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Spiroseoflosterol, a Rearranged Ergostane-Steroid from the Fruiting Bodies of Butyriboletus roseoflavus

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journal contribution
posted on 23.04.2020, 15:34 by Li-Hua Su, Chang-An Geng, Tian-Ze Li, Xiao-Yan Huang, Yun-Bao Ma, Xue-Mei Zhang, Gang Wu, Zhu-Liang Yang, Ji-Jun Chen
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.