Setosphlides A–D, New Isocoumarin Derivatives from the Entomogenous Fungus Setosphaeria rostrate LGWB-10

Abstract

Investigation of the entomogenous fungus Setosphaeria rostrate LGWB-10 from Harmonia axyridis led to the isolation of four new isocoumarin derivatives, setosphlides A–D (1–4), and four known analogues (5–8). Their planar structures and the relative configurations were elucidated by comprehensive spectroscopic methods. The absolute configurations of isocoumarin nucleus for 1–4 were elucidated by their ECD spectra. The C-10 relative configurations for the pair of C-10 epimers (1 and 2) were established by comparing the magnitude of the computed 13C NMR chemical shifts (Δδcalcd.) with the experimental 13C NMR values (Δδexp.) for the epimers. All of the isolated compounds (1–8) were evaluated for their cytotoxicities against four human tumor cell lines MCF-7, MGC-803, HeLa, and Huh-7. Graphic Abstract

Polyketide Derivatives from the Endophytic Fungus Phaeosphaeria sp. LF5 Isolated from Huperzia serrata and Their Acetylcholinesterase Inhibitory Activities

“…These compounds have exhibited a wide range of biological functions, including antifungal, anti-inflammatory, insecticidal, and hepatoprotective activities [ 20 ]. However, the determination of their absolute configuration becomes quite challenging due to the high degree of free rotation of the steric centers on the chain, with the side chains connected to the nuclei of isocoumarin derivatives [ 21 ]. In the present study, the structures and absolute configurations of polyketide derivatives isolated from Phaeosphaeria sp.…”

Anti-Inflammatory Properties of Oxygenated Isocoumarins and Xanthone from Thai Mangrove-Associated Endophytic Fungus Setosphaeria rostrata

“…(3R,4R)-4,8-dihydroxy-3-((R)-2-hydroxypentyl)-6,7-dimethoxyisochroman-1-one ( 6) was obtained as a major metabolite (0.4 g, 7.8%) from 5.14 g of a crude broth extract of the SDB medium (10 L). The structures of the known compounds were confirmed by comparing their physicochemical and NMR spectroscopic data with those previously reported [10][11][12].…”

Recent advances in the discovery, biosynthesis, and therapeutic potential of isocoumarins derived from fungi: a comprehensive update

“…Compounds 279–282 displayed no cytotoxicity against MCF-7, MGC-803, HeLa, and Huh-7 with IC 50 values >200 μM. 137…”