Names | |
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IUPAC name 5,7-Dihydroxy-6-methoxyflavone | |
Systematic IUPAC name 5,7-Dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one | |
Other names Baicalein 6-methyl ether | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.189.623 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C16H12O5 | |
Molar mass | 284.26 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Oroxylin A is an O-methylated flavone, a chemical compound that can be found in the medicinal plants Scutellaria baicalensis [1] and Scutellaria lateriflora , [2] [3] and the Oroxylum indicum tree. [4] It has demonstrated activity as a dopamine reuptake inhibitor, [5] and is also a negative allosteric modulator of the benzodiazepine site of the GABAA receptor. [5] [6] [7] Oroxylin A has been found to improve memory consolidation in mice by elevating brain-derived neurotrophic factor (BDNF) levels in the hippocampus. [8]
A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dopamine not absorbed by the postsynaptic neuron is blocked from re-entering the presynaptic neuron. This results in increased extracellular concentrations of dopamine and increase in dopaminergic neurotransmission.
Scutellaria is a genus of flowering plants in the mint family, Lamiaceae. They are known commonly as skullcaps. The generic name is derived from the Latin scutella, meaning "a small dish, tray or platter", or "little dish", referring to the shape of the calyx. The common name alludes to the resemblance of the same structure to "miniature medieval helmets". The genus has a subcosmopolitan distribution, with species occurring nearly worldwide, mainly in temperate regions.
Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.
Chrysin, also called 5,7-dihydroxyflavone, is a flavone found in honey, propolis, the passion flowers, Passiflora caerulea and Passiflora incarnata, and in Oroxylum indicum. It is extracted from various plants, such as the blue passion flower. Following oral intake by humans, chrysin has low bioavailability and rapid excretion. It is under basic research to evaluate its safety and potential biological effects.
Scutellaria baicalensis, with the common name Baikal skullcap or Chinese skullcap, is a species of flowering plant in the family Lamiaceae.
Scutellaria lateriflora, is a hardy perennial herb of the mint family, Lamiaceae, native to North America.
A serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), also known as a triple reuptake inhibitor (TRI), is a type of drug that acts as a combined reuptake inhibitor of the monoamine neurotransmitters serotonin, norepinephrine, and dopamine. It does this by concomitantly inhibiting the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT), respectively. Inhibition of the reuptake of these neurotransmitters increases their extracellular concentrations and, therefore, results in an increase in serotonergic, adrenergic, and dopaminergic neurotransmission. The naturally-occurring and potent SNDRI cocaine is widely used recreationally and often illegally for the euphoric effects it produces.
N-alpha-acetyltransferase 10 (NAA10) also known as NatA catalytic subunit Naa10 and arrest-defective protein 1 homolog A (ARD1A) is an enzyme subunit that in humans is encoded NAA10 gene. Together with its auxiliary subunit Naa15, Naa10 constitutes the NatA complex that specifically catalyzes the transfer of an acetyl group from acetyl-CoA to the N-terminal primary amino group of certain proteins. In higher eukaryotes, 5 other N-acetyltransferase (NAT) complexes, NatB-NatF, have been described that differ both in substrate specificity and subunit composition.
As baicalin is a flavone glycoside, it is a flavonoid. It is the glucuronide of baicalein.
Baicalein (5,6,7-trihydroxyflavone) is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis and Scutellaria lateriflora. It is also reported in Oroxylum indicum and Thyme. It is the aglycone of baicalin. Baicalein is one of the active ingredients of Sho-Saiko-To, which is a Chinese classic herbal formula, and listed in Japan as Kampo medicine.
RTI(-4229)-113 is a stimulant drug which acts as a potent and fully selective dopamine reuptake inhibitor (DRI). It has been suggested as a possible substitute drug for the treatment of cocaine addiction. "RTI-113 has properties that make it an ideal medication for cocaine abusers, such as an equivalent efficacy, a higher potency, and a longer duration of action as compared to cocaine." Replacing the methyl ester in RTI-31 with a phenyl ester makes the resultant RTI-113 fully DAT specific. RTI-113 is a particularly relevant phenyltropane cocaine analog that has been tested on squirrel monkeys. RTI-113 has also been tested against cocaine in self-administration studies for DAT occupancy by PET on awake rhesus monkeys. The efficacy of cocaine analogs to elicit self-administration is closely related to the rate at which they are administered. Slower onset of action analogs are less likely to function as positive reinforcers than analogues that have a faster rate of onset.
Wogonin is an O-methylated flavone, a flavonoid-like chemical compound which is found in Scutellaria baicalensis.
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.
Cerebral dopamine neurotrophic factor also known as ARMET-like protein 1 is a protein that in humans is encoded by the CDNF gene.
Visnagin is an organic chemical compound with the molecular formula C13H10O4 It is a furanochromone, a compound derivative of chromone (1,4-benzopyrone) and furan.
Baicalin-beta-D-glucuronidase (EC 3.2.1.167, baicalinase) is an enzyme with systematic name 5,6,7-trihydroxyflavone-7-O-beta-D-glucupyranosiduronate glucuronosylhydrolase. This enzyme catalyses the following chemical reaction
Homoisoflavonoids (3-benzylidenechroman-4-ones) are a type of phenolic compounds occurring naturally in plants.
Lobeglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. As an agonist for both PPARα and PPARγ, it works as an insulin sensitizer by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin.
Tropoflavin, also known as 7,8-dihydroxyflavone, is a naturally occurring flavone found in Godmania aesculifolia, Tridax procumbens, and primula tree leaves. It has been found to act as a potent and selective small-molecule agonist of the tropomyosin receptor kinase B (TrkB), the main signaling receptor of the neurotrophin brain-derived neurotrophic factor (BDNF). Tropoflavin is both orally bioavailable and able to penetrate the blood–brain barrier. A prodrug of tropoflavin with greatly improved potency and pharmacokinetics, R13, is under development for the treatment of Alzheimer's disease.
5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one (DMPC) is a derivative of Oroxylin A.It has memory improving effects and can reduce ADHD-like behavior.