52328-96-8

Usage

Uses

Used in Pharmaceutical Industry:
BisdeMethoxycurcuMin is used as an anti-inflammatory and antioxidant agent for its potential to reduce inflammation and combat oxidative stress. It is being studied for its potential to help with conditions such as arthritis, diabetes, and certain types of cancer.
Used in Healthcare Industry:
BisdeMethoxycurcuMin is used as a potential therapeutic agent for its potential health benefits in managing inflammation and oxidative stress-related conditions. Ongoing research is exploring its applications in medicine and healthcare for the treatment and prevention of various diseases.

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 123-54-6 acetylacetone 
• 100-52-7 benzaldehyde 
• 30802-00-7 p-coumaroyl-coenzyme A 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 2887-07-2 4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 98886-08-9 Acetic acid 4-[(1E,3Z,6E)-7-(4-acetoxy-phenyl)-3-hydroxy-5-oxo-hepta-1,3,6-trienyl]-phenyl ester 
• 113482-94-3 1,7-bis(4-hydroxyphenyl)heptane-3,5-dione 
• 160096-61-7 1E,6E-1,7-bis(4-methoxyphenyl)hepta-1,6-diene-3,5-dione 
• 41137-85-3 (+/-)-5-hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone 

Relevant academic research and scientific papers

Phenolic 1,3-diketones attenuate lipopolysaccharide-induced inflammatory response by an alternative magnesium-mediated mechanism

Background and Purpose: Toll-like receptor 4 (TLR4) plays a key role in the induction of inflammatory responses both in peripheral organs and the CNS. Curcumin exerts anti-inflammatory functions by interfering with LPS-induced dimerization of TLR4–myeloid

Method for artificially synthesizing curcumin and derivative thereof

The invention discloses a method for artificially synthesizing curcumin and a derivative thereof. The method comprises the steps of adopting calcium acetylacetonate as a acetylacetone supply source, carrying out claisen-schmidt ester condensation reaction on the calcium acetylacetonate and a corresponding benzaldehyde derivative, and dehydrating under the catalysis of a dehydrating agent which is tributyl borate to obtain a product intermediate (I) which is curcumin calcium salt; then hydrolyzing the intermediate (I) through a one-pot method to obtain a crude product, and purifying the crude product so as to obtain the final product curcumin and the derivative thereof. Compared with a acetylacetone boric acid complex method, according to the method provided by the invention, the calcium acetylacetonate is used, so that active sites of acetylacetonate during a reaction process are more accurate and activated, the generation of by-products is reduced, and the yield of the curcumin and the derivative thereof is improved.

Versatility of the Curcumin Scaffold: Discovery of Potent and Balanced Dual BACE-1 and GSK-3β Inhibitors

The multitarget approach has gained increasing acceptance as a useful tool to address complex and multifactorial maladies such as Alzheime?s disease (AD). The concurrent inhibition of the validated AD targets β-secretase (BACE-1) and glycogen synthase kin

Mechanochemical synthesis of 2,2-difluoro-4, 6-bis(β-styryl)-1,3,2-dioxaborines and their use in cyanide ion sensing

The conversion of arylaldehydes to 1,7-diaryl-5-hydroxyhepta-1,4,6-trien-3-ones (curcuminoids) and the mechanochemical cyclization of these products to 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines using BF3-Et2O are described. Investigation of the cyanide ion sensing ability of the 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines, in relation to the substituent groups on the aryl ring, showed that a hydroxy susbstituent is required, preferably para to the intervening carbon bridge.

Structural basis for the one-pot formation of the diarylheptanoid scaffold by curcuminoid synthase from Oryza sativa

Curcuminoid synthase (CUS) from Oryza sativa is a plant-specific type III polyketide synthase (PKS) that catalyzes the remarkable one-pot formation of the C6-C7-C6 diarylheptanoid scaffold of bis-demethoxycurcumin, by the condensation of two molecules of 4-coumaroyl-CoA and one molecule of malonyl-CoA. The crystal structure of O. sativa CUS was solved at 2.5-? resolution, which revealed a unique, downward expanding active-site architecture, previously unidentified in the known type III PKSs. The large active-site cavity is long enough to accommodate the two C 6-C3 coumaroyl units and one malonyl unit. Furthermore, the crystal structure indicated the presence of a putative nucleophilic water molecule, which forms hydrogen bond networks with Ser351-Asn142-H 2O-Tyr207- Glu202, neighboring the catalytic Cys174 at the active-site center. These observations suggest that CUS employs unique catalytic machinery for the one-pot formation of the C6-C7-C 6 scaffold. Thus, CUS utilizes the nucleophilic water to terminate the initial polyketide chain elongation at the diketide stage. Thioester bond cleavage of the enzyme-bound intermediate generates 4-coumaroyldiketide acid, which is then kept within the downward expanding pocket for subsequent decarboxylative condensation with the second 4-coumaroyl-CoA starter, to produce bisdemethoxycurcumin. The structure-based site-directed mutants, M265L and G274F, altered the substrate and product specificities to accept 4-hydroxyphenyl- propionyl-CoA as the starter to produce tetrahydrobisdemethoxy- curcumin. These findings not only provide a structural basis for the catalytic machinery of CUS but also suggest further strategies toward expanding the biosynthetic repertoire of the type III PKS enzymes.

Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors

Series of curcumin derivatives were synthesized; the inhibitory activities on thioredoxin reductase (TrxR) of all analogues were evaluated by DTNB assay in vitro. It is found that most of the analogues can inhibit TrxR in the low micromolar range; Structure-activity relationship analysis reveals that analogues with furan moiety have excellent inhibitory effect on TrxR in an irreversible manner, indicating that the furan moiety may serve as a possible pharmacophore during the interaction of curcumin analogues with TrxR. The effect of selected curcuminoids on growth of different TrxR overexpressed cancer cell lines was also investigated and discussed.

Curcuminoids form reactive glucuronides in vitro

Curcumin is of current interest because of its putative anti-inflammatory, anticarcinogenic, and anti-Alzheimer's activity, but its pharmacokinetic and metabolic fate is poorly understood. The present in vitro study has therefore been conducted on the glucuronidation of curcumin and its major phase I metabolite, hexahydro-curcumin, as well as of various natural and artificial analogs. The predominant glucuronide generated by rat and human liver microsomes from curcumin, hexahydro-curcumin, and other analogs with a phenolic hydroxyl group was a phenolic glucuronide according to LC-MS/MS analysis. However, a second glucuronide carrying the glucuronic acid moiety at the alcoholic hydroxyl group was formed from the same curcuminoids, but not hexahydro-curcuminoids, by human microsomes. Curcuminoids without a phenolic hydroxyl group gave rise to the aliphatic glucuronide only. The phenolic glucuronides of curcuminoids, but not of hexahydro-curcuminoids, were rather lipophilic and, in part, unstable in aqueous solution, their stability depending strongly on the type of aromatic substitution. The phenolic glucuronide of curcumin and of its natural congeners, but not the parent compounds, clearly inhibited the assembly of microtubule proteins under cell-free conditions, implying chemical reactivity of the glucuronides. These novel properties of the major phase II metabolites of curcuminoids deserve further investigation.

A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 °C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain.

Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver

Curcumin and its natural congeners are of current interest because of their putative anti-inflammatory and anticarcinogenic activities, but knowledge about their metabolic fate is scant. In the present study conducted with precision-cut liver slices from

TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin

The activator protein-1 (AP-1) family of transcription factors, including the most common member c-Jun-c-Fos, participates in regulation of expression of numerous genes involved in proliferation, apoptosis, and tumorigenesis in response to a wide array of stimuli including pro-inflammatory cytokines, growth factors, stress, and tumor promoters. A number of plant polyphenols including curcumin, a yellow compound in the spice turmeric, have been shown to inhibit the activation of AP-1. Curcumin is a polyphenolic dienone that is potentially reactive as a Michael acceptor and also is a strong anti-oxidant. Multiple activities reported for curcumin, including inhibition of the stress-induced activation of AP-1, have been suggested to involve the anti-oxidant properties of curcumin. In the present study, a library of analogs of curcumin was screened for activity against the TPA-induced activation of AP-1 using the Panomics AP-1 Reporter 293 stable cell line which is designed for screening potential inhibitors. Numerous analogs were identified that were more active than curcumin, including analogs that were not anti-oxidants and analogs that were not Michael acceptors. Clearly, anti-oxidant activity or reactivity as a Michael acceptor is not an essential feature of active compounds. In addition, a number of analogs were identified that enhanced the TPA-induced activation of AP-1. The results from screening were confirmed using BV-2 microglial cells where curcumin and analogs were shown to inhibit LPS-induced COX-2 expression; analogs identified as more potent than curcumin in the screening assay were also more potent than curcumin in preventing COX-2 expression.