Chiral separation of sesquineolignans from the stems and leaves of Neoshirakia japonica

Hai-Yan Zhao; Shuang He; Qian Lan; Bao-Jun Su; Heng-Shan Wang; Dong Liang

doi:10.1016/j.phytochem.2023.113683

Chiral separation of sesquineolignans from the stems and leaves of Neoshirakia japonica

Phytochemistry. 2023 Jul:211:113683. doi: 10.1016/j.phytochem.2023.113683. Epub 2023 Apr 25.

Authors

Hai-Yan Zhao¹, Shuang He², Qian Lan², Bao-Jun Su², Heng-Shan Wang², Dong Liang³

Affiliations

¹ State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, PR China; College of Food and Biochemical Engineering, Guangxi Science & Technology Normal University, Laibin, 546199, PR China.
² State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, PR China.
³ State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, PR China. Electronic address: liangdong@mailbox.gxnu.edu.cn.

PMID: 37105349
DOI: 10.1016/j.phytochem.2023.113683

Abstract

Twelve pairs of sesquineolignan enantiomers (1a/1b-6a/6b and 1c/1d-6c/6d), including twenty one undescribed and three known (2b, 3b, and 4b) sesquineolignans were isolated from an ethanol extract of the stems and leaves of Neoshirakia japonica (Euphorbiaceae). The successful separation of twelve pairs of enantiomers with mirror image-like electronic circular dichroism (ECD) curves and opposite specific rotation values, as one of the most important steps in compound isolation, was carried out by chiral HPLC columns. The absolute configurations of all undescribed sesquineolignans were elucidated by comprehensive analysis of their experimental ECD spectra. The effects of all the isolates on antineuroinflammatory and radical scavenging activity were evaluated. Compared with the positive control minocycline (IC₅₀ = 1.2 μM), compounds 1a/1b/1c/1d-6a/6b/6c/6d with IC₅₀ values being greater than 50 μM displayed almost no effect on the inhibition of NO production in LPS-induced BV-2 microglial cells. The results of DPPH-radical scavenging activity for them showed that compound 3c had moderate radical scavenging ability (EC₅₀ = 48.47 μM), while the EC₅₀ value of positive control vitamin C was 18.21 μM.

Keywords: Antineuroinflammatory activity; Chiral HPLC separation; Euphorbiaceae; Neoshirakia japonica; Radical scavenging activity; Sesquineolignans.

MeSH terms

Euphorbiaceae*
Microglia
Molecular Structure
Plant Leaves*