Gedunin

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Gedunin
Gedunin.svg
Names
IUPAC name
Gedunin
Systematic IUPAC name
[(1S,2R,4S,7S,8S,11R,12R,17R,19R)-7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadec-13-en-19-yl] acetate
Other names
  • Gedunine
  • (-)-Gedunin
  • (1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(Furan-3-yl)-4b,7,7,10a,12a-pentamethyl-3,8-dioxo-1,3,3a,4b,5,6,6a,7,8,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]oxireno[2,3-d]isochromen-5-yl acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gedunin is a pentacyclic triterpenoid with the molecular formula C28H34 O7. It is most notably found in Azadirachta indica, [1] but is a constituent of several other plants. Gedunin shows therapeutic potential in the treatment of leukemia, [2] and Parkinson's disease. [3] [4]

Natural occurrence

Azadirachta indica [5] is the most notable source of gedunin, but it has also been found in the following plants:

Related Research Articles

<i>Azadirachta indica</i> Species of plant

Azadirachta indica, commonly known as neem, margosa, nimtree or Indian lilac, is a tree in the mahogany family Meliaceae. It is one of two species in the genus Azadirachta. It is native to the Indian subcontinent and to parts of Southeast Asia, but is naturalized and grown around the world in tropical and subtropical areas. Its fruits and seeds are the source of neem oil. Nim (नीम) is a Hindustani noun derived from Sanskrit nimba (निंब).

<span class="mw-page-title-main">Meliaceae</span> Family of plants commonly known as the Mahogany family

Meliaceae, the mahogany family, is a flowering plant family of mostly trees and shrubs in the order Sapindales.

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

Azadirachtin, a chemical compound belonging to the limonoid group, is a secondary metabolite present in neem seeds. It is a highly oxidized tetranortriterpenoid which boasts a plethora of oxygen-bearing functional groups, including an enol ether, acetal, hemiacetal, tetra-substituted epoxide and a variety of carboxylic esters.

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

Limonoids are phytochemicals of the triterpenoid class which are abundant in sweet or sour-scented citrus fruit and other plants of the families Cucurbitaceae, Rutaceae, and Meliaceae. Certain limonoids are antifeedants such as azadirachtin from the neem tree.

<span class="mw-page-title-main">Neem oil</span> Vegetable oil from the Indian neem tree

Neem oil, also known as margosa oil, is a vegetable oil pressed from the fruits and seeds of the neem, a tree which is indigenous to the Indian subcontinent and has been introduced to many other areas in the tropics. It is the most important of the commercially available products of neem, and its chemical properties have found widespread use as a pesticide in organic farming.

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

Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast, plant steroids are produced via cycloartenol.

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

Incarvillea is a genus of about 16 species of flowering plants in the family Bignoniaceae, native to central and eastern Asia, with most of the species growing at high altitudes in the Himalaya and Tibet. The most familiar species is Incarvillea delavayi, a garden plant commonly known as hardy gloxinia or Chinese trumpet flower. Unlike most other members of Bignoniaceae, which are mainly tropical woody plants, species of Incarvillea are herbaceous perennial plants from temperate regions.

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

Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.

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

Beesia is a genus of flowering plants in the buttercup family. It was named in 1915 after the plant nursery firm Bees of Chester, who financed the plant hunting trips of George Forrest and Frank Kingdon-Ward in China.

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

Ergosterol peroxide (5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol) is a steroid derivative. It has been isolated from a variety of fungi, yeast, lichens and sponges, and has been reported to exhibit immunosuppressive, anti-inflammatory, antiviral, trypanocidal and antitumor activities in vitro.

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

A quinone methide is a type of conjugated organic compound that contain a cyclohexadiene with a carbonyl and an exocyclic methylidene or extended alkene unit. It is analogous to a quinone, but having one of the double bonded oxygens replaced with a carbon. The carbonyl and methylidene are usually oriented either ortho or para to each other. There are some examples of transient synthetic meta quinone methides.

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

The molecule malabaricane and its derivatives, the malabaricanes, are triterpene and triterpenoid compounds found in various organisms. They are named after the rain forest tree Ailanthus malabarica, from which they were first isolated in 1967 by scientists at the National Chemical Laboratory in Pune, India. Later, great varieties of malabaricanes were discovered in other organisms, mostly in marine sponges such as Rhabdastrella globostellata.

<span class="mw-page-title-main">Nimbin (chemical)</span> Chemical compound

Nimbin is a triterpenoid isolated from Neem. Nimbin is thought to be responsible for much of the biological activities of neem oil, and is reported to have anti-inflammatory, antipyretic, fungicidal, antihistamine and antiseptic properties.

<span class="mw-page-title-main">14-Norpseurotin A</span> Chemical compound

14-Norpseurotin A is an alkaloid and a bio-active metabolite of Aspergillus, featuring an oxa-spiro-lactam core.

Bacopasides are triterpene saponins isolated from Bacopa monnieri.

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

Ergostane is a tetracyclic triterpene, also known as 24S-methylcholestane. The compound itself has no known uses; however various functionalized analogues are produced by plants and animals. The most important of these are the heavily derivatised withanolides. However simpler forms do exist, such as the sterane campestane (24R-methylcholestane). Along with cholestane and stigmastane, this sterane is used as a biomarker for early eukaryotes.

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

Incarvillateine is a complex monoterpene alkaloid that is a derivative of α-truxillic acid. It can be isolated from the plant genus Incarvillea.

<i>Incarvillea sinensis</i> Species of flowering plant

Incarvillea sinensis is a plant species in the genus Incarvillea.

<span class="mw-page-title-main">Dichapetalins</span>

Dichapetalins are a small class of triterpenoid compounds found primarily in the Dichapetalaceae family but also reportedly in Phyllanthus (Euphorbiaceae). They are structural derivatives of dammarene characterized by a C6C2 unit connected to a dammarene or a 13,30-cyclodammarane skeleton with variable C-17 side chains containing actone, spirolactone, lactol, acetal, or furan moieties. They have been found to display cytotoxicity against several cancer cell lines.

<i>Plakortis</i> Genus of sponges

Plakortis is a genus of marine sponges in the order Homosclerophorida, first described by Franz Eilhard Schulze in 1880.

References

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