Spiroseoflosterol, a Rearranged Ergostane-Steroid from the Fruiting Bodies of <i>Butyriboletus roseoflavus</i>
Li‐Hua Su, Chang‐An Geng, Tian-Ze Li, Xiaoyan Huang, Yun‐Bao Ma, Xue‐Mei Zhang, Gang Wu, Zhu‐Liang Yang, Ji‐Jun Chen
Abstract
Spiroseoflosterol (1), a 7(8→9)-abeo-ergostane steroid with a unique spiro[4.5]decan-6-one system, was isolated from the fruiting bodies of Butyriboletus roseoflavus. Its structure was determined by interpretation of comprehensive spectroscopic, X-ray, and computational data. A plausible biogenetic pathway for spiroseoflosterol (1) was postulated based on a key semipinacol rearrangement. Compound 1 was cytotoxic to HepG2 and Huh7/S (sorafenib-resistant Huh7) with IC50 values of 9.1 and 6.2 μM, respectively.
Topics & Concepts
SteroidStereochemistrySorafenibBiologyChemistryGeneticsBiochemistryHormoneHepatocellular carcinomaPhytochemistry and Bioactive CompoundsMarine Sponges and Natural ProductsPhytochemical compounds biological activities