Novel Harziane Diterpenes from Deep-Sea Sediment Fungus Trichoderma sp. SCSIOW21 and Their Potential Anti-Inflammatory Effects

Five undescribed harziane-type diterpene derivatives, namely harzianol K (1), harzianol L (4), harzianol M (5), harzianol N (6), harzianol O (7), along with two known compounds, hazianol J (2) and harzianol A (3) were isolated from the deep-sea sediment-derived fungus Trichoderma sp. SCSIOW21. The relative configurations were determined by meticulous spectroscopic methods including 1D, 2D NMR spectroscopy, and HR-ESI-MS. The absolute configurations were established by the ECD curve calculations and the X-ray crystallographic analysis. These compounds (1, and 4-7) contributed to increasing the diversity of the caged harziane type diterpenes with highly congested skeleton characteristics. Harzianol J (2) exhibited a weak anti-inflammatory effect with 81.8% NO inhibition at 100 mu M.