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Issue 0, 1973
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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.

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Article type: Paper
DOI: 10.1039/P19730002379
J. Chem. Soc., Perkin Trans. 1, 1973, 2379-2388

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    Experiments in the biosynthesis of curcumin

    P. J. Roughley and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1973, 2379
    DOI: 10.1039/P19730002379

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