Physiology of deletion mutants in the anaerobic β-myrcene degradation pathway in Castellaniella defragrans

BMC Microbiology

Volumn 12, Issue , 2012, Pages

  Lüddeke, Frauke ^a   Dikfidan, Aytac ^a   Harder, Jens ^a  

^a MAX PLANCK INSTITUTE FOR MARINE MICROBIOLOGY   (Germany)

Author keywords

myrcene; Anaerobic degradation; Genetic system; Geraniol dehydrogenase; Linalool dehydratase isomerase; phellandrene

Indexed keywords

ALCOHOL DEHYDROGENASE; CARBON; GERANIOL; LINALOOL; MYRCENE; OXIDOREDUCTASE; TERPENE;

ARTICLE; BACTERIAL GENOME; BACTERIAL GROWTH; BACTERIAL STRAIN; BETAPROTEOBACTERIA; BIOMASS; CASTELLANIELLA DEFRAGRANS; DELETION MUTANT; ENERGY RESOURCE; ENZYME ASSAY; ENZYME DEGRADATION; EXPRESSION VECTOR; GROWTH RATE; IN VIVO STUDY; NONHUMAN; PHENOTYPE;

ALCALIGENACEAE; ALCOHOL OXIDOREDUCTASES; CARBON; ENERGY METABOLISM; GENE DELETION; GENETICS, MICROBIAL; HYDRO-LYASES; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR BIOLOGY; MONOTERPENES; RECOMBINATION, GENETIC;

EID: 84865638150     PISSN: None     EISSN: 14712180     Source Type: Journal    
DOI: 10.1186/1471-2180-12-192     Document Type: Article

References (72)

1. Impact of climate variability and land use changes on global biogenic volatile organic compound emissions. Lathiere J, Hauglustaine DA, Friend AD, De Noblet-Ducoudrè N, Viovy N, Folberth GA, Atmos Chem Phys 2006 6 2129 2146 10.5194/acp-6-2129-2006 (Pubitemid 43980740)
2. Biogenic volatile organic compounds (VOC): an overview on emission, physiology and ecology. Kesselmeier J, Staudt M, J Atmos Chem 1999 33 23 88 10.1023/A:1006127516791 (Pubitemid 29151350)
3. Plant volatiles: recent advantages and future perspectives. Dudareva N, Negre F, Nagegowda DA, Orlova I, Crit Rev Plant Sci 2006 25 417 440 10.1080/07352680600899973 (Pubitemid 44449279)
4. Isoprene emission from plants: why and how. Sharkey TD, Wiberly AE, Donohue AR, Ann Bot 2008 101 5 18 17921528 (Pubitemid 350274502)
5. Volatile monoterpenes in soil atmosphere under birch and conifers: effects on soil N transformations. Smolander A, Ketolab RA, Kotiahod T, Kanervaa S, Suominene K, Kitunena V, Soil Biol Biochem 2006 38 3436 3442 10.1016/j.soilbio.2006.05.019 (Pubitemid 44573289)
6. Monoterpene emissions from soil in a Sitka spruce forest. Hayward S, Muncey RJ, James AE, Halsall CJ, Hewitt CN, Atmos Environ 2001 35 4081 4087 10.1016/S1352-2310(01)00213-8 (Pubitemid 32600872)
7. Volatile organic compounds in the roots and rhizosphere of pinus spp. Lin C, Owen SM, Penuelas J, Soil Biol Biochem 2007 39 951 960 10.1016/j.soilbio. 2006.11.007 (Pubitemid 46161611)
8. Microbial consumption and production of volatile organic compounds at the soil-litter interface. Ramirez KS, Lauber CL, Fierer N, Biogeochemistry 2010 99 97 107 10.1007/s10533-009-9393-x
9. Effects of monoterpenoids, acting alone or in pairs, on seed germination and subsequent seedling growth. Vokou D, Douvli P, Blionis GJ, Halley JM, J Chem Ecol 2003 29 2281 2301 10.1023/A:1026274430898 14682512 (Pubitemid 37429887)
10. Volatile organic compound (VOC) emissions from soil and litter samples. Leff JW, Fierer N, Soil Biol Biochem 2008 40 1629 1636 10.1016/j.soilbio.2008. 01.018
11. Activation of soil respiration and shift of the microbial population balance in soil as a response to lavendula stoechas essential oil. Vokou D, Chalkos D, Karamanlidou G, Yiangou M, J Chem Ecol 2002 28 755 768 10.1023/A:1015236709767 12035924 (Pubitemid 34498942)
12. Terpenoids: opportunities for biosynthesis of natural product drugs using engineered microorganisms. Ajikumar PA, Tyo K, Carlsen S, Mucha O, Phon TH, Stephanopoulos G, Mol Pharm 2008 5 167 190 10.1021/mp700151b 18355030 (Pubitemid 351579123)
13. Prokaryotic hopanoids: the biosynthesis of the bacteriohopane skeleton-formation of isoprenic units from two distinct acetate pools and a novel type of carbon/carbon linkage between a triterpene and D-ribose. Flesch G, Rohmer M, Eur J Biochem 1988 175 405 411 10.1111/j.1432-1033.1988.tb14210.x 3136017
14. Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants. Lichtenthaler HK, Rohmer M, Schwender J, Physiol Plant 1997 101 643 652 10.1111/j.1399-3054.1997.tb01049.x (Pubitemid 28028891)
15. Terpenoid metabolism in wildtype and transgenic arabidopsis plants. Aharoni A, Giri AP, Deuerlein S, Griepink F, de Kogel WJ, Verstappen FWA, Verhoeven HA, Jongsma MA, Schwab W, Bouwmeester HJ, Plant Cell 2003 15 2866 2884 10.1105/tpc.016253 14630967 (Pubitemid 37546257)
16. Biosynthesis of mono- and sesquiterpenes in carrot roots and leaves (Daucus carota L.): metabolic cross talk of cytosolic mevalonate and plastidial methylerythritol phosphate pathways. Hampel D, Mosandl A, Wüst M, Phytochemistry 2005 66 305 311 10.1016/j.phytochem.2004.12.010 15680987 (Pubitemid 40169990)
17. The FEMA GRAS assessment of aliphatic and aromatic terpene hydrocarbons used as flavor ingredients. Adams TB, Gavin CL, McGowen MM, Waddell WJ, Cohen SM, Feron VJ, Marnett LJ, Munro IC, Portoghese PS, Rietjens IMCM, Smith RL, Food Chem Toxicol 2011 49 2471 2494 10.1016/j.fct.2011.06.011 21726592
18. Geraniol-a review of a commercially important fragrance material. Chen W, Viljoen AM, S Afr J Bot 2010 76 643 651 10.1016/j.sajb.2010.05.008
19. Microbiological transformations of terpenes. IX. Pathways of degradation of limonene in a soil pseudomonad. Dhavalikar RS, Rangachari PN, Bhattacharyya PK, Indian J Biochem 1966 3 158 164 4227571
20. Degradation of isoprenoid compounds by microorganisms 1. Isolation and characterization of an isoprenoid-degrading bacterium, pseudomonas citronellolis n. sp. Seubert W, J Bacteriol 1960 79 426 434 14445211
21. Microbiological transformation of terpenes. XI. Pathways of degradation of - and -pinenes in a soil pseudomonad (PL-strain). Shukla OP, Bhattacharyya PK, Ind J Biochem 1968 5 92 101
22. Biodegradation of acyclic isoprenoids by pseudomonas species. Cantwell SG, Lau EP, Watt DS, Fall R, J Bacteriol 1978 135 324 333 681275 (Pubitemid 8402116)
23. Identification of genes and proteins necessary for catabolism of acyclic terpenes and leucine/isovalerate in pseudomonas aeruginosa. Förster-Fromme K, Höschle B, Mack C, Bott M, Armbruster W, Jendrossek D, Appl Environ Microbiol 2006 72 4819 4828 10.1128/AEM.00853-06 16820476 (Pubitemid 44078809)
24. Identification and sequencing of -myrcene catabolism genes from pseudomonas sp. strain M1. Iurescia S, Marconi M, Tofani D, Gambacorta A, Paterno A, Devirgiliis C, van der Werf M, Zennaro E, Appl Environ Microbiol 1999 65 2871 2876 10388678 (Pubitemid 29315555)
25. Metabolism of a monoterpene alcohol, linalool, by a soil pseudomonad. Madyastha KM, Bhattacharyya PK, Vajdyanathan CS, Can J Microbiol 1977 23 230 239 10.1139/m77-035 851909 (Pubitemid 8078236)
26. Pseudomonas delhiensis sp. nov., from a fly ash dumping site of a thermal power plant. Prakash O, Kumari K, Lal R, Int J Syst Evol Microbiol 2007 57 527 531 10.1099/ijs.0.64456-0 17329778 (Pubitemid 46437865)
27. -Pinene metabolism by pseudomonas putida. Tudroszen NJ, Kelly DP, Millis NF, Biochem J 1977 168 315 318 597274
28. Plasmid involvement in acyclic isoprenoid metabolism by pseudomonas putida. Vandenbergh PA, Wright AM, Appl Environ Microbiol 1983 45 1953 1955 16346325 (Pubitemid 13027716)
29. Bioproduction of perillyl alcohol and related monoterpenes by isolates of bacillus stearothermophilus. Chang HC, Oriel PJ, J Food Sci 1994 59 660 662 10.1111/j.1365-2621.1994.tb05588.x
30. Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene. van der Werf M, Swarts HJ, de Bont JAM, Appl Environ Microbiol 1999 65 2092 2102 10224006
31. Cloning of four genes involved in limonene hydroxylation from enterobacter cowanii 6L. Yang EJ, Park YJ, Chang HC, J Microbiol Biotechnol 2007 17 1169 1176 18051329 (Pubitemid 47272271)
32. Initial enzymatic steps in the degradation of -pinene by pseudomonas fluorescens NCIMB 11671. Best DJ, Floyd NC, Magalhaes A, Burfield A, Rhodes PM, Biocatalysis 1987 1 147 159 10.3109/10242428709040139
33. Bacterial metabolism of -pinene: pathway from -pinene oxide to acyclic metabolites in nocardia sp. strain P18.3. Griffiths ET, Bociek SM, Harries PC, Jeffcoat R, Sissons DJ, Trudgill PW, J Bacteriol 1987 169 4972 4979 3667521
34. Limonene and its oxyfunctionalized compounds: biotransformation by microorganisms and their role as functional bioactive compounds. Marostica MR Jr, Pastore GM, Food Sci Biotechnol 2009 18 833 841
35. Exploration of -pinene degradation pathway of pseudomonas rhodesiae CIP 107491. Application to novalic acid production in a bioreactor. Linares D, Fontanille P, Larroche C, Food Res Int 2009 42 461 469 10.1016/j.foodres.2008. 12.001
36. Microbial metabolims of monoterpenes - recent developments. Trudgill PW, Biodegradation 1990 1 93 105 10.1007/BF00058829 1368150
37. Protein-components of a cytochrome P-450 linalool 8-methyl hydroxylase. Ullah AJH, Murray RI, Bhattacharyya PK, Wagner GC, Gunsalus IC, J Biol Chem 1990 265 1345 1351 2295633
38. Xanthobacter sp C20 contains a novel bioconversion pathway for limonene. van der Werf MJ, Keijzer PM, van der Schaft PH, J Biotechnol 2000 84 133 143 10.1016/S0168-1656(00)00348-5
39. Microbial degradation of monoterpenes in the absence of molecular oxygen. Harder J, Probian C, Appl Environ Microbiol 1995 61 3804 3808 8526489
40. Alcaligenes defragrans sp. nov., description of four strains isolated on alkenoic monoterpenes ((+)-menthene, -pinene, 2-carene, and -phellandrene) and nitrate. Foss S, Heyen U, Harder J, Syst Appl Microbiol 1998 21 237 244 10.1016/S0723-2020(98)80028-3 9704110 (Pubitemid 28379508)
41. Castellaniella gen. nov., to accommodate the phylogenetic lineage of alcaligenes defragrans, and proposal of castellaniella defragrans gen. nov., comb. nov. and castellaniella denitrificans sp. nov. Kämpfer P, Denger K, Cook AM, Lee ST, Jäckel U, Denner EBM, Busse HJ, Int J Syst Evol Microbiol 2006 56 815 819 10.1099/ijs.0.63989-0 16585701
42. Cometabolic isoterpinolene formation from isolimonene by denitrifying alcaligenes defragrans. Heyen U, Harder J, FEMS Microbiol Lett 1998 169 67 71 10.1111/j.1574-6968.1998.tb13300.x (Pubitemid 28537900)
43. Geranic acid formation, an initial reaction of anaerobic monoterpene metabolism in denitrifying alcaligenes defragrans. Heyen U, Harder J, Appl Environ Microbiol 2000 66 3004 3009 10.1128/AEM.66.7.3004-3009.2000 10877798 (Pubitemid 30497610)
44. The atu and liu clusters are involved in the catabolic pathways for acyclic monoterpenes and leucine in Pseudomonas aeruginosa. Aguilar JA, Zavala AN, Díaz-Pérez C, Cervantes C, Díaz-Pérez AL, Campos-García J, Appl Environ Microbiol 2006 72 2070 2079 10.1128/AEM.72.3.2070-2079.2006 16517656
45. Catabolism of citronellol and related acyclic terpenoids in pseudomonads. Förster-Fromme K, Jendrossek D, Appl Microbiol Biotechnol 2010 87 859 869 10.1007/s00253-010-2644-x 20490788
46. Linalool dehydratase-isomerase, a bifunctional enzyme in the anaerobic degradation of monoterpenes. Brodkorb D, Gottschall M, Marmulla R, Lüddeke F, Harder J, J Biol Chem 2010 285 30406 30442
47. Geraniol dehydrogenase and geranial dehydrogenase induced in the anaerobic monoterpene degradation of castellaniella defragrans. Lüddeke F, Wülfing A, Timke M, Germer F, Weber J, Dikfidan A, Rahnfeld T, Linder D, Meyerdierks A, Harder J, Appl Environ Microbiol 2012 78 2128 2136 10.1128/AEM.07226-11 22286981
48. Enantiospecific (S)-(+)-linalool formation from -myrcene by linalool dehydratase-isomerase. Lüddeke F, Harder J, Z Naturforsch C Biosci 2011 66c 409 412
49. Diversity, taxonomy and evolution of medium-chain dehydrogenase/reductase superfamily. Riveros-Rosas H, Julian-Sanchez A, Villalobos-Molina R, Pardo JP, Pina E, Eur J Biochem 2003 270 3309 3334 10.1046/j.1432-1033.2003.03704.x 12899689 (Pubitemid 37020921)
50. Biotransformation of limonene by bacteria, fungi, yeasts, and plants. Duetz WA, Bouwemeester H, van Beilen JB, Witholt B, Appl Microbiol Biotechnol 2003 61 269 277 12743755 (Pubitemid 36683522)
51. Limonene bioconversion to high concentrations of a single and stable product, perillic acid, by a solvent-resistant pseudomonas putida strain. Speelmans G, Bijlsma A, Eggink G, Appl Microbiol Biotechnol 1998 50 538 544 10.1007/s002530051331 (Pubitemid 28555290)
52. Biocatalytic production of perillyl alchohol from limonene using a novel mycobaterium sp. cytochrome P450 alkane hydroxlase expressed in pseudomonas putida. van Beilen JB, Holtackers R, Lüscher D, Bauer U, Witholt B, Duetz WA, Appl Environ Microbiol 2005 71 173 1744
53. Ethylbenzene dehydrogenase, a novel hydrocarbon-oxidizing molybdenum/iron-sulfur/heme enzyme. Kniemeyer O, Heider J, J Biol Chem 2001 276 21381 21386 10.1074/jbc.M101679200 11294876
54. Initial steps in the anoxic metabolism of cholesterol by the denitrifying sterolibacterium denitrificans. Chiang YR, Ismail W, Müller M, Fuchs G, J Biol Chem 2007 282 13240 13249 10.1074/jbc.M610963200 17307741 (Pubitemid 47100524)
55. Adaptation to -myrcene catabolism in Pseudomonas sp. M1: an expression proteomic analysis. Santos PM, Sa-Correia I, Proteomics 2009 9 510 5111
56. Membrane toxicity of antimicrobial compounds from essential oils. Di Pasqua R, Betts G, Hoskins N, Edwards M, Ercolini D, Mauriello G, J Agric Food Chem 2007 55 4863 4870 10.1021/jf0636465 17497876 (Pubitemid 46960917)
57. Mechanisms of membrane toxicity of hydrocarbons. Sikkema J, de Bont JAM, Poolman B, FEMS Microbiol Rev 1995 59 201 222
58. Molecular characterization of microbial alcohol dehydrogenases. Reid MF, Fewson CA, Crit Rev Microbiol 1994 2 13 56 (Pubitemid 24093757)
59. PQQ-dependent alcohol dehydrogenase (QEDH) of pseudomonas aeruginosa is involved in catabolism of acyclic terpenes. Chattopadhyay A, Förster-Fromme K, Jendrossek D, J Bas Microbiol 2010 50 119 124
60. Characterization of a pseudomonas putida allylic alcohol dehydrogenase induced by growth on 2-methyl-3-buten-2-ol. Malone VF, Chastain AJ, Ohlsson JT, Poneleit LS, Nemecek-Marshall M, Fall R, Appl Environ Microbiol 1999 65 2622 2630 10347052
61. A distinct type of alcohol dehydrogenase, adh4+, complements ethanol fermentation in an adh1-deficient strain of Schizosaccharomyces pombe. Sakurai M, Tohda H, Kumagai H, Giga-Hama Y, FEMS Yeast Res 2004 4 649 654 10.1016/j.femsyr.2003.12.009 15040954 (Pubitemid 38369139)
62. Analysis of the enzymatic formation of citral in the glands of sweet basil. Iijima Y, Wang G, Fridman E, Pichersky E, Arch Biochem Biophys 2006 448 141 149 10.1016/j.abb.2005.07.026 16150417
63. A broad host range mobilization system for in vivo genetic engineering: transposon mutagenesis in gram-negative bacteria. Simon R, Priefer U, Puhler A, Nat Biotechnol 1983 1 784 791 10.1038/nbt1183-784 (Pubitemid 14239484)
64. Small mobilizable multi-purpose cloning vectors derived from the escherichia coli plasmids pK18 and pK19: selection of defined deletions in the chromosome of corynebacterium glutamicum. Schäfer A, Tauch A, Jager W, Kallnowski J, Thierbach G, Pühler A, Gene 1994 145 69 73 10.1016/0378-1119(94)90324-7 8045426 (Pubitemid 24224965)
65. Four new derivatives of the broad host range cloning vector pBBR1MCS, carrying different antibiotic resistance cassettes. Kovach ME, Elzer PH, Hill DS, Robertson GT, Farris MA, Roop RM, Peterson KM, Gene 1995 166 175 176 10.1016/0378-1119(95)00584-1 8529885
66. Sambrook J, Russel DW, Molecular cloning: a laboratory manual, ed 3 Cold Spring Harbor: Cold Spring Harbor laboratory Press 2001
67. High efficiency transformation of escherichia coli with plasmids. Inoue H, Nojima H, Okayama H, Gene 1990 96 23 28 10.1016/0378-1119(90)90336-P 2265755
68. A general method of in vitro preparation and specific mutagenesis of DNA fragments: study of protein and DNA interactions. Higuchi R, Krummel B, Saiki RK, Nucleic Acids Res 1988 16 7351 7367 10.1093/nar/16.15.7351 3045756
69. pBBR1MCS: a broad-host-range cloning vector. Kovach ME, Phillips RW, Elzer PH, Roop RM, Peterson KM, Biotechniques 1994 16 800 802 8068328 (Pubitemid 2103380)
70. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Bradford MM, Anal Biochem 1976 72 248 254 10.1016/0003-2697(76)90527-3 942051
71. Biorad, BioRad Protein Assay. Instruction Manual Munich: BioRad 1994
72. Anaerobic mineralization of cholesterol by a novel type of denitrifying bacterium. Harder J, Probian C, Arch Microbiol 1997 167 269 274 10.1007/s002030050442 9094222 (Pubitemid 27166217)