Sesquiterpenoids and γ-pyranone derivatives from the whole plant of Erigeron breviscapus and their neuroprotective effects

Shuang Han; Ying Liu; Zilin Hou; Xiujia Sun; Guodong Yao; Pinyi Gao; Lingzhi Li; Shaojiang Song

doi:10.1016/j.fitote.2019.104288

Sesquiterpenoids and γ-pyranone derivatives from the whole plant of Erigeron breviscapus and their neuroprotective effects

Fitoterapia. 2019 Oct:138:104288. doi: 10.1016/j.fitote.2019.104288. Epub 2019 Aug 6.

Authors

Shuang Han¹, Ying Liu¹, Zilin Hou¹, Xiujia Sun², Guodong Yao¹, Pinyi Gao³, Lingzhi Li⁴, Shaojiang Song⁵

Affiliations

¹ School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
² Shanghai Key Laboratory of Psychotic Disorders, Shanghai Mental Health Center, Shanghai Jiao Tong University School of Medicine, Shanghai, 200030, People's Republic of China.
³ School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; College of Pharmaceutical and Biotechnology Engineering, Institute of Functional Molecules, Shenyang University of Chemical Technology, 11 Street, Shenyang economic and Technological Development Zone, Shenyang 110142, People's Republic of China. Electronic address: gpy1982@126.com.
⁴ School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: lilingzhijessie@163.com.
⁵ School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: songsj99@163.com.

PMID: 31398450
DOI: 10.1016/j.fitote.2019.104288

Abstract

Four new sesquiterpenes (1-2, 6-7), a new pyranone glycoside (10) along with six known compounds, were isolated from the whole plant of Erigeron breviscapus. Their planar structures were elucidated using extensive spectroscopic analyses. Brevisterpene A (1) and brevisterpene B (2) were proved to be a pair of diastereomer followed by mixtures resolution using chiral HPLC. Their absolute configurations were determined by ECD calculation. The relative configuration of brevisnoside B (7) was elucidated by a combined analysis of NOESY spectrum and computation of ¹³C NMR chemical shifts, and determination of the absolute configurations of 6 and 7 assisted by optical rotation calculations. Compounds 1 and 2 displayed moderate neuroprotective effects against H₂O₂-induced damage in SH-SY5Y cells.

Keywords: ECD calculation; Erigeron breviscapus; Neuroprotective effect; Optical rotation calculation; Sesquiterpene.

MeSH terms

Cell Line
China
Erigeron / chemistry*
Humans
Molecular Structure
Neuroprotective Agents / isolation & purification
Neuroprotective Agents / pharmacology*
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Plant Components, Aerial / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*

Substances

Neuroprotective Agents
Phytochemicals
Sesquiterpenes