Abstract
Two new dammarane triterpenes have been isolated from the aerial parts of Ibicella lutea, 3-acetyl-24-epi-polacandrin (1) and 1,3-diacetyl-24-epi-polacandrin (2), and were obtained along with the known compounds 20S,24S-epoxy-3beta,12beta,25-trihydroxydammarane (3) and apigenin. The structures of compounds 1 and 2 were deduced by spectroscopic studies and by chemical transformations leading to the preparation of derivatives 4-11. The structure and relative stereochemistry of 1 were verified by single-crystal X-ray analysis. The natural compounds and selected semisynthetic derivatives were evaluated against several tumor cells.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylation
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification*
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Antineoplastic Agents, Phytogenic / pharmacology
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Argentina
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Cell Line, Tumor
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Crystallography, X-Ray
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Dammaranes
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Drug Screening Assays, Antitumor
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Humans
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Plants, Medicinal / chemistry*
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Stereoisomerism
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Triterpenes / chemistry
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Triterpenes / isolation & purification*
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Triterpenes / pharmacology
Substances
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1,3-diacetyl-24-epi-polacandrin
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3-acetyl-24-epi-polacandrin
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Antineoplastic Agents, Phytogenic
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Triterpenes