Zearalenone
Encyclopedia
Zearalenone also known as RAL and F-2 mycotoxin
, is a potent estrogenic metabolite
produced by some Gibberella
species.
Several Fusarium species produce toxic substances of considerable concern to livestock and poultry producers: namely, deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone
Zearalenone is the primary toxin causing infertility
, abortion
or other breeding problems, especially in swine.
Zearalenone is heat-stable and is found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum and also in bread.
and progressively more so in benzene
, acetonitrile
, methylene chloride, methanol
, ethanol
, and acetone
. It is also soluble in aqueous alkali.
, acetonitrile
, or ethyl acetate
followed by a range of different clean-up procedures that depend in part on the food and on the detection method in use. TLC methods and HPLC are commonly used. HPLC alone is not sufficient as it may often yield false positive results. Today HPLC-MSMS analysis is used to quantify and confirm the presence of zearalenone.
The TLC method for zearalenone is: normal phase silica gel plates, the eluent: 90% dichloromethane
, 10% v/v acetone; or reverse phase C18 silica plates; the eluent: 90% v/v methanol
, 10% water. Zearalenone gives unmistakable blue luminiscence under UV.
Mycotoxin
A mycotoxin is a toxic secondary metabolite produced by organisms of the fungus kingdom, commonly known as molds. The term ‘mycotoxin’ is usually reserved for the toxic chemical products produced by fungi that readily colonize crops...
, is a potent estrogenic metabolite
Metabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
produced by some Gibberella
Gibberella
Gibberella is a genus of fungus in the Nectriaceae family. In 1926, Japanese scientists observed that rice plants infected with Gibberella had abnormally long stems . A substance, gibberellin, was derived from this fungus...
species.
Several Fusarium species produce toxic substances of considerable concern to livestock and poultry producers: namely, deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone
Zearalenone is the primary toxin causing infertility
Infertility
Infertility primarily refers to the biological inability of a person to contribute to conception. Infertility may also refer to the state of a woman who is unable to carry a pregnancy to full term...
, abortion
Abortion
Abortion is defined as the termination of pregnancy by the removal or expulsion from the uterus of a fetus or embryo prior to viability. An abortion can occur spontaneously, in which case it is usually called a miscarriage, or it can be purposely induced...
or other breeding problems, especially in swine.
Zearalenone is heat-stable and is found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum and also in bread.
Chemical and physical properties
Zearalenone is a white crystalline solid. It exhibits blue-green fluorescence when excited by long wavelength UV light (360) and a more intense green fluorescence when excited with short wavelength UV light (260 nm). In methanol, UV absorption maxima occur at 236 (e =29,700), 274 (e =13,909) and 316 (e =6,020). Maximum fluorescence in ethanol occurs with irradiation at 314nm and with emission at 450nm. Solubility in water is about 0.002g/100ml. It is slightly soluble in hexaneHexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...
and progressively more so in benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
, acetonitrile
Acetonitrile
Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...
, methylene chloride, methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
, ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
, and acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
. It is also soluble in aqueous alkali.
Sampling and analysis
In common with other mycotoxins sampling food commodities for zearalenone must be carried out to obtain samples representative of the consignment under test. Commonly used extraction solvents are aqueous mixtures of methanolMethanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
, acetonitrile
Acetonitrile
Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...
, or ethyl acetate
Ethyl acetate
Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and cigarettes...
followed by a range of different clean-up procedures that depend in part on the food and on the detection method in use. TLC methods and HPLC are commonly used. HPLC alone is not sufficient as it may often yield false positive results. Today HPLC-MSMS analysis is used to quantify and confirm the presence of zearalenone.
The TLC method for zearalenone is: normal phase silica gel plates, the eluent: 90% dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...
, 10% v/v acetone; or reverse phase C18 silica plates; the eluent: 90% v/v methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
, 10% water. Zearalenone gives unmistakable blue luminiscence under UV.
External links
- Detailed information about mycotoxins
- INTERNATIONAL PROGRAMME ON CHEMICAL SAFETY review on Zearalenone
- MSDS Zearalenone safety data sheet