Abstract
Anmindenols A (1) and B (2), inhibitors of inducible nitric oxide synthase (iNOS), were isolated from a marine-derived bacterium Streptomyces sp. Their chemical structures were elucidated by interpreting various spectroscopic data, including IR, MS, and NMR. Anmindenols A and B are sesquiterpenoids possessing an indene moiety with five- and six-membered rings derived from isoprenyl units. The absolute configuration of C-4 in anmindenol B was determined by electronic circular dichroism (ECD) of a dimolybdenum complex. Anmindenols A (1) and B (2) inhibited nitric oxide production in stimulated RAW 264.7 macrophage cells with IC50 values of 23 and 19 μM, respectively.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Indenes / chemistry
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Indenes / isolation & purification*
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Indenes / pharmacology*
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Inhibitory Concentration 50
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Lipopolysaccharides / pharmacology
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Macrophages / drug effects
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Marine Biology
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Mice
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Molecular Structure
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NF-kappa B / metabolism
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Nitric Oxide / biosynthesis
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Nitric Oxide Synthase Type II / antagonists & inhibitors*
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Nuclear Magnetic Resonance, Biomolecular
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Sesquiterpenes / chemistry
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology*
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Streptomyces / chemistry*
Substances
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Indenes
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Lipopolysaccharides
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NF-kappa B
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Sesquiterpenes
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anmindenol A
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anmindenol B
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Nitric Oxide
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Nitric Oxide Synthase Type II