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Definition: Organic natural compounds present in a lot of plants and some animals, these compounds upon hydrolysis give one or more sugars (glycone) _form and non sugar (aglycone) or called genin.
Solubility: glycosides are water soluble compounds and insoluble in the organic solvents. Glycone part: water soluble, insoluble in the organic solvents. Aglycone part: water insoluble, soluble in the organic solvents. Some glycosides soluble in alcohol.
Separation between glycosides parts: Glycosides Hydrolysis glycone +aglycone +HCL +HCLdil Neutralization by G + A +salt+H2O Filtration Using alkaline chloroform (H2O+G)+A (H2O+G)+(chloroform+A) We can separate them by using separatory funnel The best solvent to extract aglycone is Ethyl acetate because: A- immiscible in water. B- always presents in the upper layer.
Note: Alcohol and acetone are water miscible compounds,so we can't use them as organic solvents for aglycone separation.
Cont...
Odorless except saponin (glycyrrhizin). when a glycosides has a lot of sugars its solubility in water decrease. Glycosides hydrolyzed by using mineral acids and temperature or by using enzymes such as: a- Emolsin Bitter almond seeds. b- Myrosin or Myrosinase black mustard seeds. c- Rhamnase glycosides containing rhamnose as sugar part.
Cont
Some glycosides have antibacterial activity, so they protect the plants from bacteria and diseases.
bacteria kill Bitter almond
Amygdalin
Eomlsin enzyme
hydrolysis
HCN
Classification of glycosides
Cont
Laxative group of glycosides: a- Sennoside A,B,C,D (Senna leaves and fruits). b- Cascaroside A,B (Cascara bark). c- Frangulin and glucofrangulin(Frangula bark). d- Aloin and barbaloin (Aloe vera and Aloe barbadensis juice).
Cont
Local irritant group: a-Sinigrin(Black mustered seeds_Brassica nigra) b-Sinalbin(White mustered seeds_Brasica alba) Analgesics and antipyretics: Salicin hydrolysis Salisylic acid - Willow or Salix bark. Keeping elasticity of blood vessels like: Rutin_Rutoside (Bitter orange peels, Lemon peels) Anti-inflammatory group: a- Aloin for 1)acne 2)peptic ulcer b-Glycyrrhizin
O-glycosides : in these glycosides the sugar part is linked with alcoholic or phenolic hydroxyl or carboxyl group. S-glycosides : in these glycosides the sugar attached to a Sulfur atom of aglycone such as in sinigrin. N-glycosides : in these glycosides the sugar linked with Nitrogen atom of (-NH2,-NH-)amino group of aglycone like in nucleosides DNA,RNA C-glycosides : in these glycosides the sugar linked (condensed) directly to Carbon atom of aglycone like in aloin.
Classification of glycosides on the basis of the linkage between glycone and aglycone part
N.B C-glycosides are not hydrolyzed by acids or alkalis or by enzymes mainly . Classification of glycosides according to a glycone part : 1- if a glycone part alcohol -this group called alcoholic group like Salicin 2- if a glycone part aldehyde- this group called aldehydic gr. like glucovanillin. 3- if phenol called phenolic group like arbutin . 4-if cyanone called cyanogenic or cyanophoric or cyanoside like amygdalin. 5-if thio called glycosides or isothiocyanate glycoside like sinigrin or sinalbin (-S=C=N-) (SCN) 6-anthracene -------> anthraquinone glycoside sennoside-.
Most of glycoside may be named according to the plant from which they isolated for example:
1-salicin salix2-cascaroside _cascara 3-aloin- Aloe vera 4- sennoside senna5-frangulin frangula 6- glycyrrhizin glycyrrhiza And others.
Always glycosides founded in the plant with the enzymes which hydrolyzed them.
We must damage these enzymes first to extract these glycoside by the following steps: 1-drying the plants fresh in special oven at 100 c for 30 minutes.
Classification of glycosides according to a glycone part. 1- phenolic group of glycosides:Such as arbutin which isolated from bearberry leaves Uses: UTI as antiseptic and antibacterial & mild diuretic Drugs :
e. They form with hydrolysis glycone part which usually -D-glucose or its acids (glucuronic acid) + Sapogenin
f. Their aqueous solutions from froths (foam) on shakin and form emulsions on shaking and heating with oils and fats g. They destroy RBC (corpuscles) specially for fish and cold blooded animals m. Sapogenin (Triterpenoid) divided to : 1- steroidal Sapogenin 2- pent acyclic Sapogenin Examples:- licorice roots contain saponin glycoside which called Glycyrrhizin Glycyrrhizin hydrolysis glycyrrhetic acid + Z.M. glucyr acid
expectorant
anti-inflammatory
Ginseng roots
Panax roots
Panax quinquefolius ,panax ginseng -contains saponin glycoside ginsenoside ( panaxoside) Triterpenoid + steroidal nucleus Ginseng root uses : 1- stimulant 4-adaptogenic agent . Drugs : 2- Tonic 3- anti-stress
1- geriatric pharmaton
2- gerimax 3- polyvit
1. Group of glycosides which contains sulfur (Sglycoside) 2. Present in many cruciferous plants, on hydrolysis. 3. They produce isothiocynate (SCN) aglycone
Such as : 1.sinigrin which founded in Black Mustard seeds 2.sinalbin which founded Brassica alba --White Mustard seeds.
These plants contain also enzyme myrosin (myrosinase) which hydrolyze these glycosides. Properties of Mustard oil : 1.Irritant for mucous membrane 2.Volatile 3.Pungent 4.Characteristic odor
The uses of Mustard seeds : counter irritant rubefacient, condiment, emetic in large doses. Drug :Acne aid soap- Agis Treatment of Acne .
Sinapine : alkaloids alkaloidal amine group (protoalkaloid properties of Acrinyl isothiocynate. 1.Less irritant than allyl isothiocynate. 2.Less volatile. 3.Odorless. 4.Pungent. Uses of white mustard seeds Condiment, carminative, counter irritant, emetic
Cyanogenic glycosides
Group glycosides which widely distributed between the members of Rosaceae family. They gave with hydrolysis HCN (Hydrocyanic acid) They derived from nitrile of mandelic acid. Cyanosides like : 1. Amygdalin :
Flavonoids
Large group of glycosides which widely distributed in the plants kingdom and in all plants parts (leaves, roots, rhizomes, fruits peels) Various colors in flowers( yellow, orange, red, purple.) They are benzo-gama-pyrone derivatives. Their chemical structure based on (C6 C3 C6 ). The general uses of Flavonoids and Flavonoid glycosides. 1. Increase elasticity of blood vessels specially Rutin and hesperidin which known as vitamin (p) 2. Anti inflammatory activity like Taxifolin
3. 4.
Anti spasmodic activity like Thyme and sage flavonoids. Cytostatic activity.
Diosmetin Hesperitin
** C.G (Cardiac glycosides) : group of glycosides which has powerful action on cardiac muscles (cardiac muscle stimulant).
C.G glycone part consist of one , two, three monosaccharide units or more similar or different Aglycone part has steroidal nucleus
cyclopentanoperhudrophenanthrene
classification
1. cardenolide (one double bond, lactone ring) : Has five member lactone ring (unsaturated) attached at C17 B position of steroidal nucleus.
2. Bufadienolide: (contain two double bonds, lactone ring) Has six member ( unsaturated ) lactone ring attached at C-17 alpha position
1) The presence of hydroxyl group in C14 position makes the glycoside very active and gives rapid action in the body, but if we change it to (H+) group the drug will be inactive or less active. 2) The presence of Alpha & Beta unsaturated lactone ring increases the activity of C.G, but if we make it saturated the C.G will lose its activity. 3) The ring junctions Cis, Trans, Cis make the nucleus very stable so more active. 4) The sugar part increases absorption and distribution of C.G in the body S.P : Glucose, Rhamnose, Cymarose, Digitoxose
Examples of Cardenolides
1) Digitalis glycosides Digoxin Digitoxin Gitoxin
Bufadienolide example
Squill bulb glycoside Scillaren
** Chemical tests :1) Keller Kiliani test : C.G + CH3COOH + H2SO4 + FeCl3 2) Legal test : C.G + pyridine sodium nitroprusside brown Red to pink colour
*Uses :
1-CHF
Tannins
Widely distributed in the nature (leaves, barks, immature fruits but, they disappear during ripening process). They protect the plants from herbivorous animals, insects, bacteria and others specially during growth, like in new leaves which contain high percentage of tannins.
Some of them have low molecular weight but, most of them have very large molecular weight.
Physico_chemical properties
1. They form colloidal solutions with water.
2. Pseudo tannins.
Classification of tannins: 1)True tannins: (a)Hydrolysable group: 1- Hydrolyzed by acids or enzymes (Tannase). 2- They are esters of a sugar (-D-glucose) with one or more trihydroxybenzene carboxylic acid. 3-The tannins which derived from Gallic acid called Gallo-tannin or glucogallin like in Rhubarb rhizomes, Clove buds, Bearbers leaves.
4- tannis which derived from ellagic acid called ellagotannin or glucoellagin like in Pomegranate roots bark and Eucalyptus leaves (which also contain Tannic acid which is Gallotannin). 5- They form (H.T) with FeCl dark blue color. (b) Non hydrolysable group of tannin, condensed tannins or called proanthocyanidin tannins:
3- they are founded: In barks like: Cinnamon (Phlobatannins), Cinchona (Cinchotannin), Wild cherry. In seeds: Cacao, Cola (Colacatechin). In leaves: Tea. 4- they produce dark green color with FeCl. 5- they produce Catechol with HCl(conc.) and with vannillin_HCl reagent.
2) Pseudo tannins: 1- they have low molecular weight. 2- they occur: as Gallic acid like in Rhubarb rhizomes. as catechin like in Cacao, Acacia. as chlorogenic acid like in coffee.
The general uses of tannins: 1)Anti diarrhea . 2) Anti bacterial . 3) Antidote in case of poisoning from alkaloids and heavy metals . 4) Haemostatic .
5) Mild diuretic .
6) Leather industry . 7) Astringent for inflammated mucous membrane 8) Stomachic .
Chemical tests: 1) With FeCl : (a) H.T dark blue (b) Non H.T dark green 2) ppt. with alkaloids, gelatin, proteins, and salts of heavy metals like lead acetate, copper acetate. 3) With H2SO4 yellow 4) Vanillin_HCl reagent red to pink color.