Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H12O5 |
Molecular Weight | 284.2635 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(O)C=C2OC(=CC(=O)C2=C1O)C3=CC=CC=C3
InChI
InChIKey=LKOJGSWUMISDOF-UHFFFAOYSA-N
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
Molecular Formula | C16H12O5 |
Molecular Weight | 284.2635 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Oroxylin A is a flavonoid compound, one of the main components extracted from Scutellariae radix. It possess a broad spectrum of pharmacological effects, especially anti-cancer, anti-inflammatory and neuroprotective activity. Oroxylin A inactivated HIF1α and reprogrammed fatty acid metabolism of HCT116 cells, decreasing intracellular fatty acid level and enhancing fatty acid oxidation. Oroxylin A improves attention-deficit hyperactivity disorder-like behaviors in spontaneously hypertensive rats via enhancement of dopamine neurotransmission and not modulation of GABA pathway as previously reported. Importantly, the present study indicates the potential therapeutic value of oroxylin A in the treatment of attention-deficit hyperactivity disorder. Both in vitro and in vivo study showed that oroxylin A possesses low toxicity, but the field was just limited in cancer research.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: WP2380 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25218897 |
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Target ID: GO:0090494 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23371806 |
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Target ID: map01212 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28594405 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana. | 1992 Apr |
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Antiviral Chinese medicinal herbs against respiratory syncytial virus. | 2002 Feb |
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5,7-Dihydroxy-6-methoxyflavone, a benzodiazepine site ligand isolated from Scutellaria baicalensis Georgi, with selective antagonistic properties. | 2003 Jul 1 |
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Isolation and purification of baicalein, wogonin and oroxylin A from the medicinal plant Scutellaria baicalensis by high-speed counter-current chromatography. | 2005 May 13 |
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Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents. | 2005 Sep 1 |
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Oroxylin A induced apoptosis of human hepatocellular carcinoma cell line HepG2 was involved in its antitumor activity. | 2006 Dec 15 |
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Liquid chromatography with tandem mass spectrometry for the simultaneous determination of baicalein, baicalin, oroxylin A and wogonin in rat plasma. | 2006 Dec 5 |
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Effect of the flavonoid, oroxylin A, on transient cerebral hypoperfusion-induced memory impairment in mice. | 2006 Nov |
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Antioxidative and anti-inflammatory activities of polyhydroxyflavonoids of Scutellaria baicalensis GEORGI. | 2006 Oct |
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Pharmacokinetics of baicalein, baicalin and wogonin after oral administration of a standardized extract of Scutellaria baicalensis, PF-2405 in rats. | 2007 Feb |
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New dihydrochalcones and anti-platelet aggregation constituents from the leaves of Muntingia calabura. | 2007 Jun |
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The ameliorating effect of oroxylin A on scopolamine-induced memory impairment in mice. | 2007 May |
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Synthesis and biological evaluation of novel 8-aminomethylated oroxylin A analogues as alpha-glucosidase inhibitors. | 2008 Mar 1 |
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The effects of acute and repeated oroxylin A treatments on Abeta(25-35)-induced memory impairment in mice. | 2008 Oct |
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Oroxylin A suppresses invasion through down-regulating the expression of matrix metalloproteinase-2/9 in MDA-MB-435 human breast cancer cells. | 2009 Jan 28 |
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Scuteflorins A and B, dihydropyranocoumarins from Scutellaria lateriflora. | 2009 Jun |
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In vitro study of the tocolytic effect of oroxylin A from Scutellaria baicalensis root. | 2009 Mar 4 |
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MAC-related mitochondrial pathway in oroxylin-A-induced apoptosis in human hepatocellular carcinoma HepG2 cells. | 2009 Nov 1 |
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[Flavonoids from Scutellaria baicalensis and their bioactivities]. | 2009 Oct 18 |
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Evaluation of the flavonoid oroxylin A as an inhibitor of P-glycoprotein-mediated cellular efflux. | 2009 Sep |
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Use of isoform-specific UGT metabolism to determine and describe rates and profiles of glucuronidation of wogonin and oroxylin A by human liver and intestinal microsomes. | 2010 Aug |
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Synergistic effect of 5-fluorouracil and the flavanoid oroxylin A on HepG2 human hepatocellular carcinoma and on H22 transplanted mice. | 2010 Feb |
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Anti-pruritic effect of baicalin and its metabolites, baicalein and oroxylin A, in mice. | 2010 Jun |
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Synthesis and biological evaluation of novel benzyl-substituted flavones as free radical (DPPH) scavengers and α-glucosidase inhibitors. | 2010 Nov |
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Oroxylin A, a flavonoid, stimulates adult neurogenesis in the hippocampal dentate gyrus region of mice. | 2010 Nov |
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Flavonoids with prolyl oligopeptidase inhibitory activity isolated from Scutellaria racemosa Pers. | 2010 Sep |
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STAT1 mediates oroxylin a inhibition of iNOS and pro-inflammatory cytokines expression in microglial BV-2 cells. | 2012 |
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4'-bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages. | 2012 Jan 1 |
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Oroxylin A inhibits matrix metalloproteinase-2/9 expression and activation by up-regulating tissue inhibitor of metalloproteinase-2 and suppressing the ERK1/2 signaling pathway. | 2012 Mar 25 |
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Oroxylin A reverses P-glycoprotein-mediated multidrug resistance of MCF7/ADR cells by G2/M arrest. | 2013 May 23 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23371806
Rat: 1, 5 and 10 mg/kg
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27539056
Oroxylin A was able to inhibit glucose uptake and the release of lactate of human hepatocellular carcinoma HepG2 cells at relatively mild concentrations (12.5–50 uM) without inducing severe apoptosis (mostly 8.78%).
Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 03:21:11 GMT 2023
by
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Sat Dec 16 03:21:11 GMT 2023
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Record UNII |
53K24Z586G
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Record Status |
Validated (UNII)
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Record Version |
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