The active part of the [6]-gingerol molecule in mutagenesis

A study was performed to discover the active part in mutagenesis of [6]-gingerol, a mutagen contained in ginger Zingiber officinale (Nakamura and Yamamoto, 1982). [6]-Shogaol was isolated from the ginger by column chromatography on silica gel. [6]-Shogaol was much less mutagenic (1 X 10(3) revertants/10(8) viable cells/700 microM) than [6]-gingerol (1 X 10(7) of the same units). Mutation frequencies of their related compounds were 4 X 10(1) for zingerone, 1 X 10(7) for 3-hydroxymyristic acid and 3 X 10(2) for 12-hydroxystearic acid. Curcumin, and myristic, stearic and oleic acids had no mutagenicity; and diacetone alcohol and butyroin were suppressible for mutation. It was inferred from these results that the active part of [6]-gingerol was the aliphatic chain moiety containing a hydroxy group.