Aglycone

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An aglycone (aglycon [1] or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. [2]

Glycosyl functional group formed by removing the hemiacetal hydroxy group from a monosaccharide, oligosaccharide or derivatives of these compounds

A glycosyl group is a univalent free radical or substituent structure obtained by removing the hemiacetal hydroxyl group from the cyclic form of a monosaccharide and, by extension, of a lower oligosaccharide. Glycosyl also reacts with inorganic acids, such as phosphoric acid, forming an ester such as glucose 1-phosphate.

Glycoside molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

For example, the aglycone of a cardiac glycoside would be a steroid molecule.

Cardiac glycosides are a class of organic compounds that increase the output force of the heart and increase its rate of contractions by acting on the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.

Steroid any organic compound having sterane as a core structure

A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes which alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene.

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In chemistry, a glycosidic bond or glycosidic linkage is a type of covalent bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate.

Saponin class of chemical compounds

Saponins are a class of chemical compounds found in particular abundance in various plant species. More specifically, they are amphipathic glycosides grouped phenomenologically by the soap-like foam they produce when shaken in aqueous solutions, and structurally by having one or more hydrophilic glycoside moieties combined with a lipophilic triterpene or steroid derivative.

Genin may refer to:

Picrocrocin chemical compound

Picrocrocin is a monoterpene glycoside precursor of safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste, and is the chemical most responsible for the taste of saffron.

Euxanthic acid chemical compound

Euxanthic acid is a xanthonoid glycoside, a conjugate of the aglycone euxanthone with glucuronic acid. Its magnesium salt is the primary colourant of the pigment Indian Yellow.

Hesperetin chemical compound

Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges. Hesperetin are not found to a significant extent in Citrus spp.

Genipin chemical compound

Genipin is a chemical compound found in gardenia fruit extract. It is an aglycone derived from an iridoid glycoside called geniposide present in fruit of Gardenia jasminoides.

Proscillaridin chemical compound

Proscillaridin is a cardiac glycoside, a kind of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia. It is of the bufanolide type and can be obtained from plants of the genus Scilla and in Drimia maritima.

Daigremontianin chemical compound

Daigremontianin is a bufadienolide. Bufadienolides are steroids and cardiac glycoside aglycones that are similar to cardenolides, differing only in the structure of the C-17 substituent on the D ring. This chemical has been found to be toxic in experiments on mice. It is one of five bufadienolides that have been isolated from Kalanchoe daigremontiana.

Cardenolide chemical compound

Cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides. Cardenolide glycosides are often toxic; specifically, they are heart-arresting.

Gymnemic acids are a class of chemical compounds isolated from the leaves of Gymnema sylvestre (Asclepiadaceae). They are anti-sweet compounds, or sweetness inhibitors. After chewing the leaves, solutions sweetened with sugar taste like water.

Apigetrin chemical compound

Apigetrin is a chemical compound that can be found in dandelion coffee and in Teucrium gnaphalodes.

Diosmetin chemical compound

Diosmetin, also known as 5,7,3'-trihydroxy-4'-methoxyflavone, is an O-methylated flavone, a chemical compound that can be found in the Caucasian vetch.

A xyloside is a type of glycoside derived from the sugar xylose.

GBA3 protein-coding gene in the species Homo sapiens

Cytosolic beta-glucosidase, also known as cytosolic beta-glucosidase-like protein 1, is a beta-glucosidase enzyme that in humans is encoded by the GBA3 gene.

Cirsilineol chemical compound

Cirsilineol is a bioactive flavone isolated from Artemisia and from Teucrium gnaphalodes.

Veronicastroside chemical compound

Veronicastroside is a flavone, a type of flavonoid. It is the 7-O-neohesperidoside of luteolin. It can be found in Veronicastrum sibiricum var. japonicum and in Teucrium gnaphalodes.

<i>Teucrium gnaphalodes</i> species of plant

Teucrium gnaphalodes is a plant species in the genus Teucrium. It is endemic to the Iberian Peninsula and grows at altitudes between 200 and 1500 m. It flowers from March to July.

Vaginol

Vaginol is a chemical compound. Its glucoside is apterin.

References

  1. "2-Carb-33". www.chem.qmul.ac.uk. Archived from the original on 12 November 2016. Retrieved 21 April 2018.
  2. IUPAC Compendium of Chemical Terminology 2nd Edition (1997) 1995, 67, 1312