Glycosides are a heterogeneous group of natural substances, widely spread in nature and united by a structure that has a sugary part, called glycone, and a non-sugary part, called genin or aglycone, linked together. Also known as heterosides and endowed with a remarkable pharmacological polyvalence, the complexed glycosides behave like real pro-drugs: once taken they undergo enzymatic hydrolysis processes that separate the sugar part from the "aglycone". generally, it represents the pharmacologically active fraction of the molecule; the sugar part, however, contributes to modulate the "intensity of" action, its toxicity and the solubility of the entire molecule; glycone, for example, is essential for the accumulation of essential oils (hydrophobic) in the aqueous compartment of the vacuoles .
Glycosides can be classified on the basis of:
1) to the sugary part (glucose, fructose, rhamnose, galactose or arabinose);
2) to the part that represents the aglycone (the various secondary metabolites);3) the type of bond that holds the aglycone to the non-sugar part;
4) the physical or pharmacological properties of the glycoside;
1) On the basis of the sugary part that characterizes them, for example, glycosides can be classified into glucosides (glycone = glucose), fructosides (glycone = fructose), rhamnosides (glicone = rhamnose), galactosides (glycone = galactose), arabinosides ( glycone = arabinose), steviosides (glycone = steviol) etc. If, on the other hand, the sugary part is composed of more sugars, these must all be named; thus, for example, we will speak of rhamnoglucoside in reference to a generic glycoside containing a glycone composed of rhamnose and glucose.
2) To highlight the type of aglycone present in the glycosidic molecule, suffixes such as antachinon- (aglycone = anthraquinone), phenol- (aglycone = phenol), flavonol- (aglycone = flavonol), coumarin- (aglycone = coumarin) are used , sterol- (aglycone = sterol) etc. Other times it is preferred to use the relative attribute, for example anthraquinone glycoside (aglycone = anthraquinone) etc.
3) With reference to the type of bond that holds the aglycone to the non-sugar part, we speak of O-glycosides (sugar linked to the aglycone through an oxygen atom), S-glycosides (sugar linked to the aglycone through an atom of sulfur), C-glycosides (sugar linked to the aglycone through a carbon atom) and N-glycosides (sugar linked to the aglycone through a nitrogen atom).
Considering the extreme variability of the chemical-physical properties and pharmacological activities, the classification of glycosides is often entrusted to the nature of the functional part (aglyconic).
Examples of glycosides and in-depth articles
Deepening: Types of glycosides
ANTHRACHINONE GLYCOSIDES: glycosides containing aglycones structurally related to the anthracene molecule; this is the case of sennosides of senna, which have a powerful laxative effect.
CARDIOACTIVE GLYCOSIDES: glycosides with powerful and specific action on the heart; this is the case of digitoxin contained in digitalis (cardiotonic effect).
CYANOGENETIC GLYCOSIDES: glycosides which by hydrolysis release hydrogen cyanide, with extremely toxic effects but with potential anticancer activities; this is the case of the amygdalin contained in the bitter almond.
PHENOLIC GLYCOSIDES: the best known is the bearberry arbutin, used in phytotherapy against bacterial cystitis and urethritis for its antiseptic properties on the urinary tract.
FLAVONIC GLYCOSIDES: aglycone is a flavonoid; we recall, for example, rutin, characteristic of Rue, with a vasoprotective effect, whose aglycone is represented by the flavonoid quercetin.
SALICYL GLYCOSIDES: salicin extracted from willow bark or meadowsweet spirea is known for its analgesic, antirheumatic and antipyretic effects; it is no coincidence that it is the basis for the production of the famous Aspirin.
SAPONIN GLYCOSIDES: the glycyrizin of licorice has gastroprotective, anti-ulcer and hypertensive properties; the ginsenosides of ginseng have an adaptogenic effect.
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