Littorine

Last updated
Littorine
Littorine.svg
Names
Systematic IUPAC name
(1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl (R)-2-hydroxy-3-phenylpropanoate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)11-15(10-13)21-17(20)16(19)9-12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
    Key: FNRXUEYLFZLOEZ-FXUDXRNXSA-N
  • CN1[C@@H]2C[C@@H](OC([C@@H](CC3=CC=CC=C3)O)=O)C[C@H]1CC2
Properties
C17H23NO3
Molar mass 289.375 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Littorine is a tropane alkaloid found in a variety of plants including Datura [1] and Atropa belladonna . [2] It is closely related in chemical structure to atropine, hyoscyamine, and scopolamine, which all share a common biosynthetic pathway. [3] [4]

See also

Related Research Articles

<i>Datura</i> Genus of poisonous plants potentially psychoactive

Datura is a genus of nine species of poisonous, vespertine-flowering plants belonging to the family Solanaceae. They are commonly known as thornapples or jimsonweeds, but are also known as devil's trumpets. Other English common names include moonflower, devil's weed, and hell's bells. All species of Datura are poisonous and potentially psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, psychosis, and even death if taken internally. Due to their effects and symptoms, they have occasionally been used not only as a poison, but also as a hallucinogen by various groups throughout history. Traditionally, psychoactive administration of Datura species has often been associated with witchcraft and sorcery or similar practices in many cultures, including the Western world. Certain common Datura species have also been used ritualistically as entheogens by some Native American groups. Nonpsychoactive use of the plant is usually done for medicinal purposes, and the alkaloids present in plants of the Datura genus have long been considered traditional medicines in both the New and Old Worlds due to the presence of the alkaloids scopolamine and atropine, which are also produced by Old World plants such as Hyoscyamus niger, Atropa belladonna, and Mandragora officinarum.

Atropine pharmaceutical drug

Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings.

<i>Atropa</i> Genus of plants

Atropa is a genus of flowering plants in the nightshade family, Solanaceae : tall, calcicole, herbaceous perennials, bearing large leaves and glossy berries particularly dangerous to children, due to their combination of an attractive, cherry-like appearance with a high toxicity. Atropa species favour temperate climates and alkaline soils, often growing in light shade in woodland environments associated with limestone hills and mountains. Their seeds can remain viable in the soil for long periods, germinating when the soil of sites in which plants once grew is disturbed by human activity or by natural causes, e.g. the windthrow of trees. The best-known member of the genus Atropa is Deadly Nightshade - the poisonous plant par excellence in the minds of many. The pharmacologically active ingredients of Atropa species include atropine, scopolamine, and hyoscyamine, all tropane alkaloids having anticholinergic, deliriant, antispasmodic and mydriatic properties. The genus is named for Άτροπος (Atropos) - lit. 'she who may not be turned (aside)' - one of the Three Fates and cutter of the thread of life / bringer of death - in reference to the extreme toxicity of A.belladonna and its fellow species - of which three others are currently accepted.

<i>Atropa belladonna</i> Species of toxic flowering plant in the nightshade family.

Atropa belladonna, commonly known as belladonna or deadly nightshade, is a poisonous perennial herbaceous plant in the nightshade family Solanaceae, which also includes tomatoes, potatoes, and eggplant (aubergine). It is native to Europe, North Africa, and Western Asia. Its distribution extends from Great Britain in the west to western Ukraine and the Iranian province of Gilan in the east. It is also naturalised or introduced in some parts of Canada and the United States.

Secondary metabolite

Secondary metabolites, also called specialised metabolites, toxins, secondary products, or natural products, are organic compounds produced by bacteria, fungi, or plants which are not directly involved in the normal growth, development, or reproduction of the organism. Instead, they generally mediate ecological interactions, which may produce a selective advantage for the organism by increasing its survivability or fecundity. Specific secondary metabolites are often restricted to a narrow set of species within a phylogenetic group. Secondary metabolites often play an important role in plant defense against herbivory and other interspecies defenses. Humans use secondary metabolites as medicines, flavourings, pigments, and recreational drugs.

Hyoscyamine Pharmaceutical drug

Hyoscyamine is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, tomato, the sorcerers' tree, and deadly nightshade. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

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

Brugmansia is a genus of seven species of flowering plants in the family Solanaceae. They are woody trees or shrubs, with pendulous flowers, and have no spines on their fruit. Their large, fragrant flowers give them their common name of angel's trumpets, a name sometimes used for the closely related genus Datura..

Phytochemistry 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.

Deliriant Class of psychoactive drugs

Deliriants are a class of hallucinogen. The term was introduced by David F. Duncan and Robert S. Gold to distinguish these drugs from psychedelics and dissociatives, such as LSD and ketamine, respectively, due to their primary effect of causing delirium, as opposed to the more lucid states produced by such other hallucinogens as those represented by psychedelics and dissociatives. The term is generally used to refer to anticholinergic drugs which are substances that inhibit the function of the neurotransmitter acetylcholine. Common examples of deliriants include plants of the genus Datura as well as higher than recommended dosages of Diphenhydramine (Benadryl).

Cuscohygrine Chemical compound

Cuscohygrine is a pyrrolidine alkaloid found in coca. It can also be extracted from plants of the family Solanaceae, including Atropa belladonna, Datura innoxia and Datura stramonium. Cuscohygrine usually occurs along with other, more potent alkaloids such as atropine or cocaine.

<i>Scopolia</i> Genus of flowering plants

Scopolia is a genus of four species of flowering plants in the family Solanaceae, native to Europe and Asia. The genus is named after Giovanni Scopoli (1723–88), a Tyrolean naturalist. The genus has a disjunct distribution, with two recognised species in Central to Eastern Europe,, and two species in East Asia. The two European species are:

Donnatal is a combination medication that provides natural belladonna alkaloids in a specific fixed ratio combined with phenobarbital to provide peripheral anticholinergic/antispasmodic action and mild sedation. Donnatal is manufactured for Concordia Pharmaceuticals by IriSys, LLC. It is available as tablets and 5 mL elixir. Active ingredients are listed as: phenobarbital (16.2 mg), hyoscyamine sulfate (0.1037 mg), atropine sulfate (0.0194 mg), and scopolamine hydrobromide (0.0065 mg). The latter two ingredients are found in plants of the family Solanaceae, such as belladonna.

Tropane alkaloid Class of chemical compounds

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Some tropane alkaloids have pharmacological properties and can act as anticholinergics or stimulants.

Hairy root culture, also called transformed root culture, is a type of plant tissue culture that is used to study plant metabolic processes or to produce valuable secondary metabolites or recombinant proteins, often with plant genetic engineering.

Scopoletin Chemical compound

Scopoletin is a coumarin. It found in the root of plants in the genus Scopolia such as Scopolia carniolica and Scopolia japonica, in chicory, in Artemisia scoparia, in the roots and leaves of stinging nettle, in the passion flower, in Brunfelsia, in Viburnum prunifolium, in Solanum nigrum, in Datura metel, in Mallotus resinosus, or and in Kleinhovia hospita. It can also be found in fenugreek, vinegar, some whiskies or in dandelion coffee. A similar coumarin is scoparone. Scopoletin is highly fluorescent when dissolved in DMSO or water and is regularly used as a fluorimetric assay for the detection of hydrogen peroxide in conjunction with horseradish peroxidase. When oxidized, its fluorescence is strongly suppressed.

<i>Scopolia japonica</i> Species of flowering plant

Scopolia japonica, also Japanese belladonna or Korean scopolia, is a flowering plant species in the genus Scopolia - one of the eight genera in tribe Hyoscyameae of the nightshade family Solanaceae.

Tropine acyltransferase is an enzyme with systematic name acyl-CoA:tropine O-acyltransferase. This enzyme catalyses the following chemical reaction

Solanaceae Family of flowering plants that includes tomatoes, potatoes and tobacco

The Solanaceae, or 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.

<i>Atropa baetica</i> Species of flowering plant

Atropa baetica is one of Europe's rarest wildflowers. A close relative of the infamous deadly nightshade its specific name derives from that of the Roman province of Hispania Baetica, while its common name refers to the Spanish region of Andalucía – both designating the area in the south of Spain where it is most frequently encountered. It is an attractive, perennial herbaceous plant bearing infundibuliform, yellow or greenish flowers and shiny, black berries. Like the other three species of Atropa, it is an extremely poisonous plant, containing a variety of tropane alkaloids with anticholinergic, deliriant, antispasmodic and mydriatic properties. Although most populations of the plant are to be found in Spain, it is not wholly confined to the Iberian Peninsula of Europe, occurring also in certain localities in Morocco and Algeria in the Atlas Mountains of North Africa. The Rif and the Baetic System, which face each other across the Alboran Sea, together constitute one of the finest of the Mediterranean biodiversity hotspots – rich in endemic species, of which Atropa baetica is a notable example..

References

  1. Evans, W. C.; Ghani, A.; Woolley, V. A. (1972). "Distribution of littorine and other alkaloids in the roots of Datura species". Phytochemistry. 11 (8): 2527–2529. doi:10.1016/S0031-9422(00)88530-1.
  2. Nakanishi, F.; Sasaki, K.; Shimomura, K. (1998). "Isolation and identification of littorine from hairy roots of Atropa belladonna". Plant Cell Reports. 18 (3–4): 249–251. doi:10.1007/s002990050565.
  3. Zabetakis, I.; Edwards, R.; Hamilton, J. T. G.; O'Hagan, D. (1998). "The biosynthetic relationship between littorine and hyoscyamine in transformed roots of Datura stramonium". Plant Cell Reports. 18 (3–4): 341–345. doi:10.1007/s002990050583.
  4. Lanoue, A.; Boitel-Conti, M.; Portais, J.-C.; Laberche, J.-C.; Barbotin, J.-N.; Christen, P.; Sangwan-Norreel, B. (2002). "Kinetic Study of Littorine Rearrangement in Datura innoxia Hairy Roots by 13C NMR Spectroscopy". Journal of Natural Products. 65 (8): 1131–1135. doi:10.1021/np010612c. PMID   12193016.