Indole alkaloid

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.Harmal contains β-carboline alkaloidsIpomoea violacea contains ergolinesAlstonia macrophylla contains Corynanthe alkaloidsRauwolfia serpentina contains Corynanthe alkaloidsCatharanthus roseus contains monoterpenoid indole alkaloidsPsilocybe cubensis contains psilocybin and psilocinErgot contains ergolinesColorado River toad (Bufo alvarius) contains bufotenin and 5-MeO-DMT Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids. The action of some indole alkaloids has been known for ages. Aztecs used the psilocybin mushrooms which contain alkaloids psilocybin and psilocin. The flowering plant Rauwolfia serpentina which contains reserpine was a common medicine in India around 1000 BC. Africans used the roots of the perennial rainforest shrub Iboga, which contain ibogaine, as a stimulant. An infusion of Calabar bean seeds was given to people accused of crime in Nigeria: its rejection by stomach was regarded as a sign of innocence, otherwise, the person was killed via the action of physostigmine, which is present in the plant and which causes paralysis of the heart and lungs. Consumption of rye and related cereals contaminated with the fungus Claviceps purpurea causes ergot poisoning and ergotism in humans and other mammals. The relationship between ergot and ergotism was established only in 1717, and the alkaloid ergotamine, one of the main active ingredients of ergot, was isolated in 1918. The first indole alkaloid, strychnine, was isolated by Pierre Joseph Pelletier and Joseph Bienaimé Caventou in 1818 from the plants of the genus Strychnos. The correct structural formula of strychnine was determined only in 1947, although the presence of the indole nucleus in the structure of strychnine was established somewhat earlier. Indole itself was first obtained by Adolf von Baeyer in 1866 while decomposing Indigo. Depending on their biosynthesis, two types of indole alkaloids are distinguished; isoprenoids and non-isoprenoids. The latter include terpenoid structural elements, synthesized by living organisms from dimethylallyl pyrophosphate (DMAPP) and/or isopentenyl pyrophosphate (IPP): There are also purely structural classifications based on the presence of carbazole, β-carboline or other units in the carbon skeleton of the alkaloid molecule. Some 200 dimeric indole alkaloids are known with two indole groups. The number of known non-isoprenoid indole alkaloids is small compared to the number of indole alkaloids. One of the simplest and yet widespread indole derivatives are the biogenic amines tryptamine and 5-hydroxytryptamine (serotonin). Although their assignment to the alkaloid is not universally accepted, they are both found in plants and animals. The tryptamine skeleton is part of the vast majority of indole alkaloids. For example, N,N-dimethyltryptamine (DMT), psilocin and its phosphorylated psilocybin are the simplest derivatives of tryptamine. Some simple indole alkaloids do not contain tryptamine, such as gramine and glycozoline (the latter is a derivative of carbazole). Camalexin is a simple indole alkaloid produced by the plant Arabidopsis thaliana, often used as a model for plant biology. The prevalence of β-carboline alkaloids is associated with the ease of forming the β-carboline core from tryptamine in the intramolecular Mannich reaction. Simple (non-isoprenoid) β-carboline derivatives include harmine, harmaline, harmane and a slightly more complex structure of canthinone. Harmaline was first isolated in 1838 by Göbel and harmine in 1848 by Fritzche.