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
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