Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects

Ding Luo; Zhenchao Tu; Wenjing Yin; Chunlin Fan; Nenghua Chen; Zhongnan Wu; Weilong Ding; Yaolan Li; Guocai Wang; Yubo Zhang

doi:10.3389/fchem.2021.740421

Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects

Front Chem. 2021 Sep 15:9:740421. doi: 10.3389/fchem.2021.740421. eCollection 2021.

Authors

Ding Luo¹, Zhenchao Tu¹, Wenjing Yin², Chunlin Fan¹, Nenghua Chen¹, Zhongnan Wu¹, Weilong Ding², Yaolan Li¹, Guocai Wang¹, Yubo Zhang^{1

3}

Affiliations

¹ Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, China.
² Department of Neurosurgery, The First Affiliated Hospital of Jinan University, Guangzhou, China.
³ Guangdong Clinical Translational Center for Targeted Drug, Department of Pharmacology, School of Medicine, Jinan University, Guangzhou, China.

Abstract

Four new alkaloids (1-4) belonging to rare examples of bis-amide matrine-type were isolated from the seeds of sophora alopecuroides. Their structures including absolute configuration were determined by extensive spectroscopic analysis, electronic circular dichroism (ECD) interpretation, and X-ray diffraction crystallography. Chemically, bis-amide matrine-type alkaloids can provide new molecular template for structural modification. Compounds 3-4 displayed obvious anti-inflammatory effects based on the inhibition of two key pro-inflammatory cytokines [tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6)] in a dose-dependent manner, with IC50 values from 35.6 to 45.8 μm.

Keywords: Sophora alopecuroides; matrine-type alkaloids; structure elucidation; structure modification; water-soluble alkaloids.