Names | |
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IUPAC name (2S)-5,7-Dihydroxy-4′-methoxyflavan-4-one | |
Systematic IUPAC name (2S)-5,7-Dihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | |
Other names 4'-Methylnaringenin | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.866 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C16H14O5 | |
Molar mass | 286.27 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isosakuranetin, an O-methylated flavonoid, is the 4'-methoxy derivative of naringenin, a flavanone. Didymin, a disaccharide of isosakuranetin, occur e.g. in sweet orange, blood orange and mandarin. [1] Isosakuranetin is a potent inhibitor of TRPM3 channels. [2]
Transient receptor potential channels are a group of ion channels located mostly on the plasma membrane of numerous animal cell types. Most of these are grouped into two broad groups: Group 1 includes TRPC, TRPV, TRPVL, TRPM, TRPS, TRPN, and TRPA. Group 2 consists of TRPP and TRPML. Other less-well categorized TRP channels exist, including yeast channels and a number of Group 1 and Group 2 channels present in non-animals. Many of these channels mediate a variety of sensations such as pain, temperature, different kinds of tastes, pressure, and vision. In the body, some TRP channels are thought to behave like microscopic thermometers and used in animals to sense hot or cold. Some TRP channels are activated by molecules found in spices like garlic (allicin), chili pepper (capsaicin), wasabi ; others are activated by menthol, camphor, peppermint, and cooling agents; yet others are activated by molecules found in cannabis or stevia. Some act as sensors of osmotic pressure, volume, stretch, and vibration. Most of the channels are activated or inhibited by signaling lipids and contribute to a family of lipid-gated ion channels.
Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs.
Naringin is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness created by naringin. In humans naringin is metabolized to the aglycone naringenin by naringinase present in the gut.
Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone form is called hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.
Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges. Hesperetin are not found to a significant extent in Citrus spp.
TRPM is a family of transient receptor potential ion channels (M standing for wikt:melastatin). Functional TRPM channels are believed to form tetramers. The TRPM family consists of eight different channels, TRPM1–TRPM8.
Transient receptor potential cation channel subfamily M member 5 (TRPM5), also known as long transient receptor potential channel 5 is a protein that in humans is encoded by the TRPM5 gene.
Transient receptor potential cation channel subfamily M (melastatin) member 8 (TRPM8), also known as the cold and menthol receptor 1 (CMR1), is a protein that in humans is encoded by the TRPM8 gene. The TRPM8 channel is the primary molecular transducer of cold somatosensation in humans. In addition, mints can desensitize a region through the activation of TRPM8 receptors.
Transient receptor potential cation channel subfamily M member 3 is a protein that in humans is encoded by the TRPM3 gene.
Tricin is a chemical compound. It is an O-methylated flavone, a type of flavonoid. It can be found in rice bran and sugarcane.
The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups. O-methylation has an effect on the solubility of flavonoids.
Pregnenolone sulfate is an endogenous excitatory neurosteroid that is synthesized from pregnenolone. It is known to have cognitive and memory-enhancing, antidepressant, anxiogenic, and proconvulsant effects.
Chalconoids Greek: χαλκός khalkós, "copper", due to its color), also known as chalcones, are natural phenols related to chalcone. They form the central core for a variety of important biological compounds.
Narirutin is a flavanone-7-O-glycoside, consisting of the flavanone naringenin bonded with the disaccharide rutinose.
Melitidin is a flavanone glycoside. Melitidin was discovered in bergamot orange juice and exhibits statin-like properties so the juice seems to have hypolipidemic activity.
Brutieridin is a flavanone glycoside. Brutieridin was discovered in bergamot orange juice and exhibits statin-like properties as well as an anticholesterolaemic effect. As a result, the juice seems to have hypolipidemic (lipid-lowering) activity.
9-Phenanthrol is an aromatic alcohol derived from phenanthrene, a tricyclic compound. It is a TRPM4 channel inhibitor. It can prevent the pancreas from secreting insulin when stimulated by glucose.
CIM-0216 is a chemical compound which acts as a potent and selective activator of the TRPM3 calcium channel. It produces nociception and inflammation and is used to study the function of the TRPM3 receptor in these processes.
Ononetin is a natural product from the deoxybenzoin group, which is found in the Russian traditional medicine plant Ononis spinosa. It acts as an inhibitor of the transient receptor potential ion channel TRPM3 and has analgesic effects in animal studies, as well as being used for research into the role of TRPM3 in the immune system dysfunction associated with chronic fatigue syndrome.
TRPM4-IN-5 is a drug which acts as a moderately potent but highly selective blocker of the TRPM4 ion channel, with an IC50 of 1.5μM. It is protective against glutamate mediated neuronal excitotoxicity.