Abstract
Two new compounds, 3-amino-7,8-dihydroimidazo-[1,5-c]-pyrimidin-5(6H)-one (1) and ethyl 3-(2-amino-1H-imidazol-4-yl)propylcarbamate (2), along with the previously known 7,8-dihydroimidazo-[1,5-c]-pyrimidin-5(6H)-one (3), aeroplysinin-1 (4), dibromoverongiaquinol (5), bisoxazolidinone derivative (6), aerophobins-1 (7) and -2 (8), purealidins J (9) and L, have been isolated from Aplysina sp. from the South China Sea. The structures were elucidated on the basis of 1H, 13C NMR, MS and IR analyses. The histamine-derived alkaloids 1-3 may be unknown bioconversion products of purealidin J (9), aerophobin-2 (8) and aerophobin-1 (7), respectively, when 7-9 are cleaved at C-8-C-9 in reactions of activated chemical defense in Aplysina sponge.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Carbamates / chemistry*
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Carbamates / isolation & purification
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Chromatography, Thin Layer
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Histamine / analogs & derivatives*
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Histamine / chemistry*
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Histamine / isolation & purification
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Imidazoles / chemistry*
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Imidazoles / isolation & purification
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Indicators and Reagents
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Porifera / chemistry*
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Pyrimidinones / chemistry*
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Pyrimidinones / isolation & purification
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Spectrometry, Mass, Electrospray Ionization
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Spectrophotometry, Infrared
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Tyrosine / analogs & derivatives*
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Tyrosine / chemistry*
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Tyrosine / isolation & purification
Substances
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3-amino-7,8-dihydroimidazo-(1,5-c)-pyrimidin-5(6H)-one
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Carbamates
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Imidazoles
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Indicators and Reagents
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Pyrimidinones
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ethyl 3-(2-amino-1H-imidazol-4-yl)propylcarbamate
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Tyrosine
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Histamine