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The Structure of Hildecarpin, an Insect Antifeedant 6a-Hydroxypterocarpan from the Roots of Tephrosia Hildebrandtii Vatke

  • W. Lwande
  • M. D. Bentley
  • A. Hassanali
Research Article

Abstract

The structure of hildecarpin, an insect antifeedant 6a-hydroxypterocarpan isolated from the roots of Tephrosia hildebrandtii has been confirmed by a combination of degradation reactions, NMR and mass spectra. Hildecarpin has been dehydrated to the corresponding pterocarpene 3-hydroxy-2-methoxy-8,9-methylenedioxypterocarpene. Hydrogenation and hydrogenolysis of the pterocarpene has afforded the isoflavan 2′, 7-dihydroxy-6-methoxy-4′,5′-methylenedioxyisoflavan, acetylation of which has led to 2′,7-diacetoxy-6-methoxy-4′,5′-methylenedioxyisoflavan. The NMR and mass spectra of the degradation products confirm the structure previously assigned to hildecarpin.

Key Words

Hildecarpin pterocarpan flavonoid isoflavonoid Tephrosia hildebrandtii antifeedant antifungal Maruca testulalis 

Résumé

La structure de hildecarpin, un insecte antiparasitaire 6a-hydroxypterocarpan isolé des racines de Tephrosia hildebrandtii a été confirmer par une combinaison de réactions de dégradations, NMR et le masse spectre. Hildecarpin a été déshydrater au correspondant pterocarpene 3-hydroxy-2-methoxy-8,9-methylenedioxypterocarpene. L’hydrogénation et l’hydrogenolysis de le pterocarpene a fourni l’isoflavan 2′,7-dihydroxy-6-methoxy-4′,5′-methylenedioxyisoflavan, l’acetylation de laquelle a conduit à 2′,7-dia-cetoxy-6-methoxy-4′,5′-methylenedioxyisoflavan. Le NMR et le masse spectra des produits de dégradation confirme la structure qui était preá lablement assigner à hildecarpin.

Mots Cléf

Hildecarpin pterocarpan flavonoid isoflavonoid Tephrosia hildebrandtii antiparasitaire antimycosiaue Maruca testulalis 

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References

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Copyright information

© ICIPE 1986

Authors and Affiliations

  • W. Lwande
    • 1
  • M. D. Bentley
    • 2
  • A. Hassanali
    • 1
  1. 1.The International Centre of Insect Physiology and Ecology (ICIPE)NairobiKenya
  2. 2.Department of ChemistryUniversity of Maine at OronoOronoUSA

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