Groupe de Recherche en Écologie Buccale, Faculté de Médecine Dentaire, Université Laval, Québec City, QC, Canada.
Fitoterapia. 2012 Sep;83(6):996-9. doi: 10.1016/j.fitote.2012.06.003. Epub 2012 Jun 11.
The compounds 2',6'-dihydroxy-4'-geranyloxyacetophenone (1) and 2',6'-dihydroxy-4'-farnesyloxy-acetophenone (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 toward major oral 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 oral 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 oral infections, including dental caries, periodontal disease, and candidiasis.
2',6'-二羟基-4'-香叶基乙氧基苯乙酮（1）和 2',6'-二羟基-4'-法呢基乙氧基苯乙酮（2）是从芸香科植物中提取的氧代异戊烯基次生代谢产物。在这项研究中，1 和 2 被合成并测试了它们对主要口腔病原体的抗菌活性。化合物 1 和 2 通过 4' 位的香叶基和法尼基溴选择性异戊烯化 2,4,6-三羟基苯乙酮合成。化合物 1 对主要口腔病原体（包括革兰氏阳性菌（变形链球菌、唾液链球菌）、革兰氏阴性菌（中间普氏菌、牙龈卟啉单胞菌）和白色念珠菌）的抗菌活性强于 2。有证据表明，1 和 2 的作用模式可能与其铁螯合特性有关。这项研究表明，1 和 2 可能代表预防/治疗常见口腔感染（包括龋齿、牙周病和念珠菌病）的潜在天然分子。
