Mono- and Dimeric Naphthalenones from the Marine-Derived Fungus Leptosphaerulina chartarum 3608

Mar Drugs. 2018 May 21;16(5):173. doi: 10.3390/md16050173.

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

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Aquatic Organisms / chemistry*
  • Aquatic Organisms / growth & development
  • Aquatic Organisms / isolation & purification
  • Ascomycota / chemistry*
  • Ascomycota / growth & development
  • Ascomycota / isolation & purification
  • Cell Line, Tumor
  • China
  • Chromatography, High Pressure Liquid
  • Drug Discovery*
  • Echinodermata / growth & development
  • Echinodermata / microbiology
  • Humans
  • Macrophages / drug effects*
  • Macrophages / immunology
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Naphthalenes / pharmacology
  • Naphthols / chemistry
  • Naphthols / isolation & purification
  • Naphthols / pharmacology
  • Pacific Ocean
  • RAW 264.7 Cells
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism

Substances

  • 10-norparvulenone
  • Anti-Inflammatory Agents, Non-Steroidal
  • Naphthalenes
  • Naphthols
  • leptothalenone B