Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 8, pp 1475–1480 | Cite as

Synthesis of a 13C-labelled seed-germination inhibitor (3,4,5-trimethylfuran-2(5H)-one) for the mode of action elucidation

  • Martin Pošta
  • Vilmos Soós
  • Petr Beier
Original Paper


It has been found that the butenolide 3,4,5-trimethylfuran-2(5H)-one, isolated from plant-derived smoke, efficiently inhibits seed germination and significantly reduces the effect of the highly active germination promotor karrikinolide (KAR1, 3-methyl-2H-furo[2,3-c]pyran-2-one), another smoke-derived compound. This paper reports the synthesis of stable isotope-labelled 3,4,5-trimethylfuran-2(5H)-ones containing one and two 13C atoms for the identification of metabolic degradation products in order to provide insight into the mechanism of action.

Graphical abstract


Butenolide Seed-germination inhibitor Carbon-13 Lactuca sativa Lactuca serriola Smoke 



The IOCB research plan RVO: 61388963, OTKA 114567 and Bolyai Fellowship, supporting this work, are acknowledged.

Supplementary material

706_2018_2179_MOESM1_ESM.docx (4.4 mb)
Supplementary material 1 (DOCX 4511 kb)


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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Institute of Organic Chemistry and Biochemistry, CAS, v.v.i.Prague 6Czech Republic
  2. 2.Department of Applied Genomics, Agricultural InstituteCentre for Agricultural Research, Hungarian Academy of SciencesMartonvásárHungary

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