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
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 (LP...
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| Format: | Article |
| Language: | English |
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Tsinghua University Press
2023-11-01
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| Series: | Food Science and Human Wellness |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2213453023000836 |
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| author | Hui Zou Tingting Ben Ping Wu Geoffrey I.N. Waterhouse Yilun Chen |
| author_facet | Hui Zou Tingting Ben Ping Wu Geoffrey I.N. Waterhouse Yilun Chen |
| author_sort | Hui Zou |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-411ec884e04b4be68539ac60403798b4 |
| institution | Kabale University |
| issn | 2213-4530 |
| language | English |
| publishDate | 2023-11-01 |
| publisher | Tsinghua University Press |
| record_format | Article |
| series | Food Science and Human Wellness |
| spelling | doaj-art-411ec884e04b4be68539ac60403798b42025-02-03T02:42:15ZengTsinghua University PressFood Science and Human Wellness2213-45302023-11-0112621842194Effective anti-inflammatory phenolic compounds from dandelion: identification and mechanistic insights using UHPLC-ESI-MS/MS, fluorescence quenching and anisotropy, molecular docking and dynamics simulationHui Zou0Tingting Ben1Ping Wu2Geoffrey I.N. Waterhouse3Yilun Chen4College of Food Science and Engineering, Shandong Agricultural University, Key Laboratory of Food Processing Technology and Quality Control in Shandong Province, Tai’an 271018, ChinaCollege of Food Science and Engineering, Shandong Agricultural University, Key Laboratory of Food Processing Technology and Quality Control in Shandong Province, Tai’an 271018, ChinaCollege of Food Science and Engineering, Shandong Agricultural University, Key Laboratory of Food Processing Technology and Quality Control in Shandong Province, Tai’an 271018, ChinaSchool of Chemical Sciences, University of Auckland, Auckland 1142, New Zealand; Corresponding authors.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; Corresponding authors.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.http://www.sciencedirect.com/science/article/pii/S2213453023000836Dandelion extractsPhenolic compounds binding affinityTLR4-MD-2 antagonistAnti-inflammatory agent |
| spellingShingle | Hui Zou Tingting Ben Ping Wu Geoffrey I.N. Waterhouse Yilun Chen 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 Dandelion extracts Phenolic compounds binding affinity TLR4-MD-2 antagonist Anti-inflammatory agent |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | Dandelion extracts Phenolic compounds binding affinity TLR4-MD-2 antagonist Anti-inflammatory agent |
| url | http://www.sciencedirect.com/science/article/pii/S2213453023000836 |
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