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Myrosin
Myrosinase (, ''thioglucoside glucohydrolase'', ''sinigrinase'', and ''sinigrase'') is a family of enzymes involved in plant defense against herbivores, specifically the mustard oil bomb. The three-dimensional structure has been elucidated and is available in the PDB (see links in the infobox). A member of the glycoside hydrolase family, myrosinase possesses several similarities with the more ubiquitous O-glycosidases. However, myrosinase is the only known enzyme found in nature that can cleave a thio-linked glucose. Its known biological function is to catalyze the hydrolysis of a class of compounds called glucosinolates. Myrosinase activity Myrosinase is regarded as a defense-related enzyme and is capable of hydrolyzing glucosinolates into various compounds, some of which are toxic. Mechanism Myrosinase catalyzes the chemical reaction :a thioglucoside + H2O \rightleftharpoons a sugar + a thiol Thus, the two substrates of this enzyme are thioglucoside and H2O, whereas its ...
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Glucosinolates
Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damaged. These natural chemicals most likely contribute to plant defence against pests and diseases, and impart a characteristic bitter flavor property to cruciferous vegetables. Occurrence Glucosinolates occur as secondary metabolites of almost all plants of the order Brassicales. This includes the economically important family Brassicaceae as well as Capparaceae and Caricaceae. Outside of the Brassicales, the genera '' Drypetes'' and '' Putranjiva'' in the family Putranjivaceae, are the only other known occurrence of glucosinolates. Glucosinolates occur in various edible plants such as cabbage (white cabbage, Chinese cabbage, broccoli), Brussels sprouts, watercress, arugula, horseradish, capers, and radishes where the breakdo ...
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Plant Defense Against Herbivory
Plant defense against herbivory or host-plant resistance is a range of adaptations Evolution, evolved by plants which improve their fitness (biology), survival and reproduction by reducing the impact of herbivores. Many plants produce secondary metabolites, known as Heterotelergones, allelochemicals, that influence the behavior, growth, or survival of herbivores. These chemical defenses can act as repellents or toxins to herbivores or reduce plant digestibility. Another defensive strategy of plants is changing their attractiveness. Plant perception (physiology), Plants can sense being touched, and they can respond with strategies to defend against herbivores. Plants alter their appearance by changing their size or quality in a way that prevents overconsumption by large herbivores, reducing the rate at which they are consumed. Other defensive strategies used by plants include escaping or avoiding herbivores at any time in any placefor example, by growing in a location where plants ...
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Glucosinolate
Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damaged. These natural chemicals most likely contribute to plant defence against pests and diseases, and impart a characteristic bitter flavor property to cruciferous vegetables. Occurrence Glucosinolates occur as secondary metabolites of almost all plants of the order Brassicales. This includes the economically important family Brassicaceae as well as Capparaceae and Caricaceae. Outside of the Brassicales, the genera '' Drypetes'' and '' Putranjiva'' in the family Putranjivaceae, are the only other known occurrence of glucosinolates. Glucosinolates occur in various edible plants such as cabbage (white cabbage, Chinese cabbage, broccoli), Brussels sprouts, watercress, arugula, horseradish, capers, and radishes where the breakdown products of ...
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Sinapis Alba
White mustard (''Sinapis alba''), also called yellow mustard, is an annual plant of the cabbage family. It is sometimes also referred to as ''Brassica alba'' or ''B. hirta''. It probably originated in the Mediterranean region, but is now widespread worldwide. Grown for its seeds, it is used to make the condiment mustard, as a fodder crop, or as a green manure. Description White mustard is an annual, growing to high with stalkless pinnate leaves, similar to '' Sinapis arvensis''. The yellow flowers of ''S.'alba'' contain 4 petals per flower and 4 alternating sepals. In addition, their pods are approximately 2.0–4.2 cm long. Reproduction ''Sinapis alba'' is a long day plant, which means they flower when the amount of light received exceeds their critical photoperiod. Pollen from ''S. alba'' is able to be dispersed through wind and insect pollinators, such as wild bees, bumblebees, and flower flies. Additionally, white mustard is an obligate outcrossing species, ...
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Thiocyanate
Thiocyanates are salts containing the thiocyanate anion (also known as rhodanide or rhodanate). is the conjugate base of thiocyanic acid. Common salts include the colourless salts potassium thiocyanate and sodium thiocyanate. Mercury(II) thiocyanate was formerly used in pyrotechnics. Thiocyanate is analogous to the cyanate ion, , wherein oxygen is replaced by sulfur. is one of the pseudohalides, due to the similarity of its reactions to that of halide ions. Thiocyanate used to be known as rhodanide (from a Greek word for rose) because of the red colour of its complexes with iron. Thiocyanate is produced by the reaction of elemental sulfur or thiosulfate with cyanide: : : The second reaction is catalyzed by thiosulfate sulfurtransferase, a hepatic mitochondrial enzyme, and by other sulfur transferases, which together are responsible for around 80% of cyanide metabolism in the body. Oxidation of thiocyanate inevitably produces hydrogen sulfate. The other product depe ...
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Isothiocyanate
In organic chemistry, isothiocyanate is a functional group as found in compounds with the formula . Isothiocyanates are the more common isomers of thiocyanates, which have the formula . Occurrence Many isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates. A prominent natural isothiocyanate is allyl isothiocyanate, also known as mustard oils. Cruciferous vegetables, such as bok choy, broccoli, cabbage, cauliflower, kale, and others, are rich sources of glucosinolate precursors of isothiocyanates. Structure The and distances are 117 and 158 pm. By contrast, in methyl thiocyanate, and distances are 116 and 176 pm. Typical bond angles for in aryl isothiocyanates are near 165°. Again, the thiocyanate isomers are quite different with angle near 100°. In both isomers the angle approaches 180°. Synthesis Allyl thiocyanate isomerizes to the isothiocyanate: : Isothiocyanates can be prepared by treating organ ...
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Nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or propanenitrile). The prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons. Inorganic compounds containing the group are not called nitriles, but cyanides instead. Though both nitriles and cyanides can be derived from cyanide salts, most nitriles are not nearly as toxic. Structure and basic properties The N−C−C geom ...
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Cofactor (biochemistry)
A cofactor is a non-protein chemical compound or metallic ion that is required for an enzyme's role as a catalyst (a catalyst is a substance that increases the rate of a chemical reaction). Cofactors can be considered "helper molecules" that assist in biochemical transformations. The rates at which these happen are characterized in an area of study called enzyme kinetics. Cofactors typically differ from ligands in that they often derive their function by remaining bound. Cofactors can be classified into two types: inorganic ions and complex organic molecules called coenzymes. Coenzymes are mostly derived from vitamins and other organic essential nutrients in small amounts. (Some scientists limit the use of the term "cofactor" for inorganic substances; both types are included here.) Coenzymes are further divided into two types. The first is called a " prosthetic group", which consists of a coenzyme that is tightly (or even covalently and, therefore, permanently) bound to a ...
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Aglycone
An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ... molecule. Detection A way to identify aglycone is proposed to extract it from Agave spp. by using H-NMR and Heteronuclear multiple bond correlation (HMBC) experiments. The HMBC experiment can be combined with other techniques such as mass spectrometry to further examine the structure and the function of aglycone. Samples of glycones and glycosides from limonoids can be simultaneously quantified through a high performance liquid chromatography (HPLC) method, where a binary solvent system and a diode array detector separate ...
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D-glucose
Glucose is a sugar with the molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight. It is used by plants to make cellulose, the most abundant carbohydrate in the world, for use in cell walls, and by all living organisms to make adenosine triphosphate (ATP), which is used by the cell as energy. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as amylose and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form is -glucose, while its stereoisomer L-glucose, -glucose is produced synthetically in comparatively small amounts and is less biologically active. Glucose is a monosaccharide containing six carbon ato ...
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Sugar
Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ..., fructose, and galactose. Compound sugars, also called disaccharides or double sugars, are molecules made of two bonded monosaccharides; common examples are sucrose (glucose + fructose), lactose (glucose + galactose), and maltose (two molecules of glucose). White sugar is almost pure sucrose. In the body, compound sugars are hydrolysed into simple sugars. Longer chains of monosaccharides (>2) are not regarded as sugars and are called oligosaccharides or polysaccharides. Starch is a glucose polymer found in plants, the most abundant source of energy in human foo ...
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Lossen Rearrangement
The Lossen rearrangement is the conversion of a hydroxamic acid, hydroxamate ester to an isocyanate. Typically O-acyl, sulfonyl, or phosphoryl O-derivative are employed. The isocyanate can be used further to generate ureas in the presence of amines or generate amines in the presence of H2O. Reaction mechanism The mechanism below begins with an O-acylated hydroxamic acid derivative that is treated with base to form an isocyanate that generates an amine and carbon dioxide, CO2 gas in the presence of H2O. The hydroxamic acid derivative is first converted to its conjugate base by abstraction of a hydrogen by a base. Spontaneous rearrangement releases a carboxylate anion to produce the isocyanate intermediate. The isocyanate is then hydrolyzed in the presence of H2O. Finally, the respective amine and CO2 are generated by abstraction of a proton with a base and decarboxylation. Hydroxamic acids are commonly synthesized from their corresponding esters. Historical references * * * ...
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