Antiviral mono- and bis-prenylated C₆-C₃ derivatives from the roots of Illicium oligandrum

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• 作者：Shuang-Gang Ma^a ; Ya Gao^a ; Hui-Qiang Wang^b ; Li Li^a ; Yun-Bao Liu^a ; Jing Qu^a ; Yong Li^a ; Song Xu^a ; Hai-Ning Lv^a ; Yu-Huan Li^b ; Shi-Shan Yu^a ; ^{yushishan@imm.ac.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Illicium oligandrum ; Bis-prenylated C6&ndash ; C3 derivatives ; Prenylated C6&ndash ; C3 compounds ; Anti-Coxsackie B3 virus ; Anti-influenza virus A virus
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：2 June 2016
• 年：2016
• 卷：72
• 期：22
• 页码：3003-3013
• 全文大小：1072 K

文摘

Four new bis-prenylated C₆–C₃ derivatives, illioliganpyranones B–C (1 and 4) and illioliganfuranones E–F (3 and 5), and six new mono-prenylated C₆–C₃ compounds, illioliganfuranone G (2), illioliganfuranol A (6), illioliganpyranone D (7), illioliganones J–K (8 and 9), and illioliganpyranol A (10), were isolated from the CHCl₃ extract of Illicium oligandrum roots. The structures of 1–10 were determined through interpretation of their spectroscopic data, including 1D and 2D NMR, HRESIMS, and CD experimental results, and the modified Mosher's method. The structure of illioliganpyranone B (1) was confirmed by single-crystal X-ray diffraction analysis. Compounds 1 and 3–5 are the first examples of linear bis-prenylated C₆–C₃ derivatives featuring ether bond connectivity. The in vitro activity of these compounds was evaluated against Coxsackievirus B3 (CVB3) and influenza virus A/Hanfang/359/95 (H3N2). Compounds 1, 3–5 and 6 demonstrated potent antiviral activity against CVB3, with IC₅₀ values ranging from 3.70 to 11.11 μM and SI values ranging from 5.2 to 21.1, whereas compounds 6 and 7 were found to exhibit potent activity against influenza virus A H3N2 with IC₅₀ values of 5.55 and 2.24 μM and SI values of 18.0 and 8.6, respectively.