Mono- and Dimeric Xanthones with Anti-Glioma and Anti-Inflammatory Activities from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722

Abstract

Seven new xanthones, diaporthones A−G (1−7), together with 13 known analogues, including five mono- (8−14) and six dimeric xanthones (15−20), were obtained from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HR-ESIMS). The absolute configurations of 1−7 were clearly identified by X-ray crystallographic analysis and calculation of the ECD Spectra. Compounds 15−20 showed significant anti-inflammatory activity with IC50 values between 6.3 and 8.0 μM. In addition, dimeric xanthones (15−20) showed selective cytotoxicity against T98G cell lines with IC50 values ranging from 19.5 to 78.0 μM.

Shikimate-Derived Meroterpenoids from the Ascidian-Derived Fungus Amphichorda felina SYSU-MS7908 and Their Anti-Glioma Activity

“…Amphicordin C (3) was isolated as a colorless solid. Its molecular formula was determined to be C 18 13 C NMR data of 3 (Table 1) indicated the presence of four methyls, two methylenes, three oxygenated methines, three oxygenated non-hydrogenated carbons, two carbonyl carbons, and four sp 2 olefinic carbons. The planar structure of 3 was determined by analysis of the 1 H− 1 H COSY and HMBC spectra (Figure 1).…”

“…13−15 To date, researchers have identified 39 anti-glioma active molecules from four genera of marine fungi (Halorosellinia, Xylaria, Diaporthe, Penicillium, Trichobotrys). These metabolites exhibit diverse chemical structures, including polyketides (anthraquinone derivative SZ-685C, 16 xyloketal B, 17 six dimeric xanthones, 18 and calyxanthone 19 ), alkaloids (pyrrocidines, trichobamide A, 20 pyrrospirones C−J, 21,22 penicipyrrodiether A, 23 penicipyrroether A, 21 questiomycin A, 24 and xanthocillin X 24 ), terpenoids (the sesquiterpenoid purpuride G 25 triterpenoid penidifarnesylin A 26 ), glycosylated alkylresorcinols (peniresorcinosides A−E 26 ), and a meroterpenoid (penipyridinone B 24 ). In our search for bioactive secondary metabolites from ascidian-derived fungi in the South China Sea, 18,20,27−30 we discovered that a culture extract of the fungus Amphichorda felina SYSU-MS7908 exhibited moderate cytotoxicity against U87-MG human glioma cells.…”

“…In our search for bioactive secondary metabolites from ascidian-derived fungi in the South China Sea, ,,− we discovered that a culture extract of the fungus Amphichorda felina SYSU-MS7908 exhibited moderate cytotoxicity against U87-MG human glioma cells. We report the isolation of nine shikimate-derived diisoprenyl-cyclohexene/ane-type meroterpenoids ( 1 – 9 ), including amphicordins A–D ( 1 – 4 ), from this strain, and further synthesized four derivatives ( 10 – 13 ) utilizing natural oxirapentyn B ( 6 ).…”

“…In recent years, marine fungi have become a significant source of new marine natural products, accounting for more than 40% of discoveries from 2018 to 2021. − As a result, exploring marine fungi has become an effective strategy for discovering lead compounds with potential anti-glioma properties. − To date, researchers have identified 39 anti-glioma active molecules from four genera of marine fungi ( Halorosellinia , Xylaria , Diaporthe , Penicillium , Trichobotrys ). These metabolites exhibit diverse chemical structures, including polyketides (anthraquinone derivative SZ-685C, xyloketal B, six dimeric xanthones, and calyxanthone), alkaloids (pyrrocidines, trichobamide A, pyrrospirones C–J, , penicipyrrodiether A, penicipyrroether A, questiomycin A, and xanthocillin X), terpenoids (the sesquiterpenoid purpuride G and the triterpenoid penidifarnesylin A), glycosylated alkylresorcinols (peniresorcinosides A–E), and a meroterpenoid (penipyridinone B).…”

Epigenetic Manipulation Induced Production of Immunosuppressive Chromones and Cytochalasins from the Mangrove Endophytic Fungus Phomopsis asparagi DHS-48

“…The colony growth, dry biomass, 1 H NMR, and HPLC chromatogram were detected under the cultivation with small molecule epigenetic modifiers, the DNMT inhibitor 5-aza, the HDAC inhibitor sodium butyrate, and a combination of these inhibitors at various concentrations. A follow-up fermentation of an optional modifier (50 µM sodium butyrate) led to the isolation of two new compounds, phaseolorin J ( 1 ) and phomoparagin D ( 5 ), along with nine known phaseolorin D ( 2 ) [ 49 ], chaetochromone B ( 3 ) [ 50 ], pleosporalin D ( 4 ) [ 51 ], cytochalasins J, J1, J2, J3, H ( 6 – 10 ) [ 31 ] and phomopchalasin D ( 11 ) [ 38 ]. Herein, we report the epigenetic manipulation of this fungus, and the isolation, structural determination, and bioactivity evaluation of the induced products ( Figure 1 ).…”