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Five novel tyrosine-decahydrofluorene analogues, xenoacremones D−H (1−5), each bearing a fused 6/5/6 tricarbocyclic core and a 13-membered para-cyclophane ring system, were isolated from the endophytic fungus Xenoacremonium sinensis. Compound 1 was a novel polyketide synthase−nonribosomal peptide synthetase (PKS−NRPS) tyrosine-decahydrofluorene hybrid containing a 6/5/6/6/5 ring system. Their structures were elucidated from comprehensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. All compounds were evaluated for their inhibitory activities on LPS-induced NO production in macrophages and their cytotoxicities against the NB4 and U937 cell lines. Compounds 3 and 5 exhibited potent anti-inflammatory activities in vitro. Compounds 1 and 3−5 displayed significant antiproliferative activity against the tumor cell lines (IC50 &lt; 20 µM).

Xenoacremones D–H, Bioactive Tyrosine-decahydrofluorene Analogues from the Plant-Derived Fungus Xenoacremonium sinensis