Regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha) species: cDNA isolation, characterization, and functional expression of (-)- 4S-limonene-3-hydroxylase and (-)-4S-limonene-6- hydroxylase

Archives of Biochemistry and Biophysics

Volumn 368, Issue 1, 1999, Pages 181-192

  Lupien, Shari ^a   Karp, Frank ^a   Wildung, Mark ^a   Croteau, Rodney ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

( ) trans carveol; ( ) limonene hydroxylase; ( ) trans isopiperitenol; Cytochrome P450 monooxygenase; Mentha spicata; Mentha x piperita; Monoterpene biosynthesis

Indexed keywords

CARVEOL; CYTOCHROME P450; LIMONENE; OXYGENASE; PEPPERMINT; TERPENE;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; BACULOVIRUS; BINDING AFFINITY; CALCULATION; CATALYSIS; ENZYME ACTIVITY; HYDROXYLATION; NUCLEOTIDE SEQUENCE; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL;

MENTHA;

EID: 0033179201     PISSN: 00039861     EISSN: None     Source Type: Journal    
DOI: 10.1006/abbi.1999.1298     Document Type: Article

References (85)

1. Harborne J. B. Harborne J. B., Tomas-Barberan F. A. Ecological Chemistry and Biochemistry of Plant Terpenoids. 1991;396-426 Clarendon Press, Oxford.
2. Buckingham, J. 1998, Dictionary of Natural Products on CD-ROM, Version 6.1, Chapman and Hall, London, UK.
3. West C. A. Davies D. D. The Biochemistry of Plants. 1980;2-364 Academic Press, New York.
4. Karp F., Croteau R. Schreier P. Bioflavor '87: Analysis, Biochemistry, Biotechnology. 1988;173-198 de Gruyter, Berlin.
5. Mihaliak C. A., Karp F., Croteau R. Methods Plant Biochem. 9:1993;261-279.
6. Lawrence B. M. Mookherjee B. D., Mussinan C. J. Essential Oils. 1981;1-81 Allured Publ. Co. Wheaton.
7. Harley R. M., Brighton C. A. Bot. J. Linn. Soc. 74:1977;71-96.
8. Murray M. J., Lincoln D. E., Marble P. M. Can. J. Genet. Cytol. 14:1972;13-29.
9. Halkier B. A. Phytochemistry. 54:1996;1-21.
10. Karp F., Mihaliak C. A., Harris J. L., Croteau R. Arch. Biochem. Biophys. 276:1990;219-226.
11. Bolwell G. P., Bozak K., Zimmerlin A. Phytochemistry. 37:1994;1491-1506.
12. Croteau R., Karp F., Wagschal K. C., Satterwhite D. M., Hyatt D. C., Skotland C. B. Plant Physiol. 96:1991;744-753.
13. McCaskill D., Croteau R. Adv. Biochem. Eng. Biotechnol. 55:1997;102-146.
14. Haudenschild C. D., Croteau R. B. Setlow J. K. Genetic Engineering: Principles and Methods. 1998;267-280 Plenum, New York.
15. Alonso W. R., Rajaonarivony J. I. M., Gershenzon J., Croteau R. J. Biol. Chem. 267:1992;7582-7587.
16. Kjonaas R. B., Venkatachalam K. V., Croteau R. Arch. Biochem. Biophys. 238:1985;49-60.
17. Croteau R., Venkatachalam K. V. Arch. Biochem. Biophys. 249:1986;306-315.
18. Gershenzon J., McCaskill D., Rajaonarivony J. I. M., Mihaliak C., Karp F., Croteau R. Recent Adv. Phytochem. 25:1991;347-370.
19. Gershenzon J., McCaskill D., Rajaonarivony J. I. M., Mihaliak C., Karp F., Croteau R. Anal. Biochem. 200:1992;130-138.
20. Lupien S., Karp F., Ponnamperuma K., Wildung M., Croteau R. Drug Metab. Drug Interact. 12:1995;245-260.
21. Omura T., Sato R. J. Biol. Chem. 239:1964;2379-2385.
22. Laemmli U. K. Nature. 227:1970;680-685.
23. White R. E., Coon M. J. Annu. Rev. Biochem. 49:1980;315-356.
24. Ortiz de Montellano P. R. Ortiz de Montellano P. R. Cytochrome P450, Structure, Mechanism and Biochemistry. 1986;217-271 Plenum, New York.
25. Bradford M. M. Anal. Biochem. 72:1976;248-254.
26. Wray W., Boulikas T., Wray V. P., Hancock R. Anal. Biochem. 118:1981;197-203.
27. O'Keefe D. P., Leto K. J. Plant Physiol. 89:1989;1141-1149.
28. Ponnamperuma K., Croteau R. Arch. Biochem. Biophys. 329:1995;9-16.
29. Shet M. S., Sathasivan K., Arlotto M. A., Mehdy M. C., Estabrook R. W. Proc. Natl. Acad. Sci. USA. 90:1993;2890-2894.
30. Kjonaas R., Croteau R. Arch. Biochem. Biophys. 220:1983;79-89.
31. Colby S. M., Alonso W. R., Katahira E., McGarvey D. J., Croteau R. J. Biol. Chem. 268:1993;23016-23024.
32. O'Keefe D. P. Pell E. J., Steffen K. L. Active Oxygen/Oxidative Stress and Plant Metabolism. 1991;204-213 American Society of Plant Physiologists, Rockville.
33. Hillam R. P., Tengerdy R. P., Brown G. L. Infect. Immun. 10:1974;458-463.
34. Reid J. L., Everard J. D., Diani J., Walker-Simmons M. K. Biotechniques. 12:1992;660-666.
35. Alonso W. R., Crock J. E., Croteau R. Arch. Biochem. Biophys. 301:1993;58-63.
36. Schagger H., von Jagow G. Anal. Biochem. 166:1987;368-379.
37. Hunkapiller M. Methods Enzymol. 91:1991;227-235.
38. Cleveland D. W., Fischer S. G., Kirschner M. W., Laemmli U. K. J. Biol. Chem. 252:1977;1102-1106.
39. Towbin H., Staehelin T., Gordon J. Proc. Natl. Acad. Sci. USA. 76:1979;4350-4354.
40. Innis M. A., Gelfand D. H. Innis M. A., Gelfand D. H., Sninsky J. J., White T. J. PCR Protocols. 1990;3-12 Academic Press, San Diego.
41. Tabor S., Struhl K., Scharf S. J., Gelfand D. H. Ausubel R. M., Brent R., Kingston R. E., Moore D. D., Seidman J. G., Smith J. A., Struhl K. Current Protocols in Molecular Biology. 1991;Wiley, New York.
42. Titus D. E. Promega Protocols and Applications Guide. 1991;Promega, Madison.
43. Gonzalez R. G., Haxo R. S., Schleich T. Biochemistry. 19:1980;4299-4303.
44. Van Driessche E., Beeckmans S., Dejaegere R., Kanarek L. Anal. Biochem. 141:1984;184-188.
45. Logemann J., Schell J., Willmitzer L. Anal. Biochem. 163:1987;16-20.
46. Lewinsohn E., Steele C. L., Croteau R. Plant Mol. Biol. Rep. 12:1994;20-25.
47. Rhodes, D. D, and, Roufa, D. J. 1991, SEQAIDII is a public domain program provided by the authors, Kansas State University, Manhattan, KS.
48. Genetics Computer Group, 1996, Wisconsin Package Version 9.0, Genetics Computer Group (GCG), Madison, WI.
49. Summers M. D., Smith G. E. A Manual of Methods for Baculovirus Vectors and Insect Cell Culture Procedures. 1988;Texas Agricultural Experiment Station, College Station. p. 1555.
50. O'Reilly D. R., Miller L. K., Lucknow V. A. Baculovirus Expression Vectors, A Laboratory Manual. 1994;Oxford Univ. Press, Oxford.
51. Smith C. A. D., Gough A. C., Leigh P. N., Summers B. A., Harding A. E., Maraganore D. M., Sturman S. G., Schapira A. H. V., Williams A. C., Spurr N. K., Wolf C. R. Lancet. 339:1992;1375-1377.
52. Schuler M. A. CRC Crit. Rev. Plant Sci. 15:1996;235-284.
53. Chapple C. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49:1998;311-343.
54. Gershenzon J., Maffei M., Croteau R. Plant Physiol. 89:1989;1351-1357.
55. McCaskill D., Gershenzon J., Croteau R. Planta. 187:1992;445-454.
56. Gershenzon J., Duffy M. A., Karp F., Croteau R. Anal. Biochem. 163:1987;159-164.
57. Madyastha K. M., Meehan T. D., Coscia C. J. Biochemistry. 15:1976;1097-1102.
58. Benveniste I., Salaun J. P., Durst F. Phytochemistry. 16:1977;69-73.
59. Salaun J. P., Benveniste I., Reichart D., Durst F. Eur. J. Biochem. 119:1981;651-655.
60. Petersen M. Z. Naturforsch. 43C:1991;199-206.
61. Taton M., Rahier A. Biochem. J. 276:1991;483-492.
62. Stadler R., Zenk M. H. J. Biol. Chem. 268:1993;823-831.
63. Funk C., Croteau R. Plant Physiol. 101:1993;1231-1237.
64. Yamano T., Ichikawa Y. Pharmacol. Ther. (Part A). 2:1978;673-692.
65. Jefcoate C. R. Methods Enzymol. 52:1978;258-279.
66. Yun C.-H., Song M., Ahn T., Kim H. J. Biol. Chem. 271:1996;31312-31316.
67. Yun C.-H., Song M., Kim H. J. Biol. Chem. 272:1997;19725-19730.
68. Bozak K. R., Yu H., Sirevag R., Christoffersen R. E. Proc. Natl. Acad. Sci. USA. 87:1990;3904-3908.
69. Kutchan T. M., Bock A., Dittrich H. Phytochemistry. 35:1994;353-360.
70. Barnes H. J., Jenkins C. M., Waterman M. R. Arch. Biochem. Biophys. 315:1994;489-494.
71. Gonzalez F. J., Korzekwa K. R. Annu. Rev. Pharmacol. Toxicol. 35:1995;369-390.
72. Brown C. A., Black S. D. J. Biol. Chem. 264:1989;4442-4449.
73. Nelson D. R., Strobel H. W. J. Biol. Chem. 263:1988;6038-6050.
74. Sakaguchi M., Mihara K., Sato R. EMBO J. 6:1987;2425-2431.
75. Shimada H., Sligar S. G., Yeom H., Ishimura Y. Funabiki T. Oxygenases and Model Systems. 1997;195-221 Kluwer, Boston.
76. von Wachenfeldt C., Johnson E. F. Ortiz de Montellano P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry. 1995;183-223 Plenum, New York.
77. Nelson D. R., Kamataki T., Waxman D. J., Guengerich F. P., Estabrook R. W., Feyereisen R., Gonzalez F. J., Coon M. J., Gunsalus I. C., Gotoh O., Okuda K., Nebert D. W. DNA Cell Biol. 12:1993;1-51.
78. Nelson D. R., Koymans L., Kamataki T., Stegeman J. J., Feyereisen R., Waxman D. J., Waterman M. R., Gotoh O., Coon M. J., Estabrook R. W., Gunsalus I. C., Nebert D. W. Pharmacogenetics. 6:1996;1-42.
79. Hutvagner G., Barta E., Banfalvi Z. Gene. 188:1997;247-252.
80. Gotoh O. J. Biol. Chem. 267:1992;83-90.
81. Urban P., Werck-Reichhart D., Teutsch H. G., Durst F., Regnier S., Kazmaier M., Pompon D. Eur. J. Biochem. 222:1994;843-850.
82. Fahrendorf T., Dixon R. A. Arch. Biochem. Biophys. 305:1993;509-515.
83. Lindberg R. L. P., Negishi M. Nature. 339:1989;632-634.
84. Niu X., Lin K., Hasegawa P. M., Bressan R. A., Weller S. C. Plant Cell Rep. 17:1998;165-171.
85. Diemer F., Jullien F., Faure O., Moja S., Colson M., Mattys-Rochon E., Caissard J. C. Plant Sci. 138:1998;101-108.