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Stereochemical Information of Neutraceticals

Stereochemistry of phytochemicals

Stereochemistry is important to drug activity because the form of a drug molecule influences how it interacts with the numerous biological molecules (enzymes, receptors, etc.). The stereochemistry of the most common phytochemicals is explained here.

Curcumin

Structure of Curcumin

  • Curcumin has three reactive functional groups: α, β-unsaturated diketo-linker, enol moiety two o-methoxy-phenolic groups. phenolic OH is essential for the overall antioxidant activity of curcumin.
  • Keto form of curcumin is non-planar while the enol isomer is planar. Enol form has antioxidative activity while keto doesn't.
  • Comparison of the energy values of keto and enol isomers of curcumin indicates higher stability of enol over keto form in gas phase as well as in solvent phase.
  • The phenolic OH groups are responsible for ROS scavenging activities while the α, β-unsaturated keto-enol structure is associated with the antitumor activity of curcumin.

Biological activity

  • Research shows antioxidative activity of curcumin (enol form) by the inhibition of autoxidation of styrene and methyl linoleate in chlorobenzene.
  • If the curcumin analogs (derivatives) don't have phenolic OH group then it cannot show antioxidant activity. Therefore, phenolic OH is essential for the overall antioxidant activity of curcumin.

Metabolism of curcumin

  • In vivo, curcumin is metabolized into various derivatives such as glucuronides and sulfates reduced curcumin derivatives like tetrahydro curcumin, hexahydro curcumin and octahydro curcumin.
  • All these metabolized compounds have the possible biological activity.
  • More Informaiton
    • Chemical and Structural Features Influencing the Biological Activity of Curcumin
    • Probing the Environmental Toxicity of Deep Eutectic Solvents and Their Components: An In Silico Modeling Approach
    • Chemical and Structural Features Influencing the Biological Activity of Curcumin

    Derivatives of Curcumin

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    Derivatives of Curcumin
    • Curcumin has various biological properties such as anti-inflammatory, anti-diabetic, anti-mutagenicity-proliferative, anti-oxidant, anti-angiogenic and can also use in the treatment of various cancer and Alzheimer's disease.
    • TNF-induced NF-B activation can be suppressed by demethoxycurcumin and bisdemethoxycurcumin, resulting in an anti-inflammatory action.

Resveratrol

The stilbene-based structure of resveratrol includes two phenolic rings connected by a styrene double bond, allowing it to create 3,4',5-trihydroxystiblene in both cis and trans orientations. Resveratrol exists in both cis and trans forms and trans is the more stable form. Cis trans has antiplatelet and trans has anti-inflammatory and immunomodulatory activity.

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cis and trans resveratrol

More Information :

  • A Comparative Study of the Anti-Platelet Effects of cis- and trans-Resveratrol
  • Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism
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