Skip to main content

Isoprenoid Quinones in Plants: Functional Diversity of

  • Living reference work entry
  • First Online:
Encyclopedia of Lipidomics
  • 137 Accesses

Definition

Isoprenoid quinones: isoprenoid quinones are characterized by an aromatic head group with an even number of oxygen functions and an isoprenoid aliphatic side chain.

Structure and Occurrence

Isoprenoid quinones represent an important group of compounds with lipid-soluble character that occur in membranes. They are composed of a quinone hydrophilic head group and a prenyl side chain, similar to tocochromanols (see Tocochromanols in Plants). The majority of naturally occurring isoprenoid quinones are naphtho- or benzoquinones. They mainly function as carriers in photosynthetic and respiratory electron transport chains. The naphthoquinones comprise menaquinones and phylloquinones that, historically, are classified as vitamin K group. Menaquinones are part of bacterial photosynthetic and respiratory electron transport chains. Phylloquinones have similar functions in electron transport chains of photosystem I in plants. Benzoquinones comprise ubiquinones and plastoquinones....

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

Access this chapter

Institutional subscriptions

Abbreviations

CoA:

Coenzyme AD

DHNA:

1,4-Dihydroxy-2-2naphthoate

DXP:

1-Deoxyxylulose-5-phosphate pathway

MenB:

1,4-Dihydroxy-2-naphthoyl-CoA synthase

MenC:

o-Succinyl benzoate synthase

MenD:

2-Succinyl-5-enoylpyruvyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase

MenE:

o-Succinyl benzoic acid-CoA synthase

MenF:

Isochorismate synthase

MenH:

2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase

UbiB:

Monooxygenase

UbiC:

Chorismate pyruvate-lyase

UbiD, UbiX:

Carboxylases

UbiE:

Nonspecific C-methyltransferase

UbiF:

Monooxygenase

UbiG:

O-Methyltransferase

UbiH:

Monooxygenase

References

  • Bentinger M, Tekle M, Dallner G. Coenzyme Q – Biosynthesis and functions. Biochem Biophys Res Commun. 2010;396:74–9.

    Article  CAS  PubMed  Google Scholar 

  • Bouvier F, Rahier A, Camara B. Biogenesis, molecular regulation and function of plant isoprenoids. Prog Lipid Res. 2005;44:357–429.

    Article  CAS  PubMed  Google Scholar 

  • Hemmerlin A, Harwood JL, Bach TJ. A raison d’être for two distinct pathways in the early steps of plant isoprenoid biosynthesis? Prog Lipid Res. 2012;51:95–148.

    Article  CAS  PubMed  Google Scholar 

  • Hiratsuka T, Furihata K, Ishikawa J, Yamashita H, Itoh N, Seto H, Dairi T. An alternative menaquinone biosynthetic pathway operating in microorganisms. Science. 2008;321:1670–3.

    Article  CAS  PubMed  Google Scholar 

  • Lange BM, Rujan T, Martin W, Croteau R. Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes. Proc Natl Acad Sci U S A. 2000;97:13172–7.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Martinis J, Kessler F, Glauser G. A novel method for prenylquinone profiling in plant tissues by ultra-high pressure liquid chromatography-mass spectrometry. Plant Methods. 2011;7:23.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Meganathan R. Ubiquinone biosynthesis in microorganisms. FEMS Microbiol Lett. 2001;203:131–9.

    Article  CAS  PubMed  Google Scholar 

  • Nowicka B, Kruk J. Occurrence, biosynthesis and function of isoprenoid quinones. Biochim Biophys Acta-Bioenerg. 2010;1797:1587–605.

    Article  CAS  Google Scholar 

  • Widhalm JR, van Oostende C, Furt F, Basset GJC. A dedicated thioesterase of the Hotdog-fold family is required for the biosynthesis of the naphthoquinone ring of vitamin K1. Proc Natl Acad Sci U S A. 2009;106:5599–603.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Franz Hadacek .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2017 Springer Science+Business Media B.V.

About this entry

Cite this entry

Hadacek, F. (2017). Isoprenoid Quinones in Plants: Functional Diversity of. In: Wenk, M. (eds) Encyclopedia of Lipidomics. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-7864-1_137-1

Download citation

  • DOI: https://doi.org/10.1007/978-94-007-7864-1_137-1

  • Received:

  • Accepted:

  • Published:

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-007-7864-1

  • Online ISBN: 978-94-007-7864-1

  • eBook Packages: Springer Reference Biomedicine and Life SciencesReference Module Biomedical and Life Sciences

Publish with us

Policies and ethics