80% Aqueous MeOH extracts from the wood of Caesalpinia sappan, which showed
remarkable anticonvulsant activity, were fractionated using EtOAc, n-BuOH,
and H2O. Among them, the EtOAc fraction significantly inhibited the activi
ties of two GABA degradative enzymes, succinic semialdehyde dehydrogenase (
SSADH) and succinic semialdehyde reductase (SSAR). Repeated column chromato
graphies for the fraction guided by activity test led to the isolation of t
he two active principal components. Their chemical structures were determin
ed to be sappanchalcone and brazilin based on spectral data. The pure compo
unds, sappanchalcone (1) and brazilin (2), inactivated the SSAR activities
in a dose dependent manner, whereas SSADH was inhibited partially by sappan
chalcone and not by brazilin.