Synthesis of Lipophilic Genistein Derivatives and Their Regulation of IL‐12 and TNF‐α in Activated J774A.1 Cells

Abstract

Genistein modulates inflammatory responses in part by reducing the production of the pro-inflammatory cytokines IL-12, TNF-a, and nitric oxide, by activated macrophages in response to lipopolysaccharide stimulus. Previous studies have shown that synthetic lipophilic genistein glycosides were significantly more active than hydrophilic glycosides. The aims of this study were to synthesize and to evaluate the effect of novel lipophilic genistein derivatives on IL-12, TNF-a, and nitric oxide production by J774A.1 cells. The results show that the modification of genistein enables the generation of non-cytotoxic compounds with increased IL-12 inhibition. However, these derivatives failed to inhibit TNF-a. The nitric oxide production was notably inhibited by the monoester (2, 3) and monoether (6, 7) compounds in a dose-dependent manner.

Dietary soy isoflavones during pregnancy suppressed the immune function in male offspring albino rats

“…This result was in agreement with Vasiadi et al [ 53 ]. In attempt to explain these phenomena, Castro et al [ 54 ] declared that there were no relation between increment of IL-12 and TNF-α when exposed to lipophilic genestein derivatives in vitro which enable to induce IL-12 inhibition but fail to inhibit TNF-α. A similar effect on IL-12 and TNF-α was reported in a study using lipopolysaccharides-stimulated dendritic cells (DCs) treated with aspirin as an anti-inflammatory drug [ 55 ].…”

Synthesis and biological evaluation of genistein‐O‐alkylamine derivatives as potential multifunctional anti‐Alzheimer agents

“…The 4′‐OH group in genistein molecule is more nucleophilic than 7‐OH and 5‐OH group, but less acidic than 7‐OH group, and thus, 4′‐OH or/and 7‐OH can be easily substituted by desired substituents . The intended compounds ( 3a–i , 5a–i ) were synthesized following the synthetic route as depicted in Scheme 1.…”

Ursolic Acid Derivatives Induced Apoptosis and Reduces the NF-<i>κ</i>B in Human Lung Adenocarcinoma Cells

“…The cellular viability was calculated using the formula (X1/X2)*100, considering X1 the OD of treated cells and X2 the mean OD of untreated cells. Compounds were considered cytotoxic when the viability was lower than 70% [12].…”