Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 1, Pages 300-306Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02679
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Funding
- National Key Research and Development Program of China [2018YFC0310900]
- National Natural Science Fund for Distinguished Young Scholars of China [81225023]
- National Natural Science Fund of China [41476121, U1605221, 81402844, 41576130, 81502936, 31600014, 81741151]
- National High Technology Research and Development Program of China (863 Project) [2013AA092902]
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A novel 8(14 -> 15)-abeo-ergostane-type steroid, asperflotone (1), and an ergostane steroid, asperfloroid (2), were isolated from the solid culture of Aspergillus flocculosus 16D-1. Their structures and absolute configurations were determined by high-resolution electrospray ionization mass spectrometry, 1D/2D NMR, X-ray crystallography, and quantum chemical calculations. Compound 1 is an unprecedented ergosteroid featuring a rearranged bicyclo[4.2.1]non-2-ene ring system that could result from a-ketol rearrangement during biosynthesis. Compounds 1 and 2 showed inhibitory activity toward IL-6 production in the induced THP-1 cells.
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