Defensive 2-Alkylpyrrole Sulfamates from the Marine Annelid Cirriformia tentaculata

Three novel 2-alkylpyrrole sulfamates (1−3) were isolated from the marine worm Cirriformia tentaculata. The structures were elucidated by the interpretation of spectral data obtained on inseparable mixtures of the unstable compounds. This suite of metabolites deterred feeding by the generalist preda...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2003-08, Vol.66 (8), p.1110-1112
Main Authors: Barsby, Todd, Kicklighter, Cynthia E, Hay, Mark E, Sullards, M. Cameron, Kubanek, Julia
Format: Article
Language:English
Subjects:
2-alkylpyrrole sulfamate
2-n-Heptylpyrrole sulfamate
2-n-Hexylpyrrole sulfamate
2-n-Octypyrrole sulfamate
Alkanes - chemistry
Alkanes - isolation & purification
Alkanes - pharmacology
animal products
Animals
Annelida
Annelida - chemistry
Annelida and closely related phyla: sipuncula. Echiura. Nemertinea
antifeedants
Biological and medical sciences
carbon
Carratulidae
chemical structure
Cirriformia tentaculata
Feeding Behavior - drug effects
Fishes
Florida
Fundamental and applied biological sciences. Psychology
Invertebrates
Nuclear Magnetic Resonance, Biomolecular
predators
protons
pyrroles
Pyrroles - chemistry
Pyrroles - isolation & purification
Pyrroles - pharmacology
spectral analysis
sulfamates
sulfites
Sulfonic Acids - chemistry
Sulfonic Acids - isolation & purification
Sulfonic Acids - pharmacology
Thalassoma
Thalassoma bifasciatum
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Summary:Three novel 2-alkylpyrrole sulfamates (1−3) were isolated from the marine worm Cirriformia tentaculata. The structures were elucidated by the interpretation of spectral data obtained on inseparable mixtures of the unstable compounds. This suite of metabolites deterred feeding by the generalist predatory fish Thalassoma bifasciatum.
ISSN:0163-3864
1520-6025
DOI:10.1021/np030149z