Citation: Wu-Yang Liu, Xin-Xiang Lei, Wen-Ji Wang, Jun-Mian Tian, Yu-Qi Gao, Jin-Ming Gao. Hyperforatone A, the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol with a unique bicyclo[5.4.0]undecane core from Hypericum perforatum[J]. Chinese Chemical Letters, ;2025, 36(4): 110478. doi: 10.1016/j.cclet.2024.110478 shu

Hyperforatone A, the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol with a unique bicyclo[5.4.0]undecane core from Hypericum perforatum

Wu-Yang Liu ^a ,
Xin-Xiang Lei ^b ,
Wen-Ji Wang ^a ,
Jun-Mian Tian ^{a, *,} ,
Yu-Qi Gao ^{a, *,} ,
Jin-Ming Gao ^{a, *,}

a.
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A & F University, Yangling 712100, China
b.
School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China

tianjunmian@nwsuaf.edu.cn

gyq1225@nwu.edu.cn

jinminggao@nwsuaf.edu.cn

Received Date: 24 July 2024
Revised Date: 14 September 2024
Accepted Date: 19 September 2024
Available Online: 20 September 2024

Figures(8)

Hyperforatone A (1), the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol, possessed an unusual bicyclo[5.4.0]undecane skeleton bearing a 5/7/6/5 ring system, and two known biosynthetically related precursors (2 and 3) were isolated from Hypericum perforatum (St. John’s wort). The structure and absolute configuration were unambiguously confirmed by a combination of comprehensive spectroscopic data, computational methods including residual dipolar couplings (RDCs), and X-ray crystallography. Density functional theory (DFT) calculations revealed that the cationic cyclization reaction was key to proposed formation mechanism for hyperforatone A. Furthermore, in vitro and in vivo experiments demonstrated that compound 1 was a potential anti-neuroinflammatory agent.
- Hypericum perforatum,
- Meroterpenoids,
- 1,8-Seco PPAP,
- Density functional theory calculations,
- Anti-neuroinflammatory activity
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