Isolation of macrocarpene-type sesquiterpenes from stigma maydis with neuroprotective activities

Wei-Yu Zhou; Bin Lin; Zi-Lin Hou; Shao-Chun Shi; Yu-Xi Wang; Xiao-Xiao Huang; Shao-Jiang Song

doi:10.1016/j.fitote.2019.104448

Isolation of macrocarpene-type sesquiterpenes from stigma maydis with neuroprotective activities

Fitoterapia. 2020 Mar:141:104448. doi: 10.1016/j.fitote.2019.104448. Epub 2019 Dec 6.

Authors

Wei-Yu Zhou¹, Bin Lin², Zi-Lin Hou¹, Shao-Chun Shi¹, Yu-Xi Wang¹, 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: 31816344
DOI: 10.1016/j.fitote.2019.104448

Abstract

Five undescribed macrocarpene-type sesquiterpenes (1-5), along with a known analogue (6) were isolated from the crude extract of stigma maydis. The structures of these compounds were elucidated based on comprehensive spectroscopic analyses together with quantum chemical calculations of ¹³C NMR data and electronic circular dichroism (ECD) curves. All isolated compounds were tested for their neuroprotective effects against the injury of human neuroblastoma SH-SY5Y cells induced by H₂O₂. Among them, compounds 3 (65.89%) and 5 (64.38%) showed moderate neuroprotective activity at 50 μM.

Keywords: Calculated ECD; DP4+; NMR calculations; Neuroprotective activities; Sesquiterpenes; Stigma maydis.

MeSH terms

Cell Line, Tumor
China
Drugs, Chinese Herbal / chemistry
Drugs, Chinese Herbal / isolation & purification
Drugs, Chinese Herbal / pharmacology
Flowers / chemistry*
Humans
Hydrogen Peroxide
Molecular Structure
Neuroblastoma / drug therapy
Neuroprotective Agents / chemistry
Neuroprotective Agents / isolation & purification*
Neuroprotective Agents / pharmacology*
Plant Extracts / chemistry
Plant Extracts / pharmacology*
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Sesquiterpenes / pharmacology*
Zea mays / chemistry*

Substances

Drugs, Chinese Herbal
Neuroprotective Agents
Plant Extracts
Sesquiterpenes
Hydrogen Peroxide