Alkaloid - Wikipedia, The f...

The first individual alkaloid, morphine,was isolated in 1804 from poppy

(Papaver somniferum).[1]

AlkaloidFrom Wikipedia, the free encyclopedia

Alkaloids are a group of naturally occurring chemicalcompounds 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 alkaloidsmay contain sulfur and rarely chlorine, bromine or

phosphorus.[5]

Alkaloids are produced by a large variety of organisms,including bacteria, fungi, plants, and animals and are part of thegroup of natural products (also called secondary metabolites).Many alkaloids can be purified from crude extracts by acid-baseextraction. Many alkaloids are toxic to other organisms. Theyoften have pharmacological effects and are used as medications, as recreational drugs, or in entheogenicrituals. Examples are the local anesthetic and stimulant cocaine, the stimulant caffeine, nicotine, theanalgesic 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]

Contents

1 Naming2 History3 Classification4 Properties5 Distribution in nature6 Extraction7 Biosynthesis

7.1 Synthesis of Schiff bases7.2 Mannich reaction

8 Dimer alkaloids9 The biological role10 Applications

10.1 In medicine10.2 In agriculture10.3 Use as psychoactive drugs

11 See also12 Notes13 References

Alkaloid - Wikipedia, the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.htm

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The article whichintroduced the concept

of "alkaloid".

Friedrich Sertürner, the German chemistwho first isolated morphine from

opium.

14 Bibliography

Naming

The name "alkaloids" (German: Alkaloide) was introduced in 1819 by the

German chemist Carl F.W. Meissner,[12] and is derived from late Latin rootLatin: alkali (which, in turn, comes from the Arabic al qualja - "ashes of

plants") and the suffix Greek: ειδοσ - "like".[nb 1] However, the term came intowide use only after the publication of a review article by O. Jacobsen in the

chemical dictionary of Albert Ladenburg in the 1880s.[13]

There is no unique method of naming alkaloids.[14] Many individual names areformed by adding the suffix "-ine" to the species or generic alkaloids. Forexample, atropine is isolated from the plant Atropa belladonna, strychnine is

obtained from the seed of Strychnine tree.[5] If several alkaloids are extractedfrom one plant then their names often contain suffixes "-idine", "-anine","-aline", "-inine", etc. There are also at least 86 alkaloids containing the root

"vin" (extracted from the Vinca plant).[15]

History

Alkaloid-containing plants were used by humans since ancient times for therapeutic and recreational

purposes. For example, medicinal plants have been known in the Mesopotamia at least around 2000 BC.[16]

The Odyssey of Homer referred to a gift given to Helen by the Egyptian queen, a drug bringing oblivion. It is

believed that the gift was an opium-containing drug.[17] A Chinese book on houseplants written in 1st-3rd

centuries BC mentioned a medical use of Ephedra and opium poppies.[18] Also, coca leaves were used by

South American Indians since ancient times.[19]

Extracts from plants containing toxic alkaloids, such as aconitine and tubocurarine, were used since

antiquity for poisoning arrows.[16]

Studies of alkaloids began in the 19th century. In 1804, theGerman chemist Friedrich Sertürner isolated from opium a"soporific principle" (Latin: principium somniferum), which hecalled "morphium" in honor of Morpheus, the Greek god ofdreams (the modern name "morphine" was given by the Frenchphysicist Joseph Louis Gay-Lussac). A significant contributionto the chemistry of alkaloids in the early years of itsdevelopment was made by the French researchers Pierre JosephPelletier and Joseph Bienaimé Caventou who discovered quinine(1820) and strychnine (1818). Several other alkaloids werediscovered around that time, including xanthine (1817), atropine(1819), caffeine (1820), coniine (1827), nicotine (1828),

colchicine (1833), sparteine (1851) and cocaine (1860).[20]

The first complete synthesis of an alkaloid was achieved in 1886by the German chemist Albert Ladenburg. He produced coniineby reacting 2-methylpyridine with acetaldehyde and reducing the resulting 2-propenyl pyridine with sodium.[21][22] The development of chemistry of alkaloids was accelerated by the emergence of spectroscopical and


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Bufotenin, a poison fromsome toads, contains an

indole core and isproduced in livingorganisms from the

amino acid tryptophan.

The nicotine moleculecontains both pyridine(left) and pyrrolidine

rings (right).

chromatographical methods in the 20th century and by 2008 more than 12,000 alkaloids were identified.[23]

Classification

Compared with most other classes of natural compounds, alkaloids arecharacterized by a great structural diversity and there is no uniform

classification of alkaloids.[24] Historically, first classification methodscombined alkaloids by the common natural source, e.g., a certain type ofplants. This classification was justified by the lack of knowledge about the

chemical structure of alkaloids and is now considered obsolete.[5][25]

More recent classifications are based on similarity of the carbon skeleton (e.g.,indole, isoquinoline and pyridine-like) or biogenetic precursor (ornithine,

lysine, tyrosine, tryptophan, etc.).[5] However, they require compromises in

borderline cases;[24] for example, nicotine contains a pyridine fragment from

nicotinamide and pyrrolidine part from ornithine[26] and therefore can be

assigned to both classes.[27]

Alkaloids are often divided into the following major groups:[28]

"True alkaloids", which contain nitrogen in the heterocycle and originate

from amino acids.[29] Their characteristic examples are atropine,nicotine and morphine. This group also includes some alkaloids which

beside nitrogen heterocycle contain terpene (e.g. evonine[30]) or peptide

fragments (e.g. ergotamine[31]). This group also includes piperidine

alkaloids coniine and coniceine[32] although they do not originate from

amino acids.[33]

1.

"Protoalkaloids", which contain nitrogen and also originate from amino

acids.[29] Examples include mescaline, adrenaline and ephedrine.

2.

Polyamine alkaloids – derivatives of putrescine, spermidine and spermine.3.

Peptide and cyclopeptide alkaloids.[34]4.

Pseudalkaloids – alkaloid-like compounds which do not originate from amino acids.[35] This group

includes, terpene-like and steroid-like alkaloids,[36] as well as purine-like alkaloids such as caffeine,

theobromine and theophylline.[37] Some authors classify as pseudoalkaloids such compounds such asephedrine and cathinone. Those originate from the amino acid phenylalanine, but acquire their

nitrogen atom not from the amino acid but through transamination.[37][38]

5.

Some alkaloids do not have the carbon skeleton characteristic of their group. So, galantamine andhomoaporphines do not contain isoquinoline fragment, but are generally attributed to isoquinoline

alkaloids.[39]

Main classes of monomeric alkaloids are listed in the table below:

Class Major groups Main synthesis steps Examples

Alkaloids with nitrogen heterocycles (true alkaloids)

Pyrrolidine

derivatives[40]Ornithine or arginine →putrescine →N-methylputrescine →

Hygrine, hygroline,

stachydrine[40][42]


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N-methyl-∆1-pyrroline[41]

Tropane

derivatives[43] Atropine groupSubstitution in positions 3, 6 or 7

Ornithine or arginine →putrescine →N-methylputrescine →

N-methyl-∆1-pyrroline[41]

Atropine, scopolamine,

hyoscyamine[40][43][44]

Cocaine groupSubstitution in positions 2 and 3

Cocaine, ecgonine[43][45]

Pyrrolizidine

derivatives[46]

Non-estersIn plants: ornithine orarginine → putrescine→ homospermidine →

retronecine [41]

Retronecine,heliotridine, laburnine[46][47]

Complex esters ofmonocarboxylic acids

Indicine, lindelophin,

sarracine [46]

Macrocyclic diestersPlatyphylline,

trichodesmine[46]

1-aminopyrrolizidines (lolines)

In fungi: L-proline +L-homoserine →N-(3-amino-3-carboxypropyl)proline

→ norloline[48][49]

Loline, N-formylloline,

N-acetylloline[50]

Piperidine

derivatives[51]Lysine → cadaverine

→ ∆1-piperideine [52]

Sedamine, lobeline,anaferine, piperine[32][53]

Octanoic acid →coniceine → coniine[33]

Coniine, coniceine [33]

Quinolizidine

derivatives[54][55]

Lupinine group

Lysine → cadaverine

→ ∆1-piperideine [56]

Lupinine, nupharidin[54]

Cytisine group Cytisine [54]

Sparteine groupSparteine, lupanine,

anahygrine[54]

Matrine groupMatrine, oxymatrine,

allomatridine[54][57][58]

Ormosanine groupOrmosanine,

piptantine[54][59]

Indolizidine

derivatives[60]

Lysine →δ-semialdehyde ofα-aminoadipic acid →pipecolic acid → 1

indolizidinone [61]

Swainsonine,

castanospermine [62]

Pyridine

derivatives[63][64] Simple derivatives of pyridineNicotinic acid →digidronikotinovaya

Trigonelline, ricinine,

arecoline [63][66]


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acid →

1,2-dihydropyridine [65]

Polycyclic noncondensingpyridine derivatives

Nicotine, nornicotine,anabasine, anatabine[63][66]

Polycyclic condensed pyridinederivatives

Actinidine, gentianine,

pediculinine [67]

Sesquiterpene pyridinederivatives

Nicotinic acid,

isoleucine [11]Evonine, hippocrateine,

triptonine [64][65]

Isoquinolinederivatives andrelated alkaloids[68]

Simple derivatives of

isoquinoline [69]

Tyrosine orphenylalanine →dopamine or tyramine(for alkaloids Amarillis)[70][71]

Salsoline, lophocerine[68][69]

Derivatives of 1- and

3-isoquinolines [72]N-methylcoridaldine,

noroxyhydrastinine [72]

Derivatives of 1- and4-phenyltetrahydroisoquinolines[69]

Cryptostilin [69][73]

Derivatives of 5-naftil-

isoquinoline [74] Ancistrocladine [74]

Derivatives of 1- and 2-benzyl-

izoquinolines [75]

Papaverine,laudanosine,sendaverine

Cularine group[76] Cularine, yagonine [76]

Pavines and isopavines [77] Argemonine, amurensin[77]

Benzopyrrocolines [78] Cryptaustoline [69]

Protoberberines [69]

Berberine, canadine,ophiocarpine,mecambridine,

corydaline [79]

Phtalidisoquinolines [69] Hydrastine, narcotine

(Noscapine) [80]

Spirobenzylisoquinolines [69] Fumaricine [77]

Ipecacuanha alkaloids[81] Emetine, protoemetine,

ipecoside [81]

Benzophenanthridines [69]Sanguinarine,oxynitidine,

corynoloxine [82]

Aporphines [69] Glaucine, coridine,

liriodenine [83]

Proaporphines [69] Pronuciferine,

glaziovine [69][78]

Homoaporphines [84] Kreysiginine,

multifloramine [84]

Homoproaporphines [84] Bulbocodine [76]


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Morphines[85]Morphine, codeine,thebaine, sinomenine[86]

Homomorphines [87] Kreysiginine,

androcymbine [85]

Tropoloisoquinolines [69] Imerubrine [69]

Azofluoranthenes [69] Rufescine, imeluteine[88]

Amaryllis alkaloids[89]Lycorine, ambelline,tazettine, galantamine,

montanine [90]

Erythrite alkaloids[73] Erysodine, erythroidine[73]

Phenanthrene derivatives [69] Atherosperminine[69][79]

Protopins [69]Protopine,oxomuramine,

corycavidine [82]

Aristolactam [69] Doriflavin [69]

Oxazole

derivatives[91]

Tyrosine → tyramine[92]

Annuloline, halfordinol,

texaline, texamine[93]

Isoxazolederivatives

Ibotenic acid →Muscimol

Ibotenic acid, Muscimol

Thiazole

derivatives[94]1-Deoxy-D-xylulose5-phosphate (DOXP),

tyrosine, cysteine [95]

Nostocyclamide,

thiostreptone [94][96]

Quinazoline

derivatives[97]

3,4-Dihydro-4-quinazolonederivatives

Anthranilic acid orphenylalanine or

ornithine [98]

Febrifugine[99]

1,4-Dihydro-4-quinazolonederivatives

Glycorine, arborine,

glycosminine[99]

Pyrrolidine and piperidinequinazoline derivatives Vazicine (peganine) [91]


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Acridine

derivatives[91]

Anthranilic acid [100] Rutacridone,

acronicine[101][102]

Quinoline

derivatives[103][104]

Simple derivatives of quinolinederivatives of 2 - quinolonesand 4-quinolone

Anthranilic acid →3-carboxyquinoline[105]

Cusparine, echinopsine,

evocarpine[104]

[106][107]

Tricyclic terpenoids Flindersine[104][108]

Furanoquinoline derivativesDictamnine, fagarine,

skimmianine[104]

[109][110]

Quinines

Tryptophan →tryptamine →strictosidine (withsecologanin) →korinanteal →

cinhoninon [71][105]

Quinine quinidinecinchonine, cinhonidine[108]

Indole

derivatives[86]

See also:

indole

alkaloids

Non-isoprene indole alkaloids

Simple indole derivatives [111]

Tryptophan →tryptamine or

5-hydroxitriptofan [112]

Serotonin, psilocybin,dimethyltryptamine(DMT), bufotenin[113][114]

Simple derivatives of

β-carboline [115]

Harman, harmine,harmaline, eleagnine[111]

Pyrroloindole alkaloids [116]

Physostigmine (eserine),etheramine,physovenine,

eptastigmine[116]

Semiterpenoid indole alkaloids

Ergot alkaloids[86]

Tryptophan →chanoclavine →agroclavine →elimoclavine →paspalic acid → lysergic

acid [116]

Ergotamine, ergobasine,

ergosine[117]

Monoterpenoid indole alkaloids

Corynanthe type alkaloids[112]

Tryptophan →tryptamine →strictosidine (with

secologanin) [112]

Ajmalicine, sarpagine,vobasine, ajmaline,yohimbine, reserpine,

mitragynine,[118][119]

group strychnine and(Strychnine brucine,aquamicine, vomicine[120])


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Iboga-type alkaloids[112] Ibogamine, ibogaine,

voacangine[112]

Aspidosperma-type

alkaloids[112]Vincamine, vincotine,

aspidospermine[121][122]

Imidazole

derivatives[91]Directly from

histidine[123]

Histamine, pilocarpine,pilosine,

stevensine[91][123]

Purine

derivatives[124]Xantosine (formed inpurine biosynthesis) →7 methylxantosine →7-methyl xanthine →theobromine → caffeine[71]

Caffeine theobrominetheophylline saxitoxin[125][126]

Alkaloids with nitrogen in the side chain (protoalkaloids)

β-Phenylethylamine

derivatives[78]

Tyrosine orphenylalanine →dioxyphenilalanine →dopamine → adrenalineand mescaline tyrosine→ tyraminephenylalanine →1-phenylpropane-1,2-dione → cathinone→ ephedrine andpseudoephedrine[11][38][127]

Tyramine, ephedrine,pseudoephedrine,mescaline, cathinone,catecholamines(adrenaline,noradrenaline,

dopamine)[11][128]

Colchicine alkaloids[129] Tyrosine or

phenylalanine →dopamine →autumnaline →

colchicine [130]

Colchicine,

colchamine[129]

Muscarine [131]Glutamic acid →3-ketoglutamic acid →muscarine (with pyruvic

acid)[132]

Muscarine,allomuscarine,epimuscarine,

epiallomuscarine[131]

Benzylamine[133] Phenylalanine withvaline, leucine or

isoleucine[134]

Capsaicin,dihydrocapsaicin,nordihydrocapsaicin[133][135]

Polyamines alkaloids

Putrescine

derivatives[136]ornithine → putrescine→ spermidine →

spermine[137]Paucine [136]


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Spermidine

derivatives[136] Lunarine,

codonocarpine[136]

Spermine

derivatives[136] Verbascenine,

aphelandrine [136]

Peptide (cyclopeptide) alkaloids

Peptide alkaloidswith a13-membered cycle[34][138]

Numularine C type

From different amino

acids [34]

Numularine C,

numularine S [34]

Ziziphin type Ziziphin A, sativanine H[34]

Peptide alkaloidswith a14-membered cycle[34][138]

Frangulanine typeFrangulanine, scutianine

J [138]

Scutianine A type Scutianine A [34]

Integerrine type Integerrine, discarine D[138]

Amphibine F typeAmphibine F, spinanine

A [34]

Amfibine B type Amphibine B, lotusine C[34]

Peptide alkaloidswith a15-membered cycle[138]

Mucronine A type Mucronine A [31][138]

Pseudoalkaloids (terpenes and steroids)

Diterpenes [31]

Licoctonine type

Mevalonic acid →izopentenilpyrophosfate→ geranylpyrophosphate[139][140]

Aconitine, delphinine[31][141]

Steroids[142]

Cholesterol,

arginine[143]Solasodine, solanidine,

veralkamine[144]

Properties


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Head of a lamb born by a sheepwhich ate leaves of the corn lilyplant. The cyclopia in the calf is

induced by the alkaloidcyclopamine present in the plant.

Strychnine tree. Its seeds are rich instrychnine and brucine.

Most alkaloids contain oxygen; those compounds are usuallycolorless crystals at ambient conditions. Oxygen-free alkaloids, such

as nicotine[145] or coniine,[21] are typically volatile, colorless, oily

liquids.[146] Some alkaloids are colored, like berberine (yellow) and

sanguinarine (orange).[146]

Most alkaloid are weak bases, but some are amphoteric, for example

theobromine and theophylline).[147] Most alkaloids are poorlysoluble in water but readily dissolve in organic solvents, such asdiethyl ether, chloroform and 1,2-dichloroethane. However, caffeine

dissolves well in boiling water.[147] With acids, alkaloids form saltsof various strengths. Those salts are usually soluble in water andalcohol and poorly soluble in most organic solvents. Exceptionsinclude scopolamine hydrobromide which is soluble in organic

solvents and water-soluble quinine sulfate.[146]

Most alkaloids have a bitter flavor. It is believed that plants evolvedthe ability to produce these bitter substances, many of which arepoisonous, in order to protect themselves from animals; however,

animals in turn evolved the ability to detoxify alkaloids.[148] Somealkaloids can produce developmental defects in the offspring ofanimals that consume them but cannot detoxify them. A characteristic example is the alkaloid cyclopamine,which is present in the leaves of corn lily. During the 1950s, up to 25% lambs born by sheep that had grazedon corn lily suffered serious facial defects. Those defects ranged from deformed jaws to cyclopia (seepicture). After decades of research, in 1980s, the substance that was responsible for the deformities was

identified as the alkaloid 11-deoxyjervine, which was renamed cyclopamine.[149]

Distribution in nature

Alkaloids are generated by various living organisms, especially by

higher plants – about 10 to 25% of those contain alkaloids.[150][151]

Therefore, in the past the term "alkaloid" was associated with

plants.[152]

The alkaloids content in plants is usually within a few percent and isinhomogeneous over the plant tissues. Depending on the type ofplants, the maximum concentration is observed in the leaves (blackhenbane), fruits or seeds (Strychnine tree), root (Rauwolfia

serpentina) or bark (cinchona).[153] Furthermore, different tissues of

the same plants may contain different alkaloids.[154]

Beside plants, alkaloids are found in certain types of fungi, such aspsilocybin in the fungus of the genus Psilocybe, and in animals, such

as bufotenin in the skin of some toads.[14] Many marine organisms

also contain alkaloids.[155] Some amines, such as adrenaline andserotonin, which play an important role in higher animals, are similarto alkaloids in their structure and biosynthesis and are sometimes

called alkaloids.[156]

Extraction


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Crystals of piperine extracted fromblack pepper.

Because of the structural diversity of alkaloids, there is no single

method of their extraction from natural raw materials.[157] Mostmethods exploit the property of most alkaloids to be soluble inorganic solvents but not in water, and the opposite tendency of theirsalts.

Most plants contain several alkaloids. Their mixture is extracted first

and then individual alkaloids are separated.[158] Plants are

thoroughly ground before extraction.[157][159] Most alkaloids are

present in the raw plants in the form of salts of organic acids.[157]

The extracted alkaloids may remain salts or change into bases.[158]

Base extraction is achieved by processing the raw material with alkaline solutions and extracting the alkaloidbases with organic solvents, such as 1,2-dichloroethane, chloroform, diethyl ether or benzene. Then, theimpurities are dissolved by weak acids; this converts alkaloid bases into salts which are washed away withwater. If necessary, an aqueous solution of alkaloid salts is again made alkaline and treated with an organicsolvent. The process is repeated until the desired purity is achieved.

In the acidic extraction, the raw plant material is processed by a weak acidic solution (e.g., acetic acid inwater, ethanol or methanol). A base is then added to convert alkaloids to basic forms which are extractedwith organic solvent (if the extraction was performed with alcohol, it is removed first, and the remainder is

dissolved in water). The solution is purified as described above.[157][160]

Alkaloids are separated from their mixture using their different solubility in certain solvents and different

reactivity with certain reagents or by distillation.[161]

Biosynthesis

Biological precursors of most alkaloids are amino acids, such as ornithine, lysine, phenylalanine, tyrosine,tryptophan, histidine, aspartic acid and anthranilic acid; all these amino acids, except anthranilic acid, are

proteinogenic, that is they are contained in proteins.[162] Nicotinic acid can be synthesized from tryptophan

or aspartic acid. Ways of alkaloid biosynthesis are too numerous and can not be easily classified.[71]

However, there are a few typical reactions involved in the biosynthesis of various classes of alkaloids,

including synthesis of Schiff bases and Mannich reaction.[162]

Synthesis of Schiff bases

Main article: Schiff base

Schiff bases can be obtained by reacting amines with ketones or aldehydes.[163] These reactions are a

common method of producing C=N bonds.[164]

In the biosynthesis of alkaloids, such reactions may take place within a molecule,[162] such as in the

synthesis of piperidine:[27]


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Mannich reaction

Main article: Mannich reaction

An integral component of the Mannich reaction, in addition to an amine and a carbonyl compound, is acarbanion, which plays the role of the nucleophile in the nucleophilic addition to the ion formed by the

reaction of the amine and the carbonyl.[164]

The Mannich reaction can proceed both intermolecularly and intramolecularly:[165][166]

Dimer alkaloids

In addition to the described above monomeric alkaloids, there are also dimeric, and even trimeric andtetrameric alkaloids formed upon condensation of two, three and four monomeric alkaloids. Dimeric

alkaloids are usually formed from monomers of the same type through the following mechanisms:[167]

Mannich reaction, resulting in, e.g., voacamineMichael reaction (villalstonine).Condensation of aldehydes with amines (toxiferine).Oxidative addition of phenols (dauricine, tubocurarine).Lactonization (carpaine).

Voacamine Villalstonine Toxiferine


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Dauricine Tubocurarine Carpaine

The biological role

The role of alkaloids for living organisms which produce them is still unclear.[168] Initially it was assumedthat the alkaloids are the final products of nitrogen metabolism in plants, and urea in mammals. Later it was

shown that alkaloid concentrations varies over time and this hypothesis was refuted.[7]

Most of the known functions of alkaloids are related to protection. For example, aporphine alkaloidliriodenine produced by the tulip tree protects it from parasitic mushrooms. In addition, presence of alkaloidsin the plant prevents insects and chordate animals from eating it. However, some animals adapted to

alkaloids and even use them in their own metabolism.[169] Such alkaloid-related substances as serotonin,dopamine and histamine are important neurotransmitters in animals. Alkaloids are also known to regulate

plant growth.[170]

Applications

In medicine

Medical use of alkaloid plants has a long history, and thus when the first alkaloids were synthesized in the

19th century, they immediately found application in clinical practice.[171] Many alkaloids are still used in

medicine, usually in the form of salts, including the following:[7][172]:

Alkaloid Action

Ajmaline antiarrhythmic

Atropine, scopolamine, hyoscyamine anticholinergic

Vinblastine, vincristine antitumor

Vincamine vasodilating, antihypertensive

Codeine cough medicine

Cocaine anesthetic

Colchicine remedy for gout

Morphine analgesic

Reserpine antihypertensive

Tubocurarine Muscle relaxant

Physostigmine inhibitor of acetylcholinesterase


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Quinidine antiarrhythmic

Quinine antipyretics, antimalarial

Emetine antiprotozoal agent

Ergot alkaloids sympathomimetic, vasodilator, antihypertensive

Many synthetic and semisynthetic drugs are structural modifications of the alkaloids, which were designed to

enhance or change the primary effect of the drug and reduce unwanted side effects.[173] For example,

naloxone, an opioid receptor antagonist, is a derivative of thebaine which is present in opium.[174]

Thebaine Naloxone

In agriculture

Prior to the development of a wide range of relatively low-toxic synthetic pesticides, some alkaloids, such assalts of nicotine and anabasine, were used as insecticides. Their use was limited by their high toxicity to

humans.[175]

Use as psychoactive drugs

Preparations of plants containing alkaloids and their extracts, and later pure alkaloids have long been used as

psychoactive substances. Cocaine and cathinone are stimulants of the central nervous system.[176][177]

Mescaline and many of indole alkaloids (such as psilocybin, dimethyltryptamine and ibogaine) have

hallucinogenic effect.[178][179] Morphine and codeine are strong narcotic pain killers.[180]

There are alkaloids that do not have strong psychoactive effect themselves, but are precursors forsemi-synthetic psychoactive drugs. For example, ephedrine and pseudoephedrine are used to produce

methcathinone (ephedrine) and methamphetamine.[181]

See also

AmineBase (chemistry)

Natural productsSecondary metabolite

Notes

^ In the penultimate sentence of his article [W. Meissner (1819) "Über Pflanzenalkalien: II. Über ein neuesPflanzenalkali (Alkaloid)" (On plant alkalis: II. On a new plant alkali (alkaloid)), Journal für Chemie und

Physik, vol. 25, pp. 377–381] Meissner wrote "Überhaupt scheint es mir auch angemessen, die bis jetztbekannten Pflanzenstoffe nicht mit dem Namen Alkalien, sondern Alkaloide zu belegen, da sie doch in manchen

1.


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Eigenschaften von den Alkalien sehr abweichen, sie würden daher in dem Abschnitt der Pflanzenchemie vor denPflanzensäuren ihre Stelle finden." (In general, it seems appropriate to me to impose on the known plantsubstances not the name "alkalis" but "alkaloids", since they differ greatly in some properties from the alkalis;among the chapters of plant chemistry, they would therefore find their place before plant acids [since "Alkaloid"would precede "Säure" (acid)].)

References

^ Andreas Luch (2009). Molecular, clinical and environmental toxicology (http://books.google.com/?id=MtOiLVWBn8cC&pg=PA20) . Springer. p. 20. ISBN 3764383356. http://books.google.com/?id=MtOiLVWBn8cC&pg=PA20.

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^ a b IUPAC. Compendium of Chemical Terminology (http://goldbook.iupac.org/A00220.html) , 2nd ed. (The"Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford(1997) ISBN 0-9678550-9-8 doi:10.1351/goldbook (http://dx.doi.org/10.1351%2Fgoldbook)

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^ R. H. F. Manske. The Alkaloids. Chemistry and Physiology. Volume VIII. - New York: Academic Press,1965, p. 673

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^ a b Aniszewski, p. 8566.^ Plemenkov, p. 22867.

^ a b Hesse, p. 3668.

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72.

^ a b c Hesse, p. 5473.

^ a b Hesse, p. 3774.^ Hesse, p. 3875.

^ a b c Hesse, p. 4676.


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^ a b c Hesse, p. 5077.

^ a b c Kenneth W. Bentley (1997). "β-Phenylethylamines and the isoquinoline alkaloids". Nat. Prod. Rep 14(4): 387–411. doi:10.1039/NP9971400387 (http://dx.doi.org/10.1039%2FNP9971400387) . PMID 9281839(http://www.ncbi.nlm.nih.gov/pubmed/9281839) .

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^ a b Hesse, p. 4181.

^ a b Hesse, p. 4982.^ Hesse, p. 4483.

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^ a b Hesse, p. 5185.

^ a b c Plemenkov, p. 23686.^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. - London: The Chemical Society, 1973,p. 163

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^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. - London: The Chemical Society, 1973,p. 168

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^ Hesse, p. 5289.^ Hesse, p. 5390.

^ a b c d e Plemenkov, p. 24191.^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 35. - Academic Press, 1989, p. 26192.^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 35. - Academic Press, 1989, pp.260–263

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^ a b Plemenkov, p. 24294.^ Tadhg P. Begley.Encyclopedia of Chemical Biology: Cofactor Biosynthesis95.^ John R. Lewis (2000). "Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, andother miscellaneous alkaloids" (http://www.rsc.org/publishing/journals/NP/article.asp?doi=a809403i) . Nat.

Prod. Rep 17 (1): 57–84. doi:10.1039/a809403i (http://dx.doi.org/10.1039%2Fa809403i) . PMID 10714899(http://www.ncbi.nlm.nih.gov/pubmed/10714899) . http://www.rsc.org/publishing/journals/NP/article.asp?doi=a809403i.

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^ Chemical Encyclopedia: Quinazoline alkaloids (http://www.xumuk.ru/encyklopedia/2/5003.html)97.^ Aniszewski, p. 10698.

^ a b Aniszewski, p. 10599.^ Richard B. Herbert; Herbert, Richard B.; Herbert, Richard B. (1999). "The biosynthesis of plant alkaloids andnitrogenous microbial metabolites" (http://www.rsc.org/publishing/journals/NP/article.asp?doi=a705734b) . Nat.

Prod. Rep 16: 199–208. doi:10.1039/a705734b (http://dx.doi.org/10.1039%2Fa705734b) . http://www.rsc.org/publishing/journals/NP/article.asp?doi=a705734b.

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^ Plemenkov, pp. 231, 246101.^ Hesse, p. 58102.^ Plemenkov, p. 231103.

^ a b c d Chemical Encyclopedia: Quinoline alkaloids (http://www.xumuk.ru/encyklopedia/2/5014.html)104.

^ a b Aniszewski, p. 114105.^ Orekhov, p. 205106.^ Hesse, p. 55107.

^ a b Plemenkov, p. 232108.^ Orekhov, p. 212109.^ Aniszewski, p. 118110.


^ a b c d e f Aniszewski, p. 113112.^ Hesse, p. 15113.^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. - London: The Chemical Society, 1971,p. 467

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^ Dewick, p. 349-350115.

^ a b c Aniszewski, p. 119116.^ Hesse, p. 29117.^ Hesse, pp. 23-26118.^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. - London: The Chemical Society, 1971,119.


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p. 169^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 5. - London: The Chemical Society, 1975,p. 210

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^ Hesse, pp. 17-18121.^ Dewick, p. 357122.

^ a b Aniszewski, p. 104123.^ Hesse, p. 72124.^ Hesse, p. 73125.^ Dewick, p. 396126.^ PlantCyc Pathway: ephedrine biosynthesis (http://www.plantcyc.org:1555/PLANT/NEW-IMAGE?type=NIL&object=PWY-5883)

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^ Hesse, p. 76128.

^ a b Chemical Encyclopedia: colchicine alkaloids (http://www.xumuk.ru/encyklopedia/2069.html)129.^ Aniszewski, p. 77130.

^ a b Hesse, p. 81131.^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. - Academic Press, 1984, p. 376132.

^ a b Hesse, p. 77133.^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. - Academic Press, 1984, p. 268134.^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. - Academic Press, 1984, p. 231135.

^ a b c d e f Hesse, p. 82136.^ Spermine Biosynthesis (http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/misc/spermine.html)137.

^ a b c d e f Plemenkov, p. 243138.^ Chemical Encyclopedia: Terpenes (http://www.xumuk.ru/encyklopedia/2/4392.html)139.^ Tadhg P. Begley.Encyclopedia of Chemical Biology: Natural Products: An Overview140.^ Atta-ur-Rahman and M. Iqbal Choudhary (1997). "Diterpenoid and steroidal alkaloids" (http://www.rsc.org/publishing/journals/NP/article.asp?doi=NP9971400191) . Nat. Prod. Rep 14 (2): 191–203.doi:10.1039/np9971400191 (http://dx.doi.org/10.1039%2Fnp9971400191) . PMID 9149410(http://www.ncbi.nlm.nih.gov/pubmed/9149410) . http://www.rsc.org/publishing/journals/NP/article.asp?doi=NP9971400191.

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^ Hesse, p. 88142.^ Dewick, p. 388143.^ Plemenkov, p. 247144.^ TSB: Nicotine (http://slovari.yandex.ru/dict/bse/article/00052/84600.htm)145.

^ a b c Grinkevich, p. 131146.

^ a b G. A. Spiller Caffeine (http://books.google.com/books?id=Rgs_rVOceZwC&pg=PA140) , CRC Press,1997 ISBN 0-8493-2647-8

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^ Fattorusso, p. 53148.^ Thomas Acamovic, Colin S. Stewart, T. W. Pennycott (2004). Poisonous plants and related toxins, Volume

2001 (http://books.google.com/?id=nixyqfGIGHcC&pg=PA362) . CABI. p. 362. ISBN 0851996140.http://books.google.com/?id=nixyqfGIGHcC&pg=PA362.

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^ a b c d Hesse, p. 116157.

^ a b Grinkevich, p. 132158.^ Grinkevich, p. 5159.^ Grinkevich, pp. 132-134160.^ Grinkevich, pp. 134-136161.

^ a b c Plemenkov, p. 253162.^ Plemenkov, p. 254163.

^ a b Dewick, p. 19164.^ Plemenkov, p. 255165.^ Dewick, p. 305166.


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and Biology. Wiley-VCH. ISBN 978-3-527-31521-5.Grinkevich NI Safronich LN (1983). The chemical analysis of medicinal plants: Proc. allowance for

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