Prenylated C6–C3 derivatives from the stems and branches of Illicium ternstroemioides A. C. Smith with antiviral activity

• Published in: Phytochemistry (Oxford) 2021-12, Vol.192, p.112935-112935, Article 112935
• Main Authors: Zhang, Jian-Pei, Li, Wen-Rui, Wu, Shuo, Wang, Xiao-Jing, Wang, Ru-Bing, Li, Mi, Su, Guo-Zhu, Wang, Hai-Qiang, Yong, Jin-Yao, Yang, Jia, Li, Li, Li, Yu-Huan, Ma, Shuang-Gang
• Format: Article
• Language: English
• Subjects: Anti-coxsackie virus B3; Anti-influenza virus A; Illiciaceae; Illicium ternstroemioides A. C. Smith; Prenylated C6–C3 derivatives
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2021.112935

Thirteen compounds were isolated from the lipid-soluble extracts of Illicium ternstroemioides A. C. Smith, including eleven previously undescribed prenylated C6–C3 compounds, a previously undescribed prenylated C6–C3 derivative-abscisic acid ester hybrid, and a known compound (4S)-illicinone I. Their structures and configurations were mainly elucidated by spectroscopic analyses, CD experiments and X-ray crystallography. (2S,4R,11S)-4-O-methyl-12-chloroillifunone C, (2S,4R,11R)-2,3-dihydro-4-O-methyl illioliganfunone D, and illiternfunol A were found to exhibit weak activity against Coxsackievirus B3, with IC50 values ranging from 27.8 to 33.3 μM. Illiternone B exhibited more potent activities against Coxsackievirus B3 and influenza virus A than did its geometric isomer illiternone A, with IC50 values of 7.7 μM and 2.5 μM, respectively. None of these compounds displayed cytotoxic activities. Twelve undescribed prenylated C6–C3 derivatives were isolated from Illicium ternstroemioides A. C. Smith. Illiternfunone A (10) represents the first example of prenylated C6–C3 derivative-abscisic acid ester hybrid. Illiternone B (12) was found to exhibit potent activities against Coxsackie virus B3 and influenza virus A. [Display omitted] •Thirteen undescribed prenylated C6–C3 derivatives were isolated from Illicium ternstroemioides A. C. Smith.•Illiternone B was found to exhibit potent activities against coxsackie virus B3 and influenza virus A.•Illiternfunone A represents the first example of prenylated C6–C3 derivative-abscisic acid ester hybrid.