Dihydroisocoumarin Derivatives from Marine-Derived Fungal Isolates and Their Anti-inflammatory Effects in Lipopolysaccharide-Induced BV2 Microglia
- 14 December 2015
- journal article
- review article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 78 (12), 2948-2955
- https://doi.org/10.1021/acs.jnatprod.5b00614
Abstract
Chemical investigation of the EtOAc extracts of marine-derived fungal isolates Aspergillus sp. SF-5974 and Aspergillus sp. SF-5976 yielded a new dihydroisocoumarin derivative (1) and 12 known metabolites. The structures of the isolated metabolites were established by extensive spectroscopic analyses, including 1D and 2D NMR spectra and MS data. Among the metabolites, the absolute configuration of 5'-hydroxyasperentin (6) was determined by single-crystal X-ray diffraction analysis. The in vitro antineuroinflammatory effects of the metabolites were also evaluated in lipopolysaccharide (LPS)-stimulated microglial cells. Among the isolated metabolites, dihydroisocoumarin derivatives 1-6 (10-80 μM) were shown to inhibit LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production by suppressing the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2), respectively, in LPS-stimulated BV2 microglia. Further, 1 (20-80 μM) was found to suppress the phosphorylation of the inhibitor of nuclear factor kappa B-α (IκB-α), interrupt the nuclear translocation of nuclear factor kappa B (NF-κB), and decrease the activation of p38 mitogen-activated protein kinase (MAPK).Keywords
Funding Information
- Ministry of Oceans and Fisheries (PM14050)
This publication has 30 references indexed in Scilit:
- Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activitiesBioorganic & Medicinal Chemistry Letters, 2014
- Penicillinolide A: A New Anti-Inflammatory Metabolite from the Marine Fungus Penicillium sp. SF-5292Marine Drugs, 2013
- New Deoxyisoaustamide Derivative from the Marine-derived Fungus Penicillium sp. JF-72Bulletin of the Korean Chemical Society, 2013
- Secondary metabolites of fungi from marine habitatsNatural Product Reports, 2011
- Marine-derived fungi: a chemically and biologically diverse group of microorganismsNatural Product Reports, 2004
- Molecular mechanisms of macrophage activation and deactivation by lipopolysaccharide: roles of the receptor complexPharmacology & Therapeutics, 2003
- Inflammatory Neurodegeneration Mediated by Nitric Oxide, Glutamate, and MitochondriaMolecular Neurobiology, 2003
- Ecology and taxonomy of pathogenic aspergilliFrontiers in Bioscience-Landmark, 2003
- Immunomodulatory Constituents from an Ascomycete, Microascus tardifaciens.CHEMICAL & PHARMACEUTICAL BULLETIN, 1999
- Isocladosporin, a Biologically Active Isomer of Cladosporin from Cladosporium cladosporioidesJournal of Natural Products, 1993