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. 2023 Oct 19:14:1285243.
doi: 10.3389/fphar.2023.1285243. eCollection 2023.

Capparis cartilaginea decne (capparaceae): isolation of flavonoids by high-speed countercurrent chromatography and their anti-inflammatory evaluation

Bashaer Alsharif  1   2 , Nadhim Hante  1   3 , Bruna Govoni  4 , Hugo Verli  4 , Wirginia Kukula-Koch  5 , María Jose Santos-Martinez  1   6 , Fabio Boylan  1
Affiliations

Capparis cartilaginea decne (capparaceae): isolation of flavonoids by high-speed countercurrent chromatography and their anti-inflammatory evaluation

Bashaer Alsharif et al. Front Pharmacol. .

Abstract

Introduction: Capparis cartilaginea Decne. (CC) originates from the dry regions of Asia and the Mediterranean basin. In traditional medicine, tea of CC leaves is commonly used to treat inflammatory conditions such as rheumatism, arthritis, and gout. Due to the limited studies on the phytochemistry and biological activity of CC compared to other members of the Capparaceae family, this work aims to: 1) Identify the chemical composition of CC extract and 2) Investigate the potential anti-inflammatory effect of CC extract, tea and the isolated compounds. Methods: To guarantee aim 1, high-speed countercurrent chromatography (HSCC) method; Nuclear Magnetic Resonance (NMR) and High-Performance Liquid Chromatography coupled to Electrospray Ionisation and Quadrupole Time-of-Flight Mass Spectrometry (HPLC-ESIQTOF-MS/MS) were employed for this purpose. To guarantee aim 2, we studied the effect of the isolated flavonoids on matrix metalloproteinases (MMPs) -9 and -2 in murine macrophages. Molecular docking was initially performed to assess the binding affinity of the isolated flavonoids to the active site of MMP-9. Results and discussion: In silico model was a powerful tool to predict the compounds that could strongly bind and inhibit MMPs. CC extract and tea have shown to possess a significant antioxidant and anti-inflammatory effect, which can partially explain their traditional medicinal use.

Keywords: HSCCC; LC-MS; anti-inflammatory; capparis; flavonoids; virtual screening.

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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
HPLC-MS fingerprint of the CC total extract in the negative ionisation mode.
FIGURE 2
FIGURE 2
HSCCC Separation procedure of flavonoids from CC extract, followed by their purification using Sephadex LH-20.
FIGURE 3
FIGURE 3
Chemical compounds isolated from CC extract.
FIGURE 4
FIGURE 4
Determination of the antioxidant activity of CC extract and tea. (A) 1,1-Diphenyl-2-picrylhydrazyl (DPPH), radical scavenging assay; (B) 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonate) (ABTS) radical scavenging assay. Ascorbic acid was used as positive control.
FIGURE 5
FIGURE 5
Complexes obtained for compounds 8, 6 and 1 from docking calculations. The main interactions with MMP-9 amino acid residues are indicated. Red residues in (B, C) are common to the reference compound 8 (A).
FIGURE 6
FIGURE 6
Effect of CC tea, extract, and the isolated compounds on cell viability in RAW 264.7 macrophages. Data represent the mean ± SD of at least three independent experiments. One way ANOVA (p = 0.8575).
FIGURE 7
FIGURE 7
Modulation of MMP-9 activity in LPS stimulated macrophages. (A) Representative zymogram and statistical analysis on the effect of tea (T) and extract (E) on MMP 9. (B) Representative zymogram and statistical analysis on the effect of manghaslin (M) and rutin (R) on MMP9. (C) Representative zymogram and statistical analysis on the effect of Q3-Neo (Q) and clitorin (C) on MMP9. (D) Representative zymogram and statistical analysis on the effect of nicotiflorin (N) and K3-Neo (K) on MMP9. (E) Representative zymogram and statistical analysis on the effect of isorhamnetin-3-O-rutinoside (I) on MMP9. The relative activity of MMP-9 activity was quantified by densitometry and normalized to the values obtained in LPS treated cells. Each bar represents the mean ± SE of three independent experiments. One way ANOVA and Dunnett post-test; *p < 0.1 **p < 0.01, ***p < 0.001 vs LPS control.
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