Proliferacorins A-M: Thirteen undescribed acorane sesquiterpenoids isolated from the fungus Fusarium proliferatum.

In this study, 13 previously undescribed acorane sesquiterpenoids, namely, proliferacorins A-M, were isolated from the solid fermentation of Fusarium proliferatum. Their structures and absolute configurations were confirmed via spectroscopic analyses, quantum-chemical NMR calculations with DP4+ probability analyses, ECD calculations and comparisons, and single-crystal X-ray diffraction techniques. Proliferacorins A-E (1-5) have a 7-oxa-tricyclo[6.3.1.01,5]tridecane decorated with a rare ether bridge between C-7 and C-11, while proliferacorin F (6) possesses a 7-oxa-tricyclic[6.4.0.01,5]dodecane skeleton with an unusual ether bond between C-6 and C-11. Proliferacorins C and D (3 and 4) are a pair of isomers at the carbon bridge between C-5 and C-7, whereas proliferacorins H and I (8 and 9) are a pair of spiro carbon isomers. All isolates were tested for their cytotoxic, anti-inflammatory, and immunosuppressive activities.

Enantiomeric α-pyrone derivatives with immunosuppressive activity from Talaromyces adpressus.

Five pairs of undescribed enantiomeric α-pyrone derivatives (±)-adprepyrones A-E (±1-±5), together with an unreported congener adprepyrone F (6), and 6-[(E)-3-Hydroxyprop-1-enyl]-4-methoxy-5-methyl-2-pyrone (7), recently reported as synthetic compound, were isolated from the fungus Talaromyces adpressus. Their structures with absolute configurations were elucidated by HRESIMS, 1D and 2D NMR, electronic circular dichroism calculations, and single-crystal X-ray diffraction analyses. (±)-Adprepyrone A (±1) possesses an unreported carbon skeleton formed by the fusion of an α-pyrone derivative with nicotinamide. Compounds (+)-2, (±)-4, (±)-5, and 7 showed moderate inhibitory activity against concanavalin A (ConA)-induced T lymphocyte proliferation with IC50 values ranging from 8.9 to 19.8 µM.