Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14

Microbiology

Volumn 146, Issue 5, 2000, Pages 1129-1141

  Van Der Werf, Mariët J ^a,b   Boot, Anneke M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b TNO   (Netherlands)

Author keywords

Carveol; Carvone; Dihydrocarveol; Monoterpene metabolism; Rhodococcus erythropolis

Indexed keywords

BACTERIAL ENZYME; CARVEOL; CARVONE; DIHYDROCARVEOL; HEXANOIC ACID DERIVATIVE; ISOMERASE; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXEPANE DERIVATIVE; OXIDOREDUCTASE; OXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL METABOLISM; CONTROLLED STUDY; ENZYME ACTIVITY; NONHUMAN; PRIORITY JOURNAL; RHODOCOCCUS; STEREOISOMERISM;

ACTINOBACTERIA (CLASS); BACTERIA (MICROORGANISMS); ERYTHROPOLIS; RHODOCOCCUS ERYTHROPOLIS; UNCULTURED ACTINOMYCETE;

EID: 0034082694     PISSN: 13500872     EISSN: None     Source Type: Journal    
DOI: 10.1099/00221287-146-5-1129     Document Type: Article

References (37)

1. Alphand, V. & Furstoss, R. (1992). Microbiological transformations. 23. A surprising regioselectivity of microbiological Baeyer-Villiger oxidations of menthone and dihydrocarvone. Tetrahedron: Asymmetry 3, 379-382.
2. Banthorpe, D. V. (1994). Terpenoids. In Natural Products: Their Chemistry and Biological Significance, pp. 289-359. Edited by J. Mann, R. S. Davidson, J. B. Hobbs, D. V. Banthorpe & J. B. Harborne. Harlow, UK: Longman.
3. Barbirato, F., Verdoes, J. C., de Bont, J. A. M. & van der Werf, M. J. (1998). The Rhodococcus erythropolis DCL14 limonene-1,2-epoxide hydrolase gene encodes an enzyme belonging to a novel class of epoxide hydrolases. FEBS Lett 438, 293-296.
4. Bradford, M. M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72, 248-254.
5. Buckingham, J. (1998). In Dictionary of Natural Products on CD-ROM, Version 6-1. London: Chapman & Hall.
6. Burdock, G. A. (1995). Fenaroli's Handbook of Flavor Ingredients, 3rd edn. Boca Raton, FL: CRC Press.
7. van Dyk, M. S., van Rensburg, E., Rensburg, I. P. B. & Moleleki, N. (1998). Biotransformation of monoterpenoid ketones by yeasts and yeast-like fungi. J Mol Catal B (Enzymatic) 5, 149-154.
8. Guenther, A., Hewitt, C. N., Erickson, D. & 13 other authors (1995). A global model of natural volatile organic compound emissions. J Geophys Res 100, 8873-8892.
9. Harborne, J. B. (1991). Recent advances in the ecological chemistry of plant terpenoids. In Ecological Chemistry and Biochemistry of Plant Terpenoids, pp. 399-426. Edited by J. B. Harborne & F. A. Tomas-Barberan. Oxford: Clarendon Press.
10. Hartmans, S., Smits, J. P., van der Werf, M. J., Volkering, F. & de Bont, J. A. M. (1989). Metabolism of styrene oxide and 2-phenylethanol in the styrene-degrading Xanthobacter strain 124X. Appl Environ Microbiol 55, 2850-2855.
11. Hirata, T., Hamada, H., Aoki, T. & Suga, T. (1982). Stereoselectivity of the reduction of carvone and dihydrocarvone by suspensions of cells of Nicotiana tabacum. Photochemistry 21, 2209-2212.
12. McCaskill, D. & Croteau, R. (1997). Prospects for the bio-engineering of isoprenoid biosynthesis. Adv Biochem Eng Biotechnol 55, 107-146.
13. Mironowicz, A. & Siewiński, A. (1986). Biotransformations. XIX. Reduction of some terpenic ketones by means of immobilized cells of Rhodotorula mucilaginosa. Acta Biotechnol 6, 141-146.
14. Mironowicz, A., Raczkowska, J., Siewiński, A., Szykuła, J. & Zabża, A. (1982). Microbiological transformations. Part XIV. Microbiological reduction of (+)-carvone and eucarvone by Rhodotorula mucilaginosa. Pol J Chem 56, 735-739.
15. Nishimura, H., Hiramoto, S., Mizutani, J., Noma, Y., Furusaki, A. & Matsumoto, T. (1983). Structure and biological activity of bottrospicatol, a novel monoterpene produced by microbial transformation of (-)-cis-carveol. Agric Biol Chem 47, 2697-2699.
16. Noma, Y. (1980). Conversion of (-)-carvone by strains of Streptomyces, A-5-1, and Nocardia, 1-3-11. Agric Biol Chem 44, 807-812.
17. Noma, Y. & Asakawa, Y. (1992). Enantio-and diastereoselectivity in the biotransformation of carveols by Euglena gracilis Z. Phytochemistry 31, 2009-2011.
18. Noma, Y. & Nishimura, H. (1987). Bottrospicatols, novel monoterpenes produced on conversion of (-)-and (+)-cis-carveol by Streptomyces. Agric Biol Chem 51, 1845-1849.
19. Noma, Y. & Nonomura, S. (1974). Conversion of (-)-carvone and (+)-carvone by a strain of Aspergillus niger. Agric Biol Chem 38, 741-744.
20. Noma, Y., Nonomura, S., Ueda, H. & Tatsumi, C. (1974). Conversion of (+)-carvone by Pseudomonas ovalis, strain 6-1. Agric Biol Chem 38, 735-740.
21. Noma, Y., Nonomura, S. & Sakai, H. (1975). Epimerization of (-)-isodihydrocarvone to (-)-dihydrocarvone by Pseudomonas fragi IFO 3458. Agric Biol Chem 39, 437-441.
22. Noma, Y., Nishimura, H., Hiramoto, S., Iwami, M. & Tatsumi, C. (1982). A new compound, (4R,6R)-(+)-6,8-oxidomenth-1-en-9-ol produced by microbial conversion of (-)-cis-carveol. Agric Biol Chem 46, 2871-2872.
23. Ravid, U., Putievsky, E., Katzir, I., Weinstein, V. & Ikan, R. (1992). Chiral GC analysis of (S)(+)-and (R)(-)-carvone with high enantiomeric purity in caraway, dill and spearmint oils. Flavour fragrance J 7, 289-292.
24. Sauers, R. R. & Ahearn, G. P. (1961). The importance of steric effects in the Baeyer-Villiger oxidation. J Am Chem Soc 83, 2759-2762.
25. Shimoda, K., Hirata, T. & Noma, Y. (1998). Stereochemistry in the reduction of enones by the reductase from Euglena gracilis Z. Phytochemistry 49, 49-53.
26. Trudgill, P. W. (1986). Terpenoid metabolism by Pseudomonas. In The Bacteria. A Treatise on Structure and Function, vol. X, The Biology of Pseudomonas, pp. 483-525. Edited by J. R. Sokatch. Orlando, FL: Academic Press.
27. Trudgill, P. W. (1990). Microbial metabolism of monoterpenes -recent developments. Biodegradation 1, 93-105.
28. Trudgill, P. W. (1994). Microbial metabolism and transformation of selected monoterpenes. In Biochemistry of Microbial Degradation, pp. 33-61. Edited by C. Ratledge. Dordrecht: Kluwer.
29. Varie, D. L., Brennan, J., Briggs, B., Cronin, J. S., Hay, D. A., Rieck, J. A. & Zmijewski, M. J. (1998). Bioreduction of (R)-carvone and regioselective Baeyer-Villiger oxidations: application to the asymmetric synthesis of cryptophycin fragment A. Tetrahedron Lett 39, 8405-8408.
30. Verstegen-Kaaksma, A. A., Swarts, H. J., Jansen, B. J. M., de Groot, A., Bottema-MacGillavry, N. & Witholt, B. (1995). Application of S-(+)-carvone in the synthesis of biologically active natural products using chemical transformations and bioconversions. Ind Crops Prod 4, 15-21.
31. Welsh, F. W., Murray, W. D. & Williams, R. E. (1989). Microbiological and enzymatic production of flavor and fragrance chemicals. Crit Rev Biotechnol 9, 105-169.
32. van der Werf, M. J. (2000). Purification and characterization of a Baeyer-Villiger monooxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways. Biochem J (in press).
33. van der Werf, M. J., Guettler, M. V., Jain, M. K. & Zeikus, J. G. (1997). Environmental and physiological factors affecting the succinate product ratio during carbohydrate fermentation by Actinobacillus sp. 130Z. Arch Microbiol 167, 332-342.
34. van der Werf, M. J., Overkamp, K. M. & de Bont, J. A. M. (1998). Limonene-1,2-epoxide hydrolase from Rhodococcus erythropolis DCL14 belongs to a novel class of epoxide hydrolases. J Bacteriol 180, 5052-5057.
35. van der Werf, M. J., Swarts, H. J. & de Bont, J. A. M. (1999a). Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene. Appl Environ Microbiol 65, 2092-2102.
36. van der Werf, M. J., van der Ven, C., Barbirato, F., Eppink, M. H. M., de Bont, J. A. M. & van Berkel, W. J. (1999b). Stereo selective carveol dehydrogenase from Rhodococcus erythropolis DCL14. A novel nicotinoprotein belonging to the short-chain dehydrogenase/reductase superfamily. J Biol Chem 274, 26296-26304.
37. Williams, D. R. & Trudgill, P. W. (1994). Ring cleavage reactions in the metabolism of (-)-menthol and (-)-menthone by a Corynebacterium sp. Microbiology 140, 611-616.