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]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
2. [2]
  Xu Huang , Kai-Yin Wu , Chao Su , Lei Yang , Bei-Bei Xiao . Metal-organic framework Cu-BTC for overall water splitting: A density functional theory study. Chinese Chemical Letters, 2025, 36(4): 109720-. doi: 10.1016/j.cclet.2024.109720
3. [3]
  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
4. [4]
  Qunlong Zhang , Jingyi Kang , Jingwen Wang , Tiancheng Tan , Zhaoyong Lu . Divergent total synthesis of sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G. Chinese Chemical Letters, 2025, 36(3): 109915-. doi: 10.1016/j.cclet.2024.109915
5. [5]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
6. [6]
  Wei-Yu Zhou , Zi-Han Xi , Ning-Ning Du , Li Ye , Ming-Hao Jiang , Jin-Le Hao , Bin Lin , Guo-Dong Yao , Xiao-Xiao Huang , Shao-Jiang Song . Rapid discovery of two unprecedented meroterpenoids from Daphne altaica Pall. using molecular networking integrated with MolNetEnhancer and Network Annotation Propagation. Chinese Chemical Letters, 2024, 35(8): 109030-. doi: 10.1016/j.cclet.2023.109030
7. [7]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2024.100277
8. [8]
  Qingyun Hu , Wei Wang , Junyuan Lu , He Zhu , Qi Liu , Yang Ren , Hong Wang , Jian Hui . High-throughput screening of high energy density LiMn_1-xFe_xPO₄ via active learning. Chinese Chemical Letters, 2025, 36(2): 110344-. doi: 10.1016/j.cclet.2024.110344
9. [9]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
10. [10]
  Haitao Yin , Liang Meng , Li Li , Jiamu Xiao , Longrui Liang , Nannan Huang , Yansong Shi , Angang Zhao , Jingwen Hou . Polydopamine-modified biochar supported polylactic acid and zero-valent iron affects the functional microbial community structure for 1,1,1-trichloroethane removal in simulated groundwater. Chinese Chemical Letters, 2025, 36(1): 110313-. doi: 10.1016/j.cclet.2024.110313
11. [11]
  Xiongbo Song , Jinwen Xiao , Juan Wu , Li Sun , Long Chen . Decellularized amniotic membrane promotes the anti-inflammatory response of macrophages via PI3K/AKT/HIF-1α pathway. Chinese Chemical Letters, 2025, 36(1): 109844-. doi: 10.1016/j.cclet.2024.109844
12. [12]
  Shaohua Zhang , Liyao Liu , Yingqiao Ma , Chong-an Di . Advances in theoretical calculations of organic thermoelectric materials. Chinese Chemical Letters, 2024, 35(8): 109749-. doi: 10.1016/j.cclet.2024.109749
13. [13]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
14. [14]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
15. [15]
  Bingwei Wang , Yihong Ding , Xiao Tian . Benchmarking model chemistry composite calculations for vertical ionization potential of molecular systems. Chinese Chemical Letters, 2025, 36(2): 109721-. doi: 10.1016/j.cclet.2024.109721
16. [16]
  Haiyang Gu , Xiang Xu . Multicolor hybrid metal halides and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(9): 100352-100352. doi: 10.1016/j.cjsc.2024.100352
17. [17]
  Ran Cen , Yan-Yan Tang , Li-Xia Chen , Zhu Tao , Xin Xiao . A novel supramolecular assembly based on nor-seco-cucurbit[10]uril for spermine sensing and artificial light-harvesting. Chinese Chemical Letters, 2025, 36(1): 109744-. doi: 10.1016/j.cclet.2024.109744
18. [18]
  Yunfei Shen , Long Chen . Gradient imprinted Zn metal anodes assist dendrites-free at high current density/capacity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100321-100321. doi: 10.1016/j.cjsc.2024.100321
19. [19]
  Zhilong Xie , Guohui Zhang , Ya Meng , Yefei Tong , Jian Deng , Honghui Li , Qingqing Ma , Shisong Han , Wenjun Ni . A natural nano-platform: Advances in drug delivery system with recombinant high-density lipoprotein. Chinese Chemical Letters, 2024, 35(11): 109584-. doi: 10.1016/j.cclet.2024.109584
20. [20]
  Longsheng Zhan , Yuchao Wang , Mengjie Liu , Xin Zhao , Danni Deng , Xinran Zheng , Jiabi Jiang , Xiang Xiong , Yongpeng Lei . BiVO₄ as a precatalyst for CO₂ electroreduction to formate at large current density. Chinese Chemical Letters, 2025, 36(3): 109695-. doi: 10.1016/j.cclet.2024.109695

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(82)
HTML views(4)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142