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

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

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

Ding Luo et al. Front Chem. .

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.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

FIGURE 1
FIGURE 1
Chemical structures of compounds 1–4.
FIGURE 2
FIGURE 2
Key 1H−1H COSY and HMBC correlations of 1–4.
FIGURE 3
FIGURE 3
X-ray ORTEP drawings of 1 (A) and 3 (B).
FIGURE 4
FIGURE 4
Key NOESY correlations of 2 (A) and 4 (B).
FIGURE 5
FIGURE 5
Experimental ECD and calculated spectra of 2 and 4 at the B3LYP/6–31+G (d) level [2: σ = 0.30 eV, UV shift = −5 nm; 4: σ = 0.30 eV, UV shift = −6 nm].

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