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Glycosides Pharmacognosy Dr GLYCOSIDES PHARMACOGNOSY DR. KIBOI Glycosides Glycosides • Glycosides consist of a sugar residue covalently bound to a different structure called the aglycone • The sugar residue is in its cyclic form and the point of attachment is the hydroxyl group of the hemiacetal function. The sugar moiety can be joined to the aglycone in various ways: 1.Oxygen (O-glycoside) 2.Sulphur (S-glycoside) 3.Nitrogen (N-glycoside) 4.Carbon ( Cglycoside) • α-Glycosides and β-glycosides are distinguished by the configuration of the hemiacetal hydroxyl group. • The majority of naturally-occurring glycosides are β-glycosides. • O-Glycosides can easily be cleaved into sugar and aglycone by hydrolysis with acids or enzymes. • Almost all plants that contain glycosides also contain enzymes that bring about their hydrolysis (glycosidases ). • Glycosides are usually soluble in water and in polar organic solvents, whereas aglycones are normally insoluble or only slightly soluble in water. • It is often very difficult to isolate intact glycosides because of their polar character. • Many important drugs are glycosides and their pharmacological effects are largely determined by the structure of the aglycone. • The term 'glycoside' is a very general one which embraces all the many and varied combinations of sugars and aglycones. • More precise terms are available to describe particular classes. Some of these terms refer to: 1.the sugar part of the molecule (e.g. glucoside ). 2.the aglycone (e.g. anthraquinone). 3.the physical or pharmacological property (e.g. saponin “soap-like ”, cardiac “having an action on the heart ”). • Modern system of naming glycosides uses the termination '-oside' (e.g. sennoside). • Although glycosides form a natural group in that they all contain a sugar unit, the aglycones are of such varied nature and complexity that glycosides vary very much in their physical and chemical properties and in their pharmacological action. Types of Glycosides • Anthracene glycosides • Saponin glycosides • Coumarin glycosides • Flavonoid glycosides • Cyanogenetic glycosides (Cyanide glycosides) 1. Anthracene glycosides Anthracene • A number of glycosides in which the aglycones are anthracene derivatives occur as the pharmacologically active constituents of several cathartics of plant origin; e.g. cascara, rhubarb, aloe and senna. • anthracene glycosides are sometimes referred to as the anthraquinone glycosides or the anthraglycosides. • anthraquinone derivatives are glycosides, often glucosides or rhamnosides. • The presence of the sugar residue is a prerequisite for the pharmacological effects. • Anthraquinones are colored substances and many of them are used technically as dyes e.g. alizarin. • Reduced forms of anthraquinones, which exhibit keto-enol tautomerism, are often encountered. • The anthracene derivatives occur in vegetable drugs in different forms at different oxidation levels; like anthraquinones, anthrones, anthranols, or oxanthrones. Inter-relationship of anthraquinone derivatives OH Anthranol (enol form) Taut. O O 8 1 7 9 2 4 H ABC 6 10 3 5 4 Anthrone (keto form) O Anthraquinone − 2 H 2 H O O H OH Oxanthrone O Dianthrone • Anthracene compounds occur in these drugs or plant materials in some cases as the aglycones of O-glycosides (e.g. frangulin), and in other cases as the aglycones of C-glycosides (e.g. aloin). • Biosynthesis ; natural anthraquinones are synthesized either via the acetate-malonate pathway (like the medicinally important purgative anthraquinones), or they are derived from shikimate and mevalonate (like alizarin). OH O OH O OH OH HO CH3 O O Frangula emodin Alizarin A. Anthraquinones • Although anthraquinone is not used extensively in medical practice, it is the starting material for the preparation of several synthetic laxatives and represent the basic structure of a number of important laxatives and dyestuffs. • Borntrager ’s test is often used for their detection. • The derivatives of anthraquinone present in purgative drugs may be dihydroxy phenols such as chrysophanol, trihydroxy phenols such as emodin or tetrahydroxy phenols such as carminic acid. • Bontrager's test is a chemical test for the identification of anthraquinone glycosides. • boil test sample with 1ml of sulphuric acid in a test tube for 5min,filter while hot. • Cool the filtrate and shake with equal volume of dichloromethane or chloroform then separate the lower layer of chloroform and shake it with half volume of dilute ammonia. • A rose pink to red colour is produced in the ammonical layer. O O Anthraquinone OH O OH OH O OH CH3 HO CH3 O O Chrysophanol Emodin HO O OH O CH3 OH COOH HO OH HO OH OH O Carminic Acid B. Anthrones & Anthranols • These reduced anthraquinone derivatives occur either free or combined as glycosides. • They are isomeric and one may be partially converted to the other in solution. • Anthranols are converted upon oxidation into anthraquinones. Oxidation takes place in the crude drug during storage especially if powdered. • Schonteten’s test is often used for anthranols (green fluorescence). • Anthranols and anthrones are the main constituents of chrysarobin, a mixture of substances. OH OH OH OH O OH CH3 CH3 Chrysarobin (1,8-dihydroxy-3-methyl-9-anthrone; 3-methyl-1,8,9-anthracenetriol) C. Oxanthrones OH O OH H OH • These are intermediate products between anthraquinones and anthranols. • They give anthraquinones on oxidation with hydrogen peroxide. • An oxanthrone has been reported as a constituent of cascara bark. D. Dianthrones β-D-glucose–O O OH These are compounds derived from • COOH two anthrone molecules, which may COOH be identical or different. • They are important aglycones in β species of Cassia , Rheum and -D-glucose–O O OH Rhamnus . Sennosides • One of the best known is sennoside derived from two molecules of glucose and two molecules of rhein- anthrone. • On hydrolysis, sennoside yields the aglycone sennidin. E. Aloin-type or C-glycosides OH O OH • Aloin (Barbaloin) was obtained from species of Aloe . OH • It is strongly resistant to normal HO acid hydrolysis. O • In aloin, the sugar is joined to OH Aloin aglycone with a direct C-C linkage HO OH (a C-glycoside). • Two aloins (A and B) are known and arise from the chiral centre at C-10. 2. Saponin glycosides • A group of plant glycosides known as saponins share in varying degrees, two common characteristics: (a) They foam in aqueous solution. (b) They cause haemolysis of red blood cells. • The aglycones of the saponins are collectively referred to as Sapogenins . The more poisonous saponins are often called Sapotoxins . • Plant materials containing saponins have long been used in many parts of the world for their detergent properties for example, in Europe, the root of Saponaria officinalis (Fam. Caryophyllaceae ) and in South America, the bark of Quillaia saponaria (Fam. Rosaceae). Such plants contain a high percentage of the glycosides known as saponins (Latin Sapo, means Soap) which are characterized by their property of producing a frothing aqueous solution. Properties: • Saponins form colloidal solution in water (hydrophilic colloids) which froths upon shaking. These substances modify and lower the surface tension and therefore foam when shaken. This has led to their use to increase the foaming of beer. • Practical industrial applications of saponins include their use in cleaning industrial equipment and fine fabrics and as powerful emulsifiers of certain resins, fats and fixed oils. • In general, they have a bitter, acrid taste and drugs containing them are usually sternutatory (causing or producing sneezing ) and irritating to the mucous membranes of eyes and nose. • Characteristic for all saponins is their ability to cause haemolysis of red blood corpuscles and to destroy them. When injected into the blood stream, they are highly toxic. • When taken by mouth, Saponins are comparatively harmless, being not absorbed from the intestinal tract. Sarsaparilla , for example, is rich in saponins but is widely used in the preparation of nonalcoholic beverages. • Saponins are toxic especially to cold-blooded animals e.g. frogs. Many are used as fish-poisons. • The actual cause of the haemolysis : The red blood cells carry sterols in their membranes, and when brought into contact with saponins, the sterols of the RBCs are precipitated and the colloidal chemical properties of the membrane are so altered as to give hemoglobin passage to the surrounding medium. • Saponins have a high molecular weight and their isolation in a state of purity presents some difficulties. • Structure of Saponins: According to the structure of the aglycone or sapogenin, two kinds of saponin are recognized: 1.The steroidal type (commonly tetracyclic triterpenoids, C-27). 2.The triterpenoid type (pentacyclic triterpenoids, C-30). • Both of these have a glycosidal linkage at C-3 and have a common biosynthetic origin via mevalonic acid and isoprene units. 21 18 26 25 17 19 27 1 29 30 3 Steroid skeleton 25 26 28 1 3 27 Pentacyclic triterpenoid skeleton 23 24 A. Steroidal saponins • The steroidal saponins are less widely distributed in nature than the pentacyclic triterpenoid type. • Steroidal saponins are of great pharmaceutical importance because of their relationship to compounds such as the sex hormones, cortisone, diuretic steroids, vitamin D and the cardiac glycosides. • Examples: Diosgenin ( Dioscorea sylvatica), Sarsapogenin ( Smilax sp.). B. Pentacyclic triterpenoid saponins • Triterpenoid saponins my be classified into three groups represented by α-amyrin, β-amyrin and lupeol. • Examples:
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