RESUMEN

The pupal defensive secretion of the coccinellid beetle Epilachna borealis is composed principally of a combinatorial library of macrocyclic polyamines. These compounds constitute a previously unrecognized family of natural products, characterized by extremely large-ring lactonic structures derived from a small set of (2-hydroxyethylamino)alkanoic acids. The combinatorial assembly of these simple building blocks generates a high degree of structural diversity, which is further increased by slow, spontaneous intramolecular rearrangement of the macrocycles.

Asunto(s)

Aminoácidos/química , Escarabajos/química , Poliaminas/química , Aminoácidos/análisis , Aminoácidos/metabolismo , Animales , Cromatografía Líquida de Alta Presión , Escarabajos/metabolismo , Cromatografía de Gases y Espectrometría de Masas , Isomerismo , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Estructura Molecular , Poliaminas/análisis , Poliaminas/aislamiento & purificación , Poliaminas/metabolismo , Poliésteres/análisis , Poliésteres/química , Poliésteres/metabolismo , Pupa/química , Pupa/metabolismo