Ω-OXYGENATED PRENYLATED COUMARINS FROM FERULA COMMUUNIS

Article abstract of DOI:10.1016/0031-9422(88)80778-7

From the toxic variety of Ferula communis, derivatives of the prenylated coumarins ferulenol and ferperin bearing an oxygen function (hydroxyl, acetoxyl, aldehydic carbonyl) at the ω-position have been isolated.The structures of the coumarins were established by spectral methods and by chemical reactions.Photooxygenation of ferulenol and (E)ω-hydroxyferulenol gave o-hydroxyphenylglyoxylic esters, resulting from the oxidative decarbonylation of the 4-hydroxycoumarinic nucleus and losss of the prenyl side chain.Ethyl o-hydroxyphenylglyoxylacetate was also isolated from the plant extract, suggesting that a reaction of this type might be responsible for the degradation of the prenylated coumarins in plant samples and extracts of Ferula commuunis. Key Word Index-- Ferula communis; Umbelliferae; prenylated coumarins; ferulenol; ferprenin.