Abstract
Five new D-ring-opened phragmalin-type limonoids, tabulalins A-E (1-5, resp.), were isolated from the stem bark of Chukrasia tabularis var. velutina. In the structures of these new isolates, the D-ring (C(16)/C(17) δ-lactone ring) of phragmalins was cleaved, and rare C(16)/C(30) δ-lactone ring in 1-3 or C(16)/C(8) γ-lactone ring in 4 and 5 were formed. The structures of these new compounds were elucidated based on extensive 1D- and 2D-spectroscopic analyses (HSQC, HMBC, and ROESY) and HR-ESI-MS. The major compounds, 2, 3, and 5, were evaluated for their inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in a macrophage (RAW264.7) cell line with IC(50) values of 15.3±0.6, 13.0±0.5, and 17.1±0.7 μM, respectively.
Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anti-Inflammatory Agents, Non-Steroidal / chemistry*
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Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology
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Anti-Inflammatory Agents, Non-Steroidal / toxicity
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Cell Line
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Cell Survival / drug effects
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Drugs, Chinese Herbal / chemistry*
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Drugs, Chinese Herbal / isolation & purification*
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Lactones / chemistry
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Lactones / isolation & purification
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Limonins / chemistry*
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Limonins / isolation & purification
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Limonins / pharmacology
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Limonins / toxicity
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Macrophages / drug effects
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Macrophages / metabolism
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Magnetic Resonance Spectroscopy
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Meliaceae / chemistry*
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Mice
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Models, Molecular
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Molecular Structure
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Nitric Oxide / biosynthesis
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Plant Bark / chemistry
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Plant Stems / chemistry
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Spectrometry, Mass, Electrospray Ionization
Substances
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Anti-Inflammatory Agents, Non-Steroidal
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Drugs, Chinese Herbal
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Lactones
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Limonins
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Nitric Oxide