Eduline Circulatory System

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Dopamine

ISAM

H3C-O

ISAM

o-ch3

P1 Mescaline

Noradrenaline

[SAM

Noradrenaline

[SAM

NH-CH3 Adrenaline

o-ch3

P1 Mescaline

Figure 63. Structural development of phenyl and phenylpropyl alkaloids.

CO2H

alkaloids (e.g., eserine) and ergot alkaloids (e.g., ergotamine). Indole alkaloids form a very important group from the perspective of their application.

Simple indole alkaloids

The a for structural development of serotonin (simple indole alkaloid) is L-tryptophan, and the ft is 5-hydroxy-L-tryptophan (Figure 64). Serotonin is a monoamine. It is a bioactive alkaloid known as a neurotransmitter. It has been found in the cardiovascular system, in blood cells and the peripheral and CNS.

The a for the structural development of psilocin and psilocybin is L-tryptophan and the ft is tryptamine. Psilocin is A and psilocybin is P. A and P are the main alkaloids in hallucinogenic mushrooms belonging to the genus Psilocybe.

Carboline alkaloids

The a of carboline alkaloids is l -tryptophan and the ft is tryptamine, while the ^ is dihydro-ft-carboline. The carboline nucleus is formed at the stage of the The A is elaeagnine, harman and harmaline, and the P is tetrahydroharmine or harmine (Figure 65).

Carboline alkaloids, and especially ft-carbolines, are common in mammals211.

Harry Potter Triangle

Psilocybin

Figure 64. Structural development of simple indole alkaloids.

Psilocybin

Figure 64. Structural development of simple indole alkaloids.

Terpenoid indole alkaloids

This group of alkaloids is very large and contains more than 3000 compounds.

Three types of nucleus occur here: the corynanthe, iboga and aspidosperma.

1. Corynanthe alkaloids: The a of structural development is L-tryptophan and the ft is tryptamine. The strictosidine is the Moreover, the x is dehydro-geissoschizine and the A is cathenamine. Ajmalicine is the P of cathenamine (Figure 66).

2. Iboga alkaloids: The common monomeric iboga alkaloids are ibogamine, ibogaine, coronaridine, voacangine and catharanthine. Ibogamine and catha-ranthine are prototypical structures. The a for cathenamine is L-tryptophan and the ft is strictosidine, as in the case of Corynanthe alkaloids. Ibogaine is

Tryptophan Derived Alkaloids

N ß-carboline

Tryptamine

Tryptamine

Tetrahydroharmine

Elaeagnine

Figure 65. Structural development of carboline alkaloids.

Harmine

Harman

Tetrahydroharmine

Elaeagnine

Figure 65. Structural development of carboline alkaloids.

Harmine

Harman the P of cathenamine (Figure 67). The iboga-type nucleus is derived from the Corynanthe type32.

3. Aspidosperma alkaloids: These alkaloids have an aspidosperma-type nucleus. The a and ft are the same as in corynanthe type. Catharantine is the P4 from cathenamine (Figure 68).

Quinoline alkaloids

This group of alkaloids has two structurally different a. The a of alkaloids found in the genus Cinchona (Rubiaceae), such as quinine, quinidine, cinchonidine and cinchonine, is L-tryptophan. The ft is tryptamine and the ^ is strictosidine. The corynantheal is the x. A is cinchonamine and cinchoninone. Cinchonine, quinidine, quinine and cinchonidine are the Ps of cinchoninone (Figure 69).

The second type of quinoline alkaloid, found especially found in the Rutaceae family, has a as anthranilic acid. Typical compounds from this group are eduli-tine, halfordamine, folifidine, folinine, casimiroin, foliosidine and swietenidine. The ft is 3-carboxyquinoline and the A is graveoline in the case of those alkaloids from Ruta angustifolia.

Molecule Structure For Love

CO2-CH3

NH V H OGlc

CO2-CH3

Dehydrogeissoschizine / x

CO2-CH3

Ajmalicine

CO2-CH3

Ajmalicine

CO2-CH3

Figure 66. Structural development of corynanthe alkaloids.

In the case of S. japonica, the A is eduline and is formed directly from a in the decarboxylation process. In the case of micro-organisms, for example Pseudomonas aeruginosa, the a is incorporated directly to the A, which is 2-heptyl-4-hydroxyquinoline.

20,21-dehydrocorynantheine aldehyde

Ibogaine

20,21-dehydrocorynantheine aldehyde

Ibogaine

.OGlc

H3C-O2C'

20,21-dehydrocorynantheinealdehyde

20,21-dehydrocorynantheinealdehyde

Mechanism Ring Opening Caprolactam

Cathenamine

Preakuammicine P1

Cathenamine h3c-o2c ch2-oh

Preakuammicine P1

H3C-O2C ch2-oh Stemmadenine

H3C-O2C ch2-oh Stemmadenine

Dehydrosecodine

Dehydrosecodine

Catharanthine

Strictosidine

Figure 69. Structural development of quinoline alkaloids.

Quinoline alkaloids from the Rutaceae family (a = L-anthranilic acid) show antimicrobial activity. Moreover, quinoline alkaloids of the Haplophyllum species are known for their powerful biological properties. For example, skim-mianine has sedative, hypothermic and antidiuretic uses. Haplophyllidine is a strong depressant of the CNS.

L-tryptophan nh2

L-tryptophan

H Tryptamine

h3c-

h3c-

Methyltryptamine

D Eserine .

Chimonanthine P A

Figure 70. Structural development of pyrroloindole alkaloids.

Pyrroloindole alkaloids

The a of this group of alkaloids is L-tryptophan and the ft is tryptamine, and the ^ is methyltryptamine (Figure 70). The best-known alkaloids belonging to this group are eserine (A), chimonanthine (P), eseramine, physovenine, rivastigmine, eptastigmine, neostigmine, pyridostigmine and distigmine.

Ergot alkaloids

The a for ergot alkaloids is L-tryptophan and the ft is four-steps alkaloid reaction chain. The ^ is paspalic acid which converts to the d-(+)-lysergic acid (Figure 71). Ergotamine and ergometrine are the best-known members of this group.

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