American Chemical Society
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Antiviral Spirooliganones A and B with Unprecedented Skeletons from the Roots of Illicium oligandrum

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posted on 2016-02-18, 22:54 authored by Shuang-Gang Ma, Rong-Mei Gao, Yu-Huan Li, Jian-Dong Jiang, Ning-Bo Gong, Li Li, Yang Lü, Wen-Zhao Tang, Yun-Bao Liu, Jing Qu, Hai-Ning Lü, Yong Li, Shi-Shan Yu
Two novel spirooliganones A (1) and (2), a pair of spiro carbon epimers, with a rare dioxaspiro skeleton were isolated from the roots of Illicium oligandrum. The structures were fully determined by spectroscopic analysis and chemical methods, especially modified Mosher’s method, and X-ray diffraction analysis. Spirooliganone B was found to exhibit more potent activities against coxsackie virus B3 and influenza virus A (H3N2) (IC50 3.70–5.05 μM) than spirooliganone A. The biosynthetic pathway involving a hetero-Diels–Alder reaction of the epimers was proposed.