Skip to main content

Catabolic Pathways and Enzymes Involved in the Anaerobic Degradation of Terpenes

  • Reference work entry
  • First Online:
Anaerobic Utilization of Hydrocarbons, Oils, and Lipids

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 379.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 449.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

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

    Google Scholar 

  • Boronat A, Rodríguez-Concepción M (2015) Terpenoid biosynthesis in prokaryotes. Adv Biochem Eng Biotechnol 148:3–18

    CAS  PubMed  Google Scholar 

  • 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Chiang Y-R and Ismail W (2017) Anaerobic biodegradation of steroids (this book)

    Google Scholar 

  • Drozdetskiy A, Cole C, Procter J, Barton GJ (2015) JPred4: a protein secondary structure prediction server. Nucl Acids Res 43:W389–W394

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • 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

    Article  Google Scholar 

  • 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

    Article  PubMed  Google Scholar 

  • 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

    Article  PubMed  Google Scholar 

  • Harder J (2009a) Isoprene, isoprenoids and sterols. In: Timmis KN (ed) Handbook of hydrocarbon and lipid microbiology. Springer, Heidelberg. https://doi.org/10.1007/978-3-540-77587-4_7

    Chapter  Google Scholar 

  • Harder J (2009b) Anaerobic degradation of isoprene-derived compounds. In: Timmis KN (ed) Handbook of hydrocarbon and lipid microbiology. Springer, Heidelberg. https://doi.org/10.1007/978-3-540-77587-4_68

    Chapter  Google Scholar 

  • Harder J, Probian C (1995) Microbial degradation of monoterpenes in the absence of molecular oxygen. Appl Environ Microbiol 61:3804–3808

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Harder J, Probian C (1997) Anaerobic mineralisation of cholesterol by a novel type of denitrifying bacterium. Arch Microbiol 167:269–274

    Article  CAS  PubMed  Google Scholar 

  • Harder J, Heyen U, Probian C, Foß S (2000) Anaerobic utilization of essential oils by denitrifying bacteria. Biodegradation 11:55–63

    Article  CAS  PubMed  Google Scholar 

  • 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hylemon PB, Harder J (1998) Biotransformation of monoterpenes, bile acids, and other isoprenoids in anaerobic ecosystems. FEMS Microbiol Rev 22:475–488

    Article  CAS  PubMed  Google Scholar 

  • Klemperer WB (1962) Some properties of rosette configurations of gravitating bodies in homographic equilibrium. Astron J 67:162–167

    Article  Google Scholar 

  • 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

    Article  CAS  PubMed  Google Scholar 

  • Liu B, Frostegard A, Shapleigh JP (2013) Draft genome sequences of five strains in the genus Thauera. Genome Announc 1:e00052–e00012

    PubMed  PubMed Central  Google Scholar 

  • Lüddeke F, Harder J (2011) Enantiospecific (S)-(+)-linalool formation from β-myrcene by linalool dehydratase-isomerase. Z Naturforsch C 66:409–412

    PubMed  Google Scholar 

  • 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

    Article  PubMed  PubMed Central  Google Scholar 

  • 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

    Article  PubMed  PubMed Central  Google Scholar 

  • Marmulla R (2015) The anaerobic linalool metabolism in the betaproteobacteria Castellaniella defragrans 65Phen and Thauera linaloolentis 47Lol. University Bremen, Dissertation

    Google Scholar 

  • Marmulla R, Harder J (2014) Microbial monoterpene transformations – a review. Front Microbiol 5:346

    Article  PubMed  PubMed Central  Google Scholar 

  • Marmulla R, Cala EP, Markert S, Schweder T, Harder J (2016a) The anaerobic linalool metabolism in Thauera linaloolentis 47 Lol. BMC Microbiol 16:76

    Article  PubMed  PubMed Central  Google Scholar 

  • Marmulla R, Å afarić 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

    Article  PubMed  PubMed Central  Google Scholar 

  • 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

    Google Scholar 

  • 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • 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

    Article  PubMed  PubMed Central  Google Scholar 

  • 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Schmidt-Dannert C (2015) Biosynthesis of terpenoid natural products in fungi. Adv Biochem Eng Biotechnol 148:19–61

    CAS  PubMed  Google Scholar 

  • 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

    Article  PubMed  PubMed Central  Google Scholar 

  • Sikkema J (1995) Mechanisms of membrane toxicity of hydrocarbons. Microbiol Rev 59:201–222

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tholl D (2015) Biosynthesis and biological functions of terpenoids in plants. Adv Biochem Eng Biotechnol 148:63–106

    CAS  PubMed  Google Scholar 

  • 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

    Article  Google Scholar 

  • 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgments

Jens Harder’s research on monoterpenes in the last dozen years was kindly financed via Friedrich Widdel by the Max Planck Society.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jens Harder .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer Nature Switzerland AG

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Harder, J., Marmulla, R. (2020). 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/10.1007/978-3-319-50391-2_8

Download citation

Publish with us

Policies and ethics