85801-92-9

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 123-54-6 acetylacetone 

Relevant academic research and scientific papers

Method for artificially synthesizing curcumin and derivatives thereof

The invention provides a method for artificially synthesizing curcumin and derivatives thereof. The method comprises the following steps: reacting acetylacetone with boron oxide under a weakly acidiccondition to generate a complex, protecting methylene groups between two ketocarbonyl groups, adding a catalyst, reacting the complex with vanillin (benzaldehyde derivative) to obtain a curcumin derivative intermediate (I), and hydrolyzing the intermediate to obtain the curcumin derivative. The selectivity of the reaction is far higher than that of a preparation reaction in an alkaline system, andis macroscopically and specifically embodied in the yield of curcumin and derivatives thereof: in the existing two-pot reaction, the yield of curcumin in the whole process is about 60%; the yield ofthe preparation method can reach 80-90%. Therefore, the method provided by the invention reduces the waste of raw materials and the generation of byproducts; and complete hydrolysis can be realized only at normal temperature, insoluble substances included in the product are almost zero, and the obtained product is pure.

Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin

Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose-response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues.

3,3′-OH curcumin causes apoptosis in HepG2 cells through ROS-mediated pathway

In this paper, we synthesized a series of curcumin analogs and evaluated their cytotoxicity against HepG2 cells. The results exhibited that the hydroxyl group at 3,3′-position play an essential role in enhancing their anti-proliferation activity. More importantly, 3,3′-hydroxy curcumin (1b) caused apoptosis in HepG2 cells with the ROS generation, which may be mainly composed of hydroxyl radicals (HO[rad]) and H2O2. The more cytotoxic activity and ROS-generating ability of 1b may be due to the more stable in (RPMI)-1640 medium and more massive uptake than curcumin. Then the generation of ROS can disrupt the intracellular redox balance, induce lipid peroxidation, cause the collapse of the mitochondrial membrane potential and ultimately lead to apoptosis. The results not only suggest that 3,3′-hydroxy curcumin (1b) may cause HepG2 cells apoptosis through ROS-mediated pathway, but also offer an important information for design of curcumin analog.

Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor

Inhibition of the amyloid β aggregation process could possibly prevent the onset of Alzheimer's disease. In this article, we report a structure-activity relationship study of curcumin analogues for anti amyloid β aggregation activity. Compound 7, the ideal amyloid β aggregation inhibitor in vitro among synthesized curcumin analogues, has not only potent anti amyloid β aggregation effects, but also water solubility more than 160 times that of curcumin. In addition, new approaches to improve water solubility of curcumin-type compounds are proposed.

Synthesis and evaluation of curcumin derivatives toward an inhibitor of beta-site amyloid precursor protein cleaving enzyme 1

To research a new non-peptidyl inhibitor of beta-site amyloid precursor protein cleaving enzyme 1, we focused on the curcumin framework, two phenolic groups combined with an sp2 carbon spacer for low-molecular and high lipophilicity. The structure-activity relationship study of curcumin derivatives is described. Our results indicate that phenolic hydroxy groups and an alkenyl spacer are important structural factors for the inhibition of beta-site amyloid precursor protein cleaving enzyme 1 and, furthermore, non-competitive inhibition of enzyme activity is anticipated from an inhibitory kinetics experiment and docking simulation.