Abstract
Two new highly polar brominated spiroisoxazolines, araplysillin N9-sulfamate (1) and an N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxy]-4-aminobutanoic acid (2), were isolated from a sample of Aplysina fulva collected in the Florida Keys. The absolute stereostructures of the new compounds were determined from analysis of MS, 1H and 13C NMR, and CD spectroscopy. Compound 2 provides a structural clue that may unify the biosynthesis of brominated spiroisoxazolines.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Animals
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Florida
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Hydrocarbons, Brominated / chemistry
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Hydrocarbons, Brominated / isolation & purification*
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Isoxazoles / chemistry
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Isoxazoles / isolation & purification*
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Porifera / chemistry*
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Spiro Compounds / chemistry
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Spiro Compounds / isolation & purification*
Substances
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Hydrocarbons, Brominated
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Isoxazoles
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N-((5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro(4.5)deca-2,6,8-triene-3-carboxy)-4-aminobutanoic acid
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Spiro Compounds
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araplysillin N9-sulfamate