5 Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes, Diterpenes, Sterols, Cardiac Glycosides and Steroid Saponins
Annual Plant Reviews book series, Volume 2: Biochemistry of Plant Secondary Metabolism
Jonathan Gershenzon,
Wolfgang Kreis,
Jonathan Gershenzon
Max-Planck-Institut für Chemische Ökologie, Tatzendpromenade la, Jena, D-07745 Germany
Search for more papers by this authorWolfgang Kreis
Lehrstuhl für Pharmazeutische Biologie, FAU Erlangen-Nürnberg, Staudtstrasse 5, Erlangen, D-91058 Germany
Search for more papers by this authorJonathan Gershenzon,
Wolfgang Kreis,
Jonathan Gershenzon
Max-Planck-Institut für Chemische Ökologie, Tatzendpromenade la, Jena, D-07745 Germany
Search for more papers by this authorWolfgang Kreis
Lehrstuhl für Pharmazeutische Biologie, FAU Erlangen-Nürnberg, Staudtstrasse 5, Erlangen, D-91058 Germany
Search for more papers by this authorThis article was originally published in 1998 in Biochemistry of Plant Secondary Metabolism, Volume 2 (ISBN 9781841270074) 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.
Abstract
The sections in this article are
- The Basic Pathway of Terpenoid Biosynthesis and the Formation and Function of C5-C20 Terpenoid Metabolites
- Sterols, Cardiac Glycosides and Steroid Saponins
- Acknowledgements
References
- 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.
- Aach, H., Bode, H., Robinson, D.G. and Graebe, J.E. (1997) Ent-kaurene synthase is located in proplastids of meristematic shoot tissues. Planta, 202 211-19.
- Abe, I., Rohmer, M. and Prestwich, G.D. (1993) Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes. Chem. Rev., 93 2189-206.
- Adam, K.P. and Zapp, J. (1998) Biosynthesis of the isoprene units of chamomile sesquiterpenes. Phytochemistry, 48 953-59.
- Adam, K.P., Crock, J. and Croteau, R. (1996) Partial purification and characterization of a monoterpene cyclase, limonene synthase, from the liverwort Ricciocarpos natans . Arch. Biochem. Biophys., 332 352-56.
- 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., 108 837-38.
- Akhila, A. and Gupta, M.M. (1987) Biosynthesis and translocation of diosgenin in Costus speciosus . J. Plant Physiol., 130 285-90.
- Albrecht, M. and Sandmann, G. (1994) Light-stimulated carotenoid biosynthesis during transformation of maize etioplasts is regulated by increased activity of isopentenyl pyrophosphate isomerase. Plant Physiol., 105 529-34.
- Alfermann, A.W., Bergmann, W., Figur, C., Helmbold, U., Schwantag, D., Schuller, I. and Reinhard, E. (1983) in Plant biotechnology (eds. S.H. Mantell and H. Smith), Society for Experimental Botany, Cambridge University Press, Cambridge, Seminar Series 18, pp. 67-74.
- Anastasia, M. and Ronchetti, F. (1977) Mechanism of 14β-hydroxylation in the biosynthesis of cardenolides: the role of 14β-cholest-5-en-3β-ol. Phytochemistry, 16 1082-83.
- 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., 102 623-28.
- Arigoni, D., Sagner, S., Latzel, C., Eisenreich, W., Bacher, A. and Zenk, M.H. (1997) Terpenoid biosynthesis from 1-deoxy-d-xylulose in higher plants by intramolecular skeletal rearrangement. Proc. Natl. Acad. Sci. USA, 94 10600-605.
- 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. (1995) Some new aspects of isoprenoid biosynthesis in plants: a review. Lipids, 30 191-202.
- Bach, T.J. and Lichtenthaler, H.K. (1983) Inhibition by mevinolin of plant growth, sterol formation and pigment accumulation. Physiologia Plantarum, 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, Illinois, 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 6841-45.
- 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., 27 425-28.
- Bak, S., Kahn, R.A., Olsen, C.E. and Halkier, B.A. (1997) Cloning and expression in Escherichia coli of the obtusifoliol 14α-demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14α-demethylases (CYP51) from fungi and mammals. Plant J., 11 191-201.
- Bantignies, B., Liboz, T. and Ambid, C. (1996) Nucleotide sequence of a Catharanthus roseus geranylgeranyl pyrophosphate synthase gene. Plant Physiol., 110 336.
- Bauer, P., Kopp, B. and Franz, G. (1984) Biosynthese von Herzglykosiden: Nachweis von nukleotidgebundenen 2,6-Didesoxy-3-O-methylhexosen in Blättern von Nerium oleander . Planta Med., 50 12-14.
- Baumann, T., Kreis, W., Mehrle, W., Hampp, R. and Reinhard, E. (1990) in Proceedings of the 4th European Symposium on Life Sciences Research in Space, ESA Publications Div., ESTEC, Nordwijk, pp. 405-10.
- 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 80-85.
- Bennett, R.D. and Heftmann, E. (1966) Biosynthesis of pregnenolone from cholesterol in Haplopappus heterophyllus . Phytochemistry, 5 747-54.
- 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.
- Benveniste, P. (1986) Sterol Biosynthesis. Annu. Rev. Plant Physiol., 37 275-308.
- Bergenstrahle, A., Tollberg, E. and Jonsson, L. (1992a) Characterization of UDP-glucose solanidine glucosyltransferase and UDP-galactose solanidine galactosyltransferase from potato tuber. Plant Sci., 84 35-44.
- Bergenstrahle, A., Tollberg, E. and Jonsson, L. (1992b) Regulation of glycoalkaloid accumulation in potato tuber discs. J. Plant Physiol., 140 269-75.
- 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, 39 775-77.
- 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., 108 855-56.
- 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., 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.
- Böttigheimer, U. and Kreis, W. (1995) Partial purification and characterization of cardenolide glucohydrolase II from Digitalis lanata Ehrh, in 43th Annual Congress of Medicinal Plant Research, Halle.
- Bouvier, F., d'Harlingue, A., Suire, C., Backhaus, R.A. and Camara, B. (1998) Dedicated roles of plastid transketolases during the early onset of isoprenoid biogenesis in pepper fruits. Plant Physiol., 117 1423-31.
- Bouvier-Navé, P. and Benveniste, P. (1995) Sterol acyl transferase and steryl ester hydrolase activities in a tobacco mutant which overproduces sterols. Plant Sci., 110 11-19.
- Bowers, W.S. (1991) Insect hormones and antihormones in plants, in Herbivores: Their Interactions With Secondary Plant Metabolites (eds. G.A. Rosenthal and M.R. Berenbaum) 2nd edn. Academic Press. San Diego; pp. 431-56.
- Broers, S.T.J. (1994) Ueber die fruehen Stufen der Biosynthese von Isoprenoiden in Escherichia coli Ph.D. Thesis, Eidgenoessische Technische Hochschule, Zurich.
- Bühl, W. (1984) Enzyme in Blättern von Digitalis-Arten unter besonderer Berücksichtigung von herzglykosidspaltender Glucosidase und Esterase, Doctoral Thesis, University of Marburg.
- 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 41-48.
- Butler, A.R. and Wu, Y.-L. (1992) Artemisinin (qinghaosu): a new type of antimalarial drug. Chem. Soc. Rev. pp. 85-90.
- Cabello-Hurtado, F., Zimmerlin, A., Rahier, A., Taton, M., Derose, R., Nedelkina, S., Batard, Y., Durst, F., Pallett, K.E. and Werck-Reichhart, D. (1997) Cloning and functional expression in yeast of a cDNA coding for an obtusifoliol 14α-demethylase (CYP51) in wheat. Biochem. Biophys. Res. Commun., 230 381-85.
- 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-methylflutaryl coenzyme A reductase. Plant Mol. Biol., 13 627-38.
- Campbell, M., Hahn, F.M., Poulter, C.D. and Leustek, T. (1998) Analysis of the isopentenyl diphosphate isomerase gene family from Arabidopsis thaliana . Plant Mol. Biol., 36 323-28.
- 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. Chemcal Rev., 90 1089-103.
- D.E. Cane (ed.) (1998) Comprehensive Natural Products Chem: Isoprenoid Biosynthesis. Pergamon Press, Oxford.
- 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, 2nd Symposium of the European Network on Plant Terpenoids, Strasbourg, France.
- Caspi, E., Lewis, D.O., Piatak, D.M., Thimann, K.V. and Winter, A. (1966) Biosynthesis of plant sterols. Conversion of cholesterol to pregnenolone in Digitalis purpurea . Experientia, 12 506-507.
- Cerdon, C., Rahier, A., Taton, M. and Sauvaire, Y. (1995) Effects of tetcyclacis on growth and on sterol and sapogenin content in Fenugreek. J. Plant Growth Reg., 14 15-22.
- 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 48-52.
- Chappell, J., Wolf, F., Proulx, J., Cuellar, R. and Saunders, C. (1995) Is the reaction catalyzed 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 Press, Oxford, pp. 65-125.
- B.V. Charlwood and D.V. Banthorpe (eds.) (1991) Methods in Plant Biochemsitry, Vol. 7, Terpenoids, Academic Press, London.
- 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., 3 600-607.
- 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., 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.
- 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.
- Christmann, J., Kreis, W. and Reinhard, E. (1993) Uptake, transport and storage of cardenolides in foxglove: cardenolide sinks and occurrence of cardenolides in the sieve tubes of Digitalis lanata . Botanica Acta, 106 419-27.
- Chye, M.-L., Tan, C.-T. and Chua, N.-H. (1992) Three genes encode 3-hydroxy-3-methylglutaryl-coenzyme a reductase in Hevea brasiliensis: hmg1 and hmg3 are differentially expressed. Plant Mol. Biol., 19 473-84.
- 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. (1991) Dictionary of Terpenoids. Chapman and Hall, London.
- Connolly, J.D. and Hill, R.A. (1997) Triterpenoids. Natl. Prod. Rep., 14 661-80.
- Conolly, J.D., Hill, R.A. and Ngadjui, B.T. (1994) Triterpenoids. Natl. Prod. Rep., 11 467-92.
- 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. (1993) The separate roles of plant cis and trans prenyl transferases in cis-1,4-polyisoprene biosynthesis. Eur. J. Biochem., 218 267-71.
- Cornish, K. and Backhaus, R.A. (1990) Rubber transferase activity in rubber particles of guayule. Phytochemistry, 29 3809-13.
- Cornish, K. and Siler, D.J. (1996) Characterization of cis-prenyl transferase activity localized in a buoyant fraction of rubber particles from Ficus elastica latex. Plant Physiol. Biochem., 34 377-84.
- 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-farnesene. Proc. Natl. Acad. Sci. USA, 94 12833-38.
- 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.
- 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.
- Dean, P.D.G., Exley, D. and Goodwin, T.W. (1971) Steroid estrogens in plants: re-estimation of estrone in pomegranate seeds. Phytochemistry, 10 2215-16.
- 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 9710-15.
- 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 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 predator-prey interactions: involvement of host plant in its production. J. Chem. Ecol., 16 381-96.
- 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.
- Disch, A., Hemmerlin, A., Bach, T.J. and Rohmer, M. (1998a) Mevalonate-derived isopentenyl diphosphate is the biosynthetic precursor of ubiquinone prenyl side chain in tobacco by-2 cells. Biochem. J., 331 (Part 2) 615-21.
- Disch, A., Schwender, J., Muller, C., Lichtenthaler, H.K. and Rohmer, M. (1998b) Distribution of the mevalonate and glyceraldehyde phosphate/pyruvate pathways for isoprenoid biosynthesis in unicellular algae and the cyanobacterium Synechocystis PCC-6714. Biochem. J., 333 381-88.
- Dogbo, O. and Camara, B. (1987) Purification of isopentenyl pyrophosphate isomerase and geranylgeranyl pyrophosphate synthase from Capsicum chromoplasts by affinity chromatography. Biochim. Biophys. Acta, 920 140-48.
- 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.
- 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.
- Duport, C., Spagnoli, R., Degryse, E. and Pompon, D. (1998) Self-sufficient biosynthesis of pregnenolone and progesterone in engineered yeast. Nature Biotechnol., 16 186-89.
- 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 6181-84.
- Eisenreich, W., Menhard, B., Hylands, P.J., Zenk, M.H. and 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.
- 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.
- Faust, T. (1994) Synthese und Charakterisierung von Uridin-5′-diphospho-α-d-fucose sowie Nachweis, partielle Reinigung und Charakterisierung einer UDP-fucose:Digitoxigenin 3-O-β-d-Fucosyltransferase aus Digitalis lanata EHRH. Doctoral Thesis, University of Tübingen.
- Faust, T., Theurer, Ch., Eger, K. and Kreis, W. (1994) Synthesis of uridine 5′-(α-d-fucopyranosyl diphosphate) and (digitoxigenin-3β-yl)-β-d-fucopyranoside and enzymatic β-d-fucosylation of cardenolide genins in Digitalis lanata . Bioorg. Chem., 22 140-49.
- 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.
- Finsterbusch, A., Lindemann, P. and Luckner, M. (1997) Partial purification of Δ5-3β-hydroxysteroid dehydrogenase/Δ5-Δ4-ketosteroid isomerase of cell cultures of Digitalis lanata, in 45th Annual Congress on Medicinal Plant Research , Regensburg.
- 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. (1997) Natural sesquiterpenoids. Nat. Prod. Rep., 14 145-62.
-
Franz, G. and Meier, H. (1964) Uridine diphosphate digitoxose from the leaves of Digitalis purpurea (L.). Biochim. Biophys. Acta, 184
658-59.
10.1016/0304-4165(69)90286-4 Google Scholar
- Franz, G. and Hassid, W.Z. (1967) Biosynthese of digitoxose and glucose in the purpurea glycosides of Digitalis purpurea (L.). Phytochemistry, 6 841-44.
- Franz, G. and Meier, H. (1969) Untersuchungen zur Biosynthese der Digitalisglycoside. Planta Med., 4 396-400.
-
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 Press, 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 1183-86.
- Funk, C. and Croteau, R. (1994) Diterpenoid resin acid biosynthesis in conifers: characterization of two cytochrome P450-dependent monooxygenases and an aldehyde dehydrogenase involved in abietic acid biosynthesis. Arch. Biochem. and Biophys., 308 258-66.
- Funk, C., Lewinsohn, E., Vogel, B.S., Steele, C.L. and Croteau, R. (1994) Regulation of oleoresinosis in grand fir (Abies grandis): coordinate induction of monoterpene and diterpene cyclases and two cytochrome P450,-dependent diterpenoid hydroxylases by stem wounding. Plant Physiol., 106 999-1005.
- Gaisser, S. and Heide, L. (1996) Inhibition and regulation of shikonin biosynthesis in suspension cultures of Lithospermum . Phytochemistry, 41 1065-72.
- Galagovsky, L.R., Porto, A.M., Burton, G. and Gros, E.G. (1984) Biosynthesis of the bufadienolide ring of scillirosid in Scilla maritima . Z. Naturforsch., 39c 38-44.
- Gärtner, D.E. and Seitz, H.U. (1993) Enzyme activities in cardenolide-accumulating, mixotrophic shoot cultures of Digitalis purpurea (L.). J. Plant Physiol., 141 269-75.
- Gärtner, D.E., Wendroth, S. and Seitz, H.U. (1990) A stereospecific enzyme of the putative biosynthetic pathway of cardenolides: characterization of a progesterone 5β-reductase from leaves of Digitalis purpurea . FEBS Lett., 271 239-42.
- 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.
- Giner, J.L. and Djerassi, C. (1995) A reinvestigation of the biosynthesis of lanosterol in Euphorbia lathyris . Phytochemistry, 39 333-35.
- Gleizes, M., Pauly, G., Carde, J.P., Marpeau, A. and Bernard-Dagan, C. (1983) Monoterpene hydrocarbon biosynthesis by isolated leucoplasts of Citrofortunella mitis . Planta, 159 373-81.
- Goldstein, J.L. and Brown, M.S. (1990) Regulation of the mevalonate pathway. Nature, 343 425-30.
- 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.
- Gondet, L., Bronner, R. and Benveniste, P. (1994) Regulation of sterol content in membranes by subcellular compartmentation of steryl-esters accumulating in a sterol-overproducing tobacco mutant. Plant Physiol., 105 509-18.
- Goodwin, T.W. (1985) Biosynthesis of plant sterols, in Sterols and Bile Acids (eds. H. Danielsson and J. Sjövall), New Comprehensive Biochemistry, Elsevier Science Publishers B.V., 12 175-198.
- Gould, M.N. (1995) Prevention and therapy of mammary cancer by monoterpenes. J. Cell. Biochem., Suppl. 22 139-44.
- Grausem, B., Chaubet, N., Gigot, C., Loper, J.C. and Benveniste, P. (1995) Functional expression of Saccharomyces cerevisiae CYP51A1 encoding lanosterol-14-demethylase in tobacco results in bypass of endogenous sterol biosynthetic pathway and resistance to an obtusifoliol-14-demethylase herbicide inhibitor. Plant J., 7 761-70.
- Gray, J.C. (1987) Control of isoprenoid biosynthesis in higher plants. Adv. Bot. Res., 14 25-91.
- Grayson, D.H. (1997) Monoterpenoids. Nat. Prod. Rep., 14 477-522.
- Groeneveld, H.W., v. Tegelen, L.J.P. and Versluis, K. (1992) Cardenolide and neutral lipid biosynthesis from malonate in Digitalis lanata . Planta Med., 58 239-44.
- Groeneveld, H.W., Van den Berg, B., Elings, J.C. and Seykens, D. (1990) Cardenolide biosynthesis from malonate in Asclepias curassavica . Phytochemistry, 29 3479-86.
-
Grunwald, C. (1980) Steroids, in Encyclopedia of Plant Physiology, New Series, Vol. 8, Secondary plant products (eds. E.A. Bell and B.V. ) Springer-Verlag, Berlin, Heidelberg, New York, pp. 221-56.
10.1007/978-3-642-67360-3_10 Google Scholar
- 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., 308 103-108.
- Hagimoro, M., Matsumoto, T. and Obi, Y. (1982) Studies on the production of Digitalis cardenolides by plant tissue culture. II. Effect of light and plant growth substances on digitoxin formation by undifferentiated cells and shoot-forming cultures of Digitalis purpurea (L.) grown in liquid media. Plant Physiol., 69 653-56.
- 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., 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.
- 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, 48 421-27.
- Hamada, H., Konishi, H., Williams, H.J. and Scott, A.I. (1991) Biotransformation of testosterone isomers by a green cell suspension cultures of Marchantia polymorpha . Phytochemistry, 30 2269-70.
- Hanley, K.M., Voegeli, U. and Chappell, J. (1992) A study of the isoprenoid pathway in elicitor-treated tobacco cell suspension cultures, in Secondary-Metabolite Biosynthesis and Metabolism (eds. R.J. Petroski and S.P. McCormick) Plenum Press, New York, pp. 329-36.
- Hanson, J.R. (1997) Diterpenoids. Nat. Prod. Rep., 14 245-58.
- J.B. Harborne and F.A. Tomas-Barberan (eds.) (1991) Ecological Chemistry and Biochemistry of Plant Terpenoids. Clarendon Press, Oxford, pp. 439.
- Hedden, P. and Kamiya, Y. (1997) Gibberellin biosynthesis: enzymes, genes and their regulation. Annu. Rev. Plant Physiol. Plant Mol. Biol., 48 431-60.
- Heide, L. and Berger, U. (1989) Partial purification and properties of geranyl pyrophosphate synthase from Lithospermum erythrorhizon cell cultures. Arch. Biochem. Biophys., 273 331-38.
- 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 1121-27.
- 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., 32 791-97.
- 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.
- Henry, M., Rahier, A. and Taton, M. (1992) Effect of gypsogenin 3-O-glucuronide pretratment of Gypsophila paniculata and Saponaria officinalis cell suspension cultures on the activities of microsomal 2,3-oxidosqualene cycloartenol and amyrin cyclases. Phytochemistry, 31 3855-59.
- Hezari, M. and Croteau, R. (1997) Taxol biosynthesis: an update. Planta Med., 63 291-95.
- Hezari, M., Ketchum, R.E.B., Gibson, D.M. and Croteau, R. (1997) Taxol production and taxadiene synthase activity in Taxus canadensis cell suspension cultures. Arch. Biochem. Biophys., 337 185-90.
- Horbach, S., Sahm, H. and Welle, R. (1993) Isoprenoid biosynthesis in bacteria: two different pathways? FEMS Microbiol. 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.
- Husselstein, T., Gachotte, D., Desprez, T., Bard, M. and Benvensite, P. (1996) Transformation of Saccharomyces cerevisiae with a cDNA encoding a sterol C-methyltransferase from Arabidopsis thaliana results in the synthesis of 24-ethyl sterols. FEBS Lett., 381 87-92.
- Inoue, K. and Ebizuka, Y. (1996) Purification and characterization of furostanol glycoside 26-O-β-glucosidase from Costus speciosus rhizomes. FEBS Lett., 378 157-60.
- Inoue, K., Shibuya, M., Yamamoto, K. and Ebizuka, Y. (1996) Molecular cloning and bacterial expression of a cDNA encoding furostanol glycoside 26-O-beta-glucosidase of Costus speciosus . FEBS Lett., 389 273-77.
- Jansen, B.J.M. and de Groot, A. (1991) The occurrence and biological activity of drimane sesquiterpenoids. Natl. Prod. Rep., 8 309-18.
- 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.
- 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 26983-89.
- 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., 8 880-85.
- Kandzia, R., Grimm, R., Eckerskorn, C., Lindemann, P. and Luckner, M. (1998) Purification and characterization of lanatoside 15′-O-acetylesterase from Digitalis lanata Ehrh. Planta, 204 383-89.
- 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.
- Kawaguchi, K., Hirotani, M., Yoshikawa, T. and Furuya, T. (1990) Biotransformation of digitoxigenin by ginseng hairy root cultures. Phytochemistry, 29 837-44.
- 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., 251 413-17.
- Kerr, R.G., Kelly, K. and Schulman, A. (1995) A novel biosynthetic route to pregnanes in the marine sponge Amphimedon compressa . J. Nat. Prod. — Lloydia, 58 1077-80.
- 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., 60 685-86.
- 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.
- Kreis, W. and May, U. (1990) Cardenolide glucosyltransferases and glucohydrolases in leaves and cell cultures of three Digitalis (Scrophulariaceae) species. J. Plant Physiol., 136 247-52.
- Kreis, W. and Reinhard, E. (1990a) Production of deacetyllanatoside C by Digitalis lanata cell cultures, in Progress in plant cellular and molecular biology (eds H.J.J. Nijkamp, L.H.W. Plaas and J. Aartrijk), Kluwer Academic Publishers, Dordrech, Boston, London, pp. 706-11.
- Kreis, W. and Reinhard, E. (1990b) 12$-Hydroxylation of digitoxin by suspension-cultured Digitalis lanata cells: production of digoxin in 20 litre and 300 litre airlift bioreactors. J Biotechnol., 16 123-36.
- Kreis, W., May, U. and Reinhard, E. (1986) UDP:glucose:digitoxin 16′-O-glucosyltransferase from suspension-cultured Digitalis lanata cells. Plant Cell Rep., 5 442-45.
- Kreis, W., Hoelz, H., Sutor, R. and Reinhard, E. (1993) Cellular organization of cardenolide biotransformation in Digitalis grandiflora . Planta, 191 246-51.
- Kreis, W., Mangelsdorf, C., Stuhlemmer, U. and Haussmann, W. (1997) Acetoxypregnanes and acetylated cardenolides as precursors of cardiac glycosides in Digitalis lanata shoot cultures and the occurrence of esterases hydrolysing acetoxycardenolides, in 45th Annual Congress on Medicinal Plant Research , Regensburg.
- Kreis, W., Hensel, A. and Stuhlemmer, U. (1998) Cardenolide biosynthesis in foxglove. Planta Med., (in press).
- Kuntz, M., Roemer, S., Suire, 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.
- Kurz, W.G.W. and Constabel, F. (1979) Plant cell cultures, a potential source of pharmaceuticals. Adv. Appl. Microbiol., 25 209-40.
- Kushiro, T., Ohno, Y., Shibuya, M. and Ebizuka, Y. (1997) In vitro conversion of 2,3-oxidosqualene into dammarenediol by Panax ginseng microsomes. Biol. Pharmaceut. Bull., 20 292-94.
- Kuzma, J. and Fall, R. (1993) Leaf isoprene emission rate is dependent on leaf development and the level of isoprene synthase. Plant Physiol., 101 435-40.
- Kuzuyama, T., Takahashi, S., Watanabe, H. and Seto, H. (1998) Direct formation of 2-C-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.
- Laferriere, A. and Beyer, P. (1991) Purification of geranylgeranyl diphosphate synthase from Sinapis alba etioplasts. Biochim. Biophys . Acta, 1077 167-72.
- LaFever, R.E., Vogel, B.S. and Croteau, R. (1994) Diterpenoid resin acid biosynthesis in conifers: enzymatic cyclization of geranylgeranyl pyrophosphate to abietadiene, the precursor of abietic acid. Arch. Biochem. Biophys., 313 139-49.
- Laflamme, P., Khouri, H., Gulick, P. and Ibrahim, R. (1993) Enzymatic prenylation of isoflavones in white lupin. Phytochemistry, 34 147-51.
- Lamb, D.C., Kelly, D.E. and Kelly, S.L. (1998) Molecular diversity of sterol 14α-demethylase substrates in plants, fungi and humans. FEBS Lett., 425 263-65.
- 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 2100-104.
- 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 8552-56.
- Langenheim, J.H. (1994) Higher plant terpenoids: a phytocentric overview of their ecological roles. J. Chem. Ecol., 20 1223-80.
- 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.
- 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 1820-24.
- Li, C.P. and Larkins, B.A. (1996) Identification of a maize endosperm-specific cDNA encoding farnesyl pyrophosphate synthetase. Gene, 171 193-96.
- Lichtenthaler, H.K., Rohmer, M. and Schwender, J. (1997a) Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants. Physiologia Plantarum, 101 643-52.
- Lichtenthaler, H.K., Schwender, J., Disch, A. and Rohmer, M. (1997b) Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway. FEBS Lett., 400 271-74.
- 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.
- Lindemann, P. and Luckner, M. (1997) Biosynthesis of pregnane derivatives in somatic embryos of Digitalis lanata . Phytochemistry, 46 507-13.
- 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., 21 101-107.
-
Luckner, M. (1990) Secondary Metabolism in Microorganisms, Plants, and Animals. 3rd Edition, Gustav Fischer Verlag, Jena.
10.1007/978-3-662-09838-7 Google Scholar
-
Luckner, M. and Diettrich, B. (1985) Formation of cardenolides in cell and organ cultures of Digitalis lanata
, in Primary and Secondary Metabolism of Plant Cell Cultures (eds. K.H. Neumann, W. Barz and E. Reinhard), Springer-Verlag, Berlin, Heidelberg, New York, pp. 154-63.
10.1007/978-3-642-70717-9_15 Google Scholar
- 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, 171 401-406.
- 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.
- Luta, M., Hensel, A. and Kreis, W. (1997) β-d-Fucosidase and other cardenolideglycoside-modifying enzymes in Digitalis lanata EHRH, in 45th Annual Congress on Medicinal Plant Research , Regensburg.
- Luta, M., Hensel, A. and Kreis, W. (1998) Synthesis of cardenolide glycosides and putative biosynthesis precursors of cardenolide glycosides. Steroids, 63 44-49.
- 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.
- Mahato, S.B., Nandy, A.K. and Roy, G. (1992) Triterpenoids, Phytochemistry, 31 2199-49
- Maier, M.S., Seldes, A.M. and Gros, E.G. (1986) Biosynthesis of the butenolide ring of cardenolides in Digitalis purpurea . Phytochemistry, 25 1327-29.
- 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 1613-14.
- Marrero, P.F., Poulter, C.D. and Edwards, P.A. (1992) Effects of site-directed mutagenesis of the highly conserved aspartate residues in domain II of farnesyl diphosphate synthase activity. J. Biol. Chem., 267 21873-78.
- Matsushita, Y., Kang, W. and Charlwood, B.V. (1996) Cloning and analysis of a cDNA encoding farnesyl diphosphate synthase from Artemisia annua . Gene, 172 207-209.
- 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. (1995) Monoterpene and sesquiterpene biosynthesis in glandular trichomes of peppermint (Mentha × piperita) rely exclusively on plastid-derived isopentenyl diphosphate. Planta, 197 49-56.
- McGarvey, D.J. and Croteau, R. (1995) Terpenoid metabolism. Plant Cell, 7 1015-26.
-
Meiss, P., Sepasgosarian, J. and Reinhard, E. (1986) Production of β-methyldiginatin by Digitalis cell cultures. Planta Med., 52
511-13.
10.1055/s-2007-969285 Google Scholar
- Mettal, U., Boland, W., Beyer, P. and Kleinig, H. (1988) Biosynthesis of monoterpene hydrocarbons by isolated chromoplasts from daffodil flowers. Eur. J. Biochem., 170 613-16.
- 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.
- Milek, F., Reinhard, E. and Kreis, W. (1997) Influence of precursors and inhibitors of the sterol pathway on sterol and cardenolide metabolism in Digitalis lanata Ehrh. Plant Physiol Biochem., 35 111-21.
- 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 Press, New York, pp. 83-97.
- Monson, R., Jaeger, C.H., Adams, W.W.I., Driggers, E.M., Silver, G.M. and Fall, R. (1992) Relationships among isoprene emission rate, photosynthesis and isoprene synthase activity as influenced by temperature. Plant Physiol., 98 1175-80.
- Montamat, 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.
- Morehead, T.A., Biermann, B.J., Crowell, D.N. and Randall, S.K. (1995) Changes in protein isoprenylation during the growth of suspension-cultured tobacco cells. Plant Physiol., 109 277-84.
- Muhlenweg, A., Melzer, M., Li, S.M. and Heide, L. (1998) 4-Hydroxybenzoate 3-geranyltransferase from Lithospermum erythrorhizon: purification of a plant membrane-bound 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 Chemical Communications, 6
681-82.
10.1039/c39950000681 Google Scholar
- 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., 34 421-29.
- 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, S.D., McClanahan, R.H., Knebel, N., Thomassen, D., Gordon, W.P. and Oishi, S. (1992) The metabolism of (R)-(+)-pulegone, a toxic monoterpene, in Secondary-Metabolite Biosynthesis and Metabolism (eds. R.J. Petroski and S.P. McCormick), Plenum Press, New York, pp. 287-96.
10.1007/978-1-4615-3012-1_19 Google Scholar
- 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.
- Obatomi, D.K. and Bach, P.H. (1998) Biochemistry and toxicology of the diterpenoid glycoside atractyloside. Food Chem. Toxicol., 36 335-46.
- Ohnuma, S., Hirooka, K., Hemmi, H., Ishida, C., Ohto, C. and Nishino, T. (1996a) Conversion of product specificity of archaebacterial geranylgeranyl-diphosphate synthase: identification of essential amino acid residues for chain length determination of prenyltransferase reaction. J. Biol. Chem., 271 18831-37.
- Ohnuma, S., Narita, K., Nakazawa, T., Ishida, C., Takeuchi, Y., Ohto, C. and Nishino, T. (1996b) A role of the amino acid residue located on the fifth position before the first aspartate-rich motif of farnesyl diphosphate synthase on determination of the final product. J. Biol. Chem., 271 30748-54.
- Ohnuma, S.I., Nakazawa, T., Hemmi, H., Hallberg, A.M., Koyama, T., Ogura, K. and Nishino, T. (1996c) Conversion from farnesyl diphosphate synthase to geranylgeranyl diphosphate synthase by random chemical mutagenesis. J. Biol. Chem., 271 10087-95.
- Ohnuma, S., Hirooka, K., Ohto, C. and Nishino, T. (1997) Conversion from archaeal geranylgeranyl diphosphate synthase to farnesyl diphosphate synthase: two amino acids before the first aspartate-rich motif solely determine eukaryotic farnesyl diphosphate synthase activity. J. Biol. Chem., 272 5192-98.
- 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-3-3methylglutaryl coenzyme A reductase activity without effect on its mRNA level. J. Plant Physiol., 141 463-69.
- Paczkowski, C. and Woiciechowski, Z.A. (1994) Glucosylation and galactosylation of diosgenin and solasodine by soluble glycosyltransferase(s) from Solanum melongena leaves. Phytochemistry, 35 1429-34.
- Paczkowski, C., Kalinowska, M. and Woiciechowski, Z.A. (1997) UDP-glucose:solasodine glucosyltransferase from eggplant (Solanum melongena L.) leaves: partial purification and characterization. Acta Biochim . Polonica, 44 43-54.
- 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.
- Paper, D.H. and Franz, G. (1990) Biotransformation of 5βH-pregnan-3βol-20-one and cardenolides in cell suspension cultures of Nerium oleander (L.). Plant Cell Rep., 8 651-55.
- Pare, P.W. and Tumlinson, J.H. (1997) Induced synthesis of plant volatiles. Nature, 385 30-31.
- Park, H., Denbow, C.J. 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.
- Pascal, S., Taton, M. and Rahier, A. (1990) Oxidative C4-demethylation of 24-methylenecy-cloartanol by a cyanide-sensitive enzymatic system from higher plant microsomes. Biochem. Biophys. Res. Commun., 172 98-106.
- Pascal, S., Taton, M. and Rahier, A. (1993) Plant sterol biosynthesis: identification and characterization of two distinct microsomal oxidative enzymatic systems involved in sterol C4-demethylation. J. Biol. Chem., 268 11639.
- Pascal, S., Taton, M. and Rahier, A. (1994) Plant sterol biosynthesis: identification of a NADPH-dependent sterone reductase involved in sterol 4-demethylation. Arch. Biochem. Biophys., 312 260-71.
- Petersen, M. and Seitz, H.U. (1985) Cytochrome P450-dependent digitoxin 12β-hydroxylase from cell cultures of Digitalis lanata . FEBS Lett., 188 11-14.
- Petersen, M., Seitz, H.U., Alfermann, A.W. and Reinhard, E. (1987) Immobilization of digitoxin 12β-hydroxylase, a cytochrome P450-dependent enzyme, from cell cultures of Digitalis lanata EHRH. Plant Cell Rep., 6 200-203.
-
Petersen, M., Seitz, H.U. and Reinhard, E. (1988) Characterization and localization of digitoxin 12β hydroxylase form cell cultures of Digitalis lanata EHRH. Z. Naturforsch., 43c
199-206.
10.1515/znc-1988-3-409 Google Scholar
- 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.
- Pichersky, E., Raguso, R.A., Lewinsohn, E. and Croteau, R. (1994) Floral scent production in Clarkia (Onagraceae). I. Localization and developmental modulation of monoterpene emission and linalool synthase activity. Plant Physiol., 106 1533-40.
- Pichersky, E., Lewinsohn, E. and Croteau, R. (1995) Purification and characterization of S-linalool synthase, an enzyme involved in the production of floral scent in Clarkia breweri . Arch. Biochem. Biophys., 316 803-807.
- 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. Chemie , (in press).
- 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), John Wiley and Sons, New York, pp. 161-224.
- Pras, N. (1990) Bioconversion of precursors occurring in plants and related synthetic compounds, in Progress in Plant Cellular and Molecular Biology (eds. H.J.J. Nijkamp, L.H.W. Plaas and J. Aartrijk), Kluwer Academic Publishers, Dordrech, Boston, London, pp. 640-49.
- 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.
- Rahier, A. and Taton, M. (1986) The 14α-demethylation of obtusifoliol by a cytochrome P450 monooxygenase from higher plants microsomes. Biochem. Biophys. Res. Commun., 140 1064-72.
- Rahier, A. and Taton, M. (1992) Plant sterol biosynthesis. 7. Oxoobtusifoliol analogues as potential selective inhibitors of cytochrome P450-dependent obtusifoliol 14α-demethylase. Biochim. Biophys. Acta, 1125 215-22.
- Rahier, A. and Taton, M. (1997) Fungicides as tools in studying postsqualene sterol synthesis in plants. Pest. Biochem. Physiol., 57 1-27.
- Rahier, A., Smith, M. and Taton, M. (1997) The role of cytochrome b5 in 4α-methyl-oxidation and C5(6) desaturation of plant sterol precursors. Biochem. Biophys. Res. Commun., 236 434-37.
- 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 × 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., 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.
- Ramosvaldivia, A.C., Vanderheijden, R. and Verpoorte, R. (1998) Isopentenyl diphosphate isomerase and prenyltransferase activities in rubiaceous and apocynaceous cultures. Phytochemistry, 48 961-69.
- Re, E.B., Jones, D. and Learned, R.M. (1995) Co-expression of native and introduced genes reveals cryptic regulation of HMG-CoA reductase expression in Arabidopsis . Plant J., 7 771-84.
-
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
- Reinhard, E. and Alfermann, A.W. (1980) Biotransformation by plant cell cultures. Adv. Biochem. Eng., 16 49-83.
-
Reinhard, E., Boy, M. and Kaiser, F. (1975) Umwandlung von Digitalis-Glykosiden durch Zellsuspensionskulturen. Planta Med., (Suppl.) 1975
163-68.
10.1055/s-0028-1105792 Google Scholar
- Reinhard, E., Kreis, W., Barthlen, U. and Helmbold, U. (1989) Semicontinuous cultivation of Digitalis lanata cells: production of β-methyldigoxin in a 300 L airlift bioreactor. Biotechnol. Bioeng., 34 502-508.
- 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 Chloroflexusaurantiacus: 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, 148 293-97.
- Rogers, L.J., Shah, S.P.J. and Goodwin, T.W. (1968) Compartmentation of biosynthesis of terpenoids in green plants. Photosynthetica, 2 184-207.
- Rohmer, M., Knani, M., Simonin, P., Sutter, B. and Sahm, H. (1993) Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem. J., 295 517-24.
- 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 2564-66.
- 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.
- Saden-Krehula, M., Tajic, M. and Kolbah, D. (1976) Investigation on some steroid hormones and their conjugates in pollen of Pinus nigra: separation of steroids by thin layer chromatography. Biologisches Zentralblatt, 95 223-26.
- 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 2091-94.
- 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., 2 221-22.
- Salmon, F., Taton, M., Benveniste, P. and Rahier, A. (1992) Plant sterol biosynthesis novel potent and selective inhibitors of cytochrome P450-dependent obtusifoliol 14α-methyldemethylase. Arch. Biochem. Biophys., 297 123-31.
- Sandmann, G. and Albrecht, M. (1994) Assays for three enzymes involved in mevalonic acid metabolism. Physiologia Plantarum, 92 297-301.
- Sanmiya, K., Iwasaki, T., Matsuoka, M., Miyao, M. and Yamamoto, N. (1997) Cloning of a cDNA that encodes farnesyl diphosphate synthase and the blue-light-induced expression of the corresponding gene in the leaves of rice plants. Biochim. Biophys . Acta: Gene Structure Expression, 1350 240-46.
- 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-methylglutaryl-coenzyme A reductase 1 in tobacco results in sterol overproduction. Plant Physiol., 109 761-70.
-
Schütte, H.R. (1987) Secondary plant substances: aspects of steroid biosynthesis. Prog. Bot., 49
117-36.
10.1007/978-3-642-73023-8_8 Google Scholar
- 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 1872-74.
- Schwarz, M.K. (1994) Terpen-Biosynthese in Ginkgo biloba: Eine ueberraschende Geschichte PhD Thesis, Eidgenoessische Technische Hochschule, Zurich.
- Schwender, J., Seemann, M., Lichtenthaler, H.K. and Rohmer, M. (1996) Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliquus . Biochem. J., 316 (Part 1) 73-80.
- 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.
- Seidel, S. and Reinhard, E. (1987) Major cardenolide glycosides in embryogenic suspension cultures of Digitalis lanata . Planta Med., 3 308-309.
- Seidel, S., Kreis, W. and Reinhard, E. (1990) Δ5-3β-Hydroxysteroid dehydrogenase/Δ5-Δ4-ketosteroid isomerase (3β-HSD), a possible enzyme of cardiac glycoside biosynthesis, in cell cultures and plants of Digitalis lanata EHRH. Plant Cell Rep., 8 621-24.
- 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 13010-16.
- Singsaas, E.L., Lerdau, M., Winter, K. and Sharkey, T.D. (1997) Isoprene increases thermotolerance of isoprene-emitting species. Plant Physiol., 115 1413-20.
- 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, 191 324-29.
- 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 3044-48.
- 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 12857-862.
- 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.
- Stapleton, A., Allen, P.V., Friedman, M. and Belknap, W.R. (1991) Purification and characterization of solanidine glucosyltransferase from the potato Solanum tuberosum. A. Agric. Food Chem., 39 1187-93.
- 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.
- Stuhlemmer, U. and Kreis, W. (1996a) Cardenolide formation and activity of pregnane-modifying enzymes in cell suspension cultures, shoot cultures and leaves of Digitalis lanata. Plant Physiol . Biochem., 34 85-91.
- Stuhlemmer, U. and Kreis, W. (1996b) Does malonyl coenzyme A:hydroxypregnane 21-hydroxymalonyltransferase catalyze the first step in butenolide ring formation? Tetrahedron Lett., 37 2221-24.
-
Stuhlemmer, U., Haussmann, W., Milek, F., Kreis, W. and Reinhard, E. (1993a) 3α-Hydroxysteroid-5β-oxidoreductase in tissue cultures of Digitalis lanata
. Z. Naturforsch., 48c
713-21.
10.1515/znc-1993-9-1006 Google Scholar
- Stuhlemmer, U., Kreis, W., Eisenbeiss, M. and Reinhard, E. (1993b) Cardiac glycosides in partly submerged shoots of Digitalis lanata . Planta Med., 59 539-45.
- Suga, T. and Hirata, T. (1990) Biotransformation of exogenous substrates by plant cell cultures. Phytochemistry, 29 2393-406.
- 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.
- Sutor, R. and Kreis, W. (1996) Partial purification and characterization of the cell-wall-associated lanatoside 15′-O-acetylesterase from Digitalis lanata suspension cultures. Plant Physiol. Biochem., 34 763-70.
- Sutor, R., Hoelz, H. and Kreis, W. (1990) Lanatoside 15′-O-acetylesterase from Digitalis (Scrophulariaceae) plants and cell cultures. J. Plant Physiol., 136 289-94.
- Sutor, R., Kreis, W., Hoelz, H. and Reinhard, E. (1993) Acetyl coenzyme A:digitoxin 15′-O-acetyltransferase from Digitalis plants and suspension cultures. Phytochemistry, 32 569-73.
- Takahashi, S., Kuzuyama, T., Watanabe, H. and Seto, H. (1998) A 1-deoxy-d-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-d-erythritol 4-phosphate in an alternative non-mevalonate pathway for terpenoid biosynthesis. Proc. Natl. Acad. Sci. USA, 95 9879-84.
- 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 10871-77.
- 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.
- Taton, M., Benveniste, P. and Rahier, A. (1989) Microsomal Δ8,14 sterol Δ14-reductase in higher plants characterization and inhibition by analogues of a presumptive carbocationic intermediate of the reduction reaction. Eur. J. Biochem., 185 605-14.
- Taton, M. and Rahier, A. (1991) Identification of Δ5,7 sterol-Δ7-reductase in higher plant microsomes. Biochem. Biophys. Res. Commun., 181 465-73.
- Taton, M., Salmon, F., Pascal, S. and Rahier, A. (1994) Plant sterol biosynthesis: recent advances in the understanding of oxidative demethylations at C4 and C14. Plant Physiol. Biochem., 32 751-60.
- Taton, M. and Rahier, A. (1996) Plant sterol biosynthesis: identification and characterization of higher plant Δ7-sterol C5(6)-desaturase. Arch. Biochem. Biophys., 325 279-88.
- Theurer, C., Kreis, W. and Reinhard, E. (1998) Effects of digitoxigenin, digoxigenin and various cardiac glycosides on cardenolide accumulation in shoot culters of Digitalis lanata Ehrh. Planta Med., 64 705-10.
- Tschesche, R. and Kleff, U. (1973) Beiträge zur biochemischen 14β-Hydroxylierung von C21-Steroiden zu Cardenoliden. Phytochemistry, 12 2375-80.
- 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 1251-53.
- 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.
- Ullman, P., Rimmele, D., Benveniste, P. and Bouvier-Navé, P. (1984) Phospholipid-dependence of plant UDP-glucose-sterol-β-d-glucosyltransferase. 2. Acetone-mediated delipidation and kinetic studies. Plant Sci. Lett., 36 29-36.
- Ullman, P., Bouvier-Navé, P. and Benveniste, P. (1987) Regulation by phospholipids and kinetic studies of plant membrane-bound UDP-glucose sterol β-d-glucosyltransferase. Plant Physiol., 85 51-55.
- Ury, A., Benveniste, P. and Bouvier-Navé, P. (1989) Phospholipid-dependence of plant UDP-glucose-sterol-β-d-glucosyltransferase. IV. Reconstitution into small unilamellar vesicles. Plant Physiol., 91 567-73.
-
van Beek, T.A. and de Groot, A. (1986) Terpenoid antifeedants. Part I. An overview of terpenoid antifeedants of natural origin. Recueil des Travaux Chimiques des Pays-Bas, 105
513-27.
10.1002/recl.19861051202 Google Scholar
- Vardosanidze, M.G., Gurielidze, K.G., Pruidze, G.N. and Paseshnichenko, V.A. (1991) The substrate specificity of Allium erubescens β-glucosidase. Biokhymia, 56 2025-31.
- Veleiro, A.S., Burton, G. and Gros, E.G. (1985) Biosynthesis of withanolides in Acnistus breviflorus . Phytochemistry, 24 2263-66.
- Verlet, N. (1993) Commercial aspects, in Volatile Oil Crops: Their Biology Biochemistry and Production. (eds. R.K.M. Hay and P.G. Waterman), Longman Scientific and Technical, Essex, UK, pp. 137-74.
- Villarreal, M.L., Arias, C., Feria-Velasco, A., Ramirez, O.T. and Quintero, R. (1997) Cell suspension culture of Solanum chrysotrichum (Schldl.): a plant producing an antifungal spirostanol saponin. Plant Cell Tiss. Org. Cult., 50 39-44.
- 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 23262-68.
- 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.
-
Warneck, H.M. and Seitz, H.U. (1990) 3β-Hydroxysteroid oxidoreductase in suspension cultures of Digitalis lanata Ehrh. Z. Naturforsch., 45c
963-72.
10.1515/znc-1990-9-1007 Google Scholar
- Warnecke, D.C. and Heinz, E. (1994) Purification of a membrane-bound UDP-glucose: sterol β-d-glucosyltransferase based on its solubility in diethyl ether. Plant Physiol., 105 1067-73.
- Warnecke, D.C., Baltrusch, M., Buck, F., Wolter, F.P. and Heinz, E. (1997) UDP-glucose:sterol glucosyltransferase: cloning and functional expression in Escherichia coli . Plant Mol. Biol., 35 597-603.
- 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 1811-15.
- West, C.A. (1981) Biosynthesis of diterpenes, in Biosynthesis of Isoprenoid Compounds, (eds. J.W. Porter and S.L. Spurgeon), John Wiley and Sons, 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, 370 806-807.
- 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 9201-204.
- 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 Press, Oxford, UK.
- 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 14891-99.
- Woerdenbag, H.J., Pras, N., Frijlink, H.W., Lerk, C.F. and Malingré, T.M. (1990) Cyclodextrin-facilitated bioconversion of 17β-estradiol by a phenoloxidase from Mucuna pruriens cell cultures. Phytochemistry, 29 1551-54.
- Xu, Y.L., Li, L., Wu, K.Q., Peeters, A.J.M., Gage, D.A. and Zeevaart, J.A.D. (1995) The ga5 locus of Arabidopsis thaliana encodes a multifunctional gibberellin 20-oxidase: molecular cloning and functional expression. Proc. Natl. Acad. Sci. USA, 92 6640-44.
- 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 1271-78.
- Yamamoto, H., Kimata, J., Senda, M. and Inoue, K. (1997) Dimethylallyl diphosphate: kaempferol 8-dimethylallyl transferase in Epimedium diphyllum cell suspension cultures. Phytochemistry, 44 23-28.
- 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.
- Yoshikawa, T. and Furuya, T. (1979) Purification and properties of sterol UDP-glucose glucosyl transferase in cell culture of Digitalis purpurea . Phytochemistry, 18 239-42.
- 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., 332 280-87.
-
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., 52c
15-23.
10.1515/znc-1997-1-204 Google Scholar
- Zhang, F.L. and Casey, P.J. (1996) Protein prenylation: molecular mechanisms and functional consequences. Annu. Rev. Biochem., 65 241-69.
- Zimowski, J. (1991) Occurrence of a glucosyltransferase specific for solanidine in potato plants. Phytochemistry, 30 1827-32.
- Zimowski, J. (1992) Specificity and some other properties of cytosolic and membranous UDP-glucose 3β-hydroxysteroid glucosyltransferases from Solanum tuberosum leaves. Phytochemistry, 31 2977-81.
- 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 3441-45.
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