Skip to main content

Pyrethrin Biosynthesis and Its Regulation in Chrysanthemum cinerariaefolium

  • Chapter
  • First Online:
Pyrethroids

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 314))

Abstract

Pyrethrins are a natural insecticide biosynthesized by the plant pyrethrum [Chrysanthemum cinerariaefolium (Current species name: Tanacetum cinerariifolium)] of the family Asteraceae. Although pyrethrins have been used to control household pests for the past century, little is known about the mechanism of biosynthesis, contrasting with intensive research on their synthetic analogs, pyrethroids. The author studied pyrethrin biosynthesis in young seedlings of C. cinerariaefolium. The results of experiments using 13C-labeled glucose as the biosynthesis precursor indicated that the acid and alcohol moieties are biosynthesized via the 2-C-methyl-d-erythritol 4-phosphate (MEP) and oxylipin pathways, respectively. Further study on the effects of wound-induced signals in leaves showed that biosynthesis is enhanced in response to both volatile and nonvolatile signals.

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 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe I Über Isolierung und Konstitution des wirksamen Teiles des dalmatinischen Insektenpulvers. Helv Chim Acta 7:177–201

    Article  CAS  Google Scholar 

  2. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe II Zur Konstitution der Chrysanthemum-monocarbonsäure und -dicarbonsäure. Helv Chim Acta 7:201–211

    Article  CAS  Google Scholar 

  3. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe III Konstitution des Pyrethrolons. Helv Chim Acta 7:212–235

    Article  CAS  Google Scholar 

  4. Staudinger H, Ruzicka L (1924) Konstitution des Tetrahydro-pyrethrons. Insektentötende Stoffe IV. Helv Chim Acta 7:236–244

    Article  CAS  Google Scholar 

  5. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe V. Synthese des Tetrahydro-pyrethrons, des Reduktionsproduktes des Pyrethrolons. Helv Chim Acta 7:245–259

    Article  CAS  Google Scholar 

  6. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe VI Untersuchungen über Cyclopentanolonderivate und ihr Vergleich mit dem Pyrethrolon. Helv Chim Acta 7:377–390

    Article  CAS  Google Scholar 

  7. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe VII Synthesen der Chrysanthemumsäure und anderer Trimethylen-carbonsäuren mit ungesättigter Seitenkette. Helv Chim Acta 7:390–406

    Article  CAS  Google Scholar 

  8. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe VIII Versuche zur Herstellung von pyrethrolonähnlichen Alkoholen. Helv Chim Acta 7:406–441

    Article  CAS  Google Scholar 

  9. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe IX Weitere Versuche zur Herstellung von Cyclopentanolonderivaten mit ungesättigter Seitenkette. Helv Chim Acta 7:442–448

    Article  CAS  Google Scholar 

  10. Staudinger H, Ruzicka L (1924) Insektentötende Stoffe X Über die Synthese von Pyrethrinen. Helv Chim Acta 7:448–458

    Article  CAS  Google Scholar 

  11. La Forge FB, Soloway SB (1947) Constituents of pyrethrum flowers; revision of the structure of dihydrocinerolone. J Am Chem Soc 69:2932–2935

    Article  Google Scholar 

  12. LaForge FB, Barthel WF (1944) Heterologous nature of pyrethrolone. J Org Chem 9:242–249

    Article  CAS  Google Scholar 

  13. Godin PJ, Sleeman RJ, Snarey M, et al. (1966) The jasmolin, new insecticidally active constituents of Chrysanthemum cinerariaefolium Vis. J Chem Soc:332–334

    Google Scholar 

  14. Crombie L (1995) Chemistry of the pyrethrins. In: Casida JE, Quistad GB (eds) Pyrethrum flowers. Oxford University Press, Oxford, pp 123–193

    Google Scholar 

  15. Crombie L, Harper SH (1954) The chrysanthemum carboxylic acids. Part VI. The configuration of the chrysanthemic acids. J Chem Soc:470

    Google Scholar 

  16. Crombie L, Crossley J, Mitchard DA (1963) Synthesis, absolute configuration and ring fission of cis- and trans-homocaronic acid: their configurative relation to natural terpenes. J Chem Soc:4957–4969

    Google Scholar 

  17. Katsuda Y, Chikamoto T, Inouye Y (1958) The absolute configuration of naturally derived pyrethrolone and cinerolone. Bull Agric Chem Soc Jpn 22:427–428

    Article  CAS  Google Scholar 

  18. Bramwell AF, Crombie L, Hemesley P et al (1969) Nuclear magnetic resonance spectra of the natural pyrethrins and related compounds. Tetrahedron 25:1727–1741

    Article  CAS  Google Scholar 

  19. Begley MJ, Crombie L, Simmonds DJ, et al. (1972) Absolute configuration of pyrethrins. Configuration and structure of (+)-allethronyl (+)-trans-chrysanthemate 6-bromo-2,4-dinitrophenylhydrazone by X-ray methods. J Chem Soc Chem Commun:1276–1277

    Google Scholar 

  20. Begley MJ, Crombie L, Simmonds DJ et al (1974) X-ray analysis of synthetic (4S)-2-(prop-2’-enyl)rethronyl (1R)(3R)-chrysantemate 6-bromo-2,4-dinitrophenylhydrazone and (3R) chiroptical correlation with the six natural pyrethrin esters. J Chem Soc Perkin Trans 1:879–913

    Google Scholar 

  21. Rivera SB, Swedlund BD, King GJ et al (2001) Chrysanthemyl diphosphate synthase: isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from Chrysanthemum cinerariaefolium. Proc Natl Acad Sci USA 98:4373–4378

    Article  CAS  Google Scholar 

  22. Rohmer M, Knani M, Simonin P et al (1993) Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem J 295(Pt 2):517–524

    CAS  Google Scholar 

  23. Rohmer M, Seemann M, Horbach S et al (1996) Glyceraldehyde 3-phosphate and pyruvate as precursors of isoprenic units in an alternative non-mevalonate pathway for terpenoid biosynthesis. J Am Chem Soc 118:2564–2566

    Article  CAS  Google Scholar 

  24. Dubey VS, Bhalla R, Luthra R (2003) An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants. J Biosci 28:637–646

    Article  CAS  Google Scholar 

  25. Eisenreich W, Bacher A, Arigoni D et al (2004) Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell Mol Life Sci 61:1401–1426

    Article  CAS  Google Scholar 

  26. Rohmer M (2007) Diversity in isoprene unit biosynthesis: the methylerythritol phosphate pathway in bacteria and plastids. Pure Appl Chem 79:739–751

    Article  CAS  Google Scholar 

  27. Phillips MA, Leon P, Boronat A et al (2008) The plastidial MEP pathway: unified nomenclature and resources. Trends Plant Sci 13:619–623

    Article  CAS  Google Scholar 

  28. Crowley MP, Godin PJ, Inglis HS et al (1962) The biosynthesis of the “pyrethrins”. I. The incorporation of 14C-labelled compounds into the flowers of Chrysanthemum cinerariaefolium and the biosynthesis of chrysanthemum monocarboxylic acid. Biochim Biophys Acta 60:312–319

    Article  CAS  Google Scholar 

  29. Crowley MP, Inglis HS, Snarey M et al (1961) Biosynthesis of the pyrethrins. Nature 191:281–282

    Article  CAS  Google Scholar 

  30. Matsuda K, Kikuta Y, Haba A et al (2005) Biosynthesis of pyrethrin I in seedlings of Chrysanthemum cinerariaefolium. Phytochemistry 66:1529–1535

    Article  CAS  Google Scholar 

  31. Feussner I, Wasternack C (2002) The lipoxygenase pathway. Annu Rev Plant Biol 53:275–297

    Article  CAS  Google Scholar 

  32. Ueda H, Matsuda K (2011) VOC-mediated within-plant communications and nonvolatile systemic signals upregulate pyrethrin biosynthesis in wounded seedlings of Chrysanthemum cinerariaefolium. J Plant Interact 6:89–91

    Google Scholar 

  33. Arimura G, Matsui K, Takabayashi J (2009) Chemical and molecular ecology of herbivore-induced plant volatiles: proximate factors and their ultimate functions. Plant Cell Physiol 50:911–923

    Article  CAS  Google Scholar 

  34. Heil M, Karban R (2010) Explaining evolution of plant communication by airborne signals. Trends Ecol Evol 25:137–144

    Article  Google Scholar 

  35. Kikuta Y, Ueda H, Nakayama K et al (2011) Specific regulation of pyrethrin biosynthesis in Chrysanthemum cinerariaefolium by a blend of volatiles emitted from artificially damaged conspecific plants. Plant Cell Physiol 52:588–596

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The author was supported by Grant-in-Aid for Scientific Research (S) (No. 19101009) and Core-to-Core Program (No. 20004) from the Japan Society for the Promotion of Science. The author was also supported by Strategic Project to Support the Formation of Research Bases at Private Universities: Matching Fund Subsidy (S1101035) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kazuhiko Matsuda .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Matsuda, K. (2011). Pyrethrin Biosynthesis and Its Regulation in Chrysanthemum cinerariaefolium . In: Matsuo, N., Mori, T. (eds) Pyrethroids. Topics in Current Chemistry, vol 314. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_271

Download citation

Publish with us

Policies and ethics