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Limonoids
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.{{cite journal, title=Biological activity of limonoids from the rutales, journal=Phytochemistry, volume=31, pages=377–394, authors=Donald E.Champagne, Opender Koul, Murray B. Isman, Geoffrey G. E.Scudder, G. H. Neil Towers, year=1992, issue=2, doi=10.1016/0031-9422(92)90003-9 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 * Tetranortriterpenoid The ...
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Neem
''Azadirachta indica'', commonly known as neem, nimtree or Indian lilac, is a tree in the mahogany family Meliaceae. It is one of two species in the genus ''Azadirachta'', and is native to the Indian subcontinent and most of the countries in Africa. It is typically grown in tropical and semi-tropical regions. Neem trees also grow on islands in southern Iran. Its fruits and seeds are the source of neem oil. Description Neem is a fast-growing tree that can reach a height of , and rarely . It is deciduous, shedding many of its leaves during the dry winter months. The branches are wide and spreading. The fairly dense crown is roundish and may reach a diameter of . The neem tree is similar in appearance to its relative, the chinaberry (''Melia azedarach''). The opposite, pinnate leaves are long, with 20 to 30 medium to dark green leaflets about long. The terminal leaflet often is missing. The petioles are short. White and fragrant flowers are arranged in more-or-less drooping a ...
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Azadirachtin
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. Chemical synthesis Azadirachtin has a complex molecular structure; it presents both secondary and tertiary hydroxyl groups and a tetrahydrofuran ether in its molecular structure, alongside 16 stereogenic centres, 7 of which are tetrasubstituted. These characteristics explain the great difficulty encountered when trying to prepare this compound from simple precursors, using methods of synthetic organic chemistry. Hence, the first total synthesis was published over 22 years after the compound's discovery: this first synthesis was completed by the research group of Steven Ley at the University of Cambridge in 2007. The described synthesis was a relay approach ...
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Limonin
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. Sources Limonin is enriched in citrus fruits and is often found at higher concentrations in seeds, for example orange and lemon seeds. Presence in citrus products Limonin and other limonoid compounds contribute to the bitter taste of some citrus food products. Researchers have proposed removal of limonoids from orange juice and other products (known as "debittering") through the use of polymeric films. Research Limonin is under basic research Basic research, also called pure research or fundamental research, is a type of scientific research with the aim of improving scientific theories for better understanding and prediction of natural or other phenomena. In contrast, applied resear ... to assess its possible biologica ...
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Limonin
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. Sources Limonin is enriched in citrus fruits and is often found at higher concentrations in seeds, for example orange and lemon seeds. Presence in citrus products Limonin and other limonoid compounds contribute to the bitter taste of some citrus food products. Researchers have proposed removal of limonoids from orange juice and other products (known as "debittering") through the use of polymeric films. Research Limonin is under basic research Basic research, also called pure research or fundamental research, is a type of scientific research with the aim of improving scientific theories for better understanding and prediction of natural or other phenomena. In contrast, applied resear ... to assess its possible biologica ...
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Cucurbitaceae
The Cucurbitaceae, also called cucurbits or the gourd family, are a plant family consisting of about 965 species in around 95 genera, of which the most important to humans are: *''Cucurbita'' – squash, pumpkin, zucchini, some gourds *''Lagenaria'' – calabash, and others that are inedible *''Citrullus'' – watermelon (''C. lanatus'', ''C. colocynthis'') and others *''Cucumis'' – cucumber (''C. sativus''), various melons and vines *''Momordica'' – bitter melon *''Luffa'' – the common name is also luffa, sometimes spelled loofah (when fully ripened, two species of this fibrous fruit are the source of the loofah scrubbing sponge) *''Cyclanthera'' – Caigua The plants in this family are grown around the tropics and in temperate areas, where those with edible fruits were among the earliest cultivated plants in both the Old and New Worlds. The family Cucurbitaceae ranks among the highest of plant families for number and percentage of species used as human food. The name ' ...
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Rutaceae
The Rutaceae is a family, commonly known as the rueRUTACEAE
in BoDD – Botanical Dermatology Database
or family, of s, usually placed in the order . Species of the family generally have s that divide into four or five parts, usually w ...
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Meliaceae
Meliaceae, the mahogany family, is a flowering plant family of mostly trees and shrubs (and a few herbaceous plants, mangroves) in the order Sapindales. They are characterised by alternate, usually pinnate leaves without stipules, and by syncarpous, apparently bisexual (but actually mostly cryptically unisexual) flowers borne in panicles, cymes, spikes, or clusters. Most species are evergreen, but some are deciduous, either in the dry season or in winter. The family includes about 53 genera and about 600 known species, with a pantropical distribution; one genus (''Toona'') extends north into temperate China and south into southeast Australia, another (''Synoum'') into southeast Australia, and another (''Melia'') nearly as far north. They most commonly grow as understory trees in rainforests, but are also found in mangroves and arid regions. The fossil record of the family extends back into the Late Cretaceous. Uses Various species are used for vegetable oil, soap-making, ins ...
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Antifeedant
Antifeedants are organic compounds produced by plants to inhibit attack by insects and grazing animals. 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. History "Plant-derived insecticides (e.g., rotenone, veratridines, pyrethrins, and nicotine) have been used for insect control since antiquity." The active ingredients in these plants have been purified and modified. For example, variations on pyrethrin has spawned a large number of synthetic insecticides call pyrethroids. Culinary implications In addition to their role defending the plant, antifeedants often confer taste or odors, enhancing the flavor of certain plants. Examples are provided by ...
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Citrus
''Citrus'' is a genus of flowering plant, flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as Orange (fruit), oranges, Lemon, lemons, grapefruits, pomelos, and lime (fruit), limes. The genus ''Citrus'' is native to South Asia, East Asia, Southeast Asia, Melanesia, and Australia (continent), 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 (c. 3000–1500 BCE); and to the Middle East and the Mediterranean (c. 1200 BCE) via the incense trade route, and onwards to Europe and the Americas. History Citrus plants are native to subtropical and tropical regions of Asia, Island Southeast Asia, Near Oceania, and northeastern Australia. Domestication of citrus species involved much hybridization and introgression, leaving much uncertainty ab ...
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Phytochemicals
Phytochemicals are chemical compounds produced by plants, generally to help them resist fungi, bacteria and plant virus infections, and also consumption by insects and other animals. The name comes . Some phytochemicals have been used as poisons and others as traditional medicine. As a term, ''phytochemicals'' is generally used to describe plant compounds that are under research with unestablished effects on health, and are not scientifically defined as essential nutrients. Regulatory agencies governing food labeling in Europe and the United States have provided guidance for industry to limit or prevent health claims about phytochemicals on food product or nutrition labels. Definition Phytochemicals are chemicals of plant origin. Phytochemicals (from Greek ''phyto'', meaning "plant") are chemicals produced by plants through primary or secondary metabolism. They generally have biological activity in the plant host and play a role in plant growth or defense against competitors ...
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Furanolactone
A furanolactone is a heterocyclic chemical compound that contains both a lactone and a furan ring structure. Examples include: * The salvinorins, including the hallucinogenic compound salvinorin A * Columbin, a bitter diterpenoid from '' Calumbae Radix'' * Limonoids such as limonin, nomilin, and nomilinic acid * Tinosporide, a diterpenoid originally isolated from ''Tinospora cordifolia ''Tinospora cordifolia'' (common names gurjo, heart-leaved moonseed, guduchi or giloy) is a herbaceous vine of the family Menispermaceae indigenous to tropical regions of the Indian subcontinent. It has been used in Ayurveda to treat various diso ...'' References {{reflist Lactones 3-Furyl compounds ...
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Furan
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans. Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is soluble in common organic solvents, including alcohol, ether, and acetone, and is slightly soluble in water. Its odor is "strong, ethereal; chloroform-like". It is toxic and may be carcinogenic in humans. Furan is used as a starting point for other speciality chemicals. History The name "furan" comes from the Latin ''furfur'', which means bran. ( Furfural is produced from bran.) The first furan derivative to be described was 2-furoic acid, by Carl Wilhelm Scheele in 1780. Another important derivative, furfural, was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John Stenhouse. Furan itself was first prepared by Heinrich Lim ...
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