Ononetin

Last updated
Ononetin
Ononetin structure.png
Identifiers
  • 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H14O4
Molar mass 258.273 g·mol−1
3D model (JSmol)
  • COC1=CC=C(C=C1)CC(=O)C2=C(C=C(C=C2)O)O
  • InChI=1S/C15H14O4/c1-19-12-5-2-10(3-6-12)8-14(17)13-7-4-11(16)9-15(13)18/h2-7,9,16,18H,8H2,1H3
  • Key:XHBZOAYMBBUURD-UHFFFAOYSA-N

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, [1] [2] as well as being used for research into the role of TRPM3 in the immune system dysfunction associated with chronic fatigue syndrome. [3] [4]

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">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.

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

The inorganic dye ammoniated ruthenium oxychloride, also known as ruthenium red, is used in histology to stain aldehyde fixed mucopolysaccharides.

<span class="mw-page-title-main">TRPV</span> Subgroup of TRP cation channels named after the vanilloid receptor

TRPV is a family of transient receptor potential cation channels in animals. All TRPVs are highly calcium selective.

TRPM is a family of transient receptor potential ion channels. Functional TRPM channels are believed to form tetramers. The TRPM family consists of eight different channels, TRPM1–TRPM8.

<span class="mw-page-title-main">TRPM1</span> Protein-coding gene in the species Homo sapiens

Transient receptor potential cation channel subfamily M member 1 is a protein that in humans is encoded by the TRPM1 gene.

<span class="mw-page-title-main">TRPM2</span> Protein-coding gene in the species Homo sapiens

Transient receptor potential cation channel, subfamily M, member 2, also known as TRPM2, is a protein that in humans is encoded by the TRPM2 gene.

<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">TRPM4</span> Protein-coding gene in the species Homo sapiens

Transient receptor potential cation channel subfamily M member 4 (hTRPM4), also known as melastatin-4, is a protein that in humans is encoded by the TRPM4 gene.

<span class="mw-page-title-main">TRPV4</span> Protein-coding gene in the species Homo sapiens

Transient receptor potential cation channel subfamily V member 4 is an ion channel protein that in humans is encoded by the TRPV4 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">TRPV3</span>

Transient receptor potential cation channel, subfamily V, member 3, also known as TRPV3, is a human gene encoding the protein of the same name.

<span class="mw-page-title-main">TRPM7</span>

Transient receptor potential cation channel, subfamily M, member 7, also known as TRPM7, is a human gene encoding a protein of the same name.

Treatment of chronic fatigue syndrome (CFS) is variable and uncertain, and the condition is primarily managed rather than cured.

<span class="mw-page-title-main">Clinical descriptions of chronic fatigue syndrome</span> Review of the topic

Clinical descriptions of chronic fatigue syndrome (CFS) vary. Different groups have produced sets of diagnostic criteria that share many similarities. The biggest differences between criteria are whether post-exertional malaise (PEM) is required, and the number of symptoms needed. Aspects of the condition are controversial, with disagreements over etiology, pathophysiology, treatment and naming between medical practitioners, researchers, patients and advocacy groups. Furthermore, diagnosing CFS can be difficult due to several factors, including lack of a standard test and non-specific symptoms. Subgroup analysis suggests that, depending on the applied definition, CFS may represent a variety of conditions rather than a single disease entity.

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

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. Isosakuranetin is a potent inhibitor of TRPM3 channels.

<span class="mw-page-title-main">Chronic fatigue syndrome</span> Medical condition involving extreme fatigue among other symptoms

Chronic fatigue syndrome (CFS), also called myalgic encephalomyelitis (ME) or ME/CFS, is a complex, debilitating, long-term medical condition. The causes and mechanisms of the disease are not fully understood. Distinguishing core symptoms are lengthy exacerbations or flare-ups of the illness following ordinary minor physical or mental activity, known as post-exertional malaise (PEM); greatly diminished capacity to accomplish tasks that were routine before the illness; and sleep disturbances. Orthostatic intolerance and cognitive dysfunction are also diagnostic. Frequently and variably, other common symptoms occur involving numerous body systems, and chronic pain is common. The unexplained and often incapacitating fatigue in CFS is different from that caused by normal strenuous ongoing exertion, is not significantly relieved by rest, and is not due to a previous medical condition. Diagnosis is based on the person's symptoms because no confirmed diagnostic test is available.

<span class="mw-page-title-main">Post-exertional malaise</span> Symptom of chronic fatigue syndrome

Post-exertional malaise (PEM) is a worsening of chronic fatigue syndrome symptoms that occurs after exertion. PEM involves increased fatigue, and an exacerbation of other symptoms. PEM is often severe enough to be disabling, and is triggered by ordinary activities that healthy people tolerate. Post-exertional malaise typically begins 12–48 hours after the activity that triggers it, and lasts for days, but this is highly variable. Management of PEM is symptomatic, and patients are recommended to pace their activities to avoid triggering PEM.

<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.

References

  1. Straub I, Mohr F, Stab J, Konrad M, Philipp SE, Oberwinkler J, Schaefer M (April 2013). "Citrus fruit and fabacea secondary metabolites potently and selectively block TRPM3". British Journal of Pharmacology. 168 (8): 1835–50. doi:10.1111/bph.12076. PMC   3623054 . PMID   23190005.
  2. Straub I, Krügel U, Mohr F, Teichert J, Rizun O, Konrad M, et al. (November 2013). "Flavanones that selectively inhibit TRPM3 attenuate thermal nociception in vivo". Molecular Pharmacology. 84 (5): 736–50. doi:10.1124/mol.113.086843. PMID   24006495. S2CID   20522738.
  3. Cabanas H, Muraki K, Balinas C, Eaton-Fitch N, Staines D, Marshall-Gradisnik S (April 2019). "Validation of impaired Transient Receptor Potential Melastatin 3 ion channel activity in natural killer cells from Chronic Fatigue Syndrome/ Myalgic Encephalomyelitis patients". Molecular Medicine. 25 (1): 14. doi:10.1186/s10020-019-0083-4. PMC   6480905 . PMID   31014226.
  4. Cabanas H, Muraki K, Staines D, Marshall-Gradisnik S (2019). "Naltrexone Restores Impaired Transient Receptor Potential Melastatin 3 Ion Channel Function in Natural Killer Cells From Myalgic Encephalomyelitis/Chronic Fatigue Syndrome Patients". Frontiers in Immunology. 10: 2545. doi: 10.3389/fimmu.2019.02545 . PMC   6834647 . PMID   31736966.