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A novel 2,3-epoxy naphthoquinol, named (6 R ,7 R ,8 R )-theissenone A ( 1 ), possessing an oxatricyclo[5.4.0.0 3,5 ]undeca-trien-2-one skeleton, together with two known compounds, (6 S ,7 R ,8 R )-theissenone ( 2 ) and arthrinone ( 3 ), were produced by an endophytic fungus,  Arthrinium marii  M-211, which was isolated from mangrove plants. The structure of  1 , including the absolute stereochemistry, was elucidated by analysis of nuclear magnetic resonance (NMR) and mass spectrometry (MS) data and time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) spectra. Additionally, the absolute structure of  2  was deduced as a diastereomer of  1  using ECD spectral data analysis. Compounds  1 ,  2  and  3  exhibited cytotoxic activity against the H4IIE rat hepatoma cells, with IC 50  values of 67.5, 46.6 and 13.4 µM, respectively.

The 2,3-epoxy naphthoquinol produced by endophyte Arthrinium marii M-211