Issue 0, 1980

Studies in the biosynthesis of [6]-gingerol, pungent principle of ginger (Zingiber officinale)

Abstract

The biosynthesis of [6]-gingerol has been investigated by the administration of labelled precursors to whole Zingiber officinale plants and to rhizome sections. The results show that phenylalanine is elaborated to ferulic acid which then condenses, in an unusual version of the ‘biological Claisen’ reaction, with malonate and hexanoate to yield [6]-dehydrogingerdione (11). Hexanoate is incorporated intact as shown by the location of label and the constancy of isotope ratios. Dihydroferulate is accepted, but loss of tritium shows it to be first dehydrogenated. Dione (11) is reduced in two steps to [6]-gingerol; in the preferred path, C[double bond, length half m-dash]O reduction precedes C[double bond, length half m-dash]C reduction, with (12) as intermediate, although dione (13) is also converted.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 2637-2644

Studies in the biosynthesis of [6]-gingerol, pungent principle of ginger (Zingiber officinale)

P. Denniff, I. Macleod and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1980, 2637 DOI: 10.1039/P19800002637

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