Alkaloids
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This document discusses alkaloids, which are nitrogen-containing plant compounds. It defines alkaloids and explains that they are derived mainly from amino acids. The document then covers the different types of alkaloids based on their chemical structure, including heterocyclic and non-heterocyclic alkaloids. Examples are provided for each type. The document also discusses the extraction, properties, distribution in plants, and historical uses of alkaloids. It pays tribute to Dr. Hakim Ajmal Khan, an Indian physician who opened clinics where alkaloids were discovered and isolated.
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Alkaloids
- 1. 09/10/12 Dept of Ilmul Advia, NIUM1,Bangalore
- 2. Introduction Alkaloid –containing plants constitute an extremely varied group both taxonomically and chemically, a basic nitrogen being the only unifying factor for the various classes. Alkaloids are a group of nitrogen- containing bases. But few of them are derived from purines or pyrimidines, while the majority of them are produced from amino acids . 09/10/12 Dept of Ilmul Advia, NIUM2,Bangalore
- 3. Alkaloid is term defined from alkali-like , but this could not be defined well as these were derivatives from complex amins , typical alkaloid is derived from plant source They are basic They contain one or more nitrogen atoms. Have a marked physiological action either on man or on animal. 09/10/12 Dept of Ilmul Advia, NIUM3,Bangalore
- 4. The name prototype-alkaloid or amino alkaloid are applied to compounds such as hordenine, ephedrine and colchine which lack one or more properties of typical alkaloids. Others which contain synthetic compounds but are closely related 09/10/12 Dept of Ilmul Advia, NIUM4,Bangalore
- 5. Position The position of the nitrogen atom in the carbon ring varies with different alkaloids and with different plant families. In some alkaloids, such as mescaline, the nitrogen atom is not in a carbon ring. Nitrogen 09/10/12 Dept of Ilmul Advia, NIUM5,Bangalore
- 6. Graphical representation 09/10/12 Dept of Ilmul Advia, NIUM6,Bangalore
- 7. History The first isolations of alkaloids were in the nineteenth centuary. Prior to approximately 300 years ago the first one was NICOTINE .Malaria was the scourge of Europe, likely having been introduced through the Middle East. To over come the disease cinchona was used , this was the first breakthrough where in an alkaloid was isolated from the bark of cinchona the “QUININE” which is one among the 31 alkaloids obtained from the cinchona bark. 09/10/12 Dept of Ilmul Advia, NIUM7,Bangalore
- 8. Earliest alkaloids 1. Narcotine-1803 ----Tobacco 2. Morphine-1806 & 816—Opium 3. Strychnin-1817—Strychous 4. Emetine—1817-- 5. Brucine-1819---Strychous 6. Piperine– 1819-- 7. Caffine 1819--Coffee 8. Quinine 1820--Cinchona 9. Colchine 1820-- 10. Coniine -1826-Hemlock 09/10/12 Dept of Ilmul Advia, NIUM8,Bangalore
- 9. Coniine Coniine - 1826 was the first to have its structure established .It was done by Schiff in 1870 and synthesized by Ladenburg in 1889 09/10/12 Dept of Ilmul Advia, NIUM9,Bangalore
- 10. Distribution The alkaloid chemistry starts about 150 yrs back, by the mid 1940s there were about 800 Alkaloids isolated, with the new technologies by the next 50 yrs we have about 10,000 alkaloids isolated at present, there is more and more demand of the isolated alkaloids leading to the discovery of about 10 alkaloids per year. There is rare occurece in the lower plants like fungi but among the pteridophytes and gymnosperms the ephedra and taxus alkaloids have medicinal value. 09/10/12 Dept of Ilmul Advia, NIUM10 ,Bangalore
- 11. Commonly found in the orders of: • Centrospermae –(Chenopodiaceae) • Magnoliales (Lauraceae Magnoliaceae) • Ranuculales (Berberidaceae) • Papaverales (Papeverace) • Rosales (Leguminosae) • Rutales (Rutaceae) • Gentales (Apocynaceace) • Tubiflorae (Boraginaceae, Solanceae) • Campanulales (Campanulaceae) 09/10/12 Dept of Ilmul Advia, NIUM11 ,Bangalore
- 12. Centrospermae –(Chenopodiaceae) aaaa Chenopodium ficifolium - Fig-leaved Goosefoot 09/10/12 Dept of Ilmul Advia, NIUM12 ,Bangalore
- 13. Magnoliales (Lauraceae Magnoliaceae) Magnoliales 09/10/12 Dept of Ilmul Advia, NIUM13 ,Bangalore
- 14. Ranuculales (Berberidaceae) Berberis trifoliolata 09/10/12 Dept of Ilmul Advia, NIUM14 ,Bangalore
- 15. Properties • Well defined crystalline substances. • Unite to acids to form salts • They may exist in free state or as N-oxides. • Consists of elements carbon, hydrogen, and nitrogen . • Most of them contain oxygen. But a few of them are oxygen free , hence they are liquids .They are coniine from hemlock (Shukraan) and nicotine from tobacco (Tambaaku) 09/10/12 Dept of Ilmul Advia, NIUM15 ,Bangalore
- 16. Properties Apart from these there are a few of exception of colored alkaloids like. •Berberine-Yellow •Sanguinarine-Copper red 09/10/12 Dept of Ilmul Advia, NIUM16 ,Bangalore
- 17. Properties Solubility •The alkolidal salts are have good solubility in water than in a organic solvent. •Free bases are more frequently soluble in organic solvent than water. •They have their unique solubility property like—Quinine sulphate is only soluble in 1: 1000 parts of water. 09/10/12 Dept of Ilmul Advia, NIUM17 ,Bangalore
- 18. Structure and classification Based on the chemical structures there are two broad classifications. Heterocyclic or Non heterocyclic typical alkaloids or There are 14 types atypical alkaloids according to their Protal kaloids Ring structure. Biological amines 09/10/12 Dept of Ilmul Advia, NIUM18 ,Bangalore
- 19. Types 09/10/12 Dept of Ilmul Advia, NIUM19 ,Bangalore
- 20. Nonhetrocyclic Alkaloids Hordenine—germinating barley Mesoline --- Lophophora williamssi (Cateacea) Ephedrine-Ephedra spp (Ephedraceae) Cholachine—Colchium spp (Liliaceae) Erythromycin –Streptomyces erytreus (Bacteriophyta) 09/10/12 Dept of Ilmul Advia, NIUM20 ,Bangalore
- 21. Nonhetrocyclic Alkaloids 09/10/12 Dept of Ilmul Advia, NIUM21 ,Bangalore
- 22. Heterocyclic alkaloids Pyrrole and pyrolidine –coca spp (Erythroxylaceae) Hygrines---Solanceace Stachydrine- soya bean and other leguminosae 09/10/12 Dept of Ilmul Advia, NIUM22 ,Bangalore
- 23. Pyrrolizidine Symphitine, echimidine-----Symphytum spp Senecionine , seneciphylline , etc/---Senecio spp 09/10/12 Dept of Ilmul Advia, NIUM23 ,Bangalore
- 24. Pyridine and piperidine Trigonella----Fenugreek Coniine—Conium maculatum Arecoline----Araca catechu Lobeline---Lobeliaceae Pelletierine---Punica grantum Nicotine—Nicotiana tabacum Anabasine—Nicotiana glauca Pipernine---Piper spp Ricinine—Ricinus comunis 09/10/12 Dept of Ilmul Advia, NIUM24 ,Bangalore
- 25. Pyridine and piperidine 09/10/12 Dept of Ilmul Advia, NIUM25 ,Bangalore
- 26. Tropane Hyoscyamina,atropine---Dhatura Calystegines—convolvulus spp, Morus spp Cocaine—Cocoa species Pseudo pelletierine—Punica grantum 09/10/12 Dept of Ilmul Advia, NIUM26 ,Bangalore
- 27. Quinoline Quinine----Cinchona Cusparine----Angostura or cusparia 09/10/12 Dept of Ilmul Advia, NIUM27 ,Bangalore
- 28. Isoquinoline Papaverine,narcenia,narcotine—Papavera spp Corydaline--Corydalis Hydrastine , berberine—Numerous genera Emetine---Cephaaelis spp Tubocurarine—Curare Morphine—Papavera spp Erythraline—Erythrine spp Galanthamine—Leucojum aestivum 09/10/12 Dept of Ilmul Advia, NIUM28 ,Bangalore
- 29. Isoquinoline 09/10/12 Dept of Ilmul Advia, NIUM29 ,Bangalore
- 30. Aporphine Boldine---Peumus boldus 09/10/12 Dept of Ilmul Advia, NIUM30 ,Bangalore
- 31. Norlupinane Sparteine—Lupine alkaloids Cystine Lupanine Laburnine 09/10/12 Dept of Ilmul Advia, NIUM31 ,Bangalore
- 32. Indole or benzopyrrole Ergometrine---Claviceps Lysergic acid amine—Rivea corymbosa Physostigmine--Physstigma Ajmalina,serpentine , reserpine-Rauwolfia spp Yohimbine, as pidospermine—Aspidosperma spp Vimblastine –Catharanthus roseus Calabash---Strychnos spp Strychnine , brucin-- Strychnos spp 09/10/12 Dept of Ilmul Advia, NIUM32 ,Bangalore
- 33. Indole or benzopyrrole 09/10/12 Dept of Ilmul Advia, NIUM33 ,Bangalore
- 34. Indolizidine Castanospermine-castanspermum Swainsonine—swainsona spp 09/10/12 Dept of Ilmul Advia, NIUM34 ,Bangalore
- 35. Indazole Pilocarpine—Pilocarpus spp 09/10/12 Dept of Ilmul Advia, NIUM35 ,Bangalore
- 36. Purine Caffine—coca spp 09/10/12 Dept of Ilmul Advia, NIUM36 ,Bangalore
- 37. Theobromine Striodal Solanidine---Shoots of potato. Spp Veratrum alkamina –Veratrum spp Conessine—Holarrhea spp Funtumine—Funtumia spp 09/10/12 Dept of Ilmul Advia, NIUM37 ,Bangalore
- 38. Theobromine --Terpinod Aconite—Aconitum spp Atisine—Delphinium spp Lyctonie 09/10/12 Dept of Ilmul Advia, NIUM38 ,Bangalore
- 39. Pseudo alkaloids These are those alkaloids which are not derived from regular amines. 09/10/12 Dept of Ilmul Advia, NIUM39 ,Bangalore
- 40. Extraction of Alkaloids There are two major methods for the extraction of alkaloids. 80 70 60 50 Alkaloids 40 Water 30 Mineral 20 10 0 09/10/12 Dept of Ilmul Advia, NIUM40 1st Qtr ,Bangalore
- 41. Extraction of Alkaloids Process A Powdered material wa te r Alkaloids Lime 09/10/12 Dept of Ilmul Advia, NIUM41 ,Bangalore
- 42. Extraction of Alkaloids Process B Powdered material Water or aqueous alcohol containing dilute acid Chloroform Alkaloids Or other Organic solvents 09/10/12 Dept of Ilmul Advia, NIUM42 ,Bangalore
- 43. Tests for alkaloids Precipitation tests with reagents •Mayer’s-potassiomecric iodide •Hager’s –saturated solution of picric acid •Wager’s- solution-iodine in potassium iodide •Dragendroff ’s-solution of potassium bismuth iodide A few like caffine (a purine derivative ) does not precipitate with above reagents , hence it is detected by mixing the alkaloid material with small amount of Potassium chlorate and a drop of hydrochloric acid Purple color is obtained after evaporation of ammonia 09/10/12 Dept of Ilmul Advia, NIUM43 ,Bangalore
- 44. Functions of Alkaloids 1. Act as good potassium intake media. 2. Transport vehicle 3. Enzyme inhibition 4. To produce alkaloid free drug. 5. Foreign alkaloid 6. Plant metabolism 7. To reduce tissue damage. 09/10/12 Dept of Ilmul Advia, NIUM44 ,Bangalore
- 45. Alkaloids Dr. Hakim Ajmal Khan (1863–December 29, 1927) was a noted Indian freedom fighter, renowned physician and educationalist.Hakim Ajmal Khan and opened a 'dawakhana' in lahore which has its branches throughout Pakistan. It was opened under the name of 'Dawakhana Hakim Ajmal Khan Private Ltd' and is running ever since. Dr. Khan's descendants still live in Lahore. During his reign the alkaloids were discovered and isolated and as a tribute named after him by the then director Dr Salimuzaman Siddique (who was the director of research council). They were Ajmalinine and Ajmaline These were used for the treatment of aliments of nerves and brain , especially was a good Medicine for blood pressure. 09/10/12 Dept of Ilmul Advia, NIUM45 Amina Ather Dr ,Bangalore
- 46. Alkaloids Ajmalinine Ajmaline 09/10/12 Dept of Ilmul Advia, NIUM46 Amina Ather Dr ,Bangalore
- 47. Thank You Dr Aamina Ather 09/10/12 Dept of Ilmul Advia, NIUM47 ,Bangalore