A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescens

Phytochemistry

Volumn 71, Issue 4, 2010, Pages 373-379

  Mau, Christopher J D ^a   Karp, Frank ^a   Ito, Michiho ^b   Honda, Gisho ^b   Croteau, Rodney B ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

( ) Limonene 7 hydroxylase; Cytochrome P450; Lamiaceae; Monoterpenoid; Perilla frutescens; Perillaldehyde; Perillyl alcohol

Indexed keywords

COMPLEMENTARY DNA; CYTOCHROME P450;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; CYTOLOGY; ENZYMOLOGY; ESCHERICHIA COLI; GENE LIBRARY; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR CLONING; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; PERILLA FRUTESCENS; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; CLONING, MOLECULAR; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; ESCHERICHIA COLI; GENE LIBRARY; MOLECULAR SEQUENCE DATA; PERILLA FRUTESCENS; SEQUENCE HOMOLOGY, AMINO ACID;

ESCHERICHIA COLI; LAMIACEAE; MAGNOLIOPHYTA; MENTHA SPICATA; MENTHA X PIPERITA; PERILLA; PERILLA FRUTESCENS;

EID: 76249085623     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.12.002     Document Type: Article

References (44)

1. Ausubel, F.M., Brent, R., Kingston, R.E., Moore, D.D., Seidman, J.G., Smith, J.A., Struhl, K., 1991. Current Protocols in Molecular Biology. Greene Publishing Associates and Wiley-Interscience, New York, pp. 6.3.1-6.3.2.
2. Bak S., and Feyereisen R. The involvement of two P450 enzymes, CYP83B1 and CYP83A1, in auxin homeostasis and glucosinolate biosynthesis. Plant Physiol. 127 (2001) 108-118
3. Barnes H.J. Maximizing expression of eukaryotic cytochrome P450s in Escherichia coli. Meth. Enzymol. 272 (1996) 3-14
4. Barnes H.J., Arlotto M.P., and Waterman M.R. Expression and enzymatic activity of recombinant cytochrome P450 17α-hydroxylase in Escherichia coli. Proc. Natl. Acad. Sci. USA 88 (1991) 5597-5601
5. Bertea C., Schalk M., Mau C.J.D., Karp F., Wildung M.R., and Croteau R. Molecular evaluation of a spearmint mutant altered in the expression of limonene hydroxylases that direct essential oil monoterpene biosynthesis. Phytochemistry 64 (2003) 1203-1211
6. Bozak K.R., Yu H., Sirevag R., and Christoffersen R.E. Sequence analysis of ripening-related cytochrome P-450 cDNAs from avocado fruit. Proc. Natl. Acad. Sci. USA 87 (1990) 3904-3908
7. Buckingham J. Dictionary of Natural Products Web Version (2004), Chapman and Hall, London
8. Chang M.C.Y., Eachus R.A., Trieu W., Ro D.-K., and Keasling J.D. Engineering Escherichia coli for production of functionalized terpenoids using plant P450s. Nat. Chem. Biol. 3 (2007) 274-277
9. Clark I.M., Forde B.G., and Hallahan D.L. Spatially distinct expression of two new cytochrome P450s in leaves of Nepeta racemosa: identification of a trichome-specific isoform. Plant Mol. Biol. 33 (1997) 875-885
10. Croteau R., Karp F., Wagschal K.C., Satterwhite D.M., Hyatt D.C., and Skotland C.B. Biochemical characterization of a spearmint mutant that resembles peppermint in monoterpene content. Plant Physiol. 96 (1991) 744-752
11. Croteau R., Davis E.M., Ringer K.L., and Wildung M.R. Menthol biosynthesis and molecular genetics. Naturwissenschaften 92 (2005) 562-577
12. Dudareva N., Pichersky E., and Gershenzon J. Biochemistry of plant volatiles. Plant Physiol. 135 (2004) 1893-1902
13. Duetz W.A., Bouwmeester H.J., van Beilen J.B., and Witholt B. Biotransformation of limonene by bacteria, fungi, yeasts, and plants. Appl. Microbiol. Biotechnol. 61 (2003) 269-277
14. Fahn A. Secretory Tissues in Plants (1979), Academic Press Inc. Ltd., London
15. Fischer T.C., Klattig J.T., and Gierl A. A general cloning strategy for divergent plant cytochrome P450 genes and its application in Lolium rigidum and Ocimum basilicum. Theor. Appl. Genet. 103 (2001) 1014-1021
16. Frohman M.A., Dush M.K., and Martin G.R. Rapid production of full-length cDNAs from rare transcripts: amplification using a single gene-specific oligonucleotide primer. Proc. Natl. Acad. Sci. USA 85 (1988) 8998-9002
17. Gang D.R., Wang J., Dudareva N., Nam K.H., Simon J.E., Lewinsohn E., and Pichersky E. An investigation of the storage and biosynthesis of phenylpropenes in sweet basil. Plant Physiol. 125 (2001) 539-555
18. Gershenzon J., McCaskill D., Rajaonarivony J.I.M., Mihaliak C., Karp F., and Croteau R. Isolation of secretory cells from plant glandular trichomes and their use in biosynthetic studies of monoterpenes and other gland products. Anal. Biochem. 200 (1992) 130-138
19. Gubler U., and Hoffman M.J. A simple and very efficient method for generating cDNA libraries. Gene 25 (1983) 263-269
20. Guenther E. The Essential Oils (1950), D. Van Nostrand Company Inc., New York
21. Halkier B.A., Nielsen H.L., Koch B., and Moller B.L. Purification and characterization of recombinant cytochrome P450TYR expressed at high levels in Escherichia coli. Arch. Biochem. Biophys. 322 (1995) 369-377
22. Hallahan D.L. Monoterpenoid biosynthesis in glandular trichomes of Labiate plants. Adv. Bot. Res. 31 (2000) 77-120
23. Hallahan D.L., and West J.M. Cytochrome P-450 in plant/insect interactions: geraniol 10-hydroxylase and the biosynthesis of iridoid monoterpenoids. Drug Metab. Drug Interact. 12 (1996) 369-382
24. Haudenschild C., Schalk M., Karp F., and Croteau R. Functional expression of regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha spp.) in Escherichia coli and Saccharomyces cerevisiae. Arch. Biochem. Biophys. 379 (2000) 127-136
25. Horner, C.E., Melouk, H.A., 1977. Screening, selection and evaluation of irradiation induced mutants of spearmint for resistance to Verticillium wilt. In: International Atomic Energy Agency, Induced Mutations Against Plant Diseases, Vienna, pp. 253-262.
26. Horton R.M., Hunt H.D., Ho S.N., Pullen J.K., and Pease L.R. Engineering hybrid genes without the use of restriction enzymes: gene splicing by overlap extension. Gene 77 (1989) 61-68
27. Ito M., Toyoda M., and Honda G. Chemical composition of the essential oil of Perilla frutescens. Nat. Med. 53 (1999) 32-36
28. Jennewein S., Long R.M., Williams R.M., and Croteau R. Cytochrome P450 taxadiene 5α-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis. Chem. Biol. 11 (2004) 379-387
29. Karp F., and Croteau R. Hydroxylation of (-)-β-pinene and (-)-α-pinene by a cytochrome P450 system from hyssop (Hyssopus officinalis). In: Petroski R.J., and McCormick S.P. (Eds). Secondary Metabolite Biosynthesis and Metabolism (1992), Plenum Press, New York 253-260
30. Karp F., Mihaliak C.A., Harris J.L., and Croteau R. 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. 276 (1990) 219-226
31. Lange B.M., Wildung M.R., Stauber E.J., Sanchez C., Pouchnik D., and Croteau R. Probing essential oil biosynthesis and secretion by functional evaluation of expressed sequence tags from mint glandular trichomes. Proc. Natl. Acad. Sci. USA 97 (2000) 2934-2939
32. Logemann J., Schell J., and Willmitzer L. Improved method for the isolation of RNA from plant tissues. Anal. Biochem. 163 (1987) 16-20
33. Lupien S., Karp F., Wildung M., and Croteau R. 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. Arch. Biochem. Biophys. 368 (1999) 181-192
34. Mau C.J.D., and Croteau R. Cytochrome P450 oxygenases of monoterpene metabolism. Phytochem. Rev. 5 (2006) 373-383
35. Meijer A.H., Souer E., Verpoorte R., and Hoge J.H.C. Isolation of cytochrome P-450 cDNA clones from the higher plant Catharanthus roseus by a PCR strategy. Plant Mol. Biol. 22 (1993) 379-383
36. Mihaliak C., Karp F., and Croteau R. Cytochrome P-450 terpene hydroxylases. In: Lea P.J. (Ed). Methods in Plant Biochemistry (Enzymes of Secondary Metabolism) vol. 9 (1993), Academic Press, London 261-279
37. Nishizawa A., Honda G., Kobayashi Y., and Tabata M. Genetic control of peltate glandular trichome formation in Perilla frutescens. Planta Medica 58 (1992) 188-191
38. Nishizawa A., Honda G., and Tabata M. Genetic control of the enzymatic formation of cyclic monoterpenoids in Perilla frutescens. Phytochemistry 31 (1992) 139-142
39. O'Brien M., Chantha S.-C., Rahier A., and Matton D.P. Lipid signaling in plants. Cloning and expression analysis of the obtusifoliol 14α-demethylase from Solanum chacoense Bitt., a pollination- and fertilization-induced gene with both obtusifoliol and lanosterol demethylase activity. Plant Physiol. 139 (2005) 734-749
40. Omura T., and Sato R. The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239 (1964) 2370-2378
41. Schalk M., and Croteau R. A single amino acid substitution (F363I) converts the regiochemistry of the spearmint (-)-limonene hydroxylase from a C6- to a C3-hydroxylase. Proc. Natl. Acad. Sci. USA 97 (2000) 11948-11953
42. Wust M., and Croteau R. Hydroxylation of specifically deuterated limonene enantiomers by cytochrome P450 limonene-6-hydroxylase reveals the mechanism of multiple product formation. Biochemistry 41 (2002) 1820-1827
43. Wust M., Little D.B., Schalk M., and Croteau R. Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from mint (Mentha) species: evidence for catalysis within sterically constrained active sites. Arch. Biochem. Biophys. 387 (2001) 125-136
44. Yuba A., Yazaki K., Tabata M., Honda G., and Croteau R. CDNA cloning, characterization and functional expression of 4S-(-)-limonene synthase from Perilla frutescens. Arch. Biochem. Biophys. 332 (1996) 280-287