Abstract
Three new alkaloids, including auranomides A and B (1 and 2), a new scaffold containing quinazolin-4-one substituted with a pyrrolidin-2-iminium moiety, and auranomide C (3), as well as two known metabolites auranthine (4) and aurantiomides C (5) were isolated from the marine-derived fungus Penicillium aurantiogriseum. The chemical structures of compounds 1-3 were elucidated by extensive spectroscopic methods, including IR, HRESIMS and 2D NMR spectroscopic analysis. The absolute configurations of compounds 1-3 were suggested from the perspective of a plausible biosynthesis pathway. Compounds 1-3 were subjected to antitumor and antimicrobial screening models. Auranomides A-C exhibited moderate cytotoxic activity against human tumor cells. Auranomides B was the most potent among them with an IC(50) value of 0.097 μmol/mL against HEPG2 cells.
Keywords:
Penicillium aurantiogriseum; antitumor; marine-derived fungus; quinazolin-4-one.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemistry*
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Alkaloids / isolation & purification*
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Alkaloids / pharmacology
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification
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Anti-Bacterial Agents / pharmacology
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Antifungal Agents / chemistry
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Antifungal Agents / isolation & purification
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Antifungal Agents / pharmacology
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology
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Aquatic Organisms / chemistry*
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Biological Products / chemistry
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Biological Products / isolation & purification
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Biological Products / pharmacology
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Drug Screening Assays, Antitumor / methods
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Hep G2 Cells
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Humans
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K562 Cells
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Magnetic Resonance Spectroscopy / methods
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Penicillium / chemistry*
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Pyrrolidines / chemistry
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Pyrrolidines / isolation & purification
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Pyrrolidines / pharmacology
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Quinazolinones / chemistry
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Quinazolinones / isolation & purification
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Quinazolinones / pharmacology
Substances
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Alkaloids
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Anti-Bacterial Agents
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Antifungal Agents
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Antineoplastic Agents
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Biological Products
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Pyrrolidines
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Quinazolinones