Glycosides (Pharmacognosy) presenation.pptx

Glycosides in context of Pharmacognosy

1. Gly Glycosides co s Imran Waheed Assistant Professor Lahore Pharmacy College, (LMDC) Lecture stuff taken from different sources (books, research papers and dara bases. t Lecture stuff taken from different sources (books, research papers and dara bases. By Zunaira Nazish Lecture stuff taken from different sources (books, research papers and data bases).

2. Introduction A glycoside is an organic compound, usually of plant origin, that is composed of a sugar portion linked to a non-sugar moiety. Sugar portion ……….. Glycone Non-sugar portion…... Aglycone / Genin Linkage between sugar and non-sugar is usually an “oxygen linkage”

3. ROH+HOX ⇔ R O X+H 2 O ( Glycon ) ( Aglycon ) (Glycoside)

4. Properties Chemically glycosides are considered as sugar ether. In pure state glycosides mostly levorotatory, crystalline, colourless and bitter. They are soluble in alcohol and chloroform. Glycosides are hydrolysed by acid or alkali and by enzyme resulting in cleavage of glycosidic linkage.

5. Functions Glycosides play an important role in the life of plants involving regulatory and protective functions. The therapeutic efficiency of glycoside is due to aglycone. Glycone helps to carry the aglycone to site of organ or tissue where action is required.

6. Isolation of glycosides The dried plant material is rendered into a moderately coarse powder. The powder is then extracted in a Soxhlet apparatus with aqueous ethanol. The non- glycosidal impurities which get extracted along with glycosides are removed by precipitating them with lead acetate solution. The excess of lead acetate is then removed by passing hydrogen sulphide gas through the extract. Lead gets precipitated as lead sulphide , which is filtered out. The filtrate contains the glycosides. The glycoside can be obtained by removal of the solvent under reduced pressure or any other suitable procedure. Further purification of the isolated glycosides is done by column chromatography.

7. Extraction Generally in the extraction of the glycosides we need the following points: 1 . A solvent , which is mostly alcohol , but not water , since water may induce fermentation , in addition water needs high temperature due to its high boiling point. 2. Neutralization of the extract with base, since the presence of acid lead to hydrolysis of the glycoside. 3. Use of heat is to inhibit the activity of the hydrolytic enzymes that is present in the plant cell.

8. Classification of Glycosides There are 3 ways to classify the glycosides. On the basis of linkage between aglycon and glycone. On the basis of glycone part. On the basis of chemical nature of glycoside.

9. 1. On the basis of linkage between aglycon and glycone. O- glycosides (digitoxin, digoxin) C- glycosides (barbaloin) S- glycosides (black mustard) N- glycosides (adenosin)

10. 2. On the basis of glycone part Glucosides ( glucose) Ribosides (ribose) Rhamnosides ( Rhamnose)

11. 3. On the basis of chemical nature of glycoside. a) Cardioactive glycosides: Digitalis, Strophanthus and white squill (b) Anthraquinone glycosides: Cascara, Aloe, Rhubarb, Cochineal and Senna (c) Saponin glycosides: Glycyrrhiza, Ginseng, Sarsaparilla (d) Cyanophore glycosides: Wild cherry (e) Isothiocyanate glycosides: Black Mustard (f) Lactone glycosides: Cantharide (g) Aldehyde glycosides: Vanilla (h) Miscellaneous glycosides: Gentian, Quassia, Dioscorea

12. Cardioactive Glycosides Used in treatment of CHF Mechanism: These glycosides; Increase the force of systolic contraction Shorten length of systole As a result Heart have more time to rest between contraction. Therapeutic activity depends upon; 1. Chemical nature of aglycone 2. Number of sugars

13. Aglycone is steroidal Aglycone may be; Cardenolide (5-membered lactone at place of R) Bufanolide (6-membered lactone at place of R)

14. Digitalis Botanical Origin: Digitalis purpurea Digitalis lanata Family: Plantigenaceae / Scrophularaceae Part used: Dried leaves Collection: Leaves collected from 2 nd year growth of plant in June before opening of flower. Drying is done by applying artificial heat (temperature not more than 65°C).

15. ` Digitalis purpurea Digitalis lanata Oval or oblong Sessile Petiole winged Without petiole Dentate margin Straight margin Diameter 10cm Diameter 4cm Length 40cm Length 30cm

16. There are FIVE aglycone present in digitalis. Digitoxigenin………series A Gitoxigenin…………series B Digoxigenin………..series C Diginatigenin……..series D Gitaloxigenin………series E

17. DIGITOXIGENIN (series A)

18. 2. GITOXIGENIN (series B)

19. Derivatives Of GITOXIGENIN GITOXIN LANATOSIDE - B ( Digitalis purpurea) (Digitalis lanata)

20. 3. DIGOXIGENIN (series C)

21. 4. DIGINATIGENIN (series D)

22. 5. GITALOXIGENIN (series E )

23. ANTHRAQUINONE GLYCOSIDES

24. ALOE

25. Dried juice of leaves

26. ANTHRAQUINONE GLYCOSIDES

27. ALOE BOTANICAL ORIGIN: Aloe barbadensis FAMILY Liliaceae PART USED : Dried juice of leaves COLLECTION: Leaves are cut. They are placed in V- shaped funnel ,which are placed on an inclined. So that juice from leaves may led into the vessels this juice is then evaporated to a sufficient degree & then allow to harden. CONSTITUENTS: The main constituents are barbaloin or aloin. USES: Purgative Cathartic Juice is used for skin burn & skin irritation It is used in sun screen lotion cosmetic preparation & benzoin tincture.

28. CASCARA B.o : Rhamnus purshiana . Part Used: Dried bark Family: Rhamnaceae . Geographical Source:It is indigenous to North America, British Columbia, Canada and Kenya. Chemical Constituents: Cascara bark contains 80–90% of C-glycosides and 10–20% O-glycosides. The C-glycosides present in cascara are aloin or barbaloin and 11-deoxyaloin or chrysaloin . Cascarosides A and B are the primary glycosides of aloin and cascarosides C and D are primary glycosides of chrysaloin . Cascara also contains chrysaloin and barbaloins , dianthrones of emodin , aloe- emodin , chrysophanol ; heterodianthrones like Palmidins A, B and C, free emodin , aloe- emodin and a bitter lactone. Apart from glycosides it also contains fat, starch, glucose, volatile odorous oil, malic and tannic acids.

29. Cultivation & Collection It is an evergreen tree growing to 6–12 m in height. It requires moist soil. It is cultivated using different techniques like sowing seeds, cuttings and layering. Cuttings are carried out using half-ripe wood, July/August. Layering can be done in early spring. Earlier the barks were collected by felling technique and then by making longitudinal incisions on the trees. To save the destruction of this species nowadays it is collected by coppicing method. So the stump remaining above the soil produces new shoots, which bear leaves, flowers and fruits and seed dispersal takes place and new plants grow. Bark is collected from 9 to 15 years old trees having minimum 10 cm diameter in dry weather after rains in May to August by making suitable transverse and longitudinal incisions. During drying the outer bark is protected from moisture and rains and inner bark is protected from direct sunlight. Moisture leads to mould due to the sunlight bark becomes black colour . After complete drying the bark is made in to small pieces that form squill . It should be harvested in the autumn or spring at least 12 months before it is used medicinally, in order to allow the more violent purgative effect to be modified with age.

30. Uses It is majorly used due to its cathartic property because it promotes active movement of bowels. • it restores the natural tone of colon. • It is also used as a dietary supplement. • It is used as a gentle laxative. • It is used to treat chronic constipation. • It also have tonic properties. • It promotes gastric digestion and appetite. • It is also used to treat haemorrhoids and liver problems. • It is used to treat jaundice.

31. Rhubarb B.O: Rheum palmatum   Linn. P.used : dried rhizomes and roots Family: Polygonaceae . Geographical Source: It is mainly found in E. Asia, China in Yunnan, and India.

32. Chemical Constituents Rhubarb contains free anthraquinones , their glycosides, reduced derivatives, anthrones , or dianthrone and heterodi-anthrones . The anthraquinones of rhubarb are chrysophanol , aloe- emodin , emodin , physcion and rhein . Anthrones or dianthrones are of chrysophanol , emodin and aloe-emo-din. Heterodianthrones contain two different molecules of anthrones and they are from above anthrones . It also contains tannoid constituents, starch and calcium oxalate. There are also several resinous matters, one of which, Phaoretin , is purgative, and mineral compounds are also present. The astringency of Rhubarb is due to a peculiar tannic acid ( Rheo -tannic), which is soluble in water and alcohol

33. Uses • The main use of rhubarb is in the form of ointment, applied in the treatment of and cure of chronic eczema (atopic dermatitis) and psoriasis. • The root is taken internally in the treatment of chronic constipation, diarrhoea , liver and gall bladder complaints, haemorrhoids , menstrual problems and skin eruptions due to an accumulation of toxins. • It is used as a bitter stomachic in the treatment of diarrhea. • It also have purgative property. Externally, the root is used in the treatment of burns.

34. Senna B.O : Cassia aungustifolia , Cassia senna P.used : Dried Leaves Family: leguminosae Chemical Constituents Senna contains sennosides A and B (2.5%) based on the aglycones sennidin A and B, sennosides C and D which are glycosides of heterodianthrones of aloe- emodin and rhein are present. Others include palmidin A, rhein anthrone and aloe- emodin glycosides. Senna also contains free chryso phanol , emodin and their glycosides and free aloe- emodin , rhein , their monoanthrones , dianthrones and their glycosides. Mucilage is present in the epidermis of the leaf and gives red colour with ruthenium red .

35. Geographical Source Alexandrian senna ( Cassia acutifolia   Delile  )is indigenous to South Africa. It widely grows and sometimes is cultivated in Egypt and in the middle upper territories of Nile river. It is also cultivated in Kordofan and Sennar regions of Sudan. Indian or Tinnevelly senna ( C. angustifolia   Vahl .,) is indigenous to southern Arabia and cultivated largely in Tinnevelly and Ramnathpuram districts of Tamilnadu . It also grows in Somaliland, Sindh and Punjab region.

36. Uses Senna has purgative property. • It helps to increase peristalsis movement which also causes reduction in water absorption. • It has cathartic property. • It is used to treat chronic constipation. • It also has laxative property and senna is FDA- approved over –the- counter(OTC) laxative. • It is used to treat irritable bowel syndrome (IBS) and anal or rectal surgery. • It is used to treat hemorrhoids and weight loss. • It is an effective laxative in the condition of pregnancy and lactation.

37. SAPONIN GLYCOSIDES Glycyrrhiza Sarsaparilla

38. CHARACTERISTICS : They form colloidal solution with water. They have bitter taste except glycyrrhiza which is very sweet in taste. They destroy RBCs by hemolysis so, they are hemotoxin. They are extracted by hot water or alcohol. The aglycone part of saponin glycoside is sapogenin. They are toxic to cold blooded animals. e.g, fish poison.

39. 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. 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.

40. 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 saponin include their use in cleaning industrial equipment and fine fabrics and as powerful emulsifiers of certain resins, fats and fixed oils.

41. 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.

42. Structure of Saponins : According to the structure of the aglycone or sapogenin , two kinds of saponin are recognized: The steroidal type (commonly tetracyclic triterpenoids , C-27). 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.

43. GLYCYRRHIZA B.O: Glycyrrhiza glabra Family: Leguminoceae P.U: Dried root and rhizome COLLECTION: Rhizome and roots are collected from old plant and are air dried in spain . Crop is extracted with water and then is moulded into sticks. It is very sweet in taste. CONSTITUENTS: The chief constituent is glycyrrhizin which is a saponin glycoside upon hydrolysis it yield aglycone glycyrrhetinic acid and 2-glucoronic acid. USES: Expectorant, laxative, used in peptic ulcer, flavouring agent . Also used to mask the taste of drugs.

44. Glycyrrhizin

45. These glycosides upon hydrolysis yield HCN. They are mostly present in plants of family Leguminosae , rosaceae . They are derived from MANDELONITRILE. Prunasin is obtained from wild cherry bark. Amygdalin is obtained from almonds. CYANOGENETIC GLYCOSIDES

46. B.O: Prunus serotina Family: Rosaceae P.U: Dried bark. COLLECTION : Bark is collected in autumn and dried carefully in sun and kept in air tight containers. Color of bark is reddish grey, odourless but after hydrolysis give the odour of bitter almond(benzaldehyde). WILD CHERRY

47. Chemical Constituents Major cyanogenic glycoside is PRUNASIN(Which on hydrolysis yeild HCN and benzaldehyde and glucose) which is formed by the partial hydrolysis of AMYGDALIN which is also a cyanogenic glycoside obtained from bitter almond. It is accompanied by enzyme PRUNASE and form MANDELONITRILE. Other constituents are starch, tannins and resins. These glycosides have potential to be used as anticancer but owing to toxicity it is not recommended.

48. Therapeutic uses Astringent Tonic To treat bronchitis Expectorant Catarrh(disorder of inflammation of the mucous membranes in one of the airways or cavities of the body) Whooping cough Dyspepsia

49. These are the glycosides which on hydrolysis yield LACTONE. (Cantharides) Z.O: Cantharis vesicatoria Part Used: Dried insect. Collection: Insects are collected in JUNE & JULY , in morning when they are inactive. Plants are shaken with sticks and insects are collected on cloths spreading on the ground. The insects are killed by exposing to CARBON DISULPHIDE, CHLOROFORM or AMMONIA and finally dried at 40 °C. LACTONE GLYCOSIDES

50. Cantharidine. Other constituents are fats, fixed oils, uric acid and acetic acid. USES: counter irritant Rubifacient Use in hair oil & to remove warts Constituents

51. Cantharidin

52. These are glycosides which on hydrolysis yield aldehyde group. VANILLA B.O: Vanilla planifolia Family : Orchidaceae Part Used: Unripened fruits/vanilla beans. _ALDEHYDE GLYCOSIDES_

53. The fruits are collected and cured by dipping them in warm water. They are then sweated by placing them between woolen blankets in sun during day and packed in wool covered boxes. After two months the fruit loses 70-80% of its original weight and takes on the characteristic color and odour of commercial drug. Color is dark brown to violet black and taste is aromatic . Uses: Flavoring agent COLLECTION

54. Curing of vanilla Preparation for curing

55. Curing of vanilla

56. Vanillin

57. These are the glycosides which upon hydrolysis yield isothiocyanate ., e.g. BLACK MUSTARD ISOTHIOCYANATE GLYCOSIDES

58. Black Mustard Botanical origin: Brassica nigra Brassica juncea Family: Brassicaceae (cruciferae) Part used: Dried seeds Fixed oil obtained from mature seeds.

59. Sinigrin

60. CONSTITUENTS: Active constituent-sinigrin USES: Irritant Emetic Carminative

61. Miscellaneous glycosides Gention Quassia

62. Gentian Botanical origin: Gentian a lutea Family: Gentianaceae Part used: Dried rhizome and root Collection: Rhizome and roots are collected from 4-5yeas old plant in autumn and for drying, two methods are used; Quick drying process Slow drying process

63. DIOSCOREA B.O: Dioscorea villosa , D. composite; D.   spiculiflora ; D. deltoidea   and  D. floribunda, P.used : Dried Rhizome Family: Dioscoreaceae Geographical Source: It is mainly found in North America, Mexico, India ( Hima-layas from Kashmir and Punjab up to an altitude of 3,000 m), Nepal and China. Chemical Constituents: The roots contain diosgenin (4–6%) a steroidal sapogenin and its glycoside smilagenin , epismilagenin and beta isomer yammogenin . It also contains sapogenase (enzyme), phenolic compounds and starch (75%).

64. uses  This is widely used in modern medicine in order to manufacture progesterone and other steroid drugs. These are used as contraceptives and in the treatment of various disorders of the genitary organs (aphrodisiac) Can be used in the treatment of other diseases such as asthma and arthritis.

65. Quick drying process Drying is done immediately after collection, in sunlight. This drug contains bitter principle Gentiopicrin. Slow drying process Drying is done in open air. It takes 4-6 months for drug to dry completely. In this process, drug is allowed to ferment and loss most of its bitter principle and acquire aromatic quality that is desirable.

66. Chemistry: Active principle is Gentiopicrin. After hydrolysis, it produces; Gentiogenin Glucose Uses: Flavoring agent O O CH CH 2 C 6 H 11 O 5

67. Quassia Botanical origin: Picrasm a excels a Part used: Dried stem wood Collection: Drug occurs as cubes or chips. It is dried in an oven at temperature not more than 40°C. The drug is dried to protect from fermentation.It is odourless and taste is bitter.

68. Chemistry: Active principle is Quassin. Quassin is complex of; Picrasmin Neoquassin Uses: Bitter tonic Insecticide Anthelmintic

69. Cardio-active Glycosides Botanical Origin : Strophanthus   kombe   Oliv . Part Used : Dried Ripe Seeds Family : Apocynaceae Geographical source: The plant is indigenous to central East Africa, which serves principal commercial source of the drugs. Preparation: The ripe fruits are collected from the wild plants, the seeds are subsequently separated and freed from their awns. Chemical Constituents  The seeds of  strophanthus   usually contain  three  vital glycosides, namely: K- strophanthoside , K- strophanthride   b and  cymarin . Interestingly, all these glycosides undergo hydrolysis to yield  strophanthidin . Strophanthus

70. Cymarose Strophanthidine

71. Uses 1. It is used intravenously for treating emergency cardiac conditions. However, orally strophanthin is not so active. 2. These glycosides have been found to exert less cumulative effect unlike the digitalis glycosides. 3. Overall their therapeutic actions are very much similar to those of Digitalis. 4. Believed to have greater diuretic power, it is esteemed of greater value in cases complicated with dropsies.

72. White Squill B.O : Urginea indica Part Used : dried slices of the bulb Family: Liliaceae Common Names : Squill , Scilla Bulb, White Squill , European Scilla , Geographical Origin: It is mainly found in Spain, Portugal, Morocco, Algeria, Corsica, southern France, Italy, Malta, Dalmatia, Greece, Syria and Asia Chemical Constituents: Squill contains cardiac glycosides of bufadienolides types, scillaren A and B and enzyme scillatenase . The other con- stituents present are glucoscillaren A (cardiac glycoside), proscillaridin A, flavonoid, mucilage, volatile substances and sinistrin . The cardiac glycoside ( glucoscillaren A) on hydrolysis gives three glucose molecules, 2 molecules of glucose and a molecule of rhamnose along with scillarenin . Scillaren A is crystalline and responsible for the activity of the drug. Scillaren B is amorphous and its exact chemical structure is not known. Scillaren -A on hydrolysis with enzyme yields proscillaridin A and glucose.

73. Scillaren

74. Uses It is used as cardiotonic . • It has stimulant effect. • It also has the property of expectorant. • As expectorant it is used to treat asthma and chronic bronchitis. • It also has anticancer property • It also has diuretic properties. • It acts in similar manner to digitalis which slow and strengthen the pulse.