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Chemical Constituents of Canarium subulatum and Their Anti-herpetic and DPPH Free Radical Scavenging Properties

Boonchoo Sritularak, Nopporn Boonplod, Vimolmas Lipipun and Kittisak Likhitwitayawuid

Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand

Faculty of Agricultural Production, Maejo University, Chiangmai 50290, Thailand

Department of Biochemistry and Microbiology, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand

Abstract: A methanol extract prepared from the bark of Canarium subulatum Guillaumin (Burseraceae) showed significant anti-herpetic activity. Chemical investigation of this plant extract resulted in the isolation of nine compounds which included β -amyrin (1), (-)-cubebin (2), scopoletin (3), 3,4-dihydroxybenzoic acid (4), 3,3 ¢ -di-O-methylellagic acid-4 ¢ -O-α-L-rhamnopyranoside (5), 3,3 ¢ -di-O-methylellagic acid-4 ¢ -O-β-D-gluco-pyranoside (6), 3-O-methylellagic acid-4 ¢ -O-α-L-arabinofuranoside (7), scopolin (8) and 3-O-methylellagic acid-4 ¢ -O-β-D-xylopyranoside (9) . The structures of these compounds were determined mainly through analysis of 1H and 13C NMR and MS data. All of the isolates were evaluated for anti-herpetic and DPPH free radical scavenging properties. β -Amyrin (1) and ( - )-cubebin (2) showed moderate anti-herpetic activity, whereas 3,4-dihydroxybenzoic acid (4), 3,3 ¢ -di-O-methylellagic acid-4 ¢ -O-α-L-rhamnopyranoside (5) exhibited recognizable DPPH free radical scavenging potential. This study is the first report on the chemical and biological properties of C. subulatum.

Keywords: Canarium subulatum ; Ellagic acid glycosides; Burseraceae; Anti-herpetic activity; Free radical scavenging activity.