Citation: Shuanggang Ma, Rubing Wang, Rongmei Gao, Xiaojing Wang, Yunbao Liu, Yong Li, Li Li, Yuhuan Li, Jing Qu, Shishan Yu. Antiviral spirooliganones C and D with a unique spiro[bicyclo[2.2.2]octane-2, 2′-bicyclo[3.1.0]hexane] carbon skeleton from the roots of Illicium oligandrum[J]. Chinese Chemical Letters, ;2022, 33(9): 4248-4252. doi: 10.1016/j.cclet.2022.02.050 shu

Antiviral spirooliganones C and D with a unique spiro[bicyclo[2.2.2]octane-2, 2′-bicyclo[3.1.0]hexane] carbon skeleton from the roots of Illicium oligandrum

Shuanggang Ma ^{a, 1,} ,
Rubing Wang ^{a, 1} ,
Rongmei Gao ^b ,
Xiaojing Wang ^a ,
Yunbao Liu ^a ,
Yong Li ^a ,
Li Li ^a ,
Yuhuan Li ^b ,
Jing Qu ^{a, *,} ,
Shishan Yu ^{a, *,}

a.
State Key Laboratory of Bioactive Sub stance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

mashuanggang@imm.ac.cn

qujing@imm.ac.cn

yushishan@imm.ac.cn

Received Date: 25 November 2021
Revised Date: 17 February 2022
Accepted Date: 18 February 2022
Available Online: 22 February 2022

Figures(7)

Two unprecedented polycyclic spirooliganones C and D (1 and 2) with a novel spiro[bicyclo[2.2.2]octane-2, 2′-bicyclo[3.1.0]hexane] carbon skeleton, one known dimeric prenylated C₆C₃ compound (3), and a pair of new enantiomeric prenylated C₆C₃ compounds (+)-5 and (−)-5 together with their direct precursors (+)-4 and (−)-4 were isolated from the roots of Illicium oligandrum. Their structures and absolute configurations were elucidated by spectroscopic analysis, single crystal X-ray diffraction data, and electronic circular dichroism calculations. A possible biosynthetic pathway for compounds 1 and 2 involving the Diels-Alder reaction between (−)-sabinene and cyclic prenylated tetrahydropyrano-type C₆C₃ compounds was proposed. The characteristic prenylated C₆C₃ compounds (+)-4 and (−)-4 were separated on a chiral stationary phase and their absolute configurations were determined by calculated ECD for the first time. In the antiviral bioassays, compounds 1 and (+)-5 exhibited significant inhibitory activity against CVB3 with IC₅₀ values of 11.11 µmol/L and 1.11 µmol/L, respectively. Compounds 1 and 2 also showed moderate inhibition against influenza A (H1N1) virus.
- Illicium,
- Illicium oligandrum,
- Spirooliganone,
- Prenylated C₆-C₃ compound,
- Antiviral activity
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