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. 2021 Mar 14;26(6):1608.
doi: 10.3390/molecules26061608.

Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5- O-Acyl Derivatives of Quercetin

Stephen Lo  1 , Euphemia Leung  2 , Bruno Fedrizzi  1 , David Barker  1   3
Affiliations

Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5- O-Acyl Derivatives of Quercetin

Stephen Lo et al. Molecules. .

Abstract

Quercetin is a flavonoid that is found in many plant materials, including commonly eaten fruits and vegetables. The compound is well known for its wide range of biological activities. In this study, 5-O-acyl derivatives of quercetin were synthesised and assessed for their antiproliferative activity against the HCT116 colon cancer and MDA-MB-231 breast cancer cell lines; and their radical scavenging activity against the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical species. Four derivatives were found to have improved the antiproliferative activity compared to quercetin whilst retaining radical scavenging activity.

Keywords: antiproliferative; breast cancer; colon cancer; quercetin; radical scavenging.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structure of quercetin, a pentahydroxy flavonol.
Scheme 1
Scheme 1
Syntheses of 5-O-acyl quercetin compounds: (i) Ph2CCl2, PhOPh, 175 °C, 24 h, 68%, (ii) BnBr, K2CO3, dimethylformamide (DMF), 100 °C, 24 h, 54%; (iii) Et3N, acyl chlorides, 4a 75%, 4b 94%, 4e 88%, 4f 88%; (iv) Pd(OH)2/C or Pd/C, H2, tetrahydrofuran (THF), r.t., 4 d, 5a 46%, 5b 73%, 5c 56% over 2 steps, 5d 60% over 2 steps, 5e 70%, 5f 55%, 5g 88% over two steps.
Figure 2
Figure 2
Mean cell proliferation rates (±standard error(SE) of quercetin and 5-O-quercetin derivatives against HCT116 and MDA-MB-231 cancer cell lines (cell proliferation in presence of control = 100%).
Figure 3
Figure 3
Mean Trolox equivalence (TE) concentration (±SE) of quercetin at various concentrations against (a) ABTS radical cation; and (b) against DPPH radical.
See this image and copyright information in PMC

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