Ten new meroterpenoids, bipolaquinones
A–J (1–10), and one known
congener, isocochlioquinone
F (11), were isolated and identified from the fermented
rice cultures of a soil-derived fungus, Bipolaris zeicola. The planar structures of 1–10 were
elucidated based on extensive spectroscopic analyses (including HRESIMS
and 1D and 2D NMR data), and their absolute configurations were determined
by single-crystal X-ray diffraction analyses, comparison of experimental
electronic circular dichroism (ECD) data, ECD calculations, and hydrolysis
reaction. The immunosuppressive activity assay revealed that compounds 2, 3, and 7–10 showed significant inhibitory activity against concanavalin A (ConA)-induced
T lymphocyte proliferation with IC50 values ranging from
4.1 to 9.4 μM, which furnished potential lead molecules for
the design and development of new immunosuppressants for treating
autoimmune-associated diseases.