Biosynthesis of tetrahydropalmatine and palmatine

Abstract

The incorporation of (±)-norlaudanosoline, norprotosinomenine, nororientaline, norlaudanidine, reticuline and laudanosine into tetrahydropalmatine and palmatine has been studied, and specific utilization of reticuline demonstrated. Feeding of (±)-[N-methyl-¹⁴C] reticuline showed that C atom 8 of tetrahydropalmatine and palmatine are formed by oxidative cyclisation of the N-Me group of reticuline. Parallel experiments with (R)-; and (S)-, reticulines demonstrated specific incorporation of (R)- isomer into these bases. Feeding experiments also revealed that the plants can convert tetrahydropalmatine into palmatine with high efficiency.