Three new ent-eudesmane sesquiterpenoids, arundinols A–C (1–3), one isochroman-1-one, arundinone A (4), and a polyoxygenated benzofuran-3(2H)-one dimer, arundinone B (5), were isolated from the extract of a plant endophytic fungus, Microsphaeropsis arundinis. Their structures were elucidated primarily by NMR experiments, and 1 was confirmed by X-ray crystallography. The absolute configuration of 1 was assigned by X-ray crystallography using Cu Kα radiation, whereas those of the C-11 tertiary alcohols in 2 and 3 were deduced via the circular dichroism data of the in situ formed [Rh2(OCOCF3)4] complexes. Arundinone B (5) represents the first dimeric benzofuran-3(2H)-one, showing cytotoxicity against T24 and A549 cells. The co-isolated known compound 6 showed a modest inhibitory effect against Staphylococcus aureus.

Four new cyclic tetradecapeptides, verrucamides A–D (1–4), have been isolated from the solid-substrate fermentation culture of the ascomycete fungus Myrothecium verrucaria. The structures of these compounds, each featuring six N-methylated amino acid residues, were elucidated primarily by NMR and MS methods. The absolute configurations of 1–4 were assigned by application of Marfey’s method on their acid hydrolysates. Compounds 1–4 showed antimicrobial activity against the Gram-positive bacterium Staphylococcus aureus.

The new polyketides leptosphaerins A−G (1−7) and the known compounds monodictysin B (8), 2-(2,6-dihydroxybenzoyl)-3-hydroxy-5-methylbenzoic acid (9), and 2-(2,6-dihydroxy-4-methylbenzoyl)-6-hydroxybenzoic acid (10) have been isolated from solid cultures of the ascomycete fungus Leptosphaeria sp. The absolute configurations of compounds 1, 2, and 6 were assigned using the modified Mosher method, whereas that of C-2 in 3 was determined via the circular dichroism data of the [Rh2(OCOCF3)4] complex. Compound 7 showed antifungal activity against Aspergillus flavus.