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A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus.

Günther RaspotnigFelix AnderlOlaf KunertMiriam SchaiderAdrian BrücknerMario SchubertStefan DötterlRoman FuchsHans-Jörg Leis
Published in: Journal of natural products (2020)
When threatened, the harvestman Egaenus convexus (Opiliones: Phalangiidae) ejects a secretion against offenders. The secretion originates from large prosomal scent glands and is mainly composed of two isomers of 4-hydroxy-5-octyl-4,5-dihydro-3H-furan-2-one (1), a β-hydroxy-γ-lactone. The compounds were characterized by GC-MS of their microreaction derivatives, HRMS, and NMR. After the synthesis of all four possible stereoisomers of 1, followed by their separation by chiral-phase GC, the absolute configurations of the lactones in the Egaenus secretion was found to be (4S,5R)-1 (90%) and (4S,5S)-1 (10%). Hydroxy-γ-lactones represent a new class of exocrine defense compounds in harvestmen.
Keyphrases
  • magnetic resonance
  • high resolution
  • mass spectrometry
  • capillary electrophoresis
  • solid state
  • gas chromatography