Talaromyoxaones A and B: Unusual Oxaphenalenone Spirolactones as Phosphatase Inhibitors from the Marine-Derived Fungus SCSIO 41517.

J Org Chem

CAS Key Laboratory of Tropical Marine Bioresources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.

Published: September 2021

(+)- and (-)-talaromyoxaones A and B ( and , respectively), two new oxaphenalenone derivatives with a hemiacetal frame and an unprecedented spirolactone frame of a 2',3,4'-spiro[isobenzofuran-1,3'-pyran]-3-one unit that show biosynthetic enantiodivergence, and two new oxaphenalenone analogues (±)-11-apopyrenulin () and (+)- or (-)-abeopyrenulin () were isolated from the marine-derived fungus SCSIO 41517. Their structures were elucidated by spectroscopic analysis, single-crystal X-ray diffraction, and quantum chemical calculations of ECD spectra. Compounds and showed selective inhibitory activity against phosphatases SHP1, SHP2, and MEG2 with IC values of 1.3-3.4 μM, and the potential modes of action for were investigated by a preliminary molecular docking study.

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http://dx.doi.org/10.1021/acs.joc.1c01452DOI Listing

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