Enantiomeric 8,4'-type oxyneolignans from the root barks of Ailanthus altissima (Mill.) Swingle and their neuroprotective effects against H2O2-induced SH-SY5Y cells injury

Ye-Qing Du; Bin Lin; Zhi-Yang Yan; Zi-Lin Hou; Rui Guo; Ming Bai; Le Zhou; Xiao-Xiao Huang; Shao-Jiang Song

doi:10.1016/j.fitote.2019.104403

Enantiomeric 8,4'-type oxyneolignans from the root barks of Ailanthus altissima (Mill.) Swingle and their neuroprotective effects against H₂O₂-induced SH-SY5Y cells injury

Fitoterapia. 2019 Nov:139:104403. doi: 10.1016/j.fitote.2019.104403. Epub 2019 Oct 29.

Authors

Ye-Qing Du¹, Bin Lin², Zhi-Yang Yan¹, Zi-Lin Hou¹, Rui Guo¹, Ming Bai¹, Le Zhou¹, Xiao-Xiao Huang³, Shao-Jiang Song⁴

Affiliations

¹ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
² School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
³ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address: xiaoxiao270@163.com.
⁴ Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China. Electronic address: songsj99@163.com.

PMID: 31676396
DOI: 10.1016/j.fitote.2019.104403

Abstract

Ailanthus altissima Swingle is a deciduous tree, belonging to the Simaroubaceae family. Phytochemical investigation of the root barks of A. altissima showed the presence of eight pairs of enantiomeric 8,4'-type oxyneolignans (1a/1b-8a/8b) including nine undescribed compounds (1b, 2a, 3a/3b, 4a/4b, 5b, 7b, 8a). Their structures were elucidated by comprehensive spectroscopic analyses, and their absolute configurations were determined by comparison of the experimental and quantum chemical calculations of electronic circular dichroism (ECD) curves. In addition, their neuroprotective effects against H₂O₂-induced oxidative stress in human neuroblastoma SH-SY5Y cells were investigated. Among them, 4a, 4b, and 8b exhibited moderate neuroprotective activity.

Keywords: 8,4′-type oxyneolignans; Ailanthus altissima; Calculated ECD; Neuroprotective activity.

MeSH terms

Ailanthus / chemistry*
Cell Line, Tumor
China
Humans
Hydrogen Peroxide
Lignans / isolation & purification
Lignans / pharmacology*
Molecular Structure
Neuroblastoma
Neuroprotective Agents / isolation & purification
Neuroprotective Agents / pharmacology*
Oxidative Stress / drug effects*
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Plant Bark / chemistry
Plant Roots / chemistry
Stereoisomerism

Substances

Lignans
Neuroprotective Agents
Phytochemicals
Hydrogen Peroxide