Undescribed matrine-type alkaloids from Sophora alopecuroides with anti-inflammatory activity

Abstract

A phytochemical investigation on the alkaloid fractions of Sophora alopecuroides L. led to the production of 11 undescribed matrine-type alkaloids, sophaloseedlines I-S (1-11), 12 known analogs (12-23), and an unexpected artificial matrine-derived Al(III) complex (24). The corresponding structures were elucidated by the interpretation of spectroscopic analyses, quantum chemical calculation, and six instances (1-4, 18, and 24), verified by X-ray crystallography. The biological activities screening demonstrated that none of the isolates exhibited cytotoxicity against four human cancer cell lines (HepG2, A549, THP-1, and MCF-7) and respiratory syncytial virus (RSV) at 50 μM, while moderate anti-inflammatory activity with IC₅₀ value from 15.6 to 47.8 μM was observed. The key structure-activity relationships of those matrine-type alkaloids for anti-inflammatory effects have been summarized. In addition, the most potent 7-epi-sophoramine (19) and aluminum sophaloseedline T (24) could effectively inhibit the release of pro-inflammatory factors (TNF-α, IL-6, and IL-1β), as well as the expression of iNOS and COX-2 proteins.

Keywords: Al(III) complex; Anti-inflammatory; Fabaceae; Matrine-type alkaloids; Sophaloseedlines I−T; Sophora alopecuroides L.; X-ray diffraction.