Alkaloid - Wikipedia, The F...

Alkaloid - Wikipedia, the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.
htm
Alkaloid
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]
Contents
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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Alkaloid - Wikipedia, the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.htm
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 root
Latin: 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 into
wide 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 are

formed by adding the suffix "-ine" to the species or generic alkaloids. For
example, atropine is isolated from the plant Atropa belladonna, strychnine is
obtained from the seed of Strychnine tree.[5] If several alkaloids are extracted
from 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]
The article which
introduced the concept
History of "alkaloid".
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, the

German chemist Friedrich Sertürner isolated from opium a
"soporific principle" (Latin: principium somniferum), which he
called "morphium" in honor of Morpheus, the Greek god of
dreams (the modern name "morphine" was given by the French
physicist Joseph Louis Gay-Lussac). 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). Several other alkaloids were
discovered around that time, including xanthine (1817), atropine
(1819), caffeine (1820), coniine (1827), nicotine (1828),
Friedrich Sertürner, the German chemist
colchicine (1833), sparteine (1851) and cocaine (1860).[20] who first isolated morphine from
opium.
The first complete synthesis of an alkaloid was achieved in 1886
by the German chemist Albert Ladenburg. He produced coniine
by 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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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 are
characterized by a great structural diversity and there is no uniform
classification of alkaloids.[24] Historically, first classification methods
combined alkaloids by the common natural source, e.g., a certain type of
plants. 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., Bufotenin, a poison from
indole, isoquinoline and pyridine-like) or biogenetic precursor (ornithine, some toads, contains an
lysine, tyrosine, tryptophan, etc.).[5] However, they require compromises in indole core and is
produced in living
borderline cases;[24] for example, nicotine contains a pyridine fragment from organisms from the
nicotinamide and pyrrolidine part from ornithine[26] and therefore can be amino acid tryptophan.
assigned to both classes.[27]
Alkaloids are often divided into the following major groups:[28]
1. "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
The nicotine molecule
alkaloids coniine and coniceine[32] although they do not originate from contains both pyridine
amino acids.[33] (left) and pyrrolidine
2. "Protoalkaloids", which contain nitrogen and also originate from amino rings (right).
[29]
acids. Examples include mescaline, adrenaline and ephedrine.
3. Polyamine alkaloids – derivatives of putrescine, spermidine and spermine.
4. Peptide and cyclopeptide alkaloids.[34]
5. 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 as
ephedrine and cathinone. Those originate from the amino acid phenylalanine, but acquire their
nitrogen atom not from the amino acid but through transamination.[37][38]
Some alkaloids do not have the carbon skeleton characteristic of their group. So, galantamine and
homoaporphines 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 Ornithine or arginine →
Hygrine, hygroline,
derivatives[40] putrescine → [40][42]
N-methylputrescine → stachydrine
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N-methyl-∆1-pyrroline
[41]
Tropane
derivatives[43] Atropine group Ornithine or arginine → Atropine, scopolamine,
Substitution in positions 3, 6 or 7 putrescine → hyoscyamine[40][43][44]
N-methylputrescine →
Cocaine group N-methyl-∆1-pyrroline Cocaine, ecgonine
Substitution in positions 2 and 3 [41] [43][45]
Retronecine,
Non-esters heliotridine, laburnine
In plants: ornithine or [46][47]
Complex esters of arginine → putrescine Indicine, lindelophin,
→ homospermidine →
Pyrrolizidine monocarboxylic acids sarracine [46]
retronecine [41]
derivatives[46] Platyphylline,
Macrocyclic diesters
trichodesmine[46]
In fungi: L-proline +
L-homoserine →
Loline, N-formylloline,
1-aminopyrrolizidines (lolines) N-(3-amino- [50]
3-carboxypropyl)proline N-acetylloline
→ norloline[48][49]
Piperidine Lysine → cadaverine Sedamine, lobeline,
derivatives[51] → ∆1-piperideine [52]
anaferine, piperine
[32][53]
Octanoic acid →
coniceine → coniine Coniine, coniceine [33]
[33]
Lupinine group Lupinine, nupharidin

[54]
Cytisine group Cytisine [54]
Quinolizidine
Sparteine, lupanine,
derivatives[54][55] Sparteine group Lysine → cadaverine
anahygrine[54]
→ ∆1-piperideine [56]
Matrine, oxymatrine,
Matrine group
allomatridine[54][57][58]
Ormosanine,
Ormosanine group
piptantine[54][59]
Indolizidine Lysine →
derivatives[60] δ-semialdehyde of
Swainsonine,
α-aminoadipic acid →
pipecolic acid → 1 castanospermine [62]
indolizidinone [61]
Pyridine Nicotinic acid → Trigonelline, ricinine,
Simple derivatives of pyridine
derivatives[63][64] digidronikotinovaya arecoline [63][66]
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Polycyclic noncondensing Nicotine, nornicotine,

pyridine derivatives acid → anabasine, anatabine
[63][66]
1,2-dihydropyridine [65]
Polycyclic condensed pyridine Actinidine, gentianine,
derivatives pediculinine [67]
Sesquiterpene pyridine Nicotinic acid, Evonine, hippocrateine,
derivatives isoleucine [11] triptonine [64][65]
Simple derivatives of Salsoline, lophocerine
isoquinoline [69] [68][69]
Derivatives of 1- and N-methylcoridaldine,

3-isoquinolines [72] noroxyhydrastinine [72]
Derivatives of 1- and
4-phenyltetrahydroisoquinolines Cryptostilin [69][73]
[69]
Derivatives of 5-naftil-
Ancistrocladine [74]
isoquinoline [74]
Derivatives of 1- and 2-benzyl- Papaverine,

laudanosine,
izoquinolines [75] sendaverine
Cularine group[76] Cularine, yagonine [76]
Argemonine, amurensin
Pavines and isopavines [77] [77]
Isoquinoline Benzopyrrocolines [78] Cryptaustoline [69]

derivatives and Tyrosine or Berberine, canadine,
related alkaloids phenylalanine → ophiocarpine,
[68] Protoberberines [69] dopamine or tyramine mecambridine,
(for alkaloids Amarillis) corydaline [79]
[70][71]
Hydrastine, narcotine
Phtalidisoquinolines [69]
(Noscapine) [80]
Spirobenzylisoquinolines [69] Fumaricine [77]
Emetine, protoemetine,
Ipecacuanha alkaloids[81]
ipecoside [81]
Sanguinarine,
[69] oxynitidine,
Benzophenanthridines
corynoloxine [82]
Glaucine, coridine,
Aporphines [69]
liriodenine [83]
Pronuciferine,
Proaporphines [69]
glaziovine [69][78]
Kreysiginine,
Homoaporphines [84]
multifloramine [84]
Homoproaporphines [84] Bulbocodine [76]
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Morphine, codeine,
Morphines[85] thebaine, sinomenine
[86]
Kreysiginine,
Homomorphines [87]
androcymbine [85]
Tropoloisoquinolines [69] Imerubrine [69]
Rufescine, imeluteine
Azofluoranthenes [69] [88]
Lycorine, ambelline,
[89] tazettine, galantamine,
Amaryllis alkaloids
montanine [90]
Erysodine, erythroidine
Erythrite alkaloids[73] [73]
Atherosperminine
Phenanthrene derivatives [69] [69][79]
Protopine,
[69] oxomuramine,
Protopins
corycavidine [82]
Aristolactam [69] Doriflavin [69]
Oxazole
derivatives[91]
Tyrosine → tyramine Annuloline, halfordinol,
[92] texaline, texamine[93]
Isoxazole
derivatives
Ibotenic acid →
Ibotenic acid, Muscimol
Muscimol
Thiazole
derivatives[94] 1-Deoxy-D-xylulose
Nostocyclamide,
5-phosphate (DOXP),
thiostreptone [94][96]
tyrosine, cysteine [95]
3,4-Dihydro-4-quinazolone
Quinazoline derivatives Febrifugine[99]
derivatives[97] Anthranilic acid or
1,4-Dihydro-4-quinazolone Glycorine, arborine,
phenylalanine or
derivatives glycosminine[99]
ornithine [98]
Pyrrolidine and piperidine
quinazoline derivatives Vazicine (peganine) [91]
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Acridine
derivatives[91] Rutacridone,
Anthranilic acid [100]
acronicine[101][102]
Simple derivatives of quinoline Cusparine, echinopsine,

derivatives of 2 - quinolones evocarpine[104]
and 4-quinolone [106][107]
Anthranilic acid →
Tricyclic terpenoids 3-carboxyquinoline Flindersine[104][108]
Quinoline [105]
Dictamnine, fagarine,
derivatives[103][104] Furanoquinoline derivatives
skimmianine[104]
[109][110]
Tryptophan →
tryptamine →
strictosidine (with Quinine quinidine
Quinines secologanin) → cinchonine, cinhonidine
[108]
korinanteal →
cinhoninon [71][105]
Non-isoprene indole alkaloids
Serotonin, psilocybin,
[111] dimethyltryptamine
Simple indole derivatives
(DMT), bufotenin
[113][114]
Simple derivatives of Tryptophan → Harman, harmine,

tryptamine or harmaline, eleagnine
β-carboline [115] [112] [111]
5-hydroxitriptofan
Physostigmine (eserine),
etheramine,
Indole Pyrroloindole alkaloids [116] physovenine,
derivatives[86] eptastigmine[116]
Semiterpenoid indole alkaloids
Tryptophan →
chanoclavine →
agroclavine → Ergotamine, ergobasine,
See also: Ergot alkaloids[86]
indole
elimoclavine → ergosine[117]
paspalic acid → lysergic
alkaloids
acid [116]
Monoterpenoid indole alkaloids
Ajmalicine, sarpagine,
vobasine, ajmaline,
Tryptophan → yohimbine, reserpine,
tryptamine → mitragynine,[118][119]
Corynanthe type alkaloids[112] strictosidine (with group strychnine and
secologanin) [112] (Strychnine brucine,
aquamicine, vomicine
[120]
)
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Ibogamine, ibogaine,
Iboga-type alkaloids[112]
voacangine[112]
Aspidosperma-type Vincamine, vincotine,
alkaloids[112] aspidospermine[121][122]
Imidazole
derivatives[91] Directly from
Histamine, pilocarpine,
pilosine,
histidine[123]
stevensine[91][123]
Purine Xantosine (formed in

derivatives[124] 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 → Tyramine, ephedrine,
β-Phenylethylamine dopamine → adrenaline pseudoephedrine,
derivatives[78] and mescaline tyrosine mescaline, cathinone,
→ tyramine catecholamines
phenylalanine → (adrenaline,
1-phenylpropane- noradrenaline,
1,2-dione → cathinone
dopamine)[11][128]
→ ephedrine and
pseudoephedrine
[11][38][127]
Colchicine alkaloids
[129] Tyrosine or
phenylalanine →
Colchicine,
dopamine →
autumnaline → colchamine[129]
colchicine [130]
Muscarine [131]
Glutamic acid → Muscarine,
3-ketoglutamic acid → allomuscarine,
muscarine (with pyruvic epimuscarine,
acid)[132] epiallomuscarine[131]
Benzylamine[133] Phenylalanine with Capsaicin,

valine, leucine or dihydrocapsaicin,
nordihydrocapsaicin
isoleucine[134] [133][135]
Polyamines alkaloids
Putrescine ornithine → putrescine
derivatives[136] → spermidine → Paucine [136]
spermine[137]
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Spermidine
Lunarine,
derivatives[136]
codonocarpine[136]
Spermine
Verbascenine,
derivatives[136]
aphelandrine [136]
Peptide (cyclopeptide) alkaloids

Peptide alkaloids Numularine C,
Numularine C type
with a numularine S [34]
13-membered cycle Ziziphin A, sativanine H
[34][138] Ziziphin type
[34]
Frangulanine, scutianine
Frangulanine type
J [138]
Scutianine A type Scutianine A [34]
Peptide alkaloids
From different amino Integerrine, discarine D
with a Integerrine type
14-membered cycle acids [34] [138]
[34][138] Amphibine F, spinanine
Amphibine F type
A [34]
Amfibine B type Amphibine B, lotusine C

[34]
Peptide alkaloids
with a Mucronine A type Mucronine A [31][138]
15-membered cycle
[138]
Pseudoalkaloids (terpenes and steroids)
Mevalonic acid →
Diterpenes [31]
izopentenilpyrophosfate
Licoctonine type Aconitine, delphinine
→ geranyl [31][141]
pyrophosphate
[139][140]
Steroids[142]
Cholesterol, Solasodine, solanidine,
arginine[143] veralkamine[144]
Properties
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Most alkaloids contain oxygen; those compounds are usually

colorless 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 poorly
soluble in water but readily dissolve in organic solvents, such as
diethyl ether, chloroform and 1,2-dichloroethane. However, caffeine
dissolves well in boiling water.[147] With acids, alkaloids form salts
of various strengths. Those salts are usually soluble in water and
alcohol and poorly soluble in most organic solvents. Exceptions
include scopolamine hydrobromide which is soluble in organic
solvents and water-soluble quinine sulfate.[146]
Head of a lamb born by a sheep
Most alkaloids have a bitter flavor. It is believed that plants evolved which ate leaves of the corn lily
the ability to produce these bitter substances, many of which are plant. The cyclopia in the calf is
poisonous, in order to protect themselves from animals; however, induced by the alkaloid
cyclopamine present in the plant.
animals in turn evolved the ability to detoxify alkaloids.[148] Some
alkaloids can produce developmental defects in the offspring of
animals 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 grazed
on corn lily suffered serious facial defects. Those defects ranged from deformed jaws to cyclopia (see
picture). 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 is

inhomogeneous over the plant tissues. Depending on the type of
plants, the maximum concentration is observed in the leaves (black
henbane), 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 as

psilocybin 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 and
serotonin, which play an important role in higher animals, are similar Strychnine tree. Its seeds are rich in
strychnine and brucine.
to alkaloids in their structure and biosynthesis and are sometimes
called alkaloids.[156]
Extraction
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Because of the structural diversity of alkaloids, there is no single

method of their extraction from natural raw materials.[157] Most
methods exploit the property of most alkaloids to be soluble in
organic solvents but not in water, and the opposite tendency of their
salts.
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 Crystals of piperine extracted from
present in the raw plants in the form of salts of organic acids.[157] black pepper.
[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, such as 1,2-dichloroethane, chloroform, diethyl ether or benzene. Then, the
impurities are dissolved by weak acids; this converts alkaloid bases into salts which are washed away with
water. If necessary, an aqueous solution of alkaloid salts is again made alkaline and treated with an organic
solvent. 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 in
water, ethanol or methanol). A base is then added to convert alkaloids to basic forms which are extracted
with 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 a
carbanion, 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 and
tetrameric 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., voacamine

Michael 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 assumed
that 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 alkaloid
liriodenine produced by the tulip tree protects it from parasitic mushrooms. In addition, presence of alkaloids
in 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 as
salts 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 for
semi-synthetic psychoactive drugs. For example, ephedrine and pseudoephedrine are used to produce
methcathinone (ephedrine) and methamphetamine.[181]
See also
Amine Natural products
Base (chemistry) Secondary metabolite
Notes
1. ^ In the penultimate sentence of his article [W. Meissner (1819) "Über Pflanzenalkalien: II. Über ein neues
Pflanzenalkali (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 jetzt
bekannten Pflanzenstoffe nicht mit dem Namen Alkalien, sondern Alkaloide zu belegen, da sie doch in manchen
14 of 19 23/11/2010 16:23
Eigenschaften von den Alkalien sehr abweichen, sie würden daher in dem Abschnitt der Pflanzenchemie vor den
Pflanzensäuren ihre Stelle finden." (In general, it seems appropriate to me to impose on the known plant
substances 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
1. ^ 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.
2. ^ 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)
3. ^ R. H. F. Manske. The Alkaloids. Chemistry and Physiology. Volume VIII. - New York: Academic Press,
1965, p. 673
4. ^ Robert Alan Lewis. Lewis' dictionary of toxicology (http://books.google.com/books?id=caTqdbD7j4AC&
pg=PA51) . CRC Press, 1998, p. 51 ISBN 1-56670-223-2
5. ^ a b c d Chemical Encyclopedia: alkaloids (http://www.xumuk.ru/encyklopedia/119.html)
6. ^ Rhoades, David F (1979). "Evolution of Plant Chemical Defense against Herbivores". In Rosenthal, Gerald
A., and Janzen, Daniel H. Herbivores: Their Interaction with Secondary Plant Metabolites. New York:
Academic Press. p. 41. ISBN 0-12-597180-X.
7. ^ a b c Robert A. Meyers Encyclopedia of Physical Science and Technology, Eighteen-Volume Set, Third
Edition. - Alkaloids ISBN 0-12-227411-3
8. ^ Leland J. Cseke Natural Products from Plants (http://books.google.com/books?id=wV2T41nGFc4C&
pg=PA30) Second Edition. - CRC, 2006, p. 30 ISBN 0-8493-2976-0
9. ^ A. William Johnson Invitation to Organic Chemistry (http://books.google.com/books?id=0X4cQus2gz8C&
pg=PA433) , Jones and Bartlett, 1999, p. 433 ISBN 0-7637-0432-6
10. ^ Raj K Bansal A Text Book of Organic Chemistry (http://books.google.com/books?id=1B6ijcTkD5EC&
pg=PA644) . 4th Edition, New Age International, 2004, p. 644 ISBN 81-224-1459-1
11. ^ a b c d Aniszewski, p. 110
12. ^ Biographical information about German pharmacist Carl Friedrich Wilhelm Meißner (1792-1853) is available
in the German Wikipedia: http://de.wikipedia.org/wiki/Carl_Friedrich_Wilhelm_Mei%C3%9Fner (in German).
13. ^ Hesse, pp. 1–3
14. ^ a b Hesse, p. 5
15. ^ Hesse, p. 7
16. ^ a b Aniszewski, p. 182
17. ^ Hesse, p. 338
18. ^ Hesse, p. 304
19. ^ Hesse, p. 350
20. ^ Hesse, pp. 313–316
21. ^ a b TSB: Coniine (http://slovari.yandex.ru/dict/bse/article/00036/77600.htm)
22. ^ Hesse, p. 204
23. ^ Begley Encyclopedia of Chemical Biology: Natural Products in Plants, Chemical Diversity of
24. ^ a b Hesse, p. 11
25. ^ Orekhov, p. 6
26. ^ Aniszewski, p. 109
27. ^ a b Dewick, p. 307
28. ^ Hesse, p. 12
29. ^ a b Plemenkov, p. 223
31. ^ a b c d Hesse, p. 84
32. ^ a b Hesse, p. 31
33. ^ a b c Dewick, p. 381
34. ^ a b c d e f g h i Dimitris C. Gournelif, Gregory G. Laskarisb and Robert Verpoorte (1997). "Cyclopeptide
alkaloids". Nat. Prod. Rep. 14 (1): 75–82. doi:10.1039/NP9971400075 (http://dx.doi.org
15 of 19 23/11/2010 16:23
/10.1039%2FNP9971400075) . PMID 9121730 (http://www.ncbi.nlm.nih.gov/pubmed/9121730) .

36. ^ Plemenkov, p. 246
38. ^ a b Dewick, p. 382
39. ^ Hesse, pp. 44, 53
40. ^ a b c Plemenkov, p. 224
41. ^ a b c Aniszewski, p. 75
42. ^ Orekhov, p. 33
43. ^ a b c Chemical Encyclopedia: Tropan alkaloids (http://www.xumuk.ru/encyklopedia/2/4609.html)
44. ^ Hesse, p. 34
46. ^ a b c d Chemical Encyclopedia: Pyrrolizidine alkaloids (http://www.xumuk.ru/encyklopedia/2/3370.html)
48. ^ Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL (2005). "Biosynthetic
precursors of fungal pyrrolizidines, the loline alkaloids". Chembiochem 6 (6): 1016–1022.
doi:10.1002/cbic.200400327 (http://dx.doi.org/10.1002%2Fcbic.200400327) . PMID 15861432
(http://www.ncbi.nlm.nih.gov/pubmed/15861432) .
49. ^ Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL (2006). "On the
sequence of bond formation in loline alkaloid biosynthesis". Chembiochem 7 (7): 1078–1088.
doi:10.1002/cbic.200600066 (http://dx.doi.org/10.1002%2Fcbic.200600066) . PMID 16755627
50. ^ Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP (2007). "Loline alkaloids: currencies of
mutualism". Phytochemistry 68 (7): 980–996. doi:10.1016/j.phytochem.2007.01.010 (http://dx.doi.org
/10.1016%2Fj.phytochem.2007.01.010) . PMID 17346759 (http://www.ncbi.nlm.nih.gov/pubmed/17346759) .
53. ^ Orekhov, p. 80
54. ^ a b c d e f Chemical Encyclopedia: Quinolizidine alkaloids (http://www.xumuk.ru/encyklopedia/2/5011.html)
55. ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. - London: The Chemical Society, 1971,
p. 93
p. 91
58. ^ Joseph P. Michael (2002). "Indolizidine and quinolizidine alkaloids". Nat. Prod. Rep 19: 458–475.
doi:10.1039/b208137g (http://dx.doi.org/10.1039%2Fb208137g) .
p. 92
60. ^ Dewick, p. 310
64. ^ a b Chemical Encyclopedia: pyridine alkaloids (http://www.xumuk.ru/encyklopedia/2/3336.html)
68. ^ a b Hesse, p. 36
69. ^ 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.xumuk.ru
/encyklopedia/1642.html)
70. ^ Aniszewski, pp. 77–78
71. ^ a b c d Tadhg P. Begley.Encyclopedia of Chemical Biology: Alkaloid Biosynthesis
72. ^ a b J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. - London: The Chemical Society,
1973, p. 122
73. ^ a b c Hesse, p. 54
74. ^ a b Hesse, p. 37
75. ^ Hesse, p. 38
76. ^ a b c Hesse, p. 46
16 of 19 23/11/2010 16:23
77. ^ a b c Hesse, p. 50
78. ^ 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
79. ^ a b Hesse, p. 47
80. ^ Hesse, p. 39
81. ^ a b Hesse, p. 41
82. ^ a b Hesse, p. 49
83. ^ Hesse, p. 44
84. ^ a b c J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. - London: The Chemical Society,
1973, p. 164
85. ^ a b Hesse, p. 51
p. 163
p. 168
89. ^ Hesse, p. 52
90. ^ Hesse, p. 53
91. ^ a b c d e Plemenkov, p. 241
92. ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 35. - Academic Press, 1989, p. 261
93. ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 35. - Academic Press, 1989, pp.
260–263
95. ^ Tadhg P. Begley.Encyclopedia of Chemical Biology: Cofactor Biosynthesis
96. ^ John R. Lewis (2000). "Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and
other 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.
97. ^ Chemical Encyclopedia: Quinazoline alkaloids (http://www.xumuk.ru/encyklopedia/2/5003.html)
100. ^ Richard B. Herbert; Herbert, Richard B.; Herbert, Richard B. (1999). "The biosynthesis of plant alkaloids and
nitrogenous 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.
101. ^ Plemenkov, pp. 231, 246
102. ^ Hesse, p. 58
104. ^ a b c d Chemical Encyclopedia: Quinoline alkaloids (http://www.xumuk.ru/encyklopedia/2/5014.html)
106. ^ Orekhov, p. 205
107. ^ Hesse, p. 55
109. ^ Orekhov, p. 212
112. ^ a b c d e f Aniszewski, p. 113
113. ^ Hesse, p. 15
p. 467
115. ^ Dewick, p. 349-350
116. ^ a b c Aniszewski, p. 119
117. ^ Hesse, p. 29
118. ^ Hesse, pp. 23-26
17 of 19 23/11/2010 16:23
p. 169
p. 210
121. ^ Hesse, pp. 17-18
122. ^ Dewick, p. 357
124. ^ Hesse, p. 72
125. ^ Hesse, p. 73
126. ^ Dewick, p. 396
127. ^ PlantCyc Pathway: ephedrine biosynthesis (http://www.plantcyc.org:1555/PLANT/NEW-IMAGE?type=NIL&
object=PWY-5883)
128. ^ Hesse, p. 76
129. ^ a b Chemical Encyclopedia: colchicine alkaloids (http://www.xumuk.ru/encyklopedia/2069.html)
131. ^ a b Hesse, p. 81
133. ^ a b Hesse, p. 77
136. ^ a b c d e f Hesse, p. 82
137. ^ Spermine Biosynthesis (http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/misc/spermine.html)
138. ^ a b c d e f Plemenkov, p. 243
139. ^ Chemical Encyclopedia: Terpenes (http://www.xumuk.ru/encyklopedia/2/4392.html)
140. ^ Tadhg P. Begley.Encyclopedia of Chemical Biology: Natural Products: An Overview
141. ^ 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.
142. ^ Hesse, p. 88
143. ^ Dewick, p. 388
145. ^ TSB: Nicotine (http://slovari.yandex.ru/dict/bse/article/00052/84600.htm)
146. ^ a b c Grinkevich, p. 131
147. ^ a b G. A. Spiller Caffeine (http://books.google.com/books?id=Rgs_rVOceZwC&pg=PA140) , CRC Press,
1997 ISBN 0-8493-2647-8
148. ^ Fattorusso, p. 53
149. ^ 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.
151. ^ Orekhov, p. 11
152. ^ Hesse, p.4
153. ^ Grinkevich, pp. 122-123
154. ^ Orekhov, p. 12
155. ^ Fattorusso, p. XVII
156. ^ Aniszewski, pp. 110–111
157. ^ a b c d Hesse, p. 116
158. ^ a b Grinkevich, p. 132
159. ^ Grinkevich, p. 5
164. ^ a b Dewick, p. 19
166. ^ Dewick, p. 305
18 of 19 23/11/2010 16:23
167. ^ Hesse, pp. 91–105

169. ^ Hesse, pp. 283-291
170. ^ Aniszewski, pp. 142-143
171. ^ Hesse, p. 303
172. ^ Hesse, pp. 303-309
173. ^ Hesse, p. 309
174. ^ Dewick, p. 335
175. ^ György Matolcsy, Miklós Nádasy, Viktor Andriska Pesticide chemistry (http://books.google.com
/books?id=fPiRSsUOpLEC&pg=PA21) , Elsevier, 2002, pp. 21-22 ISBN 0-444-98903-X
176. ^ Veselovskaya, p. 75
177. ^ Hesse, p. 79
179. ^ Geoffrey A. Cordell The Alkaloids: Chemistry and Biology. Volume 56, Elsevier, 2001, p. 8
181. ^ Veselovskaya, pp. 51-52
Bibliography
Tadeusz Aniszewski (2007). Alkaloids - secrets of life. Amsterdam: Elsevier.
ISBN 978-0-444-52736-3.
Tadhg P. Begley (2009). Encyclopedia of Chemical Biology. Wiley. ISBN 978-0-471-75477-0.
Knunyants IL (1988). Chemical Encyclopedia (http://www.cnshb.ru/AKDiL/0048/base
/RA/140004.shtm) . Soviet Encyclopedia. http://www.cnshb.ru/AKDiL/0048/base/RA/140004.shtm.
Paul M Dewick (2002). Medicinal Natural Products. A Biosynthetic Approach. Second Edition.
Wiley. ISBN 0471496405.
E. Fattorusso and O. Taglialatela-Scafati (2008). Modern Alkaloids: Structure, Isolation, Synthesis
and Biology. Wiley-VCH. ISBN 978-3-527-31521-5.
Grinkevich NI Safronich LN (1983). The chemical analysis of medicinal plants: Proc. allowance for
pharmaceutical universities. M.
Manfred Hesse (2002). Alkaloids: Nature's Curse or Blessing?. Wiley-VCH.
ISBN 978-3-906390-24-6.
Orekhov AP (1955). Chemistry alkaloids (Acad. 2 ed.). M.: USSR.
Plemenkov VV (2001). Introduction to the Chemistry of Natural Compounds. Kazan.
N. B. Veselovskaya, AE Kovalenko Drugs, M.: Triada-X, 2000
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Alkaloid - Wikipedia, the free encyclopedia file:///D:/bahan kuliah/bahan kuliah tingkat 4/fitokimia/Alkaloid.

Alkaloids are a group of naturally occurring chemical

There is no unique method of naming alkaloids.[14] Many individual names are

Studies of alkaloids began in the 19th century. In 1804, the

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

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

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

Class Major groups Main synthesis steps Examples

Lupinine group Lupinine, nupharidin

Polycyclic noncondensing Nicotine, nornicotine,

Derivatives of 1- and N-methylcoridaldine,

Derivatives of 1- and 2-benzyl- Papaverine,

Isoquinoline Benzopyrrocolines [78] Cryptaustoline [69]

Simple derivatives of quinoline Cusparine, echinopsine,

Simple derivatives of Tryptophan → Harman, harmine,

Purine Xantosine (formed in

Benzylamine[133] Phenylalanine with Capsaicin,

Peptide (cyclopeptide) alkaloids

Amfibine B type Amphibine B, lotusine C

Most alkaloids contain oxygen; those compounds are usually

The alkaloids content in plants is usually within a few percent and is

Beside plants, alkaloids are found in certain types of fungi, such as

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

Most plants contain several alkaloids. Their mixture is extracted first

Synthesis of Schiff bases

Main article: Mannich reaction

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

Mannich reaction, resulting in, e.g., voacamine

Voacamine Villalstonine Toxiferine

Dauricine Tubocurarine Carpaine

The biological role

Use as psychoactive drugs

/10.1039%2FNP9971400075) . PMID 9121730 (http://www.ncbi.nlm.nih.gov/pubmed/9121730) .

167. ^ Hesse, pp. 91–105

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