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Figure legend: Mechanistic study of two flavonoid isomers Acacetin (ACA) and Biochanin A (BCA) with anti-inflammation activities. (A, B) The binding of ACA and BCA to the c-Src protein was determined by drug affinity responsive target stability (DARTS) and western blotting, followed by quantification by densitometry. Data points and bar represent arithmetic means ± SD, *P < 0.05, **P < 0.01, ***P < 0.001, and ****P < 0.0001 as compared to the undigested DMSO group. (C). Computational modeling of ACA and BCA in the ATP-binding pocket of the c-Src kinase (PDB entry: 7NG7). Magnified representation for (D) ACA and (E) BCA showing different residues of the c-Src protein are in contact with each of the flavonoids.
Anti-inflammation Mechanisms of Flavones Are Highly Sensitive to the Position Isomers of Flavonoids: Acacetin vs Biochanin A
Acacetin (ACA) and biochanin A (BCA) are isomeric monomethoxyflavones with different structural positions of the 4'-methoxy-phenyl group. Both of them are present in many commonly consumed foods, such as citrus fruits and vegetables, and have been discovered with anti-inflammatory activities, but their mechanisms of action are not clearly elucidated at the molecular level. Herein, we reported the structure-activity relationship of ACA and BCA regarding their potency in inhibiting nitric oxide (NO) production, proinflammatory enzyme expression, and mRNA expression of proinflammatory cytokines in the lipopolysaccharide (LPS)-induced RAW 264.7 cells. Furthermore, transcriptome analysis was conducted to map out the overall pathways impacted by these two isomers.
Cao Y, Tan YJ, Huang D. Anti-inflammation Mechanisms of Flavones Are Highly Sensitive to the Position Isomers of Flavonoids: Acacetin vs Biochanin A. J Agric Food Chem. 2024 Sep 17. doi: 10.1021/acs.jafc.4c05060. Epub ahead of print. PMID: 39287184.