Thesis (M.Sc.In Pharm)--Chulalongkorn University, 2010

Phytochemical study of the root bark of Artocarpus lakoocha Roxb. led to the isolation of five pure compounds, including three new 2-arylbenzofurans, namely artolakoochol, cycloartolakoochol and 4-hydroxyartolakoochol and a new prenylated flavone named 5,7,2′,4′,-tetrahydroxy-3-prenyl-6-geranylflavone, together with the known compound cudraflavone C. Their structures were elucidated through analysis of their spectroscopic data (UV, IR, MS, NMR) and by comparison with previously reported data. The isolated compounds were evaluated for free radical scavenging, antityrosinase and antiherpetic activities. Artolakoochol, cycloartolakoochol and 4-hydroxy artolakoochol showed potent free radical scavenging activity, where as 5,7,2′,4′,-tetrahydroxy-3-prenyl-6-geranylflavone and cudraflavone C showed moderate activity. Furthermore, 4-hydroxyartolakoochol exhibited weak tyrosinase inhibitory activity. The prenylated flavones, 5,7,2′,4′,-tetrahydroxy-3-prenyl-6-geranylflavone and cudraflavone C, showed activity against herpes simplex virus (HSV-1 and HSV-2). The compound 5,7,2′,4′,-tetrahydroxy-3-prenyl-6-geranylflavone exhibited moderate activity against both types of herpes simplex virus in the Inactivation and Post-treatment assay, while cudraflavone C showed weak activity against both types of herpes simplex virus in the Inactivation assay.