Abstract
The terpenoids (often referred to as isoprenoids) constitute the largest group of natural products, with more than 22, 000 individual structures now known (1). They are all derived from the sequential addition of branched, five-carbon isopentenoid (isoprenoid) units, and range in size from isoprene (C5H8) to natural rubber (molecular weight greater than 106). In plants, the terpenoids and meroterpenoids (in which the terpenoid comprises a part of a larger molecule) play a broad range of metabolic and physiological roles, for example in photosynthesis (chlorophyll side chains, carotenoids, phylloquinones, plastoquinones), respiration (ubiquinone), cell membrane architecture (sterols), regulation of growth and development (gibberellins, abscisic acid, brassinosteroids), defense mechanisms (as phytoalexins, insect feeding and oviposition deterrents, competitive phytotoxins), and reproduction (as attractants of pollinators and seed dispersing animals). Additionally, isoprenylation of proteins by addition of a C15 or C20 olefinic chain provides a means of membrane anchoring, for example of cell cycle-regulating proteins. In this chapter, we focus on one family of industrially and agronomically significant plant terpenoids, the monoterpenes, and on the potential for the molecular genetic manipulation of the biosynthesis of this group of C10 compounds formed by the head-to-tail condensation of two isoprenoid units.
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References
Connolly, J.D. and Hill, R.A. (1992) Dictionary of Terpenoids, Chapman and Hall, New York, NY.
Croteau, R. and Karp, F. (1991) in Perfumes: Art, Science and Technology (Müller, P.M. and Lamparsky, D., eds.), pp. 101–126, Elsevier, Amsterdam.
Belaiche, T., TantaouiElaraki, A. and Ibrahimy, A. (1995) Sci. Aliments 15, 571–578.
Beckstrom-Sternberg, S.M. and Duke, J.A. (1996) CRC Hand book of Medicinal Mints, CRC Press, Boca Raton, FL.
Crowell, P.L. and Gould, M.N. (1994) CRC Crit. Rev. Oncogenesis 5, 1–22.
Mills, J.J., Chari, R.S., Boyer, I.J., Gould, M.N. and Jirtle, R.L. (1995) Cancer Res. 55, 979–983.
Yu, S.G., Hildebrandt, L.A. and Elson, C.E. (1995) J. Nutr. 125, 2763–2767.
Gershenzon, J. and Croteau, R. (1991) in Herbivores: Their Interaction with Secondary Metabolites (Rosenthal, G.A. and Berenbaum, M., eds.), pp. 165–219, Academic Press, New York, NY.
Harborne, J.B. (1991) in Ecological Chemistry and Biochemistry of Plant Terpenoids (Harborne, J.B. and Tomas-Barberan, F.A., eds.), Vol. 31, pp. 399–426, Clarendon Press, Oxford, UK.
Pickett, J.A. (1991) in Ecological Chemistry and Biochemistry of Plant Terpenoids (Harborne, J.B. and Tomas-Barberan, F.A., eds.), Vol. 31, pp. 297–313, Clarendon Press, Oxford, UK.
Dobson, H.E.M. (1993) in Insect-Plant Interactions (Bernays, E., ed.), Vol. V, pp. 47–81, CRC Press, Boca Raton, FL.
Dobson, H.E.M., Bergstrom, G. and Groth, I. (1990) Isr. J. Bot. 39, 143.
Asplund, R.O. (1968) Phytochemistry 7, 3861–3869.
Vaughn, S.F. and Spencer, G.F. (1991) Amer. Potato J. 68, 821–831.
Hefendehl, F.W. and Murray, M.J. (1976) Lloydia 39, 39–52.
Fahn, A. (1979) Secretory Tissues in Plants, Academic Press, London, UK.
Carde, J. (1984) Eur. J. Cell Biol. 34, 18–26.
Kleinig, H. (1989) Anna Rev. Plant. Physiol. Plant. Mol. Biol. 40, 39–59.
Gershenzon, J. and Croteau, R. (1991) in Biochemistry of the Mevalonic Acid Pathway to Terpenoids (Towers, G.H.N. and Stafford, H.A., eds.), pp. 99–160, Plenum Press, New York, NY.
Rohmer, M, Knani, M, Simonin, P., Sutter, B. and Sahm, H. (1993) Biochem. J. 295, 517–524.
Schwender, J., Seemann, M., Lichtenthaler, H.K. and Rohmer, M. (1996) Biochem. J. 316, 73–80.
Rohmer, M., Seeman, M., Horbach, S., Bringer-Meyer, S. and Sahm, H. (1996) J. Amer. Chem. Soc. 118, 2564–2566.
Schwarz, M.K. (1994), Diss. ETH Nr. 10951, Zürich.
McCaskill, D. and Croteau, R. (1995) Planta 197, 49–56.
Lichtenthaler, H.K., Schwender, J., Disch, A. and Rohmer, M. (1997) FEBS Lett. 400, 271–274.
Eisenreich, W., Menhard, B., Hylands, P.J., Zenk, M.H. and Bacher, A. (1996) Proc. Nat. Acad. Sci. U.S.A. 93, 6431–6436.
Eisenreich, W., Sagner, S., Zenk, M.H. and Bacher, A. (1997) Tetrahedron Lett. 38, 3889–3892.
Lange, B.M., Wildling, M.R., McCaskill, D. and Croteau, R. (1998) Proc. Nat. Acad. Sci. U.S.A. (in press).
Mandel, M.A., Feldmann, K.A., Herrera-Estrella, L., Rocha-Sosa, M. and Leon, P. (1996) Plant J. 9, 649–658.
Tore, D., Bravo, J.M., Pale-Grosdemange, C. and Rohmer, M. (1997) Tetrahedron Lett. 38, 4769–4772.
Gershenzon, J. and Croteau, R. (1993) in Lipid Metabolism in Plants (Moore Jr, T.S., ed.), pp. 340–388, CRC Press, Boca Raton, FL.
Blanc, V.M. and Pichersky, E. (1995) Plant Physiol. 108, 855–856.
Croteau, R. (1987) Chem. Rev. 87, 929–954.
Clastre, M., Bantignies, B., Feron, G., Soler, E. and Ambid, C. (1993) Plant Physiol. 102, 205–211.
Suga, T. and Endo, T. (1991) Phytochemistry 30, 1757–1761.
Croteau, R. and Purkett, P.T. (1989) Arch. Biochem. Biophys. 271, 524–535.
Wise, M.L. and Croteau, R. (1998) in Comprehensive Natural Products Chemistry: Isoprenoids (Cane, D.E., ed.)Vol. 2, Elsevier Science, Oxford, UK (in press).
Colby, S.M., Alonso, W.R., Katahira, E.J., McGarvey, DJ. and Croteau, R. (1993) J. Biol. Chem. 268, 23016–23024.
Facchini, P.J. and Chappell, J. (1992) Proc. Nat. Acad. Sci. U.S.A. 89, 11088–11092.
Mau, C.J.D. and West, C.A. (1994) Proc. Nat. Acad. Sci. U.S.A. 91, 8497–8501.
Steele, C.L., Lewinsohn, E. and Croteau, R. (1995) Proc. Nat. Acad. Sci. U.S.A. 92, 4164–4168.
Yuba, A., Yazaki, K., Tabata, M., Honda, G. and Croteau, R. (1996) Arch. Biochem. Biophys. 332, 280–287.
Bohlman, I, Steele, C.L and Croteau, R.B. (1997) J. Biol. Chem. 272, 21784–21792.
Dudareva, N, Cseke, L., Blanc, V.M. and Pichersky, E. (1996) Plant Cell 8, 1137–1148.
Karp, F., Harris, J.L. and Croteau, R. (1987) Arch. Biochem. Biophys. 256, 179–193.
Lupien, S., Karp, F., Ponnamperuma, K., Wildung, M. and Croteau, R. (1996) Drug Metabol. Drug Interact. 12, 245–260.
Croteau, R. and Gershenzon, J. (1994) in Genetic Engineering of Plant Secondary Metabolism (Ellis, B.E., Kuroki, G. and Stafford, H.A., eds.), pp. 193–228, Plenum Press, New York, NY.
Croteau, R., Karp, F., Wagschal, K.C., Satterwhite, D.M., Hyatt, D.C. and Skotland, C.B. (1991) Plant Physiol. 96, 744–753.
Steele, C.L., Katoh, S., Bohlmann, J. and Croteau, R. (1998) Plant Physiol. (in press).
Croteau, R. (1988) in Flavors and Fragrances: A World Perspective (Lawrence, B.M., Mookherjee, B.D. and Willis, B.J., eds.), pp. 65–84, Elsevier, Amsterdam.
Berry, C., Van Eck, J.M., Kitto, S.L. and Smigocki, A. (1996) Plant Cell Tissue Organ Cult 44, 177–181.
Huang, Y., Diner, A.M. and Karnosky, D.F. (1991) In Vitro Cell. Dev. Biol. 27P, 201–207.
Buiatti, M. and Bogani, P. (1995) Euphytica 85, 135–147.
Guillen, M.D. and Manzanos, M.J. (1996) Food Res. Int. 29, 85–88.
Burkhardt, P.K., Beyer, P., Wunn, J., Kloti, A., Armstrong, G.A., Schledz, M., Von Lintg, J. and Potrykus, J (1997) Plant J. 11, 1071–1078.
Schaller, H, Grausem, B., Benveniste, P., Chye, M.-L., Tan, Y.-H, Song, Y.-H. and Chua, N.-H. (1995) Plant Physiol. 109, 761–770.
Hamilton, C.M., Frary, A., Lewis, C. and Tanksley, S.D. (1996) Proc. Nat. Acad. Sci. U.S.A. 93, 9975–9979.
Alonso, W.R. and Croteau, R. (1993) Methods Plant Biochem. 9, 239–260.
Depicker, A. and Van Montagu, M. (1997) Curr. Opin. Cell Biol. 9, 373–382.
Fray, R.G., Wallace, A., Fraser, P.D., Valero, D., Hedden, P., Bramley, P.M. and Grierson, D. (1995) Plant J. 8, 693–701.
Marks, M.D. (1997) Anna Rev. Plant Physiol. Plant Mol. Biol. 48, 137–163.
Gershenzon, J. (1994) J. Chem. Ecol. 20, 1281–1328.
Croteau, R. and Sood, V.K. (1985) Plant Physiol. 77, 801–806.
Ohloff, G. (1994) Scent and Fragrances, Springer-Verlag, New York, NY.
Koppenhoefer, B., Behnisch, R., Epperlein, U., Holzschuh, H., Bernreuther, A., Piras, P. and Roussel, C. (1994) Perfum. Flavor. 19, 1–14.
Berlin, J., Witte, L., Schubert, W. and Wray, V. (1984) Phytochemistry 23, 1277.
Buitelarr, R.M., Susaeta, I. and Tramper, J. (1990) in Progress in Plant Cellular and Molecular Biology (Nijkamp, H.J.J., Van der Plas, L.H.W, and Van Aartrijk, J., eds.), pp. 694–699, Kluwer, The Netherlands.
Funk, C., Koepp, A.E. and Croteau, R. (1992) Arch. Biochem. Biophys. 294, 306–313.
Spencer, A., Hamill, J.D. and Rhodes, M.J. (1993) Phytochemistry 32, 911–919.
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Haudenschild, C.D., Croteau, R.B. (1998). Molecular Engineering of Monoterpene Production. In: Setlow, J.K. (eds) Genetic Engineering. Genetic Engineering, vol 20. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1739-3_14
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DOI: https://doi.org/10.1007/978-1-4899-1739-3_14
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