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Names | |
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IUPAC name [(5R,7R,8R,9R,10R,13S,17R)-17-(Furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate | |
Other names 24-Norchola-1,14,20,22-tetraene-3,16-dione, 7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,17alpha)- | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
MeSH | azadiradione |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C28H34O5 | |
Molar mass | 450.575 g·mol−1 |
Density | 1.2±0.1 g/cm3 |
Vapor pressure | 0.0±1.5 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Azadiradione is a naturally occurring compound found in several plants, most notably the neem tree ( Azadirachta indica ). It is a tetracyclic triterpenoid.
Azadiradione is the principal active ingredient in neem oil, which is extracted from the seeds of the neem tree. Smaller quantities of azadiradione can also be found in other plants like Cedrela odorata (Spanish cedar), Chisocheton siamensis , Xylocarpus granatum (cannonball mangrove) and Azalea indica (common azalea).
Azadiradione acts as an antioxidant and has been used in traditional medicine in Asia, Africa and the Middle East for ages. [1]
Research suggests azadiradione may have properties that fight microbes (bacteria, fungi, viruses), [2] reduce inflammation, protect cells from damage, [3] and even have anti-cancer effects. [4] [5] [6] [7]
Azadiradione may also act as a natural pesticide, potentially controlling some insects and pests. [8]
Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants are frequently added to industrial products, such as polymers, fuels, and lubricants, to extend their usable lifetimes. Foods are also treated with antioxidants to forestall spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol, or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress.
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 is a Hindustani noun derived from Sanskrit nimba (निंब).
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.
In chemistry and biology, reactive oxygen species (ROS) are highly reactive chemicals formed from diatomic oxygen (O2), water, and hydrogen peroxide. Some prominent ROS are hydroperoxide (O2H), superoxide (O2-), hydroxyl radical (OH.), and singlet oxygen. ROS are pervasive because they are readily produced from O2, which is abundant. ROS are important in many ways, both beneficial and otherwise. ROS function as signals, that turn on and off biological functions. They are intermediates in the redox behavior of O2, which is central to fuel cells. ROS are central to the photodegradation of organic pollutants in the atmosphere. Most often however, ROS are discussed in a biological context, ranging from their effects on aging and their role in causing dangerous genetic mutations.
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.
The vitamin E family comprises four tocotrienols and four tocopherols. The critical chemical structural difference between tocotrienols and tocopherols is that tocotrienols have unsaturated isoprenoid side chains with three carbon-carbon double bonds versus saturated side chains for tocopherols.
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 Neem : The Divine Tree Azadirachta, 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.
Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach, and broccoli. Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.
Trametes versicolor – also known as Coriolus versicolor and Polyporus versicolor – is a common polypore mushroom found throughout the world. Meaning 'of several colors', versicolor accurately describes this fungus that displays a unique blend of markings. Additionally, owing to its shape being similar to that of a wild turkey's tail feathers, T. versicolor is most commonly referred to as turkey tail. A similar-looking mushroom commonly called "false turkey tail" is from a different order (Stereum), and thus may sometimes be confused with the 'true' turkey tail mushroom, T. versicolor. Another lookalike is the multicolor gill polypore, T. betulina.
Wolfiporia extensa(syn.Poria cocos F.A.Wolf), commonly known as hoelen, poria, tuckahoe, China root, fu ling, or matsuhodo, is a fungus in the family Polyporaceae. It is a wood-decay fungus but has a subterranean growth habit. It is notable in the development of a large, long-lasting underground sclerotium that resembles a small coconut. This sclerotium, known as Tuckahoe or fu-ling, is not the same as the true tuckahoe used as Indian bread by Native Americans, which is the arrow arum, Peltandra virginica, a flowering tuberous plant in the arum family.
Tricetin is a flavone, a type of flavonoid. It is a rare aglycone found in the pollen of members of the Myrtaceae, subfamily Leptospermoideae, such as Eucalyptus globulus. This compound shows anticancer effects on human breast adenocarcinoma MCF-7 cells. Moreover. a potent anti-inflammatory effect of tricetin has also been demonstrated in a model of acute pancreatitis. This observation was explained by the compound's radical scavenging effects, its inhibitory effect on the DNA damage sensor enzyme poly (ADP-ribose) polymerase-1 (PARP1) and PARP1-mediated cell death and suppression of inflammatory gene expression.
Fisetin (7,3′,4′-flavon-3-ol) is a plant flavonol from the flavonoid group of polyphenols. It can be found in many plants, where it serves as a yellow/ochre colouring agent. It is also found in many fruits and vegetables, such as strawberries, apples, persimmons, onions and cucumbers. Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.
Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.
Lupeol is a pharmacologically active pentacyclic triterpenoid. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.
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.
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.
Brequinar (DuP-785) is a drug that acts as a potent and selective inhibitor of the enzyme dihydroorotate dehydrogenase. It blocks synthesis of pyrimidine based nucleotides in the body and so inhibits cell growth. Brequinar was invented by DuPont Pharmaceuticals in the 1980s. In 2001, Bristol-Myers Squibb acquired DuPont, and in 2017, Clear Creek Bio acquired the rights to brequinar from BMS.
Hinokinin is a dibenzylbutyrolactone lignan, derived from various species of plants. It is a potential antichagonistic agent. In vitro, it has been shown to have potential neuroprotective effects as well as anti-inflammatory, anti-tumor, antiviral and antifungal properties.
Tragia volubilis also known as fireman is a climbing subshrub or climbing shrub native to tropical America and Africa. It belongs to the Euphorbiaceae family, Tragia genus. As many of the species of the genus, it has stinging hairs, similar to those of nettles.
Gedunin is a pentacyclic triterpenoid with the molecular formula C28H34 O7. 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.