Oroxylin A

Oroxylin A

Names
IUPAC name 5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one
Other names Baicalein 6-methyl ether
Identifiers
CAS Number	480-11-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:61668
ChemSpider	4478428
ECHA InfoCard	100.189.623
PubChem	5320315
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
SMILES 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

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

See also

• Baicalin
• Baicalein
• Chaenomeles speciosa

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. 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
3. Yoon, Seo Young; dela Peña, Ike; Kim, Sung Mok; Woo, Tae Sun; Shin, Chan Young; Son, Kun Ho; Park, Haeil; Lee, Yong Soo; Ryu, Jong Hoon; Jin, Mingli; Kim, Kyeong-Man; Cheong, Jae Hoon (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.
4. 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.
5. 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.
6. 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.