Abstract
Bioassay-directed fractionation of two southern Australian sponges, Phoriospongia sp. and Callyspongia bilamellata, yielded two new nematocidal depsipeptides, identified as phoriospongins A (1) and B (2). The structures of the phoriospongins were determined by detailed spectroscopic analysis and comparison with the previously reported sponge depsipeptide cyclolithistide A (3), as well as ESIMS and HPLC analysis of acid hydrolysates. It is noteworthy that the unique and yet structurally related metabolites 1-3 are found in sponges spanning three taxonomic orders, Poescilosclerida, Haplosclerida, and Lithistida.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amino Acids / analysis
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Animals
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Antinematodal Agents / chemistry
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Antinematodal Agents / isolation & purification*
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Antinematodal Agents / pharmacology
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Australia
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Chromatography, High Pressure Liquid
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Depsipeptides*
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Hydrolysis
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Peptides, Cyclic / chemistry
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Peptides, Cyclic / isolation & purification*
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Peptides, Cyclic / pharmacology
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Porifera / chemistry*
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Spectrometry, Mass, Electrospray Ionization
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Spectrophotometry, Infrared
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Valine / analogs & derivatives
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Valine / chemical synthesis
Substances
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Amino Acids
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Antinematodal Agents
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Depsipeptides
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Peptides, Cyclic
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phoriospongin A
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phoriospongin B
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Valine