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The structure of hildecarpin, an insect antifeedant 6a-hydroxypterocarpan from the roots of Tephrosia hildebrandtii Vatke

Published online by Cambridge University Press:  19 September 2011

W. Lwande ,
M. D. Bentley  and
A. Hassanali
W. Lwande
Affiliation:
The International Centre of Insect Physiology and Ecology (ICIPE), P.O. Box 30772, Nairobi, Kenya
M. D. Bentley
Affiliation:
Department of Chemistry, University of Maine at Orono, Orono, ME 04469, U.S.A.
A. Hassanali
Affiliation:
The International Centre of Insect Physiology and Ecology (ICIPE), P.O. Box 30772, Nairobi, Kenya
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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-diacet6xy-6-methoxy-4′,5′-methylenedioxyisoflavan. The NMR and mass spectra of the degradation products confirm the structure previously assigned to hildecarpin.

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 preàlablement assigner à hildecarpin.

Keywords

HildecarpinpterocarpanflavonoidisoflavonoidTephrosia hildebrandtiiantifeedantantifungalMaruca testulalisHildecarpinpterocarpanflavonoidisoflavonoidTephrosia hildebrandtiiantiparasitaireantimycosiaueMaruca testulalis
Type
Research Articles
Information
International Journal of Tropical Insect Science , Volume 7 , Issue 4 , August 1986 , pp. 501 - 503
Copyright
Copyright © ICIPE 1986

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References

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