Monoterpenes, biosynthesis

Figure 9.4 Monoterpene biosynthesis in peppermint oil gland secretory cells. The enzymes involved in this pathway are (1) 1-deoxy-D-xylulose 5-phosphate synthase, (2) 2-C-methyl-D-erythritol 4-phosphate reductoisomerase, (3) 2-C-methyl-D-erythritol 4-phosphate cytidyltransferase, (4) 4-(cytidine 5 -diphospho)-2-C-methyl-D-erythritol kinase, (5) 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, (6) isopentenyl diphosphate isomerase, (7) geranyl diphosphate synthase, (8)...

Turner GW, Croteau R (2004) Organization of monoterpene biosynthesis in Mentha. Immunocytochemical localizations of geranyl diphosphate synthase, Umonene-6-hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase. Plant Physiol 136 4215 227... 

Wise ML, Croteau R (1999) Monoterpene biosynthesis. In Barton D, Nakanishi K, Meth-Cohn O (eds) Comprehensive natural products chemistry, vol. 2. Elsevier Science, Oxford, pp 97-153... 

Karp F, Croteau R, Role of hydroxylases in monoterpene biosynthesis, in Schreier P (ed.). Bioflavor 87, Walter de Gruyter, Berfln, Germany, pp. 173—198, 1988. 

Croteau, R. B. In Flavor Precursors Teranishi, R. Takeoka, G. R. Guntert, M., Eds. Monoterpene Biosynthesis cyclization of geranyl pyrophosphate to (+)-sabinene Amercian Chemicd Society Symposium Seriers 490 Washington, DC, 1991, pp. 8-20. 

Polzin JJ, Rorrer GL, Cheney DP (2003) Metabolic Flux Analysis of Halogenated Monoterpene Biosynthesis in Microplantlets of the Macrophytic Red Alga Ochtodes secundiramea. Biomol Eng 20 205... 

Croteau, R., Miyazaki, J.H. and Wheeler, C.J. (1989) Monoterpene biosynthesis mechanistic evaluation of the geranyl pyrophosphate (-)-encfo-fenchol cyclase from fennel (Foeniculum vulgare). Archives of Biochemistry and Biophysics 269(2), 507-516. 

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. 

Turner, G., Gershenzon, J., Nielson, E.E., Eroehlich, J.E. and Croteau, R. (1999) Limonene s)mthase, the enzyme responsible for monoterpene biosynthesis in peppermint, is localized to leucoplasts of oil gland secretory cells. Plant Physiol., 120, 879-86. 

Wise, M.L. and Croteau, R. (1998) Monoterpene biosynthesis, in Comprehensive Natural Products Chemistry Isoprenoid Biosynthesis (ed. D.E. Cane). Pergamon, Oxford. 

Research over the last few years has revealed that the flavor compounds are not end products of monoterpene biosynthesis in the grape. Oxidative pathways, leading to flavorless polyhydroxylated forms of the monoterpenes, are active in Vitis vinifera. Also, the... 

Wise ML, Croteau R. Monoterpene biosynthesis. In Isoprenoids, Including Carotenoids and Steroids. Cane DE, ed. 1999. Elsevier, London, pp. 97-153. 

OLDHAM, N.J., VEITH, M., BOLAND, W., Iridoid monoterpene biosynthesis in insects evidence for a de novo pathway occurring in the defensive glands of Phaedon armoraciae (Chrysomelidae) leaf beetle larvae, Naturwissenschaften, 1996,83,470-473. 

Monoterpene biosynthesis has been studied in conifers using labeled precursors such as carbon dioxide, acetate and mevalonate (63,64). Specifically labeled precursors have been employed to deduce mechanistic features of a-plnene (65,66) and 3-carene (67,68) biosynthesis in pine species. Glelzes and co-workers (69) have argued, by way of time-course studies, that the initial formation of acyclic hydrocarbons (oclmene, myrcene) from C02 in Pinus pinaster needles indicated that these olefins serve as precursors to cyclic monoterpenes (a-plnene, 8-pinene) by a reversible protonatlon mechanism. These suggestions, however, are without precedent, and run counter to direct evidence demonstrating that the cyclizatlon of geranyl pyrophosphate occurs without the involvement of free intermediates (17). 

Gershenzon, j. and R. Croteau, Regulation of monoterpene biosynthesis, in Biochemistry of the Mevalonic Acid Pathway to Terpenoids (G. H. N. Towers and H. A. Stafford, eds.). Recent Advances in Phytochemistry Vol. 24, 99-160, Plenum Press, New York, 1990. 

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