S-Methyl Methanethiosulfonate, Bio-antimutagen in Homogenates of Cruciferae and Liliaceae Vegetables

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The isolation of a new type of bio-antimutagen, S-methyl methanethiosulfonate (MMTS), from cauliflower (Brassica oleracea var. botrytis) and the distribution and formation of MMTS in Cruciferae and Liliaceae vegetables are described. For the separation and purification, cauliflower curds were homogenized, extracted with acetone, and then purified by organic solvent extraction and by various processes of chromatographic separation. The chemical structure of an active principle was identified as MMTS by GC-MS and ¹H-NMR analyses. MMTS was widely found in vegetable homogenates of the Cruciferae and Liliaceae species, and is formed from its precursor, S-methyl-L-cysteinesulfoxide (SMCS), by wounding the vegetables tissues. Wounding may induce C-S lyase, which converts SMCS to MMTS. The amount of MMTS formed was affected by the pH value for C-S lyase, but not by the SMCS content in a tissue homogenate.