Abstract
Fractionation of the crude methanol extract of the ascidian Cystodytes dellechiajei collected in Brazil yielded two novel alkaloids, sebastianine A (1) and sebastianine B (2). The structures of both 1 and 2 were established by analysis of spectroscopic data, indicating an unprecedented ring system for both compounds, comprising a pyridoacridine system fused with a pyrrole unit in sebastianine A (1) and a pyridoacridine system fused with a pyrrolidine system condensed with alpha-hydroxyisovaleric acid in sebastianine B (2). Both alkaloids displayed a cytotoxic profile against a panel of HCT-116 colon carcinoma cells indicative of a p53 dependent mechanism.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Acridines / chemistry
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Acridines / isolation & purification*
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Acridines / pharmacology
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Alkaloids / chemistry
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Alkaloids / isolation & purification*
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Alkaloids / pharmacology
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Animals
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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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Brazil
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Catalysis
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Cell Survival / drug effects
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Colonic Neoplasms
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Heterocyclic Compounds, 4 or More Rings / isolation & purification*
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Heterocyclic Compounds, 4 or More Rings / pharmacology
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Humans
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Inhibitory Concentration 50
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Pyridines / chemistry
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Pyridines / isolation & purification*
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Pyridines / pharmacology
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Tumor Cells, Cultured / drug effects
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Tumor Suppressor Protein p53 / metabolism
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Urochordata / chemistry*
Substances
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Acridines
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Alkaloids
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Antineoplastic Agents
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Heterocyclic Compounds, 4 or More Rings
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Pyridines
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Tumor Suppressor Protein p53
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sebastianine A
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sebastianine B