Journal of Medicinal Plants Research Vol. 6(6), pp. 934-937, 16 February, 2012 Available online at http://www.academicjournals.org/JMPR DOI: 10.5897/JMPR11.

732 ISSN 1996-0875 2012 Academic Journals

Review

Glycosides: A potential source of phytomedicine

M. Akram1*, E. Muhiuddin2, A. Ahmed3, Shahab-uddin1, K. UsmanGhani4, H. M. Asif5 and S. M. Ali Shah5
Department of Basic Medical Sciences, Faculty of Eastern Medicine, Hamdard University Karachi, Pakistan. Department of Surgery and Allied Sciences, Faculty of Eastern Medicine, Hamdard University Karachi, Pakistan. 3 Department of Medicine and Allied Sciences, Faculty of Eastern Medicine, Hamdard University Karachi, Pakistan. 4 Department of Pre-Clinical Sciences, Faculty of Eastern Medicine, Hamdard University Karachi, Pakistan. 5 College of Conventional Medicine, the Islamia University of Bahawalpur, Pakistan.
2 1

Accepted 14 December, 2011

Glycosides are a group of naturally occurring substances in which carbohydrate residue combines with non-sugar entity (aglycon). Various glycosides occur in plants. Cardiac glycosides (CG) are used as heart stimulating medicine including digitalis and strophanthus. Many antibiotics are glycosides in nature including streptomycin. In this review article, introduction, classification and research study of glycosides has been discussed. Key words: Glycoside, classification of glycosides, cardiac glycosides, research study.

INTRODUCTION Glycosides are compounds which upon hydrolysis give rise to one or more sugars (glycones) and a non-sugar compound (aglycone or agnen). In a glycosidic compound a sugar residue is linked to C-l through oxygen O-gluoside) nitrogen (n-glucoside) or sulphur (sglucoside) moiety. B-d-glucose is the most common sugar found in glycosides. The other sugars decected are rhamnose, digitoxose and cymarose (deoxysugar). The glycosides from individual sugars are called glucoside, rhamnoside, galactside fructoside, etc. in glycosides the hydroxyl of a sugar is condensed with the hydroxyl of the non-sugar component. The secondary hydroxyl within the sugar molecule is condensed to form anoxide ring. Thus, they may be considered as acettals or sugar ethers. By acid or base catalyzed or enzymic hydrolysis glycosides yield the parent sugar together with the non-sugar compound. The sugar component is known as the glycone; while the non sugar residue is called aglycone. The aglycone may be an alcohol, phenol, cyanohydrins or complex fused ring or heterocyclic hydroxy compounds. More than one molecule of sugars may be present in aglycosides which are formed by either separate linkages or stepwise substitution of the sugars to the aglycone. In plants only b-forms of glycosides are formed. Most of the glycosides are colorless, crystalline compounds. Anthracene glycosides are red, orange colored compounds and flavone glycosides are yellowish in color. They are soluble in water and alcohol, but solvents like petroleum ether, solvent ether chloroform, carbon tetrachloride, etc. glycosides are optically laevorotatory. Many glycosides have antitumor activity, Cham et al. (1987) studied that glycoalkaloid isolated from Solanum sodomaeum has antitumor activity. Guimaraes et al. (2000) demonstrated that Eggplant (Solanum melongena) infusion has a modest and transitory effect on hypercholesterolemic subjects. Fu et al. (2005) demonstrated that total flavones of Hippophae rhamnoides promote early restoration of ultimate stress of healing patellar tendon in a rat model. Jagetia and Rajanikant (2205) studied that curcumin treatment enhances the repair and regeneration of wounds in mice exposed to hemibody gamma irradiation.

CLASSIFICATION
*Corresponding author. E-mail: makram_0451@yahoo.com. Tel: 920216440083. Fax: 920216440079.

Various types of classification of glycosides have been

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mentioned. On the basis of linkage of sugar molecule to aglycone, they are divided as follows:

example, amygdalin and prunasin.

Triterpenic glycosides O-glycosides In these glycosides the sugar is combined with alcoholic or phenolic hydroxyl function of aglycone: for example, digitoxin. N- glycosides Alcohol glycosides: for example, salicin. In these glycosides nitrogen of amino group (-nh2/-nh-) is condensed with a sugar for example, nucleoside. Lactone glycosides S-glycoside These glycosides contain a sugar moiety attached to sulphur of the aglycone, e.., isthiocyanate glycosides. Lsothiocyanate glucosides C- glycosides Condensation of a sugar directly to a carbon atom gives rise to c-glycosides, for example, aloin and cascaroside. These glycosides are not hydrolyzed with acids, alkalis or enzymes, on the basis of the chemical nature of aglycone the glycosides are classified as follows: Lsothiocyanate glucosides: for example, sinigrin and sinalbin. Lactone glycosides: glycosides. for example, hydroxycoumarin Triterpenic glycosides: a triterpene molecule is condensed with a sugar component for example, glycyrrhizin.

Alcohol glycosides

Saponin glycosides Saponin glycosides: for example, diosin.

Steroidal glycosides Steroidal glycosides: these glycosides contain a sterol as an aglycone, for example, diosgenin.

RESEARCH STUDY OF GLYCOSIDES Flavones C-glycosides from Montana bipinnatifida stems and evaluation of hepatoprotective activity of extract M. bipinnatifida has been evaluated for its phenolic compounds and hepactoprotective activity. A new flavon C-glycosides named as luteolin 6-C- apioside 8-Cglucoside (1) as well as apigenin 6-C-glucoside(2), apigenin 8-C-glucoside(3), apigenin 6,8di-Cglucoside(4), luteolin 8-C-glucoside(5) luteolin 6,8- di-Cglucoside(6), luteolin 6-C- glucoside(7), apigenin(8) and luteolin(9) were isolated from the M. bipinnatifida stems aqueous alcoholic extract (Toumy and Enayat, 2011). Phytochemical constituents vis-a-vis histochemical localization of forskolin in a medicinal plant Coleus forskohlii Briq A study was carried out to determine the tannins, phlobatannins, saponins, flavonoids, terpenoids, cardiac glycosides and alkaloids distribution in C. forskohlii. In this study, terpenoids, tannins, flavonoids, phlobatannins, saponins and CG were found in C. forskohlii (Selima, 2011).

Flavonoid glycosides Flavonoid glycosides: a flavonoid aglycone is present in these glycosides for example, rutin. The majority of flavonoids, such as anthocyanins, proanthocyanidins, and isoflavones, are stored in the central vacuole.

Anthracene glycosides Anthracene glycosides: in this glycone sugar moiety is attached to an anthracene aglycone for example, frangulin and barbaloin. Cyanophoric glycosides Cyanophoric glycosides: cyanogens are the aglycone part. They yield hydrocyanic acid on hydrolysis for

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Table 1. Cardiac glycosides are found in a diverse group of plants (Katz A et al, 2010).

Botanical name Digitalis purpurea and Digitalis lanata Nerium oleander Thevetia peruviana Convallaria majalis Urginea maritima and Urginea indica Strophanthus gratus Apocynum cannabinum Cheiranthus cheiri.

Common name Foxgloves common oleander yellow oleander lily of the valley Squill Ouabain Dogbane Wallflower

New acylated flavonol glycoside from Ceratonia siliqua L. seeds A study was carried out to find out new glycosides from C. siliqua L. seeds. New flavonol glycoside, 4`-phydroxybenzoylisorhamnetin-3-O-_-L-rhamnopyranoside named ceratoside (5), together with the known kaempferol-3-O-_-L-rhamnopyranoside (afzelin) (3), quercetin-3-O-a-Larabinofuranoside (auriculain) (4) quercetin-3-O-_-L-rhamnopyranoside (6), _-sitosterol (1) and _-sitosterol-3-O-b-D-glucoside (2) were found from C. siliqua L. seeds. These compounds were identified through ultraviolet (UV), infrared (IR), mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral data (Gohar et al., 2009). Phytochemical and antibacterial investigation of bark extracts of Acacia nilotica A. nilotica was evaluated for active principles and result indicated that stem bark extract of the plant contains terpenoids, tannins, alkaloids, saponins and glycosides (Banso, 2009). PHYTOMEDICINAL ACTIVITY OF GLYCOSIDES Devipriya and Shyamladevi (1999) studied that quercetin exert has protective effect in cisplatin induced cell injury in the kidney. Cham and Meares (1987) evaluated that glycoalkaloids from S. sodomaeum L. are effective in the treatment of skin cancers in man. CG exhibits their action on heart (Table 1). Cardiac glycosides (CG) are a diverse family of naturally derived compounds that bind to and inhibit Na+/K+-ATPase. The therapeutic efficacy of CG for heart failure is limited by the narrow therapeutic index and possible arrhythmogenic effects at high concen-trations. Glycosides possessing bitter taste are called bitter glycosides for example, glycosides of gentianceae. Glycosides are used for the treatment of various illnesses. Digitalis and strophanhus contain CG and are used as cardiac stimulant drugs. Anthraquinone

glycosides, present in senna, cascara, rhubab and aloe are used as laxative. Picrorhiza roots and rhizomes possess picroside glycosides and are utilized as bitter tonic and to protect damaged liver. Wild cherry bark and scilla glycosides have expectorant properties. Dioscin is a saponin glycosides found in the tubers of dioscorea species and its hydrolysis furnishes diosgenin aglycone. Various steroidal drugs have been synthesized from diosgenin. Some glycosides are less effective in original from, but produce active compounds on hydrolysis for example sinigrin a glycoside of black mustard is nonirritating in its natural form but on hydrolysis a powerful irritating substance allylisothiocyanate, is formed. Badami et al. (2003) evaluated that leaves of Solanum pseudocapsicum has antitumor activity. Maquart et al. (1999) studied that triterpenes from Centella asiatica stimulate extracellular matrix accumulation in rat experimental.

CONCLUSION Glycosides contain carbohydrate and a noncarbohydrate component. Non carbohydrate components are called aglycon. The carbohydrate component is attached by an acetal linkage at carbon atom 1 to a noncarbohydrate component. The carbohydrate component is called the glycone. If the carbohydrate portion is glucose, the compound is called glucosides. There are various types of glycosides that have many functions in the body. Most important glycosides are CG that is prescribed for treatment of various cardiac ailments.
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sodomaeum L. are effective in the treatment of skin cancers in man. Cancer Lett., 36: 111-118. Devipriya S, Shyamladevi CS (1999). Protective effect of quercetin in cisplatin induced cell injury in the kidney. Indian J. Pharmacol., 13: 422. Fu SC, Hui CW, Li LC, Cheuk YC, Qin L, Gao J, Chan KM (2005). Total flavones of Hippophae rhamnoides promote early restoration of ultimate stress of healing patellar tendon in a rat model. Med. Eng. Phys., 27: 313-321. Gohar A, Gedara SR, Baraka HN (2009). New acylated flavonol glycoside from Ceratonia siliqua L. seeds. J.M.P.R., 3(5): 424-428. Guimaraes PR, Galvao AM, Batista CM, Azevedo GS, Oliveira RD, Lamounier RP, Freire N, Barros AM, Sakurai E, Oliveira JP, Vieira EC, Alvarez- Leite JI (2000). Eggplant (Solanum melongena) infusion has a modest and transitory effect on hypercholesterolemic subjects. Braz. J. Med. Biol. Res., 33(9): 1027-1036. Jagetia GC, Rajanikant GK (2005). Curcumin treatment enhances the repair and regeneration of wounds in mice exposed to Hemibody girradiation. Plast. Reconstr. Surg., 115: 515-528.

Katz A, Lifshitz Y, Bab-Dinitz E, Kapri-Pardes E, Goldshleger R, Tal DM, Karlish SJ (2010). Selectivity of digitalis glycosides for isoforms of human Na,K-ATPase. J. BioChem., 285(25): 19582-19592. Maquart FX, Chastang F, Simeon A, Birembaut P, Gillery P (1999).Triterpenes from Centella asiatica stimulate extracellular matrix accumulation in rat experimental wounds. Eur. J. Dermatol., 9: 289-296. Selima K, Uur , Narayan C (2011). Phytochemical constituents vis-avis histochemical localization of forskolin in a medicinal plant Coleus forskohlii Briq, J.M.P.R., 5(5): 711718. Toumy E, Enayat A (2011). Flavone C-glycosides from Montanoa bipinnatifida stems and evaluation of hepatoprotective activity of extract, J.M.P.R., 5(8): 1291-1296.