4.7 Article

Anti-Inflammatory Effects of Curvularin-Type Metabolites from a Marine-Derived Fungal Strain Penicillium sp SF-5859 in Lipopolysaccharide-Induced RAW264.7 Macrophages

Journal

MARINE DRUGS
Volume 15, Issue 9, Pages -

Publisher

MDPI
DOI: 10.3390/md15090282

Keywords

curvularin; type metabolites; marine-derived fungus; anti-inflammatory effects; nuclear factor kappa B

Funding

  1. Korea Polar Research Institute [PE17100]
  2. Korea Polar Research Institute of Marine Research Placement (KOPRI) [PE17100] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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Chemical study on the extract of a marine-derived fungal strain Penicillium sp. SF-5859 yielded a new curvularin derivative (1), along with eight known curvularin-type polyketides (2-9). The structures of these metabolites (1-9) were established by comprehensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). In vitro anti-inflammatory effects of these metabolites were evaluated in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Among these metabolites, 3-9 were shown to strongly inhibit LPS-induced overproduction of nitric oxide (NO) and prostaglandin E2 (PGE(2)) with IC50 values ranging from 1.9 mu M to 18.1 mu M, and from 2.8 mu M to 18.7 mu M, respectively. In the further evaluation of signal pathways involved in these effects, the most active compound, (10E, 15S)-10,11-dehydrocurvularin (8) attenuated the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) in LPS-stimulated RAW264.7 macrophages. Furthermore, compound 8 was shown to suppress the upregulation of pro-inflammatory mediators and cytokines via the inhibition of the nuclear factor-kappa B (NF-kappa B) signaling pathway, but not through the mitogen-activated protein kinase (MAPK) pathway. Based on the comparisons of the different magnitude of the anti-inflammatory effects of these structurally-related metabolites, it was suggested that the opening of the 12-membered lactone ring in curvularin-type metabolites and blocking the phenol functionality led to the significant decrease in their anti-inflammatory activity.

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