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Zur Biosynthese des Chinazolinalkaloids Arborin

Siegfried Johne, Konrad Waiblinger, Detlef Gröger · European Journal of Biochemistry · 1970

The indian plant Glycosmis arborea (Roxb.) DC. (Rutaceae) contains alkaloids of different types. The main alkaloid of the Glycosmis leaves is the 4‐quinazolone derivative arborine (VI). Previously it has been shown that labelled anthranilic acid (X) and phenylalanine (XI) are specifically incorporated into this alkaloid. This study was performed in order to elucidate the possible pathway of arborine formation in vivo. During these investigations an improved procedure for the isolation of arborine was developed.The following results were obtained: After feeding of [14CH3]methionine the N‐methyl group of VI was specifically labelled. The same result was obtained after the application of [14CH]3N‐methylanthranilic acid. These results seem to indicate that anthranilic acid gets methylated prior to the condensation with phenylalanine which leads to VI. But on the other hand after feeding of [2‐14C] glycosminine (V) labelled arborine was also isolated. However in this case the incorporation rate was much lower compared with those of the two other mentioned precursors. It should be mentioned that V is only sparingly soluble in solvents suitable for feeding experiments. The N‐1 atom of VI

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