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structure of glucosinolates

Glucosinolate structure


Glucosinolates  Glucosinolates are the main secondary, sulphur-containing metabolites found in Brassica crops. The glucosinolate molecule consists of a β-thioglucose unit, a sulphonated oxime unit and a variable side chain, derived from an amino acid (Fig 1). Glucosinolates with more than 120 variable side chain structures have been described (Fahey et al, 2001), although only about 16 of these are commonly found within crop plants.
Several Brassica species are important feed ingredients and some species are also commonly used in human nutrition such as cauliflower, cabbages, broccoli, Brussels sprouts,... Glucosinolates

Epidemiological studies suggest that glucosinolates provide health benefits, particularly with regard to a reduction in risk of cancer (Talalay & Fahey, 2001). The presence of glucosinolates in the seeds of oilseed cruciferous crops on the other hand, significantly reduces the livestock feeding quality of the meal left following oil extraction from seeds (Fenwick et al, 1989).
Another reason for interest in glucosinolates is their potential for use in alternative pest management systems because of the insecticidal, nematicidal, fungicidal properties of their breakdown products, mainly isothiocyanates.

Using plant-produced chemicals in agricultural and horticultural practices (biofumigation) could minimize synthetic pesticide use, reduce the associated potential for environmental contamination, and contribute to a more sustainable agricultural system.



NORMES AND LEGISLATIONS (maximum level allowed in food) :

Glucosinolates are present in all parts of the plants, with the highest concentrations found in seeds. Data on the toxicity of individual glucosinolates for food-producing animal species are very limited, and in most cases only the total glucosinolate content in a given feed material, measured indirectly through quantification of hydrolysable glucose, is available.

Only for rapeseed meal or press cakes comprehensive feeding trials in animal farms have been conducted, resulting in the recommendation to restrict the total glucosinolate content to 1 - 1.5 mmol per kg feed for monogastric animals, and to even lower concentrations in feeds for young animals.
Concentrations in animal-derived products are much lower than those found in vegetables for human consumption, and are unlikely to induce advers health effects in consumers (EFSA (European Food Safety Authority) , 2008).



As glucosinolates are an essential quality aspect of several important feed ingredients and vegetables, the research at CODA-CERVA was focussed on the quantitative and qualitative changes of these natural compounds induced by abiotic stress e.g. ozone.glucosinolates




Karine Vandermeiren


- Vandermeiren, K., De Bock, M., Horemans, N., Guisez, Y., Ceulemans, R., De Temmerman, L., 2012. Ozone effects on yield quality of spring oilseed rape and broccoli. Atmospheric environment. 47, 76-83.

- De Bock, M., Op de Beeck, M., De Temmerman, L., Guisez, Y., Ceulemans, R., Vandermeiren, K., 2011. Ozone dose-response relationships for spring oilseed rape and broccoli. Atmospheric Environment 45, 1759-1765.

- Vandermeiren K., Pleijel H. (2011). Effects of ozone on food and feed quality. In: Ozone pollution: a hidden threat to food security. Report prepared by the ICP Vegetation. Eds: Mills G., Harmens H.-CEH. P 53-60

- Op de Beeck, M., De Bock, M., Vandermeiren, K., De Temmerman, L., Ceulemans, R., 2010. A comparison of two stomatal conductance models for ozone flux modelling using data flux modelling using data from two Brassica species. Environmental Pollution 158, 3251-3260.


- Press release in Food Navigator, 01-July-2009. "New research shows ozone's effects on oil seed rape" By Caroline Scott-Thomas.

- Vandermeiren K., Harmens H., Mills G., De Temmerman L.(2009) Impacts of ground-level ozone on crop production in a changing climate. In: Climate Change and Crops. S.N. Singh (Ed.), Springer-Verlag Berlin Heidelberg, 213-243.
- Vandermeiren K., De Temmerman L. (2009) Impact of tropospheric ozone pollution on food and feed quality of Brassica species. VAR Scientific report 2007-2008, 94-98.
- Vandermeiren K., De Bock M., Horemans N., Gielen B. (2009) Impact of tropospheric ozone on glucosinolate and vitamin C content of oilseed rape and broccoli. In: Sulfur metabolism in plants. A. Sirko, L.J. De Kok, S. Haneklaus, M.J. Hawkesford, H. Rennenberg, K. Saito, E. Schnug and I. Stulen (Eds), Backhuys Publischers, Leiden, Margraf Publishers, Weikersheim, 245-252.

- Gielen B., Vandermeiren K., Horemans N., D'Haese D., Serneels R., Valcke R.(2006) Chlorophyll a fluorescence imaging of ozone-stressed Brassica napus L. plants differing in glucosinolate concentrations . Plant Biology 8, 698-705.