(R)-(+)-palasonin, a cantharidin-related plant toxin, also occurs in insect hemolymph and tissues.
J Chem Ecol
; 28(7): 1315-27, 2002 Jul.
Article
en En
| MEDLINE
| ID: mdl-12199498
ABSTRACT
Gas chromatographic and mass spectroscopic analyses of extracts of cantharidin-containing meloid, clerid, and staphylinid beetles revealed the presence of minor to significant amounts of palasonin, previously only known from seeds and fruits of the Indian shrub Buteafrondosa (Leguminaceae). Unlike (S)-(-)-palasonin (> 99% ee) from B. frondosa, the insects produce palasonin of low ee with the (R)-(+)-enantiomer (0-50% ee) prevailing. The ee of palasonin from individual specimens of predatory insects (Trichodes apiarius), which acquire their chemical protection from cantharidin-producing insects, may vary considerably. The absolute configuration of (S)-(-)-palasonin, previously deduced from indirect chemical and spectroscopic methods, was confirmed by X-ray crystal structure analysis of a cyclic imide derived from (S)-(-)-palasonin and (S)-(-)- 1 -(4-nitrophenyl)-ethylamine.
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Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Escarabajos
/
Hidrocarburos Aromáticos con Puentes
/
Cantaridina
/
Compuestos Epoxi
/
Irritantes
/
Fabaceae
Límite:
Animals
Idioma:
En
Revista:
J Chem Ecol
Año:
2002
Tipo del documento:
Article
País de afiliación:
Alemania