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Research Article | Open Access

Effective anti-inflammatory phenolic compounds from dandelion: identification and mechanistic insights using UHPLC-ESI-MS/MS, fluorescence quenching and anisotropy, molecular docking and dynamics simulation

Hui Zoua,1, Tingting Bena,1, Ping Wua, Geoffrey I.N. Waterhouseb( ), Yilun Chena( )
College of Food Science and Engineering, Shandong Agricultural University, Key Laboratory of Food Processing Technology and Quality Control in Shandong Province, Tai’an 271018, China
School of Chemical Sciences, University of Auckland, Auckland 1142, New Zealand

1 These authors contributed equally to this work and should be considered co-first authors.

Peer review under responsibility of KeAi Communications Co., Ltd.

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Abstract

This novel study identifies the effective anti-inflammatory phenolic compounds in dandelion and provides mechanistic insights into their interactions with receptor proteins (toll-like receptor 4, TLR4; co-receptor myeloid differentiation protein-2, MD-2) using UHPLC-ESI-MS/MS, lipopolysaccharide (LPS)-stimulated THP-1 cell line, fluorescence quenching and anisotropy, molecular docking (single ligand and multi-ligand docking) and molecular dynamics simulation. A 50% aqueous methanol extract had a greater anti-inflammatory effect and higher chicoric acid content, compared with the 100% water and 100% methanol extracts. Chicoric acid, chlorogenic acid, methylophiopogonone A, caffeic acid, gallic acid monohydrate and 4'-O-demethylbroussonin A had relatively high binding energies and contents in all extracts. Chicoric acid competed with chlorogenic acid, 4'-O-demethylbroussonin A and quercetin for MD-2. Among dandelion’s phenolics, chicoric acid most effectively hindered TLR4-MD-2 complex formation, with a quenching constant of 0.62 × 106 L/mol for MD-2 or TLR4 at 320 K, and binding energies of -6.87 and -5.97 kcal/mol, respectively, for MD-2 and TLR4.

Keywords

Dandelion extractsPhenolic compounds binding affinityTLR4-MD-2 antagonistAnti-inflammatory agent

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Food Science and Human Wellness
Volume 12 Issue 6,
November 2023
Pages 2184-2194
DOI: 10.1016/j.fshw.2023.03.031
Cite this article:
Zou H, Ben T, Wu P, et al. Effective anti-inflammatory phenolic compounds from dandelion: identification and mechanistic insights using UHPLC-ESI-MS/MS, fluorescence quenching and anisotropy, molecular docking and dynamics simulation. Food Science and Human Wellness, 2023, 12(6): 2184-2194. https://doi.org/10.1016/j.fshw.2023.03.031

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Received: 30 March 2022
Revised: 24 April 2022
Accepted: 16 May 2022
Published: 04 April 2023
© 2023 Beijing Academy of Food Sciences.

This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
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