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Studies on the Biosynthesis of Some Furocoumarins Present in Ruta graveolens

G. Caporale, F Dall’Acqua, A. Capozzi, S. Marciani, R. Michael Crocco

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Abstract

The biosynthesis of some furocoumarins present in Ruta graveolens has been studied administering labeled psoralen, xanthotoxin, rutaretin, marmesin and 7-hydroxycoumarin-derivatives. The results obtained indicate that the biosynthetic pathway involves not only psoralen, but also xanthotoxin and bergapten, by means of methoxylation or demethoxylation reactions. Moreover results achieved from administering rutaretin demonstrate that this substance is a new very effective natural precursor for xanthotoxin; in a parallel way marmesin is incorporated into psoralen. The reported results indicate that also at the stage of natural 4′,5′-dihydrofurocoumarins intermediates an interconversion can occur. Finally the essential role of umbelliferone in the biosynthesis of furocoumarins has been confirmed.

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The biosynthesis of some furocoumarins present in Ruta graveolens has been studied administering labeled psoralen, xanthotoxin, rutaretin, marmesin and 7-hydroxycoumarin-derivatives. The results obtained indicate that the biosynthetic pathway involves not only psoralen, but also xanthotoxin and bergapten, by means of methoxylation or demethoxylation reactions. Moreover results achieved from administering rutaretin demonstrate that this substance is a new very effective natural precursor for xanthotoxin; in a parallel way marmesin is incorporated into psoralen. The reported results indicate that also at the stage of natural 4′,5′-dihydrofurocoumarins intermediates an interconversion can occur. Finally the essential role of umbelliferone in the biosynthesis of furocoumarins has been confirmed.

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Available abstract

The biosynthesis of some furocoumarins present in Ruta graveolens has been studied administering labeled psoralen, xanthotoxin, rutaretin, marmesin and 7-hydroxycoumarin-derivatives. The results obtained indicate that the biosynthetic pathway involves not only psoralen, but also xanthotoxin and bergapten, by means of methoxylation or demethoxylation reactions. Moreover results achieved from administering rutaretin demonstrate that this substance is a new very effective natural precursor for xanthotoxin; in a parallel way marmesin is incorporated into psoralen. The reported results indicate that also at the stage of natural 4′,5′-dihydrofurocoumarins intermediates an interconversion can occur. Finally the essential role of umbelliferone in the biosynthesis of furocoumarins has been confirmed.

Key concepts: Furocoumarins, Psoralen, Bergapten, Umbelliferone, Ruta graveolens, Chemistry, Biosynthesis, Furocoumarin

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