University of Santo Tomas Faculty of Pharmacy Department of Pharmacy

I.

Definition

Cyanogenic glycosides or cyanoglycosides account for approximately 90% of the wider group of plant toxins known as cyanogens but are also found in insects and fungi. The ability of plants to produce cyanide from a parent compound was first discovered by Schrader. The key characteristic of these toxins is cyanogenesis, the formation of free hydrogen cyanide (HCN), and is associated with cyanohydrins that have been stabilised by glycosylation (attachment of sugars) to form the cyanogenic glycosides. They consists of an -hydroxynitrile stabilised by a glycosidic linkage to a sugar moiety and are classified their precursor amino acids and their sugar moiety, which is usually glucose. Most cyanogenic glycosides are derived from 4 amino acids (phenylalanine, tyrosine, valine, or isoleucine) or from nicotinic acid. II. Medicinal use

One of the medicinal uses of cyanogenic glycoside is it is used as a sedative and expectorant to the respiratory tract. Examples of which are Wild Cherry Bark (prunus serotina),a classic prunasin conataining respiratory herb, for dry irritable coughs and Apricot kernel, a Chinese medicine, used for coughs and asthma. Cyanogenic glycoside is also known for its cooling effect. Samples are the hydrocyanic acid which cuts down heat at a cellular level, the peach, apple and pear which are all cooling fruits that contain Cyanogens. And lastly, cyanogenic glycoside has been found with anti-cancer properties. An example is the Amygdalin/Laetrile which has been researched as an anti-tumor remedy. III. Classification Definition Many biologically active compounds are glycosides. A glycoside is any compound containing a carbohydrate molecule (sugar), particularly any such natural product in plants, convertible, by hydrolytic cleavage, into a sugar and a non-sugar component. They are secondary formed products in which the non-sugar component is known as aglycone. The most common types of glycosides are saponins, cardiac glycosides (cardenolides), cyanogenic glycosides and anthraquinone glycosides.

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University of Santo Tomas Faculty of Pharmacy Department of Pharmacy

Chemical structure

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University of Santo Tomas Faculty of Pharmacy Department of Pharmacy

Medicinal use Cardiac drugs: cardiotonic glycosides e.g., digitalis glycosides, strophanthus, squill. Laxatives e.g., anthraquinone glycosides of senna, aloes, rhubarb, cascara, frangula. Counter irritants e.g., thioglycosides and their hydrolytic products allylisothiocyanate Analgesics e.g., methylsalicylate a hydrolytic product of gaultherin. Anti rheumatic e.g., salicin. Some glycosides are claimed to reduce the capillary fragility e.g., flavonoidal glycosides, rutin, hisperidin. Anti-inflamatory: e.g., the glycoside glycyrrhizin has a demulcent, expectorant and antispasmodic action. More recently as an anticancer agent e.g., amygdalin known in the U.S. as Laetrile.

IV.

Appropriate extraction procedure 1. Destruction of hydrolysing enzymes. a. Drying for 15-30 min. at 100 C. b. Place plant in boiling water or alcohol 10-20 min. c. Boiling with acetone. d. Cold acid pH treatment. e. Extract at very low temperature. 2. De-fating or purification of the plant material (in case of seeds). 3. Extraction of the glycosidal constituents by alcohol, water or dilute alcohols. Some times ether saturated with water for dry material. 4. Concentrate the alcoholic extract (to get rid of the organic solvent). Add water (or hot water) filter any precipitate. 5. Purify aqueous extract: i. Extract non glycosidal impurities by org solvent. ii. Water soluble impurities precipitate by lead acetate. 6. Precipitate excess lead salts. 7. Isolation of the glycosides from the purified aqueous solution, by crystallization.

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University of Santo Tomas Faculty of Pharmacy Department of Pharmacy

V.

References (books and journal) Vetter, Janos .Plant cyanogenic glycosides. Toxicon 38 March 1999

Beale, John and Block, John. Wilson and Gisvolds Textbook of Organic Medicinal and Pharmaceutical Chemistry 12th Ed. Baltimore and Philadelphia: Lippincott Williams & Wilkins, 2011. Vladimr Kren* and Ludmila Martnkov, Current Medicinal Chemistry, Glycosides in Medicine: "The Role of Glycosidic Residue in Biological Activity" 2001, 8, 1303-1328 Roslyn, Gleadow et. al. Detection, identification and quantitative measurement of cyanogenic glycosides.

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