Vibsane-type diterpenoids from Viburnum odoratissimum and their cytotoxic activities.

Shi-Fang Li, Xiao-Qi Yu, Ya-Ling Li, Ming Bai, Bin Lin, Guo-Dong Yao, Shao-Jiang Song

Journal: Bioorganic chemistry 2021;106():104498

PMID: 33272710

Full Text on Elsevier Science View on PubMed

Abstract

Seven new diterpenoids (1-7), including five 7-membered ring vibsane-type diterpenoids, vibsanolide A-E (1-5) and a pair of epimers of 14,15,16,17-tetranorvibsane-type diterpenoids possessing bicyclo[4.2.1]nonane moiety, vibsanolide F-G (6-7), together with twelve known analogues (8-19) were isolated from the crude extracts of the leaves of Viburnum odoratissimum using Small Molecule Accurate Recognition Technology (SMART). These structures including absolute configurations were elucidated by means of comprehensive analyses of spectroscopic data, as well as comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. These compounds were evaluated for their cytotoxic activities against A549 and HepG2 cells by MTT assay. The results showed that compound 2 exhibited potent cytotoxic activity against A549 cells with IC value of 1.11 μM. Further staining experiments indicated that 2 could promote apoptosis induction, enhance reactive oxygen species (ROS) level and attenuate mitochondrial membrane potential (MMP) in A549 cells. Taken together, these findings provided new insights into understanding the cytotoxic activity of vibsane-type diterpenoids and it is meaningful to further investigate the application potential of V. odoratissimum.

Address: Key Laboratory of Computational Chemistry Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.; School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.; Key Laboratory of Computational Chemistry Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: [email protected].; Key Laboratory of Computational Chemistry Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: [email protected].

DOI: 10.1016/j.bioorg.2020.104498

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MeSH Terms: Antineoplastic Agents, Phytogenic, Apoptosis, Cell Line, Tumor, Cell Proliferation, Diterpenes, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Humans, Molecular Structure, Plant Extracts, Reactive Oxygen Species, Structure-Activity Relationship, Viburnum