Abstract
Five new naphthalenones, two enantiomers (−)-1 and (+)-1 leptothalenone A, (−)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((−)-2), (4S, 10R, 4’S)-leptotha-lenone B (5), (4R, 10S, 4’S)-leptothalenone B (6), and a new isocoumarine, 6-hydroxy-5,8-dimethoxy-3-methyl-1H-isochromen-1-one (4), along with two known compounds (+)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((+)-2) and (+)-10-norparvulenone (3) were isolated from the marine-derived fungus Leptosphaerulina chartarum 3608. The structures of new compounds were elucidated by HR-ESIMS, NMR, and ECD analysis. All compounds were evaluated for cytotoxicity and anti-inflammatory activity. Compound 6 showed moderate anti-inflammatory activity by inhibiting the production of nitric oxide (NO) in lipopolysaccharide-stimulated RAW264.7 cells, with an IC50 value of 44.5 μM.
Keywords:
Leptosphaerulina chartarum; anti-inflammatory; isocoumarine; naphthalenones.
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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Aquatic Organisms / chemistry*
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Aquatic Organisms / growth & development
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Aquatic Organisms / isolation & purification
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Ascomycota / chemistry*
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Ascomycota / growth & development
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Ascomycota / isolation & purification
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Cell Line, Tumor
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China
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Chromatography, High Pressure Liquid
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Drug Discovery*
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Echinodermata / growth & development
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Echinodermata / microbiology
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Humans
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Macrophages / drug effects*
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Macrophages / immunology
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Macrophages / metabolism
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Magnetic Resonance Spectroscopy
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Mice
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Molecular Structure
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Naphthalenes / chemistry
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Naphthalenes / isolation & purification*
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Naphthalenes / pharmacology
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Naphthols / chemistry
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Naphthols / isolation & purification
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Naphthols / pharmacology
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Pacific Ocean
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RAW 264.7 Cells
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Spectrometry, Mass, Electrospray Ionization
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Stereoisomerism
Substances
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10-norparvulenone
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Anti-Inflammatory Agents, Non-Steroidal
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Naphthalenes
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Naphthols
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leptothalenone B