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The distribution of hydroxycinnamoylmalic acids (HCM acids) in 25 species and 2 subspecies of Papaveraceae and Fumariaceae representing 14 genera was investigated by HPLC and subsequent diode array detection (DAD). In case of similar chromatographic and UV-spectrometric behavior of HCM acids and other hydroxycinnamic acid derivatives liquid chromatography-thermospray/mass spectrometry (LC-TSP/MS) was used for positive identification. Ten of the species were found to contain caffeoyl-, p-coumaroyl-. and feruloylmalic acid whereas Chelidonium majus only showed the presence of caffeoylmalic acid. Sinapoylmalic acid could not be detected. The quantitative determ ination by HPLC at 330 nm yielded the highest content of caffeoylmalic acid for Fumciria officinalis and F. capreolata, and the lowest for Chelidonium majus. Isolated HCM acids showed positive optical rotation for members of the Papaveraceae and negative values for m em bers of the Fum ariaceae. This points to an esterification of hydroxycinnam ic acids with (-)-ʟ -malic acid for the Papaveraceae and with (+)-ᴅ-malic acid for the Fumariaceae. For plants containing HCM acids the contents of free l - and ᴅ-malic acid w ere determ ined enzym atically Yields of ʟ-malic acid were higher for Papaveraceae than for Fum ariaceae; ᴅ-malic acid was detectable only in traces for all investigated species. The Fum ariaceae showed a ca. 1:1 relationship between free ʟ-malate and esterified ᴅ-malate. This suggests an enzym atic racem ization of the original ʟ-malate and a subsequent esterification of the intermediate ᴅ-malate with hydroxycinnamic acids

Distribution and Stereochemistry of Hydroxycinnamoylmalic Acids and of Free Malic Acids in Papaveraceae and Fumariaceae