Combinatorial chemistry in insects: a library of defensive macrocyclic polyamines.
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.
Schröder
F C
FC
Department of Chemistry, Cornell University, Ithaca, NY 14853, USA. fs31@cornell.edu
Farmer
J J
JJ
Attygalle
A B
AB
Smedley
S R
SR
Eisner
T
T
Meinwald
J
J
D000596:Amino Acids / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D001517:Coleoptera / Q000737:chemistry* / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D011073:Polyamines / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D011091:Polyesters / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D011679:Pupa / Q000737:chemistry / Q000378:metabolism
D000596:Amino Acids; D011073:Polyamines; D011091:Polyesters