Alkaloid - Wikipedia, the free encyclopedia

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From Wikipedia, the free encyclopedia

Alkaloids are a group of naturally occurring chemical compounds which mostly contain basic nitrogen atoms. This group also includes some related compounds with neutral[2] and even weakly acidic properties.[3] Also some synthetic compounds of similar structure are attributed to alkaloids.[4] Beside carbon, hydrogen and nitrogen, molecules of alkaloids may contain sulfur and rarely chlorine, bromine or phosphorus.[5] Alkaloids are produced by a large variety of organisms, The first individual alkaloid, morphine, including bacteria, fungi, plants, and animals and are part of the was isolated in 1804 from poppy group of natural products (also called secondary metabolites). (Papaver somniferum).[1] Many alkaloids can be purified from crude extracts by acid-base extraction. Many alkaloids are toxic to other organisms. They often have pharmacological effects and are used as medications, as recreational drugs, or in entheogenic rituals. Examples are the local anesthetic and stimulant cocaine, the stimulant caffeine, nicotine, the analgesic morphine, or the antimalarial drug quinine. Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly invoke a bitter taste.[6] The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut.[7] Compounds like amino acid peptides, proteins, nucleotides, nucleic acid, amines and antibiotics are usually not called alkaloids.[2] Natural compounds containing nitrogen in the exocyclic position (mescaline, serotonin, dopamine, etc.) are usually attributed to amines rather than alkaloids.[8] Some authors, however, consider alkaloids a special case of amines.[9][10][11]

1 Naming 2 History 3 Classification 4 Properties 5 Distribution in nature 6 Extraction 7 Biosynthesis 7.1 Synthesis of Schiff bases 7.2 Mannich reaction 8 Dimer alkaloids 9 The biological role 10 Applications 10.1 In medicine 10.2 In agriculture 10.3 Use as psychoactive drugs 11 See also 12 Notes 13 References

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2 of 19 23/11/2010 16:23 . coca leaves were used by South American Indians since ancient times. Several other alkaloids were discovered around that time.[5] If several alkaloids are extracted from one plant then their names often contain suffixes "-idine". etc. coniine (1827). A significant contribution to the chemistry of alkaloids in the early years of its development was made by the French researchers Pierre Joseph Pelletier and Joseph Bienaimé Caventou who discovered quinine (1820) and strychnine (1818). "-inine". caffeine (1820). It is believed that the gift was an opium-containing drug. Alkaloid-containing plants were used by humans since ancient times for therapeutic and recreational purposes.[18] Also. "-aline". sparteine (1851) and cocaine (1860). the term came into wide use only after the publication of a review article by O.[16] Studies of alkaloids began in the 19th century.[13] There is no unique method of naming alkaloids."like". For example.[nb 1] However.[20] The first complete synthesis of an alkaloid was achieved in 1886 by the German chemist Albert Ladenburg. atropine (1819).[15] History The article which introduced the concept of "alkaloid"."ashes of plants") and the suffix Greek: ειδοσ . Meissner. the German chemist who first isolated morphine from opium. such as aconitine and tubocurarine. colchicine (1833). In 1804. including xanthine (1817). atropine is isolated from the plant Atropa belladonna. the German chemist Friedrich Sertürner isolated from opium a "soporific principle" (Latin: principium somniferum).[14] Many individual names are formed by adding the suffix "-ine" to the species or generic alkaloids.[19] Extracts from plants containing toxic alkaloids. comes from the Arabic al qualja .htm 14 Bibliography Naming The name "alkaloids" (German: Alkaloide) was introduced in 1819 by the German chemist Carl F. Jacobsen in the chemical dictionary of Albert Ladenburg in the 1880s. which he called "morphium" in honor of Morpheus. He produced coniine by reacting 2-methylpyridine with acetaldehyde and reducing the resulting 2-propenyl pyridine with sodium. There are also at least 86 alkaloids containing the root "vin" (extracted from the Vinca plant).[12] and is derived from late Latin root Latin: alkali (which.Alkaloid . For example. a drug bringing oblivion.[16] The Odyssey of Homer referred to a gift given to Helen by the Egyptian queen.Wikipedia. the Greek god of dreams (the modern name "morphine" was given by the French physicist Joseph Louis Gay-Lussac). the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.[17] A Chinese book on houseplants written in 1st-3rd centuries BC mentioned a medical use of Ephedra and opium poppies. nicotine (1828). strychnine is obtained from the seed of Strychnine tree. "-anine".W. medicinal plants have been known in the Mesopotamia at least around 2000 BC. [21][22] The development of chemistry of alkaloids was accelerated by the emergence of spectroscopical and Friedrich Sertürner. in turn. were used since antiquity for poisoning arrows.

[29] Their characteristic examples are atropine. ergotamine[31]). Pseudalkaloids – alkaloid-like compounds which do not originate from amino acids. spermidine and spermine.. but are generally attributed to isoquinoline alkaloids.[24] for example. tryptophan. adrenaline and ephedrine..g. they require compromises in borderline cases. etc.[27] Alkaloids are often divided into the following major groups:[28] 1. tyrosine.[39] Main classes of monomeric alkaloids are listed in the table below: Bufotenin.Wikipedia.[23] Classification Compared with most other classes of natural compounds. nicotine contains a pyridine fragment from nicotinamide and pyrrolidine part from ornithine[26] and therefore can be assigned to both classes.[33] (left) and pyrrolidine 2. theobromine and theophylline. contains an indole core and is produced in living organisms from the amino acid tryptophan. Class Pyrrolidine derivatives[40] Major groups Main synthesis steps Examples Alkaloids with nitrogen heterocycles (true alkaloids) Ornithine or arginine → Hygrine.g.). hygroline. nicotine and morphine.g. putrescine → [40][42] N-methylputrescine → stachydrine 3 of 19 23/11/2010 16:23 . alkaloids are characterized by a great structural diversity and there is no uniform classification of alkaloids.[5][25] More recent classifications are based on similarity of the carbon skeleton (e.[5] However. This group also includes some alkaloids which beside nitrogen heterocycle contain terpene (e. which contain nitrogen in the heterocycle and originate from amino acids. Polyamine alkaloids – derivatives of putrescine. e. This group also includes piperidine The nicotine molecule alkaloids coniine and coniceine[32] although they do not originate from contains both pyridine amino acids. isoquinoline and pyridine-like) or biogenetic precursor (ornithine. Peptide and cyclopeptide alkaloids. 3.[37] Some authors classify as pseudoalkaloids such compounds such as ephedrine and cathinone.[34] 5.Alkaloid .[37][38] Some alkaloids do not have the carbon skeleton characteristic of their group. [29] acids.g. which contain nitrogen and also originate from amino rings (right). Examples include mescaline. This classification was justified by the lack of knowledge about the chemical structure of alkaloids and is now considered obsolete.[24] Historically. indole. lysine. 4. but acquire their nitrogen atom not from the amino acid but through transamination. galantamine and homoaporphines do not contain isoquinoline fragment. terpene-like and steroid-like alkaloids. evonine[30]) or peptide fragments (e. a poison from some toads. "True alkaloids". Those originate from the amino acid phenylalanine. So. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.[35] This group includes.000 alkaloids were identified. first classification methods combined alkaloids by the common natural source.[36] as well as purine-like alkaloids such as caffeine.htm chromatographical methods in the 20th century and by 2008 more than 12. "Protoalkaloids". a certain type of plants.

trichodesmine[46] 1-aminopyrrolizidines (lolines) In fungi: L-proline + L-homoserine → Loline. coniceine [33] Lupinine. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.Wikipedia.Alkaloid . N-formylloline. piperine [32][53] Coniine. nupharidin [54] Lupinine group Cytisine group Quinolizidine derivatives[54][55] Sparteine group Matrine group Ormosanine group Indolizidine derivatives[60] Lysine → δ-semialdehyde of α-aminoadipic acid → pipecolic acid → 1 indolizidinone [61] Simple derivatives of pyridine Nicotinic acid → digidronikotinovaya Lysine → cadaverine → ∆1-piperideine [56] Cytisine [54] Sparteine. anaferine. castanospermine [62] Trigonelline. arecoline [63][66] Pyridine derivatives[63][64] 4 of 19 23/11/2010 16:23 . allomatridine[54][57][58] Ormosanine. lobeline.htm N-methyl-∆1-pyrroline [41] Tropane derivatives[43] Atropine group Substitution in positions 3. piptantine[54][59] Swainsonine. 6 or 7 Cocaine group Substitution in positions 2 and 3 Ornithine or arginine → Atropine. N-(3-amino[50] 3-carboxypropyl)proline N-acetylloline → norloline[48][49] Lysine → cadaverine → ∆1-piperideine [52] Octanoic acid → coniceine → coniine [33] Piperidine derivatives[51] Sedamine. oxymatrine. sarracine [46] Platyphylline. laburnine [46][47] Pyrrolizidine derivatives[46] Indicine. anahygrine[54] Matrine. hyoscyamine[40][43][44] putrescine → N-methylputrescine → N-methyl-∆1-pyrroline Cocaine. scopolamine. ecgonine [41] [43][45] Non-esters Complex esters of monocarboxylic acids Macrocyclic diesters In plants: ornithine or arginine → putrescine → homospermidine → retronecine [41] Retronecine. lindelophin. ricinine. lupanine. heliotridine.

corydaline [79] Hydrastine. anabasine. amurensin [77] Derivatives of 5-naftilisoquinoline [74] Derivatives of 1. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. multifloramine [84] Bulbocodine [76] Phtalidisoquinolines [69] Spirobenzylisoquinolines [69] Ipecacuanha alkaloids[81] [69] Benzophenanthridines Aporphines [69] Proaporphines [69] Homoaporphines [84] Homoproaporphines [84] 5 of 19 23/11/2010 16:23 .2-dihydropyridine [65] Actinidine. sendaverine Cularine. mecambridine. coridine. oxynitidine. narcotine (Noscapine) [80] Fumaricine [77] Emetine. yagonine [76] Argemonine.and 2-benzylizoquinolines [75] Cularine group[76] Pavines and isopavines [77] Isoquinoline derivatives and related alkaloids [68] Benzopyrrocolines [78] Protoberberines [69] Tyrosine or phenylalanine → dopamine or tyramine (for alkaloids Amarillis) [70][71] Cryptaustoline [69] Berberine. noroxyhydrastinine [72] Cryptostilin [69][73] Ancistrocladine [74] Papaverine. ophiocarpine. pediculinine [67] Nicotinic acid. gentianine. lophocerine [68][69] Nicotine. glaziovine [69][78] Kreysiginine. liriodenine [83] Pronuciferine. laudanosine. ipecoside [81] Sanguinarine. anatabine N-methylcoridaldine. triptonine [64][65] Salsoline.htm Polycyclic noncondensing pyridine derivatives Polycyclic condensed pyridine derivatives Sesquiterpene pyridine derivatives Simple derivatives of isoquinoline [69] Derivatives of 1. protoemetine.Wikipedia.Alkaloid .and 3-isoquinolines [72] Derivatives of 1. nornicotine. canadine. hippocrateine. isoleucine [11] Evonine.and 4-phenyltetrahydroisoquinolines [69] acid → [63][66] 1. corynoloxine [82] Glaucine.

htm Morphines[85] Homomorphines [87] Tropoloisoquinolines [69] Azofluoranthenes [69] Amaryllis alkaloids [89] Morphine. erythroidine [73] Erythrite alkaloids[73] Phenanthrene derivatives [69] Protopins [69] Atherosperminine [69][79] Protopine. thiostreptone [94][96] Quinazoline derivatives[97] 3. glycosminine[99] Vazicine (peganine) [91] 6 of 19 23/11/2010 16:23 . imeluteine [88] Lycorine. halfordinol. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. oxomuramine.4-Dihydro-4-quinazolone derivatives 1. arborine. androcymbine [85] Imerubrine [69] Rufescine.4-Dihydro-4-quinazolone derivatives Pyrrolidine and piperidine quinazoline derivatives Anthranilic acid or phenylalanine or ornithine [98] Febrifugine[99] Glycorine. Muscimol Thiazole derivatives[94] 1-Deoxy-D-xylulose 5-phosphate (DOXP). tyrosine. codeine. thebaine. ambelline. corycavidine [82] Doriflavin [69] Aristolactam [69] Oxazole derivatives[91] Tyrosine → tyramine [92] Annuloline. tazettine.Wikipedia. montanine [90] Erysodine.Alkaloid . galantamine. texaline. texamine[93] Isoxazole derivatives Ibotenic acid → Muscimol Ibotenic acid. sinomenine [86] Kreysiginine. cysteine [95] Nostocyclamide.

psilocybin. etheramine. mitragynine. skimmianine[104] [109][110] Quinines Tryptophan → tryptamine → strictosidine (with secologanin) → korinanteal → cinhoninon [71][105] Non-isoprene indole alkaloids Quinine quinidine cinchonine. cinhonidine [108] Simple indole derivatives Simple derivatives of β-carboline [115] [111] Serotonin. evocarpine[104] Simple derivatives of quinoline derivatives of 2 . sarpagine. aquamicine. eptastigmine[116] Tryptophan → chanoclavine → agroclavine → Ergotamine.Wikipedia. vomicine [120] ) Tryptophan → tryptamine → Corynanthe type alkaloids[112] strictosidine (with secologanin) [112] 7 of 19 23/11/2010 16:23 .[118][119] group strychnine and (Strychnine brucine. dimethyltryptamine (DMT). acronicine[101][102] Cusparine. harmine.quinolones and 4-quinolone Tricyclic terpenoids Quinoline derivatives[103][104] Furanoquinoline derivatives Anthranilic acid → 3-carboxyquinoline [105] [106][107] Flindersine[104][108] Dictamnine. ajmaline. elimoclavine → ergosine[117] paspalic acid → lysergic acid [116] Semiterpenoid indole alkaloids See also: indole alkaloids Ergot alkaloids[86] Monoterpenoid indole alkaloids Ajmalicine. ergobasine. eleagnine [112] [111] 5-hydroxitriptofan Physostigmine (eserine).htm Acridine derivatives[91] Anthranilic acid [100] Rutacridone. yohimbine. echinopsine. tryptamine or harmaline.Alkaloid . fagarine. reserpine. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. bufotenin [113][114] Indole derivatives[86] Pyrroloindole alkaloids [116] Tryptophan → Harman. physovenine. vobasine.

ephedrine. nordihydrocapsaicin [133][135] Benzylamine[133] Putrescine derivatives[136] ornithine → putrescine → spermidine → spermine[137] Paucine [136] 8 of 19 23/11/2010 16:23 . cathinone. pseudoephedrine. epimuscarine. epiallomuscarine[131] Capsaicin. dopamine)[11][128] Colchicine alkaloids [129] Tyrosine or phenylalanine → dopamine → autumnaline → colchicine [130] Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[132] Phenylalanine with valine.2-dione → cathinone → ephedrine and pseudoephedrine [11][38][127] β-Phenylethylamine derivatives[78] Tyramine. ibogaine.Alkaloid .htm Iboga-type alkaloids[112] Aspidosperma-type alkaloids[112] Imidazole derivatives[91] Ibogamine. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. pilocarpine. dihydrocapsaicin.Wikipedia. noradrenaline. mescaline. aspidospermine[121][122] Histamine. leucine or isoleucine[134] Polyamines alkaloids Colchicine. vincotine. allomuscarine. colchamine[129] Muscarine [131] Muscarine. voacangine[112] Vincamine. stevensine[91][123] Directly from histidine[123] Purine derivatives[124] Xantosine (formed in purine biosynthesis) → Caffeine theobromine 7 methylxantosine → theophylline saxitoxin 7-methyl xanthine → [125][126] theobromine → caffeine [71] Alkaloids with nitrogen in the side chain (protoalkaloids) Tyrosine or phenylalanine → dioxyphenilalanine → dopamine → adrenaline and mescaline tyrosine → tyramine phenylalanine → 1-phenylpropane1. catecholamines (adrenaline. pilosine.

the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. arginine[143] Solasodine. solanidine. discarine D [138] Scutianine A type Amphibine F type Amfibine B type Amphibine F. scutianine J [138] Scutianine A [34] From different amino acids [34] Integerrine. spinanine A [34] Amphibine B.Wikipedia.Alkaloid . aphelandrine [136] Numularine C. veralkamine[144] Properties 9 of 19 23/11/2010 16:23 . numularine S [34] Ziziphin A.htm Spermidine derivatives[136] Spermine derivatives[136] Peptide (cyclopeptide) alkaloids Peptide alkaloids Numularine C type with a 13-membered cycle Ziziphin type [34][138] Frangulanine type Peptide alkaloids with a Integerrine type 14-membered cycle [34][138] Lunarine. lotusine C [34] Peptide alkaloids with a Mucronine A type 15-membered cycle [138] Mucronine A [31][138] Pseudoalkaloids (terpenes and steroids) Diterpenes [31] Licoctonine type Mevalonic acid → izopentenilpyrophosfate Aconitine. delphinine → geranyl [31][141] pyrophosphate [139][140] Steroids[142] Cholesterol. sativanine H [34] Frangulanine. codonocarpine[136] Verbascenine.

root (Rauwolfia serpentina) or bark (cinchona).htm Most alkaloids contain oxygen. animals in turn evolved the ability to detoxify alkaloids. the substance that was responsible for the deformities was identified as the alkaloid 11-deoxyjervine. It is believed that plants evolved the ability to produce these bitter substances. which play an important role in higher animals. those compounds are usually colorless crystals at ambient conditions. in the past the term "alkaloid" was associated with plants. in 1980s.[155] Some amines. oily liquids. such as adrenaline and serotonin.[153] Furthermore. such as bufotenin in the skin of some toads.2-dichloroethane. such as nicotine[145] or coniine. however. The cyclopia in the calf is induced by the alkaloid cyclopamine present in the plant. caffeine dissolves well in boiling water.[21] are typically volatile. such as diethyl ether.[147] Most alkaloids are poorly soluble in water but readily dissolve in organic solvents.[147] With acids. Those salts are usually soluble in water and alcohol and poorly soluble in most organic solvents. which is present in the leaves of corn lily. like berberine (yellow) and sanguinarine (orange). but some are amphoteric. such as psilocybin in the fungus of the genus Psilocybe. Distribution in nature Alkaloids are generated by various living organisms.Alkaloid .[146] Most alkaloids have a bitter flavor.[146] Some alkaloids are colored. up to 25% lambs born by sheep that had grazed on corn lily suffered serious facial defects. Depending on the type of plants. for example theobromine and theophylline). the maximum concentration is observed in the leaves (black henbane). Extraction 10 of 19 23/11/2010 16:23 . Those defects ranged from deformed jaws to cyclopia (see picture).Wikipedia.[148] Some alkaloids can produce developmental defects in the offspring of animals that consume them but cannot detoxify them. and in animals. which was renamed cyclopamine. chloroform and 1. colorless.[152] The alkaloids content in plants is usually within a few percent and is inhomogeneous over the plant tissues. During the 1950s. Exceptions include scopolamine hydrobromide which is soluble in organic solvents and water-soluble quinine sulfate.[150][151] Therefore.[146] Most alkaloid are weak bases. alkaloids form salts of various strengths.[14] Many marine organisms also contain alkaloids. especially by higher plants – about 10 to 25% of those contain alkaloids. in order to protect themselves from animals. After decades of research. However. many of which are poisonous.[154] Beside plants. A characteristic example is the alkaloid cyclopamine. alkaloids are found in certain types of fungi. Oxygen-free alkaloids. Its seeds are rich in strychnine and brucine. are similar to alkaloids in their structure and biosynthesis and are sometimes called alkaloids. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.[156] Strychnine tree.[149] Head of a lamb born by a sheep which ate leaves of the corn lily plant. fruits or seeds (Strychnine tree). different tissues of the same plants may contain different alkaloids.

. A base is then added to convert alkaloids to basic forms which are extracted with organic solvent (if the extraction was performed with alcohol. the impurities are dissolved by weak acids. lysine. histidine.[162] Synthesis of Schiff bases Main article: Schiff base Schiff bases can be obtained by reacting amines with ketones or aldehydes. and the opposite tendency of their salts.[157] Most methods exploit the property of most alkaloids to be soluble in organic solvents but not in water.[157][160] Alkaloids are separated from their mixture using their different solubility in certain solvents and different reactivity with certain reagents or by distillation. phenylalanine. Ways of alkaloid biosynthesis are too numerous and can not be easily classified. acetic acid in water.[162] Nicotinic acid can be synthesized from tryptophan or aspartic acid. such reactions may take place within a molecule. are proteinogenic. tryptophan. all these amino acids. Their mixture is extracted first and then individual alkaloids are separated. this converts alkaloid bases into salts which are washed away with water.htm Because of the structural diversity of alkaloids. tyrosine. except anthranilic acid. The solution is purified as described above. the raw plant material is processed by a weak acidic solution (e.2-dichloroethane. Most plants contain several alkaloids.[71] However. it is removed first. an aqueous solution of alkaloid salts is again made alkaline and treated with an organic solvent.[157][159] Most alkaloids are Crystals of piperine extracted from black pepper. If necessary. there is no single method of their extraction from natural raw materials. that is they are contained in proteins. aspartic acid and anthranilic acid.[158] Plants are thoroughly ground before extraction. such as ornithine.[162] such as in the synthesis of piperidine:[27] 11 of 19 23/11/2010 16:23 .[157] [158] The extracted alkaloids may remain salts or change into bases. Base extraction is achieved by processing the raw material with alkaline solutions and extracting the alkaloid bases with organic solvents. Then.Alkaloid .[164] In the biosynthesis of alkaloids. present in the raw plants in the form of salts of organic acids.Wikipedia. The process is repeated until the desired purity is achieved. diethyl ether or benzene. including synthesis of Schiff bases and Mannich reaction.[163] These reactions are a common method of producing C=N bonds. there are a few typical reactions involved in the biosynthesis of various classes of alkaloids.g. such as 1. and the remainder is dissolved in water). chloroform. In the acidic extraction.[161] Biosynthesis Biological precursors of most alkaloids are amino acids. ethanol or methanol). the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.

Lactonization (carpaine).Wikipedia. in addition to an amine and a carbonyl compound. Voacamine Villalstonine Toxiferine 12 of 19 23/11/2010 16:23 .htm Mannich reaction Main article: Mannich reaction An integral component of the Mannich reaction. there are also dimeric. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. three and four monomeric alkaloids.[164] The Mannich reaction can proceed both intermolecularly and intramolecularly:[165][166] Dimer alkaloids In addition to the described above monomeric alkaloids. tubocurarine).Alkaloid .. is a carbanion. and even trimeric and tetrameric alkaloids formed upon condensation of two. which plays the role of the nucleophile in the nucleophilic addition to the ion formed by the reaction of the amine and the carbonyl. e. voacamine Michael reaction (villalstonine). resulting in. Condensation of aldehydes with amines (toxiferine).g. Dimeric alkaloids are usually formed from monomers of the same type through the following mechanisms:[167] Mannich reaction. Oxidative addition of phenols (dauricine.

dopamine and histamine are important neurotransmitters in animals. and thus when the first alkaloids were synthesized in the 19th century. some animals adapted to alkaloids and even use them in their own metabolism. they immediately found application in clinical practice. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.[7] Most of the known functions of alkaloids are related to protection. hyoscyamine anticholinergic Action vasodilating. including the following:[7][172]: Alkaloid Ajmaline Vinblastine. scopolamine. presence of alkaloids in the plant prevents insects and chordate animals from eating it. usually in the form of salts.Alkaloid . aporphine alkaloid liriodenine produced by the tulip tree protects it from parasitic mushrooms.[171] Many alkaloids are still used in medicine. and urea in mammals.[168] Initially it was assumed that the alkaloids are the final products of nitrogen metabolism in plants. In addition.Wikipedia. Later it was shown that alkaloid concentrations varies over time and this hypothesis was refuted. For example. However.htm Dauricine Tubocurarine Carpaine The biological role The role of alkaloids for living organisms which produce them is still unclear. vincristine Vincamine Codeine Cocaine Colchicine Morphine Reserpine Tubocurarine Physostigmine antiarrhythmic antitumor Atropine. Alkaloids are also known to regulate plant growth.[169] Such alkaloid-related substances as serotonin. antihypertensive cough medicine anesthetic remedy for gout analgesic antihypertensive Muscle relaxant inhibitor of acetylcholinesterase 13 of 19 23/11/2010 16:23 .[170] Applications In medicine Medical use of alkaloid plants has a long history.

pp. some alkaloids. die bis jetzt bekannten Pflanzenstoffe nicht mit dem Namen Alkalien. da sie doch in manchen 14 of 19 23/11/2010 16:23 . and later pure alkaloids have long been used as psychoactive substances.[175] Use as psychoactive drugs Preparations of plants containing alkaloids and their extracts.htm Quinidine Quinine Emetine Ergot alkaloids antiarrhythmic antipyretics. were used as insecticides. an opioid receptor antagonist. 25. naloxone. Journal für Chemie und Physik. Cocaine and cathinone are stimulants of the central nervous system. Meissner (1819) "Über Pflanzenalkalien: II. antihypertensive Many synthetic and semisynthetic drugs are structural modifications of the alkaloids. 377–381] Meissner wrote "Überhaupt scheint es mir auch angemessen. vol. but are precursors for semi-synthetic psychoactive drugs.Alkaloid .[180] There are alkaloids that do not have strong psychoactive effect themselves.[181] See also Amine Base (chemistry) Natural products Secondary metabolite Notes 1. For example. vasodilator. sondern Alkaloide zu belegen. Their use was limited by their high toxicity to humans. which were designed to enhance or change the primary effect of the drug and reduce unwanted side effects. is a derivative of thebaine which is present in opium. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.Wikipedia. ^ In the penultimate sentence of his article [W. ephedrine and pseudoephedrine are used to produce methcathinone (ephedrine) and methamphetamine.[178][179] Morphine and codeine are strong narcotic pain killers.[173] For example. dimethyltryptamine and ibogaine) have hallucinogenic effect. such as salts of nicotine and anabasine. On a new plant alkali (alkaloid)).[174] Thebaine Naloxone In agriculture Prior to the development of a wide range of relatively low-toxic synthetic pesticides. antimalarial antiprotozoal agent sympathomimetic.[176][177] Mescaline and many of indole alkaloids (such as psilocybin. Über ein neues Pflanzenalkali (Alkaloid)" (On plant alkalis: II.

p. 12 29. 41. Volume VIII. Jones and The Alkaloids. p. p. F. New Age International. 2004. ^ a b c Dewick. 30 ISBN 0-8493-2976-0 9. since they differ greatly in some properties from the alkalis. Cseke Natural Products from Plants ( 7. p. ^ a b c d Hesse. p. p. ^ Biographical information about German pharmacist Carl Friedrich Wilhelm Meißner (1792-1853) is available in the German Wikipedia: http://de. p.wikipedia.1351%2Fgoldbook) 3. ^ Hesse. 204 23." (In general. D. p. doi:10. clinical and environmental toxicology (http://books.) References 182 17. ^ a b c d Aniszewski. ^ a b Aniszewski. ^ a b Hesse. Meyers Encyclopedia of Physical Science and Technology.doi. 307 28.iupac. Chemical Diversity of 24. p. ISBN 0-12-597180-X. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. ^ Raj K Bansal A Text Book of Organic Chemistry (http://books.New York: Academic Press. ^ Hesse. ^ Rhoades. ^ Leland J.html) (in German). ^ Hesse. among the chapters of plant chemistry.CRC. ^ A. Gregory G. Wilkinson.1039/NP9971400075 (http://dx. 11 25. New York: Academic Press. ^ a b TSB: Coniine (http://slovari. ^ a b Plemenkov. sie würden daher in dem Abschnitt der Pflanzenchemie vor den Pflanzensäuren ihre Stelle finden. they would therefore find their place before plant acids [since "Alkaloid" would precede "Säure" (acid)]. ^ Hesse. Prod. p. 1–3 . 433 ISBN 0-7637-0432-6 10.htm Eigenschaften von den Alkalien sehr 6 /?id=MtOiLVWBn8cC&pg=PA20.Alkaloid . Manske. p. p. William Johnson Invitation to Organic Chemistry (http://books. Blackwell Scientific . 51 ISBN 1-56670-223-2 5. In Rosenthal. p.Wikipedia. ^ Begley Encyclopedia of Chemical Biology: Natural Products in Plants. pg=PA433) . ^ Aniszewski.1351/goldbook (http://dx. ^ a b Hesse. p. 338 18.. pg=PA51) . "Cyclopeptide alkaloids". ^ Robert Alan Lewis. pp. Oxford (1997) ISBN 0-9678550-9-8 doi:10. 108 31. 2nd ed. Lewis' dictionary of toxicology (http://books. 14 (1): 75–82. ^ a b Hesse. Daniel H. p. ^ a b c Robert 15 of 19 23/11/2010 16:23 . Gerald A. p. ^ Aniszewski. . Chemistry and Physiology. Nat. p. 109 27. 1999. 13. ^ Hesse. it seems appropriate to me to impose on the known plant substances not the name "alkalis" but "alkaloids". Laskarisb and Robert Verpoorte (1997).com/books?id=wV2T41nGFc4C& pg=PA30) Second Molecular. p.htm) 22. and Janzen. ^ R. 2. ^ Orekhov. 644 ISBN 81-224-1459-1 11. p. 31 33. Rep. p. p. 381 34. 313–316 110 12. ^ Hesse. 1998. David F (1979). Eighteen-Volume Set. 20. Compendium of Chemical Terminology (http://goldbook.Alkaloids ISBN 0-12-227411-3 8. ^ Hesse. ^ a b IUPAC. 5 15.xumuk. ISBN 3764383356. ^ a b c d Chemical Encyclopedia: alkaloids (http://www. Compiled by A. (The "Gold Book"). Springer. "Evolution of Plant Chemical Defense against Herbivores". 2006. 304 19. 1965. ^ a b c d e f g h i Dimitris C.doi. 223 30. 84 32. 350 20. 4th Edition. Third Edition. ^ a b Dewick. Herbivores: Their Interaction with Secondary Plant Metabolites. p. 673 pg=PA644) . p. CRC Press. ^ Hesse. http://books. McNaught and A.html) . 7 16. pp. ^ Andreas Luch (2009).com /?id=MtOiLVWBn8cC&pg=PA20) .

1971. 44. 37.London: The Chemical Society. Begley. 42. 76.1002/cbic.London: The Chemical Society. Michael (2002). Saxton The Alkaloids.xumuk. 69. Mallik UP (2007). 37 ^ Hesse. p. ^ Schardl p. 1973. PMID 17346759 (http://www.1039/b208137g (http://dx. 92 ^ Dewick. 67. p. A Specialist Periodical Report. Volume 1. p. 12 ^ a b Dewick. Chembiochem 7 (7): 1078–1088. E. 224 ^ a b c Aniszewski. Saxton The Alkaloids. "Biosynthetic precursors of fungal pyrrolizidines. /10.phytochem. 56. p. p.htm 35. 52.html) ^ J.1016%2Fj.01.ncbi. doi:10. Grossman RB.xumuk. 62. Bush LP. 60. Schardl CL (2006). 57. Pal S. 38. /10. Nat.London: The Chemical Society.2007. . 1971.1039%2FNP9971400075) . p.html) ^ Aniszewski. 71. 73. p. 65.ncbi. 58. "Loline alkaloids: currencies of mutualism".doi.200400327) . p. 93 ^ Aniszewski. 41. 68. pp.phytochem. 97 ^ a b c Plemenkov.html) ^ a b Aniszewski. p. 46 16 of 19 23/11/2010 16:23 . . p. Blankenship JD. . 310 ^ Aniszewski. 61. A Specialist Periodical . 34 ^ Aniszewski. E. 246 ^ a b Aniszewski.html) ^ Plemenkov. 47.200600066) .nlm. 43.ncbi. 49. the loline alkaloids".010) . p. 75 ^ Orekhov. 53. "Indolizidine and quinolizidine alkaloids".1039%2Fb208137g) . 63. 44. Volume 3. . 59. ^ . pp.xumuk. Schardl CL (2005). 107 ^ a b Aniszewski. p. 77–78 ^ a b c d Tadhg Grossman RB. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. 382 ^ Hesse.xumuk. Saxton The Alkaloids. Nagabhyru P. 72. 85 ^ Plemenkov. Volume 1. 75. ^ Aniszewski. 53 ^ a b c Plemenkov. doi:10. /encyklopedia/1642. p. 27 ^ a b c d Chemical Encyclopedia: Pyrrolizidine alkaloids (http://www. 40. 80 ^ a b c d e f Chemical Encyclopedia: Quinolizidine alkaloids (http://www. 51.London: The Chemical Society. p. 38 ^ a b c Hesse. 70. p.doi. Prod. Grossman RB. p.nlm. PMID 9121730 (http://www. p.doi. PMID 15861432 (http://www. 55. 50. p.Wikipedia. E. p. 36. 66.ncbi. doi:10. 122 ^ a b c Hesse. . 54 ^ a b Hesse. Saxton The Alkaloids. A Specialist Periodical Report. A Specialist Periodical Report. p. 48. ^ Faulkner JR. Chembiochem 6 (6): 1016–1022. 33 ^ a b c Chemical Encyclopedia: Tropan alkaloids (http://www. 39.nlm.1002/cbic.1016/j. 228 ^ a b Hesse. p. p.nlm. 95 ^ Orekhov. ^ Plemenkov.010 (http://dx.html) ^ Hesse. Rep 19: 458–475. 36 ^ a b c d e f g h i j k l m n o p q r s t Chemical Encyclopedia: isoquinoline alkaloids (http://www. 91 ^ Joseph P.nih. 74. Pal S.nih.01.Encyclopedia of Chemical Biology: Alkaloid Biosynthesis ^ a b J. Volume 1. Phytochemistry 68 (7): 980–996. p. "On the sequence of bond formation in loline alkaloid biosynthesis". 225 ^ Aniszewski.200400327 (http://dx. 229 ^ Blankenship JD.Alkaloid . 227 ^ a b Chemical Encyclopedia: pyridine alkaloids (http://www. p. p. p. PMID 16755627 (http://www. 46. 98 ^ J. Houseknecht JB.200600066 (http://dx. 96 ^ Aniszewski. Hussaini SR. p. Branan BM. Faulkner JR. 11 ^ Plemenkov.

p. Begley. pp. ^ Chemical Encyclopedia: Quinazoline alkaloids (http://www. Richard B. A Specialist Periodical Report. 79. Volume 35. p. 44 84. 52 90. p. ^ Hesse. . 205 107.doi. ^ a b Hesse. p. p. E.London: The Chemical Society.asp?doi=a809403i) . 55 108. 1973. ^ Hesse. ^ Dewick.1039/NP9971400387 (http://dx. 231 104. E. . ^ a b Aniszewski. muscarine. ^ Tadhg P. p. p. A Specialist Periodical Report. E. p. ^ a b Aniszewski.html) p.asp?doi=a809403i. ^ a b c d Chemical Encyclopedia: Quinoline alkaloids (http://www. . 106 99. 236 87. imidazole. 17 of 19 23/11/2010 16:23 . . 15 114.Academic Press. ^ a b c Hesse. ^ a b Hesse. 1989.1039/a705734b (http://dx. 39 81. ^ Hesse. . http://www. doi:10.1039/a809403i (http://dx. Rep 14 (4): 387–411. 242 95. and other miscellaneous alkaloids" (http://www. p. 47 80.Encyclopedia of Chemical Biology: Cofactor Biosynthesis 96. ^ a b c d e Plemenkov. Prod. ^ a b Hesse.asp?doi=a705734b) . Rep 17 (1): 57–84. Volume 35.1039%2Fa705734b) .Academic Press. ^ a b c Aniszewski. 29 118. Rep 16: 199–208. Saxton The Alkaloids. Volume 3. p.Alkaloid .xumuk. ^ Orekhov. p. /NP/article. 231. p. 261 93. ^ a b c Kenneth W. 114 106. Herbert. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.nlm. thiazole and peptide alkaloids. ^ a b c d e f Aniszewski.Wikipedia.rsc.ncbi. .org/10.London: The Chemical Society.1039%2Fa809403i) . 113 Saxton The Alkaloids. 49 83. p. Richard B. p. p. . Prod. p. 241 92. "The biosynthesis of plant alkaloids and nitrogenous microbial metabolites" (http://www. ^ Richard B. ^ a b Plemenkov. p. p. doi:10. p.rsc. 50 78. 118 . 58 103. ^ J. "β-Phenylethylamines and the isoquinoline alkaloids".html) 105. ^ Aniszewski. p.London: The Chemical Society. ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology. 349-350 116. 1973. ^ Hesse. Volume 1. ^ Hesse.nih.doi. 105 100. "Amaryllidaceae. 246 102. 119 117. Volume 3. ^ J. ^ Plemenkov. ^ a b Plemenkov. Lewis (2000). ^ J. p. ^ John R. ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology. ^ J.htm 77. Saxton The Alkaloids.doi.London: The Chemical Society. 232 109. 260–263 94. ^ Hesse.asp?doi=a705734b. ^ a b Hesse. p. 212 110.xumuk. p. ^ Plemenkov. 97. 1971. E. ^ Hesse. 1973. ^ Hesse. PMID 10714899 (http://www. 51 86. /publishing/journals/NP/article. A Specialist Periodical Report. ^ a b c J. Herbert. p. 53 91. 1989. 168 89. Nat. ^ a b c Plemenkov. ^ Aniszewski. A Specialist Periodical Report. A Specialist Periodical Report.ncbi. Saxton The Alkaloids. Saxton The Alkaloids. ^ Hesse. .London: The Chemical Society. Prod.rsc. 101. Nat. 23-26 119.nlm. 164 85. ^ a b Aniszewski. p. p. 41 82. pp. Bentley (1997). PMID 9281839 (http://www. ^ Orekhov. Nat.rsc. p. 163 88.nih. p.. oxazole. Volume 1. 467 115. p. E. . (1999). p. 112 112. Volume 3.

Alkaloid .4 153. Volume 2001 (http://books. ^ Atta-ur-Rahman and M. p. ^ Dewick. ^ Aniszewski.doi. 73 126. ^ a b G. p. 122-123 154. . 53 149. p. 254 164. 142. pp. ^ Aniszewski. Prod. ^ a b c Plemenkov. CABI. ^ J. 110–111 157. 376 133.chem. doi:10. ^ a b c d Hesse. ^ Plemenkov. 243 139. p. 1984. 247 145. 305 18 of 19 23/11/2010 16:23 . Volume 23. ^ Spermine Biosynthesis (http://www. ^ Hesse. 268 135.asp?doi=NP9971400191. p. 134-136 162. 388 144.rsc. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. Volume 5. Spiller Caffeine (http://books. ^ Grinkevich.nlm. ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology. 131 147. 1975.Academic /NP/article. W. object=PWY-5883) 128. . 81 132. 357 123. ^ Chemical Encyclopedia: Terpenes (http://www. Iqbal Choudhary (1997).htm p.html) .Wikipedia. ^ Dewick. 396 127. . ^ /publishing/journals/NP/article. A.htm) 146. XVII 156. ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology. pp. p. p. 72 125. 132-134 161. 19 165.ncbi.1039/np9971400191 (http://dx. ^ Orekhov. ^ Grinkevich.Academic Press. 77 131. ^ a b ^ Grinkevich. p. p. ^ Dewick. ^ p. 210 121. ^ Plemenkov.html) . Colin S. T. 231 136. 11 152.asp?doi=NP9971400191) . ^ Aniszewski. p. 362.London: The Chemical Society. 150. p. 5 160. p. 17-18 122. p. p. p. ^ Tadhg P. 12 155. 1997 ISBN 0-8493-2647-8 148. ^ of Chemical Biology: Natural Products: An Overview 141. 255 166. 253 163. ^ a b Hesse. 76 129. Volume 23. ^ Thomas Acamovic. 82 137. p. E. Begley. 104 124. 77 134. ^ a b c d e f Hesse. 132 159. .xumuk. http://books. CRC Press. ^ Hesse. ^ TSB: Nicotine (http://slovari. Pennycott (2004). p. "Diterpenoid and steroidal alkaloids" (http://www. p.html) 130. p. Stewart. Saxton The Alkaloids. A Specialist Periodical Report. p. pp. ^ a b Chemical Encyclopedia: colchicine alkaloids ( ^ Hesse. ^ a b Aniszewski. ^ Orekhov. ^ Hesse. ^ ^ Fattorusso. ^ a b c d e f Plemenkov.nih. p. p. 1984. Nat. Volume 23. ^ a b Grinkevich. ^ Dewick. p. 116 158.plantcyc.Academic Press. p. p. ^ a b c Grinkevich. 1984. pp. p. PMID 9149410 (http://www. 169 120. Rep 14 (2): 191–203. p. p. 88 ^ Hesse. p. 13 151. ^ PlantCyc Pathway: ephedrine biosynthesis (http://www. . ISBN 0851996140. ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology.rsc. ^ a b Dewick.xumuk.1039%2Fnp9971400191) . Poisonous plants and related toxins.

cnshb. M. Wiley-VCH. The chemical analysis of medicinal plants: Proc. ISBN 978-0-471-75477-0. 181. Amsterdam: Elsevier. Fattorusso and O. B. Wiley. p. AE Kovalenko Drugs.shtm) . 142-143 ^ Hesse.: Triada-X. 303-309 ^" Categories: Metabolism | Alkaloids This page was last modified on 8 November 2010 at 11:39. 75 ^ Hesse. Paul M Dewick (2002). 178. additional terms may apply. 19 of 19 23/11/2010 16:23 . 2 ed. pp.htm 167. Introduction to the Chemistry of Natural Compounds. M. M. Viktor Andriska Pesticide chemistry (http://books. 169. Chemistry alkaloids (Acad. p. allowance for pharmaceutical universities. Begley (2009). Tadhg /RA/140004. Manfred Hesse (2002). pp. p. 180. Alkaloids: Nature's Curse or Blessing?. 176. 174.shtm. 6 ^ Veselovskaya. 79 ^ Veselovskaya. Chemical Encyclopedia (http://www. p. Orekhov AP (1955). 283-291 ^ Aniszewski. 175. 51-52 Bibliography Tadeusz Aniszewski (2007). Elsevier. pp. Modern Alkaloids: Structure.wikipedia. Plemenkov VV (2001). Elsevier.Wikipedia. ISBN 978-3-527-31521-5. Encyclopedia of Chemical Biology.). 303 ^ Hesse. p.: USSR. p.Alkaloid . Wiley. Alkaloids . Isolation. 173. Taglialatela-Scafati (2008). Medicinal Natural Products. See Terms of Use for ^ Hesse. 2000 Retrieved from "http://en. Soviet /books?id=fPiRSsUOpLEC&pg=PA21) . N. 91–105 ^ Aniszewski.. Grinkevich NI Safronich LN (1983). 142 ^ Hesse. Veselovskaya. 170. p. ISBN 978-3-906390-24-6. ISBN 0471496405. Cordell The Alkaloids: Chemistry and Biology. 335 ^ György Matolcsy. 2001. A Biosynthetic Approach. ISBN 978-0-444-52736-3. Inc. a non-profit organization.cnshb. 21-22 ISBN 0-444-98903-X ^ Veselovskaya. Miklós Nádasy.secrets of life. p. Synthesis and Biology. Text is available under the Creative Commons Attribution-ShareAlike License. Second Edition. 2002. pp. p. Volume 56. 136 ^ Geoffrey A. http://www. 168. 172. the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid. Wikipedia® is a registered trademark of the Wikimedia Foundation. 179. E. 171. pp. 309 ^ Dewick. Wiley-VCH. 177. Knunyants IL (1988). 8 ^ Veselovskaya. pp.

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