The biosynthesis of laurifinine

Abstract

The incorporation of (±)-nor-laudanosoline, (±)-N-nor-protosinomenine, (±)-N-nor-orientaline, (±)-N-nor-reticuline, and N-[2-(3-hydroxy-4-methoxyphenyl) ethyl]-2-(4'-hydroxyphenyl) ethylamine into laurifinine has been studied and the specific utilisation of the (±)-N-norprotosinomenine demonstrated. Double labelling experiments with (±)-[1-³H, 4'-methoxy-¹⁴C]-, and (±)-[1-³H, 7-methoxy-¹⁴C]-N-norprotosinomenines showed that 4' and 7, OMe groups and the H atom at the asymmetric centre of the precursor are retained in the bioconversion into laurifinine. Parallel experiments with (+)- and (-)-N-norprotosinomenine demonstrated specific utilisation of (+)-isomer into laurifinine.