Pyridine alkaloids

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Pyridine, the parent compound of the pyridine alkaloids. Pyridin.svg
Pyridine, the parent compound of the pyridine alkaloids.

Pyridine alkaloids are a class of alkaloids, nitrogen-containing chemical compounds widely found in plants, that contain a pyridine ring. Examples include nicotine and anabasine which are found in plants of the genus Nicotiana including tobacco. [1]

Alkaloids with a pyridine partial structure are usually further subdivided according to their occurrence and their biogenetic origin. The most important examples of pyridine alkaloids are the nicotine and anabasine, which are found in tobacco, [2] the areca alkaloids in betel and ricinine in castor oil. [3]

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<span class="mw-page-title-main">Alkaloid</span> Class of naturally occurring chemical compounds

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

<span class="mw-page-title-main">Piperidine</span> Chemical compound

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.

<span class="mw-page-title-main">Nicotine</span> Chemical stimulant produced by some plants

Nicotine is a naturally produced alkaloid in the nightshade family of plants and is widely used recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is used for smoking cessation to relieve withdrawal symptoms. Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs), except at two nicotinic receptor subunits where it acts as a receptor antagonist.

<i>Nicotiana</i> Genus of flowering plants in the nightshade family Solanaceae

Nicotiana is a genus of herbaceous plants and shrubs in the family Solanaceae, that is indigenous to the Americas, Australia, Southwestern Africa and the South Pacific. Various Nicotiana species, commonly referred to as tobacco plants, are cultivated as ornamental garden plants. N. tabacum is grown worldwide for the cultivation of tobacco leaves used for manufacturing and producing tobacco products, including cigars, cigarillos, cigarettes, chewing tobacco, dipping tobacco, snuff, and snus.

<i>Streptosolen</i> Species of plant

Streptosolen is a monotypic genus of flowering plants in the family Solanaceae. It is closely related to the genus Browallia, within which it was originally placed. The single species, Streptosolen jamesonii, the marmalade bush or fire bush, is an evergreen shrub bearing loose clusters of flowers which change gradually from yellow to red as they develop, resulting in an overall appearance resembling orange marmalade, found in open woodlands in Colombia, Venezuela, Ecuador, and Peru. In its native Ecuador, the plant has the Spanish common names flor de quinde, flor del sol and jaboncillo.

<i>Nicotiana glauca</i> Species of plant

Nicotiana glauca is a species of flowering plant in the tobacco genus Nicotiana of the nightshade family Solanaceae. It is known by the common name tree tobacco. Its leaves are attached to the stalk by petioles, and its leaves and stems are neither pubescent nor sticky like Nicotiana tabacum. It resembles Cestrum parqui but differs in the form of leaves and fusion of the outer floral parts. It grows to heights of more than two meters.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

<i>Nicotiana rustica</i> Species of plant

Nicotiana rustica, commonly known as Aztec tobacco or strong tobacco, is a rainforest plant in the family Solanaceae native to South America It is a very potent variety of tobacco, containing up to nine times more nicotine than common species of Nicotiana such as Nicotiana tabacum. More specifically, N. rustica leaves have a nicotine content as high as 9%, whereas N. tabacum leaves contain about 1 to 3%. The high concentration of nicotine in its leaves makes it useful for producing pesticides, and it has a wide variety of uses specific to cultures around the world. However, N. rustica is no longer cultivated in North America, as N. tabacum has replaced it.

<i>Nicotiana benthamiana</i> Species of flowering plant

Nicotiana benthamiana, colloquially known as benth or benthi, is a species of Nicotiana indigenous to Australia. It is a close relative of tobacco.

<i>Nicotiana tabacum</i> Species of plant

Nicotiana tabacum, or cultivated tobacco, is an annually grown herbaceous plant of the genus Nicotiana. N. tabacum is the most commonly grown species in the genus Nicotiana, as the plant's leaves are commercially harvested to be processed into tobacco for human use. The plant is tropical in origin, is commonly grown throughout the world, and is often found in cultivation. It grows to heights between 1 and 2 meters. Research is ongoing into its ancestry among wild Nicotiana species, but it is believed to be a hybrid of Nicotiana sylvestris, N. tomentosiformis, and possibly N. otophora.

<span class="mw-page-title-main">Anabasine</span> Chemical compound

Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco plant, as well as in the close relative of the common tobacco plant. It is a structural isomer of, and chemically similar to, nicotine. Its principal (historical) industrial use is as an insecticide.

<span class="mw-page-title-main">Heterocyclic amine</span> Any heterocyclic compound having at least one nitrogen heteroatom

Heterocyclic amines, also sometimes referred to as HCAs, are chemical compounds containing at least one heterocyclic ring, which by definition has atoms of at least two different elements, as well as at least one amine (nitrogen-containing) group. Typically it is a nitrogen atom of an amine group that also makes the ring heterocyclic, though compounds exist in which this is not the case. The biological functions of heterocyclic amines vary, including vitamins and carcinogens. Carcinogenic heterocyclic amines are created by high temperature cooking of meat and smoking of plant matter like tobacco. Some well known heterocyclic amines are niacin, nicotine, and the nucleobases that encode genetic information in DNA.

Pituri, also known as mingkulpa, is a mixture of leaves and wood ash traditionally chewed as a stimulant by Aboriginal Australians widely across the continent. Leaves are gathered from any of several species of native tobacco (Nicotiana) or from at least one distinct population of the species Duboisia hopwoodii. Various species of Acacia, Grevillea and Eucalyptus are burned to produce the ash. The term "pituri" may also refer to the plants from which the leaves are gathered or from which the ash is made. Some authors use the term to refer only to the plant Duboisia hopwoodii and its leaves and any chewing mixture containing its leaves.

Tobacco-specific nitrosamines (TSNAs) comprise one of the most important groups of carcinogens in tobacco products, particularly cigarettes and fermented dipping snuff.

<span class="mw-page-title-main">Rivanicline</span> Chemical compound

Rivanicline is a drug which acts as a partial agonist at neural nicotinic acetylcholine receptors. It is subtype-selective, binding primarily to the α4β2 subtype. It has nootropic effects and was originally developed as a potential treatment for Alzheimer's disease, but a second action that was subsequently found was that it inhibits the production of Interleukin-8 and thus produces an antiinflammatory effect, and so it has also been developed as a potential treatment for ulcerative colitis. Rivanicline also has stimulant and analgesic actions which are thought to be mediated through stimulation of noradrenaline release, and so it could also have other applications. It has been identified as constituent of tobacco as well.

<span class="mw-page-title-main">Anatabine</span> Chemical compound

Anatabine (uh-nat-uh-been,-bin) is one of the minor alkaloids found in plants in the family Solanaceae, which includes the tobacco plant and tomato. Commercial tobacco plants typically produce alkaloids at levels between 2% and 4% of total dry weight, with nicotine accounting for about 90% of the total alkaloid content, and the related compounds anatabine, nornicotine, and anabasine making up nearly all the rest. These compounds are thought to be biologically active, and part of plants' natural defense system against insects.

<span class="mw-page-title-main">Myosmine</span> Chemical compound

Myosmine is an alkaloid found in tobacco and other plants. Chemically, it is closely related to nicotine. It inhibits aromatase sevenfold more potently than nicotine. It also releases dopamine in adult but not adolescent rats.

<span class="mw-page-title-main">Nornicotine</span> Chemical compound

Nornicotine is an alkaloid found in various plants including Nicotiana, the tobacco plant. It is chemically similar to nicotine, but does not contain a methyl group.

<span class="mw-page-title-main">Psychoactive plant</span> Plants that induce psychotropic effects upon ingestion

Psychoactive plants are plants, or preparations thereof, that upon ingestion induce psychotropic effects. As stated in a reference work:

Psychoactive plants are plants that people ingest in the form of simple or complex preparations in order to affect the mind or alter the state of consciousness.

<span class="mw-page-title-main">Solanaceae</span> Family of flowering plants that includes tomatoes, potatoes and tobacco

The Solanaceae, or the nightshades, are a family of flowering plants that ranges from annual and perennial herbs to vines, lianas, epiphytes, shrubs, and trees, and includes a number of agricultural crops, medicinal plants, spices, weeds, and ornamentals. Many members of the family contain potent alkaloids, and some are highly toxic, but many—including tomatoes, potatoes, eggplant, bell and chili peppers—are used as food. The family belongs to the order Solanales, in the asterid group and class Magnoliopsida (dicotyledons). The Solanaceae consists of about 98 genera and some 2,700 species, with a great diversity of habitats, morphology and ecology.

References

  1. "Pyridine Alkaloids". Cornell University, Department of Animal Science.
  2. Laszlo C, Kaminski K, Guan H, Fatarova M, Wei J, Bergounioux A, Schlage WK, Schorderet-Weber S, Guy PA, Ivanov NV, Lamottke K, Hoeng J (November 2022). "Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species". Molecules. 27 (22): 8105. doi: 10.3390/molecules27228105 . PMC   9694777 . PMID   36432206.
  3. Entry on Pyridin . at: Römpp Online . Georg Thieme Verlag, retrieved 20. Juni 2014.