Citation: 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[J]. Chinese Chemical Letters, ;2024, 35(8): 109030. doi: 10.1016/j.cclet.2023.109030 shu

Rapid discovery of two unprecedented meroterpenoids from Daphne altaica Pall. using molecular networking integrated with MolNetEnhancer and Network Annotation Propagation

Wei-Yu Zhou ^a ,
Zi-Han Xi ^a ,
Ning-Ning Du ^a ,
Li Ye ^a ,
Ming-Hao Jiang ^a ,
Jin-Le Hao ^b ,
Bin Lin ^c ,
Guo-Dong Yao ^a ,
Xiao-Xiao Huang ^{a, *,} ,
Shao-Jiang Song ^{a, *,}

a.
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province, Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China
b.
Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China
c.
Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang 110016, China

xiaoxiao270@163.com

songsj99@163.com

Received Date: 28 June 2023
Revised Date: 29 August 2023
Accepted Date: 30 August 2023
Available Online: 3 September 2023

Figures(4)

Under the guidance of the approach which integrates molecular networking, MolNetEnhancer and Network Annotation Propagation (NAP), daphnaltaicanoids A and B (1 and 2) with unprecedented 9-oxa-tetracyclo[6.6.1.0^2,6.0^8,13]pentadecane and tetracyclo[5.3.0.1^2,5.2^4,11]tridecane central frameworks were isolated from Daphne altaica Pall., representing two types of unparalleled meroterpenoid cores. Their structures were elucidated by extensive spectroscopic analysis, nuclear magnetic resonance (NMR) calculations, DP4+ analysis and electronic circular dichroism (ECD) calculations. The plausible biosynthetic pathways for 1 and 2 were postulated. Biologically, 2 exerted potent neuroprotective activities which were superior to trolox at 12.5 and 25 µmol/L. Moreover, 1 and 2 exhibited more noticeable acetylcholinesterase inhibitory activities than donepezil. Molecular docking simulations were performed to explore the intermolecular interaction of compounds 1 and 2 with acetylcholinesterase. The bioactivity evaluation results highlight the prospects of 1 and 2 as a novel category of neurological agents.
- Daphne altaica Pall.,
- Molecular networking,
- MolNetEnhancer,
- NAP,
- Unprecedented meroterpenoid frameworks,
- Neuroprotective activities,
- Acetylcholinesterase inhibitors
1. [1]
  Y. Li, L. Zhang, W. Wang, et al., Bioorg. Chem. 128 (2022) 106106. doi: 10.1016/j.bioorg.2022.106106
2. [2]
  J.J. Zhao, S.Z. Du, K. Hu, et al., Chin. Chem. Lett. 34 (2023) 107737. doi: 10.1016/j.cclet.2022.08.017
3. [3]
  X.Y. Hu, X.M. Li, S.Q. Yang, et al., Chin. Chem. Lett. 34 (2023) 107516. doi: 10.1016/j.cclet.2022.05.030
4. [4]
  Y. Ding, Y. Jiang, S.J. Xu, X.J. Xin, F.L. An, Chin. Chem. Lett. 34 (2023) 107562. doi: 10.1016/j.cclet.2022.05.076
5. [5]
  R. Taguchi, A. Iwasaki, A. Ebihara, et al., Org. Lett. 24 (2022) 4710–4714. doi: 10.1021/acs.orglett.2c02013
6. [6]
  J.H. Ye, G.Y. Luo, C.L. Zhao, et al., Chin. Chem. Lett. 34 (2023) 108621. doi: 10.1016/j.cclet.2023.108621
7. [7]
  Y.Y. Feng, S.Q. Zha, H.Q. Zhang, et al., Chin. Chem. Lett. 34 (2023) 107742. doi: 10.1016/j.cclet.2022.107742
8. [8]
  S.S. Chen, H.X. Liu, S.N. Li, et al., Chin. Chem. Lett. 34 (2023) 107513. doi: 10.1016/j.cclet.2022.05.027
9. [9]
  V.F. Freire, J.R. Gubiani, T.M. Spencer, et al., J. Nat. Prod. 85 (2022) 1340–1350. doi: 10.1021/acs.jnatprod.2c00094
10. [10]
  G. Cauchie, E.O. N'Nang, J.J.J. van der Hooft, et al., Org. Lett. 22 (2020) 6077–6081. doi: 10.1021/acs.orglett.0c02153
11. [11]
  J.X. Li, Z.R. Cui, Y.Y. Li, et al., Chin. Chem. Lett. 33 (2022) 4257–4260. doi: 10.1016/j.cclet.2022.01.084
12. [12]
  S. Lin, J.Z. Huang, H.X. Zeng, et al., Chin. Chem. Lett. 33 (2022) 4587–4594. doi: 10.1016/j.cclet.2022.03.064
13. [13]
  H. Gu, G.X. Dai, S.Y. Liu, et al., Chin. Chem. Lett. 34 (2023) 107715. doi: 10.1016/j.cclet.2022.07.058
14. [14]
  J.Y. Zhang, F. Liu, Q. Jin, et al., Chin. Chem. Lett. 35 (2024) 108881. doi: 10.1016/j.cclet.2023.108881
15. [15]
  A.E. Fox Ramos, C. Pavesi, M. Litaudon, et al., Anal. Chem. 91 (2019) 11247–11252. doi: 10.1021/acs.analchem.9b02216
16. [16]
  M.A. Beniddir, K.B. Kang, G. Genta-Jouve, et al., Nat. Prod. Rep. 38 (2021) 1967–1993. doi: 10.1039/d1np00023c
17. [17]
  M. Ernst, K.B. Kang, A.M. Caraballo-Rodríguez, et al., Metabolites 9 (2019) 144. doi: 10.3390/metabo9070144
18. [18]
  R.R. da Silva, M.X. Wang, L.F. Nothias, et al., PLoS Comput. Biol. 14 (2018) e1006089. doi: 10.1371/journal.pcbi.1006089
19. [19]
  K.B. Kang, E.J. Park, R.R. da Silva, et al., J. Nat. Prod. 81 (2018) 1819–1828. doi: 10.1021/acs.jnatprod.8b00292
20. [20]
  P. Zhao, Z.Y. Li, S.Y. Qin, et al., J. Org. Chem. 86 (2021) 15298–15306. doi: 10.1021/acs.joc.1c01880
21. [21]
  W.Y. Zhou, J.Y. Hou, Q. Li, et al., Phytochemistry 204 (2022) 113468. doi: 10.1016/j.phytochem.2022.113468
22. [22]
  S.H. Dong, Z.K. Duan, Y.F. Ai, et al., Bioorg. Chem. 129 (2022) 106208. doi: 10.1016/j.bioorg.2022.106208
23. [23]
  S.H. Mi, P. Zhao, Q. Li, et al., Phytochemistry 198 (2022) 113144. doi: 10.1016/j.phytochem.2022.113144
24. [24]
  Z.H. Chen, D.D. Yu, C. Li, et al., Chemistry 29 (2023) e202203487. doi: 10.1002/chem.202203487
25. [25]
  W.Y. Zhou, J.Q. Niu, Q. Li, et al., J. Agric. Food. Chem. 71 (2023) 3338–3349. doi: 10.1021/acs.jafc.2c08452
26. [26]
  R. Geris, T.J. Simpson, Nat. Prod. Rep. 26 (2009) 1063–1094. doi: 10.1039/b820413f
27. [27]
  H.W. Yan, R.R. Du, X. Zhang, et al., Chin. Chem. Lett. 33 (2022) 2555–2558. doi: 10.1016/j.cclet.2021.09.064
28. [28]
  C.L. Xie, D. Zhang, K.Q. Guo, et al., Chin. Chem. Lett. 33 (2022) 2057–2059. doi: 10.1016/j.cclet.2021.09.073
29. [29]
  T.M. Lv, D.L. Chen, J.J. Liang, et al., Org. Lett. 23 (2021) 7231–7235. doi: 10.1021/acs.orglett.1c02626
30. [30]
  J.J. Liang, T.M. Lv, Z.Y. Xu, et al., Fitoterapia 165 (2023) 105400. doi: 10.1016/j.fitote.2022.105400
31. [31]
  X. Wang, F.J. Liu, T. Xu, Chin. Chem. Lett. 34 (2023) 107624. doi: 10.1016/j.cclet.2022.06.047
32. [32]
  P.Y. Yang, Q. Jia, S.J. Song, X.X. Huang, Nat. Prod. Rep. 40 (2023) 1094–1129. doi: 10.1039/d2np00034b
33. [33]
  X.L. Qi, Y.Y. Zhang, P. Zhao, et al., J. Nat. Prod. 81 (2018) 1225–1234. doi: 10.1021/acs.jnatprod.7b01017
34. [34]
  Q. Ren, W.Y. Zhao, S.C. Shi, et al., J. Nat. Prod. 82 (2019) 1510–1517. doi: 10.1021/acs.jnatprod.8b01049
35. [35]
  Y.L. Liu, G. Uras, I. Onuwaje, et al., Eur. J. Med. Chem. 235 (2022) 114305. doi: 10.1016/j.ejmech.2022.114305
36. [36]
  X.Y. Jiang, C. Liu, M.X. Zou, et al., Eur. J. Med. Chem. 223 (2021) 113663. doi: 10.1016/j.ejmech.2021.113663
37. [37]
  P. Wang, Y. Wang, P. Li, et al., Chin. Chem. Lett. 34 (2023) 107691. doi: 10.1016/j.cclet.2022.07.034
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4. [4]
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6. [6]
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8. [8]
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