1H NMR-guided isolation of hasubanan alkaloids from the alkaloidal extract of Stephania longa

Jiao Xiao; Yingjie Wang; Yanqiu Yang; Jingyu Liu; Bin Lin; Yue Hou; Gang Chen; Ning Li

doi:10.1016/j.bioorg.2023.106717

¹H NMR-guided isolation of hasubanan alkaloids from the alkaloidal extract of Stephania longa

Bioorg Chem. 2023 Oct:139:106717. doi: 10.1016/j.bioorg.2023.106717. Epub 2023 Jul 11.

Authors

Jiao Xiao¹, Yingjie Wang², Yanqiu Yang³, Jingyu Liu³, Bin Lin⁴, Yue Hou³, Gang Chen⁵, Ning Li⁶

Affiliations

¹ School of Traditional Chinese Materia Medica, Key Laboratory of Innovative Traditional Chinese Medicine for Major Chronic Diseases of Liaoning Province, Key Laboratory for TCM Material Basis Study and Innovative Drug Development of Shenyang City, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
² School of Traditional Chinese Materia Medica, Key Laboratory of Innovative Traditional Chinese Medicine for Major Chronic Diseases of Liaoning Province, Key Laboratory for TCM Material Basis Study and Innovative Drug Development of Shenyang City, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
³ College of Life and Health Sciences, Northeastern University, Shenyang 110004, People's Republic of China.
⁴ School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
⁵ School of Traditional Chinese Materia Medica, Key Laboratory of Innovative Traditional Chinese Medicine for Major Chronic Diseases of Liaoning Province, Key Laboratory for TCM Material Basis Study and Innovative Drug Development of Shenyang City, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: chengang1152001@163.com.
⁶ School of Traditional Chinese Materia Medica, Key Laboratory of Innovative Traditional Chinese Medicine for Major Chronic Diseases of Liaoning Province, Key Laboratory for TCM Material Basis Study and Innovative Drug Development of Shenyang City, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: liningsypharm@163.com.

PMID: 37454495
DOI: 10.1016/j.bioorg.2023.106717

Abstract

¹H NMR-guided fractionation led to the isolation of 16 alkaloids from the alkaloidal extract of Stephania longa, including 11 new hasubanan alkaloids (1-11) and five known alkaloids (12-16). Interestingly, compounds 2 and 11 are typically considered protonated tertiary amine compounds, whereas compounds 1 and 10 are regarded as oxidized versions of the corresponding compounds. Their gross structures were determined through an extensive analysis of spectroscopic data (NMR (nuclear magnetic resonance) and HRESIMS (high resolution electrospray ionization mass spectroscopy)), and their absolute configurations were established by comparing their experimental and calculated electronic circular dichroism (ECD) spectra. The new (3) and a known (12) compounds in all isolates displayed stronger antineuroinflammatory effects (IC₅₀ values of 1.8 and 11.1 μM, respectively) than minocycline (IC₅₀ value of 15.5 μM) against NO production on LPS-activated BV2 cells.

Keywords: Anti-neuroinflammatory; Hasubanan alkaloids; Microglia; Nitric oxide; Stephania longa.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids* / chemistry
Alkaloids* / pharmacology
Antineoplastic Agents*
Magnetic Resonance Spectroscopy
Molecular Structure
Plant Extracts
Proton Magnetic Resonance Spectroscopy
Stephania* / chemistry

Substances

hasubanan
Alkaloids
Antineoplastic Agents
Plant Extracts