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Related Experiment Videos

Germacrenes from fresh costus roots.

J W de Kraker1, M C Franssen, A de Groot

  • 1Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB, The, Wageningen, Netherlands.

Phytochemistry
|September 15, 2001
PubMed
Summary

Four germacrenes from costus roots are key intermediates in sesquiterpene lactone biosynthesis. Their transformations yield elemenes and selinenes, suggesting literature elemenes are artefacts.

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Phytochemistry

Background:

  • Sesquiterpene lactones are significant plant secondary metabolites.
  • Costus roots (Saussurea lappa) are a known source of sesquiterpenes.
  • Germacrenes are recognized as biosynthetic intermediates.

Purpose of the Study:

  • To isolate and elucidate the structures of germacrene intermediates from costus roots.
  • To investigate the chemical transformations of these germacrenes.
  • To clarify the origin of elemenes reported in costus root oil.

Main Methods:

  • Isolation of compounds from fresh costus roots.
  • Structure elucidation using spectral data (NMR, MS, etc.).
  • Chemical transformations including thermal rearrangement and acid-catalyzed cyclization.

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Main Results:

  • Four germacrenes, including (+)-germacrene A, were isolated and characterized.
  • Thermal rearrangement yielded various elemenes and their diastereomers.
  • Acid-catalyzed cyclization produced selinenes, costol, costal, and costic acid.
  • Evidence suggests that elemenes in costus root oil are likely artefacts.

Conclusions:

  • The identified germacrenes are crucial intermediates in sesquiterpene lactone biosynthesis.
  • The study provides a chemical basis for the formation of elemenes and selinenes from germacrenes.
  • This research refutes the natural occurrence of elemenes in costus root oil, attributing them to artefacts.