Terpenoids biosynthesis

Figure 27.8 An overview of terpenoid biosynthesis from isopentenyl diphosphate.

Chapter 27, Biomolecules Lipids—The chapter has been extensively revised, with increased detail on prostaglandins (Section 27.4), terpenoid biosynthesis (Section 27.5), and steroid biosynthesis, (Section 27.7). 

Rohmer, M., Seemann, M., Horbach, S. et al. (1996) Glyceraldehyde 3-phosphate and pyruvate as precursors of isoprenic units in an alternative non-mevalonate pathway for terpenoid biosynthesis. Journal of the American... 

THRELFALL, D.R., WHITEHEAD, I.M., Redirection of terpenoid biosynthesis in elicitor-treated plant cell suspension cultures. In Plant Lipid Biochemistry (P.J. Quinn and J.L. Harwood, eds,), Portland Press, London. 1990, pp. 344-346. 

McCASKILL, D., CROTEAU, R., Isopentenyl diphosphate is the terminal product of the deoxyxylulose 5-phosphate pathway for terpenoid biosynthesis in plants, Tetrahedron Lett., 1999,40,653-656. 

ARIGONI, D., EISENREICH, W, LATZEL, C., SAGNER, S., RADYKEWICZ, T, ZENK, M.H., BACHER, A., Dimethylallyl pyrophosphate is not the committed precursor of isopentenyl pyrophosphate during terpenoid biosynthesis from 1-deoxyxylulose in higher plants, Proc. Natl. Acad. Sci. USA, 1999, 96,1309-1314. 

KUZUYAMA, T., SHIMIZU, T., TAKAHASHI, S., SETO, H., Fosmidomycin, a specific inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in the nonmevalonate pathway for terpenoid biosynthesis, Tetrahedron Lett., 1998, 39, 7913-7916. 

Dubey VS, Bhalla R, Luthra R (2003) An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants. J Biosci 28 637-646... 

Biotin metabolism Folate biosynthesis One carbon pool by folate Retinol metabolism Porphyrin and chlorophyll metabolism Terpenoid biosynthesis Xenobiotics metabolism Ubiquinone biosynthesis Flavonoids, stilbene, and lignin biosynthesis... 

Aharoni A, Jongsma MA, Kim T-Y, Ri M-B, Giri AP, Verstappen FWA, Schwab W, Bouwmeester HJ (2006) Metabolic engineering of terpenoid biosynthesis in plants. Phytochem Rev 5 49-58... 

ThrelfaU DR, Whitehead IM (1990) Redirection of terpenoid biosynthesis in eUcitor-treated plant cell suspension cultines. In Qninn PJ, Harwood JL (eds) Plant lipid biochemistry. Portland Press, London, p 344... 

Fig. 4.2 Terpenoid biosynthesis sites and products (metabolites) (reprinted from Rohmer [46], copyright 2006, with kind permission from Elsevier)...

Gershenzon, J. and Croteau, R. (1993). Terpenoid biosynthesis the basic pathway and formation of monoterpenes, sesquiterpenes and diterpenes. In Lipid Metabolism in Plants, ed. T. S. Moore Jr, pp. 339-388. Boca Raton, FL CRC Press. 

S ATP + 4-(cytidine 5 -diphospho)-2-C-methyl-D-erythritol <1> (<1> involved in terpenoid biosynthesis via deoxyxylulose phosphate pathway... 

Eisenreich W, Schwarz M, Cartayrade A, Arigoni D, Zenk MH and Bacher A (1998) The deoxyxy-lulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms. Chem Biol 5, R221-R233. 

If sterol content and conformation are so important for membrane stability, we should study the biosynthesis of sterols (Figure 3). The first enzyme in terpenoid biosynthesis is the 3-Hydroxy-3-Methyl-Glutary1-Coenzyme A-reductase (HMG-CoA-reductase) that catalyzes the synthesis of mevalonate. Two phosphorylations and decarboxylation of mevalonate lead to isopentenylpyrophosphate, the basic C -unit in sterol synthesis. Isopentenylpyrophosphate reacts with its isomer, the dimethylally1-pyrophosphate, in a head/tail-reaction to geranyl-pyrophosphate reaction with another C -unit leads to farnesyl-pyro-phosphate, that dimerizes in a tail/tail-reaction to squalene. After expoxidation of its A -double bond, squalene cyclizes to lano-... 

Another target, that at first seems to be unfavorable since it is principally common for all organisms, is the enzyme HMG-CoA-reduc-tase which is the regulatory enzyme in terpenoid biosynthesis. Results from trials with naturally produced inhibitors for that enzyme, such as Compactine and Mevinoline, indicate that these compounds are able to lower the cholesterol content in mammals, but not markedly depress sterol synthesis in fungi U3). 

Evans, R., Hanson, J.R. "Studies In terpenoid biosynthesis. Part XIII. The biosynthetic relationship of the gibberellins in Gibberella fujikuroi." J.C.S. Perkin Trans., 1975 1 ... 

S Takahashi, T Kuzuyama, H Watanabe, H Seto. A 1-deoxy-D-xylulose 5-phos-phate reductoisomerase catalyzing the formation of 2-C-methyl-D-erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis. Proc Natl Acad Sci (USA) 95 9879-9884, 1998. 

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