Synthesis and antimicrobial activity of geranyloxy- and farnesyloxy-
acetophenone derivatives against {*filter*}pathogens.
Bonifait L, Marquis A, Genovese S, Epifano F, Grenier D.
Fitoterapia. 2012 Jun 11.
Groupe de Recherche en cologie Buccale, Facult de Mdecine Dentaire,
Universit Laval, 2420 Rue de la Terrasse, Qubec City, QC, Canada,
G1V 0A6.

Abstract
The compounds 2',6'-dihydroxy-4'-geranyloxyacetophenone (1) and 2',6'-
dihydroxy-4'-farnesyloxyacetophenone (2) are oxyprenylated secondary
metabolites extracted from plants belonging to the Rutaceae family.
In this study, 1 and 2 were synthesized and tested for their
antimicrobial activity towards major {*filter*}pathogens.
Compounds 1 and 2 were synthesized by selective prenylation of 2,4,6-
trihydroxyacetophenone at the 4' position with geranyl and farnesyl
bromide, respectively.
Compound 1 showed stronger antimicrobial activity than 2 against major
{*filter*}pathogens, including Gram positive bacteria (Streptococcus
mutans, Streptococcus sobrinus), Gram negative bacteria (Prevotella
intermedia, Porphyromonas gingivalis) and Candida albicans.
Evidences were obtained that the mode of action of 1 and 2 may be
related to their iron-chelating property.
This study suggests that 1 and 2 may represent potential natural
molecules for the prevention/treatment of common {*filter*}infections,
including dental caries, periodontal disease, and candidiasis.

Copyright ? 2012. Published by Elsevier B.V.

PMID:22698715

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