Chemistry: molecular biology and microbiology – Enzyme – proenzyme; compositions thereof; process for... – Oxidoreductase
Patent
1997-06-24
2000-07-04
Patterson, Jr., Charles L.
Chemistry: molecular biology and microbiology
Enzyme , proenzyme; compositions thereof; process for...
Oxidoreductase
4352523, 4353201, 536 232, C12N 902, C12N 1553
Patent
active
060837314
ABSTRACT:
cDNA encoding (-)-limonene-6-hydroxylase from spearmint and (-)-limonene-3-hydroxylase from peppermint have been isolated and sequenced, and the corresponding amino acid sequences have been determined. Accordingly, isolated DNA sequences are provided which code for the expression of (-)-limonene-6-hydroxylase from spearmint (SEQ ID No:1, from Mentha spicata) and (-)-limonene-3-hydroxylase from peppermint (SEQ ID No:8, from Mentha piperita). In other aspects, replicable recombinant cloning vehicles are provided which code for limonene hydroxylase or for a base sequence sufficiently complementary to at least a portion of the limonene hydroxylase DNA or RNA to enable hybridization therewith (e.g., antisense limonene hydroxylase RNA or fragments of complementary limonene hydroxylase DNA which are useful as polymerase chain reaction primers or as probes for limonene hydroxylase or related genes). In yet other aspects, modified host cells are provided that have been transformed, transfected, infected and/or injected with a recombinant cloning vehicle and/or DNA sequence encoding limonene hydroxylase. Thus, systems and methods are provided for the recombinant expression of limonene hydroxylase that may be used to facilitate the production, isolation and purification of significant quantities of recombinant limonene hydroxylase (or of the primary enzyme products, trans-carveol or trans-isopiperitenol, respectively) for subsequent use, to obtain expression or enhanced expression of limonene hydroxylase in plants to attain enhanced production of trans-carveol or trans-isopiperitenol as a predator or pathogen defense mechanism, or may be otherwise employed for the regulation or expression of limonene hydroxylase or the production of trans-carveol or trans-isopiperitenol.
REFERENCES:
Alberts et al., Molecular Biology of the Cell, Second Ed., Garland Publishing, Inc., New York, NY, pp. 185-187 and 265-266 (1989).
Alonso et al., "Production and Characterization of Polyclonal Antibodies in Rabbits to 4S(Limonene Synthase from Spearmint (Mentha spicata)," Arch. Biochem. Biophys. 301(1):58-63 (1993).
Alonso et al., "Purification of 4S-Limonene Synthase, a Monoterpene Cyclase from the Glandular Trichomes of Peppermint (Mentha x piperita) and Spearmint (Mentha spicata)" J. Biol. Chem. 267(11):7582-7587 (1992).
Alonso and Croteau, "Comparison of Two Monoterpene Cyclases Isolated From Higher Plants; .lambda.-Terpinene Synthase From Thymus Vulgaris, and Limonene Synthase From Mentha x Piperita," Secondary-Metabolite Biosynthesis and Metabolism (Petrosky and McCormick, eds.), Plenum Press, New York, NY, pp. 239-251 (1992).
Alonso and Croteau, "9. Prenyltransferases and Cyclases," Methods Plant Biochem. 9:239-260 (1993).
Ashby et al., in "Prenyltransferases: From Yeast to Man," Molecular Biology of Atherosclerosis (Attie, A.D., ed.), Elsevier Science Publishing Co., Inc., Amsterdam, pp. 27-34 (1990).
Bozak et al., "Sequence analysis of ripening-related cytochrome P-450 cDNAs from avocado fruit," Proc. Natl. Acad. Sci. USA 87:3904-3908 (1990).
Colby et al., 4S-Limonene Synthase from the Oil Glands of Spearmint (Mentha spicata), J. Biol. Chem. 268:23016-23024 (1993).
Colby et al., "Isolation and Characterization of cDNA Encoding Limonene Cyclase in Spearmint," J. Cell Biochem., Suppl. 0, 16(F):230 (1992), Abstract Only.
Croteau and Cane, "[44] Monoterpene and Sesquiterpene Cyclases," Methods of Enzymology 110:383-405 (1985).
Croteau, "Biosynthesis and Catabolism of Monterpenoids," Chem. Rev. 87:929-954 (1987).
Croteau and Satterwhite, "Biosynthesis of Monoterpenes," J. Biol. Chem. 264(26):15309-15315 (1989).
Croteau, "Metabolism of Plant Monterpenes," ISI Atlas of Science: Biochemistry, 1:182-188 (1988).
Croteau and Johnson, "7. Biosynthesis of Terpenoids in Glandular Trichomes," Biology and Chemistry of Plant Trichomes, Rodriguez et al., Eds., Plenum Publishing Corporation (1984), pp. 133-185.h.
Croteau and Gershenzon, "Chapter Eight. Genetic Control of Monoterpene Biosynthesis in Mints (Mentha: Lamiaceae)" Genetic Engineering of Plant Secondary Metabolism, B.E. Ellis et al., Eds., Plenum Press, New York (1994), pp. 193-229.
Croteau, "the Biosynthesis of Limonene in Mentha Species," In Progress in Flavour Precursor Studies (P. Schreier and P. Winterhalter, Eds.), Proceedings of the International of the International Conference, Allured Publishing Corporation, Carol Stream, Illinois, pp. 113-122 (1993).
Croteau, "Terpene Metabolism in Mint," Mint Industry Research Coucil, Washington Mint Commission, Technical Report Summary Statement, Jan. 22-24, 1997 (13 pages).
Croteau, "Metabolism of Monoterpenes in Mint (Mentha) Species," Planta Med. 57(S1);10-14 (1991).
Facchini and Chappell, "Gene family for an elicitor-induced sesquiterpene cyclase in tobacco," Proc. Natl. Acad. Sci. USA 89:11088-11092 (1992).
Gershenzon et al., "Isolation of Secretory Cells from Plant Glandular Trichomes and Their Use in Biosynthetic Studies of Monoterpenes and Other Gland Products," Anal. Biochem. 200:130-138 (1992).
Gershenzon et al., "Chapter Ten. Biosynthetic Methods for Plant Natural Products: New Procedures for the Study of Glandular Trichome Constituents," Modern Phytochemical Methods, N.H. Fischer et al., Eds., Plenum Press, New York (1991), pp. 347-370.
Gershenzon and Croteau, "Chapter 5. Terpenoids," Herbivores: Their Interactions with Secondary Plant Metabolites, vol. I, 2nd Ed. (Rosenthal and Berenbaum, eds.), Academic Press, San Diego, CA, pp. 165-219 (1991).
Gershenzon and Croteau, in "Chapter Three. Regulation of Monoterpene Biosynthesis in Higher Plants," Biochemistry of the Mevalonic Acid Pathway to Terpenoids (Towers, G.H.N. and Stafford, H.A., eds.), Plenum Press, New York, NY, Ch. 3, pp. 99-160 (1990).
Harborne, "16 Recent advances in the ecological chemistry of plant terpenoids," Ecological Chemistry and Biochemistry of Plant Terpenoids (Harborne and Tomas-Barberan, eds.), Clarendon Press, Oxford, MA, pp. 399-426 (1991).
Hallahan and Croteau, "Monoterpene Biosynthesis: Mechanism and Stereochemistry of the Enzymatic Cyclization of Geranyl Pyrophosphate to Cis-(+)-and (+)-trans-Sabinene Hydrate," Arch. Biochem. Biophys. 269(1):313-326 (1989).
Karp and Croteau, "Role of Hydroxylases in Monoterpene Biosynthesis," Bioflavour '87, Walter de Gruyter & Co., Berlin (1988), pp. 173-198.
Karp et al., "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. 276:219-226 (1990).
Karp and Croteau, "Hydroxylation of (-)-.beta.-Pinene and (-)-.alpha.-Pinene by a Cytochrome P-450 System from Hyssop (Hyssopus Officinalis)," Secondary-Metabolite Biosynthesis and Metabolism, R.J. Petroski et al., Eds., Plenum Press, New York (1992), pp. 253-260.
Kjonaas and Croteau, "Demonstration that Limonene is the First Cyclic Intermediate in Biosynthesis of Oxygenated p-Menthane Monoterpenes in Mentha piperita and Other Mentha Species," Arch. Biochem. Biophys. 220(1):79-89 (1983).
Lanznaster and Croteau, "Dye-Ligand and Immobilized Metal Ion Interaction Chromatography for the Purification of Enzymes of Prenyl Pyrophosphate Metabolism," Protein Express. Purif. 2:69-74 (1991).
Lupien et al., "Cytochrome P450 Limonene Hydroxylases of Mentha Species," Drug Metabolism and Drug Interactions, N. Kingsley, Ed., Freund Publishing House, London, England (1995), pp. 245-260.
Math et al., "The crtE gene in Erwinia herbicola encodes geranylgeranyl diphosphate synthase," Proc. Natl. Acad. Sci. USA 89:6761-6764 (1992).
McGarvey and Croteau, "Overexpression and mutagenesis of 4S-limonene synthase from spearmint (Mentha spicata)," Plant Physiology 105(1):89 (1994), Abstract Only.
Mihaliak et al., "10. Cytochrome P-450 Terpene Hydroxylases," Meth. Plant Biochem. 9:261-279 (1993).
Ponnamperuma and Croteau, "Purification and Characterization of an NADPH-Cytochrome P450 (Cytochrome c) Reductase from Spearmint (Mentha spicata) Glandular Trichomes," Arch. Biochem. Biophys. 329(1):9-16 (1996).
Croteau Rodney Bruce
Karp Frank
Lupien Shari Lee
Patterson Jr. Charles L.
Washington State University Research Foundation
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