Abstract
Spirodactylone (1), a hexacyclic indolizidone alkaloid possessing a novel spiro ring system, was isolated from the marine sponge Dactylia sp. The structure was elucidated by extensive spectroscopic methods including application of the LR-HSQMBC NMR pulse sequence. Oxidative cyclization of denigrin B (2), an aryl-substituted 2-oxo-pyrroline derivative that was also isolated from the sponge extract, provided material identical to spirodactylone (1). This confirmed the assigned structure and provides insight into the probable biogenesis of 1.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, N.I.H., Intramural
MeSH terms
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Alkaloids / chemistry*
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Alkaloids / metabolism
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Animals
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Cyclization
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Indolizines / chemical synthesis
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Indolizines / chemistry*
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Oxidation-Reduction
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Polycyclic Compounds / chemical synthesis
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Polycyclic Compounds / chemistry*
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Porifera / chemistry*
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Porifera / metabolism
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Pyrroles / chemistry*
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Pyrroles / metabolism
Substances
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Alkaloids
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Indolizines
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Polycyclic Compounds
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Pyrroles
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denigrin B