Aspersecosteroids A and B, Two 11(9 → 10)-abeo-5,10-Secosteroids with a Dioxatetraheterocyclic Ring System from Aspergillus flocculosus 16D-1
2018
Gu, Bin-Bin | Wu, Wei | Jiao, Fu-Rong | Jiao, Wei-hua | Li, Lei | Sun, Fan | Wang, Shu-Ping | Yang, Fan | Lin, Hou-Wen
Two 11(9 → 10)-abeo-5,10-secosteroids possessing an unprecedented dioxatetraheterocyclic ring system, aspersecosteroids A (1) and B (2), and a new ergosteroid, asperflosterol (3), were isolated from the sponge-derived fungus Aspergillus flocculosus 16D-1. Their structures were determined by spectroscopic analysis, X-ray diffraction, and computational methods. Compounds 1–3 demonstrated inhibitory effects on key pro-inflammatory cytokine production in THP-1 cells. A biogenetic pathway with oxidative cleavage, Wagner–Meerwein rearrangement, and sequential acetalization as key steps is proposed for 1 and 2.
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