Anti-Inflammatory Activity of Compounds Derived from Vitex rotundifolia

Abstract

The objective of this study is to describe the separation and identification of one new phenolic and 19 known compounds from Vitex rotundifolia. Their structures were determined based on spectroscopic (NMR, CD, and MS) data analysis or Mosher’s method, and were compared with those reported in the literature. These isolates were then evaluated for their anti-inflammatory and antioxidant activities based on the inhibition of nitric oxide (NO) and interleukin (IL)-8 production in lipopolysaccharide (LPS)-stimulated cells (RAW264.7 and HT-29) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, respectively. In the NO assay, compounds 12–14 showed strong inhibition with compounds 10 and 15 displaying significant inhibition. In the IL-8 assay, compounds 8, 9, 13, 14, 19, and 20 exhibited potential to inhibit IL-8 production and other compounds displayed moderate inhibition. An in silico docking approach also revealed strong binding affinities for protein–ligand complexes of these active compounds against IL-8 production. The docking results were correlated with the experimental data of the IL-8 assay. Thus, these active compounds should be considered as candidates for further in vivo studies. This study implies the potential of new and active chemicals isolated from V. rotundifolia and provides evidence to support the development of active fractions and constituents into functional products targeting inflammatory diseases the future.

Molecular Networking and Bioassay-Guided Preparation and Separation of Active Extract and Constituents from Vicia tenuifolia Roth

“…As a result, this active fraction was chosen for the isolation and identification of four phenolics, five alkaloids, and 13 flavonoid glycosides from the flowers of V. tenuifolia. Among isolates, vicia D (1) is a new compound, 6-methoxykaempferol 3-O-sophoroside (15) and diosmetin 7-O-(2 -apiosyl)-glucoside (22) were first reported NMR data from this study, and ferulic acid (2), trans-p-coumaroyl-D-glucopyranose (3), cis-p-coumaroyl-D-glucopyranose (4), L-tryptophan (5) and D-tryptophan (6), D-phenylalanine (7), L-phenylalanine (8), adenosine (9), afzelin (10), rhamnocitrin 3-O-glucoside (11), kaempferol 7-O-glucoside (12), kaempferol 3-O-(2 -O-β-D-glucopyranosyl)-α-L-rhamnopyranoside (13) [30], kaempferol 3-O-rutinoside ( 14), quercetin-3-O-rhamnoside (16), rutin (17), rhamnetin 3-O-rutinoside (18), 6 -acetylapiin (19), graveobioside A (20), and diosmetin 7-O-rutinoside (21), were isolated for the first time from this plant. All the isolated compounds exhibited some significant inhibition against inflammatory cytokines and mediators.…”

“…The DPPH and ABTS radical scavenging activities were performed by following our previous method [19].…”

“…The IL-8 production assay [19] was used on HT-29 cells (3 × 10 5 cells/well) in 96-well plates using an ELISA kit (BD OptEIATM, San Jose, CA, USA) following the manufacturer's instructions.…”

“…There were also other compounds that were isolated and identified as ferulic acid (2) [31], trans-p-coumaroyl-D-glucopyranose (3) [32], cis-p-coumaroyl-D-glucopyranose (4) [33], L-tryptophan (5), and D-tryptophan (6) [34], D-phenylalanine (7), L-phenylalanine (8), and adenosine (9) [35], Afzelin (10) [36], rhamnocitrin 3-O-glucoside (11) [37], kaempferol 7-O-glucoside ( 12) [38], kaempferol 3-O-(2″-O-β-D-glucopyranosyl)-α-L-rhamnopyranoside (13) [39], kaempferol 3-O-rutinoside ( 14) [40], quercetin-3-O-rhamnoside ( 16) [41], rutin (17) [42], rhamnetin 3-O-rutinoside (18) [43], 6″-acetylapiin (19) [11], graveobioside A (20) [44], and diosmetin 7-O-rutinoside ( 21) [45] by analysis of their spectroscopic data compared to those reported from literature (Figure 4).…”

Antioxidant and Anti-Inflammatory Capacities of Fractions and Constituents from Vicia tetrasperma

“…The above observation suggested that the docked ligand occupied the binding pocket of the iNOS structure. Moreover, the iNOS-compound complex showed additional interactions (Table 2) with active residues in the binding pocket of the iNOS protein (Figure 9) in which the amino acids GLU377, ARG381, and VAL352 are the important residues of the binding sites in the pocket [30][31][32]. In detail, the ligand was stabilized by the formation of 7 conventional hydrogen bonds with amino acids, including ARG199, ARG381, ASP382, ILE201, GLU377, GLY202, and TRO463 along with a hydrophobic interaction at VAL352.…”