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Glucuronides
A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides. Glucuronidation, the conversion of chemical compounds to glucuronides, is a method that animals use to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. Enzymes that cleave the glycosidic bond of a glucuronide are called glucuronidases. Classes of glucuronides Acyl glucuronide Carboxylic acids are a common functional group in many medications, such as NSAIDS, anticonvulsants, and diuretics. One common pathway for the clearance of carboxylic-acid-containing drugs is via glucuronidation. By conjugating one such drug to a glucuro ...
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Quercetin
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. Occurrence Quercetin is a flavonoid widely distributed in nature. The name has been used since 1857, and is derived from ''quercetum'' (oak forest), after the oak genus ''Quercus''. It is a naturally occurring polar auxin transport inhibitor. Quercetin is one of the most abundant dietary flavonoids, with an average daily consumption of 25–50 mg. In red onions, higher concentrations of quercetin occur in the outermost rings and in the part closest to the root, the latter being the part of the plant with the highest concentration. One study found that organically grown tomatoes had 79% more quercetin than non-organically grown fruit. Quercetin is present in ...
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Glucuronic Acid
Glucuronic acid (GCA, from ) is a uronic acid that was first isolated from urine (hence the name "uronic acid"). It is found in many natural gum, gums such as gum arabic ( 18%), xanthan, and kombucha tea and is important for the metabolism of microorganisms, plants and animals. Properties Glucuronic acid is a sugar acid derived from glucose, with its sixth carbon atom oxidized to a carboxylic acid. In living beings, this primary oxidation occurs with Uridine diphosphate glucose, UDP-α-D-glucose (UDPG), not with the free sugar. Glucuronic acid, like its precursor glucose, can exist as a linear (carboxo-)aldohexose ( 60,000 are too large for renal excretion and will be excreted with bile into the intestine. Neonates are deficient in this conjugating system, making them particularly vulnerable to drugs such as chloramphenicol, which is inactivated by the addition of glucuronic acid, resulting in gray baby syndrome. Bilirubin is excreted in the bile as bilirubin diglucuronid ...
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Morphine-6-glucuronide
Morphine-6-glucuronide (M6G) is a major active metabolite of morphine. M6G is formed from morphine by the enzyme UGT2B7. It has analgesic effects roughly half that of morphine. M6G can accumulate to toxic levels in kidney failure. History of discovery This analgesic activity of M6G (in animals) was first noted by Yoshimura. Subsequent work at St Bartholomew's Hospital, London in the 1980s, using a sensitive and specific high-performance liquid chromatography assay, accurately defined for the first time the metabolism of morphine, and the abundance of this metabolite (along with morphine-3-glucuronide, considered an inactive metabolite). It was postulated that kidney impairment would result in accumulation of the kidney-excreted active agent M6G, leading to potentially fatal toxicity such as respiratory depression. The frequent use of morphine in critically ill patients, and the common occurrence of kidney failure in this group implied that M6G accumulation could be a common ...
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Scutellarein-7-glucuronide
Scutellarin is a flavone, a type of phenolic chemical compound. It can be found in the Asian "barbed skullcap" '' Scutellaria barbata'' and the north American plant '' S. lateriflora'' both of which have been used in traditional medicine. The compound is found only in trace amounts in the "Chinese skullcap" '' Scutellaria baicalensis'', another plant used in traditional Chinese medicine. The determination of the structure of scutellarin took Guido Goldschmiedt many years: after the first publication on that topic in 1901, only in 1910 he managed to obtain enough starting material for more detailed studies. Scutellarin has anticancer properties. It has been found to induce apoptosis of ovarian and breast tumor cells ''in vitro''. One mechanism of scutellarin's antitumor action is to bind to TNF receptor II (TNFR2) in tumor-associated CD4+Foxp3+ regulatory T cells. These tumor "helper" cells show high expression of TNFR2 and are inhibited when it is blocked by scutellarin. Scutel ...
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Glycoside
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 enzymatic, 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. In formal terms, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an ''O-glycoside''), N- (a ''glycosylamine''), S-(a ''thioglycoside''), or C- (a ''C-glycoside'') glycosidic bond. Accord ...
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Miquelianin
Miquelianin (quercetin 3-''O''-glucuronide) is a flavonol glucuronide, a type of phenolic compound present in wine, in species of St John's wort, like '' Hypericum hirsutum'', in ''Nelumbo nucifera'' (Indian lotus) or in green beans. It is also a rat plasma quercetin metabolite. It shows an antioxidant effect in human plasma. In vitro studies indicate that miquelianin is able to reach the central nervous system from the small intestine. See also * Phenolic content in wine Phenolic compounds— natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilb ... References Flavonoid glucuronides Glucuronide esters Quercetin glycosides {{aromatic-stub ...
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Anticonvulsant
Anticonvulsants (also known as antiepileptic drugs, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also used in the treatment of bipolar disorder and borderline personality disorder, since many seem to act as mood stabilizers, and for the treatment of neuropathic pain. Anticonvulsants suppress the uncontrolled and excessive firing of neurons during seizures and in doing so can also prevent the spread of the seizure within the brain. Conventional antiepileptic drugs have diverse mechanisms of action but many block sodium channels or enhance γ-aminobutyric acid ( GABA) function. Several antiepileptic drugs have multiple or uncertain mechanisms of action. Next to voltage-gated sodium channels and components of the GABA system, their targets include GABAA receptors, the GABA transporter type 1, and GABA transaminase. Additional targets include voltage-gate ...
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Nicotine
Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is used for smoking cessation to relieve drug withdrawal, withdrawal symptoms. Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs), except at two nicotinic receptor subunits (nAChRα9 and nAChRα10) where it acts as a receptor antagonist. Nicotine constitutes approximately 0.6–3.0% of the dry weight of tobacco. Nicotine is also present at Parts-per notation, ppb concentrations in edible plants in the family Solanaceae, including potatoes, tomatoes, and eggplants, though sources disagree on whether this has any biological significance to human consumers. It functions as an plant defense against herbivory, antiherbivore toxin; consequently, nicotine was widely used as an insecti ...
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Diuretic
A diuretic () is any substance that promotes diuresis, the increased production of urine. This includes forced diuresis. A diuretic tablet is sometimes colloquially called a water tablet. There are several categories of diuretics. All diuretics increase the excretion of water from the body, through the kidneys. There exist several classes of diuretic, and each works in a distinct way. Alternatively, an antidiuretic, such as vasopressin ( antidiuretic hormone), is an agent or drug which reduces the excretion of water in urine. Medical uses In medicine, diuretics are used to treat heart failure, liver cirrhosis, hypertension, influenza, water poisoning, and certain kidney diseases. Some diuretics, such as acetazolamide, help to make the urine more alkaline, and are helpful in increasing excretion of substances such as aspirin in cases of overdose or poisoning. Diuretics are sometimes abused by people with an eating disorder, especially people with bulimia nervosa, with the ...
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Morphine 6-glucuronide
Morphine, formerly also called morphia, is an opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (''Papaver somniferum''). It is mainly used as an analgesic (pain medication). There are multiple methods used to administer morphine: oral; sublingual; via inhalation; injection into a muscle, injection under the skin, or injection into the spinal cord area; transdermal; or via rectal suppository. It acts directly on the central nervous system (CNS) to induce analgesia and alter perception and emotional response to pain. Physical and psychological dependence and tolerance may develop with repeated administration. It can be taken for both acute pain and chronic pain and is frequently used for pain from myocardial infarction, kidney stones, and during labor. Its maximum effect is reached after about 20 minutes when administered intravenously and 60 minutes when administered by mouth, while the duration of its effect ...
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