Indole glucosinolate breakdown and its biological effects |
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Authors: | Niels Agerbirk Martin De Vos Jae Hak Kim Georg Jander |
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Institution: | (1) Faculty of Life Science, University of Copenhagen, 1871 Frederiksberg C, Denmark;(2) Boyce Thompson Institute for Plant Research, 1 Tower Road, Ithaca, NY 14853, USA;(3) Present address: Monsanto Company, St. Louis, MO, USA |
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Abstract: | Most species in the Brassicaceae produce one or more indole glucosinolates. In addition to the parent indol-3-ylmethylglucosinolate
(IMG), other commonly encountered indole glucosinolates are 1-methoxyIMG, 4-hydroxyIMG, and 4-methoxyIMG. Upon tissue disruption,
enzymatic hydrolysis of IMG produces an unstable aglucone, which reacts rapidly to form indole-3-acetonitrile and indol-3-ylmethyl
isothiocyanate. The isothiocyanate, in turn, can react with water, ascorbate, glutathione, amino acids, and other plant metabolites
to produce a variety of physiologically active indole compounds. Myrosinase-initiated breakdown of the substituted indole
glucosinolates proceeds in a similar manner to that of IMG. Induction of indole glucosinolate production in response to biotic
stress, experiments with mutant plants, and artificial diet assays suggest a significant role for indole glucosinolates in
plant defense. However, some crucifer-feeding specialist herbivores recognize indole glucosinolates and their breakdown products
as oviposition and/or feeding stimulants. In mammalian diets, IMG can have both beneficial and deleterious effects. Most IMG
breakdown products induce the synthesis of phase 1 detoxifying enzymes, which may in some cases prevent carcinogenesis, but
in other cases promote carcinogenesis. Recent advances in indole glucosinolate research have been fueled by their occurrence
in the well-studied model plant Arabidopsis thaliana. Knowledge gained from genetic and biochemical experiments with A. thaliana can be applied to gain new insight into the ecological and nutritional properties of indole glucosinolates in other plant
species. |
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Keywords: | Ascorbigen Brassicaceae Cancer Indole-3-acetonitrile Indole-3-carbinol Indol-3-ylmethyl isothiocyanate Insect Myrosinase |
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