Diarylpropanoids from nutmeg and mace (Myristica fragrans Houtt.)

Abstract

Some diarylpropanoid (bis-C₆–C₃) type compounds have been isolated during the course of a search for the psychoactive components present in the seed (nutmeg) and aril (mace) of the fruit of Myristica fragrans Houtt. The presence of two different structural types, analogous to the β-O-4 ether and 2,3-dihydrobenzofuran types of dilignols, has been established. Six examples (I)–(III) and (V)–(VIII) of the former type and two of the latter, dehydrodi-isoeugenol (IX) and 5-methoxydehydrodi-isoeugenol (X) have been isolated and their structures established. Compounds (I), (II), and (V), have been synthesised and the relative configuration of the β-O-4 ethers has been established as erythro.