Dicoumarol biosynthesis: origin of the methylene bridge

Abstract

The origin of the methylene-bridge carbon atom of dicoumarol was investigated. In the absence of exogenous formaldehyde, Penicillium jenseni converted o-coumaric acid to 4-hydroxycoumarin but little dicoumarol was produced. Further experiments with potential C1 donors such as choline, serine, and methionine confirmed that dicoumarol was probably an artefact produced by reaction between microbiologically formed 4-hydroxycoumarin and exogenous formaldehyde.