Abstract
Four new polyoxygenated briarane-type diterpenoids, briaexcavatolides O-R (1-4), have been isolated from a gorgonian octocoral Briareum excavatum. Their structures were determined using spectroscopic and chemical methods. Metabolites 1-3 were found to contain oxygenated substituents at C-2, C-3, and C-4, and the relative configurations were assigned as 2R*,3R*,4R* at these three positions. Briaranes containing this type of stereochemistry are reported for the first time. The structures of metabolites 1 and 2 were further confirmed by single-crystal X-ray analyses. Compound 2 has been shown to exhibit significant cytotoxicity toward P-388 and HT-29 cancer cells.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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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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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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Cnidaria / chemistry*
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Colonic Neoplasms
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Crystallography, X-Ray
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Diterpenes / chemistry
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Diterpenes / isolation & purification*
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Diterpenes / pharmacology
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Drug Screening Assays, Antitumor
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Humans
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Leukemia, Lymphoid
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Lung Neoplasms
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Mice
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Stereoisomerism
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Taiwan
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Tumor Cells, Cultured / drug effects
Substances
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Antineoplastic Agents
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Antineoplastic Agents, Phytogenic
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Diterpenes