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
1. [1]
  R. Ciochina, R.B. Grossman. Chem. Rev. 106 (2006) 3963–3986. doi: 10.1021/cr0500582
2. [2]
  X.W. Yang, R.B. Grossman, G. Xu, Chem. Rev. 118 (2018) 3508–3558. doi: 10.1021/acs.chemrev.7b00551
3. [3]
  Z.H. Xu, R.B. Grossman, Y.F. Qiu, et al., J. Nat. Prod. 85 (2022) 2845–2855. doi: 10.1021/acs.jnatprod.2c00888
4. [4]
  W.J. Lu, Y.Q. Zhang, Y.W. Li, et al., Chin. Chem. Lett. 33 (2022) 4121–4125. doi: 10.1016/j.cclet.2021.11.011
5. [5]
  R.D. Liu, Y.L. Su, J.B. Yang, et al., Phytochemistry 142 (2017) 38–50. doi: 10.1016/j.phytochem.2017.06.011
6. [6]
  S.S. Xie, C.X. Qi, Y.L. Duan, et al., Org. Chem. Front. 7 (2020) 1349–1357. doi: 10.1039/d0qo00259c
7. [7]
  Y.L. Hu, K. Hu, L.M. Kong, et al., Org. Lett. 21 (2019) 1007–1010. doi: 10.1021/acs.orglett.8b04022
8. [8]
  Y. Guo, N. Zhang, C. Chen, et al., J. Nat. Prod. 80 (2017) 1493–1504. doi: 10.1021/acs.jnatprod.6b01178
9. [9]
  H. Bridi, G. de. C. Meirelles, G.L. von Poser, Phytochemistry 155 (2018) 203–232. doi: 10.1016/j.phytochem.2018.08.002
10. [10]
  H.Y. Lou, F.W. Ma, P. Yi, et al., J. Arab. J. Chem. 15 (2022) 104057. doi: 10.1016/j.arabjc.2022.104057
11. [11]
  H.Y. Lou, Y.N. Li, P. Yi, et al., Org. Lett. 22 (2020) 6903–6906. doi: 10.1021/acs.orglett.0c02434
12. [12]
  C.M. Yuan, Y.R. Zeng, L. Huang, et al., Chin. Chem. Lett. (2024), https://doi.org/10.1016/j.cclet.2024.109859. doi: 10.1016/j.cclet.2024.109859
13. [13]
  Z.Y. Shi, J. Yin, Y. Xiao, et al., Chin. Chem. Lett. 35 (2024) 109458. doi: 10.1016/j.cclet.2023.109458
14. [14]
  X.T. Yan, Z. An, D. Tang, et al. RSC Adv. 8 (2018) 26646–26655. doi: 10.1039/c8ra05322g
15. [15]
  X.T. Yan, Z. An, Y. Huangfu, et al., Phytochemistry 159 (2019) 65–74. doi: 10.3390/membranes9050065
16. [16]
  J.Y. Xie, P.F. Li, X.T. Yan, et al. Commun. Chem. 7 (2024) 1. doi: 10.1038/s42004-023-01091-1
17. [17]
  X.T. Yan, J.X. Chen; Z.X. Wang, et al., J. Nat. Prod. 86 (2023) 119–130. doi: 10.1021/acs.jnatprod.2c00810
18. [18]
  J.Y. Xie, Z.X. Wang, W.Y. Liu, et al., J. Nat. Prod. 86 (2023) 1910–1918. doi: 10.1021/acs.jnatprod.3c00226
19. [19]
  L. Verotta, G. Appendino, J. Jakupovic, et al., J. Nat. Prod. 63 (2000) 412–415. doi: 10.1021/np9903752
20. [20]
  X.W. Yang, Y. Ding, J.J. Zhang, et al., Org. Lett. 16 (2014) 2434–2437. doi: 10.1021/ol500808p
21. [21]
  J.Q. You, Y.Q. Jin, M.Y. Li, et al., Chin. J. Chem. 42 (2024) 2180-2186. doi: 10.1002/cjoc.202400248
22. [22]
  W.B. Han, Y.J. Zhai, R. Zhang, et al., Angew. Chem. Int. Edit. 62 (2023) e202300773. doi: 10.1002/anie.202300773
23. [23]
  W.J. Xu, P.F. Tang, W.J. Lu, et al., Org. Lett. 21 (2019) 8558–8562. doi: 10.1021/acs.orglett.9b03098
24. [24]
  N.N. Jiang, Y.S. Ye, X. Liu, et al., Org. Lett. 25 (2024) 8965–8969.
25. [25]
  X.Y. Jia, Y.M. Wu, C. Lei, et al., Chin. Chem. Lett. 31 (2020) 1263–1266. doi: 10.1016/j.cclet.2019.10.014
26. [26]
  J.F. Zong, Z. Hu, Y.Y. Shao, et al., Org. Lett. 22 (2022) 2797–2800.
27. [27]
  Y.L. Duan, Y. Guo, Y.F. Deng, et al., J. Org. Chem. 87 (2022) 6824–6831. doi: 10.1021/acs.joc.2c00503
28. [28]
  C. Janine, Photoinduced electron tranfer in radical reactions, Vol. 1, in: R. Philippe, P.S. Mukund (Eds.), Radicals in Organic Synthesis, Wiley-Vch Press: Strauss Offsetdruck Gmbh Press, Mörlenbach, 2001, pp. 245.
29. [29]
  L. Canonica, B. Danieli, G. Lesma, et al., Helv. Chim. Acta 70 (1987) 701–716. doi: 10.1002/hlca.19870700320
30. [30]
  K. Cen, J.J. Bao, X.D. Wang, et al., J. Am. Chem. Soc. 146 (2024) 6481–6486. doi: 10.1021/jacs.4c01016
1. [1]
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2. [2]
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5. [5]
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8. [8]
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10. [10]
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11. [11]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
12. [12]
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13. [13]
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15. [15]
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18. [18]
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