Chemistry:Alkaloid

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Short description: Class of naturally occurring chemical compounds
The first individual alkaloid, morphine, was isolated in 1804 from the opium poppy (Papaver somniferum).[1]

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral[2] and even weakly acidic properties.[3] Some synthetic compounds of similar structure may also be termed alkaloids.[4] In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.[5]

Alkaloids are produced by a large variety of organisms including bacteria, fungi, plants, and animals.[6] They can be purified from crude extracts of these organisms by acid-base extraction, or solvent extractions followed by silica-gel column chromatography.[7] Alkaloids have a wide range of pharmacological activities including antimalarial (e.g. quinine), antiasthma (e.g. ephedrine), anticancer (e.g. homoharringtonine),[8] cholinomimetic (e.g. galantamine),[9] vasodilatory (e.g. vincamine), antiarrhythmic (e.g. quinidine), analgesic (e.g. morphine),[10] antibacterial (e.g. chelerythrine),[11] and antihyperglycemic activities (e.g. berberine).[12][13] Many have found use in traditional or modern medicine, or as starting points for drug discovery. Other alkaloids possess psychotropic (e.g. psilocin) and stimulant activities (e.g. cocaine, caffeine, nicotine, theobromine),[14] and have been used in entheogenic rituals or as recreational drugs. Alkaloids can be toxic too (e.g. atropine, tubocurarine).[15] Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly evoke a bitter taste.[16]

The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut.[17] 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 classified as amines rather than as alkaloids.[18] Some authors, however, consider alkaloids a special case of amines.[19][20][21]

Naming

The article that introduced the concept of "alkaloid".

The name "alkaloids" (German: Alkaloide) was introduced in 1819 by German chemist Carl Friedrich Wilhelm Meissner, and is derived from late Latin root alkali and the Greek-language suffix -οειδής -('like').[nb 1] However, the term came into wide use only after the publication of a review article, by Oscar Jacobsen in the chemical dictionary of Albert Ladenburg in the 1880s.[22][23]

There is no unique method for naming alkaloids.[24] Many individual names are formed by adding the suffix "ine" to the species or genus name.[25] For example, atropine is isolated from the plant Atropa belladonna; strychnine is obtained from the seed of the Strychnine tree (Strychnos nux-vomica L.).[5] Where several alkaloids are extracted from one plant their names are often distinguished by variations in the suffix: "idine", "anine", "aline", "inine" etc. There are also at least 86 alkaloids whose names contain the root "vin" because they are extracted from vinca plants such as Vinca rosea (Catharanthus roseus);[26] these are called vinca alkaloids.[27][28][29]

History

Friedrich Sertürner, the German chemist who first isolated morphine from opium.

Alkaloid-containing plants have been used by humans since ancient times for therapeutic and recreational purposes. For example, medicinal plants have been known in Mesopotamia from about 2000 BC.[30] 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.[31] A Chinese book on houseplants written in 1st–3rd centuries BC mentioned a medical use of ephedra and opium poppies.[32] Also, coca leaves have been used by Indigenous South Americans since ancient times.[33]

Extracts from plants containing toxic alkaloids, such as aconitine and tubocurarine, were used since antiquity for poisoning arrows.[30]

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", referring to Morpheus, the Greek god of dreams; in German and some other Central-European languages, this is still the name of the drug. The term "morphine", used in English and French, 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), colchicine (1833), sparteine (1851), and cocaine (1860).[34] The development of the chemistry of alkaloids was accelerated by the emergence of spectroscopic and chromatographic methods in the 20th century, so that by 2008 more than 12,000 alkaloids had been identified.[35]

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.[36][37]

Bufotenin, an alkaloid from some toads, contains an indole core, and is produced in living organisms from the amino acid tryptophan.

Classifications

The nicotine molecule contains both pyridine (left) and pyrrolidine rings (right).

Compared with most other classes of natural compounds, alkaloids are characterized by a great structural diversity. There is no uniform classification.[38] Initially, when knowledge of chemical structures was lacking, botanical classification of the source plants was relied on. This classification is now considered obsolete.[5][39]

More recent classifications are based on similarity of the carbon skeleton (e.g., indole-, isoquinoline-, and pyridine-like) or biochemical precursor (ornithine, lysine, tyrosine, tryptophan, etc.).[5] However, they require compromises in borderline cases;[38] for example, nicotine contains a pyridine fragment from nicotinamide and a pyrrolidine part from ornithine[40] and therefore can be assigned to both classes.[41]

Alkaloids are often divided into the following major groups:[42]

  1. "True alkaloids" contain nitrogen in the heterocycle and originate from amino acids.[43] Their characteristic examples are atropine, nicotine, and morphine. This group also includes some alkaloids that besides the nitrogen heterocycle contain terpene (e.g., evonine[44]) or peptide fragments (e.g. ergotamine[45]). The piperidine alkaloids coniine and coniceine may be regarded as true alkaloids (rather than pseudoalkaloids: see below)[46] although they do not originate from amino acids.[47]
  2. "Protoalkaloids", which contain nitrogen (but not the nitrogen heterocycle) and also originate from amino acids.[43] Examples include mescaline, adrenaline and ephedrine.
  3. Polyamine alkaloids – derivatives of putrescine, spermidine, and spermine.
  4. Peptide and cyclopeptide alkaloids.[48]
  5. Pseudoalkaloids – alkaloid-like compounds that do not originate from amino acids.[49] This group includes terpene-like and steroid-like alkaloids,[50] as well as purine-like alkaloids such as caffeine, theobromine, theacrine and theophylline.[51] Some authors classify ephedrine and cathinone as pseudoalkaloids. Those originate from the amino acid phenylalanine, but acquire their nitrogen atom not from the amino acid but through transamination.[51][52]

Some alkaloids do not have the carbon skeleton characteristic of their group. So, galanthamine and homoaporphines do not contain isoquinoline fragment, but are, in general, attributed to isoquinoline alkaloids.[53]

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[54]
Pyrrolidine structure.svg
 Ornithine or arginine → putrescine → N-methylputrescine → N-methyl-Δ1-pyrroline [55] Cuscohygrine, hygrine, hygroline, stachydrine[54][56]
Tropane derivatives[57]
Tropane numbered.svg
 Atropine group
Substitution in positions 3, 6 or 7 		Ornithine or arginine → putrescine → N-methylputrescine → N-methyl-Δ1-pyrroline [55] Atropine, scopolamine, hyoscyamine[54][57][58]
Cocaine group
Substitution in positions 2 and 3 		Cocaine, ecgonine[57][59]
Pyrrolizidine derivatives[60]
Pyrrolizidine.svg
 Non-esters In plants: ornithine or arginine → putrescine → homospermidine → retronecine[55] Retronecine, heliotridine, laburnine [60][61]
Complex esters of monocarboxylic acids Indicine, lindelophin, sarracine [60]
Macrocyclic diesters Platyphylline, trichodesmine[60]
1-aminopyrrolizidines (lolines) In fungi: L-proline + L-homoserine → N-(3-amino-3-carboxypropyl)proline → norloline[62][63] Loline, N-formylloline, N-acetylloline[64]
Piperidine derivatives[65]
Piperidin.svg
 Lysine → cadaverine → Δ1-piperideine [66] Sedamine, lobeline, anaferine, piperine[46][67]
Octanoic acid → coniceine → coniine[47] Coniine, coniceine [47]
Quinolizidine derivatives[68][69]
Quinolizidine.svg
 Lupinine group Lysine → cadaverine → Δ1-piperideine [70] Lupinine, nupharidin [68]
Cytisine group Cytisine[68]
Sparteine group Sparteine, lupanine, anahygrine[68]
Matrine group. Matrine, oxymatrine, allomatridine[68][71][72]
Ormosanine group Ormosanine, piptantine[68][73]
Indolizidine derivatives[74]
Indolizidine.svg
 Lysine → δ-semialdehyde of α-aminoadipic acid → pipecolic acid → 1 indolizidinone [75] Swainsonine, castanospermine[76]
Pyridine derivatives[77][78]
Pyridine.svg
 Simple derivatives of pyridine Nicotinic acid → dihydronicotinic acid → 1,2-dihydropyridine [79] Trigonelline, ricinine, arecoline[77][80]
Polycyclic noncondensing pyridine derivatives Nicotine, nornicotine, anabasine, anatabine [77][80]
Polycyclic condensed pyridine derivatives Actinidine, gentianine, pediculinine [81]
Sesquiterpene pyridine derivatives Nicotinic acid, isoleucine[21] Evonine, hippocrateine, triptonine [78][79]
Isoquinoline derivatives and related alkaloids [82]
Isoquinoline numbered.svg
 Simple derivatives of isoquinoline [83] Tyrosine or phenylalanine → dopamine or tyramine (for alkaloids Amarillis) [84][85] Salsoline, lophocerine [82][83]
Derivatives of 1- and 3-isoquinolines [86] N-methylcoridaldine, noroxyhydrastinine [86]
Derivatives of 1- and 4-phenyltetrahydroisoquinolines [83] Cryptostilin [83][87]
Derivatives of 5-naftil-isoquinoline [88] Ancistrocladine [88]
Derivatives of 1- and 2-benzyl-izoquinolines [89] Papaverine, laudanosine, sendaverine
Cularine group[90] Cularine, yagonine [90]
Pavines and isopavines [91] Argemonine, amurensine[91]
Benzopyrrocolines [92] Cryptaustoline [83]
Protoberberines [83] Berberine, canadine, ophiocarpine, mecambridine, corydaline [93]
Phthalidisoquinolines [83] Hydrastine, narcotine (Noscapine) [94]
Spirobenzylisoquinolines [83] Fumaricine [91]
Ipecacuanha alkaloids[95] Emetine, protoemetine, ipecoside [95]
Benzophenanthridines [83] Sanguinarine, oxynitidine, corynoloxine [96]
Aporphines [83] Glaucine, coridine, liriodenine [97]
Proaporphines [83] Pronuciferine, glaziovine [83][92]
Homoaporphines [98] Kreysiginine, multifloramine [98]
Homoproaporphines [98] Bulbocodine [90]
Morphines[99] Morphine, codeine, thebaine, sinomenine[100]
Homomorphines [101] Kreysiginine, androcymbine [99]
Tropoloisoquinolines [83] Imerubrine [83]
Azofluoranthenes [83] Rufescine, imeluteine [102]
Amaryllis alkaloids[103] Lycorine, ambelline, tazettine, galantamine, montanine [104]
Erythrina alkaloids[87] Erysodine, erythroidine [87]
Phenanthrene derivatives [83] Atherosperminine [83][93]
Protopines [83] Protopine, oxomuramine, corycavidine [96]
Aristolactam [83] Doriflavin [83]
Oxazole derivatives[105]
Oxazole structure.svg
 Tyrosine → tyramine[106] Annuloline, halfordinol, texaline, texamine[107]
Isoxazole derivatives
Isoxazole structure.png
 Ibotenic acid → Muscimol Ibotenic acid, Muscimol
Thiazole derivatives[108]
Thiazole structure.svg
 1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine[109] Nostocyclamide, thiostreptone [108][110]
Quinazoline derivatives[111]
Quinazoline numbered.svg
 3,4-Dihydro-4-quinazolone derivatives Anthranilic acid or phenylalanine or ornithine[112] Febrifugine[113]
1,4-Dihydro-4-quinazolone derivatives Glycorine, arborine, glycosminine[113]
Pyrrolidine and piperidine quinazoline derivatives Vazicine (peganine) [105]
Acridine derivatives[105]
Acridine.svg
 Anthranilic acid[114] Rutacridone, acronicine[115][116]
Quinoline derivatives[117][118]
Quinoline numbered.svg
 Simple derivatives of quinoline derivatives of 2–quinolones and 4-quinolone Anthranilic acid → 3-carboxyquinoline [119] Cusparine, echinopsine, evocarpine[118][120][121]
Tricyclic terpenoids Flindersine[118][122]
Furanoquinoline derivatives Dictamnine, fagarine, skimmianine[118][123][124]
Quinines Tryptophan → tryptamine → strictosidine (with secologanin) → korinanteal → cinhoninon[85][119] Quinine, quinidine, cinchonine, cinhonidine [122]
Indole derivatives[100]
Indole numbered.svg
 Non-isoprene indole alkaloids
Simple indole derivatives [125] Tryptophan → tryptamine or 5-Hydroxytryptophan[126] Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin[127][128]
Simple derivatives of β-carboline[129] Harman, harmine, harmaline, eleagnine [125]
Pyrroloindole alkaloids [130] Physostigmine (eserine), etheramine, physovenine, eptastigmine[130]
Semiterpenoid indole alkaloids
Ergot alkaloids[100] Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acid → lysergic acid[130] Ergotamine, ergobasine, ergosine[131]
Monoterpenoid indole alkaloids
Corynanthe type alkaloids[126] Tryptophan → tryptamine → strictosidine (with secologanin) [126] Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, mitragynine,[132][133] group strychnine and (Strychnine brucine, aquamicine, vomicine[134])
Iboga-type alkaloids[126] Ibogamine, ibogaine, voacangine[126]
Aspidosperma-type alkaloids[126] Vincamine, vinca alkaloids,[27][135] vincotine, aspidospermine[136][137]
Imidazole derivatives[105]
Imidazole structure.svg
 Directly from histidine[138] Histamine, pilocarpine, pilosine, stevensine[105][138]
Purine derivatives[139]
9H-Purine.svg
 Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methylxanthine → theobromine → caffeine[85] Caffeine, theobromine, theophylline, saxitoxin[140][141]
Alkaloids with nitrogen in the side chain (protoalkaloids)
β-Phenylethylamine derivatives[92]
Phenylethylamine numbered.svg
 Tyrosine or phenylalanine → dioxyphenilalanine → dopamine → adrenaline and mescaline tyrosine → tyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone → ephedrine and pseudoephedrine[21][52][142] Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[21][143]
Colchicine alkaloids [144]
Colchicine.svg
 Tyrosine or phenylalanine → dopamine → autumnaline → colchicine[145] Colchicine, colchamine[144]
Muscarine[146]
Muscarine.svg
 Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[147] Muscarine, allomuscarine, epimuscarine, epiallomuscarine[146]
Benzylamine[148]
Benzylamine.svg
 Phenylalanine with valine, leucine or isoleucine[149] Capsaicin, dihydrocapsaicin, nordihydrocapsaicin, vanillylamine[148][150]
Polyamines alkaloids
Putrescine derivatives[151]
Putrescine.svg
 ornithine → putrescine → spermidine → spermine[152] Paucine [151]
Spermidine derivatives[151]
Spermidine.svg
 Lunarine, codonocarpine[151]
Spermine derivatives[151]
Spermine.svg
 Verbascenine, aphelandrine [151]
Peptide (cyclopeptide) alkaloids
Peptide alkaloids with a 13-membered cycle [48][153] Nummularine C type From different amino acids [48] Nummularine C, Nummularine S [48]
Ziziphine type Ziziphine A, sativanine H [48]
Peptide alkaloids with a 14-membered cycle [48][153] Frangulanine type Frangulanine, scutianine J [153]
Scutianine A type Scutianine A [48]
Integerrine type Integerrine, discarine D [153]
Amphibine F type Amphibine F, spinanine A [48]
Amfibine B type Amphibine B, lotusine C [48]
Peptide alkaloids with a 15-membered cycle [153] Mucronine A type Mucronine A [45][153]
Pseudoalkaloids (terpenes and steroids)
Diterpenes [45]
Isoprene.svg
 Lycoctonine type Mevalonic acid → Isopentenyl pyrophosphate → geranyl pyrophosphate[154][155] Aconitine, delphinine[45][156]
Steroidal alkaloids [157]
Cyclopentenophenanthrene.svg
 Cholesterol, arginine[158] Solanidine, cyclopamine, batrachotoxin[159]

Properties

Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions. Oxygen-free alkaloids, such as nicotine[160] or coniine,[36] are typically volatile, colorless, oily liquids.[161] Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).[161]

Most alkaloids are weak bases, but some, such as theobromine and theophylline, are amphoteric.[162] Many alkaloids dissolve poorly in water but readily dissolve in organic solvents, such as diethyl ether, chloroform or 1,2-dichloroethane. Caffeine,[163] cocaine,[164] codeine[165] and nicotine[166] are slightly soluble in water (with a solubility of ≥1g/L), whereas others, including morphine[167] and yohimbine[168] are very slightly water-soluble (0.1–1 g/L). Alkaloids and acids form salts of various strengths. These salts are usually freely soluble in water and ethanol and poorly soluble in most organic solvents. Exceptions include scopolamine hydrobromide, which is soluble in organic solvents, and the water-soluble quinine sulfate.[161]

Most alkaloids have a bitter taste or are poisonous when ingested. Alkaloid production in plants appeared to have evolved in response to feeding by herbivorous animals; however, some animals have evolved the ability to detoxify alkaloids.[169] Some alkaloids can produce developmental defects in the offspring of animals that consume but cannot detoxify the alkaloids. One example is the alkaloid cyclopamine, produced in the leaves of corn lily. During the 1950s, up to 25% of lambs born by sheep that had grazed on corn lily had serious facial deformations. These ranged from deformed jaws to cyclopia (see picture). After decades of research, in the 1980s, the compound responsible for these deformities was identified as the alkaloid 11-deoxyjervine, later renamed to cyclopamine.[170]

Distribution in nature

Strychnine tree. Its seeds are rich in strychnine and brucine.

Alkaloids are generated by various living organisms, especially by higher plants – about 10 to 25% of those contain alkaloids.[171][172] Therefore, in the past the term "alkaloid" was associated with plants.[173]

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 (for example, black henbane), fruits or seeds (Strychnine tree), root (Rauvolfia serpentina) or bark (cinchona).[174] Furthermore, different tissues of the same plants may contain different alkaloids.[175]

Beside plants, alkaloids are found in certain types of fungus, such as psilocybin in the fruiting bodies of the genus Psilocybe, and in animals, such as bufotenin in the skin of some toads [24] and a number of insects, markedly ants.[176] Many marine organisms also contain alkaloids.[177] Some amines, such as adrenaline and serotonin, which play an important role in higher animals, are similar to alkaloids in their structure and biosynthesis and are sometimes called alkaloids.[178]

Extraction

Crystals of piperine extracted from black pepper.

Because of the structural diversity of alkaloids, there is no single method of their extraction from natural raw materials.[179] Most methods exploit the property of most alkaloids to be soluble in organic solvents[7] 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.[180] Plants are thoroughly ground before extraction.[179][181] Most alkaloids are present in the raw plants in the form of salts of organic acids.[179] The extracted alkaloids may remain salts or change into bases.[180] 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 that 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 that 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.[179][182]

Alkaloids are separated from their mixture using their different solubility in certain solvents and different reactivity with certain reagents or by distillation.[183]

A number of alkaloids are identified from insects, among which the fire ant venom alkaloids known as solenopsins have received greater attention from researchers.[184] These insect alkaloids can be efficiently extracted by solvent immersion of live fire ants[7] or by centrifugation of live ants[185] followed by silica-gel chromatography purification.[186] Tracking and dosing the extracted solenopsin ant alkaloids has been described as possible based on their absorbance peak around 232 nanometers.[187]

Biosynthesis

Biological precursors of most alkaloids are amino acids, such as ornithine, lysine, phenylalanine, tyrosine, tryptophan, histidine, aspartic acid, and anthranilic acid.[188] Nicotinic acid can be synthesized from tryptophan or aspartic acid. Ways of alkaloid biosynthesis are too numerous and cannot be easily classified.[85] However, there are a few typical reactions involved in the biosynthesis of various classes of alkaloids, including synthesis of Schiff bases and Mannich reaction.[188]

Synthesis of Schiff bases

Main page: Chemistry:Schiff base

Schiff bases can be obtained by reacting amines with ketones or aldehydes.[189] These reactions are a common method of producing C=N bonds.[190]

Schiff base formation.svg

In the biosynthesis of alkaloids, such reactions may take place within a molecule,[188] such as in the synthesis of piperidine:[41]

Schiff base formation intramolecular.svg

Mannich reaction

Main page: Chemistry: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.[190]

Mannich.png

The Mannich reaction can proceed both intermolecularly and intramolecularly:[191][192]

Mannich reaction intramolecular.svg

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:[193]

There are also dimeric alkaloids formed from two distinct monomers, such as the vinca alkaloids vinblastine and vincristine,[27][135] which are formed from the coupling of catharanthine and vindoline.[194][195] The newer semi-synthetic chemotherapeutic agent vinorelbine is used in the treatment of non-small-cell lung cancer.[135][196] It is another derivative dimer of vindoline and catharanthine and is synthesised from anhydrovinblastine,[197] starting either from leurosine[198][199] or the monomers themselves.[135][195]

Vinorelbine from leurosine and from catharanthine plus vindoline.jpg

Biological role

Alkaloids are among the most important and best-known secondary metabolites, i.e. biogenic substances not directly involved in the normal growth, development, or reproduction of the organism. Instead, they generally mediate ecological interactions, which may produce a selective advantage for the organism by increasing its survivability or fecundity. In some cases their function, if any, remains unclear.[200] An early hypothesis, that alkaloids are the final products of nitrogen metabolism in plants, as urea and uric acid are in mammals, was refuted by the finding that their concentration fluctuates rather than steadily increasing.[17]

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, the presence of alkaloids in the plant prevents insects and chordate animals from eating it. However, some animals are adapted to alkaloids and even use them in their own metabolism.[201] Such alkaloid-related substances as serotonin, dopamine and histamine are important neurotransmitters in animals. Alkaloids are also known to regulate plant growth.[202] One example of an organism that uses alkaloids for protection is the Utetheisa ornatrix, more commonly known as the ornate moth. Pyrrolizidine alkaloids render these larvae and adult moths unpalatable to many of their natural enemies like coccinelid beetles, green lacewings, insectivorous hemiptera and insectivorous bats.[203] Another example of alkaloids being utilized occurs in the poison hemlock moth (Agonopterix alstroemeriana). This moth feeds on its highly toxic and alkaloid-rich host plant poison hemlock (Conium maculatum) during its larval stage. A. alstroemeriana may benefit twofold from the toxicity of the naturally-occurring alkaloids, both through the unpalatability of the species to predators and through the ability of A. alstroemeriana to recognize Conium maculatum as the correct location for oviposition.[204] A fire ant venom alkaloid known as solenopsin has been demonstrated to protect queens of invasive fire ants during the foundation of new nests, thus playing a central role in the spread of this pest ant species around the world.[205]

Applications

In medicine

Medical use of alkaloid-containing plants has a long history, and, thus, when the first alkaloids were isolated in the 19th century, they immediately found application in clinical practice.[206] Many alkaloids are still used in medicine, usually in the form of salts widely used including the following:[17][207]

Alkaloid Action
Ajmaline Antiarrhythmic
Emetine Antiprotozoal agent, emesis
Ergot alkaloids Vasoconstriction, hallucinogenic, Uterotonic
Glaucine Antitussive
Morphine Analgesic
Nicotine Stimulant, nicotinic acetylcholine receptor agonist
Physostigmine Inhibitor of acetylcholinesterase
Quinidine Antiarrhythmic
Quinine Antipyretic, antimalarial
Reserpine Antihypertensive
Tubocurarine Muscle relaxant
Vinblastine, vincristine Antitumor
Vincamine Vasodilating, antihypertensive
Yohimbine Stimulant, aphrodisiac
Berberine Antihyperglycaemic[13]

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.[208] For example, naloxone, an opioid receptor antagonist, is a derivative of thebaine that is present in opium.[209]

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.[210]

Use as psychoactive drugs

Preparations of plants containing alkaloids and their extracts, and later pure alkaloids, have long been used as psychoactive substances. Cocaine, caffeine, and cathinone are stimulants of the central nervous system.[211][212] Mescaline and many indole alkaloids (such as psilocybin, dimethyltryptamine and ibogaine) have hallucinogenic effect.[213][214] Morphine and codeine are strong narcotic pain killers.[215]

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 and methamphetamine.[216] Thebaine is used in the synthesis of many painkillers such as oxycodone.

See also


Explanatory notes

  1. ↑ Meissner, W. (1819). "Über Pflanzenalkalien: II. Über ein neues Pflanzenalkali (Alkaloid)". Journal für Chemie und Physik 25: 379–381. https://babel.hathitrust.org/cgi/pt?id=nyp.33433069069056;view=1up;seq=415. "In the penultimate sentence of his article, 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 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 currently 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) but follow 'Alkalien')".]". 

Citations

  1. ↑ Luch, Andreas (2009). Molecular, Clinical and Environmental Toxicology, Volume 1: Molecular Toxicology. 1. Springer. p. 20. ISBN 9783764383367. OCLC 1056390214. https://books.google.com/books?id=MtOiLVWBn8cC&pg=PA20. 
  2. ↑ 2.0 2.1 IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "alkaloids". doi:10.1351/goldbook.A00220
  3. ↑ Manske, R. H. F. (2014-05-12). The Alkaloids: Chemistry and Physiology, Volume 8. 8. Saint Louis: Elsevier. pp. 683–695. ISBN 9781483222004. OCLC 1090491824. https://books.google.com/books?id=WPbJCgAAQBAJ. 
  4. ↑ Lewis, Robert Alan (1998-03-23). Lewis' Dictionary of Toxicology. CRC Press. p. 51. ISBN 9781566702232. OCLC 1026521889. https://books.google.com/books?id=caTqdbD7j4AC. 
  5. ↑ 5.0 5.1 5.2 5.3 "АЛКАЛОИДЫ - Химическая энциклопедия". https://www.xumuk.ru/encyklopedia/119.html. 
  6. ↑ Roberts, M. F. (Margaret F.); Wink, Michael (1998). Alkaloids: Biochemistry, Ecology, and Medicinal Applications. Boston: Springer US. ISBN 9781475729054. OCLC 851770197. 
  7. ↑ 7.0 7.1 7.2 Gonçalves Paterson Fox, Eduardo; Russ Solis, Daniel; Delazari dos Santos, Lucilene; Aparecido dos Santos Pinto, Jose Roberto; Ribeiro da Silva Menegasso, Anally; Cardoso Maciel Costa Silva, Rafael; Sergio Palma, Mario; Correa Bueno, Odair et al. (April 2013). "A simple, rapid method for the extraction of whole fire ant venom (Insecta: Formicidae: Solenopsis)". Toxicon 65: 5–8. doi:10.1016/j.toxicon.2012.12.009. PMID 23333648. 
  8. ↑ "Alkaloids as important scaffolds in therapeutic drugs for the treatments of cancer, tuberculosis, and smoking cessation". Curr Top Med Chem 14 (2): 239–252. 2014. doi:10.2174/1568026613666131216105049. PMID 24359196. https://zenodo.org/record/895681. 
  9. ↑ "Multitarget drugs of plants origin acting on Alzheimer's disease". Curr Med Chem 20 (13): 1686–93. 2013. doi:10.2174/0929867311320130008. PMID 23410167. 
  10. ↑ Raymond S. Sinatra; Jonathan S. Jahr; J. Michael Watkins-Pitchford (2010). The Essence of Analgesia and Analgesics. Cambridge University Press. pp. 82–90. ISBN 978-1139491983. 
  11. ↑ "Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities". Int J Antimicrob Agents 44 (5): 377–386. 2014. doi:10.1016/j.ijantimicag.2014.06.001. PMID 25130096. https://zenodo.org/record/1004771. 
  12. ↑ Singh, Sukhpal; Bansal, Abhishek; Singh, Vikramjeet; Chopra, Tanya; Poddar, Jit (June 2022). "Flavonoids, alkaloids and terpenoids: a new hope for the treatment of diabetes mellitus" (in en). Journal of Diabetes & Metabolic Disorders 21 (1): 941–950. doi:10.1007/s40200-021-00943-8. ISSN 2251-6581. PMID 35673446. 
  13. ↑ 13.0 13.1 Behl, Tapan; Gupta, Amit; Albratty, Mohammed; Najmi, Asim; Meraya, Abdulkarim M.; Alhazmi, Hassan A.; Anwer, Md. Khalid; Bhatia, Saurabh et al. (2022-09-09). "Alkaloidal Phytoconstituents for Diabetes Management: Exploring the Unrevealed Potential" (in en). Molecules 27 (18): 5851. doi:10.3390/molecules27185851. ISSN 1420-3049. PMID 36144587. 
  14. ↑ "Alkaloid". 2007-12-18. http://science.howstuffworks.com/alkaloid-info.htm. 
  15. ↑ "Chapter 9: Alkaloids". Pharmacognosy and Pharmacobiotechnology. Philadelphia: Lippincott, Williams & Wilkins. 1996. pp. 143–185. ISBN 978-0683085006. 
  16. ↑ Rhoades, David F (1979). "Evolution of Plant Chemical Defense against Herbivores". Herbivores: Their Interaction with Secondary Plant Metabolites. New York: Academic Press. p. 41. ISBN 978-0-12-597180-5. 
  17. ↑ 17.0 17.1 17.2 Robert A. Meyers Encyclopedia of Physical Science and Technology – Alkaloids, 3rd edition. ISBN:0-12-227411-3
  18. ↑ Leland J. Cseke Natural Products from Plants Second Edition. CRC, 2006, p. 30 ISBN:0-8493-2976-0
  19. ↑ A. William Johnson Invitation to Organic Chemistry, Jones and Bartlett, 1999, p. 433 ISBN:0-7637-0432-6
  20. ↑ Raj K Bansal A Text Book of Organic Chemistry. 4th Edition, New Age International, 2004, p. 644 ISBN:81-224-1459-1
  21. ↑ 21.0 21.1 21.2 21.3 Aniszewski, p. 110
  22. ↑ Hesse, pp. 1–3
  23. ↑ Oscar Jacobsen, "Alkaloide" in: Ladenburg, Handwörterbuch der Chemie (Breslau, Germany: Eduard Trewendt, 1882), vol. 1, pp. 213–422.
  24. ↑ 24.0 24.1 Hesse, p. 5
  25. ↑ The suffix "ine" is a Greek feminine patronymic suffix and means "daughter of"; hence, for example, "atropine" means "daughter of Atropa" (belladonna): Development of Systematic Names for the Simple Alkanes . yale.edu
  26. ↑ Hesse, p. 7
  27. ↑ 27.0 27.1 27.2 van der Heijden, Robert; Jacobs, Denise I.; Snoeijer, Wim; Hallard, Didier; Verpoorte, Robert (2004). "The Catharanthus alkaloids: Pharmacognosy and biotechnology". Current Medicinal Chemistry 11 (5): 607–628. doi:10.2174/0929867043455846. PMID 15032608. 
  28. ↑ Cooper, Raymond; Deakin, Jeffrey John (2016). "Africa's gift to the world". Botanical Miracles: Chemistry of Plants That Changed the World. CRC Press. pp. 46–51. ISBN 9781498704304. https://books.google.com/books?id=aXGmCwAAQBAJ&pg=PA46. 
  29. ↑ Raviña, Enrique (2011). "Vinca alkaloids". The evolution of drug discovery: From traditional medicines to modern drugs. John Wiley & Sons. pp. 157–159. ISBN 9783527326693. https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA157. 
  30. ↑ 30.0 30.1 Aniszewski, p. 182
  31. ↑ Hesse, p. 338
  32. ↑ Hesse, p. 304
  33. ↑ Hesse, p. 350
  34. ↑ Hesse, pp. 313–316
  35. ↑ Begley, Natural Products in Plants.
  36. ↑ 36.0 36.1 Template:GSEn
  37. ↑ Hesse, p. 204
  38. ↑ 38.0 38.1 Hesse, p. 11
  39. ↑ Orekhov, p. 6
  40. ↑ Aniszewski, p. 109
  41. ↑ 41.0 41.1 Dewick, p. 307
  42. ↑ Hesse, p. 12
  43. ↑ 43.0 43.1 Plemenkov, p. 223
  44. ↑ Aniszewski, p. 108
  45. ↑ 45.0 45.1 45.2 45.3 Hesse, p. 84
  46. ↑ 46.0 46.1 Hesse, p. 31
  47. ↑ 47.0 47.1 47.2 Dewick, p. 381
  48. ↑ 48.0 48.1 48.2 48.3 48.4 48.5 48.6 48.7 48.8 Dimitris C. Gournelif; Gregory G. Laskarisb; Robert Verpoorte (1997). "Cyclopeptide alkaloids". Nat. Prod. Rep. 14 (1): 75–82. doi:10.1039/NP9971400075. PMID 9121730. 
  49. ↑ Aniszewski, p. 11
  50. ↑ Plemenkov, p. 246
  51. ↑ 51.0 51.1 Aniszewski, p. 12
  52. ↑ 52.0 52.1 Dewick, p. 382
  53. ↑ Hesse, pp. 44, 53
  54. ↑ 54.0 54.1 54.2 Plemenkov, p. 224
  55. ↑ 55.0 55.1 55.2 Aniszewski, p. 75
  56. ↑ Orekhov, p. 33
  57. ↑ 57.0 57.1 57.2 Chemical Encyclopedia: Tropan alkaloids. xumuk.ru
  58. ↑ Hesse, p. 34
  59. ↑ Aniszewski, p. 27
  60. ↑ 60.0 60.1 60.2 60.3 Chemical Encyclopedia: Pyrrolizidine alkaloids. xumuk.ru
  61. ↑ Plemenkov, p. 229
  62. ↑ "Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids". ChemBioChem 6 (6): 1016–1022. 2005. doi:10.1002/cbic.200400327. PMID 15861432. 
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  65. ↑ Plemenkov, p. 225
  66. ↑ Aniszewski, p. 95
  67. ↑ Orekhov, p. 80
  68. ↑ 68.0 68.1 68.2 68.3 68.4 68.5 Chemical Encyclopedia: Quinolizidine alkaloids. xumuk.ru
  69. ↑ Saxton, Vol. 1, p. 93
  70. ↑ Aniszewski, p. 98
  71. ↑ Saxton, Vol. 1, p. 91
  72. ↑ Joseph P. Michael (2002). "Indolizidine and quinolizidine alkaloids". Nat. Prod. Rep. 19 (5): 458–475. doi:10.1039/b208137g. PMID 14620842. 
  73. ↑ Saxton, Vol. 1, p. 92
  74. ↑ Dewick, p. 310
  75. ↑ Aniszewski, p. 96
  76. ↑ Aniszewski, p. 97
  77. ↑ 77.0 77.1 77.2 Plemenkov, p. 227
  78. ↑ 78.0 78.1 Chemical Encyclopedia: pyridine alkaloids. xumuk.ru
  79. ↑ 79.0 79.1 Aniszewski, p. 107
  80. ↑ 80.0 80.1 Aniszewski, p. 85
  81. ↑ Plemenkov, p. 228
  82. ↑ 82.0 82.1 Hesse, p. 36
  83. ↑ 83.00 83.01 83.02 83.03 83.04 83.05 83.06 83.07 83.08 83.09 83.10 83.11 83.12 83.13 83.14 83.15 83.16 83.17 83.18 83.19 Chemical Encyclopedia: isoquinoline alkaloids. xumuk.ru
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  85. ↑ 85.0 85.1 85.2 85.3 Begley, Alkaloid Biosynthesis
  86. ↑ 86.0 86.1 Saxton, Vol. 3, p. 122
  87. ↑ 87.0 87.1 87.2 Hesse, p. 54
  88. ↑ 88.0 88.1 Hesse, p. 37
  89. ↑ Hesse, p. 38
  90. ↑ 90.0 90.1 90.2 Hesse, p. 46
  91. ↑ 91.0 91.1 91.2 Hesse, p. 50
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  93. ↑ 93.0 93.1 Hesse, p. 47
  94. ↑ Hesse, p. 39
  95. ↑ 95.0 95.1 Hesse, p. 41
  96. ↑ 96.0 96.1 Hesse, p. 49
  97. ↑ Hesse, p. 44
  98. ↑ 98.0 98.1 98.2 Saxton, Vol. 3, p. 164
  99. ↑ 99.0 99.1 Hesse, p. 51
  100. ↑ 100.0 100.1 100.2 Plemenkov, p. 236
  101. ↑ Saxton, Vol. 3, p. 163
  102. ↑ Saxton, Vol. 3, p. 168
  103. ↑ Hesse, p. 52
  104. ↑ Hesse, p. 53
  105. ↑ 105.0 105.1 105.2 105.3 105.4 Plemenkov, p. 241
  106. ↑ Brossi, Vol. 35, p. 261
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  108. ↑ 108.0 108.1 Plemenkov, p. 242
  109. ↑ Begley, Cofactor Biosynthesis
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  116. ↑ Hesse, p. 58
  117. ↑ Plemenkov, p. 231
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  123. ↑ Orekhov, p. 212
  124. ↑ Aniszewski, p. 118
  125. ↑ 125.0 125.1 Aniszewski, p. 112
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  127. ↑ Hesse, p. 15
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  134. ↑ Saxton, Vol. 5, p. 210
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  139. ↑ Hesse, p. 72
  140. ↑ Hesse, p. 73
  141. ↑ Dewick, p. 396
  142. ↑ PlantCyc Pathway: ephedrine biosynthesis
  143. ↑ Hesse, p. 76
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  146. ↑ 146.0 146.1 Hesse, p. 81
  147. ↑ Brossi, Vol. 23, p. 376
  148. ↑ 148.0 148.1 Hesse, p. 77
  149. ↑ Brossi, Vol. 23, p. 268
  150. ↑ Brossi, Vol. 23, p. 231
  151. ↑ 151.0 151.1 151.2 151.3 151.4 151.5 Hesse, p. 82
  152. ↑ Spermine Biosynthesis
  153. ↑ 153.0 153.1 153.2 153.3 153.4 153.5 Plemenkov, p. 243
  154. ↑ Chemical Encyclopedia: Terpenes. xumuk.ru
  155. ↑ Begley, Natural Products: An Overview
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  164. ↑ "Cocaine". DrugBank. http://www.drugbank.ca/drugs/DB00907. 
  165. ↑ "Codeine". DrugBank. http://www.drugbank.ca/drugs/DB00318. 
  166. ↑ "Nicotine". DrugBank. http://www.drugbank.ca/drugs/DB00184. 
  167. ↑ "Morphine". DrugBank. http://www.drugbank.ca/drugs/DB00295. 
  168. ↑ "Yohimbine". DrugBank. http://www.drugbank.ca/drugs/DB01392. 
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  172. ↑ Orekhov, p. 11
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  181. ↑ Grinkevich, p. 5
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  198. ↑ Hardouin, Christophe; Doris, Eric; Rousseau, Bernard; Mioskowski, Charles (2002). "Concise synthesis of anhydrovinblastine from leurosine". Organic Letters 4 (7): 1151–1153. doi:10.1021/ol025560c. PMID 11922805. 
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  203. ↑ W.E. Conner (2009). Tiger Moths and Woolly Bears—behaviour, ecology, and evolution of the Arctiidae. New York: Oxford University Press. pp. 1–10. ISBN:0195327373.
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  206. ↑ Hesse, p. 303
  207. ↑ Hesse, pp. 303–309
  208. ↑ Hesse, p. 309
  209. ↑ Dewick, p. 335
  210. ↑ György Matolcsy, Miklós Nádasy, Viktor Andriska Pesticide chemistry, Elsevier, 2002, pp. 21–22 ISBN:0-444-98903-X
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  212. ↑ Hesse, p. 79
  213. ↑ Veselovskaya, p. 136
  214. ↑ Ibogaine: Proceedings from the First International Conference (The Alkaloids Book 56). Elsevier Science. 1950. p. 8. ISBN 978-0-12-469556-6. 
  215. ↑ Veselovskaya, p. 6
  216. ↑ Veselovskaya, pp. 51–52

General and cited references

  • Aniszewski, Tadeusz (2007). Alkaloids: secrets of life. Amsterdam: Elsevier. ISBN 978-0-444-52736-3. 
  • Begley, Tadhg P. (2009). Encyclopedia of Chemical Biology. 10. Wiley. pp. 1569–1570. doi:10.1002/cbic.200900262. ISBN 978-0-471-75477-0. 
  • Brossi, Arnold (1989). The Alkaloids: Chemistry and Pharmacology. Academic Press. 
  • Dewick, Paul M. (2002). Medicinal Natural Products: A Biosynthetic Approach (Second ed.). Wiley. ISBN 978-0-471-49640-3. 
  • Fattorusso, E.; Taglialatela-Scafati, O. (2008). Modern Alkaloids: Structure, Isolation, Synthesis and Biology. Wiley-VCH. ISBN 978-3-527-31521-5. 
  • (in ru) The chemical analysis of medicinal plants. Moscow: Vysshaya Shkola. 1983. 
  • Hesse, Manfred (2002). Alkaloids: Nature's Curse or Blessing?. Wiley-VCH. ISBN 978-3-906390-24-6. 
  • Knunyants, IL (1988). Chemical Encyclopedia. Soviet Encyclopedia. http://www.cnshb.ru/AKDiL/0048/base/RA/140004.shtm. 
  • Orekhov, AP (1955). Chemistry alkaloids (Acad. 2nd ed.). Moscow. 
  • Plemenkov, VV (2001). Introduction to the Chemistry of Natural Compounds. Kazan. 
  • Saxton, J. E. (1971). The Alkaloids: A Specialist Periodical Report. London: The Chemical Society. 
  • Veselovskaya, N. B.; Kovalenko, A. E. (2000). Drugs. Moscow: Triada-X. 
  • Wink, M (2009). "Mode of action and toxicology of plant toxins and poisonous plants". Mitt. Julius Kühn-Inst. 421: 93–112x. 

External links



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