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Meroterpenoids with Potent Immunosuppressive Activity from Fungus Bipolaris zeicola
Author(s) -
Liu Mengting,
Zhang Xueke,
Shen Ling,
Lin Shuang,
Ye Ying,
Qi Changxing,
Wang Jianping,
Hu Zhengxi,
Zhang Yonghui
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202100233
Subject(s) - chemistry , fungus , stereochemistry , concanavalin a , two dimensional nuclear magnetic resonance spectroscopy , absolute configuration , circular dichroism , biochemistry , in vitro , botany , biology
Main observation and conclusion Six new meroterpenoids, bipolarinoids A—F (1—6), and two known congeners (7—8) were isolated from a soil‐derived fungus Bipolaris zeicola . Their structures were elucidated based on extensive spectroscopic techniques (including HRESIMS and 1D and 2D NMR data), and the absolute configurations of 1—4 were further confirmed via single‐crystal X‐ray diffraction analysis and comparison of experimental electronic circular dichroism (ECD) data. Structurally, compound 1 represents the first case of cochlioquinone derivatives featuring a formaldehyde group at C‐11, and compound 3 features a rare amino group at C‐11. In the immunosuppressive activity assay, compounds 5—8 showed potent inhibitory activity against concanavalin A (ConA)‐induced T lymphocyte proliferation with IC 50 values of 78.3, 81.1, 48.3, and 48.0 nmol/L, respectively, which provided promising leads for designing and developing new immunosuppressive agents to treat auto‐immunological diseases.