Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Amino Acids / analysis
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Amino Acids / chemistry*
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Amino Acids / metabolism
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Animals
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Chromatography, High Pressure Liquid
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Coleoptera / chemistry*
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Coleoptera / metabolism
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Gas Chromatography-Mass Spectrometry
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Isomerism
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Molecular Structure
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Polyamines / analysis
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Polyamines / chemistry*
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Polyamines / isolation & purification
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Polyamines / metabolism
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Polyesters / analysis
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Polyesters / chemistry
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Polyesters / metabolism
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Pupa / chemistry
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Pupa / metabolism
Substances
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Amino Acids
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Polyamines
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Polyesters