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Glycosides May Be Defined as the Organic Compounds From Plants

Glycosides May Be Defined as the Organic Compounds From Plants

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glycosides
glycosides

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07/07/2013

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GLYCOSIDES
Glycosides may be defined as the organic compounds from plants or animal sources,which on enzymatic or acid hydrolysis give one or more sugar moieties along with non-sugar moiety. Glycosides play numerous important roles in living organisms. Many plants store important chemicals in the form of inactive glycosides; if these chemicals areneeded, the glycosides are brought in contact with water and anenzyme, and the sugar  part is broken off, making the chemical available for use. Many such plant glycosides areused asmedications. In animals (including humans), poisons are often bound to sugar molecules in order to remove them from the body.Formally, a glycoside is any molecule in which a sugar group is bonded through itscarbonatom to another group via anO-glycosidic bondor anS-glycosidic bond; glycosides involving the latter are also called
thioglycosides
. The sugar group is thenknown as the
glycone
and the non-sugar group as the
aglycone
or 
genin
part of theglycoside. The glycone can consist of a single sugar group (monosaccharide) or severalsugar groups (oligosaccharide).
ClassificationClassification based on linkages
Based on the linkage of sugar moiety to aglycone part1.O-Glycoside:-Here the sugar is combined with alcoholic or phenolic hydroxylfunction of aglycone.eg:-digitalis.2.N-glycosides:-Here nitrogen of amino group is condensed with a sugar ,eg- Nucleoside3.S-glycoside:-Here sugar is combined with sulphur of aglycone,eg- isothiocyanateglycosides.4.C-glycosides:-By condensation of a sugar with a cabon atom, eg-Cascaroside,aloin.Glycosides can be classified by the glycone, by the type of glycosidic bond, and by theaglycone.
By glycone
If the glycone group of a glycoside isglucose, then the molecule is aglucoside;if it is fructose, then the molecule is afructoside; if it isglucuronic acid, then the molecule is a glucuronide; etc. In the body, toxic substances are often bonded to glucuronic acid toincrease their water solubility; the resulting glucuronides are then excreted.
By type of glycosidic bond
 
Depending on whether the glycosidic bond lies "above" or "below" the plane of the cyclicsugar molecule, glycosides are classified as
α-glycosides
or 
β-glycosides
. Someenzymes such asα-amylasecan only hydrolize α-linkages; others, such asemulsin, can only affect β-linkages.
By aglycone
Glycosides are also classified according to the chemical nature of the aglycone. For  purposes of biochemistry and pharmacology, this is the most useful classification.
Alcoholic glycosides
An example of analcoholicglycoside issalicinwhich is found in the genus
.Salicinis converted in the body intosalicylic acid, which is closely related toaspirinand has analgesic,antipyreticandantiinflammatoryeffects.
Anthraquinone glycosides
These glycosides contain an aglycone group that is a derivative of anthraquinone.Theyare present insenna,rhubarbandaloes; they have alaxativeeffect.
Coumarin glycosides
Here the aglycone iscoumarin. An example isapterinwhich is reported to dilate the coronary arteriesas well as block calcium channels.those obtained from dried leaves of  Psoralia corylifoliahave main glycosides psoralin and corylifolin.
Cyanogenic glycosides
In this case, the aglycone contains acyanidegroup, and the glycoside can release the poisonoushydrogen cyanideif acted upon by some enzyme. An example of these isamygdalinfromalmonds.Cyanogenic glycosides can be found in the fruits (and wilting leaves) of therose family(including cherries, apples, plums, almonds, peaches, apricots,raspberries, and crabapples).Cassava, an important food plant in Africa and SouthAmerica, contains cyanogenic glycosides and therefore has to be washed and groundunder running water prior to consumption.Sorghum(
Sorghum bicolor 
) expressescyanogenic glycosides in its roots and thus is resistant to pests such as rootworms(Diabroticaspp.) that plague its cousinmaize(
 Zea mays
L.).
Flavonoid glycosides
Here the aglycone is aflavonoid. This is a large group of flavonoid glycosides. Examplesinclude:
Hesperidin(aglycone:Hesperetin,glycone:Rutinose)
 Naringin(aglycone: Naringenin,glycone:Rutinose)
 
Rutin(aglycone:Quercetin, glycone:Rutinose)
Quercitrin(aglycone:Quercetin,glycone:Rhamnose) Among the important effects of flavonoids are their antioxidanteffect. They are alsoknown to decreasecapillaryfragility.
Phenolic glycosides (simple)
Here the aglycone is a simple phenolicstructure. An example isarbutinfound in the Common Bearberry 
 Arctostaphylos uva-ursi
. It has a urinary antiseptic effect. Rutinfound in rooibos tea.
Saponin glycosides
These compounds give a permanent froth when shaken with water. They also causehemolysisof red blood cells.Saponin glycosides are found inliquorice.Their medicinal value is due to their expectoranteffect.
Steroidal glycosides orcardiac glycosides
Here the aglycone part is asteroidalnucleus. These glycosides are found in the plantgenera
, 
, and
. They are used in the treatment of heart diseasese.g.congestive heart failureandarrhythmia.
Steviol glycosides
These sweet glycosides found in thestevia plant
Stevia rebaudiana bertoni
have 40-300times the sweetness of sucrose. The two primary glycosides, stevioside and rebaudiosideA, are used as naturalsweetenersin many countries. These glycosides havesteviolas the aglycone part.Glucoseor rhamnose-glucose combinations are bound to the ends of the aglycone to form the different compounds.
Isothiocyanate glycosides
As the name implies, these compounds containsulfur . Examples includesinigrin, found in black mustard, andsinalbin, found inwhite mustard.
1
. Steroidal glycosides orcardiac glycosides
Many of the plants known to contain cardiac or cardiotonic glycosides have long beenused as arrow poisons (e.g.
Strophanthus
) or as heart drugs (e.g.
 Digitalis
). They are usedto strengthen a weakened heart and allow it to function more efficiently, though thedosage must be controlled very carefully since the therapeutic dose is so close to the toxicdose. In plants, cardiac glycosides are confined to the Angiosperms, but are found in bothmonocotyledons and dicotyledons.

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