Abstract
Five new cembranoids, namely, crassumolides A and B and D-F (1 and 2 and 4-6), along with four known metabolites, 7-10, were isolated from the soft coral Lobophytum crassum. Crassumolide C (3) was isolated for the first time from a natural source. The structures of these compounds were elucidated by extensive spectroscopic analysis and comparison of the NMR data with those of known analogues. The absolute stereochemistry of 1 was determined using the modified Mosher's method. Chemical transformation of 7 into the corresponding methyl ester 3 revealed the absolute stereochemistry of 3. Compounds 1, 3, and 7 were cytotoxic toward Ca9-22 cancer cells, and 10 was broadly cytotoxic toward all six test cancer cell lines used. Compounds 1, 3, 7, and 10 were found to inhibit the accumulation of the pro-inflammatory proteins iNOS and COX-2 at 10 μM.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anthozoa / chemistry*
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Anti-Inflammatory Agents / chemistry
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Anti-Inflammatory Agents / isolation & purification*
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Anti-Inflammatory 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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Cyclooxygenase 2 Inhibitors / chemistry
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Cyclooxygenase 2 Inhibitors / isolation & purification*
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Cyclooxygenase 2 Inhibitors / pharmacology*
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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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Lipopolysaccharides / pharmacology
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Macrophages / drug effects
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Molecular Structure
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Nitric Oxide Synthase Type II / antagonists & inhibitors
Substances
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Anti-Inflammatory Agents
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Antineoplastic Agents
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Cyclooxygenase 2 Inhibitors
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Diterpenes
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Lipopolysaccharides
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Nitric Oxide Synthase Type II