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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

REFERENCES

Bilton, J. N., Debnam, J. R. and Smith, I. M. (1976) 6a-Hydroxypterocarpans from red clover. Phytochemistry 15, 1411–1412.CrossRefGoogle Scholar
Ingham, J. L. (1976) Fungal modification of pterocarpan phytoalexins from Melilotus alba and Trifolium pratense. Phytochemistry 15, 1489–1495.CrossRefGoogle Scholar
Ingham, J. L. and Markham, K. R. (1980) Identification of the Erythrina phytoalexin Cristacarpin and a note on the chirality of other 6a-hydroxypterocarpans. Phytochemistry 19, 1203–1207.CrossRefGoogle Scholar
Ingham, J. L. and Markham, K. R. (1982) Tephrocarpin, a pterocarpan phytoalexin from Tephrosia bidwilli and a structure proposal for acanthocarpan. Phytochemistry 21, 2969–2972.CrossRefGoogle Scholar
Lwande, W., Hassanali, A., Njoroge, P. W., Bentley, M. D., Delle Monache, F. and Jondiko, J. I. (1985) A new 6a-hydroxypterocarpan with insect antifeedant and anti-fungal properties from the roots of Tephrosia hildebrandtii Vatke. Insect Sci. Applic. 6, 537–541.Google Scholar
Mabry, T. J. and Markham, K. R. (1975) Mass spectrometry of flavonoids. In The Flavonoids (Edited by Harborne, J. B., Mabry, T. J. and Mabry, H.), pp. 79–126. Chapman & Hall, London.Google Scholar
Pelter, A. P., Stainton, P. and Baker, M. (1965) Mass spectra of oxygen heterocycles. II Mass Spectra of some flavonoids. J. Heterocycl. Chem. 2, 262–271.CrossRefGoogle Scholar