Glucosinolate Standards

Glucosinolates are secondary plant metabolites that occur in many food and medicinal plants, e.g., horseradish, radish, wasabi, nasturtium, broccoli, maca, rocket, capers, or papaya. They are responsible for the pungency & bitter taste and the protection of these plants against herbivores. Glucosinolates exert antimicrobial, antiviral, antifungal and anticarcinogenic activities. Herbal medicines containing nasturtium and horseradish root, for example, are used to treat sinusitis, bronchitis and urinary tract infections.^[1]

Upon ingestion, glucosinolates consist of a central carbon atom bound to a glucose via a sulphur atom and to a sulphate group via a nitrogen atom. Their substance-specific side chain depends on the amino acid involved in the initial phase of their biosynthesis. In the intact plant cell, the enzyme myrosinase is kept in a separate compartment, but can be released e.g. during cutting or chewing. As soon as glucosinolates encounter myrosinase and water, the glucose moiety is cleaved. Various spontaneous reactions occur, resulting in the formation of isothiocyanate, thiocyanates, nitriles or oxazolidine 2-thiones such as the goitrin (5-vinyloxazolidine-2-thione).^[2]

In animals, these metabolites can inhibit uptake of iodine and biosynthesis of the thyroid hormones T3 & T4, leading to hypothyroidism and enlargement of the thyroid gland. As a result, changes in thyroid function associated with growth retardation and impaired fertility can be observed. Thus, in 2008, the European Food Safety Authority (EFAS) published their opinion on glucosinolates as undesirable substances in animal feed initiated by the European Commission. Although glucosinolates vary in their toxicity, adverse effects in animals have been correlated with the amount of total glucosinolates in the diet. The degradation products mentioned above inhibit uptake of iodine and biosynthesis of the thyroid hormones T3 & T4, leading to hypothyroidism and enlargement of the thyroid gland. As a result, changes in thyroid function associated with growth retardation and impaired fertility can be observed. Some degradation products can cause irritation in the gastrointestinal tract and affect liver and kidney function. However, data on the toxicity of individual glucosinolates are limited. Usually, techniques and procedures are used to remove intact glucosinolates as well as their degradation products, e.g., by soaking the press cakes with copper sulphate solutions and water extraction. Furthermore, the EFSA emphasises the importance of validated analytical methods for analyses of the total glucosinolate in feed materials.^[3]

Whether for quality control of food & feed or pharmacological research: PhytoLab is offering you an outstanding portfolio of highly purified and well characterized phyproof reference standards for a reliable quantitative analysis of glucosinolates and their degradation products. As the sulphate group is negatively charged, we establish glucosinolate standards in the form of stable potassium salts.^[4]

Find your compound below:

[1] (a) G. Williams, J.C. Craig Current opinion in infectious diseases 2009, 22 (1), 72-76; (b) B.W. Trautner, R.A. Hull, R.O. Darouiche Current opinion in infectious diseases 2005, 18 (1), 37-41; (c) U. Albrecht, K.H. Goos, B. Schneider Current medical research and opinion 2007, 23 (10), 2415-2422.

[2] I. Blažević, S. Montaut, F. Burčul, C. E. Olsen, M. Burow, P. Rollin, N. Agerbirk, Phytochemistry 2020, 169, 112100. https://doi.org/10.1016/j.phytochem.2019.112100

[3] Opinion of the Scientific Panel on Contaminants in the Food Chain on a request from the European Commission on glucosinolates as undesirable substances in animal feed, The EFSA Journal 2008, 590, 1–76. https://www.efsa.europa.eu/en/efsajournal/pub/590

[4] Due to the negative charge of the glucosinolate core structure the counter ion has to be taken into account. For all phyproof® glucosinolates characterized as primary reference standard, we determine potassium quantitatively and consider it as an impurity in the calculation of the absolute content, which therefore refers to the pure glucosinolate only.