Limonoid

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Chemical structure of the prototypical limonoid limonin Limonin.svg
Chemical structure of the prototypical limonoid limonin

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. [1] Certain limonoids are antifeedants such as azadirachtin from the neem tree. [2]

Chemically, the limonoids consist of variations of the furanolactone core structure. The prototypical structure consists of four six-membered rings and a furan ring. Limonoids are classed as tetranortriterpenes.

Citrus fruits contain the limonoids limonin, nomilin and nomilinic acid, while both neem seeds and leaves contain the limonoid azadirachtin, although higher concentrations are present in the former.

See also

Related Research Articles

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

Azadirachta indica, commonly known as margosa, neem, 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 northeast of the Indian subcontinent and to Indochina, but is naturalized and grown around the world in tropical and subtropical areas. Its fruits and seeds are the source of neem oil. Nīm (नीम/نیم) is a Hindustani noun derived from Sanskrit nimba (निंब).

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

Citrus is a genus of flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as oranges, lemons, grapefruits, pomelos, and limes. The genus Citrus is native to South Asia, East Asia, Southeast Asia, Melanesia, and Australia. Various citrus species have been used and domesticated by indigenous cultures in these areas since ancient times. From there its cultivation spread into Micronesia and Polynesia by the Austronesian expansion ; and to the Middle East and the Mediterranean via the incense trade route, and onwards to Europe and the Americas.

The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.

<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">Lime (fruit)</span> Citrus fruit

A lime is a citrus fruit, which is typically round, green in color, 3–6 centimetres (1.2–2.4 in) in diameter, and contains acidic juice vesicles.

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

The tetranortriterpenoid class of naturally occurring organic compounds, of which the most noted compound is azadirachtin, extracted from the neem tree that displays insecticidal properties. Azadirachtin mimics insect hormones called ecdysones that regulate pupation of insects; application of azadirachtin interrupts the development and pupation of insects, which eventually kills them.

<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.

Grapefruit seed extract (GSE), also known as citrus seed extract, is a liquid extract derived from the seeds, pulp, and white membranes of grapefruit. GSE is prepared by grinding the grapefruit seed and juiceless pulp, then mixing with glycerin. Commercially available GSEs sold to consumers are made from the seed, pulp, and glycerin blended together. GSE is sold as a dietary supplement and is used in cosmetics.

Neem cake organic manure is the by-product obtained in the process of cold pressing of neem tree fruits and kernels, and the solvent extraction process for neem oil cake. It is a potential source of organic manure under the Bureau of Indian Standards, Specification No. 8558. Neem has demonstrated considerable potential as a fertilizer. For this purpose, neem cake and neem leaves are especially promising. Puri (1999), in his book on neem, has given details about neem seed cake as manure and nitrification inhibitor. The author has described that, after processing, neem cake can be used for partial replacement of poultry and cattle feed.

<span class="mw-page-title-main">Orange (fruit)</span> Citrus fruit

An orange is a fruit of various citrus species in the family Rutaceae ; it primarily refers to Citrus × sinensis, which is also called sweet orange, to distinguish it from the related Citrus × aurantium, referred to as bitter orange. The sweet orange reproduces asexually ; varieties of the sweet orange arise through mutations.

<span class="mw-page-title-main">Sesquiterpene</span> Class of terpenes

Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids.

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

Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones.

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

Bergapten (5-methoxypsoralen) is a naturally-occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae. In the family Rutaceae, various Citrus species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.

<span class="mw-page-title-main">Aspiviridae</span> Family of viruses

Aspiviridae, formerly Ophioviridae, is a family of segmented negative-strand RNA viruses which infect plants. Member viruses are characterized by an elongated and highly filamentous and flexible nucleocapsid with helical symmetry. It is a monotypic taxon containing only one genus, Ophiovirus. Aspiviridae is also the only family in the order Serpentovirales, which in turn is the only order in the class Milneviricetes.

<i>Spodoptera eridania</i> Species of moth

Spodoptera eridania is a moth that is known to be a pest. They are one of the most important defoliators in the tropical and subtropical regions of the western hemisphere that feed heavily on plants while they are young, often resulting in skeleton leaves on their food plants. They are also heavy feeders on tomato in Florida. There is a lot of development in producing pesticides against the S. eridania, specifically a neem-based pesticide that can result in smaller and prolonged development. The wingspan is 33–38 mm. Adults are on wing year-round. The larvae feed on various weeds but prefer Amaranthus species and Phytolacca americana.

<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">Antifeedant</span>

Antifeedants are organic compounds produced by plants to repel herbivores through distaste or toxicity. These chemical compounds are typically classified as secondary metabolites in that they are not essential for the metabolism of the plant, but instead confer longevity. Antifeedants exhibit a wide range of activities and chemical structures as biopesticides. Examples include rosin, which inhibits attack on trees, and many alkaloids, which are highly toxic to specific insect species.

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

Gedunin is a pentacyclic triterpenoid with the molecular formula C28H43O7. It is most notably found in Azadirachta indica, but is a constituent of several other plants. Gedunin shows therapeutic potential in the treatment of leukemia, and Parkinson's disease.

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

Pyranocoumarins are a class of chemical compounds that have a core structure that consists of a pyran ring fused to a coumarin. As phytochemicals, pyranocoumarins are uncommon and found mainly the plant families Apiaceae and Rutaceae. For example, Citrus sinensis and Citrus limonia are sources of xanthyletin and seselin.

References

  1. Amit Roy and Shailendra Saraf (2006). "Limonoids: Overview of Significant Bioactive Triterpenes Distributed in Plants Kingdom". Biol. Pharm. Bull. 29 (2): 191–201. doi: 10.1248/bpb.29.191 . PMID   16462017.
  2. Donald E.Champagne; Opender Koul; Murray B. Isman; Geoffrey G. E.Scudder; G. H. Neil Towers (1992). "Biological activity of limonoids from the rutales". Phytochemistry. 31 (2): 377–394. doi:10.1016/0031-9422(92)90003-9.