Abstract
Monoterpenes are ubiquitous and, in contrast to other terpenes, their anaerobic mineralization has been studied, especially in denitrifying betaproteobacteria. Castellaniella defragrans has a degradation pathway for cyclic monoterpenes, with a limonene dehydrogenase and a ring-cleavage reaction known from anoxygenic phototrophic bacteria. Toxic monoterpene alcohols are transformed in the periplasm by the linalool dehydratase/isomerase (Ldi) to the less toxic myrcene. Thauera linaloolentis degrades linalool with a membrane-anchored linalool isomerase and the enzymes of the Atu/Liu pathways for acyclic monoterpenes. The development of a genetic system for Castellaniella defragrans together with physiological and biochemical studies have provided an excellent toolbox to study the monoterpene metabolism. On the horizon, Pseudomonas aeruginosa and other gammaproteobacterial pseudomonads are waiting for a thorough exploration of their monoterpene metabolism.
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References
Asakawa Y, Noma Y (2016) Biotransformation of sesquiterpenoides, ionones, damascones, adamantanes, and aromatic compounds by green algae, fungi and mammals. In: KHC B, Buchbauer G (eds) Handbook of essential oils: science, technology, and applications, 2nd edn. CRC press, Boca Raton, pp 907–1011
Boronat A, Rodríguez-Concepción M (2015) Terpenoid biosynthesis in prokaryotes. Adv Biochem Eng Biotechnol 148:3–18
Brodkorb D, Gottschall M, Marmulla R, Lueddeke F, Harder J (2010) Linalool dehydratase-isomerase, a bifunctional enzyme in the anaerobic degradation of monoterpenes. J Biol Chem 285:30436–30442
Chiang Y-R and Ismail W (2017) Anaerobic biodegradation of steroids (this book)
Drozdetskiy A, Cole C, Procter J, Barton GJ (2015) JPred4: a protein secondary structure prediction server. Nucl Acids Res 43:W389–W394
Foß S, Harder J (1997) Microbial transformation of a tertiary allylalcohol: regioselective isomerisation of linalool to geraniol without nerol formation. FEMS Microbiol Lett 149:71–75
Foß S, Harder J (1998) Thauera linaloolentis sp. nov. and Thauera terpenica sp. nov., isolated on oxygen-containing monoterpenes (linalool, menthol, and eucalyptol) and nitrate. Syst Appl Microbiol 21:365–373
Foß S, Heyen U, Harder J (1998) Alcaligenes defragrans sp. nov., description of four strains isolated on alkenoic monoterpenes ((+)-menthene, alpha-pinene, 2-carene, and alpha-phellandrene) and nitrate. Syst Appl Microbiol 21:237–244
Harder J (2009a) Isoprene, isoprenoids and sterols. In: Timmis KN (ed) Handbook of hydrocarbon and lipid microbiology. Springer, Heidelberg. doi:10.1007/978-3-540-77587-4_7
Harder J (2009b) Anaerobic degradation of isoprene-derived compounds. In: Timmis KN(ed) Handbook of hydrocarbon and lipid microbiology. Springer, Heidelberg. doi:10.1007/978-3-540-77587-4_68
Harder J, Probian C (1995) Microbial degradation of monoterpenes in the absence of molecular oxygen. Appl Environ Microbiol 61:3804–3808
Harder J, Probian C (1997) Anaerobic mineralisation of cholesterol by a novel type of denitrifying bacterium. Arch Microbiol 167:269–274
Harder J, Heyen U, Probian C, Foß S (2000) Anaerobic utilization of essential oils by denitrifying bacteria. Biodegradation 11:55–63
Harms H (1996) Bacterial growth on distant naphthalene diffusing through water, air, and water-saturated and nonsaturated porous media. Appl Environ Microbiol 62:2286–2293
Heyen U, Harder J (2000) Geranic acid formation, an initial reaction of anaerobic monoterpene metabolism in denitrifying Alcaligenes defragrans. Appl Environ Microbiol 66:3004–3009
Hylemon PB, Harder J (1998) Biotransformation of monoterpenes, bile acids, and other isoprenoids in anaerobic ecosystems. FEMS Microbiol Rev 22:475–488
Klemperer WB (1962) Some properties of rosette configurations of gravitating bodies in homographic equilibrium. Astron J 67:162–167
Kuntze K, Shinoda Y, Moutakki H, McInerney MJ, Vogt C, Richnow HH, Boll M (2008) 6-Oxocyclohex-1-ene-1-carbonyl-coenzyme A hydrolases from obligately anaerobic bacteria: characterization and identification of its gene as a functional marker for aromatic compounds degrading anaerobes. Environ Microbiol 10:1547–1556
Liu B, Frostegard A, Shapleigh JP (2013) Draft genome sequences of five strains in the genus Thauera. Genome Announc 1:e00052–e00012
Lüddeke F, Harder J (2011) Enantiospecific (S)-(+)-linalool formation from β-myrcene by linalool dehydratase-isomerase. Z Naturforsch C 66:409–412
Lüddeke F, Dikfidan A, Harder J (2012a) Physiology of deletion mutants in the anaerobic β-myrcene degradation pathway in Castellaniella defragrans. BMC Microbiol 12:192
Lüddeke F, Wuelfing A, Timke M, Germer F, Weber J, Dikfidan A, Rahnfeld T, Linder D, Meyerdierks A, Harder J (2012b) Geraniol and geranial dehydrogenases induced in anaerobic monoterpene degradation by Castellaniella defragrans. Appl Environ Microbiol 78:2128–2136
Marmulla R (2015) The anaerobic linalool metabolism in the betaproteobacteria Castellaniella defragrans 65Phen and Thauera linaloolentis 47Lol. University Bremen, Dissertation
Marmulla R, Harder J (2014) Microbial monoterpene transformations – a review. Front Microbiol 5:346
Marmulla R, Cala EP, Markert S, Schweder T, Harder J (2016a) The anaerobic linalool metabolism in Thauera linaloolentis 47 Lol. BMC Microbiol 16:76
Marmulla R, Šafarić B, Markert S, Schweder T, Harder J (2016b) Linalool isomerase, a membrane-anchored enzyme in the anaerobic monoterpene degradation in Thauera linaloolentis 47Lol. BMC Biochem 17:6
Noma Y, Asakawa Y (2016) Biotransformation of monoterpenoids by microorganisms, insects, and mammals. In: KHC B, Buchbauer G (eds) Handbook of essential oils: science, technology, and applications, 2nd edn. CRC press, Boca Raton, pp 747–906
Pelletier DA, Harwood CS (2000) 2-Hydroxycyclohexanecarboxyl coenzyme A dehydrogenase, an enzyme characteristic of the anaerobic benzoate degradation pathway used by Rhodopseudomonas palustris. J Bacteriol 182:2753–2760
Petasch J, Disch EM, Markert S, Becher D, Schweder T, Hüttel B, Reinhard R, Harder J (2014) The oxygen-independent metabolism of cyclic monoterpenes in Castellaniella defragrans 65Phen. BMC Microbiol 14:164
Poudel N, Pfannstiel J, Simon O, Walter N, Papageorgiou AC, Jendrossek D (2015) The Pseudomonas aeruginosa isohexenyl glutaconyl coenzyme A hydratase (AtuE) is upregulated in citronellate-grown cells and belongs to the crotonase family. Appl Environ Microbiol 81:6558–6566
Schmidt-Dannert C (2015) Biosynthesis of terpenoid natural products in fungi. Adv Biochem Eng Biotechnol 148:19–61
Sievers F, Wilm A, Dineen D, Gibson TJ, Karplus K, Li W, Lopez R, McWilliam H, Remmert M, Söding J, Thompson JD, Higgins DG (2011) Fast, scalable generation of high-quality protein multiple sequence alignments using Clustal Omega. Mol Syst Biol 7:539
Sikkema J (1995) Mechanisms of membrane toxicity of hydrocarbons. Microbiol Rev 59:201–222
Strijkstra A, Trautwein K, Jarling R, Wöhlbrand L, Dörries M, Reinhardt R, Drozdowska M, Golding BT, Wilkes H, Rabus R (2014) Anaerobic activation of p-cymene in denitrifying betaproteobacteria: methyl group hydroxylation versus addition to fumarate. Appl Environ Microbiol 80:7592–7603
Tholl D (2015) Biosynthesis and biological functions of terpenoids in plants. Adv Biochem Eng Biotechnol 148:63–106
Weidenweber S, Marmulla R, Ermler U, Harder J (2015) X-ray structure of linalool dehydratase/isomerase from Castellaniella defragrans reveals enzymatic alkene synthesis. FEBS Lett 590:1375–1383
Yang J, Yan R, Roy A, Xu D, Poisson J, Zhang Y (2015) The I-TASSER suite: protein structure and function prediction. Nat Methods 12:7–8
Acknowledgments
Jens Harder’s research on monoterpenes in the last dozen years was kindly financed via Friedrich Widdel by the Max Planck Society.
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Harder, J., Marmulla, R. (2017). Catabolic Pathways and Enzymes Involved in the Anaerobic Degradation of Terpenes. In: Boll, M. (eds) Anaerobic Utilization of Hydrocarbons, Oils, and Lipids. Handbook of Hydrocarbon and Lipid Microbiology . Springer, Cham. https://doi.org/10.1007/978-3-319-33598-8_8-1
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DOI: https://doi.org/10.1007/978-3-319-33598-8_8-1
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