Abstract
A pair of new enantiomeric alkaloid dimers, (+)- and (-)-pestaloxazine A (1), with an unprecedented symmetric spiro[oxazinane-piperazinedione] skeleton, consisting of 22 carbons and 12 heteroatoms, were isolated from a Pestalotiopsis sp. fungus derived from a soft coral. Separation of the enantiomeric alkaloid dimers was achieved by chiral HPLC. Their structures including absolute configurations were elucidated on the basis of a comprehensive analysis of their spectroscopic and X-ray diffraction data and CD calculations. (+)-Pestaloxazine A exhibited potent antiviral activity against EV71 with an IC50 value of 14.2 ± 1.3 μM, which was stronger than that of the positive control ribavirin (IC50 = 256.1 ± 15.1 μM).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Alkaloids / isolation & purification
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Alkaloids / pharmacology
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / chemistry
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Antiviral Agents / isolation & purification
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Antiviral Agents / pharmacology
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Chromatography, High Pressure Liquid
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Enterovirus A, Human / drug effects
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Piperazines / chemical synthesis*
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Piperazines / chemistry
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Piperazines / isolation & purification
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Piperazines / pharmacology
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
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Spiro Compounds / isolation & purification
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Spiro Compounds / pharmacology
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Stereoisomerism
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Xylariales / chemistry
Substances
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Alkaloids
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Antiviral Agents
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Piperazines
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Spiro Compounds
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pestaloxazine A