Chapter nine Engineering pathway enzymes to understand the function and evolution of sterol structure and activity

Recent Advances in Phytochemistry

Volumn 40, Issue C, 2006, Pages 211-251

  Jayasimha, Pruthvi ^a   Bowman, C Bryson ^a   Pedroza, Julia M ^a   Nes, W David ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957074519     PISSN: 00799920     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0079-9920(06)80043-2     Document Type: Chapter

References (86)

1. Guo D., Venkatramesh M., and Nes W.D. Developmental regulation of sterol biosynthesis in Zeamays 30 (1995) 203-213
2. Akihisa T., Kokke W.C.M.C., and Tamura T. Naturally occurring sterols and related compounds from plants. In: Patterson G.W., and Nés W.D. (Eds). Physiology and Biochemistry of Sterols (1991), Amer. Oil Chem. Soc. Press, Champaign 172-228
3. 2425 -sterol methyltransferase. J. Biol Chem. 266 (1991) 15202-15212
4. Silva C.J., Giner J.-L., and Djerassi C. Biosynthetic studies of marine lipids. Enzymatic desaturation of 24(S)-methylcholesterol to 23,24-methlenecholesterol, norficasterol andnorhebeesterol. Further evidence for a unified biosynthesis of marine sterols with unique side chains. J. Amer. Chem. Soc. 114 (1992) 295-299
5. 680p. Nes W.R., and Mckean M.L. Biochemistry of Steroids and Other Isopentenoids (1977), University Park Press, Baltimore
6. Nes W.D., Song Z., Dennis A.I., Zhou W., Nam J., and Miller M.M. Biosynthesis of phytosterols. Kinetic mechanism for the enzymatic C-methylation of sterols. J. Biol. Chem. 278 (2003) 34505-34516
7. Nes W.D. Sterol methyltransferase: Enzymology and inhibition. Biochim. Biophys. Acta. 1529 (2000) 63-88
8. Benveniste P. Biosynthesis and accumulation of sterols. Annu. Rev. Plant. Biol. 55 (2004) 429-457
9. Roberts C.W., Mcleod R., Rice D.W., Ginger M., Chance M.L., and Goad L.J. Fatty acid and sterol metabolism: Potential antimicrobial targets in apicomplexan and trypanosomatid parasititc protozoa. Mole. Biochem. Parasit. 126 (2003) 129-142
10. Nes W.D. Enzymatic mechanisms for sterol C-methylations. Phytochemistry 64 (2003) 75-95
11. Nes W.D., Norton R.A., Crumley F.G., Madigan S.J., and Katz E.R. Sterol phylogenesis and algal evolution. Proc. Natl Acad. Sci. USA. 87 (1990) 7565-7569
12. 244 p. Nes W.R., and Nes W.D. Lipids in Evolution (1980), Plenum Press, New York
13. Nes W.R. Role of sterols in membranes. Lipids 9 (1974) 596-612
14. Poralla K., and Kannenber E. Hopanoids: sterol equivalents in bacteria. ACS Symp. Ser. 325 (1987) 239-251
15. Ourisson G., Rohmer M., and Anton R. From Terpenes to sterols: Macroevolution and microevolution. Rec. Adv. Phytochem. 13 (1978) 131-162
16. Bode H.B., Zeggel B., Silakowski B., Wenzel S.C., Reichenbach H., and Muller R. Steroid biosynthesis in prokaryotes: Identification of myxobacterial steroids and cloning of the first bacterial 2,3(S)-oxidosqualene cyclasefrom the myxobacterium Stigmatella aurantiaca. Mole. Microbiol. 47 (2003) 471-481
17. Pearson A., Budin M., and Brocks J.J. Phylogenetic and biochemical evidence for sterol synthesis in the Gemmata obscuriglobus. Proc. Natl. Acad. Sci. USA 100 (2003) 15352-15357
18. Bellamine A., Mangla A.T., Nes W.D., and Waterman M.R. Characterization and catalytic properties of the sterol 14α-demthylase from Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. USA 96 (1999) 8937-8942
19. Wendt K.U., Schulz G.E., Corey E.J., and Liu D.R. Enzyme mechanisms for polycylic triterpene formation. Agnew. Chem. Int. Ed. 39 (2000) 2812-2833
20. Rychnovsky S.D., and Mickus D.E. Synthesis of ent-cholesterol, the unnatural enantiomer. J. Org. Chem. 57 (1992) 2732-2736
21. Nes W.D., and Venkatramesh M. Molecular asymmetry and sterol evolution. ACS Symp. Ser. 562 (1994) 57-89
22. 5 -C26-sterol. Chem. Commun. (1981) 367-368
23. Zhou, W., Lepesheva., G. I., Waterman, M. R., Nes., W.D., Mechanistic analysis of a multiple product sterol methyltransferase implicated inergosterol biosynthesis in Trypanosoma brucei, J. Biol. Chem., in press.
24. Rahier A., Genot J.-C., Benveniste P., and Narula A.S. Inhibition of S- adenosyl-L-methionine sterol C-24 methyltransferase by analogues of a carbocationic high energy intermediate. J. Biol Chem. 259 (1984) 15213-15215
25. Goodwin T.W. Biosynthesis of plant sterols and other triterpenoids. In: Porter J.W., and Spurgeon S.L. (Eds). Biosynthesis of Isoprenoid Compounds Vol. 1 (1980), Wiley and Sons, New York 444-480
26. Behmer S.T., and Nes W.D. Insect sterol nutrition and physiology: A global overview. Adv. Insect Physiol. 31 (2003) 1-72
27. Nes W.D. Biosynthesis and requirement for sterols in the growth and reproduction of Oomycetes. ACS Symp. Ser. 325 (1987) 304-328
28. Pinto W.J., Lozano R., and Nes W.R. Inhibition of sterol biosynthesis by ergosterol and cholesterol in Saccharomyces cerevisiae. Biochim. Biophys. Acta 836 (1985) 89-95
29. Nes W.R., Sekula B.C., Nes W.D., and Adler J.H. The functional importance of structural features of ergosterol in yeast. J. Biol Chem. 253 (1978) 6218-6225
30. Rodriquez R.J., Low C., Bottema C.D.K., and Parks L.W. Multiple functions for sterols in Saccharomyces cerevisiae. Biochim. Biophys. Acta 837 (1985) 336-343
31. Buttke T.M., and Bloch K. Utilization and metabolism of methyl-sterol derivatives in the yeast mutant strain GL7. Biochemistry 20 (1981) 3267-3272
32. Nes W.D., Janssen G.G., Crumley F.G., Kalinowska M., and Akihisa T. The structural requirement of sterols for membrane function in Saccharomyces cerevisiae. Arch. Biochem. Biophys. 300 (1993) 724-733
33. Nes W.D., and Heupel R.C. Physiological requirement for biosynthesis of multiple 24β-methyl sterols in Gibberella fujikuroi. Arch. Biochem. Biophys. 244 (1986) 211-217
34. Pinto W.J., and Nes W.R. Stereochemical specificity for sterols in Saccharomyces cerevisiae. J. Biol. Chem. 258 (1983) 4472-4476
35. Schüler I., Milon A., Nakatani Y., Ourisson G., Albrecht A.-M., Benveniste P., and Hartman M.-A. Differential effects of plants sterols on water permeability and on acyl lipid chain ordering of soybean phosphatidylcholine bilayers. Proc. Natl. Acad. Sci. USA 88 (1991) 6926-6930
36. Bitmann R. Has nature designed the cholesterol side chain for optimal interaction with phospholipids. Subcell. Biochem. 28 (1997) 145-171
37. Demel R.A., and Dekruyff B. The function of sterols in membranes. Biochim. Biophys. Acta 457 (1976) 109-121
38. Herman G.E. X-Linked dominant disorders of cholesterol biosynthesis in man and mouse. Biochim. Biophys. Acta 1529 (2000) 357-373
39. Schaller H. New aspects of sterol biosynthesis in growth and development of higher plants. Plant Physiol Biochem. 42 (2004) 465-476
40. Clouse S.D. Arabidopsis mutants reveal multiple roles for sterols in plant development. The Plant Cell 14 (2002) 1995-2000
41. Nes W.D., Hanners P.K., and Parish E.J. Control of fungal sterol C-24 transalkylation: Importance of developmental regulation. Biochem. Biophys. Res. Comun. 139 (1986) 410-415
42. Porter J.A., Young K.E., and Beachy P.A. Cholesterol modification of hedgehog signaling proteins in animal development. Science 274 (1996) 255-259
43. Nes W.R. Structure-function relationships for sterols in Saccharomyces cerevisiae. ACS Symp. Ser. 325 (1987) 252-267
44. Xu F., Rychonovsky S.C., Belani J.D., Hobbs H.H., Cohen J.C., and Rawson R.B. Dual roles for cholesterol in mammalian cells. Proc. Natl. Acad. Sci. USA 102 (2005) 14551-14556
45. Whitaker B.D., and Nelson D.L. Growth and metabolism of phytosterols in Paramecium tetaurelia. Lipids 22 (1987) 386-396
46. Svoboda J.A., and Thompson M.J. Variability in steroid metabolism among phytophagous insects. ACS Sym. Ser. 325 (1987) 176-186
47. Li J., Nagpal P., Witart V., Mcmorris T.C., and Chory J. A role of brassinosteroids in light-dependent development of Arabidopsis. Science 272 (1996) 398-401
48. Nes W.D. Control of sterol biosynthesis and its importance to developmental regulation and evolution. Rec. Adv. Phytochem. 24 (1990) 283-327
49. Bloch K.E. Sterol structure and membrane function. CRC Crit. Rev. Biochem. 14 (1983) 47-82
50. Zhou W., and Nes W.D. Stereochemistry of hydrogen migration from C-24 to C-25 during biomethylation in ergosterol biosynthesis. Tetrahedron Letts. 37 (1996) 1339-1342
51. Westover E.J., Covey D.F., Brockman H.L., Brown R.E., and Pike L.J. Cholesterol depletion results in site-specific increases in epidermal growth factor receptor phosphorylation due to membrane level effects. J. Biol Chem. 278 (2003) 51125-51133
52. 13 C NMR, crystallographic observations, and molecular mechanics calculations. J. Am. Chem. Soc. 120 (1998) 5970-5980
53. 13 C NMR, crystallographic observations, and molecular mechanics calculations. J. Am. Chem. Soc. 14 (1998) 47-82
54. Nes W.D., Wong R.Y., Benson M., Landrey J.R., and Nes W.R. Rotational- isomerism about the 17(20)-bond of steroids and euphoids as shown by the crystal-structures of euphol and tirucallol. Proc. Natl. Acad. Sci. USA 81 (1984) 5896-5900
55. Bernsdorff C., and Winter R. Differential properties of the sterols cholesterol, ergosterolm β-sitosterol, trans-7-dehydrocholesterol, stigmasterol and lanosterol on DPPC bilayer order. J. Phys. Chem. 107 (2003) 10658-10664
56. Parks L.W., Crowley J.H., Leak F.W., Smith S.J., and Tomeo M.E. Use of sterol mutants as probes for sterol functions in the yeast, Saccharomyces cerevisiae. In: Parish E.J., and Nes W.D. (Eds). Biochemistry and Function of Sterols (1997), CRC, Boca Raton 257-262
57. Nes W.D., and Le P.H. Evidence for separate intermediates in the biosynthesis of 24β-methylsterol end products by Gibberella fujikuroi. Biochim. Biophys. Acta 1042 (1990) 11-125
58. Mangla A.T., and Nes W.D. Sterol C-methyl transferase from Prototheca wickerhamii: Mechanism, sterol specificity, and inhibition. Bioorg. Med. Chem. 8 (2000) 925-936
59. Kanagasabai R., Zhou W., Liu J., Nguyen T.T.M., Veeramachaneni P., and Nes W.D. Disruption of ergosterol biosynthesis, growth, and the morphological transition in Candida albicans by sterol methyltransferase inhibitorscontaining sulfur at C-25 in the sterol side chain. Lipids 39 (2004) 737-746
60. Zhou W., and Nes W.D. Sterol methyltransferase2: purification, properties and inhibition. Arch Biochem. Biophys. 420 (2003) 18-34
61. 2428 -sterolmethyltransferase from Saccharomyces cerevisiae. Arch. Biochem. Biophys. 353 (1998) 297-311
62. Nes W.D., Song Z., Dennis A.L., Zhou W., and Nam J. Biosynthesis of phytosterols. Kinetic mechanism for the enzymatic C-methylation of sterols. J. Biol. Chem. 278 (2003) 34505-34516
63. Diener A.C., Li H., Whoriskey W.J., Nes W.D., and Fink G.R. Sterol methyltransferase 1 controls the level of cholesterol in plants. The Plant Cell 12 (2000) 853-870
64. Bouvier-Nave P., Husselstein T., and Benveniste P. Two families of sterol methyltransferases are involved in the first and second methylation steps of plant sterol biosynthesis. Eur. J. Biochem. 256 (1998) 88-96
65. 2425 - sterol methyltransferase from Saccharomyces cerevisiae. Biochim. Biophys. Acta 1299 (1996) 313-324
66. Parker S.R., and Nes W.D. Regulation of sterol biosynthesis and phylogenetic implications. ACS Symp. Ser. 497 (1994) 110-145
67. Arigoni D. Stereochemical studies of enzymic C-methylations. Ciba Found. Symp. 60 (1978) 243-258
68. Nes W.D., Jayasimha P., Zhou W., Kanagasabai R., and Jin C. Jaradat, T. T., Shaw, R. W., Bujnicki, J. M., Sterol methyltransferase. Functional analysis of highly conserved residues by site-directed mutagenesis. Biochemistry 43 (2004) 569-576
69. Koshland D., and Neet K.E. The catalytic and regulatory properties of enzymes. Annu. Rev. Biochem. 37 (1968) 359-410
70. Jayasimha, P., Song, Z., Nes, W.D., Biochemistry, in press.
71. Hardwick K.G., and Pelham H.R.B. SED6 is identical to ERG6 and encodes a putative methyltransferase required for ergosterol biosynthesis. Yeast 10 (1994) 265-269
72. Venkatrmesh M., Guo D., Harman J.G., and Nes W.D. Sterol specificity of the Saccharomyces cerevisiae ERG6 gene product expressed in Escherichia coli. Lipids 31 (1996) 373-377
73. Schubert H.L., Blumenthal R.M., and Cheng X. Many paths to methyltransferase: a chronicle of convergence. Trend Biochem. Sci. 28 (2003) 329-336
74. Kagan R.M., and Clarke S. Widespread occurrence of three sequence motifs in diverse S-adenosyl-L-methionine-dependent methyltransferases suggests a common structure for these enzymes. Arch. Biochem. Biophys. 310 (1994) 417-427
75. Nes W.D., Marshall J.A., Jia Z., Jaradat T.T., Song Z., and Jayasimha P. Active site mapping and substrate channeling in the sterol methyltransferase pathway. J. Biol Chem. 277 (2002) 42549-42556
76. Nes W.D., Mc Court B.S., Marshall J.A., Ma J., Dennis A.L., Lopez M., Li H., and He L. Site-directed mutagenesis of the sterol methyltransferase active site from Saccharomyces cerevisiae results in formation of novel 24-ethyl sterols. J. Org. Chem. 64 (1999) 1535-1542
77. in press. Nes W.D., Sinha A., Jayasimha P., Zhou W., Song Z., and Dennis A.L. Probing the sterol binding site of soybean sterol methyltransferase by site-directed mutagenesis: Functional analysis of conserved aromatic amino acids in Reg. Arch Biochem. Biophys. (2005)
78. Guo D., Jia Z., and Nes W.D. Phytosterol biosynthesis. Isotope effects associated with biomethylation formation in 24-alkene sterol isomers. Tetrahedron Letts. 37 (1996) 6823-6826
79. Fonteneau P., Hartmann M.A., and Benveiste P. A 24-Methylene lophenol C-28 methyltransferase from suspension cultures of bramble cells. Plant Sci. Lett. 10 (1977) 147-155
80. Misso N.L.A., and Goad L.J. The synthesis of 24-methylene cycloartanol, cyclosadol, and cyclolaudenol by a cell free preparation from Zea mays shoots. Phytochemistry 22 (1983) 2473-2476
81. Nes W.D. Enzyme redesign and interactions of substrate analogues with sterol methyltransferase to understand phytosterol diversity, reaction mechanism and the nature o. Biochem. Soc. Trans. 33 (2005) 1189-1196
82. 1 -methyltransferase in tobacco modifies the ratio of 24-methyl cholesterol tositosterol and is associated with growth reduction. Plant Physiol. 118 (2001) 461-469
83. Jencks W.P. Binding energy, specificity, and enzymic catalysis: the Circe effect. Adv. Enzymol. 43 (1975) 210-410
84. Albery W.J., and Knowles J.R. Evolution of enzyme function and the development of catalytic efficiency. Biochemistry 15 (1976) 5631-5640
85. Brocks J.J., Logan G.A., and Buick R. Archean molecular fossils and the early rise of eukaryotes. Science 285 (1999) 1033-1036
86. Zhou, W., Nguyen, H.T., Nes, W.D., Plant sterol methyltransferases: Phytosterolomic analysis, enzymology and bioengineering strategies.In: Advances in Plant Biochemistry and Molecular Biology (Lewis, N.G. ed.), Vol. 1, Bioengineering and Molecular Biology of Plant Pathways (Bohnert, H. J. and Nguyen, H. T., eds,), Elsevier Science, Oxford. In press.