Skip to main content

Enantiodifferential Approach for the Target Protein Detection of the Jasmonate Glucoside That Controls the Leaf Closure of Samanea saman

  • Protocol
  • First Online:
Plant Chemical Genomics

Part of the book series: Methods in Molecular Biology ((MIMB,volume 1795))

  • 1085 Accesses

Abstract

The synthetic photoaffinity probe designed to mimic bioactive molecules is one of the powerful tools for the identification of the target protein in living organisms. However, nonspecific interaction between the probe and nontargets would cause a misleading result in many cases of the photoaffinity labeling. In this chapter, we describe an enantiodifferential approach as a reliable method for the detection of the specific target protein of the bioactive natural product, jasmonate glucoside, a chemical factor that controls the nyctinastic leaf movement of the leguminous plants.

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

Access this chapter

Protocol
USD 49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 249.99
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

  1. Ziegler S, Pries V, Hedberg C, Waldmann H (2013) Target identification for small bioactive molecules: finding the needle in the haystack. Angew Chem Int Ed 52(10):2744–2792

    Article  CAS  Google Scholar 

  2. Dejonghe W, Russinova E (2017) Plant chemical genetics: from phenotype-based screens to synthetic biology. Plant Physiol 174(1):5–20

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Ueda M (2012) Chemical biology of natural products on the basis of identification of target proteins. Chem Lett 41(7):658–666

    Article  CAS  Google Scholar 

  4. Sletten EM, Bertozzi CR (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl 48(38):6974–6998

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Nakamura Y, Miyatake R, Matsubara A, Kiyota H, Ueda M (2006) Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds. Tetrahedron 62(37):8805–8813

    Article  CAS  Google Scholar 

  6. Nakamura Y, Miyatake R, Ueda M (2008) Enantiodifferential approach for the detection of the target membrane protein of the jasmonate glycoside that controls the leaf movement of Albizzia saman. Angew Chem Int Ed Engl 47(38):7289–7292

    Article  CAS  PubMed  Google Scholar 

  7. Ueda M, Nakamura Y (2006) Metabolites involved in plant movement and ‘memory’: nyctinasty of legumes and trap movement in the Venus flytrap. Nat Prod Rep 23(4):548–557

    Article  CAS  PubMed  Google Scholar 

  8. Ueda M, Nakamura Y (2007) Chemical basis of plant leaf movement. Plant Cell Physiol 48(7):900–907

    Article  CAS  PubMed  Google Scholar 

  9. Moran N (2015) Rhythmic leaf movements: physiological and molecular aspects. In: Rhythms in plants. Springer, Berlin, pp 57–95

    Chapter  Google Scholar 

  10. Moran N (2007) Osmoregulation of leaf motor cells. FEBS Lett 581(12):2337–2347

    Article  CAS  PubMed  Google Scholar 

  11. Nakamura Y, Mithofer A, Kombrink E, Boland W, Hamamoto S, Uozumi N, Tohma K, Ueda M (2011) 12-Hydroxyjasmonic acid glucoside is a COI1-JAZ-independent activator of leaf-closing movement in Samanea saman. Plant Physiol 155(3):1226–1236

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Ueda M, Okazaki M, Ueda K, Yamamura S (2000) A leaf-closing substance of Albizzia julibrissin Durazz. Tetrahedron 56(41):8101–8105

    Article  CAS  Google Scholar 

  13. Nakamura Y, Miyatake R, Inomata S, Ueda M (2008) Synthesis and bioactivity of potassium β-d-glucopyranosyl 12-hydroxy jasmonate and related compounds. Biosci Biotechnol Biochem 72(11):2867–2876

    Article  CAS  PubMed  Google Scholar 

  14. Ueda M, Yang G, Ishimaru Y, Itabashi T, Tamura S, Kiyota H, Kuwahara S, Inomata S, Shoji M, Sugai T (2012) Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: syntheses and biological evaluations. Bioorg Med Chem 20:5832–5843

    Article  CAS  PubMed  Google Scholar 

  15. Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV (2009) Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes. Angew Chem Int Ed Engl 48(43):8018–8021

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Tornøe CW, Christensen C, Meldal M (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem 67(9):3057–3064

    Article  CAS  PubMed  Google Scholar 

  17. Ueda M, Yang G, Nukadzuka Y, Ishimaru Y, Tamura S, Manabe Y (2015) Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity. Org Biomol Chem 13(1):55–58

    Article  CAS  PubMed  Google Scholar 

  18. Ueda M, Manabe Y, Otsuka Y, Kanzawa N (2011) Cassia obtusifolia MetE as a cytosolic target for potassium isolespedezate, a leaf-opening factor of Cassia plants: target exploration by a compact molecular-probe strategy. Chem Asian J 6(12):3286–3297

    Article  CAS  PubMed  Google Scholar 

  19. Manabe Y, Mukai M, Ito S, Kato N, Ueda M (2010) FLAG tagging by CuAAC and nanogram-scale purification of the target protein for a bioactive metabolite involved in circadian rhythmic leaf movement in Leguminosae. Chem Commun (Camb) 46(3):469–471

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank Dr. Y. Ishimaru (Tohoku Univ) for helpful discussion. This work was also supported in part by a Grant-in-Aid for Scientific Research (no. 23102012) on Innovative Areas “Chemical Biology of Natural Products” to M.U. from MEXT, Japan; a Grant-in-Aid for Scientific Research (nos. 26282207 and 17H00885 to M.U); JSPS A3 Foresight Program to M.U.; and JST (JPMJPR16Q4 to Y.T.).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Minoru Ueda .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2018 Springer Science+Business Media, LLC, part of Springer Nature

About this protocol

Check for updates. Verify currency and authenticity via CrossMark

Cite this protocol

Takaoka, Y., Ueda, M. (2018). Enantiodifferential Approach for the Target Protein Detection of the Jasmonate Glucoside That Controls the Leaf Closure of Samanea saman. In: Fauser, F., Jonikas, M. (eds) Plant Chemical Genomics. Methods in Molecular Biology, vol 1795. Humana Press, New York, NY. https://doi.org/10.1007/978-1-4939-7874-8_13

Download citation

  • DOI: https://doi.org/10.1007/978-1-4939-7874-8_13

  • Published:

  • Publisher Name: Humana Press, New York, NY

  • Print ISBN: 978-1-4939-7873-1

  • Online ISBN: 978-1-4939-7874-8

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics