MOLECULE

Glucobrassicin

Glucobrassicin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucobrassicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Glucobrassicin is a bitter tasting compound. Outside of the human body, Glucobrassicin has been detected, but not quantified in, several different foods, such as cauliflowers, broccoli, horseradish, chinese mustards, and swedes. This could make glucobrassicin a potential biomarker for the consumption of these foods. A single glucosylation occurs attaching a glucose molecule to the indole hydroximate through a thioether linkage. Several derivatives of glucobrassicin are known. The biosynthesis of glucobrassicin begins with tryptophan produced through several steps from the Shikimic acid pathway compound, chorismic acid. The compound itself was first isolated from Brassica plants, hence the ending of the name. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue or in intact plants. Currently, the following six derivatives are known from plants:1-Methoxyglucobrassicin (neoglucobrassicin)4-Hydroxyglucobrassicin4-Methoxyglucobrassicin1,4-Dimethoxyglucobrassicin1-Sulfoglucobrassicin6'-IsoferuloylglucobrassicinThe three first mentioned derivatives are as frequent in crucifers as glucobrassicin itself. Tryptophan is converted to indole-3-acetaldoxime (IAOx) by cytochrome p450 enzymes (the redundant CYP92B3 and CYP79B3 in Arabidopsis thaliana) using NADPH and molecular Oxygen. Glucobrassicin is expected to be in Cannabis as all living plants are known to produce and metabolize it.