Indole derivatives with anticarcinogenic action from glucosinolates (GSLs) in food

H. Schmandke, Nuthetal

Indole containing GSLs in vegetables, primarily of the family Brassicaceae, are not degraded by myrosinase to stable isothiocyanates. Indole-3-ylmethyl-GSL e.g. is converted into indole-3-carbinol (I3C) which, under the influence of acidic gastric juice, completely undergoes oligomerization to the metabolites 3,3’-diindolylmethane (I33’), indolylcarbazol (ICZ), 2-(indole-3-ylmethyl)-3,3’-diindolylmethane (LT), 5,6,11,12,17,18-hexahydrocyclonona-triindole (CT) and 1-(3-hydroxymethyl)-indolyl-3-indolylmethane (HIIM).

In animal studies I33’ was detected in feces, serum and liver. LT, HIIM and ICZ have been found in the liver while I3C is not detectable in the organism. After oral administration of [5-3 H] I3C, 75 % of the radioactivity are predominantly excreted via feces (77 %) and urine.

An anticarcinogenic effect of 13C has been shown in animals and of I3C and its metabolites I33’, CT, LT and ICZ in human cancer-cell lines. In cancer cells, I3C is converted to conjugates, I33’, indole-3-carboxaldehyde and -carboxylic acid. Toxicological data are avilable for I3C and I33’. I3C was also used in preliminary human trials (tolerance tests). Results of clinical studies of I3C may soon be expected.

Key words: Indole derivates / glucosinolates / anticancerinogenic effect

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