Synthesis and biological evaluation of novel curcuminoid derivatives - PubMed (original) (raw)

Synthesis and biological evaluation of novel curcuminoid derivatives

Ya-Kun Cao et al. Molecules. 2014.

Abstract

Curcuminoids have been reported to possess multiple bioactivities, such as antioxidant, anticancer and anti-inflammatory properties. Three novel series of curcuminoid derivatives (11a-h, 15a-h and 19a-d) with enhanced bioactivity have been synthesized. Among the synthesized compounds, 11b exhibited the most significant activity with an MIC of 0.5 µM /mL against selected medically important Gram-positive cocci (S. aureus and S. viridans) and Gram-negative bacilli (E. coli and E. cloacae). The derivatives exhibited remarkable results in an antioxidant test with an IC50 2.4- to 9.3-folder smaller than curcuminoids. With respect to antiproliferative activity against Hep-G2, LX-2, SMMC7221 and MDA-MB-231, the derivatives exhibited an effect stronger than curcuminoids with an IC50 ranging from 0.18 to 4.25 µM.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1

Figure 1

Curcumin, demethoxycurcumin and bisdemethoxycurcumin.

Scheme 1

Scheme 1

Syntheses of curcumin (1a) and bisdemethoxycurcumin (1b).

Scheme 2

Scheme 2

Synthesis of selenomethionine-substituted curcuminoids and methionine-substituted curcuminoids.

Scheme 3

Scheme 3

Synthesis of curcuminoid-caffeic acid and curcuminoid-ferulic acid conjugates.

Scheme 4

Scheme 4

Synthesis of curcuminoid-glycyrrhetinic acid conjugates.

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References

    1. Civjan N. Chemical Biology: Approaches to Drug Discovery and Development to Targeting Disease. John Wiley & Sons; Hoboken, NJ, USA: 2012.
    1. Dias D.A., Urban S., Roessner U. A historical overview of natural products in drug discovery. Metabolites. 2012;2:303–336. - PMC - PubMed
    1. Butler M.S. Natural products to drugs: Natural product derived compounds in clinical trials. Nat. Prod. Rep. 2005;22:162–195. - PubMed
    1. Chattopadhyay I., Biswas K., Bandyopadhyay U., Banerjee R.K. Turmeric and curcumin: Biological actions and medicinal applications. Curr. Sci. 2004;87:44–53.
    1. Motterlini R., Foresti R., Bassi R., Green C.J. Curcumin, an antioxidant and anti-inflammatory agent, induces heine oxygenase-1 and protects endothelial cells against oxidative stress. Free Radic. Biol. Med. 2000;28:1303–1312. - PubMed

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