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Review
. 2019 Oct 30:7:697.
doi: 10.3389/fchem.2019.00697. eCollection 2019.

New Perspectives for Fisetin

Grzegorz Grynkiewicz  1 , Oleg M Demchuk  1
Affiliations
Review

New Perspectives for Fisetin

Grzegorz Grynkiewicz et al. Front Chem. .

Abstract

Fisetin is a flavonol that shares distinct antioxidant properties with a plethora of other plant polyphenols. Additionally, it exhibits a specific biological activity of considerable interest as regards the protection of functional macromolecules against stress which results in the sustenance of normal cells cytoprotection. Moreover, it shows potential as an anti-inflammatory, chemopreventive, chemotherapeutic and recently also senotherapeutic agent. In view of its prospective applications in healthcare and likely demand for fisetin, methods for its preparation and their suitability for pharmaceutical use are discussed herein.

Keywords: anti-aging; anti-cancer; biological activity of flavonols; fisetin; flavon-3-ols; synthesis of flavonols.

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Figures

Figure 1
Figure 1
Fisetin (1) and biogenetic precursors of the 5-deoxy flavonoid series: chalcones (3 and 5), flavanones (4 and 6), and dihydroflavonols (7 and 8).
Figure 2
Figure 2
Equilibrium between the chalcone and flavanone counterparts.
Figure 3
Figure 3
Isomerism of fisetin involving quinone/quinone methide structures; justification of a strongly electrophilic character of the catecholic ring (Awad et al., 2001).
Figure 4
Figure 4
Kostanecki's synthesis of fisetin.
Figure 5
Figure 5
Robinson's synthesis of fisetin.
Figure 6
Figure 6
General methods for the chalcone preparation: (A) Claisen-Schmidt condensation (base catalyzed); (B) Suzuki cross-coupling (Pd catalyzed); (C) carbonylative Heck olefin arylation (catalyzed by Pd complexes).
Figure 7
Figure 7
General approaches to flavone syntheses: (A) from chalcones (following Kostanecki's synthesis); (B) from 1,3-diaryl propandiones (following Kostanecki—Robinson—Venkataraman ideas); (C) from phenylalkenyl ketones, according to Lee (2017).
Figure 8
Figure 8
General scheme for the AFO synthesis of flavonols upon chalcone epoxidation with H2O2.
Figure 9
Figure 9
Synthesis of fisetin by arylation of the 2-bromochromone derivative.
See this image and copyright information in PMC

References

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