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m 7,8-DHF exists in nature and is not a purely synthetic compound.
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7,8-DHF also shows efficacy in animal models of age-associated [[cognitive impairment]]<ref name="pmid22694088">{{vcite2 journal | vauthors = Zeng Y, Lv F, Li L, Yu H, Dong M, Fu Q | title = 7,8-dihydroxyflavone rescues spatial memory and synaptic plasticity in cognitively impaired aged rats | journal = J. Neurochem. | volume = 122 | issue = 4 | pages = 800–11 | year = 2012 | pmid = 22694088 | doi = 10.1111/j.1471-4159.2012.07830.x | url = http://dx.doi.org/10.1111/j.1471-4159.2012.07830.x}}</ref> and enhances [[memory consolidation]] and [[emotional learning]] in healthy rodents.<ref name="pmid24070857">{{vcite2 journal | vauthors = Bollen E, Vanmierlo T, Akkerman S, Wouters C, Steinbusch HM, Prickaerts J | title = 7,8-Dihydroxyflavone improves memory consolidation processes in rats and mice | journal = Behav. Brain Res. | volume = 257 | issue = | pages = 8–12 | year = 2013 | pmid = 24070857 | doi = 10.1016/j.bbr.2013.09.029 | url = http://linkinghub.elsevier.com/retrieve/pii/S0166-4328(13)00579-2}}</ref><ref name="pmid21123312">{{vcite2 journal | vauthors = Andero R, Heldt SA, Ye K, Liu X, Armario A, Ressler KJ | title = Effect of 7,8-dihydroxyflavone, a small-molecule TrkB agonist, on emotional learning | journal = Am J Psychiatry | volume = 168 | issue = 2 | pages = 163–72 | year = 2011 | pmid = 21123312 | pmc = 3770732 | doi = 10.1176/appi.ajp.2010.10030326 | url = http://psychiatryonline.org/doi/abs/10.1176/appi.ajp.2010.10030326?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%3dpubmed}}</ref> In addition, 7,8-DHF possesses powerful [[antioxidant]] activity independent of its actions on the TrkB receptor,<ref name="FotiPiattelli1996">{{cite journal|last1=Foti|first1=Mario|last2=Piattelli|first2=Mario|last3=Baratta|first3=Maria Tiziana|last4=Ruberto|first4=Giuseppe|title=Flavonoids, Coumarins, and Cinnamic Acids as Antioxidants in a Micellar System. Structure−Activity Relationship†|journal=Journal of Agricultural and Food Chemistry|volume=44|issue=2|year=1996|pages=497–501|issn=0021-8561|doi=10.1021/jf950378u}}</ref> and protects against [[glutamate]]-induced [[excitotoxicity]],<ref name="pmid21651962">{{vcite2 journal | vauthors = Chen J, Chua KW, Chua CC, Yu H, Pei A, Chua BH, Hamdy RC, Xu X, Liu CF | title = Antioxidant activity of 7,8-dihydroxyflavone provides neuroprotection against glutamate-induced toxicity | journal = Neurosci. Lett. | volume = 499 | issue = 3 | pages = 181–5 | year = 2011 | pmid = 21651962 | doi = 10.1016/j.neulet.2011.05.054 | url = http://linkinghub.elsevier.com/retrieve/pii/S0304-3940(11)00680-X}}</ref> [[6-hydroxydopamine]]-induced [[dopaminergic]] [[neurotoxicity]],<ref name="pmid24220540">{{vcite2 journal | vauthors = Han X, Zhu S, Wang B, Chen L, Li R, Yao W, Qu Z | title = Antioxidant action of 7,8-dihydroxyflavone protects PC12 cells against 6-hydroxydopamine-induced cytotoxicity | journal = Neurochem. Int. | volume = 64 | issue = | pages = 18–23 | year = 2014 | pmid = 24220540 | doi = 10.1016/j.neuint.2013.10.018 | url = http://linkinghub.elsevier.com/retrieve/pii/S0197-0186(13)00291-X}}</ref> and [[oxidative stress]]-induced [[genotoxicity]].<ref name="pmid19182370">{{vcite2 journal | vauthors = Zhang R, Kang KA, Piao MJ, Ko DO, Wang ZH, Chang WY, You HJ, Lee IK, Kim BJ, Kang SS, Hyun JW | title = Preventive effect of 7,8-dihydroxyflavone against oxidative stress induced genotoxicity | journal = Biol. Pharm. Bull. | volume = 32 | issue = 2 | pages = 166–71 | year = 2009 | pmid = 19182370 | doi = | url = http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/32.166?from=PubMed}}</ref> It was also found to block [[methamphetamine]]-induced [[dopaminergic]] [[neurotoxicity]], an effect which, in contrast to the preceding, ''was'' found to be TrkB-dependent.<ref name="pmid23934209">{{vcite2 journal | vauthors = Ren Q, Zhang JC, Ma M, Fujita Y, Wu J, Hashimoto K | title = 7,8-Dihydroxyflavone, a TrkB agonist, attenuates behavioral abnormalities and neurotoxicity in mice after administration of methamphetamine | journal = Psychopharmacology (Berl.) | volume = 231 | issue = 1 | pages = 159–66 | year = 2014 | pmid = 23934209 | doi = 10.1007/s00213-013-3221-7 | url = http://dx.doi.org/10.1007/s00213-013-3221-7}}</ref>
7,8-DHF also shows efficacy in animal models of age-associated [[cognitive impairment]]<ref name="pmid22694088">{{vcite2 journal | vauthors = Zeng Y, Lv F, Li L, Yu H, Dong M, Fu Q | title = 7,8-dihydroxyflavone rescues spatial memory and synaptic plasticity in cognitively impaired aged rats | journal = J. Neurochem. | volume = 122 | issue = 4 | pages = 800–11 | year = 2012 | pmid = 22694088 | doi = 10.1111/j.1471-4159.2012.07830.x | url = http://dx.doi.org/10.1111/j.1471-4159.2012.07830.x}}</ref> and enhances [[memory consolidation]] and [[emotional learning]] in healthy rodents.<ref name="pmid24070857">{{vcite2 journal | vauthors = Bollen E, Vanmierlo T, Akkerman S, Wouters C, Steinbusch HM, Prickaerts J | title = 7,8-Dihydroxyflavone improves memory consolidation processes in rats and mice | journal = Behav. Brain Res. | volume = 257 | issue = | pages = 8–12 | year = 2013 | pmid = 24070857 | doi = 10.1016/j.bbr.2013.09.029 | url = http://linkinghub.elsevier.com/retrieve/pii/S0166-4328(13)00579-2}}</ref><ref name="pmid21123312">{{vcite2 journal | vauthors = Andero R, Heldt SA, Ye K, Liu X, Armario A, Ressler KJ | title = Effect of 7,8-dihydroxyflavone, a small-molecule TrkB agonist, on emotional learning | journal = Am J Psychiatry | volume = 168 | issue = 2 | pages = 163–72 | year = 2011 | pmid = 21123312 | pmc = 3770732 | doi = 10.1176/appi.ajp.2010.10030326 | url = http://psychiatryonline.org/doi/abs/10.1176/appi.ajp.2010.10030326?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%3dpubmed}}</ref> In addition, 7,8-DHF possesses powerful [[antioxidant]] activity independent of its actions on the TrkB receptor,<ref name="FotiPiattelli1996">{{cite journal|last1=Foti|first1=Mario|last2=Piattelli|first2=Mario|last3=Baratta|first3=Maria Tiziana|last4=Ruberto|first4=Giuseppe|title=Flavonoids, Coumarins, and Cinnamic Acids as Antioxidants in a Micellar System. Structure−Activity Relationship†|journal=Journal of Agricultural and Food Chemistry|volume=44|issue=2|year=1996|pages=497–501|issn=0021-8561|doi=10.1021/jf950378u}}</ref> and protects against [[glutamate]]-induced [[excitotoxicity]],<ref name="pmid21651962">{{vcite2 journal | vauthors = Chen J, Chua KW, Chua CC, Yu H, Pei A, Chua BH, Hamdy RC, Xu X, Liu CF | title = Antioxidant activity of 7,8-dihydroxyflavone provides neuroprotection against glutamate-induced toxicity | journal = Neurosci. Lett. | volume = 499 | issue = 3 | pages = 181–5 | year = 2011 | pmid = 21651962 | doi = 10.1016/j.neulet.2011.05.054 | url = http://linkinghub.elsevier.com/retrieve/pii/S0304-3940(11)00680-X}}</ref> [[6-hydroxydopamine]]-induced [[dopaminergic]] [[neurotoxicity]],<ref name="pmid24220540">{{vcite2 journal | vauthors = Han X, Zhu S, Wang B, Chen L, Li R, Yao W, Qu Z | title = Antioxidant action of 7,8-dihydroxyflavone protects PC12 cells against 6-hydroxydopamine-induced cytotoxicity | journal = Neurochem. Int. | volume = 64 | issue = | pages = 18–23 | year = 2014 | pmid = 24220540 | doi = 10.1016/j.neuint.2013.10.018 | url = http://linkinghub.elsevier.com/retrieve/pii/S0197-0186(13)00291-X}}</ref> and [[oxidative stress]]-induced [[genotoxicity]].<ref name="pmid19182370">{{vcite2 journal | vauthors = Zhang R, Kang KA, Piao MJ, Ko DO, Wang ZH, Chang WY, You HJ, Lee IK, Kim BJ, Kang SS, Hyun JW | title = Preventive effect of 7,8-dihydroxyflavone against oxidative stress induced genotoxicity | journal = Biol. Pharm. Bull. | volume = 32 | issue = 2 | pages = 166–71 | year = 2009 | pmid = 19182370 | doi = | url = http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/32.166?from=PubMed}}</ref> It was also found to block [[methamphetamine]]-induced [[dopaminergic]] [[neurotoxicity]], an effect which, in contrast to the preceding, ''was'' found to be TrkB-dependent.<ref name="pmid23934209">{{vcite2 journal | vauthors = Ren Q, Zhang JC, Ma M, Fujita Y, Wu J, Hashimoto K | title = 7,8-Dihydroxyflavone, a TrkB agonist, attenuates behavioral abnormalities and neurotoxicity in mice after administration of methamphetamine | journal = Psychopharmacology (Berl.) | volume = 231 | issue = 1 | pages = 159–66 | year = 2014 | pmid = 23934209 | doi = 10.1007/s00213-013-3221-7 | url = http://dx.doi.org/10.1007/s00213-013-3221-7}}</ref>


7,8-DHF has been found to act as a weak [[aromatase inhibitor]] ''in vitro'' (K<sub>i</sub> = 10 μM),<ref name="pmid9435150">{{vcite2 journal | vauthors = Kao YC, Zhou C, Sherman M, Laughton CA, Chen S | title = Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study | journal = Environ. Health Perspect. | volume = 106 | issue = 2 | pages = 85–92 | year = 1998 | pmid = 9435150 | pmc = 1533021 | doi = | url = }}</ref> though there is evidence to suggest that this might not be the case ''in vivo''.<ref name="pmid20133810" /> In addition, it has been found to inhibit [[aldehyde dehydrogenase]] and [[estrogen sulfotransferase]] ''in vitro'' (K<sub>i</sub> = 35 μM and 1–3 μM, respectively), though similarly to the case of aromatase, these activities have not been confirmed ''in vivo''.<ref name="pmid20133810" /> Unlike many other [[flavonoid]]s, 7,8-DHF does not show any inhibitory activity on [[17β-hydroxysteroid dehydrogenase]].<ref name="Le BailLaroche1998">{{cite journal|last1=Le Bail|first1=J.C|last2=Laroche|first2=T|last3=Marre-Fournier|first3=F|last4=Habrioux|first4=G|title=Aromatase and 17β-hydroxysteroid dehydrogenase inhibition by flavonoids|journal=Cancer Letters|volume=133|issue=1|year=1998|pages=101–106|issn=03043835|doi=10.1016/S0304-3835(98)00211-0}}</ref> 7,8-DHF has also been observed to possess ''in vitro'' [[antiestrogen]]ic effects at very high concentrations (K<sub>i</sub> = 50 μM).<ref name="pmid9751276">{{vcite2 journal | vauthors = Le Bail JC, Varnat F, Nicolas JC, Habrioux G | title = Estrogenic and antiproliferative activities on MCF-7 human bre<ref></ref>ast cancer cells by flavonoids | journal = Cancer Lett. | volume = 130 | issue = 1-2 | pages = 209–16 | year = 1998 | pmid = 9751276 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/S0304-3835(98)00141-4}}</ref><ref name="pmid11720850">{{vcite2 journal | vauthors = Pouget C, Lauthier F, Simon A, Fagnere C, Basly JP, Delage C, Chulia AJ | title = Flavonoids: structural requirements for antiproliferative activity on breast cancer cells | journal = Bioorg. Med. Chem. Lett. | volume = 11 | issue = 24 | pages = 3095–7 | year = 2001 | pmid = 11720850 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/S0960894X01006175}}</ref>
7,8-DHF has been found to act as a weak [[aromatase inhibitor]] ''in vitro'' (K<sub>i</sub> = 10 μM),<ref name="pmid9435150">{{vcite2 journal | vauthors = Kao YC, Zhou C, Sherman M, Laughton CA, Chen S | title = Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study | journal = Environ. Health Perspect. | volume = 106 | issue = 2 | pages = 85–92 | year = 1998 | pmid = 9435150 | pmc = 1533021 | doi = | url = }}</ref> though there is evidence to suggest that this might not be the case ''in vivo''.<ref name="pmid20133810" /> In addition, it has been found to inhibit [[aldehyde dehydrogenase]] and [[estrogen sulfotransferase]] ''in vitro'' (K<sub>i</sub> = 35 μM and 1–3 μM, respectively), though similarly to the case of aromatase, these activities have not been confirmed ''in vivo''.<ref name="pmid20133810" /> Unlike many other [[flavonoid]]s, 7,8-DHF does not show any inhibitory activity on [[17β-hydroxysteroid dehydrogenase]].<ref name="Le BailLaroche1998">{{cite journal|last1=Le Bail|first1=J.C|last2=Laroche|first2=T|last3=Marre-Fournier|first3=F|last4=Habrioux|first4=G|title=Aromatase and 17β-hydroxysteroid dehydrogenase inhibition by flavonoids|journal=Cancer Letters|volume=133|issue=1|year=1998|pages=101–106|issn=03043835|doi=10.1016/S0304-3835(98)00211-0}}</ref> 7,8-DHF has also been observed to possess ''in vitro'' [[antiestrogen]]ic effects at very high concentrations (K<sub>i</sub> = 50 μM).<ref name="pmid9751276">{{vcite2 journal | vauthors = Le Bail JC, Varnat F, Nicolas JC, Habrioux G | title = Estrogenic and antiproliferative activities on MCF-7 human breast cancer cells by flavonoids | journal = Cancer Lett. | volume = 130 | issue = 1-2 | pages = 209–16 | year = 1998 | pmid = 9751276 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/S0304-3835(98)00141-4}}</ref><ref name="pmid11720850">{{vcite2 journal | vauthors = Pouget C, Lauthier F, Simon A, Fagnere C, Basly JP, Delage C, Chulia AJ | title = Flavonoids: structural requirements for antiproliferative activity on breast cancer cells | journal = Bioorg. Med. Chem. Lett. | volume = 11 | issue = 24 | pages = 3095–7 | year = 2001 | pmid = 11720850 | doi = | url = http://linkinghub.elsevier.com/retrieve/pii/S0960894X01006175}}</ref>


==See also==
==See also==

Revision as of 08:56, 16 March 2015

Tropoflavin
Clinical data
ATC code
  • None
Identifiers
  • 7,8-Dihydroxy-2-phenyl-4H-chromen-4-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.048.903 Edit this at Wikidata
Chemical and physical data
FormulaC15H10O4
Molar mass254.238 g/mol
3D model (JSmol)
  • c1ccc(cc1)c2cc(=O)c3ccc(c(c3o2)O)O
  • InChI=1S/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H
  • Key:COCYGNDCWFKTMF-UHFFFAOYSA-N

7,8-Dihydroxyflavone (7,8-DHF) is a natural flavone, found in Godmania aesculifolia and primula tree leaves, which has been found to act as a potent and selective small-molecule agonist of the TrkB receptor (Kd ≈ 320 nM), the main signaling receptor of brain-derived neurotrophic factor (BDNF),[1][2][3] and is both orally-bioavailable and able to penetrate the blood-brain-barrier,[4] though with a relatively short half-life (~9 min with 1 mg/kg oral administration in rats).[5]

7,8-DHF has demonstrated remarkable therapeutic efficacy in animal models of a variety of central nervous system disorders,[3] including depression,[4] Alzheimer's disease,[6][7][8] cognitive deficits in schizophrenia,[9] Parkinson's disease,[1] Huntington's disease,[10] amyotrophic lateral sclerosis,[11] traumatic brain injury,[12] cerebral ischemia,[13][14] fragile X syndrome,[15] and Rett syndrome.[16]

7,8-DHF also shows efficacy in animal models of age-associated cognitive impairment[17] and enhances memory consolidation and emotional learning in healthy rodents.[18][19] In addition, 7,8-DHF possesses powerful antioxidant activity independent of its actions on the TrkB receptor,[20] and protects against glutamate-induced excitotoxicity,[21] 6-hydroxydopamine-induced dopaminergic neurotoxicity,[22] and oxidative stress-induced genotoxicity.[23] It was also found to block methamphetamine-induced dopaminergic neurotoxicity, an effect which, in contrast to the preceding, was found to be TrkB-dependent.[24]

7,8-DHF has been found to act as a weak aromatase inhibitor in vitro (Ki = 10 μM),[25] though there is evidence to suggest that this might not be the case in vivo.[1] 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 been confirmed in vivo.[1] Unlike many other flavonoids, 7,8-DHF does not show any inhibitory activity on 17β-hydroxysteroid dehydrogenase.[26] 7,8-DHF has also been observed to possess in vitro antiestrogenic effects at very high concentrations (Ki = 50 μM).[27][28]

See also

References

  1. ^ a b c d Jang SW, Liu X, Yepes M, Shepherd KR, Miller GW, Liu Y, Wilson WD, Xiao G, Blanchi B, Sun YE, Ye K (2010). "A selective TrkB agonist with potent neurotrophic activities by 7,8-dihydroxyflavone". Proc. Natl. Acad. Sci. U.S.A. 107 (6): 2687–92. doi:10.1073/pnas.0913572107. PMC 2823863. PMID 20133810.
  2. ^ Liu X, Obianyo O, Chan CB, Huang J, Xue S, Yang JJ, Zeng F, Goodman M, Ye K (2014). "Biochemical and biophysical investigation of the brain-derived neurotrophic factor mimetic 7,8-dihydroxyflavone in the binding and activation of the TrkB receptor". J. Biol. Chem. 289 (40): 27571–84. doi:10.1074/jbc.M114.562561. PMID 25143381.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  3. ^ a b Zeng Y, Wang X, Wang Q, Liu S, Hu X, McClintock SM (2013). "Small molecules activating TrkB receptor for treating a variety of CNS disorders". CNS Neurol Disord Drug Targets. 12 (7): 1066–77. PMID 23844685.
  4. ^ a b Liu X, Chan CB, Jang SW, Pradoldej S, Huang J, He K, Phun LH, France S, Xiao G, Jia Y, Luo HR, Ye K (2010). "A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect". J. Med. Chem. 53 (23): 8274–86. doi:10.1021/jm101206p. PMC 3150605. PMID 21073191.
  5. ^ Liu X, Chan CB, Qi Q, Xiao G, Luo HR, He X, Ye K (2012). "Optimization of a small tropomyosin-related kinase B (TrkB) agonist 7,8-dihydroxyflavone active in mouse models of depression". J. Med. Chem. 55 (19): 8524–37. doi:10.1021/jm301099x. PMC 3491656. PMID 22984948.
  6. ^ Castello NA, Nguyen MH, Tran JD, Cheng D, Green KN, LaFerla FM (2014). "7,8-Dihydroxyflavone, a small molecule TrkB agonist, improves spatial memory and increases thin spine density in a mouse model of Alzheimer disease-like neuronal loss". PLoS ONE. 9 (3): e91453. doi:10.1371/journal.pone.0091453. PMC 3948846. PMID 24614170.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  7. ^ Chen C, Li XH, Zhang S, Tu Y, Wang YM, Sun HT (2014). "7,8-dihydroxyflavone ameliorates scopolamine-induced Alzheimer-like pathologic dysfunction". Rejuvenation Res. 17 (3): 249–54. doi:10.1089/rej.2013.1519. PMID 24325271.
  8. ^ Zhang Z, Liu X, Schroeder JP, Chan CB, Song M, Yu SP, Weinshenker D, Ye K (2014). "7,8-dihydroxyflavone prevents synaptic loss and memory deficits in a mouse model of Alzheimer's disease". Neuropsychopharmacology. 39 (3): 638–50. doi:10.1038/npp.2013.243. PMID 24022672.
  9. ^ Yang YJ, Li YK, Wang W, Wan JG, Yu B, Wang MZ, Hu B (2014). "Small-molecule TrkB agonist 7,8-dihydroxyflavone reverses cognitive and synaptic plasticity deficits in a rat model of schizophrenia". Pharmacol. Biochem. Behav. 122: 30–6. doi:10.1016/j.pbb.2014.03.013. PMID 24662915.
  10. ^ Jiang M, Peng Q, Liu X, Jin J, Hou Z, Zhang J, Mori S, Ross CA, Ye K, Duan W (2013). "Small-molecule TrkB receptor agonists improve motor function and extend survival in a mouse model of Huntington's disease". Hum. Mol. Genet. 22 (12): 2462–70. doi:10.1093/hmg/ddt098. PMC 3658168. PMID 23446639.
  11. ^ Korkmaz OT, Aytan N, Carreras I, Choi JK, Kowall NW, Jenkins BG, Dedeoglu A (2014). "7,8-Dihydroxyflavone improves motor performance and enhances lower motor neuronal survival in a mouse model of amyotrophic lateral sclerosis". Neurosci. Lett. 566: 286–91. doi:10.1016/j.neulet.2014.02.058. PMID 24637017.
  12. ^ Wu CH, Hung TH, Chen CC, Ke CH, Lee CY, Wang PY, Chen SF (2014). "Post-injury treatment with 7,8-dihydroxyflavone, a TrkB receptor agonist, protects against experimental traumatic brain injury via PI3K/Akt signaling". PLoS ONE. 9 (11): e113397. doi:10.1371/journal.pone.0113397. PMC 4240709. PMID 25415296.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  13. ^ Wang B, Wu N, Liang F, Zhang S, Ni W, Cao Y, Xia D, Xi H (2014). "7,8-dihydroxyflavone, a small-molecule tropomyosin-related kinase B (TrkB) agonist, attenuates cerebral ischemia and reperfusion injury in rats". J. Mol. Histol. 45 (2): 129–40. doi:10.1007/s10735-013-9539-y. PMID 24045895.
  14. ^ Uluc K, Kendigelen P, Fidan E, Zhang L, Chanana V, Kintner D, Akture E, Song C, Ye K, Sun D, Ferrazzano P, Cengiz P (2013). "TrkB receptor agonist 7, 8 dihydroxyflavone triggers profound gender- dependent neuroprotection in mice after perinatal hypoxia and ischemia". CNS Neurol Disord Drug Targets. 12 (3): 360–70. PMC 3674109. PMID 23469848.
  15. ^ Tian M, Zeng Y, Hu Y, Yuan X, Liu S, Li J, Lu P, Sun Y, Gao L, Fu D, Li Y, Wang S, McClintock SM (2015). "7, 8-Dihydroxyflavone induces synapse expression of AMPA GluA1 and ameliorates cognitive and spine abnormalities in a mouse model of fragile X syndrome". Neuropharmacology. 89: 43–53. doi:10.1016/j.neuropharm.2014.09.006. PMID 25229717.
  16. ^ Johnson RA, Lam M, Punzo AM, Li H, Lin BR, Ye K, Mitchell GS, Chang Q (2012). "7,8-dihydroxyflavone exhibits therapeutic efficacy in a mouse model of Rett syndrome". J. Appl. Physiol. 112 (5): 704–10. doi:10.1152/japplphysiol.01361.2011. PMC 3643819. PMID 22194327.
  17. ^ Zeng Y, Lv F, Li L, Yu H, Dong M, Fu Q (2012). "7,8-dihydroxyflavone rescues spatial memory and synaptic plasticity in cognitively impaired aged rats". J. Neurochem. 122 (4): 800–11. doi:10.1111/j.1471-4159.2012.07830.x. PMID 22694088.
  18. ^ Bollen E, Vanmierlo T, Akkerman S, Wouters C, Steinbusch HM, Prickaerts J (2013). "7,8-Dihydroxyflavone improves memory consolidation processes in rats and mice". Behav. Brain Res. 257: 8–12. doi:10.1016/j.bbr.2013.09.029. PMID 24070857.
  19. ^ Andero R, Heldt SA, Ye K, Liu X, Armario A, Ressler KJ (2011). "Effect of 7,8-dihydroxyflavone, a small-molecule TrkB agonist, on emotional learning". Am J Psychiatry. 168 (2): 163–72. doi:10.1176/appi.ajp.2010.10030326. PMC 3770732. PMID 21123312.
  20. ^ Foti, Mario; Piattelli, Mario; Baratta, Maria Tiziana; Ruberto, Giuseppe (1996). "Flavonoids, Coumarins, and Cinnamic Acids as Antioxidants in a Micellar System. Structure−Activity Relationship†". Journal of Agricultural and Food Chemistry. 44 (2): 497–501. doi:10.1021/jf950378u. ISSN 0021-8561.
  21. ^ Chen J, Chua KW, Chua CC, Yu H, Pei A, Chua BH, Hamdy RC, Xu X, Liu CF (2011). "Antioxidant activity of 7,8-dihydroxyflavone provides neuroprotection against glutamate-induced toxicity". Neurosci. Lett. 499 (3): 181–5. doi:10.1016/j.neulet.2011.05.054. PMID 21651962.
  22. ^ Han X, Zhu S, Wang B, Chen L, Li R, Yao W, Qu Z (2014). "Antioxidant action of 7,8-dihydroxyflavone protects PC12 cells against 6-hydroxydopamine-induced cytotoxicity". Neurochem. Int. 64: 18–23. doi:10.1016/j.neuint.2013.10.018. PMID 24220540.
  23. ^ Zhang R, Kang KA, Piao MJ, Ko DO, Wang ZH, Chang WY, You HJ, Lee IK, Kim BJ, Kang SS, Hyun JW (2009). "Preventive effect of 7,8-dihydroxyflavone against oxidative stress induced genotoxicity". Biol. Pharm. Bull. 32 (2): 166–71. PMID 19182370.
  24. ^ Ren Q, Zhang JC, Ma M, Fujita Y, Wu J, Hashimoto K (2014). "7,8-Dihydroxyflavone, a TrkB agonist, attenuates behavioral abnormalities and neurotoxicity in mice after administration of methamphetamine". Psychopharmacology (Berl.). 231 (1): 159–66. doi:10.1007/s00213-013-3221-7. PMID 23934209.
  25. ^ Kao YC, Zhou C, Sherman M, Laughton CA, Chen S (1998). "Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study". Environ. Health Perspect. 106 (2): 85–92. PMC 1533021. PMID 9435150.
  26. ^ Le Bail, J.C; Laroche, T; Marre-Fournier, F; Habrioux, G (1998). "Aromatase and 17β-hydroxysteroid dehydrogenase inhibition by flavonoids". Cancer Letters. 133 (1): 101–106. doi:10.1016/S0304-3835(98)00211-0. ISSN 0304-3835.
  27. ^ Le Bail JC, Varnat F, Nicolas JC, Habrioux G (1998). "Estrogenic and antiproliferative activities on MCF-7 human breast cancer cells by flavonoids". Cancer Lett. 130 (1–2): 209–16. PMID 9751276.
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