Alkaloids PDF

ALKALOIDS AP. DR KHAIRANA HUSAIN NFNF1813 INTRODUCTION If najib hated Derived from Arabic “al kaly” (i.e. soda or basic) Define: Natural organic nitrogenous bases, found mainly in plants (also occur in microorganisms and animal), containing at least one nitrogen a...

ALKALOIDS AP. DR KHAIRANA HUSAIN NFNF1813 INTRODUCTION If najib hated Derived from Arabic “al kaly” (i.e. soda or basic) Define: Natural organic nitrogenous bases, found mainly in plants (also occur in microorganisms and animal), containing at least one nitrogen atom in a heterocyclic ring and physiologically active. basic 1 M atom Natural organic nitrogen bases in plants in neterocyclic atom  Op y g y INTRODUCTION nitrogen atom present: secondary, tertiary or 00 quaternary amines (rare in primary amine) Classified according to the nature of the basic nitrogen-containing structures from which they are derived (e.g: piperidine, quinoline, indole etc.) DISTRIBUTION AND OCCURRENCE  Dicots are more rich in alkaloids than Monocots.  Families rich in Alkaloids: Apocynaceae, Rubiaceae, Solanaceae and Papaveracea.  Families free from Alkaloids: Rosaceae, Labiatae lFree Labiatae Roof usaceae Apocynaceae FUNCTIONS  Defence mechanism Eaman anti  Nitrogenous source or waste bacteria WhFa  Most have pharmacological activities  CNS : depressant (morphine), stimulant (caffeine) o  Autonomic NS : sympathomimetic (ephedrine), sympatholytic (yohimbine), parasympathomimetic (pilocarpine), anticholinergic (atropine), ganglioplegic (nicotine)  Anaesthesia (cocaine), treat fibrilation (quinidine), antitumor (vinblastine), antimalaria (quinine), antibacteria (berberine), amebicide (emetine)  Starting materials for drug synthesis CLASSIFICATION OF ALKALOIDS Biogenetic Based on the biogenetic pathway that form the alkaloids :  acetate pathway or shikamate pathway Botanical Source According to the plant source of alkaloids. Type of Amines Primary, Secondary, Tertiary alkaloids. Basic alkaloids skeleton Isoquinoline Pyridine Wajib hafal piperidine TROPANE ALKALOIDS TROPANE ALKALOIDS basi need to know the basic anticholinergic activity Local anaesthetic antispasmodic & prevent motion sickness TROPANE ALKALOIDS  Local anaesthetic  Mostly used as drug of abuse to generate stimulation & euphoria but cause depression & dependence PIPERIDINE ALKALOIDS O O OH O N N Lobelin CH3 O Piperine Lobelia inflata Indian-tobacco PYRROLIZIDINE ALKALOIDS O OH O O O H OH N Acetyl-lycopsamine  inflammatory, rheumatic & GI disorders QUINOLIZIDINE ALKALOID N O N N N N HN O Lupinine Potentially toxic to humans INDOLIZIDINE ALKALOIDS Active against AIDS virus HIV OH OH OH H H OH HO OH N N HO Swainsonine Castanospermine contoh soalan What is the basic structure of this compound PYRIDINE ALKALOIDS N CH3 N Nicotine  Respiratory stimulant/depressant  Nicotine patch to assist stopping smoking habit Tobacco TETRAHYDROISOQUINOLINE ALKALOIDS H3CO H3CO N NH HO CH3 H3CO OR1 R2 Anhalamine (R1=H, R2=H) Lophocerine Anhalonidine (R1=H, R2=Me) Anhalomine (R1=Me, R2=Me) BENZYLTETRAHYDROISOQUINOLINE ALKALOIDS H3CO N H3CO Kratom H3CO H3CO opium poppy Papaverine  Used in expectorant & male impotence MODIFIED BENZYLTETRAHYDRO-ISOQUINOLINE ALKALOIDS Thebaine or Paramorphine morphine Codeine powerful analgesic & narcotic INDOLE ALKALOIDS N H Basic skeleton for indole alkaloid ERGOT ALKALOIDS IMIDAZOLE ALKALOIDS N N Pilocarpine Used as miotic eyedrop & treatment of glaucoma  PURINE ALKALOIDS 6 H 7 1 N 5 N 8 2 N 4 N 9 3 Purine Caffeine Theobromine Theophylline CNS stimulant Diuretic & smooth Smooth muscle relaxant 0 & weak diuretic muscle relaxant for relief of bronchospasm & diuretic  sinorine rene alkaloid have at least I N