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Biosynthetic classification of alkaloids
Alkaloids are classified based on their biosynthetic precursors, which include amino acids like ornithine, tryptophan, lysine, phenylalanine, tyrosine, and histidine. Other precursors include purines. Major classes include tropane alkaloids from ornithine, indole alkaloids from tryptophan, quinoline alkaloids from tryptophan, papaver alkaloids from tyrosine, and purine alkaloids like caffeine, theobromine, and theophylline not derived from amino acids. Biosynthesis involves reactions like decarboxylation and transamination of amino acid precursors.
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Biosynthetic classification of alkaloids
- 1. BIOSYNTHETIC CLASSIFICATION OF ALKALOIDS Presented by : M. Jamal Email: jamalkhan616@gmail.com
- 2. Alkaloids • “Basicnitrogenous compound, contains one or more nitrogen in heterocyclic ring system having marked physiological action on human and animals when use in small quantities””. Classification of alkaloids • 1. Chemical classification of alkaloids • 2. Taxonomical classification of alkaloids • 3. Pharmacological classification of alkaloids • 4. Biosynthetic classification of alkaloids
- 3. Common aminoacid precursors: Phenylalanine Tyrosine Tryptophan Histidine Anthranilic acid Lysine Ornithine
- 4. BIOSYNTHETIC CLASSIFICATION OF ALKALOIDS Alkaloids are classified on the basis of biosynthetic precursors from which these are obtained . These include Ornithine derived alkaloids Tryptophan derived alkaloids Lysine derived alkaloids Phenylalanine derived alkaloids Tyrosine derived alkaloids Histidine derived alkaloids Alkaloids derived from substance other than amino acids.
- 5. General reactions forbiosynthesis of alkaloids • Some of the general reactions that are of particular importance include: decarboxylation (removal of carboxyl group or carbon dioxide) and transamination (transfer of an amino group from one molecule to another without the formation of ammonia) of the amino acids to yield a corresponding amine or aldehyde. • These can react to form a Schiff base which, in turn can react with carbanion in a Mannich-type condensation.
- 6. Alkaloid formation mayrequire the involvement of only one molecule of amino acid, or 2 molecules of the same AA, or less commonly, 2 molecules of different AA or else several molecules of the same AA.
- 8. ORNITHINE DERIVED ALKALOIDS It includes: Tropane alkaloids Pyrrolidine alkaloids`
- 9. TROPANE ALKALOIDS (ATROPINE,HYOCYAMINE, HYOSINE, SCOPOLAMINE) B.S: Atropa belladona (deadly nightshade), Datura stramonium( thornapple), Hyosyamus niger(henbane). Family: solanaceae Part used: dried leaves and flowering tops Uses: 1.Atropine is classified as anti cholinergic drugs. Atropine can also be used in SLUDGE syndrome( salivation, lacrimation, urination, diaphoresis, GIT motility and emesis) caused by organophosphate poisoning. Hyoscine is used as antispasmodic. COCAINE o B.S: Erythroxylum coca, Erythroxylum novogranatense o Common name. Coca leaves o Family: Erythroxylaceae o Part used: Leaves o Uses: cocaine is a CNS stimulant. it is also used as local anesthetic.
- 10. Biosynthesis of tropanealkaloids
- 11. TRYPTOPHAN DERIVED ALKALOIDS These include INDOLE ALKALOIDS QUINOLINE ALKALOIDS
- 13. Indole alkaloids Physostigmaalkaloids • Botanical source. Physostigma venonosum • Common name: calabar bean • Family : Leguminosae • Part used: dried ripe seeds • Main constituents: physostigmine , isophysostigmine, physovenine. • Uses: These are the cholinesterase inhibitors and used as antidote for atropine poisoning. • Also used to treat glaucoma. Ergot alkaoids B.S: Claviceps purpurea Family: Hypocreales Part used: Dried sclerotium of the fungus Main constituents: Ergotamine, Ergometrine, Ergocristine Uses: Ergotamine is used to treat migraine and clustur headache. Ergometrine acts as oxytocic agent and also used in post-partal haemorrhage. Vinca alkaloids B.S: Catharanthus roseus Common name: periwinkle Family: Apocynacea Part used: whole plant Constituents: Vincristine, Vinblastine Uses: these alkaloids have anticancer properties. Rauwolfia alkaloids B.S: Rauwolfia serpentina Common name: indian snakeroot Family: Apocyanacea Part used: leaves Constituents: serpentine, reserpine, ajmaline, ajmalacine, Uses: used as antihypertensive and antiarrhythmic agent.
- 14. Biosynthesis of Vincaalkaloids
- 15. Quinoline alkaloids B.S:Cinchona Succirubra, C. calisaya, C. officinalis Common name; Quina Family: Rubiaceae Part used: Dried Bark Constituents: Quinine, quinidine, cinchonine, cinchonidine. Uses: Quinine is a classical antimalarial. Quinidine is used for cardiac arrythmias and atrial fabrillation.
- 16. LYSINE DERIVED ALKALOIDS These include Lobelia spp pepper spp
- 17. Lobelia alkaloids •B.S: Lobelia inflata • Common name: indian tobacco • Family: Lobeliaceae • Part used: dried aerial parts • Constituents: lobeline, isolobeline, lobelanine, lobeladine • Uses: it is used in chronic bronchitis and spasmodic asthma. lobeline
- 18. Pepper alkaloids •B.S: Piper nigrum • Common name: black pepper, kali mirch • Part used: dried , unripe fruit • Family : Piperaceae • Constituents: piperine and piperittene • Uses: piper is used as condiment and for chronic bronchitis.
- 19. ALKALOIDS DERIVED FROMTYROSINE Isoquinoline alkaloids papaver alkaloids cephaelis alkaloids
- 20. Papaver alkaloids •B.S: Papaver somniferum • Family: papaveraceae • Part used: dried milky latex of poppy capsule. • constituents: Morphine, codiene, thebaine, Norcotine, Narciene, papaverine • Uses: Morphine is used as analgesic. codiene is used in cough preparations. Cephaelis alkaloids B.S: C.ipecacuanha Common name: Ipecac Part used: roots and rhizome Family: Rubiaceae Constituents: cephaline, psychotrine, Emetine, Uses: ipecacuanha is used as expectorant, and emetic and in the treatment of Ameobic dysentry. Emetine
- 21. BIOSYNTHESIS OF OPIUMALKALOIDS: ------- L-Dopa ------ Dopamine + 3,4 – dipydroxyphenylpyruvic acid PAPAVERINE ----------------- norlaudanosoline ( ket intermediate) Reticuline Saluteridine Saluteredinol
- 22. Alkaloids derived fromphenylalanine • EPHEDRINE, PSEUDOEPHEDRINE :- • B.S –It consists of dried young stem of Ephedra gerardiana and Ephedra nebrodensis. • Synonym—Ma-huang). • Family:- Ephedraceae • C.C:-- It contains the amino alkaloids : Ephedrine, nor-ephedrine, n-methyl ephedrine, pseudo-ephedrine. • Uses: it is used in Asthma, hay fever, flu, cold medications.
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- 24. HISTIDINE DERIVED ALKALOIDS These alkaloids include Imidazole alkaloids. e.g Pilocarpine
- 25. It is usedin the treatment of glaucoma and atropine poisoning.
- 26. Alkaloids obtained fromprecursors other than Amino Acids Purine alkaloids Purines are derivatives of a heterocyclic nucleus consisting of a six-membered Pyrimidine ring fused to a five-membered Imidazole ring. Purines are Psudo alkaloids (Are not derived from amino acids but have nitrogen in a heterocyclic ring)
- 27. Purine alkaloids xanthine coffeine theobromine theophyilline They are all methyl derivatives of xanthine.
- 28. Theobromine • B.S.Theobroma cacao • Family: sterculiaceae • Part used: seeds • Uses: Cocoa has nutritive, stimulant and diuretic properties. Theobromine is used as a diuretic. It has less action on the central nervous system than caffeine but is more diuretic.
- 29. Caffeine B.S: Coffeearabica Family: Rubiaceae Uses: caffeine is used in combinations with antipyretics and analgesics, cold and flu medication. also used as Ingredient in non-alcoholic beverages and “energizing” beverages.
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