Recent Advances in the Synthetic Chemistry and Application of Molecular Modeling for Different Aspects of The Golden Spice - Curcumin
Posted: 7 Feb 2020 Last revised: 16 Feb 2020
Date Written: January 21, 2020
Curcumin is a hydrophobic polyphenolic compound, isolated from the rhizomes of Curcuma longa, family Zingiberaceae. Turmeric has found mention in traditional systems of medicine including Ayurveda and is reckoned as the golden spice due to its wide range of therapeutic and medicinal uses. Natural curcumin is biosynthesized from two molecules of feruloyl-CoA and one molecule of malonyl-CoA in presence of curcuminoid synthase and type III polyketide synthases. Curcumin and other curcuminoids like desmethoxycurcumin and bisdesmethoxycurcumin are extracted from turmeric using Soxhlet extraction or slurry extraction. Curcumin however suffers from drawback of low oral bioavailability as it undergoes extensive first pass metabolism in liver, which limits its usage as a drug. Hence, many approaches have been utilized to overcome the problems of bioavailability, the most important from chemistry perspective being structural modification. Thus, different analogs and derivatives of curcumin based on its basic scaffold have been synthesized. Curcumin has been structurally modified to monocarbonyl analogs and its derivatives, enone derivatives, diacetyl derivatives, di-oxime derivatives, ether derivatives, phosphorylated derivatives, ester derivatives, metal complexes and symmetrical and asymmetrical derivatives using different synthetic methods of preparations. Curcumin was first synthesized using Pabon’s method but now there many novel methods of preparation which involve microwave-assisted, ultrasound irradiation-assisted using solid catalysts like activated chicken eggshell (ACE), microwave-assisted one-pot synthetic method. Curcumin exhibits different medicinal properties and pharmacological actions like anti-tumor, anti-diarrhea, carminative, anti-inflammatory, anti-oxidant, anti-fungal, nephroprotective activity, anti-rheumatic, anti-mutagenic, anti-carcinogenic, neuroprotective, anti-retroviral and hepatoprotective activities thus rightly referred to as the golden spice. Some experiments using medicinal chemistry softwares have also been pursued for curcumin. For example in a study, molecular dynamics simulation was used to predict the possible mechanism of pharmacological action, its binding to a specific protein, conditions for inhibitory or stimulatory action of curcumin on this protein, and its analogs and derivatives.
In this poster, we will deal with the chemistry and synthesis of curcumin, its chemical modifications as well as provide an overview of the recent applications of molecular modeling with respect to various medicinal chemistry aspects of curcumin.
Keywords: Alzheimer's disease, curcumin, curcuminoids, curcumin derivatives, curcumin analogs, Pabon's method, molecular modeling, docking, molecular dynamic simulations
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