The Machilus genus (Lauraceae) had been extensively utilized in folk medicine due to its broad range of bioactivities. In the present study, a series of chromatographic separations of the methanol extract of stems of M. philippinensis led to the identification of thirty eight compounds totally. Among these, biscinnamophilin ( 1 ), machilupins A–C ( 2–4 ), machilutone A ( 5 ), and machilusoxide A ( 6 ) were new compounds reported for the first time. In addition, 5 was characterized with a unprecedented carbon skeleton. Other known compounds, including the major compounds cinnamophilin ( 7 ) and meso -dihydroguaiaretic acid ( 8 ), are identified by comparison of their physical and spectroscopic data with reported values. One of the reported compounds, cinnamophilin A ( 10 ), should be revised as dehydroguaiaretic acid ( 9 ) after careful comparison of all the ~(1) H and ~(13) C NMR data. Moreover, the neuroprotective activity of cinnamophilin ( 7 ) was examined in a primary cortical neuron culture and the results indicated that 7 was effective against glutamate induced excitotoxicity.
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