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Bipolaquinones A–J, Immunosuppressive Meroterpenoids from a Soil-Derived Bipolaris zeicola

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posted on 01.09.2021, 20:29 by Mengting Liu, Lianghu Gu, Ling Shen, Xueke Zhang, Shuang Lin, Ying Ye, Jianping Wang, Zhengxi Hu, Yonghui Zhang
Ten new meroterpenoids, bipolaquinones A–J (110), 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 110 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 710 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.