OROXYLIN A

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27539056 | https://www.ncbi.nlm.nih.gov/pubmed/28594405 | https://www.ncbi.nlm.nih.gov/pubmed/23371806

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
BDNF signaling pathway 1 Target ID: WP2380 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25218897	Activator 1430
dopamine uptake 14 Target ID: GO:0090494 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23371806	Inhibitor 8297
Fatty acid metabolism 1 Target ID: map01212 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28594405	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Attention deficit hyperactivity disorder 68 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23371806	Primary	Preclinical	Unknown Approved Use Unknown
Hepatoma 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28726775	Primary	Preclinical	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28594405	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana.	1992 Apr	1608273
Antiviral Chinese medicinal herbs against respiratory syncytial virus.	2002 Feb	11801383
5,7-Dihydroxy-6-methoxyflavone, a benzodiazepine site ligand isolated from Scutellaria baicalensis Georgi, with selective antagonistic properties.	2003 Jul 1	12818372
Isolation and purification of baicalein, wogonin and oroxylin A from the medicinal plant Scutellaria baicalensis by high-speed counter-current chromatography.	2005 May 13	15941045
Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents.	2005 Sep 1	16046127
Oroxylin A induced apoptosis of human hepatocellular carcinoma cell line HepG2 was involved in its antitumor activity.	2006 Dec 15	17069758
Liquid chromatography with tandem mass spectrometry for the simultaneous determination of baicalein, baicalin, oroxylin A and wogonin in rat plasma.	2006 Dec 5	16893689
Effect of the flavonoid, oroxylin A, on transient cerebral hypoperfusion-induced memory impairment in mice.	2006 Nov	17174385
Antioxidative and anti-inflammatory activities of polyhydroxyflavonoids of Scutellaria baicalensis GEORGI.	2006 Oct	17031041
Pharmacokinetics of baicalein, baicalin and wogonin after oral administration of a standardized extract of Scutellaria baicalensis, PF-2405 in rats.	2007 Feb	17366750
New dihydrochalcones and anti-platelet aggregation constituents from the leaves of Muntingia calabura.	2007 Jun	17516329
The ameliorating effect of oroxylin A on scopolamine-induced memory impairment in mice.	2007 May	17196405
Synthesis and biological evaluation of novel 8-aminomethylated oroxylin A analogues as alpha-glucosidase inhibitors.	2008 Mar 1	18255289
Oroxylin A induces G2/M phase cell-cycle arrest via inhibiting Cdk7-mediated expression of Cdc2/p34 in human gastric carcinoma BGC-823 cells.	2008 Nov	18957166
The effects of acute and repeated oroxylin A treatments on Abeta(25-35)-induced memory impairment in mice.	2008 Oct	18620712
[Studies on ethyl acetate soluble constituents of Huanglian Jiedutang].	2008 Sep	19160789
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	19100732
Scuteflorins A and B, dihydropyranocoumarins from Scutellaria lateriflora.	2009 Jun	19555121
In vitro study of the tocolytic effect of oroxylin A from Scutellaria baicalensis root.	2009 Mar 4	19272127
Apoptosis induction of oroxylin A in human cervical cancer HeLa cell line in vitro and in vivo.	2009 Mar 4	19135124
MAC-related mitochondrial pathway in oroxylin-A-induced apoptosis in human hepatocellular carcinoma HepG2 cells.	2009 Nov 1	19473757
[Flavonoids from Scutellaria baicalensis and their bioactivities].	2009 Oct 18	19829679
Evaluation of the flavonoid oroxylin A as an inhibitor of P-glycoprotein-mediated cellular efflux.	2009 Sep	19739602
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	20411407
Synergistic effect of 5-fluorouracil and the flavanoid oroxylin A on HepG2 human hepatocellular carcinoma and on H22 transplanted mice.	2010 Feb	19585117
Anti-pruritic effect of baicalin and its metabolites, baicalein and oroxylin A, in mice.	2010 Jun	20453872
Synthesis and biological evaluation of novel benzyl-substituted flavones as free radical (DPPH) scavengers and α-glucosidase inhibitors.	2010 Nov	21061220
Oroxylin A, a flavonoid, stimulates adult neurogenesis in the hippocampal dentate gyrus region of mice.	2010 Nov	20680459
Flavonoids with prolyl oligopeptidase inhibitory activity isolated from Scutellaria racemosa Pers.	2010 Sep	20117183
STAT1 mediates oroxylin a inhibition of iNOS and pro-inflammatory cytokines expression in microglial BV-2 cells.	2012	23236370
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	22101131
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	22245252
Oroxylin A reverses P-glycoprotein-mediated multidrug resistance of MCF7/ADR cells by G2/M arrest.	2013 May 23	23470866

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 1, 5 and 10 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

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%).

Name

Type

Language

OROXYLIN A

Common Name

English

BAICALEIN 6-METHYL ETHER

Brand Name

English

OROXYLIN

Common Name

English

5,7-DIHYDROXY-6-METHOXYFLAVONE

Systematic Name

English

5,7-DIHYDROXY-6-METHOXY-2-PHENYL-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

5,7-DIHYDROXY-6-METHOXY-2-PHENYLCHROMEN-4-ONE

Systematic Name

English

FLAVONE, 5,7-DIHYDROXY-6-METHOXY-

Systematic Name

English

6-METHOXYBAICALEIN

Common Name

English

OROXYLIN A [MI]

Common Name

English

Code System Code Type Description

FDA UNII

53K24Z586G