Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 May 22;10(6):620.
doi: 10.3390/antibiotics10060620.

Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor

Anne Ardaillou  1 , Jérôme Alsarraf  1 , Jean Legault  1 , François Simard  1 , André Pichette  1
Affiliations

Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor

Anne Ardaillou et al. Antibiotics (Basel). .

Abstract

Several families of naturally occurring C-alkylated dihydrochalcones display a broad range of biological activities, including antimicrobial and cytotoxic properties, depending on their alkylation sidechain. The catalytic Friedel-Crafts alkylation of the readily available aglycon moiety of neohesperidin dihydrochalcone was performed using cinnamyl, benzyl, and isoprenyl alcohols. This procedure provided a straightforward access to a series of derivatives that were structurally related to natural balsacones, uvaretin, and erioschalcones, respectively. The antibacterial and cytotoxic potential of these novel analogs was evaluated in vitro and highlighted some relations between the structure and the pharmacological properties of alkylated dihydrochalcones.

Keywords: Brønsted acid catalysis; Friedel–Crafts alkylation; Staphylococcus aureus; antibacterial; dihydrochalcone; hemisynthesis; natural products.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structure of various dihydrochalcones, including the aglycone moiety of neohesperidin dihydrochalcone (1).
Scheme 1
Scheme 1
Catalytic Geranylation of Dihydrochalcone 1.
See this image and copyright information in PMC

References

    1. Ibdah M., Martens S., Gang D.R. Biosynthetic pathway and metabolic engineering of plant dihydrochalcones. J. Agric. Food Chem. 2018;66:2273–2280. doi: 10.1021/acs.jafc.7b04445. - DOI - PubMed
    1. Stompor M., Broda D., Bajek-Bil A. Dihydrochalcones: Methods of acquisition and pharmacological properties—A first systematic review. Molecules. 2019;24:4468. doi: 10.3390/molecules24244468. - DOI - PMC - PubMed
    1. Veitch N.C., Grayer R.J. Flavonoids and their glycosides, including anthocyanins. Nat. Prod. Rep. 2011;28:1626–1695. doi: 10.1039/c1np00044f. - DOI - PubMed
    1. Snijman P.W., Joubert E., Ferreira D., Li X.-C., Ding Y., Green I.R., Gelderblom W.C.A. Antioxidant activity of the dihydrochalcones aspalathin and nothofagin and their corresponding flavones in relation to other rooibos (Aspalathus linearis) flavonoids, epigallocatechin gallate, and Trolox. J. Agric. Food Chem. 2009;57:6678–6684. doi: 10.1021/jf901417k. - DOI - PubMed
    1. Lavoie S., Legault J., Simard F., Chiasson É., Pichette A. New antibacterial dihydrochalcone derivatives from buds of Populus balsamifera. Tetrahedron Lett. 2013;54:1631–1633. doi: 10.1016/j.tetlet.2012.12.012. - DOI

LinkOut - more resources