Experiments in the biosynthesis of curcumin

Abstract

The biogenesis of natural diarylheptanoids is discussed, with particular reference to curcumin [1,7-bis-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione], the pigment of Curcuma Ionga rhizome. Methods for the isolation, characterisation, and degradation of curcumin, suitable for biosynthetic work, are reported. In administration of labelled precursors to C. Ionga,[1- and 3-¹⁴C]phenylalanine were incorporated into curcumin without scrambling of the label. [1- and 2-¹⁴C]-Acetate and -malonate were also incorporated, and the fractional distribution of label along the heptane chain was determined; the results do not provide satisfactory support for the expected biosynthetic scheme, in which two cinnamate units condense with one malonate unit. Other interpretations are discussed. [³H]-4-Hydroxy-3-methoxy-, -4-hydroxy-, and -3,4-dihydroxy-cinnamic acids were prepared, and supplied to C. Ionga with [¹⁴C]phenylalanine. The first two cinnamic acids are incorporated into curcumin significantly better than the last, although none was utilised quite as efficiently as phenylalanine.