Skip to main content
SpringerLink
Log in

Regulation of Monoterpene Biosynthesis in Higher Plants

  • Chapter
Biochemistry of the Mevalonic Acid Pathway to Terpenoids

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 24))

Abstract

Among the low molecular weight products of the mevalonate pathway in plants are the monoterpenes, the C10 representatives of the terpenoid family of natural products. Monoterpenes are colorless, lipophilic, volatile substances responsible for the characteristic odors of many plants. They have been reported from nearly 50 families of flowering plants,1 being best known as constituents of the essential oils of pines, mints and citrus fruits. Monoterpenes are classified as secondary metabolites because they do not appear to have any direct role in the basic processes of growth and development. Their functions in plants are still obscure, although, like other secondary metabolites, they may have ecological roles, serving as attractants to pollinators, allelopathic agents or defenses against predators and pathogens.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. BANTHORPE, D.V., B.V. CHARLWOOD. 1980. The terpenoids. In: Encyclopedia of Plant Physiology, New Series, Vol. 8, Secondary Plant Products. (E.A. Bell, B.V. Charlwood, eds.), Springer-Verlag, Berlin, pp. 185–220.

    Google Scholar 

  2. FAHN, A. 1979. Secretory Tissues in Plants. Academic Press, London, 302 pp.

    Google Scholar 

  3. CROTEAU, R. 1987. Biosynthesis and catabolism of monoterpenoids. Chem. Rev. 87: 929–954.

    CAS  Google Scholar 

  4. CROTEAU, R. 1988. Catabolism of monoterpenes in essential oil plants. In: Flavors and Fragrances: A World Perspective. (B.M. Lawrence, B.D. Mookherjee and B.J. Willis, eds.), Elsevier, Amsterdam, pp. 65–84.

    Google Scholar 

  5. PORTER, J.W., S.L. SPURGEON, eds. 1981. Biosynthesis of Isoprenoid Compounds, Vol. 1. John Wiley and Sons, New York, 558 pp.

    Google Scholar 

  6. DUGAN, R.E. 1981. Regulation of HMG-CoA reductase. In: Biosynthesis of Isoprenoid Compounds, Vol. 1. (J.W. Porter, S.L. Spurgeon, eds.), John Wiley and Sons, New York, pp. 95–159.

    Google Scholar 

  7. POULTER, C.D., H.C. RILLING. 1981. Prenyltransferases and isomerase. In: Biosynthesis of Isoprenoid Compounds, Vol. 1. (J.W. Porter, S.L. Spurgeon, eds.), John Wiley and Sons, New York, pp. 161–224.

    Google Scholar 

  8. CROTEAU, R. 1986. Biosynthesis of cyclic monoterpenes. In: Biogeneration of Aromas, ACS Symposium Series No. 317. (T.H. Parliment, R. Croteau, eds.), American Chemical Society, Washington, D.C., pp. 134–156.

    Google Scholar 

  9. GAMBLIEL, H., R. CROTEAU. 1984. Pinene cyclases I and II: Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration. J. Biol. Chem. 259: 740–748.

    PubMed  CAS  Google Scholar 

  10. CROTEAU, R., F. KARP. 1979. Biosynthesis of monoterpenes: Preliminary characterization of bornyl pyrophosphate synthetase from sage (Salvia officinalis) and demonstration that geranyl pyrophosphate is the preferred substrate for cyclization. Arch. Biochem. Biophys. 198: 512–522.

    PubMed  CAS  Google Scholar 

  11. CROTEAU, R., F. KARP. 1979. Biosynthesis of monoterpenes: Hydrolysis of bornyl pyrophosphate, an essential step in camphor biosynthesis, and hydrolysis of geranyl pyrophosphate, the acyclic precursor of camphor, by enzymes from sage (Salvia officinalis). Arch. Biochem. Biophys. 198: 523–532.

    PubMed  CAS  Google Scholar 

  12. CROTEAU, R., C.L. HOOPER, M. FELTON. 1978. Biosynthesis of monoterpenes: Partial purification and characterization of a bicyclic monoterpenol dehydrogenase from sage (Salvia officinalis). Arch. Biochem. Biophys. 188: 182–193.

    PubMed  CAS  Google Scholar 

  13. KARP, F., J.L. HARRIS, R. CROTEAU. 1987. Metabolism of monoterpenes: Demonstration of the hydroxylation of (+)-sabinene to (+)-cis-sabinol by an enzyme preparation from sage (Salvia officinalis) leaves. Arch. Biochem. Biophys. 256: 179–193.

    PubMed  CAS  Google Scholar 

  14. LUCKNER, M. 1984. Secondary Metabolism in Microorganisms, Plants and Animals, 2nd edition. Springer-Verlag, Berlin, 576 pp.

    Google Scholar 

  15. TAKEUCHI, A., K. OBA, I. URITANI. 1977. Change in acetyl-CoA synthetase activity of sweet potato in response to infection by Ceratocystis fimbriata and injury. Agric. Biol. Chem. 41: 1141–1145.

    CAS  Google Scholar 

  16. TAKEUCHI, A., M. YAMAGUCHI, I. URITANI. 1981. ATP Citrate lyase from Ipomoea batatas root tissue infected with Ceratocystis fimbriata. Phytochemistry 20: 1235–1239.

    CAS  Google Scholar 

  17. SABINE, J.R., ed. 1983. 3-Hydroxy-3-methylglutaryl Coenzyme A Reductase. CRC Press, Boca Raton, Florida, 271 pp.

    Google Scholar 

  18. RUSSELL, D.W. 1985. 3-Hydroxy-3-methylglutaryl-CoA reductases from pea seedlings. Meth. Enzymol. 110: 26–40.

    CAS  Google Scholar 

  19. SUZUKI, H., K. OBA, I. URITANI. 1975. The occurrence and some properties of 3-hydroxy-3-methylglutaryl coenzyme A reductase in sweet potato roots infected by Ceratocystis fimbriata. Physiol. Plant Pathol. 7: 2 65–276.

    Google Scholar 

  20. OBA, K., I. URITANI. 1979. Biosynthesis of furano-terpenes by sweet potato cell culture. Plant Cell Physiol. 20: 819–826.

    CAS  Google Scholar 

  21. OBA, K., K. KONDO, N. DOKE, I. URITANI. 1985. Induction of 3-hydroxy-3-methylglutaryl CoA reductase in potato tubers after slicing, fungal infection or chemical treatment, and some properties of the enzyme. Plant Cell Physiol. 26: 873–880.

    CAS  Google Scholar 

  22. STERMER, B.A., R.M. BOSTOCK. 1987. Involvement of 3-hydroxy-3-methylglutaryl coenzyme A reductase in the regulation of sesquiterpenoid phytoalexin synthesis in potato. Plant Physiol. 84: 404–408.

    PubMed  CAS  Google Scholar 

  23. VOGELI, U., J. CHAPPELL. 1988. Induction of sesquiterpene cyclase and suppression of squalene synthetase activities in plant cell cultures treated with fungal elicitor. Plant Physiol. 88: 1291–1296.

    PubMed  CAS  Google Scholar 

  24. CHAPPELL, J., R. NABLE. 1987. Induction of sesquiterpenoid biosynthesis in tobacco cell suspension cultures by fungal elicitor. Plant Physiol. 85: 469–473.

    PubMed  CAS  Google Scholar 

  25. BACH, T.J., H.K. LICHTENTHALER. 1982. Mevinolin: A highly specific inhibitor of microsomal 3-hydroxy-3-methylglutaryl-coenzyme A reductase of radish plants. Z. Naturforsch. 37c: 46–50.

    CAS  Google Scholar 

  26. CHAPPELL, J., C. VON LANKEN, U. VOGELI, P. BHATT. 1989. Sterol and sesquiterpenoid biosynthesis during a growth cycle of tobacco cell suspension cultures. Plant Cell Reports 8: 48–52.

    CAS  Google Scholar 

  27. LYNEN, F. 1967. Biosynthetic pathways from acetate to natural products. Pure Appl. Chem. 14: 137–167.

    PubMed  CAS  Google Scholar 

  28. HEPPER, C.M., B.G. AUDLEY. 1969. The biosynthesis of rubber from 3-hydroxy-3-methylglutaryl-coenzyme A in Hevea brasiliensis latex. Biochem. J. 114: 379–386.

    PubMed  CAS  Google Scholar 

  29. WITITSUWANNAKUL, R. 1986. Diurnal variation of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in latex of Hevea brasiliensis and its relation to rubber content. Experientia 42: 44–45.

    CAS  Google Scholar 

  30. BACH, T.J. 1986. Hydroxymethylglutaryl-CoA reductase, a key enzyme in phytosterol synthesis? Lipids 21: 82–88.

    PubMed  CAS  Google Scholar 

  31. NISHI, A., I. TSURITANI. 1983. Effect of auxin on the metabolism of mevalonic acid in suspension-cultured carrot cells. Phytochemistry 22: 399–401.

    CAS  Google Scholar 

  32. AREBALO, R.E., E.D. MITCHELL. 1984. Cellular distribution of 3-hydroxy-3-methylglutaryl coenzyme A reductase and mevalonate kinase in leaves of Nepeta cataria. Phytochemistry 23: 13–18.

    CAS  Google Scholar 

  33. BROOKER, J.D., D.W. RUSSELL. 1975. Subcellular localization of 3-hydroxy-3-methylglutaryl coenzyme A reductase in Pisum sativum seedlings. Arch. Biochem. Biophys. 167: 730–737.

    PubMed  CAS  Google Scholar 

  34. CAMARA, B., F. BARDAT, O. DOGBO, J. BRANGEON, R. MONEGER. 1983. Terpenoid metabolism in plastids: Isolation and biochemical characteristics of Capsicum annuum chromoplasts. Plant Physiol. 73: 94–99.

    PubMed  CAS  Google Scholar 

  35. RAMACHANDRA REDDY, A., V.S.R. DAS. 1986. Partial purification and characterization of 3-hydroxy-3-methylglutaryl coenzyme A reductase from the leaves of guayule (Parthenium argent atum). Phytochemistry 25: 2471–2474.

    Google Scholar 

  36. SUZUKI, H., I. URITANI. 1976. Subcellular localization of 3-hydroxy-3-methylglutaryl coenzyme A reductase and other membrane-bound enzymes in sweet potato roots. Plant Cell Physiol. 17: 691–700.

    CAS  Google Scholar 

  37. WONG, R.J., D.K. M.C. CORMACK, D.W. RUSSELL. 1982. Plastid 3-hydroxy-3-methylglutaryl coenzyme A reductase has distinctive kinetic and regulatory features: Properties of the enzyme and positive phytochrome control of activity in pea seedlings. Arch. Biochem. Biophys. 216: 631–638.

    PubMed  CAS  Google Scholar 

  38. BACH, T.J., H.K. LICHTENTHALER. 1982. Inhibition of mevalonate biosynthesis and of plant growth by the fungal metabolite mevinolin. In: Biochemistry and Metabolism of Plant Lipids. (J.F.G.M. Wintermans, P.J.C. Kuiper, eds.), Elsevier Biomedical Press, Amsterdam, pp. 515–521.

    Google Scholar 

  39. BACH, T.J. 1987. Synthesis and metabolism of mevalonic acid in plants. Plant Physiol. Biochem. 25: 163–178.

    CAS  Google Scholar 

  40. ITO, R., K. OBA, I. URITANI. 1979. Mechanism for the induction of 3-hydroxy-3-methylglutaryl coenzyme A reductase in HgCl2-treated sweet potato root tissue. Plant Cell Physiol. 20: 867–874.

    CAS  Google Scholar 

  41. OBA, K., H. TATEMATSU, K. YAMASHITA, I. URITANI. 1976. Induction of furano-terpene production and formation of the enzyme system from mevalonate to isopentenyl pyrophosphate in sweet potato root tissue injured by Ceratocystis fimbriata and by toxic chemicals. Plant Physiol. 58:5′-56.

    Google Scholar 

  42. NARITA, J.O., W. GRUISSEM. 1989. Tomato hydroxymethyl- glutaryl-CoA reductase is required early in fruit development but not during ripening. Plant Cell 1: 181–190.

    PubMed  CAS  Google Scholar 

  43. SIPAT, A.B. 1982. Hydroxymethylglutaryl CoA reductase (NADPH) in the latex of Hevea brasiliensis. Phytochemistry 21: 2613–2618.

    CAS  Google Scholar 

  44. SIPAT, A. 1985. 3-Hydroxy-3-methylglutaryl-CoA reductase in the latex of Hevea brasiliensis. Meth. Enzymol. 110: 40–51.

    CAS  Google Scholar 

  45. BACH, T.J., D.H. ROGERS, H. RUDNEY. 1986. Detergent-solubilization, purification, and characterization of membrane-bound 3-hydroxy-3-methylglutaryl-coenzyme A reductase from radish seedlings. Eur. J. Biochem. 154: 103–111.

    PubMed  CAS  Google Scholar 

  46. BROOKER, J.D., D.W. RUSSELL. 1975. Properties of microsomal 3-hydroxy-3-methylglutaryl coenzyme A reductase from Pisum sativum seedlings. Arch. Biochem. Biophys. 167: 723–729.

    PubMed  CAS  Google Scholar 

  47. BACH, T.J., H.K. LICHTENTHALER. 1984. Application of modified Lineweaver-Burk plots to studies of kinetics and regulation of radish 3-hydroxy-3-methylglutaryl-CoA reductase. Biochim. Biophys. Acta. 794: 152–161.

    PubMed  CAS  Google Scholar 

  48. CLEGG, R.J., B. MIDDLETON, G.D. BELL, D.A. WHITE. 1980. Inhibition of hepatic cholesterol synthesis and S-3-hydroxy-3-methylglutaryl-CoA reductase by mono and bicyclic monoterpenes administered in vivo. Biochem. Pharmacol. 29: 2125–2127.

    PubMed  CAS  Google Scholar 

  49. QURESHI, A.A., W.R. MANGELS, Z.Z. DIN, C.E. ELSON. 1988. Inhibition of hepatic mevalonate biosynthesis by the monoterpene, d-limonene. J. Agric. Food Chem. 36: 1220–1224.

    CAS  Google Scholar 

  50. ELSON, C.E., G.L. UNDERBAKKE, P. HANSON, E. SHRAGO, R.H. WAINBERG, A.A. QURESHI. 1989. Impact of lemongrass oil, an essential oil, on serum cholesterol. Lipids 24: 677–679.

    PubMed  CAS  Google Scholar 

  51. ISA, R.B.M., A.B. SIPAT. 1982. 3-Hydroxy-3-methylglutaryl CoA reductase of Hevea latex: The occurrence of a heat-stable activator in the C-serum. Biochem. Biophys. Res. Commun. 108: 206–212.

    PubMed  CAS  Google Scholar 

  52. LEARNED, R.M., G.R. FINK. 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: 2779–2783.

    PubMed  CAS  Google Scholar 

  53. DUDLEY, M.W., M.T. DUEBER, C.A. WEST. 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: 335–342.

    PubMed  CAS  Google Scholar 

  54. ATKINSON, D.E. 1969. Regulation of enzyme function. Ann. Rev. Microbiol. 23: 47–68.

    CAS  Google Scholar 

  55. KNOTZ, J., R.C COOLBAUGH, C.A. WEST. 1977. Regulation of the biosynthesis of ent-kaurene from mevalonate in the endosperm of immature Marah macrocarpus seeds by adenylate energy charge. Plant Physiol. 60: 81–85.

    PubMed  CAS  Google Scholar 

  56. SKILLETER, D.N., R.G.O. KEKWICK. 1971. The enzymes forming isopentenyl pyrophosphate from 5-phosphomevalonate (mevalonate 5-phosphate) in the latex of Hevea brasiliensis. Biochem. J. 124: 407–417.

    PubMed  CAS  Google Scholar 

  57. OGURA, K., T. KOYAMA, T. SHIBUYA, T. NISHINO, S. SETO. 1969. Inhibitory effect of substrate analogs on isopentenyl pyrophosphate isomerase and prenyltransferase. J. Biochem. 66: 117–118.

    PubMed  CAS  Google Scholar 

  58. LANDAU, B.R., H. BRUNEGRABER. 1985. Shunt pathway of mevalonate metabolism. Meth. Enzymol. 110: 100–114.

    PubMed  CAS  Google Scholar 

  59. NES, W.D., T.J. BACH. 1985. Evidence for a mevalonate shunt in a tracheophyte. Proc. R. Soc. Lond. B 225: 425–444.

    CAS  Google Scholar 

  60. SKRUKRUD, C.L., S.E. TAYLOR, D.R. HAWKINS, E.K. NEMETHY, M. CALVIN. 1988. Subcellular fractionation of triterpenoid biosynthesis in Euphorbia lathyris latex. Physiol. Plant. 74: 306–316.

    CAS  Google Scholar 

  61. WEST, C.A., M.W. DUDLEY, M.T. DUEBER. 1979. Regulation of terpenoid biosynthesis in higher plants. Rec. Adv. Phytochem. 13: 163–198.

    CAS  Google Scholar 

  62. DUDLEY, M.W., T.R. GREEN, C.A. WEST. 1986. Biosynthesis of the macrocyclic diterpene casbene in castor bean (Ricinus communis L.) seedlings: The purification and properties of farnesyl transferase from elicited seedlings. Plant Physiol. 81: 343–348.

    PubMed  CAS  Google Scholar 

  63. OGURA, K., T. SHINKA, S. SETO. 1972. The purification and properties of geranylgeranyl pyrophosphate synthetase from pumpkin fruit. J. Biochem. 72: 1101–1108.

    PubMed  CAS  Google Scholar 

  64. DE LA FUENTE, M., L.M. PEREZ, U. HASHAGEN, L. CHAYET, C. ROJAS, G. PORTILLA, O. CORI. 1981. Prenyltransferases from the flavedo of Citrus sinensis. Phytochemistry 20: 1551–1557.

    Google Scholar 

  65. PEREZ, L.M., R. LOZADA, O. CORI. 1983. Biosynthesis of allylic isoprenoid pyrophosphates by an enzyme preparation from the flavedo of Citrus paradisii. Phytochemistry 22: 431–433.

    CAS  Google Scholar 

  66. DOGBO, O., B. CAMARA. 1987. Purification of isopentenyl pyrophosphate isomerase and geranylgeranyl pyrophosphate synthase from Capsicum chromoplasts by affinity chromatography. Biochim. Biophys. Acta 92 0: 140–148.

    Google Scholar 

  67. CROTEAU, R., P.T. PURKETT. 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: 524–535.

    PubMed  CAS  Google Scholar 

  68. CROTEAU, R., M.A. JOHNSON. 1984. Biosynthesis of terpenoids in glandular trichomes. In: Biology and Chemistry of Plant Trichomes. (E. Rodriguez, P.L. Healy, I. Mehta, eds.), Plenum Publishing Co., New York, pp. 133–185.

    Google Scholar 

  69. GERSHENZON, J., M. MAFFEI, R. CROTEAU. 1989. Biochemical and histochemical localization of monoterpene biosynthesis in the glandular trichomes of spearmint (Mentha spicata). Plant Physiol. 89: 1351–1357.

    PubMed  CAS  Google Scholar 

  70. GERSHENZON, J., M.A. DUFFY, F. KARP, R. CROTEAU. 1987. Mechanized techniques for the selective extraction of enzymes from plant epidermal glands. Anal. Biochem. 163: 159–164.

    PubMed  CAS  Google Scholar 

  71. WIDMAIER, R., J. HOWE, P. HEINSTEIN. 1980. Prenyl-transferase from Gossypium hirsutum. Arch. Biochem. Biophys. 200: 609–616.

    PubMed  CAS  Google Scholar 

  72. SAGAMI, H., K. OGURA, S. SETO, T. KUROKAWA. 1978. A new prenyltransferase from Micrococcus lysodeikticus. Biochem. Biophys. Res. Comm. 85: 572–578.

    PubMed  CAS  Google Scholar 

  73. SAGAMI, H., K. OGURA. 1981. Geranylgeranyl pyrophosphate synthetase lacking geranyl-transferring activity from Micrococcus luteus. J. Biochem. 89: 1573–1580.

    PubMed  CAS  Google Scholar 

  74. HEIDE, L., U. BERGER. 1989. Partial purification and properties of geranyl pyrophosphate synthase from Lithospermum erythrorhizon cell cultures. Arch. Biochem. Biophys. 273: 331–338.

    PubMed  CAS  Google Scholar 

  75. PAULY, B., L. BELINGHERI, A. MARPEAU, M. GLEIZES. 1986. Monoterpene formation by leucoplasts of Citrofortunella mitis and Citrus unshiu: Steps and conditions of biosynthesis. Plant Cell Rep. 5: 19–22.

    CAS  Google Scholar 

  76. GLEIZES, M., G. PAULY, J.-P. CARDE, A. MARPEAU, C. BERNARD-DAGAN. 1983. Monoterpene hydrocarbon biosynthesis by isolated leucoplasts of Citrofortunella mitis. Planta 159: 373–381.

    CAS  Google Scholar 

  77. HEIDE, L. 1988. Geranylpyrophosphate synthase from cell cultures of Lithospermum erythrorhizon. FEBS Lett. 237: 159–162.

    CAS  Google Scholar 

  78. BRUENGER, E., H.C. RILLING. 1988. Determination of isopentenyl diphosphate and farnesyl diphosphate in tissue samples with a comment on secondary regulation of polyisoprenoid biosynthesis. Anal. Biochem. 173: 321–327.

    PubMed  CAS  Google Scholar 

  79. BANTHORPE, D.V., D.R.S. LONG, C.R. PINK. 1983. Biosynthesis of geraniol and related monoterpenes in Pelargonium graveolens. Phytochemistry 22: 2459–2463.

    CAS  Google Scholar 

  80. GREEN, T.R., D.J. BAISTED. 1971. Development of the squalene-synthesizing system during early stages of pea seed germination. Biochem. J. 125: 1145–1147.

    PubMed  CAS  Google Scholar 

  81. GREEN, T.R., D.J. BAISTED. 1972. Development of the activities of enzymes of the isoprenoid pathway during early stages of pea-seed germination. Biochem. J. 130: 983–995.

    PubMed  CAS  Google Scholar 

  82. BENEDICT, C.R. 1983. Biosynthesis of rubber. In: Biosynthesis of Isoprenoid Compounds, Vol. 2. (J.W. Porter, S.L. Spurgeon, eds.), John Wiley and Sons, New York, pp. 355–369.

    Google Scholar 

  83. RAMACHANDRA REDDY, A., V.S.R. DAS. 1988. Enhanced rubber accumulation and rubber transferase activity in guayule under water stress. J. Plant Physiol. 133: 152–155.

    Google Scholar 

  84. MADHAVAN, S., G.A. GREENBLATT, M.A. FOSTER, C.R. BENEDICT. 1989. Stimulation of isopentenyl pyrophosphate incorporation into polyisoprene in extracts from guayule plants (Parthenium argentatum Gray) by low temperature and 2-(3, 4-dichlorophenoxy) triethylamine. Plant Physiol. 89: 506–511.

    PubMed  CAS  Google Scholar 

  85. ARCHER, B.L., B.G. AUDLEY. 1987. New aspects of rubber biosynthesis. Bot. J. Linn. Soc. 94: 181–196.

    Google Scholar 

  86. LEUBE, J., H. GRISEBACH. 1983. Further studies on induction of enzymes of phytoalexin synthesis in soybean and cultured soybean cells. Z. Naturforsch. 38c: 730–735.

    CAS  Google Scholar 

  87. TIETJEN, K.G., U. MATERN. 1983. Differential response of cultured parsley cells to elicitors from two nonpathogenic strains of fungi. 2. Effects on enzyme activities. Eur. J. Biochem. 131: 409–413.

    PubMed  CAS  Google Scholar 

  88. HEIDE, L., M. TABATA. 1987. Geranylpyrophosphate:p-hydroxybenzoate geranyltransferase activity in extracts of Lithospermum erythrorhizon cell cultures. Phytochemistry 26: 1651–1655.

    CAS  Google Scholar 

  89. CROTEAU, R., A.J. BURBOTT, W.D. LOOMIS. 1972. Biosynthesis of mono- and sesquiterpenes in peppermint from glucose-14C and 14CO2 . Phytochemistry 11: 2459–2467.

    CAS  Google Scholar 

  90. CHARLWOOD, B.V., D.V. BANTHORPE. 1978. The biosynthesis of monoterpenes. In: Progress in Phytochemistry, Vol. 5. (L. Reinhold, J.B. Harborne, T. Swain, eds.), Pergamon Press, Oxford, pp. 65–125.

    Google Scholar 

  91. SHAH, D.H., W.W. CLELAND, J.W. PORTER. 1965. The partial purification, properties, and mechanisms of action of pig liver isopentenyl pyrophosphate isomerase. J. Biol. Chem. 240: 1946–1956.

    PubMed  CAS  Google Scholar 

  92. STEIGER, A., U. MITZKA-SCHNABEL, W. RAU, J. SOLL, W. RUDIGER. 1985. Inhibition of geranylgeranyl diphosphate synthesis in in vitro systems. Phytochemistry 24: 739–743.

    CAS  Google Scholar 

  93. CROTEAU, R., M. FELTON, F. KARP, R. KJONAAS. 1981. Relationship of camphor biosynthesis to leaf development in sage (Salvia officinalis). Plant Physiol. 67: 820–824.

    PubMed  CAS  Google Scholar 

  94. RAFFA, K.F., A.A. BERRYMAN. 1983. Physiological aspects of lodgepole pine wound responses to a fungal symbiont of the mountain pine beetle, Dendroctonus ponderosae (Coleoptera: Scolytidae). Can. Ent. 115: 723–734.

    Google Scholar 

  95. MILLER, R.H., A.A. BERRYMAN, C.A. RYAN. 1986. Biotic elicitors of defense reactions in lodgepole pine. Phytochemistry 25: 611–612.

    CAS  Google Scholar 

  96. CROTEAU, R., S. GURKEWITZ, M.A. JOHNSON, H.J. FISK. 1987. Biochemistry of oleoresinosis: Monoterpene and diterpene biosynthesis in lodgepole pine saplings infected with Ceratocystis clavigera or treated with carbohydrate elicitors. Plant Physiol. 85: 1123–1128.

    PubMed  CAS  Google Scholar 

  97. EL-KELTAWI, N.E., R. CROTEAU. 1987. Influence of foliar applied cytokinins on growth and essential oil content of several members of the Lamiaceae. Phytochemistry 26: 891–895.

    CAS  Google Scholar 

  98. MAURER, K.-H., D. MECKE. 1986. Regulation of enzymes involved in the biosynthesis of the sesquiterpene antibiotic pentalenolactone in Streptomyces arenae. J. Antibiotics 39: 266–271.

    CAS  Google Scholar 

  99. THRELFALL, D.R., I.M. WHITEHEAD. 1988. Co-ordinated inhibition of squalene synthetase and induction of enzymes of sesquiterpenoid phytoalexin biosynthesis in cultures of Nicotiana tabacum. Phytochemistry 27: 2567–2580.

    CAS  Google Scholar 

  100. BRINDLE, P.A., P.J. KUHN, D.R. THRELFALL. 1988. Biosynthesis and metabolism of sesquiterpenoid phytoalexins and triterpenoids in potato cell suspension cultures. Phytochemistry 27: 133–150.

    CAS  Google Scholar 

  101. MOESTA, P., C.A. WEST. 1985. Casbene synthetase: Regulation of phytoalexin biosynthesis in Ricinus communis L. seedlings. Arch. Biochem. Biophys. 238: 325–333.

    PubMed  CAS  Google Scholar 

  102. CANE, D.E., C. PARGELLIS. 1987. Partial purification and characterization of pentalenene synthase. Arch. Biochem. Biophys. 254: 421–429.

    PubMed  CAS  Google Scholar 

  103. CROTEAU, R., F. KARP. 1976. Biosynthesis of monoterpenes: Enzymatic conversion of neryl pyrophosphate to 1,8-cineole, α-terpineol, and cyclic monoterpene hydrocarbons by a cell-free preparation from sage (Salvia officinalis). Arch. Biochem. Biophys. 176: 734–746.

    PubMed  CAS  Google Scholar 

  104. CROTEAU, R., F. KARP. 1977. Biosynthesis of monoterpenes: Partial purification and characterization of 1,8-cineole synthetase from Salvia officinalis. Arch. Biochem. Biophys. 179: 257–265.

    PubMed  CAS  Google Scholar 

  105. POULOSE, A.J., R. CROTEAU. 1978. γ-Terpinene synthetase: A key enzyme in the biosynthesis of aromatic monoterpenes. Arch. Biochem. Biophys. 191: 400–411.

    PubMed  CAS  Google Scholar 

  106. WHITEHEAD, I.M., D.R. THRELFALL, D.F. EWING. 1989. 5-epi-Aristolochene is a common precursor of the sesquiterpenoid phytoalexins capsidiol and debneyol. Phytochemistry 28: 775–779.

    CAS  Google Scholar 

  107. ROGERS, L.J., S.P.J. SHAH, T.W. GOODWIN. 1968. Compartmentation of biosynthesis of terpenoids in green plants. Photosynthetica 2: 184–207.

    CAS  Google Scholar 

  108. RAMACHANDRA REDDY, A., V.S.R. DAS. 1987. Chloroplast autonomy for the biosynthesis of isopentenyl diphosphate in guayule (Partheniuzn argentatum Gray). New Phytol. 106: 457–464.

    Google Scholar 

  109. SCHULZE-SIEBERT, D., A. HEINTZE, G. SCHULTZ. 1987. Substrate flow from photosynthetic carbon metabolism to chloroplast isoprenoid synthesis in spinach: Evidence for a plastidic phosphoglycerate mutase. Z. Naturforsch. 42c: 570–580.

    Google Scholar 

  110. KREUZ, K., H. KLEINIG. 1981. On the compartmentation of isopentenyl diphosphate synthesis and utilization in plant cells. Planta 153: 578–581.

    CAS  Google Scholar 

  111. KREUZ, K., H. KLEINIG. 1984. Synthesis of prenyl lipids in cells of spinach leaf: Compartmentation of enzymes for formation of isopentenyl diphosphate. Eur. J. Biochem. 141: 531–535.

    PubMed  CAS  Google Scholar 

  112. CARDE, J.-P. 1984. Leucoplasts: A distinct kind of organelles lacking typical 70S ribosomes and free thylakoids. Eur. J. Cell Biol. 34: 18–26.

    PubMed  CAS  Google Scholar 

  113. SCHNEPF, E. 1974. Gland cells. In: Dynamic Aspects of Plant Ultrastructure. (A.W. Roberts, ed.), McGraw-Hill, New York, pp. 331–357.

    Google Scholar 

  114. BOSABALIDIS, A., I. TSEKOS. 1982. Ultrastructural studies on the secretory cavities of Citrus deliciosa Ten. I. Early stages of gland cell differentiation. Protoplasma 112: 55–62.

    Google Scholar 

  115. CHENICLET, C., J.-P. CARDE. 1985. Presence of leucoplasts in secretory cells and of monoterpenes in the essential oil: A correlative study. Israel J. Bot. 34: 219–238.

    Google Scholar 

  116. METTAL, U., W. BOLAND, P. BEYER, H. KLEINIG. 1988. Biosynthesis of monoterpene hydrocarbons by isolated chromoplasts from daffodil flowers. Eur. J. Biochem. 170: 613–616.

    PubMed  CAS  Google Scholar 

  117. FALK, H., B. LIEDVOGEL, P. SITTE. 1974. Circular DNA in isolated chromoplasts. Z. Naturforsch. 29c: 541–544.

    CAS  Google Scholar 

  118. LIEDVOGEL, B., P. SITTE, H. FALK. 1976. Chromoplasts in the daffodil: Fine structure and chemistry. Cytobiologie 12: 155–174.

    CAS  Google Scholar 

  119. CHAYET, L., C. ROJAS, E. CARDEMIL, A.M. JABALQUINTO, R. VICUNA, O. CORI. 1977. Biosynthesis of monoterpene hydrocarbons from [l-3H]neryl pyrophosphate and [1-3H]geranyl pyrophosphate by soluble enzymes from Citrus limonum. Arch. Biochem. Biophys. 180: 318–327.

    PubMed  CAS  Google Scholar 

  120. AMELUNXEN, F. 1965. Electronenmikroskopisch Untersuchungen an den Drusenschuppen von Mentha piperita L. Planta Med. 13: 457–473.

    Google Scholar 

  121. WOODING, F.B.P., D.H. NORTHCOTE. 1965. The fine structure of the mature resin cells of Pinus pinea. J. Ultrastr. Res. 13: 233–244.

    CAS  Google Scholar 

  122. BOSABALIDIS, A., I. TSEKOS. 1982. Glandular scale development and essential oil secretion in Origanum dictamnus L. Planta 156: 496–504.

    Google Scholar 

  123. CROTEAU, R., K.V. VENKATACHALAM. 1986. Metabolism of monoterpenes: Demonstration that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint (Mentha piperita). Arch. Biochem. Biophys. 249: 306–315.

    PubMed  CAS  Google Scholar 

  124. CROTEAU, R., C.L. HOOPER. 1978. Metabolism of monoterpenes: Acetylation of (-)-menthol by a soluble enzyme preparation from peppermint (Mentha piperita) leaves. Plant Physiol. 61: 737–742.

    PubMed  CAS  Google Scholar 

  125. POTTY, V.H., J.H. BRUEMMER. 1970. Oxidation of geraniol by an enzyme system from orange. Phytochemistry 9: 1003–1007.

    Google Scholar 

  126. KJONAAS, R., C. MARTINKUS-TAYLOR, R. CROTEAU. 1982. Metabolism of monoterpenes: Conversion of 1-menthone to 1-menthol and d-neomenthol by stereospecific dehydrogenases from peppermint (Mentha piperita) leaves. Plant Physiol. 69: 1013–1017.

    PubMed  CAS  Google Scholar 

  127. KJONAAS, R.B., K.V. VENKATACHALAM, R. CROTEAU. 1985. Metabolism of monoterpenes: Oxidation of isopiperitenol to isopiperitenone, and subsequent isomerization to piperitenone by soluble enzyme preparations from peppermint (Mentha piperita) leaves. Arch. Biochem. Biophys. 238: 49–60.

    PubMed  CAS  Google Scholar 

  128. DEHAL, S.S., R. CROTEAU. 1987. Metabolism of monoterpenes: Specificity of the dehydrogenases responsible for the biosynthesis of camphor, 3-thujone, and 3-isothujone. Arch. Biochem. Biophys. 258: 287–291.

    PubMed  CAS  Google Scholar 

  129. CROTEAU, R., C.L. HOOPER, M. FELTON. 1978. Biosynthesis of monoterpenes: Partial purification and characterization of bicyclic monoterpenol dehydrogenase from sage (Salvia officinalis). Arch. Biochem. Biophys. 188: 182–193.

    PubMed  CAS  Google Scholar 

  130. CROTEAU, R., N.M. FELTON. 1980. Substrate specificity of monoterpenol dehydrogenases from Foeniculum vulgare and Tanacetum vulgare. Phytochemistry 19: 1343–1347.

    CAS  Google Scholar 

  131. BERNARD-DAGAN, C., G. PAULY, A. MARPEAU, M. GLEIZES, J.- P. CARDE, P. BARADAT. 1982. Control and compartmentation of terpene biosynthesis in leaves of Pinus pinaster. Physiol. Veg. 20: 775–795.

    CAS  Google Scholar 

  132. BELINGHERI, L., G. PAULY, M. GLEIZES, A. MARPEAU. 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.

    CAS  Google Scholar 

  133. GLEIZES, M., J.-P. CARDE, G. PAULY, C. BERNARD-DAGAN. 1980. In vivo formation of sesquiterpene hydrocarbons in the endoplasmic reticulum of pine. Plant Sci. Lett. 20: 79–90.

    CAS  Google Scholar 

  134. CROTEAU, R., A. GUNDY. 1984. Cyclization of farnesyl pyrophosphate to the sesquiterpene olefins humulene and caryophyllene by an enzyme system from sage (Salvia officinalis). Arch. Biochem. Biophys. 233: 838–841.

    PubMed  CAS  Google Scholar 

  135. DEHAL, S.S., R. CROTEAU. 1988. Partial purification and characterization of two sesquiterpene cyclases from sage (Salvia officinalis) which catalyze the respective conversion of farnesyl pyrophosphate to humulene and caryophyllene. Arch. Biochem. Biophys. 261: 346–356.

    PubMed  CAS  Google Scholar 

  136. CROTEAU, R., S.L. MUNCK, C.C. AKOH, H.J. FISK, D.M. SATTERWHITE. 1987. Biosynthesis of the sesquiterpene patchoulol from farnesyl pyrophosphate in leaf extracts of Pogostemon cablin (patchouli): Mechanistic considerations. Arch. Biochem. Biophys. 256: 56–68.

    PubMed  CAS  Google Scholar 

  137. KUDAKASSERIL, G.J., L. LAM, E.J. STABA. 1987. Effect of sterol inhibitors on the incorporation of 14C-isopentenyl pyrophosphate into artemisinin by a cell-free system from Artemisia annua tissue cultures and plants. Planta Med. 280–284.

    Google Scholar 

  138. SIMCOX, P.D., D.T. DENNIS, C.A. WEST. 1975. Kaurene synthetase from plastids of developing plant tissues. Biochem. Biophys. Res. Comm. 66: 166–172.

    PubMed  CAS  Google Scholar 

  139. RAILTON, I.D., B. FELLOWS, C.A. WEST. 1984. ent-Kaurene synthesis in chloroplasts from higher plants. Phytochemistry 23: 1261–1267.

    CAS  Google Scholar 

  140. LUCKNER, M., B. DIETTRICH, W. LERBS. 1980. Cellular compartmentation and channeling of secondary metabolism in microorganisms and higher plants. In: Progress in Phytochemistry, Vol. 6. (L. Reinhold, J.B. Harborne, T. Swain, eds.), Pergamon Press, Oxford, pp. 103–142.

    Google Scholar 

  141. SCHNEIDER, M.M., R. HAMPP, H. ZIEGLER. 1977. Envelope permeability to possible precursors of carotenoid biosynthesis during chloroplast-chromoplast transformation. Plant Physiol. 60: 518–520.

    PubMed  CAS  Google Scholar 

  142. GLEIZES, M., B. CAMARA, J. WALTER. 1987. Some characteristics of terpenoid biosynthesis by leucoplasts of Citrofortunella mitis. Planta 170: 138–140.

    CAS  Google Scholar 

  143. REED, L.J., D.J. COX.. 1970. Multienzyme complexes. In: The Enzymes: Structure and Control, Vol. 1. (P.D. Boyer, ed.), Academic Press, New York, pp. 213–240.

    Google Scholar 

  144. STAFFORD, H.A. 1981. Compartmentation in natural product biosynthesis by multienzyme complexes. In: The Biochemistry of Plants, Vol. 7, Secondary Plant Products. (E.E. Conn, ed.), Academic Press, New York, pp. 117–137.

    Google Scholar 

  145. MAUDINAS, B., M.L. BUCHOLTZ, C. PAPASTEPHANOU, S.S. KATIYAR, A.V. BRIEDIS, J.W. PORTER. 1977. The partial purification and properties of a phytoene synthesizing enzyme system. Arch. Biochem. Biophys. 180: 354–362.

    PubMed  CAS  Google Scholar 

  146. LUTZOW, M., P. BEYER. 1988. The isopentenyl-diphosphate A-isomerase and its relation to the phytoene synthase complex in daffodil chromoplasts. Biochim. Biophys. Acta 959: 118–126.

    Google Scholar 

  147. LOOMIS, W.D., R. CROTEAU. 1973. Biochemistry and physiology of lower terpenoids. Rec. Adv. Phytochem. 6: 147–186.

    CAS  Google Scholar 

  148. CROTEAU, R., W.D. LOOMIS. 1972. Biosynthesis of mono-and sesquiterpenes in peppermint from mevalonate-2-14C. Phytochemistry 11: 1055–1066.

    CAS  Google Scholar 

  149. KEENE, C.K., G.J. WAGNER. 1985. Direct demonstration of duvatrienediol biosynthesis in glandular heads of tobacco trichomes. Plant Physiol. 79: 1026–1032.

    PubMed  CAS  Google Scholar 

  150. CROTEAU, R., W.D. LOOMIS. 1973. Biosynthesis of squalene and other triterpenes in Mentha piperita from mevalonate-2-14C. Phytochemistry 12: 1957–1965.

    CAS  Google Scholar 

  151. BERNARD-DAGAN, C., J. P. CARDE, M. GLEIZES. 1979. Etude des composes terpiniques au cours de la croissance des aiguilles du Pin maritime: comparaison de donnees biochimiques et ultrastructurales. Can. J. Bot. 57: 255–263.

    CAS  Google Scholar 

  152. BANTHORPE, D.V., O. EKUNDAYO. 1976. Biosynthesis of (+)-car-3-ene in Pinus species. Phytochemistry 15: 109–112.

    CAS  Google Scholar 

  153. HEINRICH, G., W. SCHULTZE, I. PFAB, M. BOTTGER. 1983. The site of essential oil biosynthesis in Poncirus trifoliata and Monarda fistulosa. Physiol. Veg. 21: 257–268.

    CAS  Google Scholar 

  154. FRANCIS, M.J.O., M. O’CONNELL. 1969. The incorporation of mevalonic acid into rose petal monoterpenes. Phytochemistry 8: 1705–1708.

    CAS  Google Scholar 

  155. STUBBS, J.M., M.J.O. FRANCIS. 1971. Electron microscopical studies of rose petal cells during flower maturation. Planta Med. 20: 211–218.

    PubMed  CAS  Google Scholar 

  156. CROTEAU, R., A.J. BURBOTT, W.D. LOOMIS. 1972. Apparent energy deficiency in mono- and sesquiterpene biosynthesis in peppermint. Phytochemistry 11: 2937–2948.

    CAS  Google Scholar 

  157. MIHALIAK, C.A., D.E. LINCOLN. 1989. Changes in leaf mono- and sesquiterpene metabolism with nitrate availability and leaf age in Heterotheca subaxillaris. J. Chem. Ecol. 15: 1579–1588.

    CAS  Google Scholar 

  158. BURBOTT, A.J., W.D. LOOMIS. 1969. Evidence for metabolic turnover of monoterpenes in peppermint. Plant Physiol. 44: 173–179.

    PubMed  CAS  Google Scholar 

  159. GLEIZES, M., G. PAULY, C. BERNARD-DAGAN, R. JACQUES. 1980. Effects of light on terpene hydrocarbon synthesis in Pinus pinaster. Physiol. Plant. 50: 16–20.

    CAS  Google Scholar 

  160. YAMAURA, T., S. TANAKA, M. TABATA. 1989. Light-dependent formation of glandular trichomes and monoterpenes in thyme seedlings. Phytochemistry 28: 741–744.

    CAS  Google Scholar 

  161. FIRMAGE, D.H. 1981. Environmental influences on the monoterpene variation in Hedeoma drummondii. Biochem. Syst. Ecol. 9: 53–58.

    CAS  Google Scholar 

  162. BURBOTT, A.J., W.D. LOOMIS. 1967. Effects of light and temperature on the monoterpenes of peppermint. Plant Physiol. 42: 20–28.

    PubMed  CAS  Google Scholar 

  163. HORNOK, L. 1978. [cited in Bernath, J. 1986. Production ecology of secondary plant products. In: Herbs, Spices and Medicinal Plants: Recent Advances in Botany, Horticulture and Pharmacology, Vol. 1. (L.E. Craker, J.E. Simon, eds.), Oryx Press, Phoenix, Arizona, pp. 185–234.]

    Google Scholar 

  164. LINCOLN, D.E., J.H. LANGENHEIM. 1978. Effect of light and temperature on monoterpenoid yield and composition in Satureja douglasii. Biochem. Syst. Ecol. 6: 21–32.

    CAS  Google Scholar 

  165. TANAKA, S., T. YAMAURA, M. TABATA. 1987. Localization and biosynthetic regulation of monoterpenoids in thyme seedlings. Abstract, Bioflavour ‘87, International Conference, University of Wurzburg, West Germany, September 29–30, 1987.

    Google Scholar 

  166. TANAKA, S., T. YAMAURA, M. TABATA. 1988. Localization and photoregulation of monoterpenoid biosynthesis in thyme seedlings. In: Bioflavour ‘87: Analysis, Biochemistry, Biotechnology. (P. Schreier, ed.), Walter de Gruyter, Berlin, pp. 237–241.

    Google Scholar 

  167. LINCOLN, D.E., D. COUVET. 1989. The effect of carbon supply on allocation to allelochemicals and caterpillar consumption of peppermint. Oecologia 78: 112–114.

    Google Scholar 

  168. FAJER, E.D., M.D. BOWERS, F.A. BAZZAZ. 1989. The effects of enriched carbon dioxide atmospheres on plant-insect herbivore interactions. Science 243: 1198–1200.

    PubMed  CAS  Google Scholar 

  169. CROTEAU, R. 1977. Site of monoterpene biosynthesis in Majorana hortensis leaves. Plant Physiol. 59: 519–520.

    PubMed  CAS  Google Scholar 

  170. KJONAAS, R., R. CROTEAU. 1983. Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha piperita and other Mentha species. Arch. Biochem. Biophys. 220: 79–89.

    PubMed  CAS  Google Scholar 

  171. KARP, F., C.A. MIHALIAK, J.L. HARRIS, R. CROTEAU. 1990. Monoterpene biosynthesis: Specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata) and perilla (Perilla frutescens) leaves. Arch. Biochem. Biophys. (in press).

    Google Scholar 

  172. BANTHORPE, D.V. 1988. Monoterpenes and sesquiterpenes. In: Cell Culture and Somatic Cell Genetics, Vol. 5, Phytochemicals in Plant Cell Cultures. (F. Constabel, I.K. Vasil, eds.), Academic Press, San Diego, pp. 143–157.

    Google Scholar 

  173. CHARLWOOD, B.V., J.T. BROWN, C. MOUSTOU, G.S. MORRIS, K.A. CHARLWOOD. 1988. The accumulation of isoprenoid flavour compounds in plant cell cultures. In: Bioflavour ‘87: Analysis, Biochemistry, Biotechnology. (P. Schreier, ed.), Walter de Gruyter, Berlin, pp. 303–314.

    Google Scholar 

  174. MULDER-KRIEGER, T., R. VERPOORTE, A. BAERHEIM SVENDSEN, J.J.C. SCHEFFER. 1988. Production of essential oils and flavours in plant cell and tissue cultures. A review. Plant Cell, Tissue and Organ Culture 13: 85–154.

    CAS  Google Scholar 

  175. BECKER, H. 1970. Studies on the formation of volatile substances in plant tissue cultures. Biochem. Physiol. Pflanzen 161: 425–441.

    CAS  Google Scholar 

  176. BRICOUT, J., C. PAUPARDIN. 1975. Sur la composition de l’huile essentielle de Mentha piperita L. cultivee in vitro: influence de quelques facteurs sur sa synthese. C. R. Acad. Sci. Paris Ser. D 281: 383–386.

    CAS  Google Scholar 

  177. BRICOUT, J., M.-J. GARCIA-RODRIGUEZ, C. PAUPARDIN, R. SAUSSAY. 1978. Biosynthese de composes monoterpeniques par les tissus de quelques especes de Menthes cultivees in vitro. C. R. Acad. Sci. Paris Ser. D 287: 611–613.

    CAS  Google Scholar 

  178. WINK, M. 1984. Evidence for an extracellular lytic compartment of plant cell suspension cultures: The cell culture medium. Naturwiss. 71: 635–637.

    CAS  Google Scholar 

  179. BROWN, J.T., P.K. HEGARTY, B.V. CHARLWOOD. 1987. The toxicity of monoterpenes to plant cell cultures. Plant Sci. 48: 195–201.

    CAS  Google Scholar 

  180. CARRIERE, F., G. GIL, P. TAPIE, P. CHAGVARDIEFF. 1989. Biotransformation of geraniol by photoautotrophic, photomixotrophic and heterotrophic plant cell suspensions. Phytochemistry 28: 1087–1090.

    CAS  Google Scholar 

  181. BERGER, R.G., F. DRAWERT. 1988. Glycosylation of terpenols and aromatic alcohols by cell suspension cultures of peppermint (Mentha piperita L.). Z. Naturforsch. 43c: 485–490.

    Google Scholar 

  182. CORMIER, F., C. AMBID. 1987. Extractive bioconversion of geraniol by a Vitis vinifera cell suspension employing a two-phase system. Plant Cell Rep. 6: 427–430.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Biological Chemistry, Washington State University, Pullman, WA, 99164-6340, USA

    Jonathan Gershenzon & Rodney Croteau

Authors
  1. Jonathan Gershenzon
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rodney Croteau
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. University of British Columbia, Vancouver, British Columbia, Canada

    G. H. Neil Towers

  2. Reed College, Portland, Oregon, USA

    Helen A. Stafford

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Plenum Press, New York

About this chapter

Cite this chapter

Gershenzon, J., Croteau, R. (1990). Regulation of Monoterpene Biosynthesis in Higher Plants. In: Towers, G.H.N., Stafford, H.A. (eds) Biochemistry of the Mevalonic Acid Pathway to Terpenoids. Recent Advances in Phytochemistry, vol 24. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-8789-3_3

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-8789-3_3

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-8791-6

  • Online ISBN: 978-1-4684-8789-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation