Names | |
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IUPAC name 3-(β-D-Glucopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone | |
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one | |
Other names Isoquercitroside Isoquercitrin Isoquercetin Trifoliin Isotrifolin Trifoliin A Isohyperoside Isotrifoliin Quercetin-3-glucoside Quercetin-3-O-glucoside Quercetin 3-O-β-D-glucopyranoside | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.123.856 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C21H20O12 | |
Molar mass | 464.379 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isoquercetin, isoquercitrin or isotrifoliin [1] is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including Mangifera indica (mango) [2] and Rheum nobile (the Noble rhubarb). It is also present in the leaves of Annona squamosa , Camellia sinensis (tea). [3] [4] and Vestia foetida [5]
The lambda-max for isoquercetin is 254.8 and 352.6 nm.
Isoquercetin is presently being investigated for prevention of thromboembolism in selected cancer patients [6] and as an anti-fatigue agent in kidney cancer patients treated with sunitinib. [7]
There is a single case report of its use in the successful treatment of prurigo nodularis, a difficult to treat pruritic eruption of the skin. [8]
However it belongs to the PAINS (Pan-assay interference compounds) categories of chemicals. [9]
Disulfiram is a medication used to support the treatment of chronic alcoholism by producing an acute sensitivity to ethanol. Disulfiram works by inhibiting the enzyme aldehyde dehydrogenase, causing many of the effects of a hangover to be felt immediately following alcohol consumption. Disulfiram plus alcohol, even small amounts, produces flushing, throbbing in the head and neck, a throbbing headache, respiratory difficulty, nausea, copious vomiting, sweating, thirst, chest pain, palpitation, dyspnea, hyperventilation, fast heart rate, low blood pressure, fainting, marked uneasiness, weakness, vertigo, blurred vision, and confusion. In severe reactions there may be respiratory depression, cardiovascular collapse, abnormal heart rhythms, heart attack, acute congestive heart failure, unconsciousness, convulsions, and death.
Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.
Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.
Annona squamosa is a small, well-branched tree or shrub from the family Annonaceae that bears edible fruits called sugar apples or sweetsops. It tolerates a tropical lowland climate better than its relatives Annona reticulata and Annona cherimola helping make it the most widely cultivated of these species. Annona squamosa is a small, semi-(or late) deciduous, much-branched shrub or small tree 3 to 8 metres tall similar to soursop. It is a native of tropical climate in the Americas and West Indies, and Spanish traders aboard the Manila galleons docking in the Philippines brought it to Asia.
Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed polyphenols.
Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.
Prurigo nodularis (PN), also known as nodular prurigo, is a skin disorder characterized by pruritic (itchy), nodular lesions, which commonly appear on the trunk, arms and legs. Patients often present with multiple excoriated nodules caused by chronic scratching. Although the exact cause of PN is unknown, PN is associated with other dermatologic conditions such as untreated or severe atopic dermatitis and systemic causes of pruritus including liver disease and end stage kidney disease. The goal of treatment in PN is to decrease itching. PN is also known as Hyde prurigo nodularis, or Picker's nodules.
Dasatinib, sold under the brand name Sprycel among others, is a targeted therapy medication used to treat certain cases of chronic myelogenous leukemia (CML) and acute lymphoblastic leukemia (ALL). Specifically it is used to treat cases that are Philadelphia chromosome-positive (Ph+). It is taken by mouth.
Annonacin is a chemical compound with toxic effects, especially in the nervous system, found in some fruits such as the paw paw, custard apples, soursop, and others from the family Annonaceae. It is a member of the class of compounds known as acetogenins. Annonacin-containing fruit products are regularly consumed throughout the West Indies for their traditional medicine uses.
Semustine is an alkylating nitrosourea compound used in chemotherapy treatment of various types of tumours. Due to its lipophilic property, semustine can cross the blood-brain barrier for the chemotherapy of brain tumours, where it interferes with DNA replication in the rapidly-dividing tumour cells. Semustine, just as lomustine, is administered orally. Evidence has been found that treatment with semustine can cause acute leukaemia as a delayed effect in very rare cases.
Spiraeoside is a chemical compound. It can be isolated from flowers of Filipendula ulmaria (L.) or from the garden onion.
Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols. It is extracted from plants such as Siberian larch and milk thistle.
Cynaroside is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin.
Mangiferin is a glucosylxanthone (xanthonoid). This molecule is a glucoside of norathyriol.
Dupilumab, sold under the brand name Dupixent, is a monoclonal antibody blocking interleukin 4 and interleukin 13, used for allergic diseases such as atopic dermatitis (eczema), asthma and nasal polyps which result in chronic sinusitis. It is also used for the treatment of eosinophilic esophagitis and prurigo nodularis.
Vestia is a monotypic genus of flowering plants in the family Solanaceae containing the single species Vestia foetida (syn. V. lycioides). Its principal common names in the Mapudungun language of its native Chile are Huevil (pron. "wayfil" and sometimes redoubled Huevilhuevil) and Chuplín. Other Chilean names include Chuplí, Echuelcún and Palqui (negro) (this last being also applied to Cestrum parqui), while an English common name Chilean box thorn has also been coined recently in reference to a certain similarity of the plant to some species in the box thorn / wolfberry genus Lycium (as referenced also in the former specific name lycioides, meaning "Lycium-like"). Vestia foetida is endemic to central and southern Chile, being found in an area stretching from the Valparaíso Region in the north to Chiloé Island (in the Los Lagos Region) in the south. Growing to 2 m (7 ft) tall by 1.5 m (5 ft) broad, it is an evergreen shrub with glossy, privet-like, mid-green leaves. In spring and summer it bears tubular yellow flowers to 3 cm (1 in) long, with stamens so markedly exserted (= protruding) as to recall those of certain Fuchsia species, followed by 4-valved, ovoid capsules to 1 cm (0 in), containing small, prismatic seeds.
Anonaine is a bioactive benzylisoquinoline alkaloid, present in members of the plant families Magnoliaceae and Annonaceae It is named after the plant it was first extracted from, Annona reticulata, which is commonly known as Anona.
Quadrosilan is a synthetic nonsteroidal estrogen that was developed in the 1970s and that is or has been used as an antigonadotropic agent in the treatment of prostate cancer. It is an organosilicon compound, and is also known as 2,6-cisdiphenylhexamethylcyclotetrasiloxane. Quadrosilan has estrogenic activity equivalent to that of estradiol, and can produce feminization and gynecomastia as side effects in male patients.
Nemolizumab, sold under the brand name Nemluvio, is a medication for the treatment of prurigo nodularis. It is a monoclonal antibody that blocks the interleukin-31 receptor A.