Glucosinolate–myrosinase Complex
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Glucosinolate–myrosinase Complex
The mustard oil bomb, formerly known as the glucosinolate–myrosinase complex, is a chemical herbivory defense system found in members of the Brassicaceae (or cabbage family). The mustard oil bomb requires the activation of a common plant secondary metabolite, glucosinolate, by an enzyme, myrosinase. The defense complex is typical among plant defenses to herbivory in that the two molecules are stored in different compartments in the leaves of plants until the leaf is torn by an herbivore. The glucosinolate has a β-glucose and a sulfated oxime. The myrosinase removes the β-glucose to form mustard oils that are toxic to herbivores. The defense system was named a "bomb" by Matile, because it like a real bomb is waiting to detonate upon disturbance of the plant tissue. Countermeasures There are many examples of biochemical adaptations to the mustard oil bomb. One occurs in the diamondback moth, ''Plutella xylostella''. This worldwide crop pest feeds exclusively on members of the Bra ...
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Brassicaceae
Brassicaceae () or (the older) Cruciferae () is a medium-sized and economically important family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous plants, while some are shrubs. The leaves are simple (although are sometimes deeply incised), lack stipules, and appear alternately on stems or in rosettes. The inflorescences are terminal and lack bracts. The flowers have four free sepals, four free alternating petals, two shorter free stamens and four longer free stamens. The fruit has seeds in rows, divided by a thin wall (or septum). The family contains 372 genera and 4,060 accepted species. The largest genera are ''Draba'' (440 species), ''Erysimum'' (261 species), ''Lepidium'' (234 species), ''Cardamine'' (233 species), and ''Alyssum'' (207 species). The family contains the cruciferous vegetables, including species such as ''Brassica oleracea'' (cultivated as cabbage, kale, cauliflower, broccoli and collards), ...
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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. Plants with glucosinolates Glucosinolates occur as secondary metabolites of almost all plants of the order Brassicales. Ordered in the Brassicales are for example 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, horseradish, capers, and radishes wh ...
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Myrosinase
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 it ...
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Oxime
In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R’ may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides () with general structure . Oximes are usually generated by the reaction of hydroxylamine with aldehydes () or ketones (). The term ''oxime'' dates back to the 19th century, a combination of the words ''oxygen'' and ''imine''. Structure and properties If the two side-chains on the central carbon are different from each other—either an aldoxime, or a ketoxime with two different "R" groups—the oxime can often have two different geometric stereoisomeric forms according to the ''E''/''Z'' configuration. An older terminology of ''syn'' and ''anti'' was used to identify especially aldoximes according to whether the R group was closer or further from the hy ...
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Allyl Isothiocyanate
Allyl isothiocyanate (AITC) is an organosulfur compound (formula CH2CHCH2NCS). This colorless oil is responsible for the pungent taste of mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated through the TRPA1 and TRPV1 ion channels. It is slightly soluble in water, but more soluble in most organic solvents. Biosynthesis and biological functions Allyl isothiocyanate can be obtained from the seeds of black mustard (''Brassica nigra'') or brown Indian mustard (''Brassica juncea''). When these mustard seeds are broken, the enzyme myrosinase is released and acts on a glucosinolate known as sinigrin to give allyl isothiocyanate. Allyl isothiocyanate serves the plant as a defense against herbivores; since it is harmful to the plant itself , it is stored in the harmless form of the glucosinolate, separate from the myrosinase enzyme. When an animal chews the plant, the allyl isothiocyanate is released, repelling the animal. Human appr ...
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Diamondback Moth
The diamondback moth (''Plutella xylostella''), sometimes called the cabbage moth, is a moth species of the family Plutellidae and genus '' Plutella''. The small, grayish-brown moth sometimes has a cream-colored band that forms a diamond along its back. The species may have originated in Europe, South Africa, or the Mediterranean region, but it has now spread worldwide. The moth has a short life cycle (14 days at 25 °C), is highly fecund, and is capable of migrating long distances. Diamondback moths are considered pests as they feed on the leaves of cruciferous crops and plants that produce glucosinolates. However, not all of these plants are equally useful as hosts to the moth. Because of this, studies have suggested using wintercress as a trap crop around agricultural fields because diamondback moths are highly attracted to that plant but their larvae fail to survive when eggs are laid on it. Originally, pesticides were used to kill the moths but diamondbacks have de ...
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Sulfatase
Sulfatases are enzymes of the esterase class that catalyze the hydrolysis of sulfate esters. These may be found on a range of substrates, including steroids, carbohydrates and proteins. Sulfate esters may be formed from various alcohols and amines. In the latter case the resultant N-sulfates can also be termed sulfamates. Sulfatases play important roles in the cycling of sulfur in the environment, in the degradation of sulfated glycosaminoglycans and glycolipids in the lysosome, and in remodelling sulfated glycosaminoglycans in the extracellular space. Together with sulfotransferases, sulfatases form the major catalytic machinery for the synthesis and breakage of sulfate esters. Occurrence and importance Sulfatases are found in lower and higher organisms. In higher organisms they are found in intracellular and extracellular spaces. Steroid sulfatase is distributed in a wide range of tissues throughout the body, enabling sulfated steroids synthesized in the adrenals and gonads ...
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Sulforaphane
Sulforaphane (sometimes sulphoraphane in British English) is a compound within the isothiocyanate group of organosulfur compounds. It is produced when the enzyme myrosinase transforms glucoraphanin, a glucosinolate, into sulforaphane upon damage to the plant (such as from chewing or chopping during food preparation), which allows the two compounds to mix and react. Sulforaphane is present in cruciferous vegetables, such as broccoli, Brussels sprouts, and cabbage. Occurrence and isolation Sulforaphane occurs in broccoli sprouts, which, among cruciferous vegetables, have the highest concentration of glucoraphanin, the precursor to sulforaphane. It is also found in cabbage, cauliflower, Brussels sprouts, bok choy, kale, collards, mustard greens, and watercress. Research Although there has been some basic research on how sulforaphane might have effects ''in vivo'', there is no clinical evidence that consuming cruciferous vegetables and sulforaphane affects the risk of cancer or ...
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Glucosinolates
Glucosinolates are natural components of many pungency, pungent plants such as mustard plant, 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 Plant disease resistance, diseases, and impart a characteristic bitter (taste), bitter flavor property to cruciferous vegetables. Plants with glucosinolates Glucosinolates occur as secondary metabolites of almost all plants of the order (biology), order Brassicales. Ordered in the Brassicales are for example the economically important family Brassicaceae as well as Capparaceae and Caricaceae. Outside of the Brassicales, the genus, 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, Chines ...
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