Alkaloids with neuroprotective effects from the leaves of Isatis indigotica collected in the Anhui Province, China

Si-Fan Liu; Ying-Ying Zhang; Le Zhou; Bin Lin; Xiao-Xiao Huang; Xiao-Bo Wang; Shao-Jiang Song

doi:10.1016/j.phytochem.2018.02.016

Alkaloids with neuroprotective effects from the leaves of Isatis indigotica collected in the Anhui Province, China

Phytochemistry. 2018 May:149:132-139. doi: 10.1016/j.phytochem.2018.02.016. Epub 2018 Feb 28.

Authors

Si-Fan Liu¹, Ying-Ying Zhang¹, Le Zhou², Bin Lin³, Xiao-Xiao Huang⁴, Xiao-Bo Wang⁵, Shao-Jiang Song⁶

Affiliations

¹ School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; Chinese People's Liberation Army 210 Hospital, Dalian 116021, People's Republic of China.
² School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
³ School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, People's Republic of China.
⁴ School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; Chinese People's Liberation Army 210 Hospital, Dalian 116021, People's Republic of China. Electronic address: xiaoxiao270@163.com.
⁵ Chinese People's Liberation Army 210 Hospital, Dalian 116021, People's Republic of China. Electronic address: wxbbenson0653@sina.com.
⁶ School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: songsj99@163.com.

PMID: 29499466
DOI: 10.1016/j.phytochem.2018.02.016

Abstract

Six undescribed alkaloids, indiforine A-F, together with four known ones, were isolated from the leaves of Isatis indigotica Fortune. Their structures were elucidated on the basis of extensive spectroscopic analyses. The absolute configurations of indiforine A and B were determined by comparison of the experimental and calculated electronic circular dichroism spectra, as well as experimental and calculated optical rotations. The isolated alkaloids were evaluated for their neuroprotective activities against H₂O₂-induced cell injury in human neuroblastoma SH-SY5Y cells. The results showed that in H₂O₂-induced SH-SY5Y cell injury models, indiforine A and B exhibited potent neuroprotective activities. Further investigation of the most potent indiforine A by Hoechst 33258 staining and Annexin V/PI analysis demonstrated that it could protect SH-SY5Y cells from oxidative damage through inhibiting cell apoptosis.

Keywords: Alkaloids; Apoptosis; Cruciferae; Isatis indigotica fortune; Neuroprotective activity.

MeSH terms

Apoptosis / drug effects
China
Drugs, Chinese Herbal / chemistry
Drugs, Chinese Herbal / isolation & purification*
Drugs, Chinese Herbal / pharmacology*
Humans
Hydrogen Peroxide / pharmacology
Indole Alkaloids / chemistry
Indole Alkaloids / isolation & purification*
Indole Alkaloids / pharmacology
Isatis / chemistry*
Molecular Structure
Neuroprotective Agents / chemistry
Neuroprotective Agents / isolation & purification*
Neuroprotective Agents / pharmacology*
Plant Leaves / chemistry*
Plant Roots / chemistry

Substances

Drugs, Chinese Herbal
Indole Alkaloids
Neuroprotective Agents
Hydrogen Peroxide