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Concept
Glucosinolate
Summary
Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damaged. These natural chemicals most likely contribute to plant defence against pests and diseases, and impart a characteristic bitter flavor property to cruciferous vegetables.
Glucosinolates occur as secondary metabolites of almost all plants of the order Brassicales. This includes the economically important family Brassicaceae as well as Capparaceae and Caricaceae.
Outside of the Brassicales, the genera Drypetes and Putranjiva in the family Putranjivaceae, are the only other known occurrence of glucosinolates.
Glucosinolates occur in various edible plants such as cabbage (white cabbage, Chinese cabbage, broccoli), Brussels sprouts, watercress, horseradish, capers, and radishes where the breakdown products often contribute a significant part of the distinctive taste. The glucosinolates are also found in seeds of these plants.
Glucosinolates constitute a natural class of organic compounds that contain sulfur and nitrogen and are derived from glucose and an amino acid.
They are water-soluble anions and belong to the glucosides. Every glucosinolate contains a central carbon atom, which is bound to the sulfur atom of the thioglucose group, and via a nitrogen atom to a sulfate group (making a sulfated aldoxime). In addition, the central carbon is bound to a side group; different glucosinolates have different side groups, and it is variation in the side group that is responsible for the variation in the biological activities of these plant compounds.
The essence of glucosinolate chemistry is their ability to convert into an isothiocyanate (a "mustard oil") upon hydrolysis of the thioglucoside bond by the enzyme myrosinase.
The semisystematic naming of glucosinolates consists of the chemical name of the group "R" in the diagram followed by "glucosinolate", with or without a space.
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