Germacrenes from fresh costus roots

Phytochemistry. 2001 Oct;58(3):481-7. doi: 10.1016/s0031-9422(01)00291-6.

Abstract

Four germacrenes, previously shown to be intermediates in sesquiterpene lactone biosynthesis, were isolated from fresh costus roots (Saussurea lappa). The structures of (+)-germacrene A, germacra-1(10),4,11(13)-trien-12-ol, germacra-1(10),4,11(13)-trien-12-al, and germacra-1(10),4,11(13)-trien-12-oic acid were deduced by a combination of spectral data and chemical transformations. Heating of these compounds yields (-)-beta-elemene, (-)-elema-1,3,11(13)-trien-12-ol, (-)-elema-1,3,11(13)-trien-12-al, and elema-1,3,11(13)-trien-12-oic acid respectively, in addition to small amounts of their diastereomers. Acid induced cyclisation of the germacrenes yields selinene, costol, costal, and costic acid respectively. It is highly probable that the elemenes reported in literature for costus root oil are artefacts.

MeSH terms

  • Asteraceae / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Plant Roots / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Sesquiterpenes