Isosakuranetin

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Isosakuranetin
Isosakuranetin.svg
Names
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1 X mark.svgN
    Key: HMUJXQRRKBLVOO-AWEZNQCLSA-N X mark.svgN
  • InChI=1/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
    Key: HMUJXQRRKBLVOO-AWEZNQCLBJ
  • COC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O
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).
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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]

Glycosides

Related Research Articles

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.

<span class="mw-page-title-main">Naringenin</span> Chemical compound

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.

<span class="mw-page-title-main">Naringin</span> Chemical compound

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.

<span class="mw-page-title-main">Hesperidin</span> Chemical compound

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.

<span class="mw-page-title-main">Hesperetin</span> Chemical compound

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.

<span class="mw-page-title-main">TRPM5</span> Protein-coding gene in the species Homo sapiens

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.

<span class="mw-page-title-main">TRPM8</span> Protein-coding gene in the species Homo sapiens

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.

<span class="mw-page-title-main">TRPM3</span> Protein-coding gene in the species Homo sapiens

Transient receptor potential cation channel subfamily M member 3 is a protein that in humans is encoded by the TRPM3 gene.

<span class="mw-page-title-main">Tricin</span> Chemical compound

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.

<span class="mw-page-title-main">Pregnenolone sulfate</span> Chemical compound

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.

<span class="mw-page-title-main">Chalconoid</span>

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.

<span class="mw-page-title-main">Narirutin</span> Chemical compound

Narirutin is a flavanone-7-O-glycoside, consisting of the flavanone naringenin bonded with the disaccharide rutinose.

<span class="mw-page-title-main">Melitidin</span> Chemical compound

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.

<span class="mw-page-title-main">Brutieridin</span> Chemical compound

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.

<span class="mw-page-title-main">9-Phenanthrol</span> Chemical compound

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.

<span class="mw-page-title-main">CIM-0216</span> Chemical compound

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.

<span class="mw-page-title-main">Ononetin</span> Chemical compound

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.

<span class="mw-page-title-main">TRPM4-IN-5</span> Chemical compound

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.

References

  1. "Polyphenols in Human Health and Disease" ISBN   9780123984562
  2. Straub, Isabelle; Krügel, Ute; Mohr, Florian; Teichert, Jens; Rizun, Oleksandr; Konrad, Maik; Oberwinkler, Johannes; Schaefer, Michael (November 2013). "Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo". Molecular Pharmacology. 84 (5): 736–750. doi:10.1124/mol.113.086843. ISSN   1521-0111. PMID   24006495.