Isolation and structure of woodorien, a new glucoside having antiviral activity, from Woodwardia orientalis.
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Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1, and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ability of HSV-1 and poliovirus more strongly than did the methanol extract. By bioassay-directed fractionation of the aqueous extract, a new glucoside, woodorien (1), along with five known compounds were isolated from an EtOAc-soluble fraction that had antiviral activity. The structures of these compounds were determined by the use of two dimensional (2D) NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY and heteronuclear multiple-bond multiple-quantum coherence (HMBC)). Woodorien (1) was the most potent inhibitor against HSV-1 among the isolated compounds.