Alkaloid

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Caffeine formula, a stimulating alkaloid.

It's called alkaloids (from alkali, "carbonates of alkalis", and -oid, " similar to", "in the form of") to those secondary metabolites of plants synthesized, generally, from amino acids, which have in common their water solubility at acidic pH and their solubility in organic solvents at pH alkaline. True alkaloids derive from an amino acid; therefore they are nitrogenous. All those with the amine or imine functional group are basic. Most of the alkaloids have intense physiological action in animals, even at low doses with psychoactive effects, which is why they are widely used to treat mental problems and relieve pain. Known examples are cocaine, morphine, atropine, colchicine, quinine, caffeine, strychnine and nicotine.

Their chemical structures are varied. An alkaloid is considered to be, by definition, a chemical compound that has a heterocyclic nitrogen from the metabolism of amino acids; if it proceeds from another route, it is defined as a pseudoalkaloid.

History and evolution of the term

The name alkaloid was coined by the German chemist Carl Meissner in 1819 to refer to natural products of plant origin that showed basic properties similar to alkalis. Given the limited structural information at the time, Meissner's definition was vague. Königs reserved the name “alkaloid” for basic compounds related to pyridine, and Guereschi considered the term synonymous with “vegetable base”. Winterstein and Trier (1910) considered alkaloids in the broad sense to be all compounds from any living being that contain basic nitrogen. These authors distinguished between a true alkaloid and a base related to alkaloids. A compound, according to this definition, had to meet the following requirements:

Submit a basic nitrogen
Nitrogen should be included in a heterocyclic system
Having a complex structure
Present powerful pharmacological activity
Have a restricted distribution to plants

As studies on natural products have progressed, compounds have been discovered that are considered alkaloids, but do not meet any of these requirements: many alkaloids do not present heterocyclic systems, their nitrogen is not basic (like nitro groups), they can present simple structures (as in the case of ephedrine, many amides —such as capsaicin—), they can be pharmacologically inert, and many alkaloids have been isolated from animals.

Hegnauer (1960) classified alkaloids into three types: true alkaloids, pseudoalkaloids and protoalkaloids. The term dry alkaloid is inferred from the nomenclature of natural products and is considered here as a fourth category:

(a) True Alkaloids: Side metabolites possessing heterocyclic nitrogen, and their carbon skeleton comes, partial or totally, from a protein amino acid.
(b) Pseudoalcaloids: Side metabolites that possess a nitrogen, but which have not been biosynthesized from amino acids, but are formed by transfer of nitrogen in the form of ammonia to a compound of terpenic origin, steroid, polycetic, monosaccharide or a fatty acid.

Aconitin, a pseudoalkaloid produced by species of Aconitum and Delphinium.

(c) Protoalcaloids: Side metabolites that do not form a heterocyclic system and are formed from a protein amino acid. Many of these compounds contain an amino, amida, etc.
(d) Secoalcaloids: Alkaloids that come from a real alkaloid, but in which by split of the heterocyclic ring is formed an open chain nitrogenated group.
(e) Genalcaloids: —or alkaloid aminated oxides — are derived by oxidation of alkaloids containing the R=(NO)-R group, where nitrogen has oxidation number +5, in contrast to normal alkaloids, where it is trivalent (R=N-R). His action is the same as that of the alkaloid from which they come, but it is more paused. They are named adding the gen prefix to the name of the alkaloid. Some genoalkaloids are found in nature, such as the geneserine (derivate of the alkaloid thatrine (fisostigmina)) present in the haba of Calabar.

There are natural products whose consideration as alkaloids is under debate:

Nitrogenated bases (Adenine, thymine, guanine, uracyl and cytosine due to their primary role as nucleotides and nucleic acids.
Them non-proteinian amino acids because their biological activity is not by joining a cellular receptor site, but because they replace protein amino acids and consequently form defective proteins.
Sphingolipids, because they are cell membrane components.
Vitamins (especially those of complex B) for being considered primary metabolites with catalytic activity.
Cyanogenic glycosides because their biological activity is not by joining a cellular receptor site, but because hydrolysing produces cyanideic acid, which is the one with the biological activity.
Glucosinolates because their biological activity is not by linking to a cellular receptor site, but because hydrolysing produces isotiocyanates, which are those that present the biological activity.
Them aminoazúcares, such as glucosamine, for being considered rather as glucids.
Them tetrapirrolessuch as porphyrin and corrin are still in debate, as some of them are secondary metabolites (such as turacin) and others are considered primary because metals such as iron (Hemo) magnesium (Clorophiles) or copper (Citocromines) and operate as oxygen or electron conveyors.
Non-ribial peptides, anhydropeptides and betalactamic antibiotics remain in debate, as they may be referred to as alkaloids or not. They will be considered in this article only as structural prototypes.

The isolation of the first alkaloids in the 19th century roughly coincided with the introduction of the percolation process for the drug extraction. The French pharmacist Charles Derosne probably isolated the alkaloid later called narcotine in 1803, and the pharmacist Friedrich Sertürner investigated opium and isolated morphine. This was quickly followed by the isolation of other alkaloids such as strychnine, caffeine, among others.

Cocaine is the oldest alkaloid in terms of its structure and synthesis being established, but others, such as colchicine, took more than a century for their structures to be defined.

In the Mesoamerican area, a wide variety of alkaloids have been used in traditional Mayan medicine since ancient times. Psychotropic substances, both alkaloids and alcohols, have been used for more than two thousand years for medicinal purposes and in ceremonial rituals. Their use is regulated by women over 39 years of age (3 x 13 cycles of biological evolution according to their own scientific approach), and they are normally administered in a ceremonial way in which the person who ingests them is surrounded by other specialized members of the community.

Biological activity

Its biological activities are important due to its hormonal mimicry and its intervention in the main reactions of cell metabolism. Despite being substances that are not very similar to each other from a structural point of view, they have similar physiological properties. Many alkaloids are the cause of poisoning in humans and animals. The most common form is poisoning from herbal infusions for medicinal purposes, this being an important cause of death, especially in children. Its presence in vegetables makes it possible to accidentally incorporate it into food, creating an easy way of poisoning.

They generally act on the central nervous system, although some affect the parasympathetic nervous system and others the sympathetic nervous system, for example, cocaine acts by preventing the reuptake of dopamine from the synaptic terminal, which produces a greater effect of the dopamine receptors.

The biological activity of alkaloids is very diverse; the most studied is the euphoric action that some have, such as cocaine, although there are also alkaloids with depressant effects on the central nervous system such as morphine.

Pyrrolidine alkaloids are associated with pyrrolizidine structures; they are secondary metabolites of a wide variety of plants, including species found throughout the world. These plants are the cause of numerous cases of cattle poisoning, and have caused great economic losses. They are also a cause of death in humans, especially in underdeveloped countries, as a consequence of the contamination of cereals and seeds, which is why they are of great importance in the field of food. It is believed that the ingestion of herbs and vegetables that contain these alkaloids cause ailments. The structure of these alkaloids consists of two rings of 5 linked atoms that share a nitrogen atom. In nature, rings generally have hydroxymethylene groups in the c-1 position and hydroxyl groups in c-7 as substituents; this structure is known as a necina. Typical examples of this base are heliotridine and retronecin.

Phytochemistry

Extraction methods are very varied, but purification by means of supercritical fluids, specifically with carbon dioxide, has recently been gaining momentum. To obtain plant alkaloids, they are extracted from the parts of the plant that contain them, with water if they are in the form of salts (soluble) or with dilute hydrochloric acid if they are in the insoluble form.

Regarding their detection, there are many methods: chromatographic procedures, colored reactions (Mayer, Dragendorff, Bouchardat reactions... although they are not specific to alkaloids: a positive result can be obtained in the presence, for example, peptides). Spectroscopic methods such as mass spectrometry, nuclear magnetic resonance and infrared spectroscopy are currently used.

Classification by chemical structure

Non-heterocyclic compounds

Since non-heterocyclic pseudoalkaloids, protoalkaloids, and secoalkaloids do not have a heterocyclic structure, they can be considered to have a highly diverse hydrocarbon structure. In this section these compounds will be classified by their functional group:

Functional group	Structure	Examples
Primary Amine		biogenic amines, anthranic acid, p-aminobenzoic acid, bleniona.
Secondary Amine (R¹ = H) or tertiary		Spermine, spermidine, sarcosine, peshawarina, narcein, joubertiamine, cordiformmide, lilacinona, lepiotaquinone, tetracyclines, taspina.
Sal de amon cuaternaria		Betains, muscarins.
Primary		Anandamida, nicotinamide, cerulenin, agro-cook.
Secondary and tertiary		Non ribosome peptides. Pigs.,,,,.................................
Guanidina		Galegine, creatine, hyrudonine, spherodies, fontainein
Nitrilo		cyanogenic glycosides
Dip		Kinamicins, agaritine, gyramitrine, headingflavina, craniformin, stephanosporine.
Azoxi		Cycsine, azoxybacillin
Nitro		β-nitropropyonic acid and its esters, cloranphenyl, aristocycic acid, 1-amino-2-nitrocyclopentanocarboxylic acid, 3-nitro-4-hydroxyphenylacetic acid, aureotin, myerotoxin, ascoclavine
Hydroxylamine and oxyma		Deferrioxamines B, deferoxamines, hadacidina, lobatamides

Heterocyclic Structures

Alkaloids and pseudoalkaloids will be classified below according to their heterocyclic structures.

Name	Skeleton	Examples
Aziridina		Acid 2,3-aziridindicarboxylic, disidazirin.
Azetidina		Azetidin-2-carboxylic acid, mugineic acid, 3-azetidinone, 3,3-azetidinodiol, SQ 26,180, nicotianamina, penaresidines, penazetidines, calidafninone, betalactamic antibiotics.
Pirrol		Pirrolidins: Cuzcohigrina, higrina, higrolina, stachidrina, ficina, vochisina, eleocarpine, dendrocrisanins, agaricone, pirrocyclines, chabamida F, equisetin, fomasetin, salinosporamides, pseurotins, kafiinic acid, ruspolinona, gerrardina, aminopirrolodin₁ and C₂, anisomycin, antibiotic GKK 1032A2, barmumicin, brousonetins, codonopsine, anisomycin, cucubalactama, detoxin, hydroxypirrolidins, divaricataester A, donaxaridine; dysysybetin, fulvanine A, involved, irin, lanopilins, morphine Pyrroles, Pyrrolonas and Succinimides: Pyrolocarboxylic acid, tenuazine, porphyllins, porphylline, prodigyins, ryanodine, pirrolezantine, 3-pirrolacrylic acid, 2-cyanopirrol, chistamidins, pharynomycin, pirrolo-2,3-dicarboxylic acid
Imidazol		Urinanic acid, histamine, murexine, diphetamine, ergotionine, pilocarpine, dolicoteline, pilosin, nagelamides, sceptrines, clatrodine, oroidine, himenidine, keramadina, creatinine, polycarpene, steletazoles, chrysorinas, lepidines.
Pirazol		β-pirazole-1-il alanine, pirazophrine
Oxazol		Oxazolidins: Goitrina, lipoxazolidinonas Oxazoles: Muscazona, hennoxazoles, rhizoxin, forboxazole, anulolina, halfordinol, texalin, texamine, vibriobactin, curromycin A, martephramines, Almazolone, clavosins, quivosazoles.
Isoxazole		Isoxazolidins: Cycloserin Isoxazoles: Ibothenic acid, trichomal acid, thighs.
Tiazol		Epotilonas, thiamine, micrococcina, mixotiazoles, nostociclamides, thiostreptona, raocilamides, dendroamides, tenuacilamides, yersiniabactin, healers, venturamides.
1.2.4-oxadiazol		Qualic acid
Piridina		Piperidinas: Coniine, conicein, pinidine, lobelanine, pipecolic acid, glutanimin, indigoidine, sedamine, lobelin, anaferin, piperin, nufaramine, carpain, estenusin, evoninic acid, wilphineic acid, evonine, rohitukin Piridines:.............
Pirimidina		Ectoin, capreomicidine, thymine, cytosine, uracyl, vicin, convicin, latirin, barbiturate acid
Pirazina		Pulcherrymic acid, asperegylic acid, ligustrazine, riterazins, anhydropeptides, chromtonin, dredmacidins, sarcodonins, sarcoviolins, abornousin, picrorocceline, rhodotoric acid, echinine, flavacol, micelianamida, barrenazins.
Piridazina		Piridazomycin, Piridazocidina
Tiomorfolina		Condrine, thiomorphine-3-carboxylic acid, cycloaliine
Azepina		Azepanos'Blessings, isobengamides, muscaflavina, Ciliatamides, ofiocordine, balanol, chalciporone, peritoxin A, ustalimida, amamistatin A, antibiotic A 500359A, balanol, calpinactama, capuramicin, carboxymicbactins, ciliatamide A, circintocin
Azocina		Otonecina
Azacicloalcans		Motuporaminas, macrocyclolactamas, Keramafidina C
7-azabicycle[2.2.1]heptano		Epibatidina
Tropano		Atropine, scopolamine, hyosciamine, cocaine, ecgonine, calistegines
9-Azabiciclo[3.3.1]nonano		Pseudopeletierin, eufococcinin
Pirrolizidine		Necinas: Retronecina, heliotridina, laburnine, indicine, lindelofina, sarracina, platifilina, tricodesmina, phenopsine, licopsamina, creatonotins, calimorfina, supidina, rosmarinecin, danaiona, traquelantamidine, niece, crotanecina, platinecin, turneforcidina,
Indolizidine		Swainsonine, castanospermine, pumiliotoxins, lentiginosine, polygonatins, monomorine, slaframine, serratinine.
Indol		Methyl, methyl, methyl
Isoindol		Cytocalasins, quetoglobosins, cespitulactamas, hericerin, esrenins, cytocytes.
Benzotiazol		Luciferina
Benzoxazol		Nakijinol, pseudopteroxazoles
Indazol		Nigelidina, nigelicine, nigeglanin
Pirrolo[3,2-b]piridina		Laccarina, agrocibenin, pyramids
Pirrolo[1,2-a]pirazine		Vercapamida A
Imidazo[1,2-a]pirazine		Coelenteracina, vargulina
Quinolina		'Hydroquinolins: Mirionine, tortuosamine 'Quinolins: 2nd, 4th, 4th, 2nd,
Isoquinolina		Tetrahydroisoquinolinskinabine, phylocriptine, filthine, Isoquinolinas: Isoquinolin, salsoline, lofocerine, coridaldine, oxihydrstinine, ancistrocladines, papaverin, laudanosine, sendaverine, papaveraldine, carcrisine B, fusarimida, cassiarinas, monascorubramine, fredericamicins A and B, lagoonmicin.
Quinolizidina		Lupinine, nufaridine, nufarolutin, nufacristine, nufarpumilamins.
quinazolina		Febrifuguine, glycoin, arborine, glycosminine, glycoscimine, glycophymoline, glomerin, homoglomerin, equinozolinone, tetrodotoxin, 2-acetilquinazolin-4(3H)-one, 7-bromoquinazolinoline-2,4-diona, 7-hydroxyequinozolinone, ditioquinazoline.
Quinoxine		Baimantuoluoamida B
3H-Pirrolo[1,2-a]azepine		Estemoadina
3H-3-benzazepina		Roeadina, papaverubinas
2,7-Naftiridina		Lofocladinas
Purina		Xantosina, adenine, guanina, cordicepine, eritadenins, nebularin, cytokinins, caffeine, teofiline, teobromine.
Pteridine		Biopterins, leucopterina, xantopterina
Pirimido[5,4-e][1,2,4]triazina		Reumitsina, toxoflavina.
Pirazolo[4,3-e][1,2,4]triazina		Fluvial
Carbazol		3-Methylcarbazole, 3-Formilcarbazole, 3-carbazolecarboxylic acid, 1-Hidroxi-3-methylcarbazole, clausins, murrayafolins, koenolina, murrayanine, mukoenic acid, mukonine, 2-hidroxi-3-methylcarbazole, mukonal, mukonidine
Acridina		Rutacridona, melicopidina, Xantevodina, eskimianina.
Fenazina		Piocianine, aeruginos.
Fenoxazina		Cinabarin, cinnabarnic acid, tramesanguina, polystictin, phenoxazon, α-aminophenoxazone, orceins, picnoporin.
Benzog]isoquinolina		Tolipocladine
Benzog]quinolina		Cleistofolina
4H-1,4-benzoxazina		DIMBOA
Quinuclidina		Quinine quinidina fivenine, cinchonidine.
1,2-Dihydrospiro[indol-3,3'-pirrolidina]		Coerulescina, Horsfilina
β-Carbolina		Harmano, harmina, harmalina, eleagnina, cecilin, tripargimina, bruneins, flazina, flazinamida.
Benzo[g]pteridine		Lumazina, Limicromo, isoaloxazines, roseoflavina
7H- dibenzod.f]azonina		Protostefanine
Benzoh]isoquinolina		Chiloenina, santiagonamina
Fenantridina		Crinina
Benzoc]cinolina		Necatorine
Pirido[1,2-a]indol		Gliotoxin, dioxopirazinoindoles
Pirido[2,1,6-of"quinolizine"		Coccineline, mirrine, precoccineline, hypodamine, convergine, poranterin, porantelidina, porantericine, propilein
11bH- pissed[2,1-a]isoquinolina		Emetina
Pirrolo [2,1-a]isoquinolina		Lamelarinas
Pirrolo[4,3,2-of]quinolina		Micearubinas, makaluvaminas, damirona C, hematopodinas.
2H-1,8,8b-Triazaacenaftileno		Cylinderspermopsin and its derivatives.
5H-5,6,8b-Triazaacenaftileno		Ptilomicalins, batzeladins, cambrescidins.
9aH-5,8-diazabenzo[3]cd]Azuuleno		Aaptosamine
4H-benzoof][1,6]-naftiridina		Aaptamines, isoaaptamines
Pirido[2,1-j]quinolina		Cylindricin B, fasicularin, polycytorol A
1H-pirrolo[2,1-j]quinolina		Cylindricins A, K, D, E, J, I; Lepadiformins A and B.
1.8-dihydropirrole[2,3-b]indol		Fisostigmina (eserin), etheramine, fisovenine, eptastigmine, flustramines.
5H10H- Spread it[1,2-a:1',2'-d]pirazine		Vercapamida C, pyrocol, aranotin.
2-oxa-6-azatriciclo[4.2.1.0^3.7"Nonano."		Lolinas, temulina
Dibenzo[c,g]azecina		Protoxin, coricavamine, coricavidina.
Dibenzo[b,i]quinolizina		Cohirsina, shaheenina, cohirsinine, cohirsitinine.
Pirrolo 2,1,5-cdIndolizine		Mirmicarinas
1H10H- [1.2-c]purina		Saxitoxins
Indolo[2,1-a]isoquinolina		Criptowolidina, criptowolinol, criptowolina.
9H-Indeno[2,1-b]piridina		Haouamina
Azepino[3,2,1-hi.]indol		Estenine, tuberostemonine, estemoamide, estemonine, neostemonine, chromomine, estemonidine.
6,10-Methane-4,6-dihydropyride[1,2-a]azepine		Securiniaminas, sufruticodina, securinoles, filocrisine
2.5-Methane-9H-pyride[1,2-b][1,2]oxazepine		Filantidina, secuamamide D
4H- dibenzode,g]quinolina		Alkaloids aporfinoids: Glaucina, boldina, bulbocapnine, nantein, hernandialin, nuciferin, liriodenine, pukatein, laurotetamine, lauroscolzine, scoline, magnoflorin, duguenain and pancoridine, talifaberine, urabain, dehatrifin
7H- dibenzoof,h]quinolina		Menisporfina
Indeno[1,2,3-ij]isoquinolina		Rufescina, imelutein
1.2-Epimino-3H-pirrolo[1,2-a]indol		Mitomicines
Eupolauridina		Eupolauridina and its derivatives
Pirrolo[3,2,1-of]fenantridina		Licorina
7H-Nafto[1,2,3-ij][2,7]naftiridina		Sampangina, eupomatidines
Spiro[2,5-cyclohexadieno-1,7'(1'H)-cyclopenta[ij]isoquinolin]		Orientalinone, glaziovina, estefarina, mecambrina, pronuciferin. Number: Roehibridina
1.2-dihydrospiro[2-H-indeno-2,1'-isoquinolin]		Lahorina
Benzod]-[4,5-g[4,3,2-jk][2]benzazepina		Dragabina
Esparte		Esparte
1H.4H.9H-Dipirted[2,1-b:3',2',1'-ij]quinazolina		Sibiridina, schoberina
Morphine		Codeine, tebaine, salutine, morphine, oripavina
Hasubanano		Hasubanonine, cepharamine, cephasamine
(1S.9R)-7,11-diazatriciclo[7.3.1.0^2.7]tridecano		Citisine, angustifolina
Dibenzo[f,h]pirrolo[1,2-b]isoquinolina		Ficuseptins, cryptopleurine and thiophorin.
(6S,11bS)-6,11b-Methane-3a,6,11a,11b-tetrahidrofuro[2,3-c[1,2-a#Balepine		Securiniaminas, sufruticodina and A-D securinoles
Dibenzoa,g]-9aH- What?		Protoberine, anisocycline, palmatin, corlipalmine, discretamine, berlambina, lambertine, choreximine, talifaurine, coptisine, escoulerin, styling.
6,15-epimino-4H-Ioquino[3,2-b][3]Benzazocina.		Saframicina, renieramicina, jorunamicina
(1R,2R,7S,12R,13S,15S)-14-Oxa-6,8-diazapentaciclo[10.6.0.0^2.7.0^2,15.0^8.13Octadean (Nitraramida)		Nitraramida, nitrabirina
3.5-o-fenilen-2,3,4,5-tetrahydro-1H-2-benzazepina		Amurensina
3.6-Dihydropirrolo[3,2-e]indol		Duocarmicins, yatakemicin.
5,11-Epiminodibenzoa,e][8]anuleno		Pavinas, isopavinas
10H-blue[1,2,3-ij]isoquinolin		Imerubrina
5H-Indeno[1,2-b]piridina		Oniquina
Dibenzo[6,5,4-cd:f]indol		Cefaronas
5H-Isoindolo[1,2-b][3]benzazepina		Lennoxamine
Benzo[6,7]ciclohept[1,2,3-ij]isoquinolin		Kreysigina,
9H-azulene[1,2,3-ij]isoquinolina		Grandirubrina
Homoeritrinano ([4,5-h]indolo[7a,1-a][2]benzazepina)		Schelhameridin, erimelantine, erisopinoforin.
Eritrean		β-Erytroidine, Erisotramidina.
3H-cyclopenta[b[1.2-a][3]benzazepina		Cefalotaxine, haringtonin, isoharringtonin, cephalezomines
Dibenzo[5,6-a:4',5'-g]-4H- What?		Cavidina, Talictrifolina, apocavidina, isoapocavidina.
Quinolino[2',3':3,4]b]quinazolina		Luotonins
Benzo[c]fenantridina		Quelidonina, sanguinarina, palmatina, queleritrina
Benzo[j,k]acridina		Necatarona
Indolo[3,2-c]quinolina		Isocriptolepine
Quindolidina		Quindolidina, Criptolepina
Quinindolina		Neocriptolepine
7H-Indolo[2',3':3,4]pyrido[2,1-b]quinazolina		Evodiamine
5H-indolo[2,3-a]pirrolo[3,4-c]carbazol		Arciriaflavinas, estaurosporine
9H-Quino[4,3,2-of][1,10]fenantrolin		Ascididemine
11,22-Diazatetracycle[11.11.2.1^2.22.0^2.12]heptacosane		Ircinate

Pyridal core alkaloids: to this group belong nicotine, pilocarpine and spatein. Nicotine is found in tobacco juice with other alkaloids. It is a colourless, smelly liquid similar to tobacco and hot and spicy flavor. It's very toxic in high doses.
Isoquinoleic core alkaloids: they are found in papal and ranunculaceae plants. The most important is papaverin, which has hypnotic properties (although not as accentuated as morphine).
phenantrenic core alkaloids: the most important is morphine. It is found in the opium in the form of salt. It is used in medicine in the form of chloride and sulfate, such as sedatives, analgesics, anesthetics and soothing.
Alkaloids of tropical core: Atropine and cocaine belong to this group. The atropine is found in the juice of several plants such as the beautifuldone, brugmansia, floripondium, toloache and the estramony. Coca is extracted from coca leaves or Erytroxylium Coca, is of bitter taste, insensitizes the tongue, and is used in chloride-like medicine as a local anesthetic to cure pain and severe epistaxis.
Alcoholic core alkaloids: the most important are strychnine and brucina. Stricnine is one of the most energetic and toxic alkaloids, extracted from various plants of the genus Strychnosamong them the haba of St. Ignatius and the Vomica nut or Nux. It is of very intense bitter taste and is an extremely toxic substance. its ingestion produces tetanical seizures.
Undefined core alkaloids: are all those alkaloids whose constitution has not yet been clearly established. Among them is aconitin (very violent poison, used in therapeutics to combat certain ailments) and ergotinin (one of the active principles of the rye cornezuelo, which exerts a specific action on the uterus).

Classification by biosynthesis

Alkaloids are found forming salts with acetic, oxalic, lactic, malic, tartaric, and citric acids. Below is a summary of the biosynthetic diversity of alkaloids.

Protoalkaloids

Many compounds considered pseudoalkaloids could be included in the category of protoalkaloids if all those that do not form heterocyclic systems are considered. The most important ones to consider are amines and amides.

Amines

When an amino acid is decarboxylated, biogenic amines are formed. Histidine and tryptophan, as they possess a heterocyclic ring by themselves, will be considered in separate sections.

Amino acid precursor	Amina biogena	Structure
Glicina	Metilamina
Alanina	Etilamina
Serina	Etanolamine
Cistein	Cisteamine
Asparian acid	β-Alanine
Metionina	4-Methylsulfuro-1-propanoamine
Treonina	1-Amino-2-propanol
Glutamic acid	γ-aminobutyric acid (GABA)
Ornitina	Putrescina
Arginine	Agmatina
Lisina	Cadaverina
Fenilalanina	Fenetilamina
Tyrosine	Tiramina
DOPA	Dopamine
Valina	Isobutilamina
Leucina	Isoamilamine

Many of these amines form further derivatives, such as catecholamines. Ephedrines are formed from benzoic acid and pyruvate by the action of thiamine pyrophosphate.

Many amines can accept a second or even a third alkyl group to form secondary or tertiary amines. When an amino acid forms a trimethylammonium salt it is called betaine. Examples of betaines are glycinic betaine, trimethylserine (the precursor to choline) and hypaphorin. Muscarine is an ammonium salt of Amanita muscaria.

Amides

Amides are formed by the heteroatomic connection of an amine or ammonia with an acyl-coenzyme A.

Guanidines

There are amines that receive a carbimino group from arginine, such as galegine and creatine.

True alkaloids

They always have a nitrogen that is part of a heterocycle, they are basic in nature, they are normally in the salt state and biogenetically they come from amino acids.

Alkaloids derived from serine, cysteine and glycine

Serine

La serin forms the cycloserin, an isoxazolidin-5-one by intramolecular oxidation of nitrogen.
Seine can form acid 2,3-diaminopropyonic (acid)DAP), which in turn can form the quisqualic acid, a non-proteinnic amino acid with a ring of 1,2,4-oxadiazolidine, isolated from the piscuala. DAP also forms β-lactamas, which are constituents of SP 26 antibiotics.

Seine can be incorporated as etanolamine to alkaloid epilacneno azamacrólide.

In several non ribosomal peptides, seine can form oxazoles and these can be referred as alkaloid peptides. Oxazoles are the result of iclation and oxidation of non ribosome peptides of seine or throonine

Where X = H, Met for seine or treonin respectively, B = base.
(1) Enzymatic Cycling. (2) Elimination. (3) [O] = Enzymatic oxygenation.

Cysteine

Cysteine can form various thiazoles:

An example is acid 2-methyl-1,3-tiazol-4-carboxylic. This thiacolic acid is the initiation unit of polycytes such as epotylins.


Epotilone C

Another example of cysteine tiazoles are the Mixotiazoles, which were isolated by Höfle and his collaborators in the 1970s. Mixotiazole A was first described in 1978 in a patent and was later described in the 80's. Mixotiazoles are 2.4'-bi-1,3-tiazoles isolated from fungi that form from a polycyte with a cysteine initiation unit and another cysteine molecule.

Cysteine can also form thiomorphins in marine organisms, such as condrine.

Wisteria

Glicin can form imidazole rings, such as AIR and creatinine.

From the glycine the guanine and adenine purin bases are formed. From the adenine, several purinic compounds are formed, such as cordicepine, eritadenins, nebularin, cytokinins, caffeine, teofiline, teobromine, malonganenonas and nutingins.

From the guanine you can sistetize isoaloxazine and pteridine rings. Many insects can produce pigments from pteridins (e.g. Drosophin, Leucopterin, Drosopterina) or other derivative rings:

La reumitsina and the toxoflavina are compounds that present as the base skeleton the pirimido[5,4-e]-1,2,4-triazine (also referred as Azapteridines). These compounds were isolated from gender bacteria Actinobacter. These triazines may come biogenetically from a purine or pteridine.

Examples of azaguanidines is zarzisine.


Pirimido[5,4-e][1,2,4]triazina

Alkaloids derived from aspartate

In this section we consider the alkaloids of amino acids biosynthetically related to aspartic acid: aspartate, asparagine, threonine and methionine.

Aspartate and asparagine

Aspartate can form another related amino acid by reduction of the carboxyl terminal and reductive amination: 2,4-diaminobutyric acid (DABA). When decarboxylated, it can form 1,3-diaminopropane. Aspartate can accept a carbamyl group via its amino nitrogen to form N-carbamoylaspartic acid. Additionally, aspartic acid can condense with dihydroxyacetone phosphate to form the vitamin nicotinic acid.

Pirimidins: The precursor is the orotic acid, which is formed by heterocyclization of the acid N- Carbamoilaspártico. Pyridic bases (Uracilo, Timina, Citosina) arise from this precursor. Barbiturate acid is the product of catabolism of pirimidins. Examples of alkaloids from orotic acid are the vicin, convicin, of Vicia faba and the cytokine Pectinophora gossypiella. Latirine could be considered as a non-protein amino acid or alkaloid due to the pirimidine ring. ectoine is a 2-replaced pirimidine that does not come from the path of orthotic acid, but from acid 2.4-diaminobutyric acetylated in carbon nitrogen 4.
Pirazoles: Pirazol rings are not abundant in nature, and have chemotaxonomic value. One case is β-pirazole-1-il alanine and pyrazophrine.

Pyrid alkaloids[1,2-a]azepinic: Form in the sponge Niphates digitalis from subtheric aldehyde and 1.3-propanoamine (which comes from the descarboxylation of 2.4-diaminobutyric acid)

Pyrid alkaloid biosynthesis[1,2-a#Balepinics

Threonine

Several non-protein amino acids with toxic activity—such as hypoglycins, canalin, and canavalin—are thought to be derived from threonine.

Methionine

The nitrogenous secondary metabolites of methionine mainly consist of methionine glucosinolates, homomethionine and dihomomethionine. Goitrin is a 1,3-oxazolidine formed from the glucosinolate progoitrin. S-Adenosyl methionine is reactive enough to form an azetidine system, in the form of azetidine-2-carboxylic acid, which is the basis of the isopeptides known as mugineic acids. Some azetidines are presumed to be derived from this precursor, such as 3-azetidinone and 3,3-azetidynediol.


Acid (S)-(-)-2-Azetidinocarboxylic	Goitrina

Nicotinate

Nicotinic acid is formed de novo in plants by condensation of a triose molecule and an iminoaspartate molecule (the imino derivative of aspartic acid), while in animals and fungi it can be formed by tryptophan catabolism. Nicotinic acid (pyridine-3-carboxylic acid) is the structural basis of many pyridine alkaloids. Fusaric acid is a pyridine alkaloid that is formed under the same condensation principle, but from aspartate and triacetic acid.

Pyridines: This vitamin can be discarded to give piridine, hydrogenated to form dihydropyridins or oxidize. Some pyridines related to nicotynic acid are the alkaloids of the palm Areca (Arecoline, guvacin), the seed of the ricin, the hermidine of the Mercurialis annua and the alholva's trinelin. Several plants of the Celastraceae family produce evoninic acid esters (nicotinic acid linked with a 2-methylbutyric acid molecule) and agarofuran type sesquiterpenos. Examples of these alkaloids are maytoline, mayine, acantotamine, evonin, neoevonin, euonimin, hypocratins, emarginatins.


Evonic acid	General structure of the alkaloids of Celastraceae.

Bispiridines: The bis-pyridines are formed by the coupling of free radicals (Crisohermidina) or by condensation (Anatabine). Piridine rings can be coupled with other rings like in the case of nicotine (Pyrrolidynic ring) or anabasine (Pypiridine ring of lysine)


Crisohermidina	Anatabine

Hachijodinas: They are hydroxylamins derived from fatty acids that form when nicotynic acid is used as an initiation unit:

Alkaloids derived from amino acids of the glutamate family

Several alkaloids come from amino acids of the glutamate family (glutamine, glutamate, proline, ornithine, and arginine.

Glutamate and glutamine

When glutamine heterocyclizes at its ends, form the glutanimineWhich has a piperidine skeleton. When dimeriza forms the indigoidine (Estructura: 1.1',2,2',3,3',4,4'-octahidro-4,4'-bipiridina).

Indigoidina

Hydroxylate glutamate can form an isoxazole in a manner similar to cycloserin to form ibothenic acid, a non-proteinnic amino acid with an isoxazole heterocycle. This amino acid is the precursor of many mushroom isoxazoles Amanita muscaria, such as thigh and trichomal acid.

The lascivol is a glutamine amide and a polycetic precursor of the many indian structure compounds, such as 2.4-dimetilindol, (2-methyl-4-hydroxymethylndol, (2-methyl-4-methoximetilindol and 2.4-dimethyl-5-metoxindol

Proline

Proline and ornithine can form alkaloids with a pyrrolizidine nucleus; in fact, proline itself is a pyrrolizidine. From proline can be formed:

2-pirrolocarboxylic acids as well as their brominated derivatives, isolated from sponges.
Stachyrin, present in betanic, is proline betaine.
Antibiotics beta-lactamic carbapenam type.

Many clavicipitous fungi produce alkaloids with 2-oxa-6-azatricicle skeleton[4.2.1.0^3.7]nonano, such as lolina and temulin, from proline and homoserine.

Prodigiosins are manirlic pigments produced by gender bacteria Serratia. The first pirrol ring is biosynthesized by the dehydrogenation of a proline thyoester with the enzyme:

Prodigiosine

Serratia marcescens, prodigiosine-producing bacteria

Subsequently, the 2-pyrrolecarbonyl residue is condensed with a new pyrrole ring of polyketide type origin:

Ornithine and arginine

Ornithine and arginine are related biosynthetically, since arginine comes from ornithine by adding a carbamyl group to the terminal nitrogen of ornithine with subsequent addition of an aspartate nitrogen (first 3 reactions of the urea cycle)

Ornithine forms alkaloids of two types: those derived from putrescine and those derived from the polyamines spermine, homospermine, and spermidine.

Derivatives of the rot: Putrescina can heterociclize to form the cation N- methyl-Δ¹- Pyrroliny.. This metabolic intermediary can be incorporated into many routes such as:

(a) Training of 3-pirrolidin-2-il piridines, such as nicotine

(b) Training of azaazulens, such as (+)-5-epiindolizidine 167B.

(c) Formation of two acetyl units: By the same mechanism of the polycytes (Only the initiation unit is a magnet, so instead of a Claisen condensation a Mannich condensation is carried out. Thus form the higrine, cuscohigrine and dendrocrisanins. When the polycyte-type derivative heterocyclizes the tropane skeleton. Many tropical alkaloids form in solanaceae and erytroxylaceas, such as D., Atropa,Mandragora and Erythroxylon. Examples of these alkaloids are cocaine, hyosciamine, tropine, calistegins, schizantines, litorina, methelloidine and scopolamine.

(d) Alkaloids pirrolidinflavonoids: The rings of N- methyl-Δ¹-pirrolinium can be incorporated into flavonoid structures. Examples of these alkaloids are ficina, vochisina and eleocarpine


Ficina	Vochisina

Dendrocrisanins are pirrolidine rings with substitute cinamoyl in nitrogen.

Agaricone is a pigment produced by Agaricus xanthoderma.

-Polyamine derivatives: The homoesperidine can give a double cycling to produce biosynthetically pirrozilidinic alkaloids. The plants of the genus Seinethe monarch butterfly (Danaus plexippus and other related lepidopteros (which consume the plant) and several orchids are the main producers of pirrolizidinic alkaloids:

Examples of these alkaloids are falenopsin, lycopsamine, retronecin, creatonotins, calimorphine, supidine, rosmarinecin, otonecin, danaione, trachelantamidine, plataphyllin, sarracin, hastanecin, crotanecin, heliotridine, platynecin, turneforcidin, ipangulines, and mynalobins.

Many macrocyclic alkaloids come from spermine, as in the case of the lunarine (Insulation of the Lunaria annua(c):

The structure of motuporamins suggests an origin from polyamins and a medium-sized fatty acid:

Alkaloids of the Stemona: The species of the family Stemonaceae produce a large class of diverse alkaloids structurally related to the 4-Azaazulene core. Its roots have been used for the treatment of tuberculosis, bronchitis and parasitosis. Examples of these alkaloids are stenine, tuberostemonine, stemoamide, estemonine, neostemonine, chromomine and estemonidine.

	Tuberoestemonine

Alkaloids Elaeocarpus: The species of the genus Elaeocarpus produces a series of indolizidal alkaloids, but unlike those who are swansonin type, these alkaloids are presumed to come from the spermidine. They are classified into:

- Alkaloids 8-acilindolizidinics: Examples include the A-C eleokanins, E and D grandisins, isoelaeocarpicin and eleocarpenin.

- Alkaloid type eleokanidine: They present a skeleton base of pirrolo[2,1-f][1,6]naftiridina or 1H-pirano[2,3-g]indolizine. Examples of these alkaloids are the A-C eleokanidins and the D and E eleokanins.

- Alkaloid type eleocarpine: They present a skeleton base 12H-[1]benzopirano[2,3-g]indolizine, such as eleocarpine, pseudoepiisoeleocarpilin, grandisins C and F, rudrakina, eleocarpilin, aloeleocarpilin, epialoeleocarpilin, epiisoeleocarpilin, isoeleocarpilin, epieleocarpilin.


Eleokanina A	Isoeleocarpicina	Grandisina G	Eleokanidina A	Eleocarpina

Arginine derivatives: Arginine is a precursor of several natural products, such as clavulanic acid, capreomicidine (a hexahidropirimidine), tetrodotoxin and saxitoxins (Saxitoxine, neosaxitoxin, GTX1-7, C1-C4, dcSTX, dcneoSTX, dcGTX 1-4) which present one isH10H- [1.2-cHurry up,

1H10H- [1.2-c]purina, skeleton base of saxitoxins

Verpacamides and peramide are anhydropeptides of arginine and proline:

Porphobilinogen derivatives

Porphobilinogen is the precursor of bilans, porphyrins, corrins, and bilins. Some insect-produced chromophore alkaloids derived from this compound are pterobilin, sarpedobilin, and forcabilin.

Alkaloids derived from lysine

Lysine can be biosynthesized by the diaminopimelate (DAP) pathway in fungi or by the α-aminoadipate (AAA) pathway. During its biosynthesis, metabolites such as picolinic acid and dipicolinic acid can be formed, which are isomers of nicotinic acid and quinolinic acid, respectively.

When lysine heterocyclizes, it forms the lysine lactam (Base skeleton: perhydroazepine). This lactam is the basis of the bengamides. Allysine is the transamination product of the amino terminal of lysine. Desmosine comes from this intermediate. Allysine can form pipecolic acid, which is a component of ascomycin and rapamycin. Decarboxylation of lysine produces cadaverine, which by heterocyclization produces Δ¹-piperideine. This ring can form several alkaloid systems.

Lysine alkaloids can be classified as cadaverine derivatives and pipecholate derivatives.

Them derivatives of the are mainly those that come from the incorporation of a piperidina unit to various components, for example:

- Anaferin, peletierin and pseudopeletierin are derived from acetylation in a manner similar to the biosynthesis of the higrine and the tropane alkaloids.

- Stenusine is a derivative by condensing with isoleucin. Other examples include evoninic acid, wilfdodic acid, edulinic acid and evonin.

Estenusina

- Alcaloides piperidinflavonoids' An example is rohitukine, chromtacupines and the derivatives of the captain.


Schumannioficina	Rohitukina

- Alcaloides 1.3-diazepineflavonoids: For example, the north and isoquiledine.

- Cynolizidal alkaloids: They are formed by two piperidein units. They are found in several members of the Fabaceae family. Typical examples are lupine, lusitanine and castoramine.

- From peletierin and other derivatives new heterocyclic ring systems are formed, such as cytokine, spinaine, licodine, angustifolina, albine, fawcetimida, poranthrin, cernuine, sufocarpine, cryptopleurine, ormosamine, aphilin, lupanine, retamine, aloperin, baprorin


Esparte	Citisine	Angustifolina	Licodina	Ormosamina	Fawcetidina	Mirionina

- Anabasine, astrophylline and anabatin are bis-pyridines from Mannich condensation among other lysonic or nicotin-based piperidins.

Anabasina

- Lobelanine, lobelin and sedamine are formed by the incorporation of phenylpropanoid derivatives.

Lobelina

- Pipingrin, nigramid R, pipercyclobutanamide C and the H and I shaves are examples of piperidine alkamides.

- Indolizidal alkaloids: Castanospermine comes biosynthetically from pipecolic acid. This is condensed with two acetate units by means of Claisen condensations in the same way as in polycets, thus generating the 1-indolizidinona, which is the precursor of many indolizidonic alkaloids. Examples of these alkaloids are castanospermine, swainsonine, pumiliotoxins, lentiginosine, polygonatins and monomorine. Mirmicarinas present an indolizidine skeleton fused with a pyrrol (Pirrolo[2,1,5-cd]indolizine. Indolizidal alkaloids may be fused with aromatic rings (Dibenzo[f,h]pirrolo[1,2-b]isoquinolin) as in the case of ficuseptins, chryptopleurine and thyloforin.


Indolizina	Pirrolo 2,1,5-cd Indolizine	Dibenzo[f,h]pirrolo[1,2-b]isoquinolina

Literary alkaloids: These cyclophanic alkaloids are made up of a cyclozolinic or piperidine cycle from lysine, which are esterified with phenylpropanoid aromatic acids or form ethers between aromatic rings.

Alkaloids of Nitraria: Gerrit-Jan Koomen and Martin J. Wanner classified alkaloids Nitraria, two of which come exclusively from the lysine: the spiroalcaloids (For example, (+)-nitramine, (-)-isonitramine, (-)-sibirin, nitrabirin, nitrabirin oxide, and sibirinin) and mandiperidynic alkaloids (Schoberine, dehydroschoberine, sibiridine and dihydroschoberine)

Acromelic acids: Insulated from the fungus Clitocybe acromelalga. They are biogenetically related to kainic acid and domoic acid. What is assured of all these alkaloids is the correlation with glutamic acid. Fusaric acid is condensed in a similar way, only forming a piridine alkaloid.


Acromelic acid A	Acromelic acid B	kainic acid	Domoic acid	Fusaric acid

Alkaloids derived from phenylalanine and tyrosine

Phenylalanine and tyrosine are biosynthesized by the shikimic acid pathway, via chorismate, prephenate, and arylpyruvates. Plants and bacteria synthesize both amino acids by separate routes, while animals and fungi can obtain tyrosine by hydroxylation of phenylalanine.

The alkaloids of the tyrosine-phenylalanine amino acids are a very broad and diverse group, which is why they will be classified by their biosynthesis into the following types:

(a) Alkaloids Securinega

(b) Alcoholic alkaloids

(d) Alkaloids mesembrenoids

(e) Norbeladian alkaloids

(f) Anhydropeptides of aromatic amino acids

(g) Alkaloid cytoanics

(h) Alkaloids of the cycle-DOPA

(i) Dry alkaloids-DOPAs

Securinega alkaloids

Plants of the genus Securinega produce alkaloids with the base skeleton (6S,11bS)-6,11b-methane-3a,6,11a,11b-tetrahydrofuro[2,3-c]pyrido[1,2-a]azepine. This small group of 30 alkaloids seems to come biosynthetically from tyrosine and lysine, as is the case with securinine. Other examples are the securiniamines, sufruticodin, and the securinols A-D. Phylantidine has the structure methanofuro[2,3-d]pyrido[1,2-b][1,2]oxazocine. Sankawa et al. deduced that securinin may come from a tyrosine molecule and a cadaverine molecule. The lysine, cadaverine, and tyrosine precursors were the ones that showed the highest incorporation. Degradation experiments revealed that [1,5-¹⁴C]-cadaverine specifically labeled the piperidine ring of securinin and the radioactivity of DL-tyrosine-[2- ¹⁴C] was incorporated into the C-11 carbonyl of the lactone. Experiments with L-tyrosine[U-¹⁴C] and L-tyrosine-[3',5'-³H;U-¹⁴C] proves that the C₆ – C₂ fragment is derived from the aromatic ring and the C-2 and C-3 carbons of tyrosine.


(6S,11bS)-6,11b-Methane-3a,6,11a,11b- tetrahydrophire[2,3-c]pyride[1,2-a]azepine	Securinina	Secuamamine D	Filantidina	Securinega suffruticosa

Heterocycles formed by assembly

The phenylalanine anhydropeptides form 2.5-pirazinodium-type structures. These metabolites are widely distributed in mushrooms. Anhydropeptides can be diarylic (formed by a peptide condensation of two arilalanins, e.g. picrocceline, albonoursine, phenylalanin anhydride, cyclopenin, viridicatin, Piperafizina B, emeheterone.


Piperafizina B	Picroccelina B

Mixed anhydropeptides (formed from an arylalanine and another amino acid). For example, gliotoxin is formed from phenylalanine and serine:

Biosynthesis of gliotoxin

Several fungi (Arachniotus, Aspergillus, Epicoccum) can carry out other condensations and by means of a reverse electrocyclization of an arene epoxide, polycyclic alkaloids such as al aranotine are formed. In this case a second cyclization is carried out, in which a polycyclic compound is formed. Aranotine additionally undergoes reverse electrocyclization from the corresponding arene epoxide to form an oxepine system.

Biosynthesis of aranotin

Other heterocyclic arilalanine assembly systems are celloentered luciferins:


Coelenteramine	Coelenteramide	Coelenterazine	Medusa. Aequorea victory produces coelenteramide as a product of bioluminescence.

Nocardia is a genus of vancomycin producing bacteria.

Various modified amino acids are constituted by ribosomal and depsid peptides, such as vancomycin, thyrocidine and bauvericin:


Vancomicina	Tirocidina A	Beauvericina

Phenethylamines can be incorporated into rings of imidazoles (such as Polycarpine) and oxazoles, such as annuloline, halfordinol, texalin, and texamine:


Policarpina	Halfordinol

Common firefight (Lampyris noctiluca)

Simple phenols from arilalanin degradation can also be assembled without the formation of new carbon skeletons by intramolecular condensation, forming heterocycle systems with two heteroatoms. For example, the luciferin Lampyris noctiluca formed by this mechanism:

Biosynthesis of luciferin Lampyris

Isoquinoline alkaloids

The isoquinoline alkaloids and tetrahydroisoquinoline alkaloids (THIQ) comprise a diverse range of compounds widely distributed mainly in the plant kingdom. It should be noted that these isoquinolines have an alkyl substituent at position 1. Any other substitution pattern suggests another biosynthetic pathway. Biogenetically they can be formed by a Pictet-Spengler reaction of a catecholamine with an aldehyde or an α-ketocarboxylic acid:


1,2,3,4-Tetrahydroisoquinolin	THIQ Biosynthesis. La (S)-norcoclaurine sintasa EC:4.2.1.78 is the typical example of enzymes that catalyze this reaction, in this case from 3.4-dihydroxyphenylacetaldehyde (carbonyl) and dopamine (catecolamine).	PeyoteLophophora williamsii) Produces 1-alkyl-THIQ, where R = Me, H, iso-Bu, etc.	Poppy capsule (Papaver somniferum) Opium contains various alkaloids derived from 1-bencil-THIQ.	The plants of the genus Berberis produce Berberine-type alkaloids.

According to the aldehyde used, 4 large families of this type of alkaloids can be recognized:

(a) The simple isoquinolins, which are formed by condensation of a catecholamine with acetaldehyde, glioxal, piruvato, formaldehyde, etc.

(b) Bencilisoquinolins, which comprise the wider group of all are formed by condensing a catecholamine with a fenilacetaldehyde.

(d) The unsuccessful alkaloids, where the aldehyde is an iridoid.

Isoquinolins and tetrahydroisoquinolins simple: Isoquinolin isolates from the plant Spigelia anthelmia (Spigeliaceae). Several examples are anhalamine, anhalinine, iseluxine, calicotomine, laudanosine, coridaldine, salsoline, salsolidine, mimosamicin, renierona, talflavina, crispinas.


Gigantina	Lofoforina	Anhalamina	Dorianina	Iseluxina	Doryphora sassafras Isoquinoline-producing plant

The group of the saframicine and the renieramicina presents the structure of 6,15-epimino-4H-Ioquino[3,2-b][3]Benzazocina. Examples of these alkaloids are jorunamicins.

6,15-Epimino-4H-isochino[3,2-b][3]benzazocina

- Bencilchinolinic and bencilquinolynic alkaloids: They are formed by reaction of Pictet-Spengler of a catecholamine with phenylacetaldehydes, coming from the paths of phenylpropanoids. Examples of these alkaloids are papaverin, phylocriptine, phylocriptonine, velucriptine, papaveraldine, and dungeon. The herring and macrostomine, as well as its derivatives additionally have a pyrrolidinio ring attached to the aromatic ring.

Biosynthesis of benciltetrahydroisoquinolins


Papaverina	Arenina

- Alkaloids bisbencilisoquinolynics: They are produced by couplings of free radicals and are connected by one, two or three ether or biphenyl links. Monomeric units are mainly hydroxylated or metoxylated benzyles. Aporphine may contain aporphine components. This large group of alkaloids can be divided into five categories, according to the Shamma classification:

(a) Alkaloids that only present coupled arilo groups. From the bark Popowia floorcarpa a group of 7 alkaloids that have links between C-11 and C-11' have been isolated. Some examples are the pisopowetina and the pisopowiaridina.

Pisopowina

(b) Alkaloids containing only one ether link: Ether links are commonly found in C-11 and C-12' carbons, such as dauricin, C-11 and C-10', as in vanuatin, between C-10 and C-7' as malekulatin and ambrinine, C-11 and C-7', as in the nephenine.

Dauricina

(c) Alkaloids containing a link with an aromatic and one or two ether links. These alkaloids are based on the skeleton of the rodiasine, for example thiacorine.

Rodiasina

(d) Alkaloids containing 2 ether links: The largest simple subgroup containing two ether links has the berbamano skeleton, p. axim. berbamine. Another group of alkaloids are those of the oxiacanno type, such as oxiacantin, for example oxiacantin, which is connected in C-8 and C-7' carbons and between C-12 and C-13'. This group includes the talicberano (C-8 to C-6' and C-11 to C-12'), talidasano (C-8 to C-5¢ and C-11 to C-12'), and talmano (C-7 to C-5' and C-11 to C-12'). All these types contain links between benzyl rings and between the aromatic rings of the tetrahydroisocynolynic component. The hose contains ether links between the benzyl ring of one unit and the aromatic ring of the isochinoline component of the other unit.


Berbamano	Oxiacantano	Talicberano	Tubocurara

(e) Alkaloids with three ether links: These alkaloids include groups of 6'.7-epoxioxiacantano (p. axim.trilobine), 7.8'-epoxioxiacantano, and 8.12'-epoxitubocurarano.

- Pseudobencilisoquinolynic alkaloids: This term is used to describe an isobenzoquinolin skeleton in which a bencilisoquinolin skeleton in which the aromatic ring is oxygenated in the C-2', C-3' and C-4' carbon. These alkaloids come biogenetically from protoberynic salts by the C8-C8a link excision. Polycarpine, canadaline, Taxilamine and Ledecorina are examples of this type of alkaloids.

- Eyeline Alkaloids: Alkaloids derived from the cularine (12aS)-2,3,12,12a-Tetrahydro-6,9,10-trimetoxi-1-methyl-1H-[1]benzoxepino[2,3,4-ij]isoquinolin) are tetrahydroisochinolins containing an oxepin or dihydrooxepin merged between C-8 and C-2' carbons. They are formed by an intramolecular oxidative coupling. Examples are composteline, sarcocapnins, gouregine, aristoyagonine, aristocularins and cularine.

- Drycular Alkaloids: They can be classified into two groups, the B- and C-drycularins. An example of β-secocularins (e.g., sewcularine, and norsecocularin, which are structurally related to alkaloids derived from fenantreno derived from aporphine. C-secocularins (e.g. noyain).

- Canteen-type alkaloids: They are dimers of a cularine unit and a morphine through a spiro junction. They are found in species of the genus They say.

- Alkaloid type quetamine: Only three related compounds are known: Quetamine, Drychatamine and Dihydro-ecochetamine. These alkaloids are found in Berberis baluchistanica.


Cularina	Policarpina	Noyain	Pollution

- Pavin type alkaloids: These alkaloids are formed by alternative modes of oxidative cycling of benzoquinolynic precursors. P. example Pavina, Algerian.

-Alkaloid type amurensin: Amurensina


Amurensina	Pavina

- Benzopirrocolinas: Criptowolidina, criptowolinol, criptowolina.

- Proaporphin alkaloids: This alkaloid group represents an intermediate stage in the conversion of bencilisoquinolins into certain aporphins. Examples of these alkaloids are the orientalinone, glaziovina, stefarina, mecambrina, pronuciferin.

Proaporphine biosynthesis

- Apornic alkaloids:This large alkaloid group contains the apornic tetracyclic ring system (4)H- dibenzode,g]quinolin)formed by oxidative coupling of a phenol precursor bencilisoquinolin.

Biosynthesis of aporphine. Aporphine can be biosynthesized by transposition of proaporphine (1) and by radical coupling of a bencilisoquinolin (2).

Structural variations include:

(a) simple aporphins and dioxoloaporphins, for example glaucina, boldina, bulbocapnine, nantenin, hernandialin, nuciferin, liriodenine and pukatein. Laurotetamine, lauroscolzine, scoline, magnoflorin. Also included are usually unsaturated derivatives between C-6a and C-7 carbon.


Aporphine skeleton	Glaucina	Bulbocapnine	Nantenina

(b) apoporfinoid type duguenain and pancoridina. Its base skeleton is 9,10-dihydro-5H7H-benzof][1,3]dioxolo[6,7]isoquino[8,1,2-hij][3,1]benzoxazina.


Pancoridina	Duguena

(d) azafluorantenes (p. axim. rufescin and imelutein). They present the structure of indeno[1,2,3-ij]isoquinolina

(e) diazafluorants (p. axim. eupolauridina).

(f) 1-azaoxoaporfinoids (p. axim. sampangina). They present the skeleton of 7H-Nafto[1,2,3-ij][2,7]naftiridina.

(g) azahomoaporfinas (e.g. dredabine). It presents the structure of benzo[d]-1,3-dioxolo[4,5-g]pyrido[4,3,2-jk][2]benzazepina


7H-dibenzo(of,h)quinolin	Indeno[1,2,3-ij]isoquinolina	Eupolauridina	7H-Nafto[1,2,3-ij][2,7]naftiridina	Benzo[d]-1.3-dioxole[4,5-g]pyrido[4,3,2-jk][2]benzazepina

(h) oxidized aporfinoids (e.g. Andesine, chiloenin, santiagonamine).

(i) thropoloisochinolins (e.g. imerubrina). The base skeleton is 10H-blue[1,2,3-ij]isoquinolin.

(j) alkaloids type benzo[g]quinolin, for example cleistolin

(k) lennoxamine-type alkaloids (base skeleton: 5H-[1,3]dioxolo[4,5-h]isoindolo[1,2-b][3]benzazepina)

(l) alkaloids type 5H-Indeno[1,2-b]piridina, for example oniquina

(m) compounds in which heterocycle has been opened to give derivatives of fenantrenus, such as taspina.

(n) alkaloids containing 5-member lactamas rings, such as aristoctamas (such as cepharanone A) and piperolactama. Cephalons tienne as skeleton benzo[f]-1,3-benzodioxolo[6,5,4-cdIdol. Aristolic acid is a derivative of N nitro group oxidation.


Santiagonamina	10H-blue[1,2,3-ij]isoquinolin	Benzog]quinolina	5H-Indeno[1,2-b]piridina	Benzof]-1,3-benzodioxolo[6,5,4-cd]indol	5H-[1,3]dioxolo[4,5-h]isoindolo[1,2-b][3]benzazepina

Bencilisoquinolin-aporfina: They have a single ether link. A typical case is talicarpine.

- Limalongina

- Morphinal alkaloids: These alkaloids have as the basis skeleton of morphine. They are formed from the oxidative coupling of a hydroxylated isoquinolynic precursor. Some examples of this group are codeine, salutine, morphine and oripavina.

- Alkaloid type hasubanano: They form in a way similar to morphine. They isolated from the plant Stephania japonica Hasubanonine, cepharyamine, devalaine, glabradine, limalongine, longanine, longeterin, metaphanine, miersine, periglaucines A-D, prometafanine, prostephabisine, prostephanaberine, runanine, stefadynamine, stefamiersine, stephanine.

- Alkaloid type 7H- dibenzod.f]azonina: They isolated from the plant Stephania japonica. Protostephanine.


Hasubanano	7H- dibenzod.f]azonina

Alcaloides benzo[c]phenantridinics:

- Protoberinic alkaloids: They are tetracyclic alkaloids that have as a protoberine base skeleton. Examples of these alkaloids are anisocycline, palmatin, corlipalmine, discretamine, berlambine, lambertine, choreximine, talifaurine, coptisine, scoulerin, styling,

cavidin, cheilantifolin, corisolidin, coribulbin, coridalidzin, coridalin, coripalmin, corisamine, synactin, capaurimin. This group of alkaloids includes:

(a) tetrahydroprotoberins, for example tetrahydropalmatins.

(b) protoberines, such as Berberine;

(d) dryberries, which have a split ring. Some examples are aobamine, macrantaline and macrantoridine.

- Alkaloid protoxin type These alkaloids have the skeleton base bis[1,3]benzodioxole[4,5-c:5',6'-g]azecin Protopine, coricavamine, coricavidine, argemexicains A and B, constrictosin, cryptopin, pharmains I - III, muramine, pseudoprotoin.


bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecina

- Alkaloid type roeadina. The Roeadano ([1,3]dioxolo[4,5-h][1,3]dioxolo[7,8]-1H-isocromeno[3,4-a][3]benzazepina) is the base skeleton of these roeadina alkaloids, papaverubins, alpineigenin, glaucamine, zangezurina.


[1,3]dioxolo[4,5-h][1,3]dioxolo[7,8]-1H-isocromeno[3,4-a][3]benzazepina

- Alkaloids spirobencilisoquinolynics: They have as the base skeleton the 1.2-dihydrospiro[2-H-indeno-2,1'-isoquinolin], e.g. lahorin, africanine, coridaine, coristewartin, Smokingicin Smokingilinahyperectine, ocotensin, severzinine, radeanamine, radeanine.


1.2-dihydrospiro[2-H-indeno-2,1'-isoquinolin]

- Alcaloides benzo[c]fenantridínicos: They may have the basis skeleton [1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]fenantridine or the bis[1,3]benzodioxolo[5,6-a:4',5'-g]-4H-quinolizine, such as Quelidonine, sanguinarina, coridamine, arnotianamida, corinolamine, arnotianamida, quelilutina, corinolina. Dimeros: Sanguidimerina


Bis[1,3]benzodioxolo[5,6-a:4',5'-g]-4H- What?	[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]fenantridina

- Alkaloid type narcein. Bicuculinine, Peshawarina, narceine.

- Phalidoisocynolynic alkaloids: α-Hidrastine.

- Fenetylisocynolynic alkaloids

- Uniform alkaloids They have as skeleton base of the benzo[6,7]ciclohept[1,2,3-ij]isoquinolin, p.axism. kreysigina


Benzo[6,7]ciclohept[1,2,3-ij]isoquinolin

- Alkaloid type colchicin: They are amines of benzo derivatives[a]heptaleno, such as colchicin, O-Metilandrocimbina, autumnalina, alkaloid AM 3, colchiciline, colchifolin, cornigerin, lumicolchicinas, demecolcinona, spicesine.

- Alkaloid type homoeritrine: The homoeritrinano is a heterocycle with a base structure of [4,5-h]indolo[7a,1-a][2]benzazepine. Examples of these alkaloids are schelhammeridina, erimelantin, erisopinoforin, cefalofortunein, comosine, comosivine, dishomeritrina, fortunein, holidine, homoerisotin, isofelibilidina, lucidininine, felibilina.


[4,5-h]indolo[7a,1-a][2]benzazepina

- Dibenzocicloheptilaminas: These alkaloids have been found in plants of the genus Colchicum and Androcymbium. For example jerusalemine, salimina, alkaloid K4 and colchibiphenyline.

- Eritrean Alkaloids β-Erytroidine, Erisotramidina. Cephalotaxine presents a structure 4H-cyclopenta[a][1,3]dioxolo[4,5-hI'm sorry.b][3]benzazepina. Harringtonin and isoharringtonin.


Eritrean

Aaptamine-type alkaloids: Aaptamine and its natural congeners are marine alkaloids containing rings 4H-benzoof][1,6]-naftiridina. All aaptamines have been isolated from Demospongiae (Porifera). These alkaloids could be classified into the following groups:

- Aaptamine derivatives: for example aaptamine and isoaaptamine

- 1a,3,9-triazapirenos

- 8H-5,8-diazabenzo[cd]azulenos: For example aaptosin and aaptosamine.

- Dihouidine type

-Lamelarine-type alkaloids: The Lamelarinas are a family of pirrolo alkaloids[2,1-a]isoquinolynics related to the nuns, sneezeds and lukianoles. Biosynthetically they are bencilisoquinolynic alkaloids condensed with a phenylpropanoid. More than 30 related compounds and derivatives of the various lamelarins have been isolated. The A-D lamelarines were isolated by Andersen in 1985,

-Scientist alkaloids: Espiguetidina, dragabine.

There are various isochinolin oligomers such as repandulin, auroramine (p. axim. pennsylpavina and baluchistanamine) and other alkaloids such as epiberbivaldine and cancentrine.


Cancentrina	Auroramine	Repandulina

Alcaloides de Isopyrum: They are ethers of a THIQ and an aporphine, for example Isopirutaldina, isopitaldine and isotalmidine, talifin and isotalifin.

- Dry alkaloidsbencilisoquinolynics: They are those in which one of the units of bencilisoquinolin breaks between the C-1 carbon and the α carbon atom. Aldehyde lactams (such as Punjabine), lactam esters (gilgitin, talcamine) or aminoaldehydes (Jhelumina, chenabine). Karakoramine lacks the fragment of lactama, but it has a hydroxymethyl function in C'-aromatic carbon.


Karakoramina	Punjabine	Jhelimina

Aporfinoid numeralssuch as taliaberine, coyhaiquina and hernandaline. Roemeridina and Ourabaine.

Emethine type alkaloids: These alkaloids form a tetrahydroisocynolin unit from an iridoid aldehyde. The forerunner of these alkaloids is the ipecoside Emetina is the typical alkaloid of this group.

Alkaloid type ecteinascidine: Trabectidina, ecteinascidines

Phenanthroindolizidine and phenanthroquinolizidine alkaloids

- Fenantroindolizidinics and phenthhinokinolizidinic alkaloids: Tiloforin, Criptopleurine.

Norbeladin and mesembrenoid alkaloids

The Amaryllidaceae family produces a group of alkaloids whose precursor is norbeladin, an amine formed by the reduction of the Schiff base formed between protocatechuic aldehyde and tyramine. Norbeladin can couple the two aromatic rings it presents by free radicals. Thus, different structures can be formed according to the pattern of coupling of the rings. Norbeladin, cryptostilline I, cherillin, and nivalidin, galantamine, hemantidine, tazetin, and pancracin. Montanina. Lycorine, Lycorenine. Narcyclasine. Mainly there are skeletons type:

(a) Licorine

(b) Crinine

Mesembrenoid alkaloids are derived from two phenylalanine units with loss of one of the ethanamine side chains, which come from a lobeladin-type intermediate. This group of about 20 alkaloids has three structural types:

(a) Messembrin type: They have the 3a-phenoctahidro-1 base skeletonHMesembrine, mesembrol, crinafolidine.

(b) Joubertiamine Type: They form by the rupture of the indol ring, thus forming a linear amine.

(c) Tortuosamine type: The amine formed in the joubertamine type alkaloids recycles to form a structure type 6-phenyl-5,6,7,8-tetrahydroquinolin.

Dibenzoquinolizine and dibenzoindolizine alkaloids

It constitutes a small family of alkaloids that consist of an aromatic residue from an arylpropane derivative and a condensed cycle, probably formed as cylindrines. They have been isolated from the menispermaceous plants Cocculus hirsutus


Cohirsina	Cohirsitinine

Cytochalasins and Pseurotins

Cytochalasins are polyketide alkaloids that consist of an amide of the carboxylic end of the polyketide with the amino group of phenylalanine. Subsequently, this system condenses to form a pyrrolone and subsequently an intramolecular Diels Alder reaction occurs.

Pseurotins are spirofuropyrrolic polyketide alkaloids produced by a precursor polyketide that forms an amide with phenylalanine. Subsequently, the heterocyclization of pyrrole is formed and, finally, spirolactam with subsequent oxidations. Cephalimysins are alkaloids with biosynthesis related to pseurotins.

Cyclo-DOPA alkaloids

Dihydroxyphenylalanine (DOPA) can form 2,3-dihydroindole called cycloDOPA. This compound can form intermediate indoles. When this compound polymerizes, cyclizes, or condenses with cysteine, it forms eumelanins and pheomelanins.

Seco-DOPA alkaloids

Betalains. The basis of these alkaloid pigments is the betamic acidwhich is formed by the oxidative excision of the DOPA. When betalamic acid forms magnets with nitrogen of amino acids, they form betalains. They are classified into two types: Betacianins, which are iminous salts of the DOPA cycle, and the betaxanthins, which are magnets with amino acids or biogenic amines. These secondary metabolites of nitrogenated plants act as red and yellow pigments. They are present only in the Caryophyllales taxon except Caryophyllaceae and Molluginaceae (Clement) et al. 1994). In contrast, most other plants have pigments that are anthocyanins (which belong to the group of flavonoids). Betalains and anthocyanins are mutually exclusive, so when betalains are found on a plant, anthocyanins will be absent, and vice versa. Some fungi also present these compounds, called muscaaurines. When instead of forming a heterocyclus of six members (such as betamic acid) it forms one of seven, it is called muscaflavina, and the magnets are called higroaurines.

Alkaloids derived from anthranilate

Anthranilic acid is formed by concerted elimination with a nitrogen addition of glutamine from chorismic acid. This compound is the precursor of multiple secondary metabolites, which can be classified into the following categories:

(a) Protoalcaloids of anthranilate.
(b) Fenacious alkaloids
(c) Mixed polycytes with anthranic acid
(d) Corporal alkaloids
(e) Alcoholic alkaloids
(f) Alkaloids β-carbolinics
(g) Alkaloids of ergot
(h) Anhydropeptides of the tripptophan
(i) Numbers of tripptophan
(j) Quinine derivatives
(k) Chetoglobosan alkaloids

Anthranilate metabolites

Anthranilate Protoalkaloids

Protoalcaloids of anthranic acid: Damascus
Antitranyl acid (Bleniona), lilacinona
2HBenzoc]pirano[2,3-h]cinolinas: Necatorina

Phenazine alkaloids

Phenynazinic alkaloids: piocianine, aeruginos, emeralds.

Pyocyanin is a phenazine alkaloid that is one of the many toxins produced and secreted by the Gram-negative bacterium Pseudomonas aeruginosa. Pyocyanin is a blue-colored secondary metabolite with the ability to oxidize and reduce other molecules and thus can kill microbes that compete against P. aeruginosa as well as cells from the lungs of mammals to which P. aeruginosa has infected during cystic fibrosis. Chorismic acid is the precursor of pyocyanin, in which an amino intermediate is formed that, when assembled with two different tautomeric units, generates phenazine-1-carboxylic acid. This compound is a precursor to other phenazines.

Alkaloids 1,4-benzoxazin-3-ónicos: DIMBOA

Mixed polyketides with anthranilic acid

Quinolons and furo[2,3-b]chinolins: equinopsine, dictamnine, platidesmine, flindersin, eskimianin, cusparina
Acrydinic alkaloids: xantevodina, 4-hydroxy-2-quinolone, melicopicin, acronicine, routecridone.

Chindolinic Alkaloids: Criptolepina 10H-Indolo[3,2-b]quinolin (Quindolina), cryptospirolepin, cryptolepinas, isocriptolepin, neocriptolepin, hydroxycriptolepin, cryptoheptin, biscriptolepin, cryptomisrin, and chryptocyndoline.
Carbazlic alkaloids: murrayafolins, mukonin, koenolina, 3-methylcarbazole, clausins, 1-hydroxy-3-methylcarbazole, mukoeic acid, glycozomine, girinimbinol, furostifolina, clauszolinas, mahanimbinol, murrastifolins, carbazomicin, koen

Quinazoline alkaloids

Corporal alkaloids and pyrole[2,1-b]quinazolinas: Vasicina, luotonin, febrifuguina, triptoquivalin.Macrorina.

Dictioquinazoles
Benzodiazepinic alkaloids: Cyclopenin, viridicatin.

Indole alkaloids

Methyloxyl, methylbutin, melosatins, methophenyl, methodox, methylxine.

Pyrimidilindical Alkaloids: Meridianins, psamopemines, isomeridianins

Pyrroloindlic alkaloids: They are formed by heterocyclization of the tritamine to form 1.8-dihydropole[2,3-b]indoles such as Quimonantina, fisostigmina, flustramines.


1.8-dihydropirrole[2,3-b]indol

Necatarones


Necatarona

β-carboline alkaloids

Simple β-carbolins: They are formed by formaldehyde condensation, pyruvate, acetaldehyde, etc.

β--Carboline, Harmano, eleagnine, harmine, harmaline, Pseudofrinamines A, 5-Bromo-6-hydroxy-β-carboline, pseudofrinaminol, perlolyrine, borrerine, eudystomins, cantin-6-one, infractins, flazin, cantinones.

Picrasidins: Bis-β-carbolins produced by tritamine condensation with adipaldehyde.
Eudistomins: Alkaloid group that condense with cysteine isolated from tunicates:
Merged carbolins with anthranilate: Evodiamina


β-Carbolina	Harmina	Eudistomina C	Evodiamine

Alkaloids pyrrolo[4,3,2-ofCynolinics: Indoloquinones with intramolecular cycling of an imino link that form structures of pirrolo[4,3,2-ofChenolin. Examples: Makaluvaminas and micearrubinas. Bloodguinones have 2 other merged rings, just like hetatopodins


Pirrolo[4,3,2-ofChenolin, makaluvamine base structure	Sanguinona A	Hematopodina

Infractopicrines: Pentacyclic Alkaloids isolated from Cortinarius infracta.


Infractopicrin:

Indual alkaloids of Nitraria: They are formed by the condensation of a hydrolyzed piperidein ring from the lysine (Alkaloids β-carbolinmonopiperideinics) or with two piperidein units (Alkaloids β-carbolindipiperideinics). Examples of these alkaloids are nazlinine, schobericin, komaroidin, komavinas, nitrarin, nitramidine, nitraricine, nitrarizine, tangutorine, nitrarain, komarovina, komarovicin, komarovicin, komarovidina, isokomarovina, nitramarina

Strictosidinic alkaloids: Strictosidine

Camptotecin type alkaloids: They present rings of (1H4H,12H)-pirane[3',4':6,7]indolizino[1,2-bChenoline like Rubescina, camptotecina.


1H4H,12H)-pirane[3',4':6,7]indolizino[1,2-b]quinolina

Indoloquinolizidinic alkaloids: Angustin, Deplanchein


Angustina

Alkali type Corynanthe: Geissosquizina, sitsirikina, Ocrolifuanins, Usambarinas


Geissosquizina	Ocrolifuanine A

Ajmalicin-type alkaloids: Ajmalicin, oxayohimbano, corinantein


Corinano	Oxayohimbano	Ajmalicina

Oxyxinal alkaloids: Rincofiline, Formosanina

Alkaloids Gelsemium: Gelsedina, gelsemina

Alcaloides yohimbinoides: Yohimbina, reserpina, Alstonilina, rescinamine.

Alkaloids type Akuammilina: Akuammilina, equitamine, erypine, aspidodasicarpine, alstofiline, narelina,


Akuamilano	Macrolina

Sarpagine-type alkaloids: sarpagine, vobasin, gardneramine, evatamine, erythsine and koumine.


Sarpagano	Akuamidina	Ervatamine

Ajmalan alkaloids: Perakina, Raucaffrinolina, ajmalina

Pleiocarpamine type alkaloids: Pleiocarpamine

Five-type alkaloids: This alkaloid group includes antimalaric quinine, and contain a quinuclidine ring. This group is classified into two groups:

Quinine, cinchonamine (a) the cinchonamine group, derived from a corinanthine-type precursor by fission of N-4 to the C-5 bond, and by union of N-4 to C-17, (b) the quinine group, which contains a quinoline ring generated by fusion of the 2,7 bonds followed by an N-1 to C-5 fusion of the cinchonaminal.


Five	Quinina

Stricnine-type alkaloids: They are formed from akuammicin and suffer a later aldialic condensation with a coenzyme A acetyl unit. Some examples are Estricnidine, prekuamicin, brucina, estemadenine, estricnine.

Condilofolanic alkaloids: Condilocarpine, goniomine

Goniomine-type alkaloids: Goniomine

Dryedy alkaloids: Secodine and andranginin.

Ibogamine alkaloids: It consists of a series of alkaloids that come from the fission of the prekuamicin, where the stemadenine is formed and by reaction of Dielsa-Alder a new ring of ibogamine is formed.

Examples of these alkaloids are Cataranthine, coronaridine, tabernoxidine.


Ibogamine

Alkaloids aspidospermidinics: The skeleton of the aspidospermidian alkaloids is formed by the cyclization of dehydrosecodine, obtained from a precursor of dehydrosecodine.

Alkaloids in this group include the following structural variants:

(a) anilinoacrylic alkaloids, such as tabersonin, which contains the metoxycarbonyl group in carbon 16. The two carbon substitutes in position 20 can be a simple ethyl group, or can be functionalized.

Tabersonina

(b) alkaloids lacking the carbon 16 methoxycarbonyl group, as in aspidospermine. C-18 and C-19 can be an ethyl group or C-18, which can be functionalized.

(c) alkaloids containing an ether or lactone bridge between C-18 and C-21; (d) alkaloids containing an ether or lactone bridge between C-18 and C-15; (e) alkaloids containing a lactone bridge between C-18 and C-17, and a dihydro-1,4-oxazine ring between N-1 and C-12, as in obscurinervidin:


Obscurinervidina

(f) alkaloids containing an additional bond between C-18 and C-2, as in venalstonin;


Venalstonin

(g) alkaloids containing an additional bond between C-19 and C-2, as in vindolinine;


Vindolin

(h) the quebrachamine group, which is derived from the fission of the 7,21 bond. These alkaloids may have lost the C-16 methoxycarbonyl group, as in quebrachamine, or it may be retained, as in vincadine. Examples of these alkaloids are kopsiyunanins.


(+)-Quebrachamina	Vincadina

(i) Dimers such as vinblastine, vinorebine and vincristine. (V. Vinca alkaloids) (j) various alkaloids formed by a wide variety of processes, e.g. Ahem. aspidodispermine, banucin, vincatine, razinilama, trichophyllin, meloscin, melonin, goniomitin

Kopsan alkaloids: Kopsina, Fruticosine

Alkaloids type lapidilectin and lundurine.


Lapidilectina B	Lundurina B

Pandoline alkaloids: Pandolina, Cleavamina, Pandina, Iboxifilina, Ibofilidine

Pyridocarbazlic alkaloids: These alkaloids are formed by the excision of the estemadenin and by cycling on the ring of indol. Examples of these compounds are Olivacina, Elipticina, guatambuina, janetina

Ulein-dasicarpidan alkaloids: Ngouniensin, vallesamine, uleine

Conofilidine-type alkaloids.

Alkaloids Eburna: Eburnamina, cuanzina, Equizozigina, Andrangina and Vallesamidina

The skeleton of these alkaloids is generated by rearrangement of the aspidospermidine system, by migration of carbon 21 from carbon 7 to carbon 2, fission of bond 2,16 and by union of C-16 to N-1. These alkaloids can be classified into: (a) Vincamine and its derivatives, which retain the methoxycarbonyl group; (b) alkaloids such as eburnamine and eburnamenine, which have a loss of the ester group at C-22; (c) some derivatives where C-18 or C-19 are oxidized like quanzine; (d) The schizozygine group, which contains an additional bond between C-2 and C-18; (e) Related alkaloids andrangine and vallesamidine, where C-21 has migrated to C-2.


Eburnamenine

Alkaloid type manzamine

Ergot alkaloids and other indoleterpenes

Ergolin alkaloids: Chanoclavins, elimoclavine, cyclopiazonic acid, ergocristin, ergometrine, ergoclavine, clavictic acid, lysergy acid, ergine, agroclavine, paspalic acid, elimoclavine, ergocornin.

Alkaloid type Lolitrem: Lolitrem

Non-dulhispanic acid
Lolicinas

Alkaloids indolo[2,3-aCarbazlics:

Hapalindoles: Cyanophyta's isolated preniled idols.


Hapalindol A

Alkaloids AristoteliaAristotelina


Aristotelina

Alkaloids Borreria: Borrecapine, borrelina, borreverina.


Borrecapina

Alkaloid type notoamine

Tryptophan dimers

Staurosporin

Alkaloid type Caulerpa: Caulerpina
Alkaloids indoloflavonoids: Lotthanongina
Alkaloids type arciriaflavina and staurosporin
Butforamidines
Asterriquinonas

Alkaloids derived from kynurenine

Kynurenine, Xanthurenic acid, kynurenic acid, Orellanine

Phenoxazineic alkaloids: Cinabarin, cinnabarin acid, tramesanguina, polystictin, phenoxazone, α-aminophenoxazone. They are typical mushroom alkaloids Pycnoporus.

Dercytine-type alkaloids and cyclodercitin. Kuanoniaminas.

Tryptophan anhydropeptides

Anhydropeptides of tryptophan, spirodesmines, imidazoloids and Almazolonas: spirodesmines, Almazolones, equinuline, brevianamides, roquefortin, verruculgen, oxaline, indolactamas, sporidesmines, aranotin, hamacantins, espongoins, topsazixo, tardyna
Morfollinic indolyl alkaloids: oxazinins..
Alkaloid type 4-fenil-[2,7]-naftiridina: Some examples are lofocladines.

Ketoglobosan alkaloids

Chetoglobosan and related skeletons: Polycyte alkaloids with a stereotyphal unit and modified by a diels-Alder cycladdition. Includes Quetoglobinins, prochetoglobinins, isochetoglobinins, penocalasins and cytoglobinins.
Alanditripinona, Alantrifenona, Alantripineno, Alantrileunona

Alkaloids derived from histidine

Idiocese alkaloids

- Alkaloids derived from histidine: Histamine, uroconic acid, murexin, diphetamine, ergotionine

- Alkaloids of the Jaborandi: For example pilocarpine, dolicoteline and pilosine

Clatrodinic alkaloids

- Clatrodina type friends

- 6.8-dihidropirimido[4,5-c[3.2-e]azepinas: Latonduins

- Agelaspongin-type alkaloids and fakeline

- Alkaloid type agelastatin

- Numbers of clotrodines:

(a) Alkaloid type agelamida

(b) Alkaloid type ageliferina

(d) Alkaloid type stilisazol

(e) Macrophakeline:: For example palauamine, masadine, axinelamine and the styleguanidine.

Alkaloids derived from branched-chain amino acids

Pyrosles: Tenuazonic acid

Pirazinas: Asperegylic acid, flavacol, pulcherymic acid, neoasperectolic acid

Biosynthesis proposed for pulcherrymic acid

Sarcodoninas

Genalkaloids

Genalkaloids —or alkaloid amino oxides— are derived by oxidation from alkaloids that contain the group R=(NO)-R, where nitrogen has a valence V, as opposed to normal alkaloids, where it is trivalent (R =N-R). Its action is the same as that of the alkaloid from which they come, but it is slower. They are named by adding the prefix gen- to the name of the alkaloid.

Some genoalkaloids are found in nature, such as geneserine (derived from the alkaloid eserine (physostigmine)) present in the Calabar bean, as well as sarcoviolins and sarcodonins.

Pseudoalkaloids

Main article: Pseudoalcaloide

Pseudoalkaloids are secondary metabolites that have a nitrogen atom incorporated as ammonia into a biomolecule such as a terpene, polyketide, fatty acid, or shikimic acid derivative.

Chemotaxonomy

Alkaloids have been found in gymnosperms such as Cycas, Pinus, Ephedra and Podocarpus. Alkaloids have been isolated from many living systems other than plants, including bacteria, cnidarians, sponges, true fungi, vertebrates, and arthropods.

Alkaloids of bacteria and archaea

Class	Order	Families	Examples
Phylum Proteobacters
Beta Proteobacteria	Neisseriales	Family Neisseriaceae: Alkaloid type violacein (Chromobacterium)	Violace
Beta Proteobacteria	Burkholderiales	Family Oxalobacteraceae: Alkaloid type violacein (Janthinobacterium) Family Burkholderiaceae: Pirimidotriazines (Toxoflavina; Burkholderia)	Toxoflavina
Gamma Proteobacteria	Pseudomonadales	Pseudomonadaceae family: Phoenical alkaloidal pigments such as piocianinePseudomonas) Methylcholinenic alkaloids (Pseudomonas)	Piocianina
Gamma Proteobacteria	Enterobacterials	Family Enterobacteriaceae: Prodigiosine-type TrispiralsSerratia)	Prodigiosine
Delta Proteobacteria	Myxococcales	Family Polyangiaceae: Chivosazoles and epoilonasSorangium)	Epotilonas A (R = H) and B (R = CH₃)

Class	Order	Families	Examples
Phylum Cyanobacteria
Cyanophyceae	Nostocal	Family Nostocaceae: tropical alkaloids with lateral acetyl (Anatoxins; Anabaena, Aphanizomenon) Alkaloids triazaacenaphylénics (cylindrospermines; Cylindrospermopsis, Aphanizomenon)	Anatoxin A
	Oscillatorials	Noctuoid family: SaxitoxinsLyngbya) Polycyte (Curacinas, kalkitoxine; Lyngbya) Lingbiatoxins (Lingbiatoxins)Lyngbya). Family Phormidiaceae: tropical alkaloids with lateral acetyl (Anatoxins; Planktothrix)	Saxitoxin
	Stigonematales	Family Mastigocladaceae: Tetracyclic preniled indian alkaloids with the presence of issocianuros (Hapalindoles; Hapalosiphon)	Hapalindol A

Class	Order	Families	Examples
Phylum Actinobacteria
Actinobacteria	Actinomycetales	Pseudonocardiaceae family: Antisacarbamitocin type polycets (Amycolatopsis) AmicolamycinAmycolatopsis) Kibdelomicin (Kibdelosporangium) Family Actinomycetaceae: Pirimidotriazinas (Reumitsina; Actinomyces) Family Streptomycetaceae: Various antibiotic alkaloids have been isolated from various species of Streptomycessuch as: Mitomicines Nigrifactina Estreptimidona Estreptazolina Estreptotricines Duocarmicins Yatakemicin Pirazofurinas Indocromos Pirrolamas Estaurosporine and its derivatives Kikumicines Fredericamycin Piericidina Lagunamicina Lactimidomycin Estreptolidigine Geldanamicin Indanomicina Cafamicine Saframicines Gualamicina Nojirimicins Biciclomycin Lanopilins From Streptoverticillium Olivoretines have been isolated. Family Micromonosporaceae: Pyrrolo-ß-lactonic alkaloids (Salinosporamines; Salinospora) Dinemicines (Micromonospora). Family Nocardiaceae: Isocianuros indólicos (Brazilians; Nocardia) Family Actinoplanaceae: Simple indian alkaloids (Indolmycin, Chuangxinmycin; Actinoplanes)	Yatakemycina Mitomycin A Duocarmycin A Staurosporin Olivoretina E

Alkaloids isolated from algae and protozoa

Class	Order	Families	Examples
Phylum Dinoflagellata
Dinophyceae	Suessiales	Family Symbiodiniaceae Azaphenolic alkaloids (Simbioimins; Symbiodinium)	Simbioimina

Class	Order	Families	Examples
Phylum Rhodophyta
Florideophyceae	Ceramies	Family Rhodomelaceae: Pyrroles like the Kainic Acid (Alsidium) BromoindolesLaurencia) Pyrrolomydazlic alkaloids (Colensólidos; Osmundaria) Family Delesseriaceae: Oxazoles (Almazolona; Haraldiophyllum)	Almalo
Rhodophyceae	Ceramies	Family Delesseriaceae: Alcoholic alkaloids (Fragilamida, martensins; marshals, denticins; Martensia) Family Rhodomelaceae: Alcaloides 2,7-naftiridínicos (Lofocladinas; Lophocladia)	Lofocladina A

Class	Order	Families	Examples
Phylum Chlorophyta
Bryopsidophyceae	Bryopsidales	Family Caulerpaceae: Numbers of tripptophan (Caulerpina, caulersina; Caulerpa)	Caplergenic acid (caulerpina)
Ulvophyceae	Cladophorales	Cladophoraceae Family: BromobisindolesChaetomorpha)

Alkaloids isolated from fungi

Class	Order	Families	Examples
Phylum Mycetozoa
Myxogastria	Trichiida	Family Arcyriaceae: Numbers of tripptophan (Arciricianins, arciriaflavinas, arciroxocins; Arcyria)	Arciriaflavina A
	Liceida	Family Reticulariaceae: Numbers of tryptophan (Arciricianins, arciriaflavinas; Tubifera, Lycogala)
	Physarales	Family Physaraceae: Cinamamides of the tryptophan (Fuligo) Polycetides with anthranic acid as an initiation unit (Fisarigins; Physarum) Polycetalid compounds (Policephalins, physorubinic acid; Physarum) Family Didymiaceae: Indoloquinlic alkaloids (Makaluvamines; Didymium)

Class	Order	Families	Examples
Phylum Ascomycota
Saccharomycetes	Saccharomycetals	Family Saccharomycetaceae: Indoloquinazolynic alkaloids (Kingdainone, triptantrin; Candida) Pyrazinic alkaloids (pulcherrymic acid, Candida)
Sedis	Sedis	Pseudeurotiaceae Family: Spirofuropirrolone (Pseurotins; Pseudeurotium)
Dothideomycetes	Plenary	Family Pleosporaceae: Corporal alkaloids (Crisogine; Alternative) Pyrazopirroloindlic alkaloids (Sporidesmines; Alternative) Family Corynesporascaceae Pseudoalkaloid polyceted benzo[gIoquinolynics (Scorpinone; Corynespora) Family Sedis Pseudoalkaloid polyceted benzo[gChenolinics (Fomazarin, isoomazarin; Pyrenochaeta; Phoma)
Sordariomycetes	Hypocres	Clavicipitaceae Family: Prenilindrical alkaloids: ergoline alkaloids (Ergometrine, lysergic acid; Claviceps), lolitrem type (Neotyphodium). Epoxypirrolizidal Alkaloids (Lolinas, Epichloë). Pyrrolospirinic Alkaloids (Peramine, Neotyphidium) Pseudoalkaloids (Teneline; Beauveria). Family Ophiocordycipitaceae: Pseudoalkaloid benzoquinolynic polycets (Tolipocladine; Tolypocladium) Family Hypocreaceae Pirazinoid alkaloids (Gliotoxin, gliocládrido, gliocladine; Gliocladium) Pseudoalkaloid polycetides piperidinics (Awajanomicin; Acremonium)	Lolitrem B Lolina
	Sordariales	Family Chaetomiaceae: Pyrazoquinazolinanic alkaloids (Fiscalins; Corynascus) Chetoglobines (Chaetomium) Alkaloid imidazolo-α-carbolinics (Quetominins; Chaetomium)	Chetoglobosine A
	Xylariales	Xylariaceae Family: Citocalasins (Xylaria)	Citocalasina A
	Magnaporthales	Family Magnaportaceae: Pyrrolonic alkaloids (North-Nineanic acid; Pyricularia)
Eurotiomycetes	Chaetothyriales	Family Herpotrichiellaceae: Indolylcarbazlic alkaloids (Pitiriazol; Malassezia) Indolocarbalic alkaloids (Malasseziazoles; Malassezia)
	Euros	Family Trichocomaceae: Pyrazinoid anhydropeptides and their derivatives (Gliotoxin, asperectolic acid, triprostatins, azonazine, flavacol, micelianamide, nigerazines, nigragillin, bilains; Aspergillus, Penicillium) Corneral alkaloids (Triptoquivalins; notoamides, stefacidins, ardeemine, asperlicins, aurantin, aurantiomides, benzomalvinas, spirokinzoline, fumiquinazolinas, cotoquinazolina, trihistatin, quinadolins; Aspergillus, Penicillium) Pseudoalkaloid polycetic type talarotoxin (Talaromyces) Alkaloids α-carbolinics (Meleagrines; Penicillium) Pyrroloindlic alkaloids (Roquefortins, 'Penicillium) Sesquiterpenic alkaloids with a residue of piridine (Piripiropeno; Aspergillus) Males (Pencolido; Penicillium) Prenilindrical alkaloids with a succinimide system (cyclic acid; Penicillium) Indoloterpenic polycyclic alkaloids (β-aflatrem; aflavinine, paspalinin, paspaline, aflavazol, penitrem, jantitrem, shearinins; Aspergillus, Penicillium) Indolilterpenes (Emeniveol, tiersindoles; Emericella, Penicillium) Pirrolonas (Variotina; Paecilomyces) Alkaloids 4-phenolynics Viridicatin; Penicillium) Benzodiazepine alkaloids (Ciclopenin; Penicillium) Penicillins (Penicillium) Common-type alkaloids (a)Penicillium) Pseurotin alkaloids (Pseurotin alkaloids)Aspergillus) Alkaloids bisindolylquinónicos (Asterriquinones; Aspergillus) Iso-indlic steroid Pseudoalcaloids (Ergosterimida; Aspergillus) Family Nectriaceae: Pyrrolidinic alkaloids and tetromic acids (Nectrisin; NectriaRigidiusculamidas; Albonectria) Pyridinic alkaloids (Fusaric acid; Fusarium) Pyrroles formed by condensing of seine polycytes (Equisetin; Fusarium) Pseudoalkaloid polyceted benzo[gIisoquinolynics (Bostricoidine; Fusarium) Morfolinas (Lateritina; Fusarium) Family Elaphomycetaceae: Isoquinolynic polycetic Pseudoalkaloids (Monascorubramine, headingpunctamine; Monascus)	Asperegylic acid Gliotoxin Talarotoxine
	Onygenales	Family Onygenaceae: Polycyte Pseudoalkaloids with a Pyrrol Ring (Rumbrina, Auxarconjugatines; Auxarthron) Family Gymnoascaceae: Polycyte Pseudoalkaloids with a Pyrrol Ring (Rumbrina, Auxarconjugatines; Gymnoascus) Pyrazoindlic alkaloids (Aranotine; Arachniotus)
Arthoniomycetes	Arthoniales	Family Roccellaceae: Phenoxinal alkaloids (Orceins; Roccella)	α-Aminoorcein

Class	Order	Families	Examples
Phylum Basidiomycota
Agaricomycetes	Cantharellales	Family Ceratobasidiaceae: Indolizines without lateral chains (Eslaframina; Rhizoctonia)	Eslaframina
	Phallales	Family Phallaceae: Corneral alkaloids N-earlings (Dictyophora = Phallus; Dictioquinazoles)
	Russulales	Russulaceae Family: Benzocinonic alkaloids (Necatorine; Lactarius) Pyridinoacridinic alkaloids (Necatorone; Lactarius) Iso-indlic polycetic Pseudoalkaloids (Searrenins; Stereum) Family Hericiaceae: Iso-indlic geranylpolicete (Hericinininin); Hericium)	Necatorine
	Agaricales	Family Cortinariaceae: Infractopicin-type alkaloids (infractopicin-type)Cortinarius) Quinolinic alkaloids (Orellanin; Cortinarius) ß-Carbolins simple (Bruneins; Cortinarius) Piridine oxides (Cortamidine, orellanine; Cortinarius) Polyenics (Scauins; Cortinarius). Family Tricholomataceae: Indoles derived from lascivol (Tricholoma) Iso-indlic polycetic Pseudoalkaloids (Clitrines; Clitocybe) Isoxazolone (Tricolnomic acid; Tricholoma) Family Agaricaceae: Agaricona (Agaricona)Agaricus) Family Hymenogasteraceae: Alkaloids derived from tritamine (Beocistine, psilocin, psilocydone; Psilocybe). Amanitaceae Family: Isoxazoles and imidazolones (mustol, muscazona, ibotenic acid; Amanita) Betalains (Muscapurpurina, muscaaurines, miraxins; Amanita) Amavadina (a)Amanita) Family Hygrophoraceae: Azepinic pigments (Higrourinas, muscaflavina; Hygrocybe)	Infractopicrin Muscle (Panterina) Psilocy
	Cookies	Family Boletaceae: Pseudoalkaloids of polycetic origin (Chalciporin; Chalciporus) ß-Carbolinlactonas (Curtisins; Boletus) Polyenics (Boletocrocinas; Boletus) Beneficialtromic acids (Paquidermina; Chamonixia) Family Suillaceae: ß-Carbolins derived from 6-hydroxymethylfural (Flazine; Suillus) Family Mycenaceae: Pyrroloquinolynic alkaloids (Micenarubins, bloodthirs, hematopodines; Mycena)	Sanguinona A Hematopodina Paquidermina
	Polyporales	Family Meripilaceae: Quinolinic alkaloids (4-Hidroxi-2-methylpiridine; Physisporinus) Family Fomitopsidaceae: Polyenynic imidazlic alkaloid (Crisofisarin; Piptoporus) Family Polyporaceae: phenoxazineic alkaloids (acid cinabarin, picnoporin, cinabarin, tramesanguina; Pycnoporus) Pyridinic alkaloids (Trigonelin, homarine; Polyporus)	Cinnabarin acid
	Thelephorales	Family Bankeraceae: Pirazinobenzodioxazines (Sarcodonins, sarcoviolins; Sarcodon)

Alkaloids isolated from plants

Alkaloids are widely distributed in the plant kingdom (25% of plants contain alkaloids) and in some species their concentration can reach 10% (flowers). In the families Amaryllidaceae, Fabaceae, Liliaceae, Papaveraceae and Rutaceae, alkaloids have great chemotaxonomic value. The Solanaceae family is rich in alkaloids, but with differences at the genus level. Thus, in tobacco (Nicotiana) there are derivatives of pyridine (nicotine), in Solanum (potato, eggplant, tomato) there are spirosolane pseudoalkaloids (tomatine) and Datura, Hyoscyamus, Atropa and Scopolia contain tropane derivatives: hyoscyamine, atropine, etc.

Pyrrolizidines are found primarily in the families Compositae, Boraginaceae, Leguminosae, and Apocynaceae. The producing genera of these alkaloids are distributed in different regions and climates and could represent up to 3% of flowering plants. Some contain only one class of pyrrolizidine, but most contain between five and eight classes. The content varies with each species, but it can be a significant percentage of the dry weight. The highest concentration is found in the roots and is higher in young leaves, inflorescences and flower buds than in older leaves. In some species, high concentrations were found in seeds, which implies a risk in cases where these seeds are used for human consumption. There are N-oxides of these alkaloids, which are more soluble in water and are more easily transported within the plant.

Class	Order	Families	Examples
Phylum Pteridophyta
Pteridopsy	Polypodiales	Family Davalliaceae: flavonopiperidynic alkaloids (Davaliósidos; Davallia)	Davaliósidos

Class	Order	Families	Examples
Phyllum Lycopodiophyta
Lycopodiopsy	Lycopodials	Family Lycopodiaceae:: Alkaloids type licodina, liconadina and serratinin (Lycopodium) Family Huperziaceae: Huperzine-type alkaloidsHuperzia).	Licodina

Class	Order	Families	Example
Phyllum Pinophyta
Pinopsida	Pinales	Family Pinaceae: Pseudoalkaloids of polycytenic origin (Pinidina) Family Cephalotaxaceae: Alkaloid type cephalotaxane, such as haringtonin(Cephalotaxus).	Harringtonina.

Class	Order	Families	Example
Phyllum Gnetophyta
Gnetopsida	Ephedrales	Ephedraceae Family: Amines of the type of ephedrines have been isolated (Ephedramixed polyamines with spermidine and thyrosine (Ephedrarins; Ephedra).	Ephedrine.

Angiosperm plants:

Monocotyledonae (Liliopsyda;Cronquist): Many alkaloids from monocotyleon originate in phenylalanine and are exclusive to this taxonomic group, such as fenetylisocynolynic alkaloids and derivatives of norbeladine.

Order	Families	Examples
Phyllum Magnolophyta: Monocots Class (Clase Liliopsida; Cronquist)
Lilies	Family Liliaceae: Flavonopirrolidinic alkaloids (Lilacina; Lilium) Pyrrolidonic alkaloids (Bytrofam derivatives; Lilium) Family Colchicaceae: Alcaloides fenetiltetrahydroisoquinolynics and their derivatives (colchicina, androcimbina, isoandricimbina, kreysigine; Colchium, Androcymbium) Uniform Alkaloids (Schelhameridina, Schelhammera). Family Melanthiaceae: Pseudoalcaloid type cevano and veramatrano (Jervina, veratrine; Veratrum)	Schelhameridina Jervina
Shoot them.	Family Amaryllidaceae: Alkaloids derived from norbeladine (crinine, liquorine, galantamine, plicamine; crypowelins Galanthus) Arilindian alkaloids (Galantindol; Galanthus). Family Asparagaceae: Pyrrolizidinic alkaloids (Hiacinins, polygonatins; Hyacinthus; Polygonatum) Family Xanthorrhoeaceae: Pyrrolidinic alkaloids (Fulvanins; Hemerocallis)	Galantamine
Arecales	Family Arecaceae: Tetrahydrotinic acids (Arecoline, Areca)	Arecolina
Poales	Family Poaceae: (Anulolina; Lolium) Alkaloids benzoxazinoids and benzoxazólicos (Coix, Zea) Sesquiterpenic Pseudoalkaloids (Telepogine; Thelepogon)	Telepogina
Pandanales	Stemonaceae Family: Azepinedolic alkaloids (Stemona)	Tuberoestemonine
Orchidales	Family Orchidaceae: Pyrimidinic Alkaloids (1-cinamoil-2-acetonylpyrimidins) (Dendrocrisanins; Dendrobium) Pyrrolizidinic alkaloids (Plenopsins; Phalaenopsis) Isatins (Calanthe)	trans-Dendrocrisanine.
Alismatales	Family Zosteraceae: Alkaloids flavonopirrolidinics (Filospadina; Phyllospadix) Family Araceae: Alkaloid alkylpirrolidinics (Irniin); Arisarum)	Irnidine
Goals	Familia Dioscoreaceae: Alkaloid type godcorina (Godcore.).	Godcorina

Subclase (Cronquist)	Orden	Familias	Ejemplos
Phyllum Magnolophyta: Clado Eudicots (Clase Magnolopsida; Cronquist)
Magnoliidae	Nymphaeales	Familia Nymphaeaceae: Pseudoalcaloides monoterpénicos tipo nufaridina (Nuphar)	Nufaridina
	Piperales	Familia Piperaceae: 1-Acilpiperidinas y 1-acilpirrolidinas (Piperina, chabamina, braquiamidas; Piper) Alcaloides dibenzo[cd,f]indólicos (Piperolactamas; Piper) Familia Saururaceae: Alcaloides dibenzo[cd,f]indólicos (Sauristolactama, Saururus)	Piperina
	Aristolochiales	Familia Aristolochiaceae: Alcaloides dibenzo[cd,f]indólicos (Aristolactamas, Aristolochia) Nitroantracenos (Ácido aristolóquico; Aristolochia).	Ácido aristolóquico
	Laurales	Familia Calycanthaceae: Alcaloides dímeros de pirroloindoles (Quimonantina; Chimonanthus). Familia Hernandiaceae: Éteres de alcaloides bis tetrahidroisoquinolínicos (Vanuatina, malekulatina; Hernandia) y aporfínicos (Hernandialina; Hernandia) Familia Atherospermataceae Alcaloides 1-oxoisoquinolínicos (Dorisporfina, Doryphora)	Vanuatina
	Magnoliales	Familia Magnoliaceae: Alcaloides indenonaftiridínicos (Eupolauridina; Eupomatia) Familia Annonaceae: Alcaloides indenonaftiridínicos y sus óxidos (Eupolauridina; Cleistopholis, Cananga) Alcaloides tipo sampangina (Sampangina, eupomatidinas; Cananga, Ambavia) Éteres bisbenciltetrahidroisoquinolínicos tipo pisopowina (Pisopowina, pisopowetina; Popowia) Alcaloides cularínicos dimetilados (Gouregina; Guatteria), Alcaloides azahomoaporfínicos (Espiguetidina, Duguetia, Guatteria, Meiogyne) Alcaloides azafluorénicos (Oniquina, dielsinol, oxilopidina, ciatocalina, ursulina, Onychopetalum, Cleistopholis, Guatteria, Polyalthia, Oxandra, Unonopsis, Piptostigma, Alphonsea, Mitrephora, Meiogyne, Cyathocalyx, Oncodostigma) Bisaporfinas (Urabaína; Piptostigma, Oxandra, Polyalthia) Familia Himantandraceae: Pseudoalcaloides pirrolidínicos de origen policétido (Himbacina; Galbulimima) Familia Myristicaceae: Alcaloides espiroxindoles (horsfilina; Horsfieldia) Alcaloides dibenzo[cd,f]indólicos (Aristolactamas, Schefferomitra) Alcaloides benzo[g]quinolínicos (Annofolina, griffithazanonas, kalasinamida, cleistofolina; Annona, Goniothalamus, Polyalthia, Cananga, Meiogyne, Oncodostigma, Porcelia)	Eupolauridina Espiguetidina Oniquina
Ranunculidae (Cronquist)	Ranunculales	Familia Ranunculaceae: Pseudoalcaloides sesquiterpénicos tipo aconitano y atisano (Aconitina; Aconitum, Delphinium, Consolida) Alcaloides aporfínicos (Corituberina; Coptis) Éteres aporfino-tetrahidroisoquinolínicos (Talifarapina; Thalictrum) Dímeros bisbencilisoquinolínicos (Isopirutaldina, isopitaldina, isotalmidina Isopyrum) Alcaloides piradizinoindazólicos (Nigeglanina, Nigellicina, Nigellidina; Nigella) Alcaloides flavonodiazepínicos (Aquiledina, isoaquiledina; Aquilegia) Familia Berberidaceae: Alcaloides berberínicos (Berberina; Berberis) Alcaloides benciltetrahidroisoquinolínicos (Taxilamina, Berberis) Alcaloides con enlaces monoéter bis-benciltetrahidroisoquinolínico (Berbamunina, canadina, curacautina); Berberis, Mahonia) Éteres tetrahidroisoquinolin-orientalinónicos (Pakistanamina; Berberis) Familia Menispermaceae: Alcaloides tipo diéter bis-benciltetrahidroisoquinolínico (Tetrandrina, tubocurarina; Stephania, Chondrodendron) Alcaloides aporfínicos (Estefanina; Stephania) Alcaloides oxaisoaporfínicos (Menisporfina;Menispermum) Alcaloides azuleno[1,2,3-ij]isoquinolínicos (Grandirubina, imerubrina, Abuta, Cissampelos) Alcaloides indeno[1,2,3-ij]isoquinolínicos (Imeluteína, rufescina, triclisina, telitoxina; Abuta, Cissampelos, Triclisia, Telitoxicum) Secoalcaloides tipo taspina (Caulophyllum)	Aconitina Berberina Menisporfina Rufescina
Ranunculidae (Cronquist)	Papaverales	Familia Papaveraceae (incluye ant. fam. Fumariaceae): Alcaloides benciltetrahidroisoquinolínicos (Papaverina, reticulina, arenina; Papaver) Alcaloides del morfinano (Morfina, salutarina; Papaver) Alcaloides aporfínicos (Papaver) Alcaloides dibenzoazocínicos (Protopina; Chelidonium) Alcaloides ftálido-tetrahidroisoquinolínicos (Hidrastina; Hydrastis) Alcaloides secoaporfínicos (Narceína, Papaver) Alcaloides secoprotoberberínicos (Canadalina, argenaxina, ledecorina; Corydalis, Hydrastis, Argemone, Fumaria) Alcaloides cularínicos (Cularinas; subfam. Fumarioideae: Corydalis, Dicentra, Ceratocapnos, Sarcocapnos) Alcaloides aristocularínicos (Aristoyagonina; Sarcocapnos) Alcaloides heptacíclicos proaporfino-triptamínicos (Roehibridina; Roemeria, Phoebe) Alcaloides tipo aspidospermina (Eburenina; Amsonia, Aspidosperma, Rhazya)	Papaverina Morfina Protopina
Caryophyllidae (Cronquist): Todas producen betalaínas en lugar de antocianinas.	Caryophyllales	Familia Cactaceae: Tetrahidroisoquinolinas simples (Anhalamina, lofocerina; Lophophora) Familia Ancistrocladaceae: Pseudoalcaloides policétidos bisnaftilisoquinolínicos (Michelamidas, ancistrocladinas, korupensaminas; Ancistrocladus) Familia Amaranthaceae: Alcaloides β-carbolínicos simples y tipo cantinona. (Aerva) Alcaloides tripiperidínicos (Anabasamina; Anabasis) Familia Polygonaceae: Alcaloides piperidínicos (Fagomina, Fagopyrum) Alcaloides indoloquinazolínicos (Triptantrina; Polygonum)	Anhalamina
Dileniidae (Cronquist)	Cucurbitales	Familia Cucurbitaceae: Pirazoles (ß-Pirazol-1-ilalanina; Citrullus)	L-β-Pirazol-1-ilalanina
	Ericales	Familia Theaceae: Alcaloides purínicos (Teofilina; Camellia) Familia Lecythidaceae: Isatinas (Couroupita) Familia Actinidiaceae Pseudoalcaloides iridoides piridínicos (Actinidina; Actinidia)
	Brassicales	Familia Caricaceae Alcaloides piperidínicos bislactónicos tipo carpaína (Carica) Familia Capparaceae: Alcaloides macrocíclicos derivados de la espermina (Capparispina, cadabicina; Capparis) Familia Brassicaceae: Macrociclos de la espermina (Lunarina; Lunaria) Éteres imidazolilmetilfenólicos (Lepidinas; Lepidium) Oxazolidinas (Progoitrina; Brassica) Aductos del triptófano con el ácido ascórbico (Ascorbígenos; Brassica) Fitoalexinas, glucosinolatos indólicos y compuestos relacionados (Glucobrassicina, ditireanitrilo, camalexina; Dithyrea, Arabidopsis, Camelina) Isatinas (Isatis Familia Salvadoraceae: Índoles (Salvadoricina; Salvadora)	Lunarina Ascorbígeno
	Malvales	Familia Malvaceae: Pirroles (Funebrina; Quararibea)
Hamamelidae	Daphniphyllales	Familia Daphniphyllaceae: Pseudoalcaloides tipo dafnifilina, calidafninona y yuzirimina (Daphniphyllum)
Hamamelidae	Fagales	Familia Fagaceae: Alcaloides indolizinquinolínicos (Chesnutamida; Castanea) Familia Casuarinaceae: Alcaloides pirrolizidínicos polihidroxilados (Casuarina; Casuarina)
Rosidae (Cronquist)	Malpighiales	Familia Phyllanthaceae: Alcaloides tipo securinina (Securinina, filantidina; Securinega, Breynia) Alcaloides bispiperidínicos (Astrofilina; Astrocasia) Alcaloides pirido[2,1-a][2]benzazepínicos (Astrocasina; Astrocasia) Alcaloides tipo poranterina (Poranterina, porantericina; Poranthera) Pseudoalcaloides lipídicos piperidínicos (Andraccinidina, Aspertinas; Andrachne) Familia Salicaceae: Ésteres diterpénicos del ácido pirrolocarboxílico (Ryanodina; Ryania) Alcaloides diazocínicos (Homalina; Homalium) Familia Rhizophoraceae: Alcaloides pirrolidindiil-bis-1,2-ditiolánicos (Gerrardina; Cassipourea) Alcaloides pirrrolizidínicos con puentes disulfuro (Casipurina; Cassipourea) Alcaloides tropánicos (Brugina; Bruguiera, Crossostylis)	Securinina Astrofilina Gerrardina
	Celastrales	Familia Celastraceae Ésteres y lactonas del ácido evonínico (maytolina, maytina, acantotamina, evonina, neoevonina, euonimina, hipocratinas, emarginatinas; Maytenus, Hippocratea)	Macrolactonas del ácido evonínico
	Fabales	Familia Fabaceae: Alcaloides pirrólicos (Pisatósido; Pisum) Alcaloides bispiperidínicos (Histrina, virgidivarina, isoamodendrina y sus derivados, jusiaeínas; Genista, Ammodendron, Dichilus, Spartidium, Lupìnus, Sophora, Coelidium, Ammopiptanthus, Thermopsis, Castilleja, Virgilia) e indolmetil bispiperidínicos (Gramodendrina; Lupinus, Ulex) Diversos alcaloides derivados de la lisina, sobre todo aquellos con varios anillos de piperidina fusionados, como la quinolizidina y la esparteína. (Lupinina, matrina, esparteína, citisina, ormosamina, angustifolina; Lupinus, Ormosia, Thermopsis, Calia, Cytisus, Baptisia, Genista, Pelargonium, Sophora, Laburnum, Ammodendron, Virgilia) Alcaloides pirimidínicos (Latirina, vicina; Lathyrus, Vicia) Alcaloides indolizidínicos provenientes del ácido pipecólico (Swainsonina, castanospermina; Swainsona, Castanospermum) Alcaloides pirroloindólicos y furoindólicos simples (Fisostigmina, fisovenina; Physostigma. Yuremamina; Mimosa) Pigmentos bisindólicos (indigotina; Indigofera) Alcaloides eritrinánicos (Eritralina; Erythrina) Alcaloides 2,7-naftiridínicos (Sesbanina, Sesbania) Glutanimidas (Sesbanidina, Sesbania). El imidazol en forma libre se encuentra en varias semillas de leguminosas (Lens, Adenanthera, Amphimas, Cathormion, Erythrophleum, Lathyrus, Macrotyloma, Parkia, Psophocarpus, Tephrosia, Vigna); alcaloides piranoquinolínicos (Cassiarinas; Cassia) Sales de amonio de aminoácidos (Trigonelina; Trigonella) Alcaloides cromanoimidazólicos (Cassiadinina; Cassia) Alcaloides piperidinilalquilindolizínicos (Juliflorina; Prosopis)	Ormosamina Angustifolina Latirina Fisostigmina Trigonelina Gramodendrina
	Proteales	Familia Elaeagnaceae: Alcaloides ß-carbolínicos simples (Eleagnina, Elaeagnus) Familia Nelumbonaceae: Éteres bistetrahidroisoquinolínicos (Neferina, liensinina; Nelumbo) Familia Proteaceae Alcaloides ariltropánicos (Knightolina, knightolamina, knightalbinol, estrobamina, chalcostrobamina, darlingina, Ferrugina; Knightia, Darlingia, Triunia) y piranotropánicos (Belendina; Bellendena)	Neferina Chalcostrobamina
	Rosales	Familia Moraceae: Alcaloides flavonopirrolidínicos (Ficina, isofocina; Ficus) Alcaloides indolizínicos polihidroxilados (Brousonetinas; Broussonetia) Alcaloides fenantroindolizínicos (Ficuseptinas, tilocrebrinas; tiloforinas) Alcaloides alquilpirrolidínicos (Brousonetinas; Broussonetia, Ácidos morusímicos; Morus) Familia Urticaceae: Alcaloides fenantroquinolizínicos (Criptopleurina; Boehmeria) Familia Crassulaceae Alcaloides dialquilpiperidínicos (Sedacriptina, sederina, sedinona, homosedinonas y dihomosedinonas; Sedum)	Broussonetinina A Criptopleurina Sedacriptina
	Cornales	Familia Nyssaceae: Alcaloides indolizinoquinolínicos (Camptotecina; Camptotheca) Familia Hydrangeaceae: Alcaloides acetonilquinazolínicos (Febrifugina; Dichroa, Hydrangea) Familia Alangiaceae: Alcaloides tipo emetina (Cefaelina, alangísido; Alangium)	Camptotecina
	Zygophyllales	Familia Zygophyllaceae: Alcaloides ß-carbolínicos simples (Harmina; Peganum) Alcaloides pirroloquinazolínicos (Peganina; Peganum)	Harmina
	Oxalidales	Familia Elaeocarpaceae: Alcaloides ß-carbolínicos (Eleocarpidina; Elaeocarpus) Alcaloides indolizínicos (Eleocarpina, grandisinas, eleokanidinas, eleokanidinas, Elaeocarpus) Alcaloides indoloterpénicos tipo aristotelina, serratolina, tasmanina y sorelina (Aristotelia)	Aristotelina Eleocarpina
	Sapindales	Familia Rutaceae: Alcaloides furoquinolínicos y piranoquinolínicos (Dictamnina, eskimianina; arborina, euxiloforicinas, paraensina, flindersina; Dictamnus, Skimmia, Glycosmis, Euxylophora, Flindersia, Fagara, Haplophyllum) Alcaloides ß-carbolinquinazolínicos (Rutecarpinas, evodiaminas, hortiamina; Euodia, Hortia) Alcaloides acridínicos (Melicopicina, rutacridona, acronicina, tegerrardinas, vebilocina; acridona, acrimarinas; Melicope, Ruta, Acronychia, Citrus, Teclea, Fagara, Glycosmis, Esenbeckia, Acronychia, Oricia, Vepris, Boronia, Boenninghausenia, Thamnosma) Alcaloides imidazólicos producto de condensación con aminoácidos (Pilocarpina, pilosina; Pilocarpus) Alcaloides piridinilfenil oxazoles (Halfordinol, texalina; Halfordia, Triphasia, Aegle, Amyris) Alcaloides carbazólicos simples (Murrayafolinas, clausinas, ácido mukoénico, girinimbina, clauszolinas, mahanimbinol, murrastifolinas, murrayazolinina, murrayaminas, murrayakoeninol, eustifolinas, pirayafolinas; claurailas, pirayaquinonas, crestifolinas; Murraya, Clausena, Glycosmis) Alcaloides tipo cantinona (Phellodendron) Alcaloides quinolínicos (Cusparina; Angostura). Alcaloides cromanopiperidínicos (Schumannioficina, Schumanniophyton) Familia Meliaceae: Alcaloides cromanopiperidínicos (Rohitukina, crotacuminas; Amoora, Dysoxylum) Familia Simaroubaceae: Alcaloides ß-carbolínicos simples y (2-hidroxietil)-ß-carbolínicos (Picrasidinas; Picrasma) Alcaloides tipo cantinona (Hannoa, Quassia); alcaloides oxaazafenantrénicos (Flindersina, Toddalia) Familia Nitrariaceae: Alcaloides polipirrolidínicos (Nitramina, nitrabirina, nitraramina, schoberina,; Nitraria) Alcaloides quinolínicos (Sibiridina; Nitraria), ß-carbolinas monopiperidínicas (Nazlinina, komaroidina, komavina; Nitraria) Alcaloides quinazolínicos (Wuchuyuamidas; Eudia).	Pilocarpina Cusparina Dictamnina Rutacridona Rohitukina
	Euphorbiales	Familia Buxaceae: Aminas esteroidales de Buxus (Buxadienina, buxacuamarina). Familia Euphorbiaceae: Alcaloides tipo cianopiridinas (Ricinina, hermidina; Ricinus, Mercurialis) Azabiciclo[3.3.1]nonanos (Eufoccina; Euphorbia) Alcaloides pirimidínicos (Andraccina, aspertinas; Andrachne) Alcaloides flavonoindólicos (Lotanongina; Trigonostemon) Alcaloides pirrolidónicos (Derivados del jatrofam; Jatropha) Glutarimidas (Julocrotina y sus derivados; Julocroton, Croton)	Astrocasina Julocrotina
	Myrtales	Familia Lythraceae: La granada contiene alcaloides tipo pseudopeletierina y piperidínicos (Peletierina) Alcaloides ciclofánicos con quinolizidinas o piperidinas (decalina, litrancina, litranidina; Lythrum) Alcaloides piperidínicos fenilbutílicos (Soneratina A; Sonneratia) Familia Combretaceae: Alcaloides flavonopiperidínicos (Capitavina, buchenavianina; Buchenavia) Familia Vochysiaceae Alcaloides cromanopirrolidínicos (Vochisina; Vochysia)	Soneratina A
	Apiales	Familia Apiaceae: Pseudoalcaloides piperidínicos de origen lipídico (Coniína, Conium). Alcaloides pirrolidónicos (Divaricataester A; Saposhnikovia) Familia Vochysiaceae: Alcaloides flavonopirrolidínicos (Voquisina; Vochysia)	Coniina
Asteridae (Cronquist):	Solanales	Familia Convolvulaceae: Alcaloides acetonilpirrolidínicos (Higrina) y tropánicos con un carboxilo lateral (Cocaína, metilecgonina, truxilinas de la planta de coca, Erythroxylum coca), otros alcaloides tropánicos (Calisteginas, merresectinas, bonabilinas, consiculina, anisodamina, convolvidina, convolvina, confolina, merresectinas, mooniina, subhirsina; Calystegia, Merremia, Bonamia, Convolvulus, Evolvulus, Przewalskia, Physochlaina, Anthocercis, Physalis) Alcaloides indolizínicos (Swainsonina, Ipalbidina, Ipalbina; Ipomea). Familia Solanaceae: Pseudoalcaloides espirosolánicos y solaninas (Tomate y patata, Tomatidina) Alcaloides tropánicos sin carboxilo lateral (p. ejem. hiosciamina, apohioscina, belladonina, litorina, atropina, apoatropina, escopolamina, calisteginas, anisodina, grahamina, litorina, esquizantina; Hyosciamus, Anthocercis, Atropa, Mandragora, Scopolia, Lycium, Nicandra, Datura, Duboisia, Anisodus, Physochlaina, Anisodus, Orobanche, Schizanthus) Alcaloides pirrolidinilpiridínicos (Nicotina; Nicotiana) Acetonilpiperidinas (Anaferina; Withania) Alcaloides quinoxalínicos (Baimantuoluoamidas; Datura)	Cocaína α-Solanina Nicotina Anaferina
	Asterales	Familia Asteraceae: Alcaloides pirrolizidínicos (Senecio) Cotuzinas (Cotula) Alcaloides quinazolínicos (Equinosolinona; Echinops) Familia Campanulaceae: Alcaloides piperidínicos con fenetilos laterales en la posición 2,6 (Lobelina, Lobelia, Hippobroma, Dialypetalum, Siphocampylus) Alcaloides furil-β-carbolínicos (Perlolirina; Codonopsis) Morfolinas (Ácido codopiloico; Codonopsis)	Lobelina Cotuzinas
	Lamiales	Familia Boraginaceae: Alcaloides pirrolizidínicos (Equimidina; Heliotropium, Cynoglossum, Symphytum). Familia Acanthaceae: Alcaloides quinazolínicos (Vasicina, Vasicinona; Justicia) Poliaminas mixtas de cadaverina-tirosina (Afelandrina; Aphelandra) Alcaloides quinindolínicos (Quinindolina; Justicia) Familia Bignoniaceae: Pseudoalcaloides iridoides (Incarvilina, incarvinas, kinabalurinas, tecostanina, tecomina, boschniadina; Incarvillea, Tecoma) Alcaloides pirrolobenzofuránicos (Millingtonina; Millingtonia) Familia lamiaceae: Betaínas de la prolina (Estaquidrina, Stachys, Leonurus) Alcaloides flavono pirrolidínicos (Dracocefinas; Dracocephalum)	Estaquidrina
	Gentianales	Familia Loganiaceae: Quinolina (Spigelia) ß-carbolinas simples (Normelinonina F; Strychnos) Alcaloides benzocarbolínicos (Criptolepina, isocriptolepina, biscriptolepina, criptomisrina, criptoquindolina; Cryptolepis) Alcaloides quinindolínicos (Neocriptolepina; Cryptolepis Alcaloides tipo estricnano (Brucina, estricnina, toxiferinas; Strychnos) Familia Gentianaceae: Pseudoalcaloides piridínicos de origen iridoide (Gentiopicrósido, gentianina; Gentiana) Familia Apocynaceae: Esta familia representa uno de los grupos más importantes en lo que a diversidad de alcaloides concierne: Alcaloides de la vinca (Reserpina, vinblastina; Rauwolfia, Vinca) Alcaloides tipo Iboga (Ibogaína, vellosimina; Tabernanthe, Rauwolfia) Alcaloides 6H-pirido[4,3-b]carbazólicos (Elipticina; Ochrosia) Pseudoalcaloides piperidínicos de origen iridoide (Eskitantinas; Skytanthus) Purpelinas (Rauwolfia) Alcaloides piperidiniletilindólicos (Crooksidina; Haplophyton) Alcaloides del kopsano (Kopsina; Kopsia) Alcaloides azabiciclononánicos (Kopsona; Kopsia) Alcaloides tipo lundurina (Kopsia) Alcaloides flavonopiperidínicos (Kopsiraquina; Kopsia) Alcaloides fenantroindolizínicos (Antifinas; Vincetoxicum) Alcaloides difenilindolizínicos (Septicina; Tylophora) Alcaloides tipo pleiocarpamina (Alstonia) Alcaloides pirroloindólicos condensados con terpenos tipo abereamina (Abereaminas; Hunteria) Alcaloides piperidilindólicos (Angusilobinas, vallesamina, tubotaiwina; Alstonia) Alcaloides tipo conofilidina (Tabernaemontana) Alcaloides tipo aspidospermina (Modestanina; Tabernaemontana) Alcaloides polipiperidínicos Mirioneurinol, mirioxazinas, mirobotinol; Myrioneuron) Alcaloides indoliletilpiridinioicos (Ikiridinios; Hunteria) Alcaloides piperidinilmetilindólicos (Manilamina; angustilobinas; Alstonia) Alcaloides β-carbolínicos condensados con secologanina (Lialósido; Palicourea) Familia Rubiaceae: Alcaloides espiroindolindolizínicos (Rincofilina, uncarinas, corinoxina, rotundifolina; Uncaria) Alcaloides iridotetrahidroisoquinolínicos tipo bahienósidos, ipecósido, emetina (Psychotria) Alcaloides ß-carbolínicos tipo Corynanthe (Ajmalina, akuamicina, yohimbina, alstomacrofilina, alstomacrolina, alstonerina, alstofilina, macrocarpamina, alstoumerina, lercheína; Pausinystalia, Alstonia, Lerchea) Alcaloides benzo[g]isoquinolínicos (Biquidona; Mitracarpus, Psychotria) Alcaloides quinuclidínicos (Alcaloides de la quina, como la quinina; Cinchona) Alcaloides purínicos (Cafeína, Coffea) Alcaloides terpeniloxindólicos y terpenilindólicos (Laugerina, borrecapina; Guettarda, Borreria) Familia Gelsemiaceae: Alcaloides tipo gelsemina, gelsemamida, gardanerina y gelsemoxonina (Gelsemium) Alcaloides tipo mostueína (Mostuea)	Cafeína Reserpina Ibogaína Elipticina Conofilidina Vinblastina

Alkaloids isolated from animals

Class	Order	Families	Examples
Phylum Porifera
Demospongiae	Hadromerida	Family Suberitidae: Naphtamine alkaloids (Aaptamine and its derivatives; Aaptos) Family Trachycladidae Imidazolindoles (Traquicladindol; Trachycladus)	Aaptamine
	Haploscleride	Petrosiidae Family: Pseudoalcaloid type ingenamine and manzamine-type alkaloidsXestospongia) Azacicloalcans conjugated with polyamines type sperm (Motuporamins; Xestospongia) Pseudoalcaloides lipidic type madangamine (Xestospongia). Pseudoalcaloid lipids type xestospongin and petrosine (Xestonpongia, Petrosia) Callyspongiidae Family: Pseudoalcaloid lipidic type arenosclerina (Arenosclera) Chalinidae Family: Alkaloids type manzamine and haliciclamineHaliclona). Family Niphatidae: Alkaloid alkylpiridínicos hachijodina type, pirinodemine and nifatoxin (Amphimedon, Niphates) Alkaloids benzopiridofenantrolinics (Anfimedina; Amphimedon) Haliciclamine-type alkaloidsAmphimedon) Alkaloid type arenosclerina (a)Pachychalina) Alkaloid type DBU (Niphates). Indolilimidazocabolinics (Kapakahinas); Cribrochalina) Pyrroloisocynolynic alkaloids (Cribostatins; Cribrochalina) Family Chalinidae Alkaloids type sarain (Reniera) Alkaloid type njaoamine (Reniera)	Ingenamine Xestospongina A Manzamina A
	Poeciloscleride	Myxillidae Family: Cyclopentanoindlic alkaloids (Dilemaones; Ectyonopsis) Acarnidae Family: Pyrroloindlic alkaloids (Damironas; Damiria) Hymedesmiidae Immidazlic steroidal Pseudoalcaloids (Amaranzol; Phorbas)	Dilemaona A
	Astrophorida	Ancorinidae Family: Bengamides and bengazolesJaspis) Alkyltetromic acids (Ancorina) Family Coppatidae Pteridine alkaloid (Asteropterin; Asteropus)	Acorinósido A
	Agelasida	Agelasidae Family: Clatrodine alkaloids (Clatrodines, nagelamins, ageliferinas, palauamines, axinelamines, styloisadines; Agelas) Astroscleridae Family: Clatrodine alkaloids (Ageliferinas; Astrosclera)	Palauamina
	Halichondrida	Axinellidae Family: Cyclopentan alkaloids (Herbindol; Axinella) Alkaloid type axinelamine (axinelamine)Axinella) Alkaloids triazaacenic (Ptilomicaline; Ptilocaulis) Family Halichondriidae: Succininimides (Cilindramida; Halichondria) Alkaloid bisindolimidazólicos (Topsentins, espongoins; Spongosorites)
	Dictyoceratida	Thorectidae Family: Henoxazoles (Henoxazoles)Smenospongia) Spiroimidazoindlic alkaloids (Dictazolinas, Tubastrindoles; Smenospongia) Irciniidae Family: Pyrolic alkaloids (irciniamin; Ircinia); Ircinal type lipidic pseudoalkaloidsIrcinia) Spongiidae Family Imidazoles conjugated with terpenes (Fasciospongins, pongolactamas, nakijiquinones; Spongia)
	Poeciloscleride	Chondropsidae Family: Alkaloids triazaacenfylénics (Batzeladines; Batzella) Pseudoalkaloids alkylpirimidics of lipidic origin (Batzelásidos; Batzella) Pyrroloquinolynic alkaloids (Batzelins; Batzella). Crambeidae Family: Alkaloids triazaacenfylénics (Batzeladines, Crambescidins; Monanchora)
	Choristida	Ancorinidae Family: Clavosins (Myriastra)
	Dendroceratida	Darwinellidae Family: Pyrimidinilindical Alkaloids (Psamopemines; Psammopemma) Morfolinas (Quelonins; Chelonaplysilla)
	Lithistida	Family Theonellidae: SwinhoeiamidesTheonella) Calculine-type oxazoles (Calculaine-type oxazoles)Discodermy) Polyenylpirrolidinic alkaloids (Aurantósidos; Theonella)
	Verongida	Pseudoceratinidae family: Immidazoazepinic alkaloids (Ceratamines; Pseudoceratin)
Calcárea	Clathrinida	Clathrinidae Family (Naamidines, polyandrocarpamines, leucetamine; Leucetta)

Class	Order	Families	Examples
Phylum Cnidaria
Anthozoa	Alcyonacea	Xeniidae Family: Isoindian diterpenic Pseudoalkaloids (Cespitulactamas); Cespitularia)	Cespitulactama D
	Pennatulacea	Renillidae Family: Fotóforos (Coelenteracina; Renilla)	Coelenteracin
	Actiniaria	Stichodactylidae Pyridinic alkaloids (Anfikuemine; Heteractis)
	Scleractinia	Dendrophylliidae Family: Cromanylpiperidinic alkaloids (Tubastrain; Tubastrea) Hydromethyl-methyl-metallic alkaloids Tubastrea) Acroporidae family Azepine Pseudoalkaloids (Montyperina E; Montipora)
	Antipatharia	Family Antipathidae Alkaloids imidazodiazaazulénicos (zoanthoxanthinas; Antipathes)
	Zoanthidea	Family Parazoanthidae Hidantoins (Parazoantins; Parazoanthus)
	Stolonifera	Clavulariidae family Terperinic esters of uroconic acid (Sarcodicine, eleutorobine; Sarcodictyon)

Class	Order	Families	Examples
Phylum Bryozoa
Gymnolaemata	Cheilostomata	Flustridae Family: Prenilpirroloindlic alkaloids (Flustramines; Fluster) Indolenic spiro-β-lactama alkaloids (Chartelins; Chartella)	Chartelina A
Gymnolaemata	Ctenostomata	Family Vesiculariidae Immidazlic alkaloids (Amatamides; Amathia)

Class	Order	Families	Examples
Phylum Platyhelminthes
Turbellaria	Polycladida	Euryleptidae Family: Alkaloids alquinilpirrolidins (Villatamines; Prostheceraeus)	Villatamina A

Class	Order	Families	Examples
Phylum Mollusca
Bivalvia	Mytiloida	Family Mytilidae Painless alkaloids (Oxazinins; Mytilus)	General structure of oxazinins
Bivalvia	Pterior	Family Pinnidae Spiropiperidynic alkaloids (pinnaic acid and tauropine acid; Pinna)	Pinnaic acid
Gastropda	Opisthobranchia	Gymnodorididae Family: Bispirolic alkaloids (Tambjamine; Tambja) Velutinidae Family: Kuanoniamine-type alkaloidsChelynotus) Aglajidae family Pyridinic alkaloids (Navenona A; Navanax)
	Sorbeoconcha	Muricidae Family: Bromoindialic and bromobisindolic pigments (Purgeon of Tyre; Murex, Hexaplex, Drupella) Idiocese Alkaloids conjugated with hill (Murexine; Murex) Family Babyloniidae: Surugatoxin and neosurugatoxin alkaloids (surgery)Babylonia (molusco))	Surugatoxin
	Vetigastropoda	Trochidae family Polyamide type Monodontamide (Monodontamide)Monodonta)
	Anaspide	Family Aplysiidae Alkaloids triazabiciclo[3,2,1]octanics (Aplaminal; Aplysia)
	Nudibranchia	Family Discodorididae Jorunamicin-type alkaloidsJorunna) Family Proctonotidae Tetromic acids (Janolusimida; Janolus)	Janolusimida

Class	Order	Families	Examples
Phylum Arthropoda
Insect	Diptera	Family Drosophilidae: Pteridin dimeric pigments (Drosofiline, drosopterin; Drosophila) Tephritidae PyrroloneCeratitis)
	Coleoptera	Coccinellidae Family: Hypodamine-type alkaloidsCoccinella, Hippodamia, Chauliognathus, Myrrha) Azamacrolactonas (Epilacneno; Epilachna) Polypirrolidinic alkaloids (Quilocorins; Chilocorus) Pyridoxazepinic alkaloids (Calvine, Calvia) Staphylinidae Family: Pyrrolidinic alkaloids (Estenusins; Stenus)	Estenusina Hipodamine
	Himenoptera	Crabronidae Family: Alkaloids derived from spermine (Filantotoxins; Philanthus) Formicidae Family: Dimetilpirrolidins (Ditiltypirrolidins)Solenopsis, Monomorium) Pyrroloindolizinic Alkaloids (Mirmicarinas, Monomorina; Myrmicaria) Pyrazinic alkaloids (2.5-Dimethyl-3-alkylpirazins, 2,6-Dimethyl-3-alkylpirazins; Odomanchus, Calomyrmex, Wasmannia, Atta, Myrmica, Tetramorium) Family Vespidae: Imadic acids of the imidazole (Polibiósido; Polybia)
	Lepidoptera	Family Pieridae: Tetrapirrbolic pigments (Pterobilina; Pieris, Catopsilia) Gelechiidae Family: Pyrimidinic alkaloids (Clitosine; Pectinophora) Family Arctiidae Alkaloid dihydropirrolizidinics (Hidroxidanaidal); Cisseps, Creatonotos; Estigmene; Phragmatobia) Family Nymphalidae Alkaloids dihydropirrolizidinics (Danaidona; Danaus) Family Saturniidae Porfibilinogen derivative pigments (Forcabilina; Rhodinia)
Diplopoda	Glomerida	Glomeridae Family: Corneral alkaloids (Glomerin; Glomeris)	Glomerin
Diplopoda	Polyzoniida	Family Polyzonidae: Alkaloids Spiropentanopirrolizidinics (Nitropolizonamine; Polyzonium)	Nitropolizonamina

Class	Order	Families	Examples
Phylum Echinodermata
Crinoid	Comatulida	Himerometridae family Aerothionine-type alkaloids (Aerothionine-type alkaloids)Himerometra)	Homoaerotionine
Stelleroida	Ophiurida	Family Ophiocomidae Indoloquinazolynic alkaloids (Ofiuroidin; Ophiocoma)	Ofiuroidina

Class	Order	Families	Examples
Phylum Chordata
Ascidiacea	Enterogona	Polyclinidae Family: Pseudoalkaloids cyclophonic azafluorénics (Haouaminas; Aplidium). Dixotiazinic alkaloids (Ascidiatiazone A and B; Aplidium). Pyrimidilindical Alkaloids (Meridianins; Aplidium) Clavelinidae Family: Chenophenanthrinnical alkaloids (Ascididemine; Cystodytes) Alkaloids ß-carbolinic derivatives of triptamine with cysteine (Eudistomines; Eudistoma) Alkaloids 1-pirrolil-ß-carbolinics (eudistomins A and M; Eudistoma). Family Perophoridae: Dimeres of tetrahydroisochinolins type ecteinascidina (Ecteinascidia) Pseudodistomidae Family: Tetrahydro-β-carbolinic alkaloids (arborcidins; Pseudodistoma).	Haouaminas Ascidiatiazona B
	Phlebobranchia	Family Diazonidae Oxalic alkaloids (Diazonamides; Diazon)	Diazonamide A
	Aplousobrachia	Family Didemnidae: Chenophenanthrinnical alkaloids (Ascididemine; Didemnum) Chromanoindolizinic alkaloids (Lamelarins; Didemnum) Indolilimidalylmalekydic alkaloids (Didemnimides; Didemnum) Alkaloids imidazocarbazólicos (Granulatimides; Didemnum) Family Polycitoridae Pyrazinic steroids (Riterazines; Ritterella)	Ascididemine Riterazina M
	Stolidobranchia	Styelidae Family: Idiocese Alkaloids (Policarpina; Polycarpus) Alkaloids α-carbolinics (Grossularins; Polycarpus)	Policarpina
Amphibia	Caudata	Salamandridae Family: Pseudoalcaloid azepinic alkaloidal (Samandarina); Salamandra)	Samandarina
Amphibia	Anura	Dendrobatidae Family: Pseudoalcaloid steroids with pyrrol rings (Batraciotoxin; (Phyllobates)) Alkaloids spirocyclohexanopiridinics (Histrionicotoxins and spirocyclopentanopirrolizidinics; Dendrobates) Pyrolizidinid alkaloids and quinolizidinics (Pumiliotoxins); Pumilio) Pyridinilazablanic alkaloids (Epibatidine; Epipedobates) Alkaloids spirocyclohexanopiperidinics (Histrionicotoxins; Dendrobates).	Histrionicotoxine 283A
Birds	Cuculiforms	Musophagidae Family: Tetrapirrbolic pigments (Turacina; Tauraco)	Turacina
Birds	Passeriformes	Pachycephalidae Family: Pseudoalcaloid steroids with pyrrol rings (Batraciotoxin; Pitohui)	Batraciotoxin
Mammalia	Carnivora	Mustelidae Family: Pyridines (4-Acetyl-3-methylpiridine; Mustela) Family Mephitidae: Quinolin (2-Methylchinolin, 2-(Mercaptomethyl)quinolin; Mephitis, Conepatus) Family Canidae Quinolins (Quinolin acid, Canis) Piperidona (Pyperidona)Canis)	2-(Mercaptomethyl)quinolin

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