Highly Substituted Phenol Derivatives with Nitric Oxide Inhibitory Activities from the Deep-Sea-Derived Fungus Trichobotrys effuse FS524.

Chemical investigation on EtOAc extract of the deep-sea-derived fungus Trichobotrys effuse FS524 resulted in the isolation of six new highly substituted phenol derivatives trieffusols A-F (1-6), along with ten known relative analogues (7-16). Their structures with absolute configurations were extensively characterized on the basis of spectroscopic data analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism (ECD) calculations. Structurally, trieffusols A and B shared an unprecedented ploy-substituted 9-phenyl-hexahydroxanthone skeleton with an intriguing 6-6/6/6 tetracyclic fused ring system, which were often encountered as significant moieties in the pharmaceutical drugs but rarely discovered in natural products. In the screening towards their anti-inflammatory activities of 1-6, trieffusols C and D exhibited moderate inhibitory activities against nitric oxide (NO) production in LPS-induced RAW 264.7 macrophages with IC50 values ranging from 51.9 to 55.9 μM.