Glucosinolate

The mustard oil glycosides, glucosinolates also belong to the group of glycosides. Since the aglycone is bound via a sulfur atom in the sugar part ( glycone ), it is referred in more detail by a thioglycoside.

Glucosinolates are sulfur - and nitrogen-containing chemical compounds that are formed from amino acids. These phytochemicals give vegetables such as radish, horseradish, mustard, cress, Nasturtium and cabbage the somewhat bitter taste.

There are around 120 different glucosinolates, which differ only in the aglycone moiety. As sugar always occurs on glucose. The cleavage enzyme of the glucosinolate is myrosinase, that is spatially separated present in the cells. In case of violation of the cells ( chewing or cutting) myrosinase and glucosinolates come together, which are thereby hydrolyzed to isothiocyanates. Mustard oils are either non-volatile and pungent taste or they are volatile and pungent smell.

Since glucosinolates act as constitutive defense compounds ( phytoanticipins ) against being eaten by animals, can be adopted in the context of evolutionary theory that this substance group was formed in the course of evolution for this purpose. According to recent findings, these flavors help prevent infections and support cancer prevention, such as sulforaphane or Iberin. Glucosinolates from Capuchin Kress herb and horseradish root are combined used in medicine as a phytotherapeutic agent for the treatment and prophylaxis of respiratory and urinary tract infections.

Under certain conditions, can arise from glucosinolates and thiocyanates form. This can at high concentrations or with a high intake, especially after consumption of large amounts of carbon ( with the glucosinolate glucobrassicin ), as occurs in times of need, for goiter in humans and animals lead ( goitrogenic substance). This bind the thiocyanate ions iodide ions that are no longer or only in small quantities are then for the synthesis of the thyroid hormone thyroxine available.

For glucosinolates and their hydrolysis metabolites and chemoprotective effects against various carcinogens were detected. They block the tumor formation in a number of tissues and organs such as the liver, colon, mammary glands, pancreas and others.

Use in medicine

Mustard oils (eg, allyl isothiocyanate ) as a locally acting therapeutic skin irritant ( Rubefacientia ) are used. They may have a strong antibacterial.

Preparations of mustard oil-bearing plants also providing therapeutic uses. Nasturtium about acts due to their content of benzyl mustard in vitro bacteriostatic ( against gram-positive and gram-negative bacteria), virustatic and antimycotic.

Scientifically proven is also the antimicrobial action of mustard oils in horseradish. The essential oil contains allyl isothiocyanate (about 90% ) and 2- Phenylethylensenföl. Depending on the dose of horseradish in vitro bacteriostatic or bactericidal. The allyl isothiocyanate from horseradish root shows good efficacy in gram-negative spectrum, while the 2- Phenylethylsenföl from the horseradish root has an extended spectrum of activity against gram positive.

Glucosinolates from Capuchin Kress herb and horseradish root are combined in practice used as a phytotherapeutic agent for the treatment and prophylaxis of respiratory and urinary tract infections. In vitro studies indicate that a combination of the two metabolites has a broad antibacterial spectrum against 13 clinically relevant bacterial strains.

Studies at the Institute of Medical Virology, University of Giessen in 2010 revealed that mustard oils from nasturtium and horseradish multiplication of influenza viruses can inhibit the type H1N1. Proliferation was inhibited in the in vitro model with human lung cells by about 90 percent. As early as 1958 has been proven in scientific studies on exembryonierten egg under the influence of mustard oils from nasturtium and horseradish strongly inhibits the replication of influenza viruses.

Occurrence and biochemical characteristics

Glucosinolates come into Central Europe without exception in the mustard family. Otherwise, they are common in the caper plants, occasionally they occur in Capuchin Kress plants, spurge and other plant taxa. Glycosinolate be cleaved by myrosinase to glucose, hydrogensulfate HSO4 -, and one of the following aglycones: isothiocyanate, thiocyanate, nitrile, or oxazolidine -2-thione. This can cause symptoms of poisoning ( mostly ) higher concentrations:

• Isothiocyanates ( chemically: R- N = C = S) irritate the lining, but are usually included in such small quantities that no further damage is caused. If Glycosinolate be recorded and broken down in the intestine to isothiocyanates, they can have a negative impact on the production of thyroid hormones.

• Oxazolidine -2- thione resulting from isothiocyanates from glucosinolates with 2-hydroxy acid side groups, such as the glucosinolate progoitrin via the intermediate stage of goitrin. Oxazolidines -2-thiones interfere with the growth and increase the likelihood of goiter formation ( engl. ' goiter '). Blocking the thyroid function by the inhibition of iodine uptake in thyroxine precursor and by the inhibition of thyroxine secretion from the thyroid gland.
• Nitriles (R- C = N) interfere with the growth, cause liver and kidney damage, and in severe cases lead to liver necrosis.
• Thiocyanate (R- S- C = N) to prevent the iodine uptake in the thyroid, thereby decreased tyrosine iodination and decreased synthesis of thyroxine.