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Resorcylic Acid Lactone
Resorcylic acid lactones are a group of estrogenic compounds. They are lactones of resorcylic acid. Examples include the mycoestrogens (and synthetic analogues) zearalenone, zearalanone, zeranol (α-zearalanol), taleranol (β-zearalanol), α-zearalenol, and β-zearalenol β-Zearalenol is a nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in '' Fusarium spp''. It is the β epimer of α-zearalenol and along with α-zearalenol is a major metabolite of zearalenone formed main .... References Dihydroxybenzoic acids Lactones Mycoestrogens {{Chemistry-stub ...
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Estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal activity: estrone (E1), estradiol (E2), and estriol (E3). Estradiol, an estrane, is the most potent and prevalent. Another estrogen called estetrol (E4) is produced only during pregnancy. Estrogens are synthesized in all vertebrates and some insects. Their presence in both vertebrates and insects suggests that estrogenic sex hormones have an ancient evolutionary history. Quantitatively, estrogens circulate at lower levels than androgens in both men and women. While estrogen levels are significantly lower in males than in females, estrogens nevertheless have important physiological roles in males. Like all steroid hormones, estrogens readily diffuse across the cell membrane. Once inside the cell, they bind to and activate estrogen receptors (E ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken and/or new bonds formed. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, using the s ...
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Lactone
Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the corresponding hydroxycarboxylic acids, which takes place spontaneously when the ring that is formed is five- or six-membered. Lactones with three- or four-membered rings (α-lactones and β-lactones) are very reactive, making their isolation difficult. Special methods are normally required for the laboratory synthesis of small-ring lactones as well as those that contain rings larger than six-membered. Nomenclature Lactones are usually named according to the precursor acid molecule (''aceto'' = 2 carbon atoms, ''propio'' = 3, ''butyro'' = 4, ''valero'' = 5, ''capro'' = 6, etc.), with a ''-lactone'' suffix and a Greek letter prefix that specifies the number of carbon atoms in the heterocycle — that is, the distance between the relevant -OH ...
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Resorcylic Acid
Resorcylic acid is a type of dihydroxybenzoic acid. It may refer to: *3,5-Dihydroxybenzoic acid (α-Resorcylic acid) * 2,4-Dihydroxybenzoic acid (β-Resorcylic acid) * 2,6-Dihydroxybenzoic acid 2,6-Dihydroxybenzoic acid (γ-resorcylic acid) is a dihydroxybenzoic acid. It is a very strong acid due to its intramolecular hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element ... (γ-Resorcylic acid) {{chemistry index Dihydroxybenzoic acids ...
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Mycoestrogen
Mycoestrogens are xenoestrogens produced by fungi. They are sometimes referred to as mycotoxins. Among important mycoestrogens are zearalenone, zearalenol and zearalanol. Although all of these can be produced by various ''Fusarium'' species, zearalenol and zearalanol may also be produced endogenously in ruminants that have ingested zearalenone. Alpha-zearalanol is also produced semisynthetically, for veterinary use; such use is prohibited in the European Union. Mechanism of action Mycoestrogens act as agonists of the estrogen receptors, ERα and ERβ. Sources Mycoestrogens are produced by various strains of fungi, many of which fall under the genus ''Fusarium''. ''Fusarium'' fungi are filamentous fungi that are found in the soil and are associated with plants and some crops, especially cereals. Zearalenone is mainly produced by ''F. graminearum'' and ''F. culmorum'' strains, which inhabit different areas depending on temperature and humidity. ''F. graminearum'' prefers to inha ...
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Synthetic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Structural Analog
A structural analog (analogue in modern traditional English; Commonwealth English), also known as a chemical analog or simply an analog, is a compound having a structure similar to that of another compound, but differing from it in respect to a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced with other atoms, groups, or substructures. A structural analog can be imagined to be formed, at least theoretically, from the other compound. Structural analogs are often isoelectronic. Despite a high chemical similarity, structural analogs are not necessarily functional analogs and can have very different physical, chemical, biochemical, or pharmacological properties. In drug discovery, either a large series of structural analogs of an initial lead compound are created and tested as part of a structure–activity relationship study or a database is screened for structural analogs of a lead compound. Chemical analogues of il ...
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Zearalenone
Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some ''Fusarium'' and ''Gibberella'' species. Specifically, the ''Gibberella zeae ,'' the fungal species where zearalenone was initially detected, in its asexual/anamorph stage is known as ''Fusarium graminearum.'' 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. Particularly, ZEN is produced by ''Fusarium graminearum'', ''Fusarium culmorum'', '' Fusarium cerealis'', '' Fusarium equiseti'', ''Fusarium verticillioides'', and '' Fusarium incarnatum''. Zearalenone is the primary toxin that binds to estrogen receptors, causing infertility, abortion or other breeding problems, especially in swine. Often, ZEN is detected together with deoxynivalenol in contaminated samples and its toxicity needs to be considered in combination with the ...
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Zearalanone
Zearalanone (ZAN) is a semi-synthetic mycoestrogen that is a derivative of zearalenone (ZEN). Zearalanone is extracted from medical herbs and edible herbs alone with other substance called aflatoxins in the same time by a specific immunoaffinity column. Zearalanone has six analog. They are ZEN, zearalanone, α-zeralanol, β-zeralanol, α-zearalenol, and β-zearalenol. See also * α-Zearalenol * β-Zearalenol * Taleranol * Zeranol Zeranol (, , ) (brand names Frideron, Ralabol, Ralgro, Ralone, Zerano; developmental code names MK-188, P-1496), or zearanol, also known as α-zearalanol or simply zearalanol, is a synthetic nonsteroidal estrogen of the resorcylic acid lactone R ... References Estrogens Lactones Resorcinols {{biochem-stub ...
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Zeranol
Zeranol (, , ) (brand names Frideron, Ralabol, Ralgro, Ralone, Zerano; developmental code names MK-188, P-1496), or zearanol, also known as α-zearalanol or simply zearalanol, is a synthetic nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in fungi in the ''Fusarium'' genus and is used mainly as an anabolic agent in veterinary medicine. Zeranol is approved for use as a growth promoter in livestock, including beef cattle, under the brand name Ralgro (by Merck Animal Health) in the United States. In Canada, it is approved for use in beef cattle only. Its application is not approved for use in the European Union. However, it is marketed under the brand name Ralone in Spain. Although zeranol may increase cancer cell proliferation in already existing breast cancer, dietary exposure from the use of zeranol-containing implants in cattle is insignificant. Zeranol may be found as a contaminant in fungus-infected crops. It is 3 to 4 times more pote ...
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Taleranol
Taleranol (International Nonproprietary Name, INN, United States Adopted Name, USAN) (developmental code name P-1560), or teranol, also known as β-zearalanol, is a synthetic compound, synthetic, nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in ''Fusarium, Fusarium spp'' which was never marketed. It is the β epimer of zeranol (α-zearalanol) and is a major metabolite of zeranol but with less biological activity. See also * α-Zearalenol * β-Zearalenol * Zearalanone * Zearalenone References

Lactones Mycoestrogens Mycotoxins Resorcinols {{genito-urinary-drug-stub ...
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α-zearalenol
α-Zearalenol is a nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in '' Fusarium spp''. It is the α epimer of β-zearalenol and along with β-zearalenol is a major metabolite of zearalenone formed mainly in the liver but also to a lesser extent in the intestines during first-pass metabolism. A relatively low proportion of β-zearalenol is formed from zearalenone compared to α-zearalenol in humans. α-Zearalenol is about 3- to 4-fold more potent as an estrogen relative to zearalenone. See also * Taleranol (β-zearalanol) * Zeranol (α-zearalanol) * Zearalanone Zearalanone (ZAN) is a semi-synthetic mycoestrogen that is a derivative of zearalenone Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some ''Fusarium'' and ''Gibberella'' species. Specificall ... References {{DEFAULTSORT:Zearalenol, alpha- Lactones Mycoestrogens Mycotoxins Resorcinols ...
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