Oroxylin A

Oroxylin A
Skeletal formula
Ball-and-stick model of oroxylin A
Names
IUPAC name
5,7-Dihydroxy-6-methoxyflavone
Systematic IUPAC name
5,7-Dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one
Other names
Baicalein 6-methyl ether
Identifiers
CAS Number
  • 480-11-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:61668 ☒N
ChemSpider
  • 4478428 ☒N
ECHA InfoCard 100.189.623 Edit this at Wikidata
KEGG
  • C22603
PubChem CID
  • 5320315
UNII
  • 53K24Z586G checkY
CompTox Dashboard (EPA)
  • DTXSID70197375 Edit this at Wikidata
InChI
  • InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5- 3-2-4-6-9/h2-8,18-19H,1H3
    Key: LKOJGSWUMISDOF-UHFFFAOYSA-N
  • COC1=C(C=C2C(=C1O)C(=O)C=C(O2)C3=CC=CC=C3)O
Properties
Chemical formula
 C16H12O5
Molar mass 284.26 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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Infobox references
Chemical compound

Oroxylin A is an O-methylated flavone, a chemical compound that can be found in the medicinal plants Scutellaria baicalensis[1] and Scutellaria lateriflora,[2][3] and the Oroxylum indicum tree.[4] It has demonstrated activity as a dopamine reuptake inhibitor,[5] and is also a negative allosteric modulator of the benzodiazepine site of the GABAA receptor.[5][6][7] Oroxylin A has been found to improve memory consolidation in mice by elevating brain-derived neurotrophic factor (BDNF) levels in the hippocampus.[8]

See also

References

  1. ^ Isolation and purification of baicalein, wogonin and oroxylin A from the medicinal plant Scutellaria baicalensis by high-speed counter-current chromatography. Hua-Bin Li and Feng Chen, Journal of Chromatography A, 13 May 2005, Volume 1074, Issues 1–2, pages 107–110, doi:10.1016/j.chroma.2005.03.088
  2. ^ Li J, Ding Y, Li XC, Ferreira D, Khan S, Smillie T, Khan IA (2009). "Scuteflorins A and B, dihydropyranocoumarins from Scutellaria lateriflora". J. Nat. Prod. 72 (6): 983–7. doi:10.1021/np900068t. PMID 19555121.
  3. ^ Nishikawa K, et al. (1999). "Phenolics in tissue cultures of Scutellaria" (PDF). Natural Medicines. 53 (4): 209–13.
  4. ^ The constitution of oroxylin-A, a yellow colouring matter from the root-bark of Oroxylum indicum, vent R. C. Shah, C. R. Mehta and T. S. Wheeler
  5. ^ a b Yoon SY, dela Peña I, Kim SM, Woo TS, Shin CY, Son KH, Park H, Lee YS, Ryu JH, Jin M, Kim KM, Cheong JH (2013). "Oroxylin A improves attention deficit hyperactivity disorder-like behaviors in the spontaneously hypertensive rat and inhibits reuptake of dopamine in vitro". Archives of Pharmacal Research. 36 (1): 134–140. doi:10.1007/s12272-013-0009-6. ISSN 0253-6269. PMID 23371806. S2CID 23927252.
  6. ^ Liao JF, Wang HH, Chen MC, Chen CC, Chen CF (1998). "Benzodiazepine binding site-interactive flavones from Scutellaria baicalensis root". Planta Med. 64 (6): 571–2. doi:10.1055/s-2006-957517. PMID 9776664. S2CID 260251315.
  7. ^ Liu X, Hong SI, Park SJ, Dela Peña JB, Che H, Yoon SY, Kim DH, Kim JM, Cai M, Risbrough V, Geyer MA, Shin CY, Cheong JH, Park H, Lew JH, Ryu JH (2013). "The ameliorating effects of 5,7-dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one, an oroxylin A derivative, against memory impairment and sensorimotor gating deficit in mice". Arch. Pharm. Res. 36 (7): 854–63. doi:10.1007/s12272-013-0106-6. PMID 23543630. S2CID 2554248.
  8. ^ Kim DH, Lee Y, Lee HE, Park SJ, Jeon SJ, Jeon SJ, Cheong JH, Shin CY, Son KH, Ryu JH (2014). "Oroxylin A enhances memory consolidation through the brain-derived neurotrophic factor in mice". Brain Res. Bull. 108: 67–73. doi:10.1016/j.brainresbull.2014.09.001. PMID 25218897. S2CID 21456826.
  • v
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Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
  • Hypolaetin 8-glucoside
  • Hypolaetin 8-glucuronide
of luteolin
Acetylated
  • Artocarpetin A
  • Artoindonesianin P
    • Sulfated glycosidesPolymersDrugs
    • v
    • t
    • e
    DATTooltip Dopamine transporter
    (DRIsTooltip Dopamine reuptake inhibitors)
    NETTooltip Norepinephrine transporter
    (NRIsTooltip Norepinephrine reuptake inhibitors)
    SERTTooltip Serotonin transporter
    (SRIsTooltip Serotonin reuptake inhibitors)
    VMATsTooltip Vesicular monoamine transporters
    Others
    See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
    • v
    • t
    • e
    GABA receptor modulators
    Ionotropic
    GABAATooltip γ-Aminobutyric acid A receptor
    GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor
    Metabotropic
    GABABTooltip γ-Aminobutyric acid B receptor
    See also
    Receptor/signaling modulators
    GABAA receptor positive modulators
    GABA metabolism/transport modulators


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