The Syntheses of 14C-labelled Ferulic Acid (FA-2-14C) and Its Triterpene Esters (14C-FAE)

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In order to study the biological fates of ferulic acid (FA) or its triterpene esters (FAE) the 14C-labelling of these compounds has been investigated. These 14C-labelled compounds are generally synthesized from malonic acid-2-14C or 14CO2, as a starting radioactive material. But relatively low yields, about 30%, are obtained in the synthesis of ferulic acid esters from malonic acid -2-14C, and in the synthesis of the compounds from 14CO2, on the other hand, the process is rather complex. In a preliminary experiment, we obtained a higher yield of ferulic acid ester, about 40%, by the method starting from diethyl malonate and vanillin. Therefore we applied this method for the 14C-labelling of ferulic acid esters. The 14C-labelled ferulic acid (FA-2-14C, 0.19 mCi/mM) was synthesized by deacetylating 4'-acetyl-ferulic acid-2-14C, which has been prepared from diethyl malonate-2-14C and vanillin. On the other hand, 14C-labelled ferulic acid triterpene esters (14C-FAE, 0.18 mCi/mM), which contained cycloartenol and 24-met hylenecycloartanol as major alcoholic constituents (77%), was synthesized by the esterification of the alcoholic constituents of the ferulic acid esters separated from the rice brain oil. The radiographic study of the thin layer chromatogram of the 14C-labelled compounds showed that these compounds are radiochemically pure.
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