Isolation and characterization of seven neovibsane-type diterpenoids from Viburnum odoratissimum and their neuroblastoma cell protective effects.

Tian-Ming Lv, Bin Lin, Guo-Dong Yao, Shao-Jiang Song, Xiao-Xiao Huang, Jin-Ling Han, Jia-Qi Niu, Jin-Le Hao

Journal: Phytochemistry 2024;220():113992

PMID: 38301947

Full Text on Elsevier Science View on PubMed

Abstract

Seven undescribed neovibsane-type diterpenoids (1-7) were isolated from the leaves of Viburnum odoratissimum. Their planar structures and relative configurations were elucidated based on a combination of 1D and 2D NMR analysis. The absolute configurations were confirmed by Rh(OCOCF)-induced ECD analysis and comparison of experimental and TDDFT-calculated ECD spectrum. Based on the empirical results of the ECD of in situ formed Rh-complexes, rapid determination of the absolute configuration of C-14 within vibsane-type diterpenoids was proposed. In addition, 3 exhibited a high neuroblastoma cell protective effect of 81.8 % at 50 μM (the control group showed a neuroblastoma cell protective effect of 56.2 % at 50 μM).

Address: 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, Liaoning, 110016, China.; Department of Pharmaceutics, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016, China.; Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang, Liaoning, 110016, China. Electronic address: [email protected].; 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, Liaoning, 110016, China; Basic Science Research Center Base (Pharmaceutical Science), Shandong province, Yantai University, Yantai, 264005, China. Electronic address: [email protected].

DOI: 10.1016/j.phytochem.2024.113992

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MeSH Terms: Viburnum, Molecular Structure, Diterpenes, Plant Leaves, Neuroblastoma