Anti-inflammatory phomalichenones from an endolichenic fungus Phoma sp.

Abstract

Four new compounds, phomalichenones A-D (1-4), and seven known compounds (5-11) were isolated from the cultures of an endolichenic fungus Phoma sp. EL002650. Their structures were determined by the analysis of their spectroscopic data (NMR and MS). Compounds 1 and 6 inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. In addition, compound 1 diminished the protein expression levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), and decreased the mRNA expression levels of pro-inflammatory cytokines, such as tumor necrosis factor-α (TNF-α), interleukin(IL)-1β, and IL-6.

Highly Substituted Phenol Derivatives with Nitric Oxide Inhibitory Activities from the Deep-Sea-Derived Fungus Trichobotrys effuse FS524

“…Trieffusol E was afforded as a colorless powder and possessed a molecular formula of C 13 H 14 O 4 based on the HRESIMS ion peak at m/z 235.0971 [M + H] + (calcd 235.0965). Analysis of the 1D (Table 3) and 2D NMR data of 5 showed great similarity to these of 4-hydroxy-6-methoxy-5-(1 -oxobutyl)benzo[b]dihydrofuran [18]. The main difference was that the two methylenes at C-10 and C-11 positions in the known compound were oxidized to be a disubstituted double bond in 5.…”

“…Therefore, in-depth chemical research on the MNPs would pave the way to providing potential model structures and precursor drugs for new drug developments. During our continuing research for structurally unique and biologically significant NPs from marine fungi [15][16][17], the fungus strain Trichobotrys effuse FS524, isolated from a sediment sample collecting at the South China Sea, attracted our attention, and chemical investigation of the strain resulted in the isolation of six new highly substituted phenol derivatives, trieffusols A-F (1-6), along with eleven known analogues ( Figure 1), including phomalone (7) [18], 2,4-dihydroxy-3-(2-hydroxyethyl)-6-methoxyphenyl)-3-hydroxybutan-1-one (8) [18], (E)-1-(2,4-dihydroxy-3-(2-hydroxyethyl)-6-methoxyphenyl)but-2-en-1-one (9) [18], deoxyphomalone (10) [18], phomalichenone A (11) [18], methylindole-3-acetate (12) [19], 3-indole acetic acid (13) [20], 4-methoxyphenylacetic acid (14) [21], papuline (15) [22], and stigmast-4-en-3-one (16) [23]. Furthermore, their structures with absolute configurations were successfully established with the aid of spectroscopic data analyses, single-crystal X-ray diffraction experiments, and ECD calculations.…”

Extracts ofFlavoparmeliasp. Inhibit Receptor Activator of Nuclear Factor-κB Ligand-Mediated Osteoclast Differentiation

“…[2324] Their metabolites have been studied to discover new bioactive compounds [2526] and their biological activity is also being revealed. [272829]…”

Endolichenic Fungal Community Analysis by Pure Culture Isolation and Metabarcoding: A Case Study of Parmotrema tinctorum

“…The diverse metabolites isolated from ELF include alkaloids [ 18 , 19 ], quinones [ 20 , 21 ], terpenes [ 22 ], and peptides [ 23 ]. Various substances produced by ELF have been reported to exhibit remarkable biological activities [ 16 ] including anti-cancer [ 24 ], anti-bacterial [ 25 , 26 ], anti-fungal [ 27 , 28 ], anti-inflammatory [ 29 ], and anti-oxidant [ 30 ] activities. Because of the wide range of secondary metabolites, ELF may play ecologically important roles in resistance to abiotic and biotic stresses and detoxification of substances that endolichenic bacteria secrete [ 12 , 31 ].…”