Sesquiterpenes of the liverwort Scapania undulata |
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Authors: | Adio Adewale Martins Paul Claudia Kloth Petra König Wilfried A |
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Affiliation: | Institut für Organische Chemie, Universit?t Hamburg, Martin-Luther-King-Platz 6, D-20146, Hamburg, Germany. |
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Abstract: | The essential oil of the liverwort Scapania undulata, collected in the Harz mountains, Northern Germany, was analysed by gas chromatography (GC), GC-mass spectrometry (MS) and several new components were isolated and investigated by various NMR techniques. As new natural compounds the sesquiterpene hydrocarbons (+)-helminthogermacrene (1) [the 4Z-isomer of germacrene A (9)], (-)-cis-beta-elemene (2) as a Cope-rearrangement product of 1, (+)-beta-isolongibornene (3) and (-)-perfora-1,7-diene (4) could be identified. 1 has an identical mass spectrum and identical GC retention time on a non-polar stationary phase as germacrene A (9) but is considerably more stable than the latter. The Cope-rearrangement of 1 proceeds slowly at 350 degrees C and (-)-cis-beta-elemene (2) is formed together with small amounts of other diastereoisomers. |
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Keywords: | Scapania undulata Liverworts Sesquiterpene hydrocarbons Cope rearrangement (+)-Helminthogermacrene (+)-β-Isolongibornene (−)-cis-β-Elemene (−)-Perfora-1,7-diene |
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