Alkaloid turunan TryptophanAlkaloid turunan Tryptophan •Alkaloid kelompok ini mendapatkan perhatian khusus para ahli selama 2 dekade terakhir. •Hal disebabkan oleh bioaktifitas dan struktur kimia khususnya masalah biosintesis, stereokimia dan tantangan total sintesis yang sangat beragam dan kompleks. •Kelompok alkaloid ini banyak juga yang memiliki rantai/gugus samping yang biosintesisnya tidak sederhana. •Kelompok alkaloid ini banyak ditemukan pada famili Apocynaceae, Rubiaceae, Solanaceae dan Loganiaceae Yang termasuk alkaloid Tropan Atropin Hyosiamin Scopolamin Cocain Alkaloid tropan termasuk pada true allkaloid Alkaloid ini memiliki efek fisiologis, dimana dikenal sebagai bahan yang toksik (antagonis reseptor muskarinik) Biosintesis Indol dan tryptophan IAA Alkaloid indol . 05% alkaloids – hyoscyamine. Common names: Henbane .Hyoscyamus niger Solanaceae Definition: Hyoscyamus leaf consists of the dried leaves or dried leaves and flowering tops of Hyoscyamus niger. It should contain at least 0. Are very closely related to each other All have pronounced physiological actions. Natural alkaloids include Hyoscyamine Hyoscine Atropine Cocaine The above mentioned alkaloids occur within the Solanaceae family (except cocaine – from Erythroxylaceae family) . tropic or benzoic acid esters of tropine.Tropane Alkaloids Derived from tropine and consist of mandelic. . decreases sweating. Atropa belladonna: dilates eye pupils.Atropine & Hyoscine Have the same structure – differ only in their optical activity. Also have different physiological actions Atropine – deadly nightshade. . produces stomach acid and saliva & relaxes smooth muscle (asthma and colic). used in eye drops). Sedative Cocaine: Narcotic properties & local anaesthetic action (e. Hyoscine – black henbane.g. Hyoscyamus niger: Limited influence on the CNS. Hyoscine . Common names: Stramonium leaf. The drug should contain at least 0. Thornapple.Datura stramonium Solanaceae Definition: Stramonium Leaf consists of the dried leaves or dried leaves and flowering tops of Datura stramonium.25% alkaloids calculated as hyoscyamine. Jimson or Jamestown weed . and drug should contain no more than 3% of stems with a diameter >5mm .Datura stramonium Constituents Main (Tropane) Alkaloids * Hyoscyamine-Hyoscine (2:1) Younger plants: hyoscine – predominant alkaloid Also contains • Atropine • Larger stems contain little alkaloid. .Uses of Datura stramonium Atropine: Stimulant on CNS Depresses nerve endings on the secretory glands and smooth muscle Hyoscine: lacks CNS stimulant action of atropine Sedative – motion sickness Atropine & Hyoscine: used in opthalmic practice to dilate the pupil of the eye. Hyoscyamus niger Constituents Tropane Alkaloids Mainly • Hyoscyamine • Hyoscine (main constituent) . nonveined petals – bottom left). • Hyosycamus muticus (top right) • Hyoscyamus pusillus • Hyoscyamus aureus • Hyoscyamus reticulatus (Indian henbane – bottom right) .Hyoscyamus niger – Allied Drugs • Hyoscyamus albus (petiolate stem-leaves and pale yellow. Used to relieve spasm of the urinary tract .Hyoscyamus niger .Uses Resembles belladonna and stramonium in action – only weaker. Higher hyoscine content – less likely to cause cerebral stimulation . containing at least 0. USP also allows A.Atropa belladonna Solanaceae Definition: Belladonna herb consists of the dried leaves and flowering tops of Atropa belladonna. Should not contain >3% stem >5mm in diameter. acuminata in the Belladonna Leaf monograph. .3% alkaloids (hyoscyamine). Atropa belladonna Constituents Main (Tropane) alkaloid • Hyoscyamine Also contains • Scopoletin • Calcium oxalate . Atropa belladonna .g.Uses Used as a sedative To stop bodily secretions (e. saliva) Root preparations are used externally . . Pyridine Alkaloids Also referred to as Pyrrolizidine alkaloids Include Lobeline (Lobelia herb) – respiratory stimulant Used in asthma preparations. Nicotine (Nicotiana tabacum and other Nicotina spp) – toxic used as an insecticide Lobeline . Indian Tobacco) History: Traditionally used by the Native Americans for asthma. Capmanulaceae .Lobelia inflataDefinition: Lobelia herb consists of the dried aerial parts of Lobelia inflata. Common Names: Lobelia. Lobelia inflata – Constituents Contains Pyrrolizidine Alkaloids Most important • Lobeline Also Lobelidine Lobelanine Isolobelanine . . Caution: Toxic doses the herb has a paralytic effect.Uses Asthma Chronic bronchitis Anti-smoking preparations Injection of lobeline hydrochloride is used in the resuscitation of newborn infants.Lobelia inflata . racun panah Alkaloid b-carbolin Mis. Harman R=OH.Beberapa alkaloid sederhana turunan tryptophan R=H. Psilosin R=OPO3H2. Psilosibin Ditemukan pada jamur Psilocybe baeocystis Dikenal juga sebagai magic mushrooms Physostigmin. R=H.. Harmine Ditemukan pada biji Peganum harmala Memiliki aktifitas halucinogenic narcotic and anticarcinogenic . Ditemukan pada tumbuhan Physostigma venenosum Dikenal dengan bioaktifitas sebagai “reversible choline esterase inbhibitor. Alkaloid Indol Mrpk alkaloid yang mengandung cincin indol N Alkaloid ini bisa ditemukan pada Ergot & Nux vomica Alkaloid ergot berdasarkan adanya asam lisergat. Nux vomica. alkaloid pentingnya strycnine & brucine . Ergosine CH(CH3)2 CH(CH3)2 CH3 CH2CH(CH3)2 CH(CH3)2 CH2CH(CH3)2 CH2CH(CH3)2.Alkaloid peptida ergot Ergot dihasilkan dari jamur Claviceps purpurea yang tumbuh pada gandum secale cereale.10a-H2 6. 1. secale curnutum Mempunyai arti komersial penting. Dihydroergosine CH3 Bioaktifitas utama : vasokonstriksi dan uterotonik . Ergokryptine 4. Ergocornine 5. Ergotamine 2. yang menghasilkan asam lisergat Proline dan asam amino lain. 9. Ergocristine R1 CH3 CH(CH3)2 R2 CH2C6H5 CH2C6H5 3. Ajmalicine 2.Leurocrystine 7.Alkaloid indol monoterpenoid al: Alkaloid Asal Aktifitas farmakologis 1.Camptothecine 4.Deserpidine 5. Quinidine 8.Vincaleucoblastine 11.Ibogaine 6. Strychnine 10.Ajmalin 3.Vincamine Catharanthus roseus Hypotensive Ruwolfia sp Antiarrythmic Camptotheca acuminata Anticancer Rauwolfia canescens Hypotensives Tabernanthe iboga Psychotomimetic Catharanthus roseus Anticancer Remija sp Cardiac deppressant Rauwolfia vomitoria hypotensive Strychnos nux fomica CNS depressant Catharanthus roseus Anticancer Vinca major Hypotensives . Reserpin 9. 5-trimetoksisinnamoil 3.Camptothecine.4.5-trimetoksibenzoil 3.4. Amsonia. dikenal memiliki efek afrodisiak Alkaloid Rauwolfia. dari kulit kayu Corynanthe yohimbe. juga ditemukan pada berbagai tumbuhan lain spt Rauwolfia.4. Catharanthus dll Memiliki banyak stereoisomer. diisolasi dari Camptotheca acuminata Carcinogenic (sudah dipasarkan) Yohimbine. Aspidosperma.5-trimetoksibenzoil . Reserpin Rescinamine Desrpidin R1 OCH3 OCH3 H R2 3. b H -CH=CH2 a-OH. a-H.Cinchonidin 3. -CH=CH2 b-OH.Quinin 4.Quinidin b-OH. •Ekstrak kulit kina Sampai sekarang masih banyak \ •digunakan sebagai tonik 11 Alkaloidfa Strychnos Merupakan alkaloida yang ditakuti karena sangat beracun. -CH=CH2 R2 H H OCH3 OCH3 •Quinidin sampai sekarang masih merupakan obat penting untuk cardiac arrithmia. a H. Memberikan tantangan yang khusus bagi ahli kimia karena struktur yanng kompleks •11-OCH3 (brucine) .Cinchonine 2. b OH -CH=CH2 a-OH.Alkaloida utama Cinchona R1 1. VCR – human cancer VLB –hodgkin disease R = CH3 (1 g/ton) R = CHO ( 20 mg/ton) CH3O . Leurocrystine (VCR) .Alkaloida Catharanthus Telah berhasil diidentifikasi lebih dari 90 jenis Vincaleucoblastine (VLB). Isoprenoid alkalod . Alkaloid Solanum Alkaloid monoterpenoid. R = H. R = b-lycotetrose Bukittinggine (Sapium baccatum. (turunan loganin dan secologanin) Alkaloid sesquiterpenoid Alkaloid Diterpenoid Alkaloid Daphniphyllum 5 6 Tomatidin. D 5-6 Tomatin . nyatua batu) . R = H Solasodine.Alkaloid turunan isoprenoid Alkaloid steroid mis. sisa Alkaloid Purin Koffein Theophylline Theobromine CH3 CH3 H CH3 CH3 CH3 CH3 H CH3 .Alkaloid Gol. Alkaloid Gol. sisa Macrocyclic peptide alkaloids Mushrooms peptide alkaloids Saxitoksin .