Aromatic compounds from an aqueous extract of "ban lan gen" and their antiviral activities

A pair of new diphenyl glycerol ether enantiomers (-)-1 and (+)-1 and two new methyl benzamidobenzoates 2 and 3, named (-)-(R)- and (+)-(S)-isatindigotrioic acid [(-)-1 and (+)-1] and isatindigoticamides A (2) and B (3), respectively, were isolated from an aqueous decoction of the roots of Isatis indigotica (ban lan gen). Their structures were elucidated by spectroscopic data analysis including 2D NMR experiments. The absolute configurations of (-)-1 and (+)-1 were assigned based on the CD exciton chirality method. Compounds 2 and 3 exhibited antiviral activities against HSV-1 with IC₅₀ values of 4.87 and 25.87 μmol/L, respectively. Compound 2 was also found active against Coxsackie virus B3 and LPS-induced NO production.