher plants: 3-hydroxy-3-methylglutaryl-CoA reductase kinase. Eur. J. Biochem., 209, 923–31.
- Maldonado-Mendoza, I.E., Burnett, R.J. and Nessler, C.L. (1992) Nucleotide sequence of a cDNA encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase from Catharanthus roseus . Plant Physiol., 100, 1613–4.
- Maruyama, T., Ito, M. and Honda, G. (2001) Molecular cloning, functional expression and characterization of (E)-beta farnesene synthase from Citrus junos . Biol. Pharm. Bull., 24, 1171–5.
- Matsushita, Y., Kang, W. and Charlwood, B.V. (1996) Cloning and analysis of a cDNA encoding farnesyl diphosphate synthase from Artemisia annua . Gene, 172, 207–9.
- Mau, C.J.D. and West, C.A. (1994) Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants. Proc. Natl. Acad. Sci. USA, 91, 8497–501.
- McCaskill, D. and Croteau, R. (1997) Prospects for the bioengineering of isoprenoid biosynthesis. Adv. Biochem. Eng. Biotechnol., 55, 107–46.
- McKay, S.A., Hunter, W.L., Godard, K.A., Wang, S.X., Martin, D.M., Bohlmann, J. and Plant, A.L. (2003) Insect attack and wounding induce traumatic resin duct development and gene expression of (−)-pinene synthase in Sitka spruce. Plant Physiol., 133, 368–78.
- Mercke, P., Bengtsson, M., Bouwmeester, H.J., Posthumus, M.A. and Brodelius, P.E. (2000) Molecular cloning, expression, and characterization of amorpha-4,11-diene synthase, a key enzyme of artemisinin biosynthesis in Artemisia annua L. Arch. Biochem. Biophys., 381, 173–80.
- Mettal, U., Boland, W., Beyer, P. and Kleinig, H. (1988) Biosynthesis of monoterpene hydrocarbons by isolated chromoplasts from daffodil flowers. Eur. J. Biochem., 170, 613–6.
- Mihaliak, C.A., Karp, F. and Croteau, R. (1993) Cytochrome P450 terpene hydroxylases, in Enzymes of Secondary Metabolism (ed. P.J. Lea). Academic Press, London, pp. 261–79.
- Monfar, M., Caelles, C., Balcells, L., Ferrer, A., Hegardt, F.G. and Boronat, A. (1990) Molecular cloning and characterization of plant 3-hydroxy-3-methylglutaryl coenzyme A reductase, in Biochemistry of the Mevalonic Acid Pathway to Terpenoids (eds G.H.N. Towers and H.A. Stafford). Plenum, New York, pp. 83–97.
- Montamant, F., Guilloton, M., Karst, F. and Delrot, S. (1995) Isolation and characterization of a cDNA encoding Arabidopsis thaliana 3-hydroxy-3-methylglutaryl-coenzyme A synthase. Gene, 167, 197–201.
- Mooibroek, H. and Cornish, K. (2000) Alternative sources of natural rubber. Appl. Microbiol. Biotechnol., 53, 355–65.
- Moreno-Osorio, L., Cortes, M., Armstrong, V., Bailen, M. and Gonzalez-Coloma, A. (2008) Antifeedant activity of some polygodial derivatives. Z. Naturforsch. C, 63, 215–20.
- Muhlenweg, A., Melzer, M., Li, S.M. and Heide, L. (1998) 4-Hydroxybenzoate 3-geranyltransferase from Lithospermum erythrorhizon: purification of a plant membranebound prenyltransferase. Planta, 205, 407–13.
- Nabeta, K., Ishikawa, T., Kawae, T. and Okuyama, H. (1995) Biosynthesis of heteroscyphic acid a in cell cultures of Heteroscyphus planus: nonequivalent labelling of C-5 units in diterpene biosynthesis. J. Chem. Soc: Series Chem. Commun., 6, 681–2.
- Nakagawara, S., Nakamura, N., Guo, Z.-J., Sumitani, K., Katoh, K. and Ohta, Y. (1993) Enhanced formation of a constitutive sesquiterpenoid in cultured cells of a liverwort, Calypogeia granulata Inoue during elicitation: effects of vanadate. Plant Cell Physiol., 34, 421–9.
- Narita, J.O. and Gruissem, W. (1989) Tomato hydroxymethylglutaryl-CoA reductase is required early in fruit development but not during ripening. Plant Cell, 1, 181–90.
- Nelson, A.J., Doerner, P.W., Zhu, Q. and Lamb, C.J. (1994) Isolation of a monocot 3-hydroxy-3-methylglutaryl coenzyme A reductase gene that is elicitor-inducible. Plant Mol. Biol., 25, 401–12.
- Okada, K., Kasahara, H., Yamaguchi, S., Kawaide, H., Kamiya, Y., Nojiri, H. and Yamane, H. (2008) Genetic evidence for the role of isopentenyl diphosphate isomerases in the mevalonate pathway and plant development in Arabidopsis . Plant Cell Physiol., 49, 604–16.
- Oosterhaven, K., Hartmans, K.J. and Huizing, H.J. (1993) Inhibition of potato (Solanum tuberosum) sprout growth by the monoterpene S-carvone: reduction of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity without effect on its mRNA level. J. Plant Physiol., 14, 1463–9.
- Pan, Z.Q., Herickhoff, L. and Backhaus, R.A. (1996) Cloning, characterization and heterologous expression of cDNAs for farnesyl diphosphate synthase from the guayule rubber plant reveals that this prenyltransferase occurs in rubber particles. Arch. Biochem. Biophys., 332, 196–204.
- Panda, T. and Devi, V.A. (2004) Regulation and degradation of HMGCo-A reductase. Appl. Microbiol. Biotechnol., 66, 143–52.
- Pare, P.W. and Tumlinson, J.H. (1997) Induced synthesis of plant volatiles. Nature, 385, 30–1.
- Park, H., Denbow, C.T. and Cramer, C.L. (1992) Structure and nucleotide sequence of tomato HMG2 encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase. Plant Mol. Biol., 20, 327–31.
- Phillips, A.L., Ward, D.A., Uknes, S., Appleford, N.E.J., Lange, T., Huttly, A.K., Gaskin, P., Graebe, J.E. and Hedden, P. (1995) Isolation and expression of three gibberellin 20-oxidase cDNA clones from Arabidopsis . Plant Physiol., 108, 1049–57.
- Phillips, M.A., D'Auria, J.C., Gershenzon, J. and Pichersky, E. (2008) The Arabidopsis thaliana type I Isopentenyl Diphosphate Isomerases are targeted to multiple subcellular compartments and have overlapping functions in isoprenoid biosynthesis. Plant Cell, 20, 677–96.
- Phillips, M.A., Wildung, M.R., Williams, D.C., Hyatt, D.C. and Croteau, R. (2003) cDNA isolation, functional expression, and characterization of (+)-alpha-pinene synthase and (−)-alpha-pinene synthase from loblolly pine (Pinus taeda): stereocontrol in pinene biosynthesis. Arch. Biochem. Biophys., 411, 267–76.
- Pichersky, E., Noel, J.P. and Dudareva, N. (2006) Biosynthesis of plant volatiles: nature's diversity and ingenuity. Science, 311, 808–11.
-
Piel, J.,
Donath, J.,
Bandemer, K. and
Boland, W.
(1998)
Mevalonate-independent biosynthesis of terpenoid volatiles in plants: induced and constitutive emission of volatiles.
Angew. Chem.,
37,
2478–81.
10.1002/(SICI)1521-3773(19981002)37:18<2478::AID-ANIE2478>3.0.CO;2-Q CAS PubMed Web of Science® Google Scholar
- Poulter, C.D. and Rilling, H.C. (1981) Prenyl transferases and isomerase, in Biosynthesis of Isoprenoid Compounds (eds J.W. Porter and S.L. Spurgeon). Wiley, New York, pp. 161–224.
- Prescott, A.G. and John, P. (1996) Dioxygenases: molecular structure and role in plant metabolism. Annu. Rev. Plant Physiol. Plant Mol. Biol., 47, 245–71.
- Qian, D.Q., Zhou, D.F., Ju, R., Cramer, C.L. and Yang, Z.B. (1996) Protein farnesyltransferase in plants: molecular characterization and involvement in cell cycle control. Plant Cell, 8, 2381–94.
- Rajaonarivony, J.I.M., Gershenzon, J. and Croteau, R. (1992) Characterization and mechanism of (4S)-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita). Arch. Biochem. Biophys., 296, 49–57.
- Ramosvaldivia, A.C., Vanderheijden, R. and Verpoorte, R. (1997a) Elicitor-mediated induction of anthraquinone biosynthesis and regulation of isopentenyl diphosphate isomerase and farnesyl diphosphate synthase activities in cell suspension cultures of Cinchona robusta How. Planta, 203, 155–61.
- Ramosvaldivia, A.C., Vanderheijden, R. and Verpoorte, R. (1997b) Isopentenyl diphosphate isomerase, a core enzyme in isoprenoid biosynthesis: a review of its biochemistry and function. Nat. Prod. Rep., 14, 591–603.
- Ramosvaldivia, A.C., Vanderheijden, R. and Verpoorte, R. (1998) Isopentenyl diphosphate isomerase and prenyltransferase activities in rubiaceous and apocynaceous cultures. Phytochemistry, 48, 961–9.
- Ramosvaldivia, A.C., Vanderheijden, R., Verpoorte, R. and Camara, B. (1997c) Purification and characterization of two isoforms of isopentenyl-diphosphate isomerase from elicitor-treated Cinchona robusta cells. Eur. J. Biochem., 249, 161–70.
-
Re, E.B.,
Brugger, S. and
Learned, M.
(1997)
Genetic and biochemical analysis of the transmembrane domain of Arabidopsis 3-hydroxy-3-methylglutaryl coenzyme A reductase.
J. Cell. Biochem.,
65,
443–59.
10.1002/(SICI)1097-4644(19970615)65:4<443::AID-JCB1>3.0.CO;2-O CAS PubMed Web of Science® Google Scholar
- Rieder, C., Strauss, G., Fuchs, G., Arigoni, D., Bacher, A. and Eisenreich, W. (1998) Biosynthesis of the diterpene verrucosan-2-beta-ol in the phototrophic eubacterium Chloroflexus aurantiacus: a retrobiosynthetic NMR study. J. Biol. Chem., 273, 18099–108.
- Riou, C., Tourte, Y., Lacroute, F. and Karst, F. (1994) Isolation and characterization of a cDNA encoding Arabidopsis thaliana mevalonate kinase by genetic complementation in yeast. Gene, 148, 293–7.
- Ro, D.K. and Bohlmann, J. (2006) Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1). Phytochemistry, 67, 1572–8.
- Rohmer, M. (1999) The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Nat. Prod. Rep., 16, 565–74.
- Rohmer, M. (2008) From molecular fossils of bacterial hopanoids to the formation of isoprene units: discovery and elucidation of the methylerythritol phosphate pathway. Lipids, 43, 1095–107.
- Rohmer, M., Seemann, M., Horbach, S., Bringermeyer, S. and 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, 2564–6.
- Rose, U.S.R., Manukian, A., Heath, R.R. and Tumlinson, J.H. (1996) Volatile semiochemicals released from undamaged cotton leaves: a systemic response of living plants to caterpillar damage. Plant Physiol., 111, 487–95.
- Sagner, S., Eisenreich, W., Fellermeier, M., Latzel, C., Bacher, A. and Zenk, M.H. (1998a) Biosynthesis of 2-C-methyl-d-erythritol in plants by rearrangement of the terpenoid precursor, 1-deoxy-d-xylulose 5-phosphate. Tetrahedron Lett., 39, 2091–4.
- Sagner, S., Latzel, C., Eisenreich, W., Bacher, A. and Zenk, M.H. (1998b) Differential incorporation of 1-deoxy-d-xylulose into monoterpenes and carotenoids in higher plants. Chem. Commun., 2, 221–2.
- Sandmann, G. (2001) Carotenoid biosynthesis and biotechnological application. Arch. Biochem. Biophys., 385, 4–12.
- Sandmann, G. and Albrecht, M. (1994) Assays for three enzymes involved in mevalonic acid metabolism. Physiologia Plantarum, 92, 297–301.
- Sando, T., Takaoka, C., Mukai, Y., Yamashita, A., Hattori, M., Ogasawara, N., Fukusaki, E. and Kobayashi, A. (2008) Cloning and characterization of mevalonate pathway genes in a natural rubber producing plant, Hevea brasiliensis . Biosci. Biotechnol. Biochem., 72, 2049–60.
- Sanmiya, K., Iwasaki, T., Matsuoka, M., Miyao, M. and Yamamoto, N. (1997) Cloning of a cDNA that encodes famesyl diphosphate synthase and the blue-light-induced expression of the corresponding gene in the leaves of rice plants. Biochim. Biophys. Acta: Gene Struct. Expr., 1350, 240–6.
- Sasaki, K., Saito, T., Lämsä, M., Oksman-Caldentey, K.M., Suzuki, M. and Ohyama, K. (2007) Plants utilize isoprene emission as a thermotolerance mechanism. Plant Cell Physiol., 48, 1254–62.
- Schaller, H., Grausem, B., Benveniste, P., Chye, M.L., Tan, C.T., Song, C.T. and Chua, N.H. (1995) Expression of the Hevea brasiliensis (hbk) mull arg 3-hydroxy-3-methylglutarylcoenzyme A reductase 1 in tobacco results in sterol overproduction. Plant Physiol., 109, 761–70.
- Schmidt, A. and Gershenzon, J. (2007) Cloning and characterization of isoprenyl diphosphate synthases with farnesyl diphosphate and geranylgeranyl diphosphate synthase activity from Norway spruce (Picea abies) and their relation to induced oleoresin formation. Phytochemistry, 68, 2649–59.
- Schwartz, S.H., Tan, B.C., Gage, D.A., Zeevaart, J.A.D. and McCarty, D.R. (1997) Specific oxidative cleavage of carotenoids by vp14 of maize. Science, 276, 1872–4.
- Schwarz, M.K. (1994) Terpen-Biosynthese in Ginkgo biloba: eine ueberraschende Geschichte. Ph.D. Thesis , Eidgenoessische Technische Hochschule, Zurich.
- Scolnick, P.A- and Bartley, G.E. (1994) Nucleotide sequence of an Arabidopsis cDNA for geranylgeranyl pyrophosphate synthase. Plant Physiol., 104, 1469–70.
- Scolnick, P.A. and Bartley, G.E. (1996) Two more members of an Arabidopsis geranylgeranyl pyrophosphatase synthase gene family. Plant Physiol., 110, 1435.
- Sharkey, T.D. and Yeh, S. (2001) Isoprene emission from plants. Annu Rev Plant Physiol Plant Mol. Biol., 52, 407–36.
- Shen, G., Pang, Y., Wu, W., Liao, Z., Zhao, L., Sun, X. and Tang, K. (2006) Cloning and characterization of a root-specific expressing gene encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase from Ginkgo biloba . Mol. Biol. Rep., 33, 117–27.
- Shibata, H., Sawa, Y., Oka, T., Sonoke, S., Kim, K.K. and Yoshioka, M. (1995) Steviol and steviol-glycoside-glucosyltransferase activities in Stevia rebaudiana Bertoni: purification and partial characterization. Arch. Biochem. Biophys., 321, 390–96.
- Silver, G.M. and Fall, R. (1991) Enzymatic synthesis of isoprene from dimethylallyl diphosphate in aspen leaf extracts. Plant Physiol., 97, 1588–91.
- Silver, G.M. and Fall, R. (1995) Characterization of aspen isoprene synthase, an enzyme responsible for leaf isoprene emission to the atmosphere. J. Biol. Chem., 270, 13010–6.
- Soler, E., Clastre, M., Bantignies, B., Marigo, G. and Ambid, C. (1993) Uptake of isopentenyl diphosphate by plastids isolated from Vitis vinifera (L.) cell suspensions. Planta, 191, 324–9.
- Song, L. and Poulter, C.D. (1994) Yeast farnesyl-diphosphate synthase: site-directed mutagenesis of residues in highly conserved prenyltransferase domains I and II. Proc. Natl. Acad. Sci. USA, 91, 3044–8.
- Sprenger, G.A., Schorken, U., Wiegert, T., Grolle, S., Degraaf, A.A., Taylor, S.V., Begley, T.P., Bringermeyer, S. and Sahm, H. (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, 12857–62.
- Spurgeon, S.L., Sathyamoorthy, N. and Porter, J.W. (1984) Isopentenyl pyrophosphate isomerase and prenyltransferase from tomato fruit plastids. Arch. Biochem. Biophys., 230, 446–54.
- Starks, C.M., Back, K.W., Chappell, J. and Noel, J.P. (1997) Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase. Science, 277, 1815–20.
- Steele, C.L., Crock, J., Bohlmann, J. and Croteau, R. (1998a) Sesquiterpene synthases from grand fir (Abies grandis): comparison of constitutive and wound-induced activities, and cDNA isolation, characterization and bacterial expression of delta-selinene synthase and gamma-humulene synthase. J. Biol. Chem., 273, 2078–89.
- Steele, C.L., Katoh, S., Bohlmann, J. and Croteau, R. (1998b) Regulation of oleoresinosis in grand fir (Abies grandis): differential transcriptional control of monoterpene, sesquiterpene and diterpene synthase genes in response to wounding. Plant Physiol., 116, 1497–504.
- Stermer, B.A., Bianchini, G.M. and Korth, K.L. (1994) Regulation of HMG-CoA reductase activity in plants. J. Lipid Res., 35, 1133–40.
- Stewart, M.J. and Steenkamp, V. (2000) The biochemistry and toxicity of atractyloside: a review. Ther. Drug Monit., 22, 641–9.
- Sun, T.-P. and Kamiya, Y. (1994) The Arabidopsis GAI locus encodes the cyclase ent-kaurene synthetase A of gibberellin biosynthesis. Plant Cell, 6, 1509–18.
- Takahashi, S. and Koyama, T. (2006) Structure and function of cis-prenyl chain elongating enzymes. Chem. Rec., 6, 194–205.
- Tarshis, L.C., Proteau, P.J., Kellogg, B.A., Sacchettini, J.C. and Poulter, C.D. (1996) Regulation of product chain length by isoprenyl diphosphate synthases. Proc. Natl. Acad. Sci. USA, 93, 15018–23.
- Tarshis, L.C., Yan, M., Poulter, C.D. and Sacchettini, J.C. (1994) Crystal structure of recombinant farnesyl diphosphate synthase at 2.6-A resolution. Biochemistry, 33, 10871–7.
- Tello, M., Kuzuyama, T., Heide, L., Noel, J.P. and Richard, S.B. (2008) The ABBA family of aromatic prenyltransferases: broadening natural product diversity. Cell. Mol. Life Sci., 65, 1459–63.
- Thomas, S.G., Rieu, I. and Steber, C.M. (2005) Gibberellin metabolism and signaling. Vitam. Horm., 72, 289–338.
- Turlings, T.C.J., Tumlinson, J.H. and Lewis, W.J. (1990) Exploitation of herbivore-induced plant odors by host-seeking parasitic wasps. Science, 250, 1251–3.
- Turlings, T.C.J., Loughrin, J.H., McCall, P.J., Rose, U.S.R., Lewis, W.J. and Tumlinson, J.H. (1995) How caterpillar-damaged plants protect themselves by attracting parasitic wasps. Proc. Natl. Acad. Sci. USA, 92, 4169–74.
- Turner, G., Gershenzon, J., Nielson, E.E., Froehlich, J.E. and Croteau, R. (1999) Limonene synthase, the enzyme responsible for monoterpene biosynthesis in peppermint, is localized to leucoplasts of oil gland secretory cells. Plant Physiol., 120, 879–86.
- Vogel, B.S., Wildung, M.R., Vogel, G. and Croteau, R. (1996) Abietadiene synthase from grand fir (Abies grandis): cDNA isolation, characterization and bacterial expression of a bifunctional diterpene cyclase involved in resin acid biosynthesis. J. Biol. Chem., 271, 23262–8.
- Vollack, K.U. and Bach, T.J. (1996) Cloning of a cDNA encoding cytosolic acetoacetylcoenzyme A thiolase from radish by functional expression in Saccharomyces cerevisiae . Plant Physiol., 111, 1097–107.
- Vollack, K.-U., Dittrich, B., Ferrer, A., Boronat, A. and Bach, T.J. (1994) Two radish genes for 3-hydroxy-3-methylglutaryl-CoA reductase isozymes complement mevalonate auxotrophy in a yeast mutant and yield membrane-bound active enzyme. J. Plant Physiol., 143, 479–87.
- Wagschal, K., Savage, T.J. and Croteau, R. (1991) Isotopically sensitive branching as a tool for evaluating multiple product formation by monoterpene cyclases. Tetrahedron, 47, 5933–44.
- Wang, K.C. and Ohnuma, S. (2000) Isoprenyl diphosphate synthases. Biochim. Biophys. Acta, 1529, 33–48.
- Wang, P., Liao, Z., Guo, L., Li, W., Chen, M., Pi, Y., Gong, Y., Sun, X. and Tang, K. (2004) Cloning and functional analysis of a cDNA encoding Ginkgo biloba farnesyl diphosphate synthase. Mol. Cells, 18, 150–6.
- Wang, Y., Guo, B., Zhang, F., Yao, H., Miao, Z. and Tang, K. (2007) Molecular cloning and functional analysis of the gene encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase from hazel (Corylus avellana L. Gasaway). J. Biochem. Mol. Biol., 40, 861–9.
- Wanke, M., Skorupinska-Tudek, K. and Swiezewska, E. (2001) Isoprenoid biosynthesis via 1-deoxy-d-xylulose 5-phosphate/2-C-methyl-d-erythritol 4-phosphate (DOXP/MEP) pathway. Acta Biochim. Pol., 48, 663–72.
- Weber, T. and Bach, T.J. (1994) Conversion of acetyl-coenzyme A into 3-hydroxy-3-methylglutarylcoenzyme A in radish seedlings: evidence of a single monomeric protein catalyzing a FeII/quinone-stimulated double condensation reaction. Biochim. Biophys. Acta, 1211, 85–96.
- Wendt, K.U., Poralla, K. and Schulz, G.E. (1997) Structure and function of a squalene cyclase. Science, 277, 1811–5.
- West, C.A. (1981) Biosynthesis of diterpenes, in Biosynthesis of Isoprenoid Compounds (eds J.W. Porter and S.L. Spurgeon). Wiley, New York, pp. 376–411.
- Wettstein, A., Caelles, C., Boronat, A., Jenke, H.-S. and Bach, T.J. (1989) Molecular cloning and characterization of a cDNA encoding radish 3-hydroxy-3-methylglutaryl-CoA reductase. Biol. Chem. Hoppe Seyler, 370, 806–7.
- Wildermuth, M.C. and Fall, R. (1998) Biochemical characterization of stromal and thylakoid-bound isoforms of isoprene synthase in willow leaves. Plant Physiol., 116, 1111–23.
- Wildung, M.R. and Croteau, R. (1996) A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis. J. Biol. Chem., 271, 9201–4.
- Wink, M. (2007) Importance of plant secondary metabolites for protection against insects and microbial infections, in Advances in Phytomedicine, Vol. 3: Naturally Occurring Bioactive Compounds (eds C. Rai and M. Carpinella). Elsevier, Amsterdam, pp. 251–68.
- Wink, M. (2008) Evolutionary advantage and molecular modes of action of multi-component mixtures used in phytomedicine. Curr. Drug Metab., 9, 996–1009.
-
Wink, M.
(2010)
Annual Plant Reviews, Vol. 39: Function and Biotechnology of Plant Secondary Metabolites,
2nd edn.
Wiley-Blackwell,
Oxford.
10.1002/9781444318876 Google Scholar
- M. Wink and B.-E. Wyk (eds) (2008) Mind-Altering and Poisonous Plants of the World. Timber, Portland, OR.
- Winkler, R.G. and Helentjaris, T. (1995) The maize dwarf3 gene encodes a cytochrome P450-mediated early step in gibberellin biosynthesis. Plant Cell, 7, 1307–17.
- Wise, M.L. and Croteau, R. (1998) Monoterpene biosynthesis, in Comprehensive Natural Products Chemistry: Isoprenoid Biosynthesis (ed. D.E. Cane). Pergamon, Oxford.
- Wise, M.L., Savage, T.J., Katahira, E. and Croteau, R. (1998) Monoterpene synthases from common sage (Salvia-officinalis): cDNA isolation, characterization and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase. J. Biol. Chem., 273, 14891–9.
- Wittstock, U. and Gershenzon, J. (2002) Constitutive plant toxins and their role in defense against herbivores and pathogens. Curr. Opin. Plant Biol., 5, 300–7.
- Xu, Y.L., Li, L., Wu, K.Q., Peeters, A.J.M., Gage, D.A. and Zeevaart, J.A.D. (1995) The gas locus of Arabidopsis thaliana encodes a multifunctional gibberellin 20-oxidase: molecular cloning and functional expression. Proc. Natl. Acad. Sci. USA, 92, 6640–4.
- Yamaguchi, S. (2008) Gibberellin metabolism and its regulation. Annu. Rev. Plant Biol., 59, 225–51.
- Yamaguchi, S., Saito, T., Abe, H., Yamane, H., Murofushi, N. and Kamiya, Y. (1996) Molecular cloning and characterization of a cDNA encoding the gibberellin biosynthetic enzyme ent-kaurene synthase B from pumpkin (Cucurbita maxima L). Plant J., 10, 203–13.
- Yamaguchi, S., Sun, T.P., Kawaide, H. and Kamiya, Y. (1998) The ga2 locus of Arabidopsis thaliana encodes ent-kaurene synthase of gibberellin biosynthesis. Plant Physiol, 116, 127–78.
- Yamamoto, H., Senda, M. and Inoue, K. (2000) Flavanone 8-dimethylallyltransferase in Sophora flavescens cell suspension cultures. Phytochemistry, 54, 649–55.
- Yang, Z., Park, H., Lacy, G.H. and Cramer, C.L. (1991) Differential activation of potato 3-hydroxy-3-methylglutaryl coenzyme A reductase genes by wounding and pathogen challenge. Plant Cell, 3, 397–405.
- Youns, M., Efferth, T., Reichling, J., Fellenberg, K., Bauer, A. and Hoheisel, J.D. (2009) Gene expression profiling identifies novel key players involved in the cytotoxic effect of Artesunate on pancreatic cancer cells. Biochem. Pharmacol., 78, 273–83.
- Yu, F., Okamto, S., Nakasone, K., Adachi, K., Matsuda, S., Harada, H., Misawa, N. and Utsumi, R. (2008) Molecular cloning and functional characterization of alpha-humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith). Planta, 227, 1291–9.
- Yuba, A., Yazaki, K., Tabata, M., Honda, G. and Croteau, R. (1996) cDNA cloning, characterization, and functional expression of 4S-(–)-limonene synthase from Perilla frutescens . Arch. Biochem. Biophys., 332, 280–7.
- Zeidler, J.G., Lichtenthaler, H.K., May, H.U. and Lichtenthaler, F.W. (1997) Is isoprene emitted by plants synthesized via a novel isopentenyl pyrophosphate pathway? Z. Naturforsch C, 52, 15–23.
- Zhang, F.L. and Casey, P.J. (1996) Protein prenylation: molecular mechanisms and functional consequences. Annu. Rev. Biochem., 65, 241–69.
- Zhou, D.F., Qian, D.Q., Cramer, C.L. and Yang, Z.B. (1997) Developmental and environmental regulation of tissue- and cell-specific expression for a pea protein farnesyltransferase gene in transgenic plants. Plant J., 12, 921–30.
- Zook, M.N., Chappell, J. and Kuc, J.A. (1992) Characterization of elicitor-induction of sesquiterpene cyclase activity in potato tuber tissue. Phytochemistry, 31, 3441–5.
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