Toll-like receptors as a target of food-derived anti-inflammatory compounds.

Toll-like receptors (TLRs) play a key role in linking pathogen recognition with the induction of innate immunity. They have been implicated in the pathogenesis of chronic inflammatory diseases, representing potential targets for prevention/treatment. Vegetable-rich diets are associated with the reduced risk of several inflammatory disorders.

Transthiocarbamoylation of proteins by thiolated isothiocyanates.

Isothiocyanates, membrane-permeable electrophiles that form adducts with thiols, have been suggested to have important medical benefits. Here we shed light on isothiocyanate-thiol conjugates and studied their electrophilic potential transferring an isothiocyanate moiety to cellular proteins. When we examined the effect of sulfhydryl molecules on cellular response induced by 6-methylsulfinylhexyl isothiocyanate (6-HITC), an analog of sulforaphane isolated from broccoli, we observed significant induction of heme oxygenase-1 by 6-HITC even in the presence of N-acetyl-L-cysteine or glutathione (GSH).

Polymer-assisted solution-phase synthesis and neurite-outgrowth-promoting activity of 15-deoxy-delta(12,14)-PGJ2 derivatives.

An efficient solution-phase synthesis of rac-15-deoxy-delta(12,14)-PGJ2 (15dPGJ2) derivatives that contain variable alpha and omega chains based on a polymer-assisted strategy and their neurite-outgrowth-promoting activity are described. The strategy for the synthesis of PGJ2 derivatives involves the use of a vinyl iodide bearing cyclopentenone as a key intermediate, which undergoes Suzuki-Miyaura coupling and subsequent Lewis acid catalyzed aldol condensation for incorporation of the omega and alpha chains, respectively. For easy access to the PGJ2 derivatives, a polymer-supported catalyst and scavengers were adapted for use in these four diverse steps, in which workup and purification can be performed by simple filtration of the solid-supported reagents.

Solid-phase synthesis and biological activity of a combinatorial cross-conjugated dienone library.

The solid-phase synthesis of a combinatorial cross-conjugated dienone library based on the structure of clavulones and their biological activity are reported. Clavulones are a family of marine prostanoids, and are composed of a cross-conjugated dienone system bearing two alkyl side-chains. The cross-conjugated dienone system irreversibly reacted with two nucleophiles.