Loganic Acid
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Loganic Acid
Loganic acid is an iridoid. Loganic acid is synthesized from 7-deoxyloganic acid by the enzyme 7-deoxyloganic acid hydroxylase (7-DLH). It is a substrate for the enzyme loganate O-methyltransferase for the production of loganin Loganin is one of the best-known of the iridoid glycosides. It is named for the Loganiaceae, having first been isolated from the seeds of a member of that plant family, namely those of ''Strychnos nux-vomica''. It also occurs in ''Alstonia boonei' ....Dewick (2009) Medicinal Natural Products: A Biosynthetic Approach. References Iridoid glycosides Glucosides Carboxylic acids Cyclopentanes {{organic-compound-stub ...
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Iridoid
Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose. The chemical structure is exemplified by iridomyrmecin, a defensive chemical produced by the ant genus ''Iridomyrmex'', for which iridoids are named. Structurally, they are bicyclic ''cis''-fused cyclopentane-pyrans. Cleavage of a bond in the cyclopentane ring gives rise to a subclass known as ''secoiridoids'', such as oleuropein and amarogentin. Occurrence The iridoids produced by plants act primarily as a defense against herbivores or against infection by microorganisms. The variable checkerspot butterfly also contains iridoids obtained through its diet which act as a defense against avian predators. To humans and other mammals, iridoids are often characterized by a deterrent bitter taste. Aucubin and catal ...
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7-Deoxyloganic Acid
7-Deoxyloganic acid is an iridoid monoterpene. 7-Deoxyloganic acid is produced from 7-deoxyloganetic acid by the enzyme 7-deoxyloganetic acid glucosyltransferase (7-DLGT).Salim, Yu, Altarejos and De Luca (2013) Virus-induced gene silencing identifies Catharanthus roseus 7-deoxyloganic acid-7-hydroxylase, a step in iridoid and monoterpene indole alkaloid biosynthesis. The Plant Journal. 76(5). 754-765 The metabolite is a substrate for the enzyme 7-deoxyloganic acid hydroxylase (7-DLH) which synthesizes loganic acid Loganic acid is an iridoid. Loganic acid is synthesized from 7-deoxyloganic acid by the enzyme 7-deoxyloganic acid hydroxylase (7-DLH). It is a substrate for the enzyme loganate O-methyltransferase for the production of loganin Loganin is one .... References Iridoid glycosides Carboxylic acids Glucosides Cyclopentanes {{organic-compound-stub ...
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Loganate O-methyltransferase
In enzymology, a loganate O-methyltransferase () is an enzyme that catalyzes the chemical reaction :S-adenosyl-L-methionine + loganic acid \rightleftharpoons S-adenosyl-L-homocysteine + loganin Thus, the two substrates of this enzyme are S-adenosyl methionine and loganic acid (also called loganate), whereas its two products are S-adenosylhomocysteine and loganin. This enzyme belongs to the family of transferases, specifically those transferring one-carbon group methyltransferases. The systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivial ... of this enzyme class is S-adenosyl-L-methionine:loganate 11-O-methyltransferase. Other names in common use include loganate methyltransferase, and S-adenosyl-L-methionine:loganic acid methyltransferase. This enzyme participates in ...
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Loganin
Loganin is one of the best-known of the iridoid glycosides. It is named for the Loganiaceae, having first been isolated from the seeds of a member of that plant family, namely those of ''Strychnos nux-vomica''. It also occurs in ''Alstonia boonei'' (Apocynaceae), a medicinal tree of West Africa and in the medicinal/entheogenic shrub Desfontainia spinosa (Columelliaceae) native to Central America and South America. Biosynthesis Loganin is formed from loganic acid by the enzyme loganic acid O-methyltransferase (LAMT). Loganin then becomes a substrate for the enzyme secologanin synthase (SLS) to form secologanin, a secoiridoid monoterpene found as part of ipecac and terpene indole alkaloid Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known diffe ...s. References {{reflist Iridoid glycosides ...
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Iridoid Glycosides
Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose. The chemical structure is exemplified by iridomyrmecin, a defensive chemical produced by the ant genus ''Iridomyrmex'', for which iridoids are named. Structurally, they are bicyclic ''cis''-fused cyclopentane-pyrans. Cleavage of a bond in the cyclopentane ring gives rise to a subclass known as ''secoiridoids'', such as oleuropein and amarogentin. Occurrence The iridoids produced by plants act primarily as a defense against herbivores or against infection by microorganisms. The variable checkerspot butterfly also contains iridoids obtained through its diet which act as a defense against avian predators. To humans and other mammals, iridoids are often characterized by a deterrent bitter taste. Aucubin and catal ...
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Glucosides
A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. The name was originally given to plant products of this nature, in which the other part of the molecule was, in the greater number of cases, an aromatic aldehydic or phenolic compound (exceptions are Jinigrin and Jalapin or Scammonin). It has now been extended to include synthetic ethers, such as those obtained by acting on alcoholic glucose solutions with hydrochloric acid, and also the polysaccharoses, e.g. cane sugar, which appear to be ethers also. Although glucose is the most common sugar present in glucosides, many are known which yield rhamnose or iso-dulcite; these may be termed pentosides. Much attention has been given to the non-sugar parts (aglyca) of the molecules; the constitutions of many have been determined, and the compounds synthes ...
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Carboxylic Acids
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion. Examples and nomenclature Carboxylic acids are commonly identified by their trivial names. They at oftentimes have the suffix ''-ic acid''. IUPAC-recommended names also exist; in this system, carboxylic acids have an ''-oic acid'' suffix. For example, butyric acid (C3H7CO2H) is butanoic acid by IUPAC guidelines. For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid. Alternately, it can be named as a "carboxy" or "carboxylic acid" substituent on another ...
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