Antiemetic Principles of Alpinia officinarum

Bioasay-guided fractionation of the antiemetic constituents of Alpinia officinarum was performed, and eight compounds (18) including a new compound were isolated. Among the seven known compounds, two flavonoids (1, 2), four diarylheptanoids (3, 5, 6, 8), and one sterol (4) were obtained, with five (26) of those compounds showing antiemetic activity in a copper sulfate induced emesis assay in young chicks. The structure of the new compound 7, which also showed antiemetic activity, was determined as 5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-3-heptanone. The structure of 7 was established on the basis of spectroscopic data interpretation.