Tropoflavin (original) (raw)
7,8-二羟基黄酮（英語：7,8-Dihydroxyflavone，缩写7,8-DHF，也称为 Tropoflavin）是一种天然黄酮，存在于長柄菊（学名：Tridax procumbens）等植物中。
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| dbo:abstract | 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) (Kd ≈ 320 nM), 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 (and, formerly, R7), is under development for the treatment of Alzheimer's disease. Tropoflavin has demonstrated therapeutic efficacy in animal models of a variety of central nervous system disorders, including depression, Alzheimer's disease, cognitive deficits in schizophrenia, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, traumatic brain injury, cerebral ischemia, fragile X syndrome, and Rett syndrome. Tropoflavin also shows efficacy in animal models of age-associated cognitive impairment and enhances memory consolidation and emotional learning in healthy rodents. In addition, tropoflavin possesses powerful antioxidant activity independent of its actions on the TrkB receptor, and protects against glutamate-induced excitotoxicity, 6-hydroxydopamine-induced dopaminergic neurotoxicity, and oxidative stress-induced genotoxicity. It was also found to block methamphetamine-induced dopaminergic neurotoxicity, an effect which, in contrast to the preceding, was found to be TrkB-dependent. In 2017, evidence was published suggesting that tropoflavin and various other reported small-molecule TrkB agonists might not actually be direct agonists of the TrkB and might be mediating their observed effects by other means. Tropoflavin has been found to act as a weak aromatase inhibitor in vitro (Ki = 10 μM), though there is evidence to suggest that this might not be the case in vivo. In addition, it has been found to inhibit aldehyde dehydrogenase and estrogen sulfotransferase in vitro (Ki = 35 μM and 1–3 μM, respectively), though similarly to the case of aromatase, these activities have not yet been confirmed in vivo. Unlike many other flavonoids, tropoflavin does not show any inhibitory activity on 17β-hydroxysteroid dehydrogenase. Tropoflavin has also been observed to possess in vitro antiestrogenic effects at very high concentrations (Ki = 50 μM). A variety of close structural analogues of tropoflavin have also been found to act as TrkB agonists in vitro, including diosmetin (5,7,3'-trihydroxy-4'-methoxyflavone), norwogonin (5,7,8-trihydroxyflavone), eutropoflavin (4'-dimethylamino-7,8-dihydroxyflavone), 7,8,3'-trihydroxyflavone, , , , and . The highly hydroxylated analogue gossypetin (3,5,7,8,3',4'-hexahydroxyflavone), conversely, appears to be an antagonist of TrkB in vitro. Tropoflavin was also found to decrease mouse sleep in dark phase and reduce hypothalamus level of orexin A but not orexin B in mice. (en) 7,8-二羟基黄酮（英語：7,8-Dihydroxyflavone，缩写7,8-DHF，也称为 Tropoflavin）是一种天然黄酮，存在于長柄菊（学名：Tridax procumbens）等植物中。 (zh) |
| dbo:casNumber | 38183-03-8 |
| dbo:chEBI | 140464 |
| dbo:fdaUniiCode | ADB6MA8ZV2 |
| dbo:pubchem | 1880 |
| dbo:thumbnail | wiki-commons:Special:FilePath/7,8-dihydroxyflavone.svg?width=300 |
| dbo:wikiPageID | 45178236 (xsd:integer) |
| dbo:wikiPageLength | 21544 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1119114572 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:6-hydroxydopamine dbr:Potency_(pharmacology) dbr:Schizophrenia dbr:Cerebral_ischemia dbr:Antiestrogen dbr:Antioxidant dbr:Huntington's_disease dbr:Depression_(mood) dbr:Dopaminergic dbr:List_of_investigational_antidepressants dbr:Tridax_procumbens dbc:Aromatase_inhibitors dbr:Genotoxicity dbr:Natural_product dbr:Oral_administration dbr:Cognitive_deficit dbr:Gossypetin dbr:Brain-derived_neurotrophic_factor dbr:Orexin-A dbr:Animal_model dbr:Aromatase_inhibitor dbr:Structural_analogue dbr:Receptor_antagonist dbr:Prodrug dbc:Phytoestrogens dbc:Steroid_sulfotransferase_inhibitors dbc:TrkB_agonists dbr:Traumatic_brain_injury dbr:Tropomyosin_receptor_kinase_B dbr:Agonist dbr:Amyotrophic_lateral_sclerosis dbc:Antidepressants dbc:Flavones dbc:Neuroprotective_agents dbc:Nootropics dbr:Alzheimer's_disease dbr:Flavone dbr:Norwogonin dbr:Parkinson's_disease dbr:Central_nervous_system dbr:Fragile_X_syndrome dbr:Godmania_aesculifolia dbr:Memory_consolidation dbr:Receptor_(biochemistry) dbr:Rett_syndrome dbc:Antioxidants dbr:Aldehyde_dehydrogenase dbr:Binding_selectivity dbr:Bioavailability dbr:Blood–brain_barrier dbr:Diosmetin dbr:Emotional_learning dbr:Methamphetamine dbr:R13_(drug) dbr:R7_(drug) dbr:Neurotrophin dbr:Pharmacokinetics dbr:Excitotoxicity dbr:Flavonoid dbr:Neurotoxicity dbr:Oxidative_stress dbr:7,8,3'-trihydroxyflavone dbr:Cognitive_impairment dbr:Glutamate dbr:17β-hydroxysteroid_dehydrogenase dbr:4'-dimethylamino-7,8-dihydroxyflavone dbr:Small-molecule dbr:Estrogen_sulfotransferase dbr:3,7,8,2'-tetrahydroxyflavone dbr:3,7-dihydroxyflavone dbr:7,3'-dihydroxyflavone dbr:7,8,2'-trihydroxyflavone |
| dbp:bioavailability | ~5% (en) |
| dbp:c | 15 (xsd:integer) |
| dbp:casNumber | 38183 (xsd:integer) |
| dbp:chebi | 140464 (xsd:integer) |
| dbp:chemspiderid | 1809 (xsd:integer) |
| dbp:drugName | Tropoflavin (en) |
| dbp:eliminationHalfLife | 1800.0 |
| dbp:h | 10 (xsd:integer) |
| dbp:iupacName | 78 (xsd:integer) |
| dbp:o | 4 (xsd:integer) |
| dbp:pubchem | 1880 (xsd:integer) |
| dbp:smiles | c1cccc2ccc3cccO (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | COCYGNDCWFKTMF-UHFFFAOYSA-N (en) |
| dbp:synonyms | 78 (xsd:integer) |
| dbp:unii | ADB6MA8ZV2 (en) |
| dbp:width | 225 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Flavones dbt:Phytoestrogens dbt:Antioxidants dbt:Drugbox dbt:Estrogen_receptor_modulators dbt:Reflist dbt:Short_description dbt:Fdacite dbt:Growth_factor_receptor_modulators |
| dcterms:subject | dbc:Aromatase_inhibitors dbc:Phytoestrogens dbc:Steroid_sulfotransferase_inhibitors dbc:TrkB_agonists dbc:Antidepressants dbc:Flavones dbc:Neuroprotective_agents dbc:Nootropics dbc:Antioxidants |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:Drug |
| rdfs:comment | 7,8-二羟基黄酮（英語：7,8-Dihydroxyflavone，缩写7,8-DHF，也称为 Tropoflavin）是一种天然黄酮，存在于長柄菊（学名：Tridax procumbens）等植物中。 (zh) 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) (Kd ≈ 320 nM), 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 (and, formerly, R7), is under development for the treatment of Alzheimer's disease. (en) |
| rdfs:label | Tropoflavin (en) 7,8-二羟基黄酮 (zh) |
| owl:sameAs | wikidata:Tropoflavin dbpedia-zh:Tropoflavin https://global.dbpedia.org/id/sEVX |
| prov:wasDerivedFrom | wikipedia-en:Tropoflavin?oldid=1119114572&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/7,8-dihydroxyflavone.svg |
| foaf:isPrimaryTopicOf | wikipedia-en:Tropoflavin |
| foaf:name | Tropoflavin (en) |
| is dbo:wikiPageRedirects of | dbr:7,8-Dihydroxyflavone dbr:7,8-DHF dbr:7,8-dihydroxyflavone |
| is dbo:wikiPageWikiLink of | dbr:List_of_investigational_antidepressants dbr:Tropomyosin_receptor_kinase_B dbr:7,8-Dihydroxyflavone dbr:R13_(drug) dbr:R7_(drug) dbr:7,8-DHF dbr:7,8-dihydroxyflavone |
| is dbp:metabolites of | dbr:R13_(drug) dbr:R7_(drug) |
| is foaf:primaryTopic of | wikipedia-en:Tropoflavin |
