A system and method for transcoding digital content (e.g. web content) by correctly employing one annotation for multiple digital contents. This can efficiently reduce the workloads required for the addition of annotation data during the transcoding process. A transcoding system comprises an annotation database system for storing annotation data to be used for the transcoding of contents, and a transcoder for transcoding the contents based on annotation data stored in the annotation database system. Upon receiving an inquiry from the transcoder, a correlation between elements in the contents and descriptions of the annotation data is checked to select one annotation that can be employed for transcoding the content. The correlation is specifically determined based on XPath information.