Evoxine

Last updated
Evoxine
Evoxine.svg
Names
IUPAC name
(±)-1-(4,8-Dimethoxyfuro[2,3-b]quinolin-7-yl)oxy-3-methylbutane-2,3-diol
Other names
Haploperine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
    Key: FGANMDNHTVJAHL-UHFFFAOYSA-N
  • InChI=1/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
    Key: FGANMDNHTVJAHL-UHFFFAOYAV
  • CC(C)(C(COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC)O)O
Properties
C18H21NO6
Molar mass 347.367 g·mol−1
Pharmacology
none
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Evoxine (haploperine) is a furoquinoline alkaloid with hypnotic and sedative effects. It is found naturally in a variety of Australian and African plants including Evodia xanthoxyloides [1] and Teclea gerrardii . [2]

Related Research Articles

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

Murraya is a genus of flowering plants in the citrus family, Rutaceae. It is distributed in Asia, Australia, and the Pacific Islands. The center of diversity is in southern China and Southeast Asia. When broadly circumscribed, the genus has about 17 species. A narrower circumscription contains only eight species, others being placed in Bergera and Merrillia.

<span class="mw-page-title-main">Pyrrolizidine alkaloid</span> Class of chemical compounds

Pyrrolizidine alkaloids (PAs), sometimes referred to as necine bases, are a group of naturally occurring alkaloids based on the structure of pyrrolizidine. Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect herbivores. More than 660 PAs and PA N-oxides have been identified in over 6,000 plants, and about half of them exhibit hepatotoxicity. They are found frequently in plants in the Boraginaceae, Asteraceae, Orchidaceae and Fabaceae families; less frequently in the Convolvulaceae and Poaceae, and in at least one species in the Lamiaceae. It has been estimated that 3% of the world’s flowering plants contain pyrrolizidine alkaloids. Honey can contain pyrrolizidine alkaloids, as can grains, milk, offal and eggs. To date (2011), there is no international regulation of PAs in food, unlike those for herbs and medicines.

<span class="mw-page-title-main">Uzazi</span> West African spice

"Uzazi" is the Nigerian name for the 'prickly ash' tree of genus Zanthoxylum tessmannii / Fagara tessmannii / Zanthoxylum gilletii, a member of the Rutaceae family, native to Central and West Africa, and a close relative of the Sichuan pepper. It usually refers specifically to the spice made from its fruit and pericarp, though sometimes other parts of it such as its leaves are used.

Teclea carpopunctifera is a small forest tree in the family Rutaceae. The genus Teclea has been synonymized with Vepris, but this species appears not to have been given a name in Vepris and is regarded as "unplaced" by Plants of the World Online. It is endemic to Côte d'Ivoire.

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

Vepris is a genus of plant in family Rutaceae. It comprises around 90 species, mainly from tropical Africa, Madagascar and the Mascarene Islands and at a lesser extent Arabia and India.

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

Pericine is one of a number of indole alkaloids found in the tree Picralima nitida, commonly known as akuamma. As with some other alkaloids from this plant such as akuammine, pericine has been shown to bind to mu opioid receptors in vitro, and has an IC50 of 0.6 μmol, within the range of a weak analgesic. It may also have convulsant effects.

<i>Tetradium daniellii</i> Species of flowering plant

Tetradium daniellii, the bee-bee tree or Korean evodia, is a species of flowering plant in the family Rutaceae. It is native to Korea and southwestern China.

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

Phellodendrine is an alkaloid isolated originally from Phellodendron amurense (Rutaceae).

<i>Papilio constantinus</i> Species of butterfly

Papilio constantinus, the Constantine's swallowtail, is a butterfly of the family Papilionidae. It is found in Sub-Saharan Africa.

<i>Euodia</i> (plant) Genus of flowering plants

Euodia is a plant genus in the family Rutaceae. Euodia is sometimes misspelled as Evodia. The species now included in the genus Tetradium were previously included in Euodia, and may be commonly referred to as euodia.

<i>Zanthoxylum zanthoxyloides</i> Species of flowering plant

Zanthoxylum zanthoxyloides, also called Senegal prickly-ash or artar root, is a plant species in the genus Zanthoxylum.

<i>Papilio mackinnoni</i> Species of butterfly

Papilio mackinnoni, the Mackinnon's swallowtail, is a species of swallowtail butterfly from the genus Papilio that is found in Kenya, Tanzania, Malawi, Zambia, Angola, Uganda, Zaire, South Sudan, the Republic of the Congo, Rwanda and Burundi.

<span class="mw-page-title-main">Furoquinoline alkaloid</span> Group of chemical compounds

Furoquinoline alkaloids are a group of alkaloids with simple structure. Distribution of this group of alkaloids is essentially limited to plant family Rutaceae. The simplest member of this group is dictamnine and most widespread member is skimmianine.

<span class="mw-page-title-main">Rutecarpine</span> COX-2 inhibitor compound

Rutecarpine or rutaecarpine is a COX-2 inhibitor isolated from Tetradium ruticarpum, a tree native to China. It is classified as a non-basic alkaloid.

<i>Tetradium ruticarpum</i> Species of tree

Tetradium ruticarpum is a tree that comes from China and Korea. It was previously classified in the genus Euodia as Euodia ruticarpa. The fruit is usually used, denoted sometimes as fructus. It has a strong bitter taste, and is used in traditional Chinese medicine (TCM) and is a recognized herb in Kampo. Both the former genus name and the species name are often misspelled, and the plant usually appears in sources dealing with traditional Chinese medicine as "Evodia(e) rutaecarpa".

Marco Duretto is a manager and senior research scientist at the Royal Botanic Gardens Sydney in Australia.

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

Skimmianine is a furoquinoline alkaloid found in Skimmia japonica, a flowering plant in family Rutaceae that is native to Japan and China. It is also a strong acetylcholinesterase (AChE) inhibitor.

<i>Melicope rubra</i> Species of tree

Melicope rubra, commonly known as the little evodia, is a species of small tree in the family Rutaceae, and is endemic to north-east Queensland. It has trifoliate leaves and pink bisexual flowers arranged on branches below the leaves.

<i>Melicope vitiflora</i> Species of tree

Melicope vitiflora, commonly known as northern evodia, fishpoison wood, leatherjacket or leatherwood, is a species of shrub or small tree in the family Rutaceae and is native to north-eastern Australia and New Guinea. It has trifoliate leaves and green to white or cream-coloured flowers borne in panicles in leaf axils.

References

  1. Eastwood, FW; Hughes, GK; Ritchie, E. (1954). "Alkaloids of the Australian Rutaceae: Evodia xanthoxyloides F.Muell. IV. The structures of Evoxine and Evoxoidine". Australian Journal of Chemistry. 7 (1): 87–98. doi:10.1071/CH9540087.
  2. Waffo, AF; Coombes, PH; Crouch, NR; Mulholland, DA; El Amin, SM; Smith, PJ (2007). "Acridone and furoquinoline alkaloids from Teclea gerrardii (Rutaceae: Toddalioideae) of southern Africa". Phytochemistry. 68 (5): 663–7. Bibcode:2007PChem..68..663K. doi:10.1016/j.phytochem.2006.10.011. PMID   17174364.